Recycled content polyester compositions and methods of making and using the same

Abstract

Recycled content polyethylene terephthalate (r-PET) compositions are provided. In aspects, the r-PET compositions include a blend of mechanically recycled PET (mr-PET) and chemically recycled PET (cr-PET), optionally with virgin PET. Such compositions can provide higher levels of recycled content, but still achieve desirable values for properties, such as haze and color. A wide variety of recycled content articles can be formed from these r-PET compositions.

Description

RECYCLED CONTENT POLYESTER COMPOSITIONS AND METHODS OF MAKING AND USING THE SAMEBACKGROUND

[0001] This technology relates to the field of chemical recycling of waste plastic and, in particular, to the chemical recycling of polyesters.

[0002] Recycling of plastics has become an important issue facing society. Polyethylene terephthalate, or PET, is one of the most widely recycled plastics. Currently, most of the PET recycling is mechanical recycling, wherein the polyester is physically separated from other plastics, cleaned, and reprocessed via a physical method, such as melt blending. Chemical recycling is an alternative to mechanical recycling and includes chemical decomposition of the PET molecules back to its original monomers, usually terephthalic acid (TPA) or dimethyl terephthalate (DMT) and ethylene glycol (EG), or even bis(hydroxyethyl) terephthalate (BHET). These compounds are then purified and can be re-polymerized to form new PET polymers, which are nearly identical to virgin PET material.

[0003] There are several types of chemical recycling, and these are typically categorized by the depolymerization agent utilized. Most commonly, depolymerization agents include, but are not limited to, water (used in “hydrolysis”), methanol (used in “methanolysis”), and ethylene glycol (used in “glycolysis”). When water is used as the depolymerization agent, PET is depolymerized to form TPA and EG, and when methanol is used as the depolymerization agent, the monomers recovered are DMT and EG. When EG is used as the depolymerization agent, bis(hydroxyethyl) terephthalate (BHET) or oligomers thereof (depending on how much ethylene glycol is used) is formed.

[0004] Dimethyl terephthalate (DMT) is a monomer widely employed as a feedstock for producing several different polymers, including PET. Although nearly identical to virgin DMT, recycled content DMT (r-DMT) formed by depolymerization of waste plastic may include impurities not found in virgin materials (e.g., residual catalysts, various decomposition products, etc.). These non-DMT impurities may be potentially problematic to certain properties of the polymers formed from the r-DMT, even in small quantities. Further, theexact amount of these impurities in the r-DMT fluctuates widely based on the composition of waste plastic fed into the depolymerization step. Thus, ensuring consistent levels of impurity removal can be challenging, particularly when r-DMT with very low impurity levels is demanded.

[0005] Thus, a need exists for a robust method of removing various impurities from recycled content DMT that can be implemented on a commercial scale and without significant impact to the overall process flow or output of chemical recycling facilities. Such a purified r-DMT should be widely usable as a feedstock for several types of polyesters, including those that would be adversely impacted by higher levels of non-DMT impurities.SUMMARY

[0006] In one aspect, the present technology concerns a process for chemically recycling waste plastic, the process comprising: (a) depolymerizing a waste plastic feed stream comprising polyethylene terephthalate (PET) in a depolymerization zone to thereby provide a terephthalate-containing depolymerization stream comprising recycled content dimethyl terephthalate (r-DMT); (b) crystallizing at least a portion of the terephthalate-containing depolymerization stream in a crystallization zone to thereby form a crude r-DMT solids stream; (c) melting at least a portion of the crude r-DMT solids stream in a melting zone to provide a molten crude r-DMT stream comprising r-DMT and one or more non-DMT impurities; and (d) distilling at least a portion of the molten crude r-DMT stream in a reactive distillation zone to thereby provide a purified r-DMT stream comprising a higher concentration of r-DMT than the molten crude r-DMT stream introduced into the reactive distillation zone, wherein the purified r-DMT stream comprises an amount of elemental antimony of less than 1 part per million by weight (ppm) and / or a free ethylene glycol (EG) content of not more than 250 ppm.

[0007] In one aspect, the present technology concerns a process for chemically recycling waste plastic, the process comprising: (a) depolymerizing a waste plastic feed stream comprising polyethylene terephthalate (PET) in a depolymerization zone to thereby provide a terephthalate-containing depolymerization stream comprising recycled content dimethyl terephthalate (r-DMT); (b) crystallizing at least a portion of the terephthalate-containingdepolymerization stream in a crystallization zone to thereby form a crude r-DMT solids stream; (c) melting at least a portion of the crude r-DMT solids stream in a melting zone to provide a molten crude r-DMT stream comprising r-DMT and one or more non-DMT impurities; and (d) introducing a catalyst into the molten crude r-DMT stream, wherein the catalyst is selected to facilitate chemical reaction between two or more components within the molten crude r-DMT; and (e) distilling at least a portion of the molten crude r-DMT stream in a distillation zone to thereby provide a purified r-DMT product stream, wherein the purified r-DMT stream comprises an amount of elemental antimony of less than 1 part per million by weight (ppm) and / or a free ethylene glycol (EG) content of not more than 250 ppm.

[0008] In one aspect, the present technology concerns a process for chemically recycling waste plastic, the process comprising: (a) depolymerizing a waste plastic feed stream comprising polyethylene terephthalate (PET) in a depolymerization zone to thereby provide a terephthalate-containing depolymerization stream comprising recycled content dimethyl terephthalate (r-DMT); (b) crystallizing at least a portion of the terephthalate-containing depolymerization stream in a crystallization zone to thereby form a crude r-DMT solids stream; (c) melting at least a portion of the crude r-DMT solids stream in a melting zone to provide a molten crude r-DMT stream comprising r-DMT and one or more non-DMT impurities; and (d) purifying at least a portion of the molten crude r-DMT stream in a purification zone to thereby provide a purified r-DMT product stream, wherein the non-DMT impurities comprise free ethylene glycol (free EG) and wherein the purifying removes at least a portion of the free EG such that the amount of free EG in the purified r-DMT product stream is less than 50 percent by weight of the amount of free EG in the molten crude r-DMT, wherein the purified r-DMT stream comprises an amount of elemental antimony of less than 1 part per million by weight (ppm) and / or a free ethylene glycol (EG) content of not more than 250 ppm.

[0009] In one aspect, the present technology concerns a recycled content dimethyl terephthalate (r-DMT) composition formed by depolymerization of waste polyethylene terephthalate (PET), the composition comprising: at least 95 weight percent of dimethyl terephthalate having recycled content (r-DMT); from 1 part per billion by weight (ppb) to less than 500 ppb ofelemental antimony (Sb); and less than about 500 parts per million of total ethylene glycol (total EG), wherein all amounts are based on the total weight of the composition.

[0010] In one aspect, the present technology concerns a recycled content dimethyl terephthalate (r-DMT) composition formed by depolymerization of waste polyethylene terephthalate (PET), the composition comprising: at least 95 weight percent of dimethyl terephthalate having recycled content (r-DMT); from 1 ppb to 500 ppb of elemental antimony (Sb); not more than about 250 ppm of free ethylene glycol; not more than 700 ppm of mono(2-hydroxyethyl) terephthalate (MHET); from 7.5 ppm to 500 ppm of methyl hydrogen terephthalate (MHT), wherein all amounts are based on the total weight of the composition.

[0011] In one aspect, the present technology concerns a process for chemically recycling waste plastic, the process comprising: (a) depolymerizing a feed stream comprising waste polyethylene terephthalate (PET) to thereby provide a terephthalate-containing depolymerization stream; (b) crystallizing at least a portion of the terephthalate-containing depolymerization stream to thereby form a crystallized crude recycled content dimethyl terephthalate (r-DMT); (c) melting at least a portion of the crystallized crude r-DMT to thereby form a molten crude r-DMT stream that comprises r-DMT and one or more non-DMT impurities; and (d) purifying at least a portion of the molten crude r-DMT stream in a purification zone to thereby provide a purified r-DMT stream, wherein the purified r-DMT stream comprises: at least 95 percent by weight of dimethyl terephthalate; from 1 part per billion by weight (ppb) to 500 ppb of elemental antimony (Sb); and less than about 500 parts per million by weight (ppm) of total ethylene glycol (total EG), wherein all amounts are based on the total weight of the r-DMT stream.

[0012] In one aspect, the present technology concerns a recycled content dimethyl terephthalate (r-DMT) composition formed by depolymerization of waste polyethylene terephthalate (PET), the composition comprising at least 95 weight percent of dimethyl terephthalate having recycled content (r-DMT); and from 1 part per billion by weight (ppb) and 500 ppb of elemental antimony, wherein all amounts are based on the total weight of the composition.

[0013] In one aspect, the present technology concerns a recycled content dimethyl terephthalate (r-DMT) composition formed by depolymerization of waste polyethylene terephthalate (PET), the composition comprising: at least 97.5 weight percent of dimethyl terephthalate having recycled content (r-DMT); from 1 ppb to 250 ppb of elemental antimony (Sb); and from about 7.5 ppm to about 500 ppm of methyl hydrogen terephthalate (MHT), wherein all amounts are based on the total weight of the composition.

[0014] In one aspect, the present technology concerns a process for chemically recycling waste plastic, the process comprising: (a) depolymerizing a feed stream comprising waste polyethylene terephthalate (PET) to thereby provide a terephthalate-containing depolymerization stream; (b) crystallizing at least a portion of the terephthalate-containing depolymerization stream to thereby form a crystallized crude recycled content dimethyl terephthalate (r-DMT); (c) melting at least a portion of the crystallized crude r-DMT to thereby form a molten crude r-DMT stream that comprises r-DMT and one or more non-DMT impurities; and (d) purifying at least a portion of the molten crude r-DMT stream in a purification zone to thereby provide a purified r-DMT stream, wherein the purified r-DMT stream comprises at least 95 percent by weight dimethyl terephthalate, and wherein the purified r-DMT stream comprises between 1 part per billion by weight (ppb) and 500 ppb of elemental antimony (Sb), based on the total weight of the purified r-DMT stream.

[0015] In one aspect, the present technology concerns a recycled content dimethyl terephthalate (r-DMT) composition formed by depolymerization of waste polyethylene terephthalate (PET), wherein the r-DMT composition comprises at least 95 weight percent of dimethyl terephthalate having recycled content (r-DMT); less than about 250 ppm of free ethylene glycol (free EG); and greater than 7.5 ppm and less than 500 ppm of methyl hydrogen terephthalate (MHT), wherein all amounts are based on the total weight of the composition.

[0016] In one aspect, the present technology concerns a recycled content dimethyl terephthalate (r-DMT) composition formed by depolymerization of waste polyethylene terephthalate (PET), wherein the r-DMT composition comprises: at least 97.5 weight percent of dimethyl terephthalate having recycled content (r-DMT); less than 45 parts per million byweight (ppm) of dimethyl phthalate (DMP); less than 5 ppm of methyl formyl benzoate (MFB); less than 690 ppm of mono(2-hydroxyethyl) terephthalate (MHET); less than about 250 ppm of free ethylene glycol (free EG); and greater than 7.5 ppm and less than 500 ppm of methyl hydrogen terephthalate (MHT), wherein all amounts are based on the total weight of the r-DMT composition.

[0017] In one aspect, the present technology concerns a process for chemically recycling waste plastic, the process comprising: (a) depolymerizing a feed stream comprising waste polyethylene terephthalate (PET) to thereby provide a terephthalate-containing depolymerization stream; (b) crystallizing at least a portion of the terephthalate-containing depolymerization stream to thereby form a crystallized crude recycled content dimethyl terephthalate (r-DMT); (c) melting at least a portion of the crystallized crude r-DMT to thereby form a molten crude r-DMT stream that comprises r-DMT and one or more non-DMT impurities; and (d) purifying at least a portion of the molten crude r-DMT stream in a purification zone to thereby provide a purified r-DMT stream, wherein the purified r-DMT stream comprises at least 95 percent by weight dimethyl terephthalate; less than about 250 ppm of free ethylene glycol (free EG); and methyl hydrogen terephthalate (MHT) in an amount of 7.5 ppm to about 500 ppm, wherein all amounts are based on the total weight of the purified r-DMT stream.

[0018] In one aspect, the present technology concerns a recycled content dimethyl terephthalate (r-DMT) composition formed by depolymerization of waste polyethylene terephthalate (PET), the composition comprising: at least 95 weight percent of dimethyl terephthalate having recycled content (r-DMT); less than 250 parts per million by weight (ppm) of free ethylene glycol (EG); less than 700 ppm of mono(2-hydroxyethyl) terephthalate (MHET); and at least 1 part per billion by weight (ppb) of elemental antimony, wherein all amounts are based on the total weight of the composition.

[0019] In one aspect, the present technology concerns a recycled content dimethyl terephthalate (r-DMT) composition formed by depolymerization of waste polyethylene terephthalate (PET), the composition comprising: at least 97.5 weight percent of dimethyl terephthalate having recycled content (r-DMT); from about 1 part per billion by weight (ppb) to less than 1 part per million by weight (ppm) of elemental antimony (Sb); and lessthan 500 ppm of mono(2-hydroxyethyl) terephthalate (MHET), wherein all amounts are based on the total weight of the r-DMT composition.

[0020] In one aspect, the present technology concerns a process for chemically recycling waste plastic, the process comprising: (a) depolymerizing a feed stream comprising waste polyethylene terephthalate (PET) to thereby provide a terephthalate-containing depolymerization product stream; (b) crystallizing at least a portion of the terephthalate-containing depolymerization product stream to thereby form a crystallized crude recycled content dimethyl terephthalate (r-DMT); (c) melting at least a portion of the crystallized crude r-DMT to thereby form a molten crude r-DMT stream that comprises r-DMT and one or more non-DMT impurities; and (d) purifying at least a portion of the molten crude r-DMT stream in a purification zone to thereby provide a purified r-DMT stream, wherein the purified r-DMT stream comprises at least 95 weight percent of dimethyl terephthalate having recycled content (r-DMT); not more than 250 parts per million by weight (ppm) of free ethylene glycol (EG); less than 700 ppm of mono(2-hydroxyethyl) terephthalate (MHET); and at least 1 part per billion by weight (ppb) of elemental antimony.

[0021] In one aspect, the present technology concerns a recycled content polyester (r-polyester) formed from recycled content dimethyl terephthalate (r-DMT) produced by depolymerization of waste plastic, the r-polyester comprising: (a) a diester component comprising: (i) from 70 to about 100 mole percent of residues of r-DMT; (ii) from 0 to 30 mole percent of residues of at least one modifying diester, wherein each of (i) and (ii) are based on the total moles of diester residues in the r-polyester; and (b) a diol component comprising: (i) from 1 to 99 mole percent of residues of 2,2,4,4-tetramethyl-1 ,4-cyclobutanediol (TMCD); and (ii) from 1 to 99 mole percent of residues of at least one additional diol chosen from cyclohexanedimethanol (CHDM), ethylene glycol (EG), or combinations thereof, wherein each of (i) and (ii) are based on the total moles of diol residues in the r-polyester; and (c) elemental antimony in an amount in the range of from 1 part per billion by weight (ppb) to 850 ppb, based on the total weight of the r-polyester.

[0022] In one aspect, the present technology concerns a recycled content polyester (r-polyester) formed from recycled content dimethyl terephthalate (r-DMT) produced by depolymerization of waste plastic, the r-polyester comprising: (a) a diester component comprising (i) at least 95 mole percent of residues of r-DMT; and (ii) not more than 5 mole percent of residues of at least one modifying diester, wherein (i) and (ii) are based on the total moles of diester residues in the r-polyester; (b) a diol component comprising (i) or (ii): (i) from about 10 to about 65 mole percent of residues of TMCD and about 35 to about 90 mole percent of residues of CHDM; or (ii) from about 55 to about 99 mole percent of residues of EG and about 1 to about 45 mole percent of residues of TMCD, wherein (i) and (ii) are based on the total moles of diol residues in the r-polyester; and (c) elemental antimony (Sb) in an amount in the range of from 1 part per billion by weight (ppb) to 750 ppb, based on the total weight of the r-polyester.

[0023] In one aspect, the present technology concerns a process for producing recycled content polyester (r-polyester), the process comprising: (a) introducing reactants comprising recycled content dimethyl terephthalate (r-DMT), 2,2,4,4-tetramethyl-1 ,4-cyclobutanediol (TMCD), and at least one additional diol chosen from cyclohexanedimethanol (CHDM) and ethylene glycol (EG) into a transesterification zone; (b) transesterifying at least a portion of the r-DMT, the TMCD, and the additional diol in the transesterification zone to thereby form a recycled content polyester oligomer (r-polyester oligomer); and (c) polycondensing at least a portion of the r-polyester oligomer in a polycondensation zone to thereby form a recycled content polyester (r-polyester), wherein the r-DMT introduced into the transesterification zone comprises (i) at least 95 weight percent of dimethyl terephthalate having recycled content (r-DMT); (ii) elemental antimony in an amount of at least 1 part per billion by weight (ppb) and less than 1 part per million by weight (ppm); (iii) at least one of the following (A) to (C): (A) less than 45 ppm of dimethyl phthalate (DMP); (B) less than 700 ppm of mono(2-hydroxyethyl) terephthalate (MHET); and (C) less than 500 ppm of methyl hydrogen terephthalate (MHT).

[0024] In one aspect, the present technology concerns a recycled content copolyester (r-polyester) comprising: (a) a diester component comprising residues of recycled content dimethyl terephthalate (r-DMT); and (b) a diol component comprising (i) at least 20 mole percent of residues of cyclohexanedimethanol (CHDM); (ii) not more than 75 mole percent of residues of ethylene glycol (EG); and (iii) less than 5 mole percent of residues of diolsother than CHDM and EG, wherein each of (i) through (iii) are based on the total moles of diol residues present in the r-polyester, and wherein the r-polyester has an elemental antimony content in the range of from 1 part per billion by weight (ppb) to 850 ppb, based on the total weight of the r-polyester.

[0025] In one aspect, the present technology concerns a recycled content polyester (r-polyester) comprising: (a) a diester component comprising residues of recycled content dimethyl terephthalate (r-DMT); (b) a diol component comprising (i) about 25 to 100 mole percent of residues of cyclohexanedimethanol (CHDM); (ii) 0 to about 75 mole percent of residues of ethylene glycol (EG); and (iii) less than 3 mole percent of residues of glycols other than CHDM and EG, wherein each of (i) through (iii) are based on the total moles of diol residues present in the r-polyester, and wherein said r-polyester has an elemental antimony content in the range of from 1 part per billion by weight (ppb) to 500 ppb, based on the total weight of r-polyester.

[0026] In one aspect, the present technology concerns a process for producing recycled content polyester (r-polyester), the process comprising: (a) introducing dimethyl terephthalate comprising recycled content (r-DMT) and cyclohexanedimethanol (CHDM) into a transesterification zone; (b) transesterifying at least a portion of the r-DMT with at least a portion of the CHDM in the transesterification zone to thereby form a recycled content polyester oligomer (r-polyester oligomer); and (c) polycondensing at least a portion of the r-polyester oligomer in a polycondensation zone to thereby form a recycled content polyester (r-polyester), wherein the r-DMT introduced into the transesterification zone comprises: (i) at least 95 weight percent of dimethyl terephthalate having recycled content (r-DMT); (ii) elemental antimony in an amount of at least about 1 part per billion by weight (ppb) and less than 1 part per million by weight (ppm); (iii) at least one of the following (A) through (C): (A) less than 45 ppm of dimethyl phthalate (DMP); (B) less than 700 ppm of mono(2-hydroxyethyl) terephthalate (MHET); and (C) less than 500 ppm of methyl hydrogen terephthalate (MHT), wherein all amounts are based on the total weight of the r-DMT introduced into the transesterification zone.

[0027] In one aspect, the present technology concerns a recycled content polyethylene terephthalate (r-PET) formed from recycled content dimethyl terephthalate (r-DMT), the r-PET comprising: (a) a diester componentcomprising residues of recycled content (r-DMT); (b) a diol component comprising residues of ethylene glycol (EG); wherein the r-PET has an elemental antimony content in the range of from 1 part per billion by weight (ppb) to 850 ppb, based on the total weight of the r-PET.

[0028] In one aspect, the present technology concerns a process for producing recycled content polyester (r-PET), the process comprising: (a) introducing dimethyl terephthalate having recycled content (r-DMT), ethylene glycol, and optionally at least one additional diol other than ethylene glycol into a transesterification zone; (b) transesterifying at least a portion of the dimethyl terephthalate, the ethylene glycol, and, when present, the additional diol other than ethylene glycol in the transesterification zone to thereby form a recycled content polyester oligomer (r-PET oligomer); and (c) polycondensing at least a portion of the r-PET oligomer in a polycondensation zone to thereby form a recycled content polyester (r-PET), wherein the r-DMT introduced into the transesterification zone comprises (i) at least 95 weight percent of dimethyl terephthalate having recycled content (r-DMT); (ii) from about 1 part per billion by weight (ppb) to less than 1 part per million by weight (ppm) of elemental antimony; (iii) at least one of the following (A) through (C): (A) less than 45 ppm of dimethyl phthalate (DMP); (B) less than 700 ppm of mono(2-hydroxyethyl) terephthalate (MHET); and (C) less than 500 ppm of methyl hydrogen terephthalate (MHT).

[0029] In one aspect, the present technology concerns a recycled content polyester (r-polyester) formed from recycled content dimethyl terephthalate (r-DMT), the r-polyester comprising (a) a diester component comprising residues of recycled content dimethyl terephthalate (r-DMT); and (b)a diol component comprising at least 1 mole percent of isosorbide residues, wherein the r-polyester has an elemental antimony content in the range of from 1 part per billion by weight (ppb) to 1 part per million (ppm), based on the total weight of the r-polyester.

[0030] In one aspect, the present technology concerns a process for producing recycled content polyester (r-polyester), the process comprising: (a) introducing dimethyl terephthalate comprising recycled content dimethyl terephthalate (r-DMT) and at least one diol comprising isosorbide into a transesterification zone; (b) transesterifying at least a portion of the r-DMT andthe diol in the transesterification zone to thereby form a recycled content polyester oligomer (r-polyester oligomer); and (c) polycondensing at least a portion of the r-polyester oligomer in a polycondensation zone to thereby form a recycled content polyester (r-polyester), wherein the r-DMT introduced into the transesterification zone comprises (i) at least 95 weight percent of dimethyl terephthalate having recycled content (r-DMT); (ii) from about 1 part per billion by weight (ppb) to less than 1 part per million by weight (ppm) of elemental antimony; and (iii) at least one of the following (A) through (C): (A) less than 45 ppm of dimethyl phthalate (DMP); (B) less than 700 ppm of mono(2-hydroxyethyl) terephthalate (MHET); and (C) less than 500 ppm of methyl hydrogen terephthalate (MHT), wherein all amounts are based on the total weight of the composition.

[0031] In one aspect, the present technology concerns a recycled content polyethylene terephthalate (r-PET) composition having a recycled content of greater than 50 percent and a haze value of at least 2% and not more than 20%, measured according to ASTM D-1003 using a 1 / 8-inch thick plaque.

[0032] In one aspect, the present technology concerns a recycled content polyethylene terephthalate (r-PET) composition having a recycled content of greater than 50 percent, wherein the r-PET composition comprises: (a) at least one characteristic (i) or (ii): (i) from about 0.2 to about 3 percent of methyl end groups based on the total number of end groups, as determined by NMR; and (ii) from about 0.1 to about 10 mole percent of residues of cyclohexanedimethanol (CHDM), based on the total moles of diol residues in the r-PET composition; (b) at least one characteristic (iii) to (v): (iii) at least 5 parts per million by weight (ppm) of total chloride (Cl); (iv) at least 5 ppm of total nitrogen (N); and (v) a haze value of at least 2%, measured by ASTM D-1003 with a 1 / 8-inch plaque.

[0033] In one aspect, the present technology concerns a recycled content polyethylene terephthalate (r-PET) composition having a recycled content of at least 10 percent, wherein the r-PET composition comprises one or both of (a) and (b): (a) an amount of total chloride (Cl) at least 5 parts per million by weight (ppm) and less than 15 ppm; and / or (b) an amount of total nitrogen (N) at least 5 ppm and less than 15 ppm, wherein each amount (a) and (b) is based on the total weight of the r-PET composition, and wherein the r-PET composition does not include 100 weight percent of mechanically recycled PET (mr-PET).

[0034] In one aspect, the present technology concerns a recycled content PET (r-PET) composition comprising: 5 to 75 weight percent chemically recycled PET (cr-PET); 5 to 75 weight percent mechanically recycled PET (mr-PET); and optionally, 5 to 45 weight percent of virgin PET, wherein the combined amount of cr-PET, mr-PET, and virgin PET, when present, are at least 95 weight percent of the r-PET composition.

[0035] In one aspect, the present technology concerns a recycled content PET (r-PET) composition comprising at least 5 weight percent of chemically recycled PET (cr-PET), at least 5 weight percent of mechanically recycled PET (mr-PET), and optionally at least 5 weight percent of virgin PET, wherein the r-PET composition has a total recycled content of greater than 50%, wherein the combined amount of cr-PET, mr-PET, and virgin PET, when present, are at least 95 weight percent of the composition, and wherein the r-PET composition has one or both of the following properties (i) and / or (ii): (i) an L* value of at least 80, measured according to 1976 CIE L*a*b* Color Space; and / or (ii) a haze value of less than 20 percent, measured according to ASTM D-1003 Method A with a 1 / 8-inch plaque.

[0036] In one aspect, the present technology concerns a recycled content polyethylene terephthalate (r-PET) composition comprising at least 5 weight percent of chemically recycled PET (cr-PET), at least 5 weight percent of mechanically recycled PET (mr-PET), and at least 5 weight percent of virgin PET, wherein the r-PET composition has a total recycled content of greater than 50%, wherein the combined amount of cr-PET, mr-PET, and virgin PET are at least 95 weight percent of the composition, and wherein the r-PET composition has one or both of the following properties (i) and / or (ii): (i) an L* value, measured according to 1976 CIE L*a*b* Color Space, within about 15 of the L* value of the virgin PET; and / or (ii) a haze value, measured according to ASTM D-1003 with a 1 / 8-inch plaque, within about 20 percent of the haze value of the virgin PET.

[0037] In one aspect, the present technology concerns a method of making a recycled content polyethylene terephthalate (r-PET) composition,said method comprising mixing mechanically recycled PET (mr-PET) and chemically recycled PET (cr-PET) to form a blended r-PET composition.

[0038] In one aspect, the present technology concerns a method of making a recycled content polyethylene terephthalate (r-PET) composition, the method comprising: (a) setting a target value for at least one property of the r-PET composition; (b) blending mechanically recycled PET (mr-PET) and virgin PET to provide a first r-PET blend; (c) measuring a value of the property in (a) for the first r-PET blend to provide a first measured value; (d) comparing the first measured value with the target value to determine a first difference; (e) based on the first difference, mixing an amount of chemically recycled PET (cr-PET) with an amount of mechanically recycled PET (mr-PET) to form a second r-PET blend; (f) measuring a value of the property in (a) for the second r-PET blend to provide a second measured value; (g) comparing the second measured value with the target value to determine a second difference; and (h) when the second difference is greater than 50 percent of the target value, repeating (e) through (g) until the second difference is 50 percent or less of the target value, as determined by the formula: absolute value of (target value -second measured value) I target value, expressed as a percent.

[0039] In one aspect, the present technology concerns a recycled content article of manufacture (r-article) formed from a recycled content polyethylene terephthalate (r-PET) composition, wherein r-article has a recycled content of greater than 50 percent and has a haze value, measured according to ASTM D-1003 using a 1 / 8-in thick plaque, of at least 2% and not more than 20%.

[0040] In one aspect, the present technology concerns a recycled content plastic article (r-article) formed from a recycled content polyethylene terephthalate (r-PET) composition, said r-article having a recycled content of greater than 50 percent, wherein the article comprises: (a) at least one characteristic (i) or (ii): (i) from about 0.2 to about 3 percent of methyl end groups based on the total number of end groups, as determined by NMR; (ii) from about 0.1 to about 10 mole percent of residues of cyclohexanedimethanol (CHDM), based on the total moles of diol residues in the r-PET composition; and (b) at least one characteristic (iii) to (v): (iii)at least 5 parts per million by weight (ppm) of total chloride (Cl); (iv) at least 5 ppm of total nitrogen (N); and(v) a haze value of at least 3%, measured by ASTM D-1003 with a 1 / 8-inch plaque.

[0041] In one aspect, the present technology concerns a recycled content plastic article (r-article) formed from a recycled content polyethylene terephthalate (r-PET) composition, said r-article having a recycled content of at least 10 percent and wherein the r-article composition comprises one or both of (a) and (b): (a) an amount of total chloride (Cl) at least 5 parts per million by weight (ppm) and less than 15 ppm; and / or (b) an amount of total nitrogen (N) at least 5 ppm and less than 15 ppm, wherein each amount (a) and (b) is based on the total weight of the r-article, and wherein the r-article is not formed from 100 weight percent of mechanically recycled PET (mr-PET).

[0042] In one aspect, the present technology concerns a recycled content plastic article (r-article) formed from a recycled content polyethylene terephthalate (r-PET) composition comprising: 5 to 75 weight percent chemically recycled PET (cr-PET); 5 to 75 weight percent mechanically recycled PET (mr-PET); and optionally, 5 to 45 weight percent of virgin PET, wherein the combined amount of cr-PET, mr-PET, and virgin PET, when present, are at least 95 weight percent of the r-PET composition.

[0043] In one aspect, the present technology concerns a recycled content plastic article (r-article) formed from a recycled content polyethylene terephthalate (r-PET) composition comprising at least 5 weight percent of chemically recycled PET (cr-PET), at least 5 weight percent of mechanically recycled PET (mr-PET), and optionally at least 5 weight percent of virgin PET, wherein the r-PET composition has a total recycled content of greater than 50%, wherein the combined amount of cr-PET, mr-PET, and virgin PET, when present, are at least 95 weight percent of the composition, and wherein the r-article has one or both of the following properties (i) and / or (ii): (i) an L* value of at least 80, measured according to 1976 CIE L*a*b* Color Space; and / or (ii) a haze value of less than 20 percent, measured according to ASTM D-1003 Method A using a 1 / 8-inch plaque.

[0044] In one aspect, the present technology concerns a recycled content plastic article (r-article) formed from a recycled content polyethylene terephthalate (r-PET) composition comprising at least 5 weight percent of chemically recycled PET (cr-PET), at least 5 weight percent of mechanicallyrecycled PET (mr-PET), and at least 5 weight percent of virgin PET, wherein the combined amount of cr-PET, mr-PET, and virgin PET are at least 95 weight percent of the composition, wherein the r-PET composition has a total recycled content of greater than 50%, and wherein the r-article has one or both of the following properties (i) and / or (ii): (i) an L* value, measured according to 1976 CIE L*a*b* Color Space, within about 15 of the L* value of the virgin PET; and / or (ii) a haze value, measured according to ASTM D-1003 with a 1 / 8-inch plaque, within about 20 percent of the haze value of the virgin PET.BRIEF DESCRIPTION OF THE DRAWINGS

[0045] FIG. 1 is a schematic block flow diagram illustrating the main steps and / or processing zones of a facility configured for the chemical recycling of waste plastic, including, for example, waste polyethylene terephthalate;

[0046] FIG. 2 is a schematic block flow diagram illustrating a portion of the chemical recycling facility shown in FIG. 1 and, in particular, a dimethyl terephthalate (DMT) processing step / zone configured according to embodiments of the present technology;

[0047] FIG. 3a is a schematic block flow diagram illustrating a portion of the DMT processing step / zone shown in FIG. 2 and, in particular, a solvent contact vessel or stage for removing non-DMT impurities from a stream of crude r-DMT according to embodiments of the present technology;

[0048] FIG. 3b is a schematic block flow diagram illustrating a portion of the DMT processing step / zone shown in FIG. 2 and, in particular, a distillation vessel or stage for removing non-DMT impurities from a stream of crude r-DMT according to embodiments of the present technology;

[0049] FIG. 4 is a schematic block flow diagram illustrating the major steps of a polyester production facility and, in particular, a polyester production facility configured to receive and process recycled content dimethyl terephthalate (r-DMT) formed according to embodiments of the present technology;

[0050] FIG. 5a is a schematic block flow diagram illustrating the major steps of a polyester production facility as generally shown in FIG. 4 and, in particular, illustrating a facility configured to produce polyester pellets formedfrom a blend of mechanically recycled polyester and chemically recycled polyester;

[0051] FIG. 5b is a schematic block flow diagram illustrating the major steps of a polyester production facility as generally shown in FIG. 4 and, in particular, illustrating a facility configured to produce a blend of mechanically recycled polyester pellets and chemically recycled polyester pellets; and

[0052] FIG. 6 is a flow diagram illustrating the major steps in a method for forming a blended recycled content PET (r-PET) composition.DETAILED DESCRIPTION

[0053] We have discovered new methods and systems relating to the chemical recycling of waste plastic, including polyethylene terephthalate, or PET. In particular, we have discovered improved methods and systems for producing purified recycled content dimethyl terephthalate (r-DMT), as well as improvements in the end products, such as polyesters, formed from the purified r-DMT.

[0054] Turning initially to FIG. 1, the main process steps / zones of a facility 10 for the chemical recycling of waste plastic are illustrated. As shown in FIG. 1, the chemical recycling facility 10 includes the basic steps of (1) depolymerization of waste plastic, including polyester, to form a depolymerization mixture, followed by (2) separation of at least a portion of the depolymerization mixture to form purified streams of recycled content monomers, including recycled content dimethyl terephthalate (r-DMT) and recycled content ethylene glycol (r-EG). Additionally, as shown in FIG. 1, the chemical recycling facility 10 includes a feed treatment section 20 for removing impurities (e.g., dirt, cardboard, paper, etc.) and other plastics (e.g., PVC, polycarbonate, polyolefins, etc.) from the mixed plastic waste stream prior to depolymerization.

[0055] Chemical recycling facilities are not mechanical recycling facilities. As used herein, the terms “mechanical recycling” and “physical recycling” refer to a recycling process that includes a step of melting waste plastic and forming the molten plastic into a new intermediate product (e.g., pellets or sheets) and / or a new end product (e.g., bottles). Generally, mechanical recycling does not substantially change the chemical structure ofthe plastic being recycled. The chemical recycling facilities described herein may be configured to receive and process waste streams from and / or that are not typically processable by a mechanical recycling facility. In some embodiments, chemically recycled and mechanically recycled polyester may be combined to form a high recycled content (e.g., greater than 50 percent) end product.

[0056] According to some embodiments, the chemical recycling process performed at the facility 10 may be a continuous process, or at least a portion may be carried out as a batch process (e.g., a semi-continuous process). The term “continuous” as used herein means a process wherein the reactants are introduced, and the products are withdrawn simultaneously in an uninterrupted manner.

[0057] In some embodiments, the chemical recycling facility 10 may be a commercial-scale facility. As used herein, the term “commercial scale facility,” in reference to a chemical recycling facility, means the facility has an average annual waste plastic feed rate to the depolymerization reactor(s) of at least 500 pounds per hour (Ibs / h), averaged over one year. For example, in some cases, the chemical recycling facility has an average annual feed rate of at least 750, at least 1 ,000, at least 2,000, at least 5,000, at least 10,000, at least 50,000, or at least 100,000 Ibs / h and / or not more than about 1 ,000,000, not more than about 500,000, or not more than about 250,000 Ibs / h to the depolymerization reactor(s), averaged over one year. Where a chemical recycling facility includes two or more depolymerization reactors, the feed rate is the total feed to all reactors operated in parallel.

[0058] In some embodiments, the chemical recycling facility 10 may be a pilot-scale facility, but it may not be a lab-scale facility. As used herein, the term “pilot-scale,” in reference to a chemical recycling facility, means the facility has an average annual waste plastic feed rate to the depolymerization reactor(s) of between 5 and less than 500 Ibs / h, averaged over one year. Pilotscale facilities may have an average annual feed rate of at least about 25, at least about 50, at least about 100, or at least about 250 Ib / h and / or not more than about 450, not more than about 400, not more than about 350, or not more than about 300 Ib / h, averaged over one year. Lab-scale facilities are those conducted in a laboratory, typically in a batch-wise manner. Lab-scaleprocesses can have a feed rate of less than 1 , less than about 0.5, or less than about 0.25 Ib / h, if conducted continuously, or less than 5 pounds of waste plastic feed per batch if conducted in a batch-wise manner.

[0059] In some embodiments, the feed rate to the chemical recycling facility (or, as discussed below, to the depolymerization step or zone) can be at least about 100,000, at least about 110,000, at least about 120,000, at least about 125,000, at least about 130,000, at least about 135,000, at least about 140,000, at least about 145,000, at least about 150,000, at least about 155,000, at least about 160,000, at least about 165,000, at least about 170,000, at least about 175,000, at least about 180,000, at least about 185,000, at least about 190,000, at least about 195,000, at least about 200,000, at least about 205,000, at least about 210,000, at least about 215,000, or at least about 220,000 lbs per year and / or not more than about 1 ,000,000, not more than about 750,000, or not more than about 500,000 lbs per year, measured on an average of 300 on-stream days per year.

[0060] In some embodiments, the production rate of purified r-DMT (or other r-monomer product or r-polyester) from the chemical recycling facility 10 can be at least about 100,000, at least about 110,000, at least about 120,000, at least about 125,000, at least about 130,000, at least about 135,000, at least about 140,000, at least about 145,000, at least about 150,000, at least about 155,000, at least about 160,000, at least about 165,000, at least about 170,000, at least about 175,000, at least about 180,000, at least about 185,000, at least about 190,000, at least about 195,000, at least about 200,000, at least about 205,000, at least about 210,000, at least about 215,000, or at least about 220,000 lbs per year and / or not more than about 1,000,000, not more than about 750,000, or not more than about 500,000 lbs per year, measured on an average of 300 on-stream days per year.

[0061] The mixed waste plastic waste stream introduced into the chemical recycling facility 10 via line 110 can include one or more types of waste plastic, including, for example polyethylene terephthalate (PET). As used herein, the term “PET” refers to a homopolymer of polyethylene terephthalate, or polyethylene terephthalate modified with modifiers or containing residues or moieties of other than ethylene glycol (EG) and terephthalic acid (or a dimethyl terephthalate), such as isophthalic acid, 1 ,4-cyclohexanedicarboxylic acid,diethylene glycol, TMCD (2,2,4,4-tetramethyl-1 ,3-cyclobutanediol), CHDM (cyclohexanedimethanol), propylene glycol, isosorbide, 1 ,4-butanediol, 1 ,3-propane diol, and / or NPG (neopentyl glycol), or polyesters having repeating terephthalate units (and whether or not they contain repeating ethylene glycol based units) and one or more residues or moieties of TMCD (2, 2,4,4-tetramethyl-1,3-cyclobutanediol), CHDM (cyclohexanedimethanol), propylene glycol, or NPG (neopentyl glycol), isosorbide, isophthalic acid, 1 ,4-cyclohexanedicarboxylic acid, 1,4-butanediol, 1,3-propane diol, and / or diethylene glycol, or combinations thereof. As used herein, “PET” is defined according to ASTM D5047 as including at least 90 mole percent of polyethylene terephthalate residues and having a melting point of at least 225°C. The term “polyester” is broader and refers simply to a polymer formed by reaction of a diester (or diacid) and diol that includes ester repeating units and may refer to both PET and non-PET polyesters.

[0062] As used herein, the terms “mixed plastic waste” or “mixed waste plastic” refer to heterogeneous waste streams comprising various types of polymers and plastics, as well as other organic and inorganic components, which has been previously used and discarded. The mixed plastic waste stream in line 110 may include material that was recovered as manufacturing scrap, post-industrial waste, post-consumer waste, or a combination thereof. In some embodiments, the recycled polyester(s) in the mixed plastic waste stream can be products and / or materials that have been used and / or discarded. The mixed plastic waste stream in line 110 may comprise less than about 1, less than about 0.5, less than about 0.1 , or less than about 0.01 weight percent of virgin material, including virgin PET. As used herein, the term “virgin” refers to a polymeric material that has not been used or processed. In some embodiments, the waste plastic stream can come from various sources and / or be in various forms, including but not limited to fibers from textiles and / or carpet, thermoformed materials, bottles, flakes, pellets, fines, and sheets and / or film, as well as portions or fragments of one or more of these. In some embodiments, the waste plastic stream may include waste packaging materials such as films, sheets, wrappings, and / or strappings.

[0063] In some embodiments, the mixed plastic waste feed stream in line 110 may not include certain materials or plastics, including plastics fromcertain sources. For example, in some embodiments, the mixed plastic waste feed stream in line 110 (or the feed the depolymerization step or zone discussed below) may comprise less than about 50, not more than about 45, not more than about 40, not more than about 35, not more than about 30, not more than about 25, not more than about 20, not more than about 15, not more than about 10, not more than about 5, not more than about 2, not more than about 1, or not more than 0 percent of polyester originating from commercial, industrial, and / or medical and / or dental x-ray film. In some embodiments, the mixed plastic waste feed stream (or feed stream to the depolymerization step or zone) may comprise about 0 ppm or less than about 5, less than about 4, less than about 3, less than about 2, less than about 1 , or less than about 0.5 ppm of total Silver (Ag), even though the waste plastic has not undergone a silver extraction step upstream or prior to being introduced into the chemical recycling facility (or depolymerization step or zone).

[0064] Other components in the mixed plastic waste feed stream in line 110 may include other non-PET waste plastics and / or other non-plastic waste components. Examples of non-PET waste plastics can include, but are not limited to, polyesters other than PET, polyvinyl acetal, polyvinylbutyral (PVB), polyvinyl alcohol (PVOH), ethylene vinyl alcohol (EVOH), cotton, polystyrene, polycarbonate, cellulose esters, polyacrylate, polymethacrylates, poly(lactic acid), polydimethylsiloxane, polysilane, polyethylene, polypropylene, polyolefins other than polyethylene and polypropylene, polyvinyl chloride (PVC), elastane, nylon, polyacrylates, polymethacrylate, poly(lactic acid), or combinations thereof. Non-polymeric waste components present in the waste plastic stream in line 110 may include, for example, natural fibers, calcium carbonate, titanium dioxide, inorganic fillers, dyes, pigments, color toners, colorants, plasticizers, adhesives, flame retardants, carbon black, or combinations thereof, as well as other organic waste materials such as dirt, dust, food, and cellulosic materials such as paper and cardboard, and / or inorganic waste materials such as glass, metals like aluminum and iron, rocks, and combinations thereof.

[0065] As shown in FIG. 1, the mixed plastic waste stream introduced into the facility 10 via line 110 may undergo one or more pre-processing steps in a feed treatment step / zone 20 prior to entering the depolymerizationstep / zone 30. In feed treatment step / zone 20, as much of the non-plastic and non-PET materials are removed from the stream as possible. Examples of preprocessing steps suitable for use in feed treatment step / zone 20 include, but are not limited to, washing, drying, sorting, size reduction, and combinations thereof. The resulting treated plastic waste stream in line 112, which comprises predominantly waste PET, may be in the form of flakes, powder, pellets, and / or chunks. The moisture content of the material in line 112 can be not more than about 10, not more than about 8, not more than about 5, not more than about 3, not more than about 2, or not more than about 1 weight percent and / or at least about 0.1 , at least about 0.5, or at least about 1 weight percent, based on the total weight of the material in line 112.

[0066] The treated waste plastic stream in line 112 comprises waste PET in an amount of at least about 60, at least about 65, at least about 70, at least about 75, at least about 80, at least about 85, or at least about 90, at least about 92, at least about 95, at least about 97, at least about 98, at least about 98.5, at least about 99, at least about 99.5, or at least about 99.9 weight percent and / or about 100 percent, or not more than about 99, not more than about 97, not more than about 95, not more than about 90, not more than about 85, not more than about 80, or not more than about 75 weight percent, based on the total weight of the waste plastic stream in line 110. The total amount of non-PET components in the stream in line 112 can be about 0 percent, or at least about 1 , at least about 2, at least about 5, at least about 10, at least about 15, at least about 20, or at least about 25 weight percent and / or not more than about 40, not more than about 35, not more than about 30, not more than about 25, not more than about 20, not more than about 15, not more than about 10, not more than about 5, not more than about 3, not more than about 2, not more than about 1.5, not more than about 1, not more than about 0.5, or not more than about 0.1 weight percent, based on the total weight of the stream in line 112.

[0067] As shown in FIG. 1 , the predominantly PET waste plastic stream in line 112 may be introduced into a depolymerization step or zone 30, wherein the waste PET may be treated via contact with at least one depolymerization solvent (introduced via line 116) to reduce the molecular weight of the waste PET via a depolymerization reaction. During the depolymerization reaction, thePET can be broken down into its constituent monomers (e.g., ethylene glycol and dimethyl terephthalate), along with a variety of other diesters, half-esters, and oligomers. Examples of suitable depolymerization solvents can include, but are not limited to, water; C1 to C14 alcohols; and C2 to C14 diols such as ethylene glycol and diethylene glycol. When the depolymerization solvent comprises a C1 to C14 alcohol, it may comprise (or consist of or consist essentially of) methanol, ethanol, a C4 to C14 alcohol, or a C6 to C12 alcohol. In some embodiments, the depolymerization solvent can comprise one or more chosen from methanol, ethanol, n-butanol, isobutanol, hexanol, 2-ethylhexanol, n-octanol, decanol, dodecanol, tetradecanol, or mixtures thereof.

[0068] According to some embodiments, the depolymerization reaction can be a two-stage reaction with each stage utilizing a different solvent. For example, in some embodiments, waste PET may be subjected to depolymerization with a solvent chosen from C2 to C14 alcohols and glycols (e.g., ethylene glycol or 2-ethylhexanol) and the resulting depolymerization products can be transesterified and / or further depolymerized in a second stage with a solvent comprising methanol. Alternatively, the depolymerization reaction can be a single-stage reaction wherein a C1 to C4 alcohol (e.g., methanol) is used as the only depolymerization solvent.

[0069] One or more of the depolymerization reactions performed in depolymerization step / zone 30 may be carried out at an average temperature of at least about 100, at least about 110, at least about 120, at least about 130, at least about 140, at least about 150, at least about 160, at least about 165, at least about 170, at least about 175, at least about 180, at least about 185, or at least about 190°C and / or not more than about 280, not more than about 275, not more than about 250, not more than about 240, not more than about 230, not more than about 220, not more than about 215, not more than about 210, not more than about 205, not more than about 200, not more than about 195, not more than about 190, not more than about 185, not more than about 180, or not more than about 175°C. Unless otherwise noted, the temperatures described herein with respect to reaction vessels are the average temperatures of the liquid-phase reaction mixtures, while the temperatures of columns or vessels generally refer to the vapor-phase streams removed from a given vessel or process zone or step.

[0070] In some embodiments, the depolymerization reaction temperature may be chosen to provide desired reaction products while minimizing undesirable by-products and in order to achieve maximum efficiency and simplicity (in terms of equipment configuration). In some embodiments, the depolymerization step / zone 30 may be operated at the boiling point of the lowest-boiling component of the reaction mixture at ambient pressure. In other embodiments, the depolymerization reaction may be carried out under elevated pressure, particularly when lower carbon number alcohols are utilized, in order to maximize reaction rate and increase the boiling point of the entire reaction mixture.

[0071] In some embodiments, the depolymerization reaction may be performed at a pressure of atmospheric, or up to a pressure of about 500 psi gauge (psig), up to a pressure of about 250 psig, up to a pressure of about 100 psig, up to a pressure of about 50 psig, or from about 1 to about 25 psig. The depolymerization reaction can be carried out for a reaction time period of from about 5 minutes to about 24 hours, about 30 minutes to about 12 hours, or about 2 hours to about 10 hours, or about 3 hours to about 8 hours.

[0072] When the depolymerization step / zone 30 includes a transesterification step following the initial depolymerization step, the transesterification step can be performed at an average temperature of at least about 25, at least about 30, at least about 35, at least about 40, at least about 45, or at least about 50°C and / or not more than about 85, not more than about 80, not more than about 75, not more than about 70, not more than about 65, not more than about 60, not more than about 55, or not more than about 50°C and / or at an average internal pressure of from about 0 to about 1 MPa (gauge), about 0 to about 0.5 MPa, or about 0.1 to about 0.25 MPa, or it may be slightly below atmospheric pressure. The transesterification step can be carried out for a time period of from about 1 to about 16 hours, about 1.5 to about 12 hours, or about 4 to about 10 hours, and it may include a single stage, or multiple stages performed under different reaction conditions. The alcohol used in the transesterification reaction or step can comprise a C1 to C3 alcohol, or it can comprise or be methanol. When methanol is used, the resulting terephthalate recovered can be dimethyl terephthalate (DMT).

[0073] The depolymerization (and optionally transesterification) reaction performed in depolymerization step / zone 30 may be carried out in the presence of at least one esterification or transesterification catalyst (also referred to herein as the “depolymerization catalyst”) introduced into the depolymerization step / zone 30 in line 114 as shown in FIG. 1. Examples of suitable depolymerization catalysts can include, but are not limited to, metal Ci-C14 alkoxides, metal carbonates, metal acetates, and metal hydroxides, wherein the metals can be chosen from lithium, sodium, potassium, titanium, or tin. In some embodiments, the depolymerization catalysts used in the step / zone 30 can be chosen from sodium hydroxide, potassium hydroxide, sodium methoxide, potassium methoxide, sodium 2-ethylhexylate, potassium 2-ethylhexylate, potassium carbonate, potassium bicarbonate, potassium acetate, sodium acetate, tin oxalate, monobutyltin oxide, monobutyltin tris(2-ethylhexanoate), titanium tetra(isopropoxide), or combinations thereof.

[0074] In some embodiments, the depolymerization catalyst may be present in an amount of at least about 0.001 , at least about 0.005, at least about 0.0075, at least about 0.010 equivalents and / or not more than about 0.10, not more than about 0.075, or not more than about 0.05 equivalents based on a PET repeat unit in the reaction mixture. However, there may be little, or no, enzymes used during depolymerization, such that the total enzyme content of the depolymerization reaction mixture can be less than about 500, less than about 100, less than about 50, or less than about 25 ppm, based on the total weight of the reaction mixture.

[0075] After depolymerization (and optionally, transesterification), the resulting recycled content ethylene glycol (r-EG) and recycled content dimethyl terephthalate (r-DMT) can be recovered by various separation steps or processes to provide purified recycled content products. In particular, as shown in FIG. 1, a depolymerization product stream in line 118 exiting the depolymerization step / zone 30 may be introduced into a separation step or zone 40, wherein the r-DMT and r-EG may be separated into a light organics stream in line 134 and a heavy organics stream in line 122. Any suitable separation method or methods may be used including, for example, distillation, extraction, filtration, decantation, and combinations thereof.

[0076] In some embodiments, the light organics stream, which comprises predominantly methanol (or other alcohol solvent) and recycled content ethylene glycol (r-EG), may be introduced into an EG processing step / zone 60, wherein it may be separated subjected to one or more processing steps to provide a purified r-EG product stream in line 136. Such processing steps may include one or more types of liquid-liquid and / or liquid-vapor separation, such as, for example, distillation, extraction, decantation, and combinations thereof. In some embodiments, the purified r-EG stream comprises at least about 85, at least about 90, at least about 95, at least about 97, at least about 98, at least about 98.5, or at least about 99 weight percent of r-EG, based on the total weight of the stream. The purified r-EG stream in line 136 may be subsequently used as a feedstock for one or more additional processing steps (not shown), including, for example, for the formation of recycled content polyesters as described in further detail herein with respect to FIG. 4.

[0077] Referring again to FIG. 1 , the heavy organics stream in line 122, which includes predominantly r-DMT and methanol, along with lesser amounts of r-EG and various terephthalyl species such as mixed esters, half-esters, oligomers, etc., can be introduced into a DMT processing step or zone 50. In some embodiments, the heavy organics stream in line 122 may comprise r-DMT in an amount of at least about 10, at least about 15, at least about 20, at least about 25, or at least about 30 weight percent and / or not more than about 80, not more than about 75, not more than about 70, not more than about 65, not more than about 60, not more than about 55, not more than about 50, not more than about 45, not more than about 40, not more than about 35, or not more than 30 weight percent, based on the total weight of the stream. The amount of methanol in the heavy organics stream in line 122 introduced into the DMT processing step / zone 50 can be at least about 10, at least about 15, at least about 20, at least about 25, or at least about 30 weight percent and / or not more than about 75, not more than about 70, not more than about 65, not more than about 60, or not more than about 55 weight percent, based on the total weight of the stream.

[0078] Turning now to FIG. 2, a schematic flow diagram of the major steps of an exemplary DMT processing step / zone 150 is provided. As shownin FIG. 2, the heavy organics stream introduced into the r-DMT processing step / zone 150 in line 122 (also referred to as a terephthalate-containing depolymerization stream) may be introduced into a crystallization step or zone 52, wherein at least a portion of the r-DMT may be crystallized to form a crystallized crude r-DMT (also referred to as crude r-DMT solids) stream in line 124. The solid phase formed during the crystallization step comprise predominantly r-DMT, but may also include one or more non-DMT impurities.

[0079] The terephthalate-containing depolymerization stream in line 122 introduced into the crystallization step / zone 52 can comprise r-DMT and methanol. In some embodiments, the amount of r-DMT in the feed stream in line 122 may be in the range of from about 10 to about 60 weight percent, about 15 to about 50 weight percent, or about 15 to about 40 weight percent, based on the total weight of the stream. As needed, the concentration of r-DMT may be adjusted by adding or removing solvent (e.g., methanol) in order to achieve an r-DMT concentration within this range.

[0080] Once a desired r-DMT concentration has been met, the stream in line 122 may be heated to fully dissolve the r-DMT in the solvent prior to crystallization. In some embodiments, the stream may be heated to achieve an average temperature of at least about 60, at least about 65, at least about 70, at least about 75, at least about 80, or at least about 85°C and / or not more than about 150, not more than about 145, not more than about 140, not more than about 135, not more than about 130, not more than about 125, not more than about 120, not more than about 115, not more than about 110, or not more than about 100°C. In other embodiments, no heating step is performed prior to crystallization.

[0081] The resulting r-DMT solution may then be cooled to a crystallization temperature of at least about 10, at least about 15, at least about 20, or at least about 22°C and / or not more than about 55, not more than about 50, not more than about 45, not more than about 40, not more than about 35, not more than about 30, or not more than about 27°C, thereby causing at least a portion (or a major portion) of the dissolved r-DMT to crystallize and precipitate out of solution. The solution may be maintained at the crystallization temperature for at least about 30 minutes, at least about 1 hour, at least about 2 hours, or at least about 4 hours and / or not more than about 12 hours, notmore than about 10 hours, not more than about 8 hours, or not more than about 6 hours and / or until at least about 85, at least about 90, at least about 95, or at least about 97 percent by weight of the total r-DMT introduced into the crystallization step / zone 52 has precipitated out of solution.

[0082] The resulting two-phase mixture can then be subjected to a solid-liquid separation step, wherein the crystallized r-DMT solids may be removed from the liquid phase, which comprises mainly methanol along with some trace amounts of other alcohols, diols, and various soluble non-DMT impurities. Any suitable solid-liquid separation step / zone may be used including, for example, a filter, a centrifuge, a decanter, and combinations thereof. Optionally, the resulting crude r-DMT solids stream may reslurried with additional solvent (e.g., methanol) and another heating step can be performed to provide an r-DMT solution having a concentration within the above ranges. Thereafter, the above cooling and separation steps may again be performed to provide crystallized crude r-DMT including lower levels of non-DMT impurities. When performed, the recrystallization step may be carried out a total of 1 to 5 times, 1 to 4 times, 2 to 4 times, or 1 to 3 times.

[0083] The crude r-DMT solids recovered after crystallization in the crystallization step / zone 52 can comprise DMT in an amount of at least about 60, at least about 65, at least about 70, or at least about 75 weight percent and / or not more than about 95, not more than about 93, not more than about 90, not more than about 85, not more than about 80, or not more than about 75 weight percent, based on the total weight of the stream. In some embodiments, the crude r-DMT solids (also referred to as the crude r-DMT filter cake) can include methanol in an amount of at least about 1 , at least about 2, at least about 5, at least about 7, or at least about 10 weight percent and / or not more than about 30, not more than about 25, not more than about 20, or not more than about 15 weight percent, based on the total weight of the stream.

[0084] Additionally, in some embodiments, the crude r-DMT solids can include one or more recycled content diols (e.g., r-CHDM or r-DEG) and / or one or more recycled content diesters (e.g., r-dimethyl isophthalate) depending on the specific composition of the PET depolymerized upstream. These recycled content comonomers (r-comonomers) may optionally be present in an amount of at least about 0.001 , at least about 0.01 , at least about 0.05, at least about0.10, at least about 0.50, at least about 1, or at least about 2 weight percent and / or not more than about 5, not more than about 3, not more than about 2, not more than about 1.5, not more than about 1, or not more than about 0.5 weight percent, based on the total weight of the stream.

[0085] As shown in FIG. 2, the resulting crude r-DMT solids stream in crystallization step / zone 52 may optionally be washed with at least one solvent in line 123 to remove additional non-DMT impurities remaining after crystallization. Washing differs from recrystallization in that, during washing, at least about 99 percent of the total weight of r-DMT remains in solid form, whereas during recrystallization, at least this much r-DMT is dissolved. The average temperature of the solvent added to r-DMT solids during washing can be at least about 25, at least about 30, at least about 35, or at least about 40°C and / or not more than about 65, not more than about 60, not more than about 55, not more than about 50, or not more than about 45°C.

[0086] The solvent selected for the washing step can be one capable of removing residual alcohol and / or diol (e.g., methanol and / or EG) or other non-DMT impurities from the crude r-DMT solids. Examples of suitable solvents can include, but are not limited to C1 to C14 alcohols, C1 to C6 alcohols, or C1 to C3 alcohols, such as methanol. In some embodiments, the wash solvent may be the same as the crystallization solvent, while, in some embodiments, the two solvents may be different. The wash step may optionally be performed under agitation, and can be carried out for a total time of at least about 5, at least about 10, at least about 30, or at least about 45 seconds and / or not more than about 2 hours, not more than about 1 hour, not more than about 30 minutes, or not more than about 15 minutes before the liquid phase is removed to provide the washed r-DMT solids. Additional wash steps can be performed, as needed, to achieve a desired impurity level in the final r-DMT. In some embodiments, the total number of wash steps performed in the crystallization step / zone 52 can be in the range of from 1 to 10, from 1 to 8, from 1 to 6, from 1 to 5, from 2 to 6, from 2 to 4, or from 1 to 3. Each time, the mass ratio of solvent to r-DMT can be in the range of from about 1 : 1 to about 10: 1 , from about 1.1:1 to about 7:1, about 1.25:1 to about 5:1, or about 1.5:1 to about 3:1.

[0087] The resulting washed crude r-DMT solids stream (also referred to as the crystallized crude r-DMT) exiting the crystallization step / zone 52 inline 124 in FIG. 2 can comprise at least about 75, at least about 80, at least about 85, at least about 88, or at least about 90 weight percent and / or not more than about 99, not more than about 97, not more than about 95, not more than about 92, or not more than about 90 weight percent DMT, based on the total weight of the stream. Additionally, in some embodiments, the crude r-DMT solids stream in line 124 can comprise methanol in an amount of greater than 0, or at least about 1 , at least about 2, at least about 5, at least about 7, or at least about 10 weight percent and / or not more than about 25, not more than about 20, not more than about 15, not more than about 10, or not more than about 5 weight percent, based on the total weight of the stream.

[0088] In some embodiments, the crude r-DMT solids stream in line 124 may comprise free ethylene glycol in an amount of less than about 10, less than about 5, less than about 2, less than about 1 , less than about 0.5, or less than about 0.025 weight percent, or from about 0.001 to about 0.25 weight percent, or from about 0.005 to about 0.10 weight percent, from about 0.01 to about 0.05, or from about 0.01 to about 0.025 weight percent, based on the total weight of the stream. Any residual recycled content comonomers can be present in even lower amounts, such as, for example, from about 0.5 to about 500 parts per million by weight (ppm), from about 1 to about 250 ppm, from about 1.5 to about 100 ppm, about 2 to about 50 ppm, or about 5 to about 25 ppm, based on the total weight of the stream.

[0089] As shown in FIG. 2, at least a portion of the crude r-DMT solids stream in line 124 can be introduced into a melting step / zone 54, wherein the solids can be heated to form a stream of molten crude r-DMT comprising mostly r-DMT and some trace amounts of non-DMT impurities. During the melting step, the crude r-DMT solids may be heated, optionally in an agitated vessel such as a rotary drum or a stirred tank, to a temperature of at least about 140, at least about 145, at least about 150, at least about 155, or at least about 160°C and / or not more than about 210, not more than about 205, not more than about 200, not more than about 195, not more than about 190, nor more than about 185, not more than about 180, or not more than about 175°C.

[0090] Additionally, during the melting step, the pressure may be maintained between about 0 and about 5 psi, between about 0 and about 3 psi, between about 0.1 and about 2 psi, or about 0.25 and about 2 psi. In someembodiments, the melting zone includes a vapor recovery system for removing a vapor stream comprising residual ethylene glycol, residual methanol, and other volatile components that may evolve from the melt phase during heating via line 125. The molten r-DMT exiting the melting step / zone 54 via line 126 may be in the liquid phase, and can have a total solids content of not more than about 1, not more than about 0.5, not more than about 0.25, or not more than about 0.10 weight percent, based on the total weight of the stream.

[0091] The molten crude r-DMT stream exiting the melting step / zone 54 in line 126 shown in FIG. 2 includes a similar concentration of DMT as the feed to this step / zone, but may comprise lower concentrations of non-DMT impurities, particularly more volatile impurities such as ethylene glycol and methanol. For example, in some embodiments, the molten r-DMT stream in line 126 can include about 0 ppm or about 0 weight percent methanol, or it may include methanol in an amount of greater than 0 ppm, or at least about 25 at least about 100, at least about 500, at least about 750, or at least about 1000 ppmw and / or not more than about 10, not more than about 7, not more than about 5, not more than about 3, not more than about 2, not more than about 1 , not more than about 0.5, not more than about 0.25, or not more than about 0.1 weight percent, based on the total weight of the stream.

[0092] In some embodiments, the molten crude r-DMT stream in line 126 can comprise methanol in an amount of greater than 0, at least about 5, at least about 10, at least about 15, at least about 20, at least about 25, at least about 30, at least about 35, at least about 40, at least about 45, at least about 50, at least about 55 ppm and / or not more than about 200, not more than about 150, not more than about 100, not more than about 90, not more than about 75, not more than about 70, not more than about 65, not more than about 60, not more than about 55, not more than about 50, not more than about 45, not more than about 40, or not more than about 35 ppm, based on the total weight of the crude r-DMT stream.

[0093] Further, the molten crude r-DMT stream in line 126 may include one or more impurities formed during its upstream processing (e.g., depolymerization, crystallization, washing, and / or melting) and it may not include certain chemical components typically found in virgin DMT prepared by conventional reaction pathways. For example, in some embodiments, themolten crude r-DMT in line 126 may include bis(2-hydroxyethyl)terephthalate (BHET) in an amount of at least about 1 , at least about 10, at least about 50, at least about 100, at least about 200, at least about 250, at least about 500, at least about 750, at least about 1000, at least about 2500, or at least about 5000 ppm and / or not more than about 10, not more than about 7, not more than about 5, not more than about 2.5, not more than about 1 weight percent or not more than about 5000, not more than about 1000, not more than about 750, not more than about 500, not more than about 250, or not more than about 100 ppm, based on the total weight of the stream. In some embodiments, the molten crude r-DMT in line 126 may comprise less than about 25, less than about 20, less than about 15, less than about 10, less than about 5, less than about 2, or less than about 1 ppm of BHET, based on the total weight of the stream.

[0094] Additionally, or in the alternative, the molten crude r-DMT in line 126 may include mono(2-hydroxyethyl)terephthalate (MHET) in an amount of at least about 1 , at least about 10, at least about 50, at least about 100, at least about 200, at least about 250, at least about 500, at least about 750, at least about 1000, at least about 2500, or at least about 5000 ppm and / or not more than about 10, not more than about 7, not more than about 5, not more than about 2.5, not more than about 1 weight percent or not more than about 5000, not more than about 1000, not more than about 750, not more than about 500, not more than about 250, or not more than about 100 ppm, based on the total weight of the stream.

[0095] In some embodiments, the molten crude r-DMT in line 126 can comprise at least 700, at least about 750, at least about 800, at least about 850, at least about 900, at least about 1000, at least about 1250, at least about 1500, at least about 1750, at least about 2000, at least about 2500, or at least about 2750 ppm and / or not more than about 5000, not more than about 4500, not more than about 4000, not more than about 3500, not more than about 3000, or not more than about 2500 ppm of MHET, based on the total weight of the stream.

[0096] In some embodiments, the molten crude r-DMT in line 126 comprises free ethylene glycol (free EG) in an amount of greater than 0 ppm or at least about 10, at least about 25, at least about 50, at least about 100, at least about 200, at least about 300, at least about 400, or at least about 500ppm and / or not more than about 5, not more than about 3, not more than about 2, not more than about 1.5, not more than about 1 , or not more than about 0.75 weight percent, based on the total weight of the stream. In some embodiments, the molten crude r-DMT in line 126 comprises at least about 100, at least about 200, at least about 300, at least about 400, at least about 500, at least about 600, or at least about 700 ppm and / or not more than about 5, not more than about 4.5, not more than about 4, not more than about 3.5, not more than about 3, not more than about 2.5, not more than about 2, not more than about 1.5, not more than about 1, not more than about 0.5, not more than about 0.35, or not more than about 0.25 weight percent, based on the total weight of the stream.

[0097] In some embodiments, the total ethylene glycol (total EG) content can be at least about 100, at least about 200, at least about 300, at least about 400, at least about 500, at least about 600, or at least about 700 ppm and / or not more than about 5, not more than about 4.5, not more than about 4, not more than about 3.5, not more than about 3, not more than about 2.5, not more than about 2, not more than about 1.5, not more than about 1, not more than about 0.5, not more than about 0.35, or not more than about 0.25 weight percent, based on the total weight of the stream. Total ethylene glycol is measured by adding the amount of free EG to the amount of EG present in any EG-containing impurities, including BHET and MHET, present in the stream, and can be determined by GC-FID.

[0098] In some embodiments, the molten crude r-DMT in line 126 may comprise methyl hydrogen terephthalate (MHT) in an amount of at least about 100, at least about 250, at least about 500, at least about 750, at least about 1000, at least about 1500, at least about 2000, at least about 2500, at least about 3000, at least about 3500, or at least about 5000 ppm and / or not more than about 1 weight percent, or not more than about 7500, not more (or less than) than about 5000, not more than about 3500, not more than about 3000, or not more than about 2500 ppm, based on the total weight of the stream. In some embodiments, the molten crude r-DMT stream in line 126 may comprise at least about 1, at least about 5, at least about 10, or at least about 25 ppm and / or not more than about 450, not more than about 400, not more than about 350, not more than about 300, not more than about 250, not more than about200, not more than about 150, not more than about 100, or not more than about 75 ppm of dimethyl isophthalate (DMI).

[0099] In some embodiments, the molten crude r-DMT may comprise MHT in an amount of at least about 500, at least about 550, at least about 600, at least about 650, at least about 700, at least about 750, at least about 1000, at least about 1100, at least about 1200, at least about 1300, or at least about 1400 ppm and / or not more than about 2000, not more than about 1750, not more than about 1500, or not more than about 1250 ppm, based on the total weight of the stream.

[0100] Further, in some embodiments, the molten crude r-DMT in line 126 may comprise methyl formyl benzoate (MFB) in an amount of 0 ppm or in an amount of less than about 7, less than about 6, less than about 5, less than about 4, less than about 3, less than about 2, or less than about 1 , less than about 0.5, or less than about 0.25 ppm, based on the total weight of the stream.

[0101] The molten crude r-DMT in line 126 may comprise similar amounts of dimethyl phthalate (DMP) such as amount of 0 ppm or an amount of less than about 1, less than about 0.5, or less than about 0.25 ppm, based on the total weight of the stream. Unless otherwise noted, the amounts of each of the above components in the r-DMT can be determined using HPLC. In some embodiments, the molten crude r-DMT can comprise DMP in an amount of at least about 20, at least about 25, at least about 30, at least about 35, at least about 40, at least about 45, at least about 50, at least about 60, at least about 70, at least about 80, at least about 90, at least about 100, at least about 125, at least about 150, or at least about 175 ppm and / or not more than about 250, not more than about 200, not more than about 175, not more than about 150, not more than about 125, not more than about 100, not more than about 75, or not more than about 50 ppm, based on the total weight of the stream.

[0102] According to some embodiments, the molten crude r-DMT stream in line 126 may comprise residual elemental antimony in an amount of at least about 1 , at least about 2.5, at least about 5, at least about 10, at least about 25, at least about 50, at least about 75, at least about 100, at least about 125, or at least about 150 ppm and / or not more than about 350, not more than about 300, not more than about 200, or not more than about 100 ppm, basedon the total weight of the stream. Antimony content of the r-DMT can be measured using ICP-MS after full digestion in a strong acid.

[0103] In some embodiments, the molten crude r-DMT stream in line 126 can include at least about 350, at least about 400, at least about 450, at least about 500, at least about 750, a least about 1000, or at least about 1250 parts per billion by weight (ppb) and / or not more than about 5000, not more than about 4500, not more than about 4000, not more than about 3500, not more than about 3000, not more than about 2500, or not more than about 2000 ppb of elemental antimony, based on the total weight of the r-DMT stream.

[0104] In some embodiments, the molten crude r-DMT stream in line 126 can comprise less than about 5, less than about 4, less than about 3, less than about 2, less than about 1, or less than about 0 ppm of total Silver. Additionally, or in the alternative, the molten crude r-DMT stream in line 126 can comprise less than about 100, less than about 70, less than about 50, less than about 25, less than about 10, less than about 5, less than about 2, or less than about 1, or about 0 ppm of polysaccharides or remnants thereof, such as one or more amino acids including, but not limited to, glycine, proline, and 4-hydroxyproline.

[0105] In some embodiments, the molten crude r-DMT stream in line 126 can comprise an oligomer of r-DMT and EG having 3 or more total monomer units (e.g., DMT-EG-DMT), or from 4 to 20, from 5 to 15, or from 5 to 10 monomer units. Such an oligomer may be present in an amount of less than about 100, less than about 75, less than about 50, less than about 25, less than about 10, less than about 5, less than about 2, or less than about 1 ppm, based on the total weight of the stream. In some embodiments, the molten crude r-DMT stream in line 126 may include no r-DMT / EG oligomer (e.g., about 0 ppm, based on the total weight of the stream).

[0106] As shown in FIG. 2, the crude molten r-DMT stream in line 126 may be introduced into a purification zone 56, wherein further impurities are removed via line 130 to provide a stream of highly purified r-DMT in line 128 and a DMT-depleted stream in line 130. The purification step / zone 56 can include any suitable type of separation step including, but not limited to, distillation, extraction, crystallization, washing, and various combinations of the foregoing. In some embodiments, the recovery percentage of DMT in thepurified r-DMT stream exiting the purification step / zone 56 can be from about 50 to about 99.9, from about 75 to about 99.5, from about 80 to about 99, from about 85 to about 97, from about 87 to about 95, or about 90 to about 95 percent. As used herein, the term “recovery percentage (of component A)” in a specific product stream exiting a given process step / zone is defined by the following formula: (Mass of component A in the specific product stream) I (Combined mass of component A introduced into the given process step in all streams), expressed as a percentage. Note that ppm may also be used in this formula with use of the same sample size.

[0107] Additionally, the purified r-DMT stream in line 128 may exhibit a substantial reduction of the amount one or more impurities introduced into the purification step / zone 56 by the molten crude r-DMT stream in line 126. For example, in some embodiments, the recovery percentage of one or more of methanol, BHET, MHET, free EG, MHT, and elemental antimony in the purified r-DMT stream can be less than about 50, not more than about 45, not more than about 40, not more than about 35, not more than about 30, not more than about 25, not more than about 20, or not more than about 15 percent and / or at least about 1, at least about 2, or at least about 5 percent. In some embodiments, the percent recovery of one or more of these components can be less than about 5, less than about 4, less than about 3, less than about 2, less than about 1, or about 0 percent, calculated according to the above formula. Thus, the purified r-DMT stream in line 128 may include significantly lower amount of one or more (or all) of these impurities as compared to other recycled content DMT.

[0108] According to some embodiments, the purification step or zone 56 may reduce the amount of elemental antimony in purified r-DMT stream by at least about 80, at least about 85, at least about 90, at least about 92, at least about 95, at least about 97, at least about 98, or at least about 99 percent, wherein the percent reduction is calculated by (amount of Sb in the crude molten r-DMT - amount of Sb in the purified r-DMT) I (amount of Sb in the crude molten r-DMT), expressed as a percentage and wherein the amount can be in ppm or grams. For example, in some embodiments, the purification step / zone 56 may reduce the amount of elemental antimony in the crude molten r-DMT stream from at least about 250, at least about 300, at least about 350, at leastabout 400, at least about 450, or at least about 500 ppb and / or not more than about 2000, not more than about 1750, not more than about 1500, or not more than about 1250 ppb to an amount of at least about 2, at least about 5, at least bout 7 and / or not more than about 40, not more than about 35, not more than about 30, or not more than about 27 ppb.

[0109] Turning now to FIGS. 3a and 3b, schematic flow diagrams of the main steps of purification steps or zones 156 configured according to embodiments of the present technology are provided. FIG. 3a illustrates embodiments of a purification step / zone 156 that comprises a solvent contact stage or vessel 160, while FIG. 3b shows a purification step / zone 156 that includes a distillation column 166.

[0110] Referring initially to FIG. 3a, the purification step / zone 156 illustrated therein includes a solvent contact stage / vessel 160, for removing at least a portion of the impurities in the crude molten r-DMT stream in line 126 via contact with one or more solvents. In some embodiments, the solvent contact stage / vessel 160 may comprise a crystallization stage or vessel, while in other embodiments, the solvent contact stage / vessel 160 may comprise a wash stage or vessel. In some embodiments, the solvent contact stage / vessel 160 may include both crystallization and washing. Solvent introduced into the stage / vessel 160 via line 127 can include, but is not limited to, one or more C1 to C14 alcohols, C2 to C14 diols, and combinations thereof. In some embodiments, the solvent can comprise, consist of, or consist essentially of, methanol.

[0111] In some embodiments when the solvent contact stage / vessel 160 comprises a crystallization stage / vessel, the solvent added via line 127 may be used to dissolve the crude molten r-DMT. The solvent can be heated and may have a temperature of, for example, at least about 25, at least about 30, at least about 35, or at least about 40°C and / or not more than about 65, not more than about 60, not more than about 55, not more than about 50, or not more than about 45°C. Once dissolved, the r-DMT solution may be cooled to a crystallization temperature of at least about 10, at least about 15, at least about 20, or at least about 22°C and / or not more than about 55, not more than about 50, not more than about 45, not more than about 40, not more than about 35, not more than about 30, or not more than about 27°C.

[0112] According to some embodiments, the time period for each crystallization step performed in purification step / zone 156 may be longer than the time period for crystallization in the upstream crystallization step / zone 52 described with respect to FIG. 2. For example, in some embodiments, when used in purification step / zone 156, the crystallization time (e.g., where the solution is held at a crystallization temperature to precipitate solid r-DMT) can be at least about 2, at least about 4, at least about 6, at least about 8, at least about 10, at least about 12, at least about 15, at least about 18, or at least about 20 hours and / or not more than about 48, not more than about 40, not more than about 35, not more than about 30, or not more than about 24 hours. In some cases, the temperature and / or pressure of the crystallization in purification step / zone 156 may be adjusted slightly from the temperature and / or pressure utilized in the crystallization step / zone 52 in order to slow the crystallization rate and increase the purity of the r-DMT solids.

[0113] After completion of the crystallization step (or steps) in stage / vessel 160, the resulting two-phase mixture of purified r-DMT solids and DMT-depleted liquid may be subjected to a solid-liquid separation step to recover the purified r-DMT solids. The resulting solids can optionally be reslumed with additional solvent and recrystallized and / or washed as discussed previously before removing the solids as the purified r-DMT product stream in line 128.

[0114] According to some embodiments, the solvent contact stage / vessel 160 illustrated in FIG. 3a may comprise a solvent wash zone for removing one or more of the non-DMT impurities from the crude molten r-DMT in line 126. Unlike crystallization where the r-DMT is dissolved into solution, the wash step, when used, may be carried out such that less than 1 weight percent of the initial mass of r-DMT is dissolved during contact. The temperature of the solvent introduced into each individual wash step in solvent contact stage / vessel 160 can be at least about 10, at least about 15, at least about 20, at least about 25, or at least about 30°C and / or not more than about 45, not more than about 40, not more than about 35, not more than about 30, or not more than about 27°C. Multiple wash steps may also be used in order to achieve the desired level of impurity removal. When multiple wash steps are used, the solvent used in each step may be the same as, or different than, thesolvent used in one or more other wash steps. In some embodiments, one or more wash steps may be performed after a crystallization step, while in other embodiments, the wash step or step may be performed without any preceding crystallization.

[0115] After the purification step (e.g., crystallization and / or washing) is completed, the liquid phase can be removed from the solvent contact stage / vessel 160 via line 134, as generally shown in FIG. 3a, before being purified in a separation stage or vessel 162. In some embodiments, at least a portion of the resulting purified solvent in line 136 may be reintroduced into the solvent contact stage / vessel 160 via line 136a, or all or a portion may be returned to a different location within the chemical recycling (or another) facility for further transportation, storage, and / or use (embodiment not shown in FIG.3a). The heavy, non-DMT impurities removed from the solvent in line 134 may be withdrawn from the separation stage / vessel 162 and can be routed out of the purification step / zone 156 via line 130.

[0116] Turning now to FIG. 3b, a purification step / zone 156 configured according to other embodiments of the present technology that includes at least one distillation column 166 for purifying the crude r-DMT is illustrated. Although shown as a single distillation column in FIG. 3b, two or more columns may be used, arranged in series or in parallel, to perform the purification step described herein. In some embodiments, the distillation column 166 may be a conventional vapor-liquid distillation column, while, in other embodiments, the distillation column 166 may be a reactive distillation column, which utilizes a catalyst to facilitate reaction between two or more components in the column, thereby increasing separation efficiency.

[0117] In operation, the distillation column 166 can have an average overhead temperature, measured at the overhead vapor take off location, of at least about 150, at least about 155, at least about 160, at least about 165, at least about 170, at least about 175, or at least about 180°C and / or not more than about 225, not more than about 220, not more than about 215, not more than about 210, not more than about 205, not more than about 200, nor more than about 195, or not more than about 190°C, while the average bottoms temperature, measured at the liquid bottoms take off location, can be at least about 190, at least about 195, at least about 200, at least about 205, at leastabout 210, at least about 215, or at least about 220°C and / or not more than about 260, not more than about 255, not more than about 250, not more than about 245, not more than about 240, not more than about 235, or not more than about 230°C.

[0118] The overhead pressure of the distillation column 166, measured at the same location, can be less than about 760, less than about 400, less than about 350, less than about 300, or less than about 250 mm Hg or it can be at least about 5, at least about 10, at least about 15, at least about 20, at least about 25, at least about 30, or at least about 35 mm Hg and / or not more than about 200, not more than about 150, not more than about 125, not more than about 100, or not more than about 75 mm Hg. In some embodiments, the distillation column 166 can be operated with a reflux ratio of at least about 0.1 , at least about 0.2, at least about 0.25, or at least about 0.30 and / or not more than about 3, not more than about 2.5, not more than about 2, not more than about 1.5, or not more than about 1.

[0119] In some embodiments, the distillation column 166 can have at least about 5, at least about 6, at least about 8, at least about 10, or at least about 15 theoretical distillation stages, and / or it may include not more than about 35, not more than about 30, not more than about 25, not more than about 20, or not more than about 18 theoretical stages, calculated according to the McCabe-Thiele method. However, in other embodiments, the distillation column 166 may have far fewer stages such as, for example, less than about 5, less than about 4, less than about 3, or even 2 or fewer theoretical stages. The overhead vapor stream withdrawn from the distillation column 166 in line 128 may comprise the purified r-DMT stream, while the impurities and other heavy components (e.g., residual catalyst) can be removed in the bottoms liquid stream in line 130.

[0120] When the distillation column 166 comprises a reactive distillation column, a catalyst-containing stream from a catalyst source 164 may be combined with at least a portion of the molten crude r-DMT just prior to and / or within the column 166. In some embodiments, the catalyst stream may be combined with the molten crude r-DMT at one or more locations upstream of the column 166 and downstream of the crystallization step / zone (not shown in FIG. 3b), such that the combined catalyst-containing r-DMT stream may beintroduced into the feed inlet of the reactive distillation column 166. In some embodiments (not shown in FIG. 3b), the combined stream may be stored in a tank or other holding vessel for a time period of at least about 15, at least about 30, at least about 45, or at least about 60 minutes and / or not more than about 2.5, not more than about 2, not more than about 1.5 hours, or not more than 1 hour before being fed into the column 166. According to some embodiments, the catalyst-containing stream may be combined with the crude r-DMT in the melting step or zone (not shown in FIG. 3b) and the combined stream may then be introduced into the distillation column 166 in the purification step / zone 156 illustrated in FIG. 3b.

[0121] In some embodiments, at least a portion of the catalystcontaining stream and the molten crude r-DMT stream in line 126 may be introduced into the distillation column 166 simultaneously so that the catalyst combines with the r-DMT stream inside the column. In some cases, the catalyst-containing stream may be introduced at a higher vertical elevation than the molten crude r-DMT, while in other cases, the catalyst-containing stream may enter at a lower vertical elevation than the crude r-DMT.

[0122] The catalyst-containing stream combined with the r-DMT may include at least one catalyst dispersed or dissolved in one or more solvents. Examples of suitable catalysts can include, but are not limited to, one or more of titanium oxides, tin (II) to (IV) esters, alkali metals, alkaline earth metals (e.g., Li and Ca), manganese compounds, zinc compounds, magnesium acetates or benzoates, or combinations of the foregoing. Suitable solvents can include, for example, C1 to C14 alcohols and C2 to C14 diols. In some embodiments, the solvent can be or comprise methanol. The catalyst may be present in the catalyst containing stream in an amount of at least about 0.01 , at least about 0.02, at least about 0.025, or at least about 0.03 weight percent and / or not more than about 1, not more than about 0.75, not more than about 0.50, not more than about 0.25, not more than about 0.10, or not more than about 0.05 weight percent, based on the total weight of the catalyst-containing stream.

[0123] Upon combination with the molten crude r-DMT stream, the total amount of catalyst present in the combined stream can be at least about 5, at least about 10, at least about 20, at least about 25, at least about 30, at least about 35, at least about 50, at least about 75, at least about 100, or at leastabout 250 ppm and / or not more than about 1000, not more than about 750, not more than about 500, not more than about 300, not more than about 200, not more than about 100, or not more than about 50 ppm, based on the total weight of the combined stream.

[0124] Referring again to FIG. 2, the r-DMT depleted stream withdrawn from the purification step / zone 56 in line 130 may comprise a majority of the non-DMT impurities introduced into the purification step / zone 56, along with a small amount of r-DMT. For example, in some embodiments, the DMT-depleted stream in line 130 may comprise at least about 10, at least about 50, at least about 100, at least about 500, at least about 1000, or at least about 5000 ppm, or at least about 1 , at least about 1.5, or at least about 2 weight percent and / or not more than about 10, not more than about 7, not more than about 5, not more than about 3, not more than about 2, not more than about 1.5, or not more than 1 weight percent DMT. Additionally, the stream in line 130 may also include 0 ppm or less than about 1 , less than about 0.5, or less than about 0.25 ppm of MFB and / or DMP, particularly since little or none of either of these components may be present in the feed to the purification step / zone 56.

[0125] Additionally, in some embodiments, the r-DMT depleted stream in line 130 may further comprise an oligomer of DMT and EG (e.g., DMT-EG oligomer) having 3 or more total monomer units (e.g., DMT-EG-DMT), or from 4 to 20, from 5 to 15, or from 5 to 10 monomer units. Such an oligomer may be present in an amount of at least about 1, at least about 2, at least about 5, at least about 10, at least about 15, at least about 20, at least about 25, at least about 50, at least about 75, or at least about 100 ppm and / or not more than about 2500, not more than about 2000, not more than about 1500, not more than about 1000, not more than about 750, not more than abut 500, or not more than about 250 ppm of the above DMT-EG oligomer based on the weight of the stream.

[0126] In some embodiments, the r-DMT depleted stream in line 130 can comprise BHET in an amount of at least about 1 , at least about 10, at least about 50, at least about 100, at least about 200, at least about 250, at least about 500, at least about 750, at least about 1000, or at least about 2500 ppm and / or not more than about 10, not more than about 7, not more than about 5, not more than about 2.5, not more than about 1.5, not more than about 1, ornot more than about 0.5 weight percent or not more than about 2500, not more than about 2000, not more than about 1500, not more than about 1000, not more than about 750, or not more than about 500 ppm, based on the total weight of the stream (or composition).

[0127] Additionally, or in the alternative, the r-DMT depleted stream in line 130 can comprise MHET in an amount of at least about 1, at least about 10, at least about 50, at least about 100, at least about 200, at least about 250, at least about 500, at least about 750, at least about 1000, or at least about 2500 ppm and / or not more than about 10, not more than about 7, not more than about 5, not more than about 2.5, not more than about 1.5, not more than about 1 , or not more than about 0.5 weight percent or not more than about 2500, not more than about 2000, not more than about 1500, not more than about 1000, not more than about 750, or not more than about 500 ppm, based on the total weight of the stream (or composition).

[0128] Further, in some embodiments, the r-DMT depleted stream in line 130 can include little or no free ethylene glycol (free EG), such that the total amount is at least about 0.1 , at least about 0.5, at least about 1 , at least about 2, or at least about 5 ppm and / or not more than about 100, not more than about 75, not more than about 50, not more than about 25, not more than about 10, or not more than about 5 ppm of free ethylene glycol, based on the total weight of the stream. In some embodiments, the total ethylene glycol (total EG) in the r-DMT depleted stream can be at least about 10, at least about 25, at least about 50, at least about 75, at least about 100, at least about 150, at least about 200, at least about 500, at least about 750, or at least about 1000 ppm and / or not more than about 25, not more than about 20, not more than about 15, not more than about 10, not more than about 5, not more than about 2, not more than about 1.5, not more than about 1 , not more than about 0.75, not more than about 0.5, not more than about 0.1 , or not more than about 0.05 weight percent, based on the total weight of the stream.

[0129] Additionally, or in the alternative, the r-DMT depleted stream in line 130 may comprise at least about 1, at least about 10, at least about 50, at least about 100, at least about 250, or at least about 500 ppm and / or not more than about 2500, not more than about 2000, not more than about 1500, notmore than about 1000, not more than about 750, or not more than about 500 ppm of MHT, based on the total weight of the stream (or composition).

[0130] The r-DMT depleted stream in line 130 may include a large portion of the elemental antimony introduced into the purification step / zone 56. For example, in some embodiments, the r-DMT depleted stream in line 130 may comprise at least about 300, at least about 350, at least about 400, at least about 500, at least about 750, or at least about 1000 ppm and / or not more than about 1 , not more than about 0.5, or not more than about 0.1 weight percent or not more than about 750, not more than about 500, or not more than about 450 ppm of elemental antimony, based on the total weight of the stream (or composition).

[0131] The purified r-DMT withdrawn from the purification step / zone 56 in line 128 (or a composition derived therefrom) can comprise at least about 95, at least about 97, at least about 97.5, at least about 98, at least about 98.5, at least about 99, at least about 99.5, or at least about 99.9 weight percent and / or about 100 weight percent, or not more than about 99.99, not more than about 99.9, not more than about 99.5, not more than about 99, not more than about 98.5, not more than about 98, or not more than 97.5 weight percent of DMT, based on the total weight of the stream (or composition).

[0132] In some embodiments, the purified r-DMT stream in line 128 (or composition derived therefrom) may comprise an oligomer of r-DMT and EG having 3 or more total monomer units (e.g., DMT-EG-DMT), or from 4 to 20, from 5 to 15, or from 5 to 10 monomer units, in an amount of less than about 10, less than about 5, less than about 2, or less than about 1 ppm, based on the total weight of the stream (or composition), or it may include no (e.g., about 0 ppm) of the oligomer.

[0133] In some embodiments, the purified r-DMT stream in line 128 (or composition derived therefrom) may comprise 0 weight percent (or 0 ppm) or greater than 0 ppm, or at least about 100, at least about 250, at least about 500, at least about 750, at least about 1000 ppm or at least about 0.25, at least about 0.50, or at least about 0.75 weight percent of methanol and / or not more than about 2, not more than about 1.5, not more than about 1 , or not more than about 0.5 weight percent or not more than about 1000, not more than about 750, not more than about 500, not more than about 250, not more than about100, not more than about 95, not more than about 75, not more than about 50, not more than about 25, or not more than about 10 ppm of methanol, based on the total weight of the stream (or composition).

[0134] In some embodiments, the purified r-DMT stream in line 128 (or composition derived therefrom) may comprise greater than 0 ppm, or at least about 1, at least about 10, at least about 50, at least about 100, at least about 200, at least about 250, at least about 500, at least about 750, at least about 1000, at least about 2500, or at least about 5000 ppm and / or not more than about 2.5, not more than about 2, not more than about 1.5, not more than about 1 , not more than about 0.5, or not more than about 0.25 weight percent and / or not more than about 1000, not more than about 750, not more than about 500, not more than about 250, not more than about 100, not more than about 75, not more than about 50, not more than about 25, or not more than about 10 ppm of BHET, based on the total weight of the stream (or composition). In some embodiments, the purified r-DMT stream (or composition derived therefrom) may include 0 ppm or less than about 1 , less than about 0.75, less than about 0.5, less than about 0.25, or less than about 0.10 ppm of BHET, based on the total weight of the stream (or composition).

[0135] In some embodiments, the purified r-DMT stream in line 128 (or composition derived therefrom) may comprise greater than 0 ppm, or at least about 1, at least about 10, at least about 50, at least about 100, at least about 200, at least about 250, at least about 500, at least about 750, at least about 1000, at least about 2500, or at least about 5000 ppm and / or not more than about 2, not more than about 1.5, not more than about 1 , or not more than about 0.5 weight percent or not more than about 2500, not more than about 2250, not more than about 2000, not more than about 1900, not more than about 1850, not more than about 1700, not more than about 1500, not more than about 1250, not more than about 1000, not more than about 750, not more than about 500, not more than about 250, not more than about 100, not more than about 75, not more than about 50, not more than about 25, or not more than about 10 ppm of MHET, based on the total weight of the stream (or composition).

[0136] In some embodiments, the purified r-DMT stream in line 128 (or composition therefrom) can include MHET in an amount less than 700, not more than about 690, not more than about 650, not more than about 600, notmore than about 550, not more than about 500, not more than about 450, not more than about 400, not more than about 350, not more than about 300, not more than about 250, not more than about 200, not more than about 150, not more than about 100, not more than about 75, not more than about 50, not more than about 25, not more than 10, not more than about 5, not more than about 2, or not more than about 1 ppm, based on the total weight of the stream (or composition).

[0137] Additionally, or in the alternative, the purified r-DMT stream in line 128 (or composition therefrom) comprises 0 ppm or less than about 1 , less than about 0.5, or less than about 0.25 ppm of MFB and / or 0 ppm or less than about 1 , less than about 0.5, or less than about 0.25 ppm of DMP, based on the total weight of the stream (or composition). In some embodiments, the purified r-DMT stream in line 128 (or a composition therefrom) can include not more than about 45, not more than about 40, not more than about 35, not more than 30, not more than 25, not more than about 20, or not more than about 15 ppm of DMP, based on the total weight of the composition. Additionally, or in the alternative, the purified r-DMT stream in line 128 (or composition therefrom) can include DMP in an amount of at least about 0.5, at least about 1 , at least about 1.5, at least about 2, at least about 2.5, at least about 3, at least about 3.5, or at least about 4 ppm. Further, in some embodiments, the purified r-DMT stream in line 128 (or a composition therefrom) can comprise MFB in an amount of in an amount of less than 5, less than about 4.5, less than about 4, less than about 3.5, less than about 3, less than about 2.5, less than about 2, less than about 1.5, or less than about 1 ppm, based on the total weight of the purified r-DMT stream in line 128.

[0138] Further, in some embodiments, the purified r-DMT stream in line 128 (or a composition derived therefrom) can comprise 0 ppm or greater than 0 ppm or at least about 1 , at least about 5, at least about 10, or at least about 25, at least about 50, at least about 100, at least about 250, or at least about 500 ppm and / or not more than about 1250, not more than about 1000, not more than about 750, not more than about 500, not more than about 300, not more than about 250, not more than about 200, not more than about 150, not more than about 100, or not more than about 75 ppm of a combined amount ofdimethyl isophthalate (DMI) and / or any modifying diols such as, for example, DEG, NPG, CHDM, etc., based on the weight of the stream (or composition).

[0139] The total amount of MHT in the purified r-DMT stream in line 128 (or a composition derived therefrom) can be greater than 0 ppm, or at least about 1, at least about 25, at least about 50, at least about 75, at least about 100, at least about 250, at least about 500, at least about 750, at least about 1000, at least about 1250, at least about 1500, at least about 1750, or at least about 2000 ppm and / or not more than about 7500, not more than (or less than) about 5000, not more than about 4500, not more than about 4000, not more than about 3500, not more than about 3000, not more than about 2500, not more than about 2000, not more than about 1800, not more than about 1750, not more than about 1500, not more than about 1250, or not more than about 1000 ppm, based on the total weight of the stream (or composition).

[0140] In some embodiments, the purified r-DMT stream in line 128 (or a composition therefrom) can include MHT in an amount of at least 7.5, at least about 10, at least about 12.5, at least about 15, a least about 20, at least about 25, at least about 27, at least about 30, at least about 32, at least about 35, or at least about 37 ppm and / or not more than about 500, not more than about 450, not more than about 400, not more than about 350, not more than about 300, not more than about 250, not more than about 200, not more than about 175, or not more than about 160 ppm, based on the total weight of the stream (or composition).

[0141] In some embodiments, the purified r-DMT stream in line 128 (or a composition derived therefrom) can include 0 ppm or greater than 0 ppm or at least about 0.25, at least about 0.50, at least about 0.75, at least about 1 , at least about 1.5, at least about 2, at least about 2.5, at least about 5, at least about 10, at least about 25, at least about 50, at least about 75, at least about 100, at least about 250, at least about 300, at least about 500, or at least about 1000 ppm, or at least about 0.25, at least about 0.50, at least about 0.75, at least about 1 , at least about 1.5, at least about 2, at least about 2.5 or at least about 5 weight percent of free ethylene glycol, based on the total weight of the stream (or composition).

[0142] Additionally, the purified r-DMT stream in line 128 (or a composition derived therefrom) may comprise less than about 500, less thanabout 300, less than about 250, less than about 200, less than about 150, less than about 100, less than about 95, less than about 90, less than about 75, less than about 50, less than about 25, less than about 10, less than about 5, less than about 2, or less than about 1 ppm of free ethylene glycol, based on the total weight of the stream (or composition). The purified r-DMT stream in line 128 can include at least about 5, at least about 10, at least about 25, at least about 50, at least about 75, or at least about 100 ppm of free EG, based on the total weight of the stream (or composition). The amount of free ethylene glycol can be determined by GC-FID.

[0143] Additionally, or in the alternative, in some embodiments, the total amount, by weight, of free ethylene glycol in the purified r-DMT product stream in line 128 can be at least about 5, at least about 10, at least about 25, at least about 35, at least about 45, at least about 50, at least about 55, at least about 60, at least about 75, at least about 80, at least about 85, at least about 90, or at least about 95 percent lower than the total amount of free ethylene glycol in the molten crude r-DMT stream fed into the purification step / zone 56 in line 126, as determined by the formula: (mass of free EG in the molten crude r-DMT - mass of free EG in purified r-DMT product) I (mass of free EG in molten crude r-DMT), expressed as a percentage.

[0144] In some embodiments, the total ethylene glycol (total EG) content of the purified r-DMT stream in line 128 can be not more than about 500 ppm, or it can be not more than about 450 ppm, not more than about 400 ppm, not more than about 350 ppm, not more than about 300 ppm, not more than about 250 ppm, not more than about 200 ppm, not more than about 150 ppm, not more than about 100 ppm, not more than about 95 ppm, not more than about 75 ppm, not more than about 50 ppm, not more than about 25 ppm, not more than about 10 ppm, not more than about 5 ppm, not more than about 2, not more than about 1, or about 0 ppm, based on the total weight of the stream (or composition). In some embodiments, the total EG content of the purified r-DMT stream in line 128 can be at least about 1, at least about 5, at least about 10, at least about 25, at least about 50, at least about 75, at least about 80, at least about 100, at least about 150, or at least about 200 ppm, based on the total weight of the stream (or composition).

[0145] In some embodiments, the amount (mass) of free EG withdrawn from the purification step / zone 54 (in lines 128, 130 and any other product streams) can be at least about 45, at least about 50, at least about 55, at least about 60, at least about 65, at least about 70, or at least about 75 percent and / or not more than about 99, not more than about 95, not more than about 90, not more than about 85, or not more than about 80 percent of the total amount (mass) of free ethylene glycol introduced into the purification step / zone 54 in line 126 (and all other feed streams), based on the following formula: (Mass of EG in Product Streams) I (Mass of EG in Feed Streams), expressed as a percentage.

[0146] Additionally, or in the alternative, the total amount (mass) of EG-containing impurities, such as MHET and / or BHET, fed into the purification step / zone 54 via line 126 (in combination with any other feed streams, if present) may be at least about 55, at least about 60, at least about 65, at least about 70, at least about 75, or at least about 80 percent and / or not more than about 99, not more than about 95, not more than about 90, or not more than about 85 percent of the total amount (mass) of EG-containing impurities, such as MHET and / or BHET, withdrawn from the purification step / zone 54 in lines 128 and 130 (in combination with any other product streams, if present).

[0147] The purified r-DMT stream in line 128 (or a composition derived therefrom) may comprise trace amounts of elemental antimony, but far less than the molten crude r-DMT stream introduced into the purification step / zone 54 in line 126. For example, in some embodiments, the purified r-DMT stream may comprise less than about 1 ppm of elemental antimony. In some embodiments, the amount of antimony in the purified r-DMT stream in line 128 may be greater than 0 ppm, or at least about 1 , at least about 2, at least about 5, at least about 7, at least about 10, at least about 25, at least about 50, at least about 100, at least about 250, at least about 500, or at least about 750parts per billion by weight (ppb), and / or not more than about 950, not more than about 900, not more than about 850, not more than about 800, not more than about 750, not more than about 700, not more than about 650, not more than about 600, not more than about 550, not more than about 500, not more than about 450, not more than about 400, not more than about 350, not more than about 300, not more than about 250, not more than about 200, or not morethan about 150 ppb elemental antimony, based on the total weight of the stream (or composition).

[0148] In some embodiments, the purified r-DMT stream in line 128 (or a composition derived therefrom) can include less than about 100, less than about 75, less than about 50, less than about 25, or less than about 10 ppm of one or more chosen from dimethyl 1 ,4-cyclohexanedicarboxylate, methyl isopropyl terephthalate, methyl propyl terephthalate, or methyl isobutyl terephthalate, individually or in combination, based on the total weight of the stream (or composition). Additionally, in some embodiments, the purified r-DMT stream in line 128 can comprise less than about 100, less than about 75, less than about 50, or less than about 25 ppm of terephthalic acid (TPA).

[0149] According to some embodiments, the purified r-DMT stream in line 128 (or a composition derived therefrom) can include at least about 1, at least about 10, at least about 25, or at least about 50 ppm and / or not more than about 100, not more than about 75, not more than about 50, or not more than about 25 ppm of one or more compounds chosen from methyl 4-acetylbenzoate, methyl cyanobenzoate, nonylphenol, methyl stearate, methyl laurate, methyl 4-bromobenzoate, diethylene glycol methyl ether, methyl caprylate, 4-methylene cyclohexylmethanol, dimethyl 9-oxo-9H-fluorene-2,6-dicarboxylate, or combinations thereof, based on the total weight of the stream (or composition).

[0150] According to embodiments of the present technology, r-DMT compositions as described herein can be used as a feedstock for several different types of chemical processes, including, for example, for production of various types of polyester, including PET. Use of r-DMT compositions according to embodiments of the present technology can provide various types of polyester with properties indistinguishable from virgin polyesters, but with up to 100 percent recycled content.

[0151] Turning now to FIG. 4, the major steps or zones of a polyester production facility 200 configured for producing a recycled content polyester (r-polyester) from one or more of the above-described r-DMT compositions are provided. In some embodiments, the polyester production facility 200 and the chemical recycling facility (such facility 10 illustrated in FIG. 1) may be colocated. As used herein, the term “co-located” refers to the characteristic of atleast two objects being situated on a common physical site, and / or within 5, within 2, within 1, within 0.75, within 0.5, or within 0.25 miles of each other, measured as a straight-line distance between two designated points. When two facilities are said to be “co-located,” the distances may be measured between geographic centers of the facilities. When two or more facilities are co-located, the facilities may be integrated in one or more ways. Examples of integration include, but are not limited to, heat integration, utility integration, waste-water integration, mass flow integration via conduits, office space, cafeterias, integration of plant management, IT department, maintenance department, and sharing of common equipment and parts, such as seals, gaskets, and the like. In other embodiments, the two facilities 200, 10 are not co-located.

[0152] In some embodiments, the polyester production facility 220 may be operated in a continuous manner, or a portion may be carried out in a batch-wise manner (e.g., a semi-continuous process). As used herein, the term “continuous” refers to a process wherein the reactants are introduced, and the products are withdrawn simultaneously in an uninterrupted manner.

[0153] In some embodiments, the polyester production facility 200 may be a commercial-scale facility. As used herein, the term “commercial scale facility,” in reference to a polyester production facility, means the facility has an average annual terephthalate (e.g., DMT or terephthalic acid) feed rate of at least 500 pounds per hour (Ibs / h), averaged over one year. For example, in some cases, the polyester production facility can have an average annual feed rate of at least 750, at least 1 ,000, at least 2,000, at least 5,000, at least 10,000, at least 50,000, or at least 100,000 Ibs / h and / or not more than about 1 ,000,000, not more than about 500,000, or not more than about 250,000 Ibs / h, averaged over one year.

[0154] In some embodiments, the polyester production facility 200 may or may not be a pilot-scale facility, and it may not be a lab-scale facility. As used herein, the term “pilot-scale,” in reference to a polyester production facility, means the facility has an average annual terephthalate feed rate of between 5 and less than 500 Ibs / h, averaged over one year. Pilot-scale facilities may have an average annual terephthalate feed rate of at least about 25, at least about 50, at least about 100, or at least about 250 Ib / h and / or not more than about450, not more than about 400, not more than about 350, or not more than about 300 Ib / h, averaged over one year. Lab-scale facilities are those conducted in a laboratory, typically in a batch-wise manner. Lab-scale processes can have a feed rate of less than 1, less than about 0.5, or less than about 0.25 Ib / h, if conducted continuously, or less than 5 pounds of terephthalate feed per batch if conducted in a batch-wise manner.

[0155] In some embodiments, the feed rate of r-DMT (or all DMT, if virgin DMT is also used) to the polyester production facility 200 can be at least about 100,000, at least about 110,000, at least about 120,000, at least about 125,000, at least about 130,000, at least about 135,000, at least about 140,000, at least about 145,000, at least about 150,000, at least about 155,000, at least about 160,000, at least about 165,000, at least about 170,000, at least about 175,000, at least about 180,000, at least about 185,000, at least about 190,000, at least about 195,000, at least about 200,000, at least about 205,000, at least about 210,000, at least about 215,000, or at least about 220,000 lbs per year and / or not more than about 1,000,000, not more than about 750,000, or not more than about 500,000 lbs per year, measured on an average of 300 onstream days per year.

[0156] In some embodiments, the production rate of r-polyester from the polyester production facility 200 can be at least about 100,000, at least about 110,000, at least about 120,000, at least about 125,000, at least about 130,000, at least about 135,000, at least about 140,000, at least about 145,000, at least about 150,000, at least about 155,000, at least about 160,000, at least about 165,000, at least about 170,000, at least about 175,000, at least about 180,000, at least about 185,000, at least about 190,000, at least about 195,000, at least about 200,000, at least about 205,000, at least about 210,000, at least about 215,000, or at least about 220,000 lbs per year and / or not more than about 1 ,000,000, not more than about 750,000, or not more than about 500,000 lbs per year, measured on an average of 300 on-stream days per year.

[0157] As shown in FIG. 4, the polyester production facility 200 includes two main reaction steps or zones: a transesterification step or zone 220 followed by a polycondensation step or zone 230. In the transesterification step / zone 220, r-DMT and one or more diols (and optional additional diester or diacid) are reacted to form recycled content polyester oligomer (r-oligomer),which can be further polymerized in the polycondensation step or zone 230 to provide the recycled content polyester (r-polyester). The specific types and amounts of feedstock, as well as the operating conditions within the transesterification and polycondensation steps / zones 220, 230 may be adjusted depending on the specific type of r-polyester being produced. Several embodiments of r-polyesters that can be produced from r-DMT compositions described here are discussed in detail below.

[0158] According to embodiments of the present technology, a stream comprising recycled content DMT (r-DMT) may be introduced into a transesterification step / zone 220 via line 210. In some embodiments, the r-DMT stream may comprise little or no virgin DMT, such that the total recycled content of the stream in line 210 is at least about 90, at least about 95, at least about 98, at least about 99, or at least about 99.9 percent. In some embodiments, the r-DMT stream in line 210 comprises, consists essentially of, or consists of r-DMT having a composition within one or more of the ranges provided herein for the purified r-DMT stream discussed with respect to FIG. 2.

[0159] In some embodiments, another diester (or diacid) may also be added to the transesterification step / zone 220 via line 214, while, in some embodiments, no additional diester (or diacid) may be added. When used, the additional diester (or diacid) may or may not comprise a recycled content diester (or diacid). Examples of suitable additional diesters (or diacids) can include, but are not limited to, terephthalic acid, phthalic acid, isophthalic acid, naphthalene-2,6-dicarboxylic acid, cyclohexanedicarboxylic acid, cyclohexanediacetic acid, diphenyl-4,4'-dicarboxylic acid, dipheny-3,4'-dicarboxylic acid, 2,2,-dimethyl-1 ,3-propandiol, dicarboxylic acid, succinic acid, glutaric acid, adipic acid, azelaic acid, sebacic acid, and 1,4-cyclohexanedicarboxylic acid, C1 to C4 alkyl esters thereof, anhydrides thereof, and combinations thereof.

[0160] Additionally, at least one diol may be introduced into the transesterification step / zone 220 via line 212. As used herein, the term “diol” refers to an organic compound including two or more hydroxyl groups (-OH) bonded to saturated carbon atoms. The term “glycol,” refers to an organic compound including two or more hydroxyl groups (-OH) bonded to saturated carbon atoms and is therefore encompassed by the term “diol.” As used herein,the term “alcohol” refers to an organic compound with a single hydroxyl (-OH) group bonded to a saturated carbon atom.

[0161] In some embodiments, the diol in line 212 may comprise a diol chosen from C2 to C16 diols. Examples include, but are not limited to, one or more of ethylene glycol (EG), diethylene glycol (DEG), triethylene glycol, cyclohexanedimethanol (CHDM), such as 1 ,4-cyclohexanedimethanol (1,4-CHDM) and / or 1 ,3-cyclohexanedimethanol (1,3-CHDM), propane-1 ,2-diol, propane-1 ,3-diol, butane-1,4-diol, pentane-1 ,5-diol, hexane-1 ,6-diol, neopentylglycol (NPG), 3-methylpentanediol-(2,4), 2-methylpentanediol-(1 ,4), 2,2,4-trimethylpentane-diol-(1 ,3), 2-ethylhexanediol-(1 ,3), 2,2-diethylpropanediol-(1 ,3), hexanediol-(1 ,3), 1 ,4-di-(hydroxyethoxy)-benzene, 2,2-bis-(4-hydroxycyclohexyl)-propane, 2,4-dihydroxy-1 , 1 ,3,3-tetramethyl-cyclobutane, 2,2,4,4-tetramethyl-(1 ,3)-cyclobutanediol (TMCD), 2,2-bis-(3-hydroxyethoxyphenyl)-propane, 2,2-bis-(4-hydroxy-propoxyphenyl)-propane, isosorbide, hydroquinone, BDS-(2,2-(sulfonylbis)4,1-phenyleneoxy))bis(ethanol), p-xylylene glycol, polytetramethylene glycol, or mixtures thereof.

[0162] When CHDM is used as or with the diol in line 212, it may comprise 1,4-CHDM, or it may include a blend of 1,4-CHDM and 1,3-CHDM. Additionally, when 1 ,4-CHDM is included, the molar ratio of cis:trans 1 ,4-CHDM can vary within the range of 50:50 to 0:100, such as, for example, from 40:60 to 20:80.

[0163] In some embodiments, two or more diols can be added at the same or different times into the transesterification step / zone 220. When more than one diol is added, at least one of the diols can be a main diol present in an amount of greater than 50, greater than 65, greater than 70, or greater than 75 mole percent, based on the total moles of diols added to the transesterification step / zone 220. One or more additional, or modifying, diols may be added in a total amount of less than 50, less than 35, less than 30, or less than 25 mole percent, based on the total moles of diol introduced into the transesterification step / zone 220. In some embodiments, the main diol can comprise ethylene glycol (EG), cyclohexane dimethanol (CHDM), and combinations thereof, while the additional diol may be chosen from diethylene glycol, 2,2-diethylpropanediol-(1 ,3) or neopentyl glycol (NPG), 2,2,4,4-tetramethyl-cyclobutanediol (TMCD), isosorbide, or combinations thereof.

[0164] Often, the amount of diol added is in stoichiometric excess of the amount of r-DMT (and other diester / diacid) added to the transesterification step / zone 220. For example, in some embodiments, the molar ratio of the total moles of r-DMT (and additional diester or diacid) to total moles of diol introduced into the transesterification step / zone 220 can be greater than 1:1, or can be at least about 1.02: 1 , at least about 1.05: 1 , or at least about 1.1:1 and / or not more than about 5:1, not more than about 4.5:1, not more than about 4:1, not more than about 3.5:1, not more than about 3: 1 , not more than about 2.75: 1 , not more than about 2.6: 1 , or not more than about 2.5:1.

[0165] During transesterification, the average reaction temperature can be at least about 150, at least about 155, at least about 160, at least about 165, at least about 170, at least about at least about 175, at least about 180, at least about 185, at least about 190, at least about 195, at least about 200, at least about 205, at least about 210, at least about 215, at least about 220, at least about 235, at least about 245, at least about 250, at least about 255, or at least about 260°C. Additionally, or in the alternative, the average reaction temperature in the transesterification step / zone 220 can be not more than about 350, not more than about 345, not more than about 335, not more than about 330, not more than about 325, not more than about 320, not more than about 310, not more than about 300, not more than about 285, not more than about 280, not more than about 275, not more than about 270, not more than about 265, not more than about 260, not more than about 255, not more than about 250, not more than about 245, not more than about 240, not more than about 235, not more than about 230, or not more than about 225°C. In some embodiments, the average reaction temperature in the transesterification step / zone 220 can be at least about 270, at least about 275, at least about 280, at least about 285, or at least about 290°C and / or not more than about 325, not more than about 320, not more than about 315, not more than about 310, not more than about 305, or not more than about 300°C.

[0166] In some embodiments, the average pressure during the transesterification reaction in step / zone 220 can be at least about -5, at least about -1 , at least about 0, at least about 5, at least about 10, or at least about15 psig and / or not more than about 75, not more than about 70, not more than about 65, not more than about 60, not more than about 55, not more than about 50 not more than about 45, not more than about 40, not more than about 35, not more than about 30, or not more than about 25 psig. The total reaction time in the transesterification step / zone 220 can be at least about 0.5, at least about 0.75, at least about 1, or at least about 1.5 hours and / or not more than about 10, not more than about 8, not more than about 6, not more than about 5, or not more than about 4 hours.

[0167] The transesterification step / zone 220 may include between 1 and 5 stages (e.g., reactors or vessels, not shown in FIG. 4) in which transesterification between the DMT (and optional additional diester or diacid) and diol (e.g., CHDM and / or EG). Any suitable type of reaction can be used to perform the transesterification step including, but not limited to, CSTRs, plug flow reactors, heat exchangers, horizontal reactors, vertical gravity driven reactors, falling film reactors, and even reactive distillation columns, as well as combinations of two or more of the above.

[0168] After transesterification, a stream comprising recycled content polyester monomers (r-polyester monomers) and oligomers (r-polyester oligomers) may be withdrawn from the transesterification step / zone 220 in line 216, as shown in FIG. 4. As used herein, the term “oligomer” refers to a polymeric species comprising in the range of from 3 to about 50 chain lengths. As used herein, the term “monomer” refers to a polymeric species comprising less than about three chain lengths, while the term “polymer” refers to a polymeric species comprising greater than about 50 chain lengths. The average chain length of the r-oligomer stream exiting the transesterification step / zone 220 in line 216 can be less than about 50, or can be at least about 3, at least about 5, at least about 8, at least about 10, at least about 12, or at least about 15 and / or not more than about 45, not more than about 40, not more than about 35, not more than about 30, not more than about 25, not more than about 20, not more than about 15, or not more than about 10. In some embodiments, the weight average molecular weight (Mw) of the r-oligomer stream in line 216 can be a least about 350, at least about 500, or at least about 750 g / mol and / or not more than about 1500, not more than about 1250, or not more than about 1000 g / mol.

[0169] Additionally, in some cases, the r-DMT conversion after transesterification can be at least 90, at least 92, at least 95, at least 97, or at least 99 percent. As used herein, the term “conversion,” as it related to transesterification, is used to describe a property of the liquid phase of a stream that has been subjected to transesterification, wherein the conversion of the esterified stream indicates the percentage of the original ester end groups that have been converted (i.e., transesterified) to other ester groups. Conversion can be quantified as the number of converted end groups (i.e., alcohol end groups) divided by the total number of end groups (i.e., alcohol plus DMT end groups), expressed as a percentage.

[0170] After transesterification, the r-polyester monomers and r-polyester oligomers in line 216 may be subjected to further polymerization in the polycondensation step / zone 230 shown in FIG. 4. During the polymerization, the end groups of the r-monomers and r-oligomers react further with each other, thereby releasing EG, residual methanol, water, diethylene glycol (DEG), and other diols (when present). This can permit the polymer weight to build. In some embodiments, the polycondensation reaction can be performed in 1 to 3 vessels or stages (not shown) within the step / zone 230. The polycondensation reaction may be performed in any type of reactor, including, but not limited to, a pipe reactor, a frayed reactor, a plug flow reactor, a falling film reactor, or even a reactive distillation column.

[0171] Typically, polycondensation can be carried out at an average temperature in the range of from 220°C to 350°C and a sub-atmospheric (i.e., vacuum) pressure. For example, in some embodiments, the average temperature of the polycondensation reaction can be at least about 225, at least about 230, at least about 235, at least about 240, at least about 245, at least about 250, at least about 255, at least about 260, at least about 265, at least about 270, at least about 275, or at least about 280°C and / or not more than about 345, not more than about 340, not more than about 335, not more than about 330, not more than about 325, not more than about 320, not more than about 315, not more than about 310, not more than about 305, not more than about 300, not more than about 295, not more than about 290, not more than about 285, not more than about 280, not more than about 275, or not more than about 270°C.

[0172] The average pressure of the polycondensation reaction in step / zone 230 can be at least about 0.1 , at least about 0.5, at least about 1 , at least about 5, at least about 10, at least about 25, at least about 50, at least about 75, at least about 100, at least about 125, at least about 150, or at least about 200 mm Hg and / or not more than about 750, not more than about 700, not more than about 650, not more than about 600, not more than about 550, not more than about 500, not more than about 450, not more than about 400, not more than about 350, not more than about 300, not more than about 250, or not more than about 200 mm Hg. The polycondensation reaction may be performed for a total reaction time of at least about 0.5, at least about 0.6, at least about 0.75, or at least about 1 hour and / or not more than about 10, not more than about 8, not more than about 6, not more than about 4, or not more than about 2 hours.

[0173] In some embodiments, the transesterification and / or polycondensation reactions may be performed in the presence of at least one catalyst. The catalyst may be present in an amount of at least 0.1 , at least 10, at least 25, at least 50, at least 100, or at least 250 ppm and / or not more than 500, not more than 350, not more than 250, not more than 100 ppm, based on the weight of polyester in each reaction step / zone 220, 230. Examples of suitable transesterification catalysts can include, but are not limited to, titanium alkoxides, tin (II) or (IV) esters, alkali metals or alkali earth metals (e.g., Li and Ca), manganese compounds, zinc compounds, magnesium acetates or benzoates, and combinations thereof, while the polycondensation catalysts may comprise at least one catalytically active metal compound such as titanium, aluminum, antimony, germanium, cobalt, alkali metals, and alkaline earth metals, magnesium, calcium, and combinations thereof. In some embodiments, the transesterification and / or polycondensation reaction may be performed in the presence of one or more catalysts that include less than about 50, less than about 25, less than about 10, less than about 5, less than about 2, or less than about 1 , or about 0 ppm of antimony. In some embodiments, an antimony catalyst may be used.

[0174] In some embodiments, the rate of polymerization in the polycondensation step / zone 230 can be adjusted to achieve the desirable degree of polymerization or inherent viscosity in the recycled content polyesterpolymer melt (r-polyester polymer melt) exiting from the polycondensation step / zone 230 in line 218 as shown in FIG. 4. For example, the mass transfer rate during at least a portion, or all, of the polymerization step may be at least 1 , at least 1.25, at least 1.5, at least 1.75 or at least 2 number average degree(s) of polymerization (DP) per minute (DP / min).

[0175] The r-polyester polymer melt exiting the polycondensation step / zone 230 via line 218 can have an inherent viscosity (IV) of at least 0.50, at least 0.52, at least 0.55, at least 0.57, at least 0.60, at least 0.62, at least 0.65, at least 0.67, at least 0.68, at least 0.69, at least 0.70, at least 0.71 , at least 0.72, at least 0.73, at least 0.74, at least 0.75, at least 0.76, at least 0.77, at least 0.78, at least 0.79, or at least 0.80 dL / g. Additionally, or in the alternative, the r-polyester polymer melt withdrawn from the reaction zone of the polyester production facility can have an inherent viscosity (IV) of not more than 1.10, not more than 1.07, not more than 1.05, not more than 1.02, not more than 1.0, not more than 0.97, not more than 0.95, not more than 0.94, not more than 0.93, not more than 0.92, not more than 0.91, not more than 0.90, not more than 0.89, not more than 0.88, not more than 0.87, not more than 0.86, not more than 0.85, not more than 0.84, not more than 0.83, not more than 0.82, not more than 0.81, not more than 0.80, not more than 0.79, not more than 0.78, not more than about 0.75, not more than about 0.73, not more than about 0.70, not more than about 0.67, not more than about 0.65, not more than about 0.63, or not more than about 0.62 dL / g. The inherent viscosity (IV) is measured at 25°C in 60 / 40 wt / wt phenol / tetrachloroethane, unless otherwise noted.

[0176] As shown in FIG. 4 the r-polyester polymer melt in line 218 removed from the polycondensation step / zone 230 can be introduced into a post treatment step / zone 240. In some embodiments, in the post treatment step / zone 240, at least a portion of the r-polyester polymer melt may be pelletized and then crystallized to form recycled content polyester (r-polyester) particles in line 222. The particles, once formed, are solid at 25°C and 1 atmosphere. The r-polyester particles can have any suitable shape including, but not limited to, spheres, cubes, pellets, chips, pastilles, stars, and combinations thereof. In some cases, the particles have a number average weight of at least 0.10, at least 1 , at least 10, or at least 50 g per 100 particles.The volume of particles is not particularly limited, but there can be provided a bulk of particles having a volume of at least 1 , at least 3, or at least 5 cubic meters.

[0177] The method of pelletizing the r-polyester polymer melt is not limited. For example, in some cases, the molten polyester may be directed through a die and cut at the die head to form the r-polyester particles. In some cases, the die head may be under a liquid (such as water or other aqueous liquid), so that the particles are immediately in contact with the liquid upon exiting the die. This method is generally referred to as underwater cutting. In some cases, the r-polymer particles are formed by subjecting the r-polyester polymer melt to underwater cutting.

[0178] After being formed, the r-polyester particles can optionally be at least partially dried and can then be crystallized to form crystalline r-polyester particles. Any suitable method of crystallization can be used, and the particles can, for example, be thermally crystallized in a gas or liquid. The crystallization vessel can be mechanically agitated, such as in a fluidized bed, or it can be unagitated. In some embodiments, the crystallization occurs via contact with a crystallization liquid medium at a temperature above the glass transition temperature (Tg) of the polyester. In some cases, the crystallization can be latent heat crystallization and may be performed without addition of external heat or energy.

[0179] In some embodiments, the crystallized r-polyester particles may be solid stated (or solid state polymerized) according to known methods. As used herein, “solid state polymerization” refers to a process in which the polymer chain lengths are increased by heating the polyester in the substantial absence of oxygen and water. During solid state polymerization, the polymer is in a solid form and not in the melt phase. In some embodiments, the crystallized r-polyester pellets may not be solid stated, such that less than 10, less than 5, less than 2, less than 1 , or less than 0.5 percent of the total inherent viscosity (IV) can be added to the final r-polyester after polycondensation. Accordingly, the difference in inherent viscosity (IV) between the r-polyester polymer melt and the crystallized r-polyester particles can be not more than 0.25, not more than 0.20, not more than 0.15, not more than 0.10, or not more than 0.05 dL / g, when no solid state polymerization occurs. After crystallization,the r-polyester particles can be contacted with a vapor stream to strip out acetaldehyde (AA) and other low volatility components.

[0180] The final r-polyester produced by facility 400 in line 222 can include a diester component comprising predominantly residues of r-DMT and a diol component including residues of one or more diols as described herein. As used herein, the term “predominantly” means at least 50 weight (or mole) percent, as applicable. All the compounds containing ester groups (or corresponding acid groups) present in the r-polyester make up the “diester component,” and the mole percentages of the residues of all of these compounds in the r-polyester equals 100 percent. As used herein, the term “residue” refers to the portion of the compound(s) which remains in the oligomer and / or polymer chain after the condensation reaction. Thus, the residues of the diester compounds present in the r-polyester refers to the portion of those diester compounds which remain in the polymer chain after the diester has been condensed with a compound containing hydroxyl group(s).

[0181] Similarly, all the compounds containing hydroxyl group(s) or derivatives thereof that become part of the r-polyester comprise the “diol component,” and the mole percentage of all such compounds containing hydroxyl groups in the r-polyester totals 100. The residues of the diol compounds refer to the portion of the diol which remains in the r-polyester after polymerization. The mole percentages of specific diester and diol residues in the r-polyester can be determined by proton NMR.

[0182] In some embodiments, the r-polyester formed as described herein can comprise a diester component including at least about 45, at least about 50, at least about 55, at least about 60, at least about 65, at least about 70, at least about 75, at least about 80, at least about 85, at least about 90, at least about 95, at least about 96, at least about 97, at least about 97.5, at least about 98, at least about 98.5, at least about 99, at least about 99.5, or about 100 percent of residues of r-DMT, based on the total weight of diester residues in the r-polyester. Alternatively, or in addition, the r-polyester can include residues of r-DMT in an amount of not more than about 99.9, not more than about 99.5, not more than about 99, not more than about 98.5, not more than about 98, or not more than about 97.5 mole percent, based on the total moles of diester residues in the r-polyester.

[0183] Additionally, in some embodiments, the diester component of the r-polyester can include residues of at least one modifying diester (or diacid) in addition to the residues of r-DMT. When used, the modifying acid diester (or diacid) can comprise an aromatic diester (or diacid) having up to about 20 carbon atoms per molecule and / or it may comprise an aliphatic diester (or diacid) having up to about 16 carbon atoms per molecule. Examples of suitable modifying diesters can include, but are not limited to, alkyl esters of one or more of phthalic acid, isophthalic acid, naphthalene-2,6-dicarboxylic acid, cyclohexanedicarboxylic acid, cyclohexanediacetic acid, diphenyl-4,4'-dicarboxylic acid, dipheny-3, 4' -dicarboxylic acid, dicarboxylic acid, succinic acid, glutaric acid, adipic acid, azelaic acid, sebacic acid, and 1,4-cyclohexanedicarboxylic acid, and combinations thereof. Additionally, in some cases, one or more of these may be used as a modifying diacid. When used, one or more of the above can comprise a recycled content diester (or diacid) or may not include recycled content.

[0184] In some embodiments, the r-polyester can include at least about 0.1, at least about 0.5, at least about 1, at least about 2, at least about 5, at least about 7, or at least about 10 mole percent and / or not more than about 45, not more than about 40, not more than about 35, not more than about 30, not more than about 25, not more than about 20, not more than about 15, not more than about 10, or not more than about 5 mole percent of residues of one or more modifying diesters (or diacids), based on the total moles of diester residues in the r-polyester. In some embodiments, the r-polyester may include less than about 5, less than about 3, less than about 2, less than about 1, less than about 0.5, or about 0 mole percent of modifying diester (or diacid) residues, based on the total moles of diester residues in the r-polyester.

[0185] Further, in some embodiments, since the r-polyester is DMT-based, it can include little or no residues of terephthalic acid (TPA). For example, the r-polyester can include not more than 0.50, not more than 0.25, not more than 0.10, or not more than 0.05 mole percent of residues of terephthalic acid, based on the total moles of diester residues in the r-polyester. In some embodiments, the absence of TPA may result in lower in situ formation of diethylene glycol (DEG), so the r-polyester particles may, for example, have a DEG content of not more than about 2.5, not more than about 2, not morethan about 1.75, not more than about 1.5, not more than about 1.25, not more than about 1, not more than about 0.75, or not more than about 0.5, not more than about 0.45, or not more than about 0.40 mole percent, based on the total moles of the diol component. Additionally, or in the alternative, the amount of DEG present in the r-polyester can be at least about 0.1, at least about 0.2, at least about 0.25, at least about 0.30, or at least about 0.35 mole percent, based on the total moles of diol residues in the r-polyester.

[0186] In some embodiments, the r-polyester can comprise residues of DEG in an amount of at least about 1, at least about 1.5, at least about 2, at least about 2.5, or at least about 3 mole percent and / or not more than about 5, not more than about 4.5, not more than about 4, not more than about 3.5, or not more than about 3 mole percent, based on the total moles of diol residues in the r-polyester.

[0187] Additionally, in some embodiments, since the r-polyester is formed from r-DMT (and not terephthalic acid), it may comprise at least about 5, at least about 7, at least about 12, at least about 15, or at least about 20 mole percent and / or not more than about 30, not more than about 27, not more than about 25, not more than about 20, not more than about 17, not more than about 15, or not more than about 12 mole percent of methyl end groups, based on the total number of end groups in the r-polyester. Polyesters formed from terephthalic acid do not have a methyl end group content within these ranges. In some cases, the r-polyester may have a carboxyl number of less than about 15, less than about 10, less than about 7, less than about 5, or less than about 2 meq / kg, which may also denote DMT-based r-polyesters.

[0188] In some cases, the r-polyester may also not include other components typically associated with TPA-based polyesters. For example, in some embodiments, the r-polyester can comprise not more than 100, not more than 75, not more than 50, not more than 25, or not more than 10 ppm of cobalt (Co) and / or bromide (Br), which are typically present in the process for forming TPA. Additionally, or alternatively, the r-polyester can comprise not more than 100, not more than 75, not more than 50, not more than 25, or not more than 10 ppm of one or more metals selected from manganese (Mn), zinc (Zn), and combinations thereof. In some cases, the r-polyester can include not more than 0.1, not more than 0.05, or not more than 0.01 mole percent of residues of 4-carboxybenzaldehyde and 9-fluoreneone-2,6-dicarboxylic acid, based on the total moles of the polyester. These components are typical intermediates in a TPA-based polyester process and would not be present (or would be present only in very minor amounts) in DMT-based polyester processes.

[0189] The r-polyesters described herein may be prepared from dicarboxylic acids and diols which react in substantially equal proportions and are incorporated into the r-polyester as their corresponding residues. The r-polyesters of the present disclosure, therefore, can contain substantially equal molar proportions of diester (or diacid) residues (100 mole percent) and diol (and / or multifunctional hydroxyl compound) residues (100 mole percent) such that the total moles of repeating units of each type are equal to 100 mole percent. The mole percentages provided in the present disclosure, therefore, may be based on the total moles of diester (or diacid, where noted) residues, the total moles of diol residues, or the total moles of repeating units. For example, a r-polyester containing 10 mole percent dimethyl isophthalate, based on the total diester residues, means the r-polyester contains 10 mole percent dimethyl isophthalate residues out of a total of 100 mole percent diester residues. Thus, there are 10 moles of dimethyl isophthalate residues among every 100 moles of diester residues. In another example, a r-polyester containing 25 mole percent 1 ,4-cyclohexanedimethanol, based on the total diol residues, means the r-polyester contains 25 mole percent 1 ,4-cyclohexanedimethanol residues out of a total of 100 mole percent diol residues. Thus, there are 25 moles of 1 ,4-cyclohexanedimethanol residues among every 100 moles of diol residues.

[0190] According to some embodiments, the r-polyester formed with one or more of the r-DMT compositions described herein can be a polyester having a diol component including residues of 2,2,4,4-tetramethyl-1 ,3-butanediol (TMCD). For example, in some embodiments, the r-polyester can include from about 1 to about 99 mole percent of residues of TMCD and from about 1 to about 99 mole percent of residues of at least one additional diol chosen from ethylene glycol (EG), cyclohexanedimethanol (CHDM), or combinations thereof, wherein each molar percentage is based on the total moles of diol residues in the r-polyester. All or a portion of one or more of the TMCD, EG, and / or CHDM may comprise recycled content (r-TMCD, r-EG,and / or r-CHDM), or all or a portion of one or more of the TMCD, EG, and / or CHDM may not include recycled content. In some embodiments, the r-polyester may comprise less than about 5, less than about 3, less than about 2, less than about 1, less than about 0.5, or less than about 0.1 mole percent of residues other than EG, CHDM, and TMCD, based on the total moles of diol residues in the r-polyester.

[0191] The r-polyester can include residues of TMCD in an amount of at least about 5, at least about 10, at least about 15, at least about 20, at least about 25, at least about 30, or at least about 35 mole percent and / or not more than about 75, not more than about 70, not more than about 65, not more than about 60, not more than about 55, not more than about 50, not more than about 45, not more than about 40, not more than about 35, not more than about 30, or not more than about 25 mole percent, based on the total moles of diol residues in the r-polyester.

[0192] Additionally, in some embodiments, the r-polyester can include from about 1 to about 99 mole percent of residues of CHDM (or r-CHDM) in addition to the residues of TMCD. The CHDM residues can be derived from 1 ,3-cyclohexanedimethanol (1,3-CHDM), 1 ,4-cyclohexanedimethanol (1,4-CHDM), or combinations thereof. In such embodiments, the r-polyester can include at least about 25, at least about 30, at least about 35, at least about 40, at least about 45, at least about 50, at least about 55, at least about 60, at least about 65, at least about 70, or at least about 75 mole percent and / or not more than about 95, not more than about 90, not more than about 85, not more than about 80, not more than about 75, not more than about 70, not more than about 65, or not more than about 60 mole percent, based on the total moles of diol residues in the r-polyester. Accordingly, the r-polyester can include residues of EG (or r-EG) in an amount of not more than about 5, no more than about 3, not more than about 2, not more than about 1 , not more than about 0.5, or not more than about 0.1 mole percent, based on the total moles of diol residues in the r-polyester.

[0193] In some embodiments, the r-polyester can include from about 1 to about 99 mole percent residues of EG (or r-EG) in addition to the residues of TMCD. For example, the r-polyester can comprise at least about 55, at least about 60, at least about 65, at least about 70, at least about 75, or at least about80 mole percent and / or not more than about 98.5, not more than about 98, not more than about 97.5, not more than about 97, not more than about 95, not more than about 92.5, not more than about 90, not more than about 85, or not more than about 80 mole percent of EG (or r-EG) residues, based on the total moles of diol residues in the r-polyester.

[0194] In some embodiments, the r-polyester can comprise TMCD (or r-TMCD) residues in an amount of at least about 1.5, at least about 2, at least about 2.5, at least about 3, at least about 5, at least about 7.5, at least about 10, at least about 15, or at least about 20 mole percent and / or not more than about 45, not more than about 40, not more than about 35, not more than about 30, not more than about 25, or not more than about 20 mole percent, based on the total moles of diol residues in the r-polyester. Additionally, in some embodiments, the r-polyester can include residues of CHDM (or r-CHDM) in an amount of not more than about 5, not more than about 3, not more than about 2, not more than about 1 , not more than about 0.5, or not more than about 0.1 mole percent, based on the total moles of diol residues in the r-polyester.

[0195] The r-polyester including a diol component as described above may have a diester component comprising at least about 85, at least about 90, at least about 95, at least about 97, at least about 98, at least about 99, or at least about 99.5 mole percent, or at least about 100 mole percent of r-DMT. It may also comprise not more than about 15, not more than about 10, not more than about 5, not more than about 3, not more than about 2, not more than about 1, or not more than about 0.5, or 0 mole percent of diesters (or diacids) other than r-DMT.

[0196] According to some embodiments, the r-polyester formed with r-DMT compositions as described herein can comprise a glycol-modified polyester. In some embodiments, the r-polyester can include a diol component that comprises residues of CHDM and EG and less than about 5, less than about 4.5, less than about 4, less than about 3.5, less than about 3, less than about 2.5, less than about 2, less than about 1.5, less than about 1 , or less than about 0.5 mole percent, or about 0 mole percent of diol residues other than EG and CHDM (such as, for example, NPG). The r-polyester can include at least about 98, at least about 98.5, at least about 99, at least about 99.5, at least about 99.9 mole percent, or about 100 percent of residues of CHDM and mayinclude not more than about 2, not more than about 1.5, not more than about 1, not more than about 0.5, not more than about 0.1, or 0 mole percent of residues of diols other than CHDM, based on the total moles of diol residues in the r-polyester.

[0197] When the diol component includes residues of both CHDM and EG, the r-polyester can include residues of CHDM in an amount of at least about 25, at least about 30, at least about 35, at least about 40, at least about 45, at least about 50, at least about 55, at least about 60, or at least about 65 mole percent and / or about 100 mole percent and / or not more than about 95, not more than about 90, not more than about 85, more than about 80, not more than about 75, not more than about 70, not more than about 65, not more than about 60, not more than about 55, not more than about 50, not more than about 45, not more than about 40, or not more than about 35 mole percent, based on the total moles of diol residues in the r-polyester.

[0198] Additionally, or in the alternative, the r-polyester can comprise residues of EG in an amount of about 0, or at least about 5, at least about 10, at least about 15, at least about 20, at least about 25, at least about 30, at least about 35, at least about 40, at least about 45, at least about 50, at least about 55, at least about 60, or at least about 65 mole percent and / or not more than about 75, not more than about 70, not more than about 65, not more than about 60, not more than about 55, not more than about 50, not more than about 45, not more than about 40, or not more than about 35 mole percent, based on the total moles of diol residues in the r-polyester.

[0199] In some embodiments, when the r-polyester includes predominantly residues of EG and CHDM, the diol component of the r-polyester may include more CHDM than EG, while in other embodiments, the diol component may include more EG than CHDM. As used herein with respect to residues of an r-polyester, the term “more (A) than (B)” means that the diol (or diester) component includes at least 5 percentage points more of residues of A than residues of B, on a molar basis. For example, an r-polyester including a diol component with 40 mole percent of residues of EG and 60 mole percent of residues of CHDM includes more CHDM than EG (60 mole percent - 40 mole percent = 20 percentage point difference).

[0200] In some embodiments, the r-polyester can have a diol component comprising residues of CHDM in an amount of at least about 1, at least about 1.5, at least about 2, at least about 2.5, at least about 3, at least about 3.5, at least about 4, at least about 4.5, or at least about 5 mole percent and / or not more than about 20, not more than about 17.5, not more than about 15, not more than about 12, not more than about 10, not more than about 7.5, not more than about 5, or not more than about 4 mole percent, based on the total weight of diol residues in the r-polyester. Additionally, or in the alternative, the r-polyester can include at least about 85, at least about 88, at least about 90, at least about 92, at least about 95, or at least about 96 mole percent and / or not more than about 99.9, not more than about 99, not more than about 98.5, not more than about 98, not more than about 97.5 not more than about 97, not more than about 96.5, or not more than about 96 mole percent of residues of EG, based on the total moles of diol residues in the r-polyester.

[0201] In some embodiments, the r-polyester can comprise CHDM residues in an amount of at least about 95, at least about 97, at least about 98, at least about 98.5, at least about 99, at least about 99.5, at least about 99.9 mole percent, based on the total moles of diol residues in the r-polyester. Additionally, or in the alternative, the r-polyester can comprise not more than about 2, not more than about 1.5, not more than about 1, not more than about 0.5, or not more than about 0.1, or about 0 mole percent of residues other than CHDM (including, for example, EG), based on the total moles of diol residues in the r-polyester.

[0202] According to some embodiments, the r-polyester can comprise residues of CHDM in an amount of at least about 1, at least about 2, at least about 5, at least about 10, at least about 15, or at least about 20 mole percent and / or not more than about 45, not more than about 40, not more than about 35, not more than about 30, not more than about 25, not more than about 20, not more than about 15, not more than about 10, or not more than about 5 mole percent, based on the total moles of diol residues in the r-polyester. Additionally, or in the alternative, the r-polyester can include at least about 1 , at least about 2, at least about 5, at least about 7, or at least about 10 mole percent and / or not more than about 20, not more than about 17.5, not more than about 15, not more than about 12, not more than about 10, not more than about 8, ornot more than about 6 mole percent of residues of diethylene glycol (DEG), based on the total moles of diol in the r-polyester.

[0203] In some embodiments, the r-polyester can include at least about 2, at least about 3, at least about 5, or at least about 7 mole percent and / or not more than about 25, not more than about 24, not more than about 22.5, not more than about 20, not more than about 18, not more than about 15, or not more than about 13 mole percent of residues of NPG, based on the total moles of diol residues in the r-polyester. Accordingly, in some embodiment, the r-polyester can comprise EG residues in an amount of at least about 45, at least about 50, at least about 55, at least about 60, at least about 65, at least about 70, at least about 75, or at least about 80 mole percent and / or not more than about 95, not more than about 90, not more than about 85, not more than about 80, not more than about 75, not more than about 70, not more than about 65 mole percent, based on the total moles of diol residues in the r-polyester. In some embodiments, the r-polyester can comprise residues of CHDM, DEG, and NPG within the above ranges, with EG making up the balance of the diol component.

[0204] The r-polyester including a diol component as described above may have a diester component comprising at least about 85, at least about 90, at least about 95, at least about 97, at least about 98, at least about 98.5, at least about 99, at least about 99.5, or at least about 99.9 mole percent, or at least about 100 mole percent of r-DMT. It may also comprise not more than about 15, not more than about 10, not more than about 5, not more than about 3, not more than about 2, not more than about 1.5, not more than about 1, or not more than about 0.5, not more than about 0.1, or about 0 mole percent of diesters (or diacids) other than r-DMT.

[0205] In some embodiments, the r-polyester can include residues of r-DMT in an amount of at least about 45, at least about 50, at least about 55, at least about 60, or at least about 65 mole percent and / or not more than about 95, not more than about 90, not more than about 85, not more than about 80, not more than about 75, not more than about 70, not more than about 65, not more than about 60, or not more than about 55 mole percent, based on the total moles of diol residues in the r-polyester.

[0206] In some embodiments, the r-polyester may comprise residues of at least one modifying diester, such as, for example, dimethyl isophthalate (DMI), which can comprise recycled content DMI (r-DMI) or non-recycled content DMI. When present, the r-polyester can comprise residues of r-DMI in an amount of at least about 5, at least about 10, at least about 15, at least about 20, at least about 25, at least about 30, at least about 35, at least about 40, or at least about 45 mole percent and / or not more than about 55, not more than about 50, not more than about 45, not more than about 40, not more than about 35, or not more than about 30 mole percent, based on the total moles of diester residues in the r-polyester.

[0207] In some embodiments of the present technology, the r-DMT compositions formed as described herein can be used to produce PET polyesters having low (e.g., less than 10 mole percent) of diester (or diacid) and / or diol substitution. That is, the PET polyesters can have a diester component comprising at least about 88, at least about 90, at least about 92, at least about 95, at least about 97, at least about 98, at least about 98.5, at least about 99, at least about 99.5, or at least about 99.9 mole percent residues of r-DMT and a diol component comprising at least about 88, at least about 90, at least about 92, at least about 95, at least about 97, at least about 98, at least about 98.5, at least about 99, at least about 99.5, or at least about 99.9 mole percent residues of EG.

[0208] The balance of one or both the diester and diol component may include one or more modifying diesters (or diacids) and / or modifying diols as described in detail previously. That is, the r-polyesters can include less than about 12, less than about 10, less than about 8, less than about 5, less than about 3, less than about 2, less than about 1.5, less than about 1, less than about 0.5, or less than about 0.1 mole percent of residues other than r-DMT (for the diester component) or EG (for the diol component), based on the total moles of residues of the diester or diol. Additionally, the r-polyester can comprise residues of diols other than EG (e.g. , one or more modifying diols) in an amount of at least about 0.5, at least about 1 , at least about 2, at least about 5, or at least about 6 mole percent, based on the total moles of diol residues in the r-polyester. In some embodiments, the r-polyester can include about 100 molepercent of residues of r-DMT and about 100 mole percent of residues of EG, with any other diol residues present being generated in situ (e.g., DEG).

[0209] According to some embodiments of the present technology, the r-polyesters formed from the r-DMT compositions described herein may comprise residues of isosorbide. For example, in some cases, the r-polyester can comprise at least about 1 , at least about 1.5, at least about 2, at least about 2.5, at least about 3, at least about 5, at least about 10, at least about 15, at least about 20, at least about 22, at least about 25, at least about 27, or at least about 30 mole percent and / or not more than about 75, not more than about 70, not more than about 65, not more than about 60, not more than about 55, not more than about 50, not more than about 45, not more than about 40, not more than about 35, not more than about 30, not more than about 25, not more than about 20, not more than about 15, not more than about 10, or not more than about 8 mole percent of residues isosorbide, based on the total moles of diol residues in the r-polyester.

[0210] In some embodiments, the r-polyester can comprise at least about 25, at least about 30, at least about 35, at least about 40, at least about 45, at least about 50, at least about 55, at least about 60, at least about 65, at least about 70, at least about 75, at least about 80, at least about 85, or at least about 90 mole percent and / or about 100 mole percent and / or not more than about 95, not more than about 90, not more than about 85, not more than about 75, or not more than about 70 mole percent, based on the total moles of diol residues in the r-polyester. In other embodiments, the r-polyester can includes residues of isosorbide in an amount of not more than about 20, not more than about 18, not more than about 15, not more than about 12, not more than about 10, not more than about 8, not more than about 6, not more than about 5, or not more than about 3 mole percent, based on the total moles of diol residues in the r-polyester.

[0211] In addition to isosorbide, the r-polyester may comprise residues of one or more other diols such as, for example, CHDM and / or EG. For example, in some cases, the r-polyester can comprise residues of CHDM and / or EG in an amount of a least about 5, at least about 10, at least about 15, at least about 20, at least about 25, at least about 30, at least about 35, at least about 40, at least about 45, or at least about 50 mole percent and / or not morethan about 80, not more than about 75, not more than about 70, not more than about 65, not more than about 60, not more than about 55, not more than about 50, not more than about 45, not more than about not more than about 40, or not more than about 35 mole percent, based on the total moles of diol residues in the r-polyester.

[0212] In some embodiments, the r-polyester can include at least about 50, at least about 55, at least about 60, at least about 65, at least about 70, at least about 75, at least about 80, at least about 85, at least about 90, or at least about 95 mole percent and / or not more than about 99, not more than about 95, not more than about 90, not more than about 85, not more than about 80, not more than about 75, not more than about 70, or not more than about 65 mole percent of residues of CH DM and / or EG, based on the total moles of diol residues in the r-polyester.

[0213] In some embodiments, the r-polyester can include residues of CHDM in an amount of at least about 35, at least about 40, at least about 45, at least about 50, at least about 55, at least about 60, or at least about 65 mole percent and / or not more than about 95, not more than about 90, not more than about 85, not more than about 80, not more than about 75, not more than about 70, not more than about 65, not more than about 60, not more than about 55, or not more than about 50 mole percent, based on the total moles of diol residues in the r-polyester. Additionally, or in the alternatively, the r-polyester can include residues of EG in an amount of at least about 5, at least about 10, at least about 15, at least about 20, at least about 25, at least about 30, at least about 35, or at least about 40 mole percent and / or not more than about 65, not more than about 60, not more than about 55, not more than about 50, not more than about 45, not more than about 40, not more than about 35, not more than about 30, not more than about 25, not more than about 20, or not more than about 15 mole percent, based on the total moles of diol residues in the r-polyester.

[0214] In addition to isosorbide and CHDM and / or EG, the r-polyester can further comprise residues of at least one additional modifying diol chosen from, for example, diethylene glycol, neopentyl glycol, 2,2,4,4-tetramethyl-1 ,3-cyclobutanediol, 1,2-propanediol, 1 ,3-propanediol, butanediol, or combinations thereof. When present, the r-polyester may comprise residues of one or moreof these additional diols in an amount of at least about 0.1 , at least about 0.5, at least about 1 , at least about 2, at least about 3, at least about 5, or at least about 7.5 mole percent and / or not more than about 10, not more than about 8, not more than about 7, not more than about 6, not more than about 5, not more than about 3, not more than about 2, not more than about 1.5, or not more than about 1 mole percent, based on the total moles of diol in the r-polyester.

[0215] The r-polyester including a diol component as described above may have a diester component comprising at least about 85, at least about 90, at least about 95, at least about 97, at least about 98, at least about 98.5, at least about 99, at least about 99.5, or at least about 99.9 mole percent, or at least about 100 mole percent of r-DMT. It may also comprise not more than about 15, not more than about 10, not more than about 5, not more than about 3, not more than about 2, not more than about 1.5, not more than about 1, or not more than about 0.5, not more than about 0.1, or about 0 mole percent of diesters (or diacids) other than r-DMT.

[0216] According to some embodiments, the r-polyester of one or more of the above compositions can have an inherent viscosity, as determined in 60 / 40 (wt / wt) phenol / tetrachloroethane at a concentration of 0.5 g / dL at 25°C, of at least about 0.5, at least about 0.55, at least about 0.60, at least about 0.65, at least about 0.70, or at least about 0.75 dL / g and / or not more than about 1.2, not more than about 1.1, not more than about 1.0, not more than about 0.95, not more than about 0.90, not more than about 0.85, not more than about 0.80, not more than about 0.75, or not more than about 0.70 dL / g.

[0217] In some embodiments, the r-polyester can have a glass transition temperature of at least about 60, at least about 65, at least about 70, at least about 72, or at least about 74°C and / or not more than about 85, not more than about 80, not more than about 77, or not more than about 75°C. Additionally, in some embodiments, the r-polyester can have a glass transition temperature of at least about 75, at least about 80, at least about 85, at least about 90, at least about 95, at least about 100, at least about 105, at least about 110, at least about 120, or at least about 125°C and / or not more than about 170, not more than about 165, not more than about 160, not more than about 155, not more than about 150, not more than about 145, not more than about 140, not more than about 135, or not more than about 130°C. The glasstransition temperature is determined using a TA DSC 2920 from Thermal Analyst Instrument at a scan rate of 20° C. / min. The value of the glass transition temperature is determined during the second heat.

[0218] In some embodiments, the r-polyester can have a b* color of less than about 2, less than about 1 , less than about 0, or in the range of from about -2 to about 2, about -1.5 to about 1.5, or about -1 to about 0. The r-polyester can have a b* value of less than 10.5, not more than about 10, not more than about 9, not more than about 8, not more than about 7, not more than about 6, not more than about 5.5, not more than about 5, not more than about 4.5, or not more than about 3.5. In some embodiments, the r-polyester can have a b* value of less than 10.5, not more than about 10, not more than about 9, not more than about 8, not more than about 7, not more than about 6, not more than about 5, not more than about 4, not more than about 3, not more than about 2, or not more than about 1.

[0219] In some embodiments, the r-polyester can have an a* value of not more than about 1.35, not more than about 1.3, not more than about 1.25, not more than about 1.2, not more than about 1.15, not more than about 1.1, not more than about 1, not more than about 0.75, not more than about 0.5, not more than about 0.25, not more than about 0.10, or not more than about 0, not more than about -0.1, or not more than about -0.25. Additionally, or in the alternative, the a* value can be at least -0.5, at least about -0.49, at least about -0.48, at least about -0.47, at least about -0.46, at least about -0.45, at least about -0.425, or at least about -0.40. In some embodiments, the r-polyester can have an a* value of not more than about 2, not more than about 1.75, not more than about 1.5, not more than about 1.3, not more than about 1.25, not more than about 1.2, not more than about 1.15, not more than about 1.1, not more than about 1, not more than about 0.75, not more than about 0.5, not more than about 0.25, not more than about 0.10, or not more than about 0, not more than about -0.1, not more than about -0.25, not more than about -0.5, or not more than about -0.75.

[0220] In some embodiments, the r-polyester can have an L* color greater than about 70, greater than about 75, greater than about 80, greater than about 85 and / or not more than about 95, not more than about 92, not more than about 90, or not more than about 87. In some embodiments, the r-polyester can have an L* value of at least about 65, at least about 70, at least about 71, at least about 72, at least about 73, at least about 74, at least about 75, at least about 76, at least about 77, at least about 78, at least about 79, at least about 80, at least about 81 , at least about 82, at least about 83, or at least about 84 and / or not more than about 90, not more than about 89, not more than about 88, not more than about 87, or not more than about 86. The L* value can be greater than 55, at least about 60, at least about 65, at least about 70, at least about 71, at least about 72, at least about 73, at least about 74, at least about 75, at least about 76, at least about 77, at least about 78, at least about 79, at least about 80, at least about 81 , at least about 82, at least about 83, or at least about 84 and / or not more than about 90, not more than about 89, not more than about 88, not more than about 87, or not more than about 86.

[0221] In some embodiments, the r-polyester can have a haze value, measured according to ASTM D1003-97 of less than 5, less than about 4.5, less than about 4, less than about 3.5, less than about 3, less than about 2.75, less than about 2.5, less than about 2.25, less than about 2, less than about 1.75, less than about 1.5, less than about 1.25, less than about 1, less than about 0.75, less than about 0.5, or less than about 0.25%.

[0222] According to some embodiments, the r-polyester formed as described herein may comprise a small amount of residual antimony, which would not be present in similar polyesters formed from virgin DMT. Additionally, the amount of antimony in the r-polyesters formed according to embodiments of the present technology is less than would be present in other polyesters formed from unpurified recycled content DMT. In particular, r-polyesters according to embodiments of the present technology can have an antimony content of at least about 1 , at least about 2, at least about 5, at least about 10, at least about 15, at least about 20, at least about 25, at least about 30, at least about 35, at least about 40, at least about 45, at least about 50, at least about 75, at least about 100, or at least about 150 parts per billion by weight (ppb) and / or not more than about 500, not more than about 450, not more than about 400, not more than about 350, not more than about 300, not more than about 250, not more than about 200, not more than about 150, nor more than about 100, not more than about 95, not more than about 90, not more than about 85, not more than about 80, not more than about 75, not more than about 70, notmore than about 65, not more than about 60, not more than about 55, not more than about 50, not more than about 45, or not more than about 25 ppb of antimony, based on the total weight of the polyester.

[0223] In some embodiments, the r-polyester can have an antimony content of at least about 200, at least about 250, at least about 300, at least about 350, at least about 400, at least about 450, at least about 500, at least about 750, or at least about 1000 ppb, or at least about 2, at least about 5, at least about 10, at least about 25, or at least about 50 parts per million by weight (ppm) and / or not more than about 50, not more than about 25, not more than about 10, not more than about 5, not more than about 2, not more than about 1 ppm or not more than about 750, not more than about 500, not more than about 250, or not more than about 100 ppb of antimony, based on the total weight of the r-polyester. In some embodiments, the r-polyester can have an elemental antimony content of from about 1 to about 850 ppb, about 1 to about 500 ppb, about 1 to about 250 ppb, about 1 to about 100 ppb, about 1 to about 75 ppb, about 1 to about 50 ppb.

[0224] According to embodiments of the present technology, there is provided recycled content polyethylene terephthalate (r-PET) composition formed by mixing chemically recycled PET (cr-PET) and mechanically recycled PET (mr-PET), optionally with virgin PET, to form an r-PET composition that can be used in a wide variety of applications. For example, such r-PET compositions can be used to form bottles, preforms, containers, sheets, films, fibers, textiles, thermoforms, injection molded components, and combinations thereof.

[0225] In some embodiments the blended r-PET composition can have a higher recycled content than other PET compositions having similar properties. For example, in some embodiments, the r-PET composition (or recycled content article, r-article, formed from the r-PET composition) can have an overall recycled content of at least about 50, at least about 55, at least about 60, at least about 65, at least about 70, at least about 75, at least about 80, at least about 85, at least about 90, at least about 95, at least about 99, or even up to 100 percent recycled content. Additionally, or in the alternative, the r-PET composition (or r-article) can have an overall recycled content of at least about 5, at least about 10, at least about 15, at least about 20, at least about 25, atleast about 30, at least about 35, or at least about 40 percent and / or not more than about 99, not more than about 95, not more than about 90, not more than about 85, not more than about 80, not more than about 75, not more than about 70, not more than about 65, not more than about 60, not more than about 55, not more than about 50, not more than about 45, not more than about 40, not more than about 35, not more than about 30, not more than about 25, or not more than about 20 percent.

[0226] In some embodiments, the blended r-PET composition can have an L* value of at least about 80, at least about 81 , at least about 82, at least about 83, at least about 84, at least about 85, at least about 86, at least about 87, at least about 88, at least about 89, at least about 90, at least about 91 , at least about 92, at least about 93, at least about 94, or at least about 95, measured according to 1976 CIE L*b*a* Color Space. In some cases, the L* of the blended r-PET composition can be within about 15, within about 12, within about 10, within about 8, within about 5, within about 2, within about 1 , or within about 0.5 of the L* value of a virgin PET having an identical composition but no recycled content or of the L* value of the virgin PET included in the blended r-PET composition.

[0227] In some embodiments, the blended r-PET composition can have a haze value, measured according to ASTM D-1003, using a 1 / 8-inch thick plaque, of less than about 20, less than about 19, less than about 18, less than about 17, less than about 16, less than about 15, less than about 14, less than about 13, less than about 12, less than about 10, less than about 9, less than about 8, less than about 7, less than about 6, less than about 5, less than about 4, less than about 3, less than about 2, less than about 1 , less than about 0.95, less than about 0.90, less than about 0.85, less than about 0.80, or less than about 0.75 percent.

[0228] According to some embodiments, the cr-PET and virgin PET, when present, may have similar compositions and properties. In other embodiments, particularly when the PET is not formed with an antimony catalyst, the cr-PET may still include low levels of antimony (e.g., from 1 ppb to about 500 ppb as discussed previously), while the non-antimony catalyzed virgin PET may include 0 ppb of elemental antimony, based on the total weightof the PET. Residual antimony may be present in both types of PET when formed in an antimony-catalyzed process.

[0229] In some embodiments, the cr-PET and / or virgin PET may not include much, if any, nitrogen, chloride, and / or silicon. Specifically, the cr-PET and / or virgin PET may include less than 5, less than about 4, less than about 3, less than about 2, less than about 1 , less than about 0.5, or about 0 ppm of total Cl and / or total N, individually or in combination, based on the total weight of the PET. Additionally, or alternatively, the cr-PET and / or virgin PET may include total Si in an amount of not more than about 24, not more than about 24, not more than about 23, not more than about 22, not more than about 21 , not more than about 20, not more than about 19, not more than about 18, not more than about 17, not more than about 16, not more than about 15, not more than about 14, not more than about 13, not more than about 12, not more than about 11 , not more than about 10, not more than about 9, not more than about 8, not more than about 7, not more than about 6, not more than about 5, not more than about 4, not more than about 3, not more than about 2, not more than about 1 , not more than about 0.5, or about 0 ppm, based on the total weight of the PET.

[0230] Further, in some embodiments since the cr-PET and / or virgin PET may be formed from r-DMT (and not TPA), it may comprise at least about 2, at least about 3, at least about 4, at least about 5, at least about 7, at least about 12, at least about 15, or at least about 20 mole percent and / or not more than about 30, not more than about 27, not more than about 25, not more than about 20, not more than about 17, not more than about 15, not more than about 12, not more than about 10, or not more than about 5 mole percent of methyl end groups, based on the total moles of terephthalate. Mechanically recycled PET can be formed from TPA and, as a result, does not have methyl end groups in the above ranges.

[0231] Additionally, the cr-PET and / or virgin PET used to form the r-PET blends may include low levels of CHDM modification. For example, in some embodiments, the cr-PET and / or virgin PET may include at least about 0.1 , at least about 1 , at least about 2, at least about 3, at least about 4, at least about 5, or at least about 6 mole percent and / or not more than about 11, not more than about 10, not more than about 8, not more than about 6, not morethan about 5, not more than about 4, not more than about 3, or not more than about 2 mole percent of residues of CHDM, based on the total moles of diol residues in the cr-PET and / or virgin PET. Mechanically recycled PET does not include such levels of CHDM modification.

[0232] The cr-PET and / or virgin PET can have a haze value of less than about 3, less than about 2.75, less than about 2.5, less than about 2.5, less than about 2, less than about 1.75, less than about 1.5, less than about 1.25, or less than about 1 percent, measured according to ASTM D-1003 measured using a 1 / 8-inch thick plaque.

[0233] Prior to mixing, the cr-PET and / or virgin PET can be in the form of particles (e.g., pellets, pastilles, powder) having regular or irregular shapes, or it can be in the form of flakes, chunks, or fragments of fibers, sheets, films, or combinations thereof. In some embodiments, the cr-PET or virgin PET may be molten, and it may or may not have previously been pelletized.

[0234] According to some embodiments, the mr-PET can comprise greater than 15, at least about 16, at least about 17, at least about 18, at least about 19, at least about 20, at least about 21 , at least about 22, at least about 23, at least about 24, at least about 25, at least about 30, at least about 35, at least about 40, or at least about 45 ppm and / or not more than about 80, not more than about 75, not more than about 70, not more than about 65, not more than about 60, not more than about 55, not more than about 50, not more than about 45, or not more than about 40 ppm of total Cl, based on the total weight of the r-PET composition.

[0235] In some embodiments, the mr-PET can comprise greater than 15, at least about 16, at least about 17, at least about 18, at least about 19, at least about 20, at least about 21, at least about 22, at least about 23, at least about 24, at least about 25, at least about 30, at least about 35, at least about 40, or at least about 45 ppm and / or not more than about 80, not more than about 75, not more than about 70, not more than about 65, not more than about 60, not more than about 55, not more than about 50, not more than about 45, or not more than about 40 ppm of total N, based on the total weight of the mr-PET.

[0236] In some embodiments, the mr-PET can comprise at least about 25, at least about 30, at least about 35, at least about 40, at least about 45, atleast about 50, at least about 55, at least about 60, at least about 65, at least about 70, at least about 75, or at least about 80 ppm and / or not more than about 200, not more than about 175, not more than about 150, not more than about 125, not more than about 100, not more than about 95, not more than about 90, not more than about 85, not more than about 80, not more than about 75, not more than about 70, not more than about 65, not more than about 60, not more than about 55, or not more than about 50 ppm of total Si, based on the total weight of the r-PET composition.

[0237] As discussed previously, mr-PET may be formed from terephthalic acid (TPA) and, as a result, may have few or no methyl end groups. For example, in some embodiments, the mr-PET added to (or present in) the blended r-PET composition can comprise not more than about 1.75, not more than about 1.5, not more than about 1, not more than about 0.5, or not more than about 0.1, or about 0 mole percent of methyl end groups, based on the total moles of terephthalate. Additionally, or in the alternative, the mr-PET may include little or no CHDM modification, such that the total residues of CHDM in the mr-PET can be not more than about 0.1, not more than about 0.05, or not more than about 0.01 , or about 0 mole percent, based on the total moles of diol residues in the mr-PET.

[0238] In some embodiments, the mr-PET may have been previously sorted to remove one or more inorganic (e.g., metal or glass), organic (e.g., paper or cardboard), and / or non-polyester (e.g., polyolefin or polyvinyl chloride) components such that the mr-PET may include at least about 0.1 , at least about 0.5, at least about 0.75, at least about 1 , at least about 1.25, at least about 1.5, at least about 1.75, or at least about 2 weight percent and / or not more than about 5, not more than about 4.5, not more than about 3.5, not more than about 3, or not more than about 2.5 weight percent of one or more components chosen from inorganic materials, non-polyester polymers, non-polymeric organic materials, or combinations thereof. Specific examples of each of these types of components that may be present in the mr-PET are discussed previously with regard to the mixed plastic waste feed stream shown in FIG. 1. The cr-PET and virgin PET each comprise not more than about 100, not more than about 50, not more than about 25, not more than about 10, or about 0 ppm of each of these types of non-polyester materials, individually or in combination.

[0239] In some embodiments, the mr-PET can have a haze value greater than 20, at least about 21, at least about 22, at least about 23, at least about 24, or at least about 25 percent, measured according to ASTM D-1003 with a 1 / 8-inch plaque.

[0240] In some embodiments, the mr-PET may comprise residues of terephthalic acid (TPA) and can, therefore, comprise no (0 percent) detectable methyl end groups. Additionally, or alternatively, the mr-PET may comprise at least about 2, at least about 2.5, at least about 3, or at least about 5 and / or not more than about 10, not more than about 8, not more than about 6, or not more than about 3 mole percent of residues of isophthalic acid (or dimethyl isophthalate), based on the total moles of diacid (or diester) residues in the mr-PET. Further, in some embodiments, the mr-PET may not be CHDM modified, such that it can comprise not more than about 0.1, not more than about 0.05, or not more than about 0.01 mole percent of CHDM, based on the total moles of diol residues in the mr-PET.

[0241] Prior to mixing, the mr-PET can be in the form of particles (e.g., pellets, pastilles, powder) having regular or irregular shapes, or it can be in the form of flakes, chunks, or fragments of fibers, sheets, films, or combinations thereof. In some embodiments, at least a portion of the mr-PET added to form the blended r-PET composition may comprise molten mr-PET.

[0242] In some embodiments, the blended r-PET composition can include at least about 5, at least about 10, at least about 15, at least about 20, at least about 25, at least about 30, at least about 35, at least about 40, at least about 45, at least about 50, at least about 55, at least about 60, at least about 65, at least about 70, at least about 75, or at least about 80 weight percent and / or not more than about 95, not more than about 90, not more than about 85, not more than about 80, not more than about 75, not more than about 70, not more than about 65, not more than about 60, not more than about 55, not more than about 50, not more than about 45, not more than about 40, not more than about 35, not more than about 30, not more than about 25, or not more than about 20 weight percent of cr-PET, based on the total weight of the blended r-PET composition.

[0243] Additionally, the blended r-PET composition can include at least about 5, at least about 10, at least about 15, at least about 20, at least about25, at least about 30, at least about 35, at least about 40, at least about 45, at least about 50, at least about 55, at least about 60, at least about 65, at least about 70, at least about 75, or at least about 80 weight percent and / or not more than about 95, not more than about 90, not more than about 85, not more than about 80, not more than about 75, not more than about 70, not more than about 65, not more than about 60, not more than about 55, not more than about 50, not more than about 45, not more than about 40, not more than about 35, not more than about 30, not more than about 25, or not more than about 20 weight percent of mr-PET, based on the total weight of the blended r-PET composition.

[0244] In some embodiments, the blended r-PET composition may comprise a combined amount of mr-PET and cr-PET that is greater than 50, at least about 55, at least about 60, at least about 65, at least about 70, at least about 75, at least about 80, at least about 85, at least about 90, at least about 95, at least about 99, or about 100 percent of the composition, based on the total weight of the blended r-PET composition.

[0245] According to some embodiments, the blended r-PET composition may also comprise virgin PET. In other embodiments, the blended r-PET composition may not include virgin PET. When included, the virgin PET can be present in the blended r-PET composition in an amount of at least about 5, at least about 10, at least about 15, at least about 20, at least about 25, at least about 30, at least about 35, at least about 40, at least about 45, at least about 50, at least about 55, at least about 60, at least about 65, at least about 70, at least about 75, or at least about 80 weight percent and / or not more than about 95, not more than about 90, not more than about 85, not more than about 80, not more than about 75, not more than about 70, not more than about 65, not more than about 60, not more than about 55, not more than about 50, not more than about 45, not more than about 40, not more than about 35, not more than about 30, not more than about 25, or not more than about 20 weight percent, based on the total weight of the blended r-PET composition.

[0246] Thus, the r-PET composition may not include 100 weight percent of (be only) cr-PET, may not include 100 weight percent of (be only) mr-PET, and may not include 100 weight percent of (be only) virgin r-PET. As a result, the properties of the r-PET composition according to embodiments of the present technology may have different properties and / or a differentcomposition than pure (e.g., 100 weight percent) cr-PET, pure mr-PET, and pure virgin PET.

[0247] For example, in some embodiments, the blended r-PET composition may include total chloride (Cl) in an amount of at least about 5 parts per million by weight (ppm) and / or less than 15 ppm, or in an amount of at least about 6, at least about 7, at least about 8, at least about 9, at least about 10, at least about 11, at least about 12, at least about 13, at least about 14, or at least about 15 ppm and / or not more than about 14, not more than about 13, not more than about 12, not more than about 11 , not more than about 10, not more than about 9, not more than about 8, not more than about 7, not more than about 6, or not more than about 5 ppm of total Cl, based on the total weight of the r-PET composition. Total (elemental) chloride is measured using combustion ion chromatography (CIC).

[0248] In some embodiments, the blended r-PET composition may include total Cl in an amount of at least about 5, at least about 10, at least about 15, at least about 20, at least about 25, at least about 30, at least about 35, at least about 40, at least about 45, at least about 50, at least about 55, at least about 60, at least about 65, at least about 70, or at least about 75 ppm and / or not more than about 150, not more than about 140, not more than about 130, not more than about 120, not more than about 110, not more than about 105, not more than about 100, not more than about 90, not more than about 80, not more than about 75, not more than about 70, not more than about 65, not more than about 60, not more than about 55, not more than about 50, not more than about 45, not more than about 40, not more than about 35, not more than about 30, not more than about 25, not more than about 20, or not more than about 15 ppm, based on the total weight of the r-PET composition.

[0249] In some embodiments, the blended r-PET composition may include total nitrogen (N) in an amount of at least about 5 parts per million by weight (ppm) and / or less than 15 ppm, or in an amount of at least about 6, at least about 7, at least about 8, at least about 9, at least about 10, at least about 11, at least about 12, at least about 13, at least about 14, or at least about 15 ppm and / or not more than about 14, not more than about 13, not more than about 12, not more than about 11 , not more than about 10, not more than about 9, not more than about 8, not more than about 7, not more than about 6, or notmore than about 5 ppm of total N, based on the total weight of the r-PET composition. Total (elemental) nitrogen is determined using a total nitrogen analyzer.

[0250] In some embodiments, the blended r-PET composition may include total N in an amount of at least about 5, at least about 10, at least about 15, at least about 20, at least about 25, at least about 30, at least about 35, at least about 40, at least about 45, at least about 50, at least about 55, at least about 60, at least about 65, at least about 70, or at least about 75 ppm and / or not more than about 150, not more than about 140, not more than about 130, not more than about 120, not more than about 110, not more than about 105, not more than about 100, not more than about 90, not more than about 80, not more than about 75, not more than about 70, not more than about 65, not more than about 60, not more than about 55, not more than about 50, not more than about 45, not more than about 40, not more than about 35, not more than about 30, not more than about 25, not more than about 20, or not more than about 15 ppm, based on the total weight of the r-PET composition.

[0251] In some embodiments, the blended r-PET composition can include a combined amount of total chloride (Cl) and total nitrogen (N) of at least about 5, at least about 6, at least about 7, at least about 8, at least about 9, at least about 10, at least about 11, at least about 12, at least about 13, at least about 14, at least about 15, at least about 16, at least about 17, at least about 18, at least about 19, or at least about 20 ppm and / or not more than about 30, not more than about 29, not more than about 28, not more than about 27, not more than about 26, not more than about 25, not more than about 24, not more than about 23, not more than about 22, not more than about 21 , not more than about 20, not more than about 19, not more than about 18, not more than about 17, not more than about 16, not more than about 15, not more than about 14, not more than about 13, not more than about 12, not more than about 11, or not more than about 10 ppm.

[0252] According to some embodiments, the blended r-PET composition may include total silicon (Si) in an amount of at least about 5, at least about 10, at least about 15, at least about 20, at least about 25, at least about 30, at least about 35, at least about 40, at least about 45, at least about 50, at least about 55, at least about 60, at least about 65, at least about 70, orat least about 75 ppm and / or not more than about 500, not more than about 450, not more than about 400, not more than about 350, not more than about 300, not more than about 250, not more than about 200, not more than about 150, not more than about 140, not more than about 130, not more than about 120, not more than about 110, not more than about 105, not more than about 100, not more than about 90, not more than about 80, not more than about 75, not more than about 70, not more than about 65, not more than about 60, not more than about 55, not more than about 50, not more than about 45, not more than about 40, not more than about 35, not more than about 30, not more than about 25, not more than about 20, or not more than about 15 ppm, based on the total weight of the r-PET composition. Total (elemental) silicon is measured using x-ray fluorescence (XRF).

[0253] In some embodiments, the blended r-PET composition can include a combined amount of total chloride (Cl), total nitrogen (N), and total silicon (Si) of at least about 5, at least about 6, at least about 7, at least about 8, at least about 9, at least about 10, at least about 11, at least about 12, at least about 13, at least about 14, at least about 15, at least about 16, at least about 17, at least about 18, at least about 19, at least about 20, at least about 21 , at least about 22, at least about 23, at least about 24, at least about 25, at least about 26, at least about 27, at least about 28, at least about 29, or at least about 30 ppm and / or not more than about 60, not more than about 59, not more than about 58, not more than about 57, not more than about 56, not more than about 55, not more than about 54, not more than about 53, not more than about 52, not more than about 51 , not more than about 50, not more than about 49, not more than about 48, not more than about 47, not more than about 46, not more than about 45, not more than about 44, not more than about 43, not more than about 42, not more than about 41 , not more than about 40, not more than about 39, not more than about 38, not more than about 37, not more than about 36, not more than about 35, not more than about 34, not more than about 33, not more than about 32, not more than about 31 , not more than about 30, not more than about 29, not more than about 28, not more than about 27, not more than about 26, not more than about 25, not more than about 20, not more than about 15, or not more than about 10 ppm, based on the total weight of the r-PET composition.

[0254] In some embodiments, the blended r-PET composition includes a combined amount of Cl, N, and Si of at least about 25, at least about 30, at least about 35, at least about 40, at least about 45, at least about 50, at least about 55, at least about 60, at least about 65, at least about 70, at least about 75, at least about 80, at least about 85, or at least about 90 ppm and / or not more than about 500, not more than about 450, not more than about 400, not more than about 350, not more than about 300, not more than about 250, not more than about 150, not more than about 100, not more than about 75, or not more than about 50 ppm, based on the total weight of the r-PET composition.

[0255] Additionally, the blended r-PET composition may include few or no components other than PET. For example, in some embodiments, the blended r-PET composition may include not more than about 5, not more than about 4, not more than about 3, not more than about 2, not more than about 1 , not more than about 0.5, or not more than about 0.1 weight percent of any components other than the PET forming the blend. Specifically, the total amount of cr-PET, mr-PET, and, when present, virgin PET can comprise at least about 95, at least about 97, at least about 98, at least about 99, or about 100 percent of the total blended r-PET composition. Thus, not more than 5, not more than 3, not more than 2, not more than 1 , or about 0 percent of the total blended r-PET composition can be components other than the cr-PET, the mr-PET, and, when present, the virgin PET.

[0256] In some embodiments, the blended r-PET composition can have a total methyl end group concentration of greater than about 0, at least about 0.1, at least about 0.2, at least about 0.25, at least about 0.3, at least about 0.5, at least about 1 , at least about 2, at least about 2.5, at least about 3, at least about 3.25, or at least about 3.5 mole percent and / or not more than about 20, not more than about 19, not more than about 18, not more than about 17, not more than about 16, not more than about 15, not more than about 14, not more than about 13, not more than about 12, not more than about 11, not more than about 10, not more than about 9, not more than about 8, not more than about 7, not more than about 6, not more than about 5, not more than about 4, not more than about 3, not more than about 2.5, not more than about 2.25, not more than about 2, or not more than about 1.5 mole percent of methylend groups, based on the total moles of terephthalate. Methyl end group concentration can be measured by NMR at a frequency of at least 400 MHz.

[0257] In some embodiments, the blended r-PET composition can have a total CHDM modification level of greater than about 0, at least about 0.1, at least about 0.25, at least about 0.3, at least about 0.5, at least about 1, at least about 1.5, at least about 2, at least about 5, at least about 7 mole percent and / or not more than about 11 , not more than about 10, not more than about 8, not more than about 5, not more than about 4, not more than about 3, not more than about 2, or not more than about 1.5 mole percent, based on the total moles of diol in the blended r-PET composition. In some embodiments, the blended r-PET composition can comprise less than about 2, less than about 1.75, less than about 1.5, less than about 1.25, less than about 1, less than about 0.75, less than about 0.5, less than about 0.25, or less than about 0.1 mole percent of residues of isophthalic acid (and / or dimethyl isophthalate), based on the total moles of diol residues in the r-PET composition.

[0258] In some embodiments, the blended r-PET composition can comprise less than 5, less than about 4.5, less than about 4, less than about 3.5, less than about 3, less than about 2.5, less than about 2, less than about 1.5, or less than about 1 weight percent of residues of components other than ethylene glycol, dimethyl terephthalate, and terephthalic acid.

[0259] The blended r-PET compositions including mr-PET, cr-PET, and, optionally, virgin PET, may be formed by mixing the components simultaneously or in sequence in any suitable manner to form the blended composition. In some embodiments, the blending can include combining two (or three) of the polyesters to form a heterogeneous blend of particles, (e.g., pellets, flakes, etc.), wherein individual particles are formed from one of the different polyesters, while, in other embodiments, the blending can include melt blending two (or three) polyesters (e.g., cr-PET, mr-PET, and / or virgin PET) to form a homogeneous molten r-PET blend that may then be pelletized.

[0260] Turning now to FIGS. 5a and 5b, the major steps of methods for forming blended r-PET compositions according to embodiments of the present technology are provided. As shown in both FIGS. 5a and 5b, an r-DMT stream in line 210 formed and having a composition as described herein may be introduced into a polymerization step or zone 250, wherein it may bepolymerized to form a chemically recycled PET (cr-PET) having a composition as also described herein.

[0261] Referring initially to FIG. 5a, in the embodiment presented therein, the resulting, molten chemically recycled polyester (cr-PET) in line 222 may be blended with a stream of mechanically recycled polyester (mr-PET) in line 226 in a blending step or zone 260 to provide a predominantly molten blended recycled content polyester (r-PET) composition. The specific amounts of cr-PET and mr-PET added to blending step / zone 260 and in the resulting molten blended r-PET composition may fall within one or more of the ranges provided previously.

[0262] The mr-PET in line 226 can be in any suitable form when blending with the cr-PET in FIG. 5a, including, for example, flakes, chunks, pellets, fibers, sheets, bottles, containers, fragments thereof, and mixtures thereof. In some embodiments, the mr-PET in line 226 may be combined with the molten cr-PET upstream and / or at one or more points within an extruder (not shown in FIG. 5a), whereupon the mr-PET may be melted to form the molten blended r-PET composition in line 228. According to some embodiments, the mr-PET may be melted in a separate extrusion step or zone (not shown in FIG. 5a) and the resulting molten mr-PET may be combined with the molten cr-PET to form the molten blended r-PET. In other embodiments, at least a portion of the mr-PET can be added to the polymerizate in the latter stages of the polymerization step or zone 250 to provide a blended r-PET composition in line 222.

[0263] As shown in FIG. 5a, the molten blended r-PET composition in line 228 may then be pelletized in a pelletizing step or zone 70 to form a plurality of blended r-PET pellets in line 230. At least about 90, at least about 92, at least about 95, at least about 97, at least about 99, or about 100 percent of the blended r-PET pellets in line 230 of FIG. 5a comprise both mr-PET and cr-PET in a single pellet in amounts such as, greater than about 10 weight percent of each of mr-PET and cr-PET. Individual ones of such pellets may have properties and compositions of the blended r-PET compositions described herein. Further, although described herein as being in the form of “pellets,” the blended r-PET particles in line 228 may be in any suitable form, including, but not limited to flakes, particles, pastilles, fibers, powder, or combinations thereof.

[0264] Referring now to FIG. 5b, another embodiment of forming a blended r-PET composition is provided. As shown in FIG. 5b, the molten cr-PET in line 222 may be withdrawn from the polymerization step / zone 250 and then pelletized in pelletizing step / zone 270 to form a plurality of cr-PET pellets. In some embodiments, at least about 90, at least about 92, at least about 95, at least about 97, at least about 99, or about 100 percent of the cr-PET pellets comprise at least about 90, at least about 92, at least about 95, at least about 97, at least about 99, or about 100 weight percent cr-PET, based on the total weight of the pellets, with not more than about 10, not more than about 8, not more than about 5, not more than about 2, not more than about 1 , or 0 weight percent of components other than the cr-PET being present in the cr-PET pellets, based on the total weight of the pellets. Such pellets have properties and compositions of the cr-PET described herein.

[0265] As shown in FIG. 5b, the cr-PET pellets exiting the pelletizing step / zone 70 in line 224 can then be blended with a plurality of mr-PET pellets in line 226 to form a r-PET pellet blend in line 232. In some embodiments, at least about 90, at least about 92, at least about 95, at least about 97, at least about 99, or about 100 percent of the mr-PET pellets in line 226 can comprise at least about 90, at least about 92, at least about 95, at least about 97, at least about 99, or about 100 percent of mr-PET, based on the total weight of the pellets, with not more than about 10, not more than about 8, not more than about 5, not more than about 2, not more than about 1 , or 0 weight percent of components other than the mr-PET being present in the mr-PET pellets, based on the total weight of the pellets. Such pellets have properties and compositions of the mr-PET described herein.

[0266] The resulting r-PET pellet blend in line 232 comprises a heterogeneous blend of cr-PET pellets and mr-PET pellets. These pellets, individually, have properties of the cr-PET and mr-PET, respectively, and do not have properties of the r-PET blend. However, the r-PET pellet blend may exhibit properties of the blended r-PET composition as described below. The amount of each of the cr-PET and the mr-PET in the r-PET pellet blend in line 232 can vary and may fall within the ranges of r-PET blend compositions provided above.

[0267] In some embodiments, the blended r-PET composition can further include virgin PET. When present, the virgin PET can be added in a similar manner as the mr-PET shown and described with respect to FIGS. 5a and 5b. Specifically, the virgin PET may be in the form of particles (e.g., pellets, flakes, pastilles, etc.) and may be added upstream or within one or more zones of an extruder. Alternatively, the virgin PET pellets can be combined with pellets of cr-PET (or with blended r-PET pellet blend) to form the blended r-PET composition. In some embodiments, the virgin PET (which may or may not have been pelletized) may be combined with the molten cr-PET in molten form and the resulting molten blend can be pelletized as discussed previously. When both mr-PET and virgin PET are combined with the cr-PET, the mr-PET and virgin PET may be added in the same way (e.g., both as pellets upstream of an extruder) or the two may be added in different ways (e.g., one upstream of the extruder and the other as pellets with the cr-PET pellets).

[0268] The final blended r-PET composition may be in any suitable form, including, for example, in the form of a pellets including both cr-PET and mr-PET in a single pellet, a blend of individual cr-PET and mr-PET pellets, a molten polymer stream, or an end product such as a film, sheet, fiber, preform, bottle, etc. Regardless of its form, the blended r-PET composition can have a haze value (at least slightly) greater than the haze value of 100 weight percent cr-PET or virgin PET, but (at least slightly) less than 100 weight percent mr-PET.

[0269] In some embodiments, the blended r-PET composition can have a haze value, measured according to ASTM D-1003 (with a 1 / 8-inch plaque), of at least (greater than) 2 percent and not more than (less than) 20%. In some embodiments, the blended r-PET can have a haze value of at least about 2.5, at least about 3, at least about 3.5, at least about 4, at least about 4.5, at least about 5, at least about 5.5, at least about 6, at least about 6.5, at least about 7, at least about 7.5, at least about 8, at least about 8.5, at least about 9, at least about 9.5, at least about 10, at least about 10.5, at least about 11 , at least about 11.5, at least about 12, at least about 12.5, at least about 13, at least about 13.5, at least about 14, at least about 14.5, or at least about 15 percent and / or not more than about 19, not more than about 18.5, not more than about 18, not more than about 17.5, not more than about 17, not morethan about 16.5, not more than about 16, not more than about 15.5, not more than about 15, not more than about 14.5, not more than about 14, not more than about 13.5, not more than about 13, not more than about 12.5, not more than about 12, not more than about 11.5, not more than about 11 , not more than about 10.5, not more than about 10, not more than about 9.5, not more than about 9, not more than about 8.5, not more than about 8, not more than about 7.5, not more than about 7, not more than about 6.5, not more than about 6, not more than about 5.5, not more than about 5, not more than about 4.5, not more than about 4, or not more than about 3.5 percent. In other embodiments, the r-PET can have a haze value of less than about 3, less than about 2, less than about 1 , less than about 0.95, less than about 0.90, less than about 0.85, less than about 0.80, or less than about 0.75 percent, measured according to ASTM D-1003.

[0270] In some embodiments, the blended r-PET composition can have a color defined by an L* color value of at least about 90, at least about 91 , at least about 92, at least about 93, at least about 94, at least about 95, at least about 96, at least about 97, at least about 98, or at least about 99, measured according to the 1976 CIE L*a*b* Color Space.

[0271] Turning now to FIG. 6, a flow diagram illustrating the major steps in a method 300 for forming a blended recycled content polyester (r-PET) composition is provided. As shown in FIG. 6, the first step 310 of the method 300 is to select a target value for a property of the target r-PET blend. For example, in some embodiments, the property may be chosen from L* color, haze, crystallization half-time, or it may be a specific compositional property, such as the amount of chloride, nitrogen, and / or silicon, or even antimony, present in the final blended r-PET composition. In step 310, a target value for the property may be set and can fall, for example, within one or more of the ranges provided herein. As an example, a target value of 3.5 percent may be chosen for the haze of the blended r-PET composition to be formed according to the method 300.

[0272] As shown in FIG. 6, the next step 320 of the method 300 may be to form a blend of mr-PET and virgin PET. Such a blend can be formed by mixing pellets of mr-PET with virgin PET or combining pellets of one with a molten stream or mass of the other. The resulting first blend can include, forexample, least about 5, at least about 10, at least about 15, at least about 20, at least about 25, at least about 30, or at least about 35 weight percent and / or not more than about 75, not more than about 70, not more than about 65, not more than about 60, not more than about 55, not more than about 50, not more than about 45, not more than about 40, not more than about 35, or not more than about 30 weight percent of the mr-PET and / or least about 5, at least about 10, at least about 15, at least about 20, at least about 25, at least about 30, or at least about 35 weight percent and / or not more than about 75, not more than about 70, not more than about 65, not more than about 60, not more than about 55, not more than about 50, not more than about 45, not more than about 40, not more than about 35, or not more than about 30 weight percent of the virgin PET, based on the total weight of the first composition. In some embodiments, at least about 90, at least about 92, at least about 95, at least about 97, at least about 99, or about 100 weight percent of the first r-PET blend include mr-PET and virgin PET.

[0273] Thereafter, as shown in FIG. 6, the next step 330 of the method 300 can be to measure a value for the selected property of the first blend to provide a first measured value. For example, if haze is the selected property, step 330 may include measuring the haze of a first blend of mr-PET and virgin PET to provide a first measured value. Next, as shown by step 340, the first measured value can be compared with the target value set in step 310 to determine a first difference. For example, if the target haze value set in step 310 is 3.5 percent and the first measured value of the first r-PET blend is 4.75 percent, the first difference would be 1.25 percent (e.g., 4.75% - 3.5% = a 1.25% difference).

[0274] In some embodiments, the first difference may be at least about 5, at least about 10, at least about 15, a least about 20, at least about 25, at least about 30, at least about 35, at least about 40, at least about 45, or at least about 50 percent of the target value for the property set in step 310, expressed by the following formula: first difference I target value, expressed as a percentage. For example, if the first difference between the target haze value and the measured haze value is 1.25% and the target haze value is 3.5%, the first difference would be 35.7% of the target value (e.g., 1.25% I 3.5% = 0.357 = 35.7%).

[0275] Next, as shown in FIG. 6, based on the first difference, an amount of cr-PET may be combined with mr-PET to form a second r-PET blend. The cr-PET may be added to the first blend to form a blend of mr-PET, virgin PET, and cr-PET or the cr-PET may be blended with mr-PET to form the second blend, as shown by step 350. In some embodiments, the amount of cr-PET added can be such that the amount of cr-PET present in the second blend is at least about 5, at least about 10, at least about 15, at least about 20, at least about 25, at least about 30, or at least about 35 weight percent and / or not more than about 75, not more than about 70, not more than about 65, not more than about 60, not more than about 55, not more than about 50, not more than about 45, not more than about 40, not more than about 35, or not more than about 30 weight percent, based on the total weight of the second blend. In some embodiments, at least about 90, at least about 92, at least about 95, at least about 97, or at least about 99 weight percent, or about 100 weight percent of the second r-PET blend comprises mr-PET, cr-PET, and, when present, virgin PET.

[0276] Thereafter, as shown in FIG. 6, a value of the selected property can then be measured for the second r-PET blend, as shown by step 360, and the resulting second measured value can be compared with the target value to determine a second difference, as shown in step 370 in FIG. 6.

[0277] In some embodiments, if the second difference is greater than 5, greater than 10, greater than 15, greater than 20, or greater than 25 percent of the target value, steps 350 through 370 shown in FIG. 6 can be repeated until the second difference is less than 25, less than 20, less than 15, less than 10, or less than 5 percent of the target value, as expressed by the following formula: second difference I target value, expressed as a percentage. For example, if after adding the cr-PET to the first polyester blend, the second measured haze value was 3.75 percent, the second difference (with a 3.5 percent target value) would be 0.25 percent (e.g., 3.75% - 3.5% = 0.25%), which would be 7 percent of the target value (0.2513.5 = 0.07 = 7%).

[0278] If desired, the steps of adding more cr-PET to the second blend (e.g., step 350 in FIG. 6), measuring the haze value of the new blend (e.g., step 360 in FIG. 6), and then comparing the new measured value and target value (e.g., step 370 in FIG. 6) could be repeated until the second difference is lessthan 25, less than 20, less than 15, less than 10, or less than 5 percent of the target value. As a result, blended r-PET compositions having higher recycled content can be formed that have properties within desired ranges, making these blends suitable for wide employment in a variant of end use applications.

[0279] The r-polyesters (including the blended r-PET compositions) described herein may be used in a variety of end use applications, including to form recycled content articles (r-articles) such as molded articles, sheets, films, trays, rods, tubes, lids, preforms, containers (medical containers, personal care containers, and cosmetic containers), bottles (water bottles, hot fill bottles, and carbonated soft drink bottles), as well as various types of packaging (including shrink film packaging) and filaments, fibers, yarns, and textiles. The r-articles produced according to embodiments of the present technology can be molded articles, extruded articles, or fibers. The r-articles can be single-use or multiuse articles. Specific applications include, but are not limited to, food and beverage, packaging, cosmetic, as well as other household, commercial, and industrial containers.

[0280] In one embodiment, the compositions of the present disclosure are useful as plastics, films, fibers, and sheet. The compositions of this disclosure are useful as molded or shaped articles, molded or shaped parts or as solid plastic objects. In one embodiment, the compositions of this disclosure are useful as molded parts or molded articles. The compositions are suitable for use in any applications where clear, hard plastics are required. Examples of such parts and articles include cutlery, disposable cutlery, cutlery handles, disposable knives, forks, spoons, plates, cups, straws, jars, cosmetics packaging, lids, decorative lids, personal care product packaging, eyeglass frames, ophthalmic lenses, toothbrushes, toothbrush handles, toys, utensils, tools, tool handles, camera parts, parts of electronic devices, razor parts, ink pen barrels, disposable syringes, bottles, bottle caps, shelving, shelving dividers, electronics housing, electronic equipment cases, computer monitors, printers, keyboards, pipes, automotive parts, automotive interior parts, automotive trim, signs, outdoor signs, skylights, thermoformed letters, siding, toys, toy parts, thermally conductive plastics, medical devices, dental trays, dental appliances, containers, food containers, shipping containers, packaging, furniture components, multiwall film, multilayer film, insulated parts, insulatedarticles, insulated containers, trays, food trays, food pans, tumblers, storage boxes, food processors, blender and mixer bowls, water bottles, crisper trays, washing machine parts, refrigerator parts, vacuum cleaner parts, thermally conductive plastics, healthcare supplies, commercial foodservice products, boxes, films for graphic arts applications, plastic films for plastic glass laminates, point of purchase displays, smoke vents, laminated cards, fenestration, glazing, partitions, ceiling tiles, lighting, machine guards, graphic arts, lenticular, extrusion laminated sheets or films, decorative laminates, office furniture, face shields, medical packaging, sign holders on point of display shelving, and shelf price holds, and the like.

[0281] In some embodiments, the r-articles as described herein useful as films, containers, packaging articles, appliance parts, cosmetic jars, bottles, medical containers, personal care containers, cosmetics containers, molded articles, lids, fragrance caps, tools, tool handles, toothbrushes, toothbrush handles, electronic and / or acoustic device housings, medical devices, medical packaging, healthcare supplies, commercial foodservice products, trays, containers, food pans, tumblers, storage boxes, bottles, food processors, blenderand mixer bowls, utensils, waterbottles, crisper trays, washing machine parts, refrigerator parts, vacuum cleaner parts, ophthalmic lenses and frames and / or toys.

[0282] Any suitable processing method can be used to form the r-articles described herein including, but not limited to, injection blow molding, injection stretch blow molding, extrusion blow molding, extrusion stretch blow molding, compression molding, extrusion molding (extrusion), calendering, and even 3D printing (additive manufacturing). Methods of making molded articles include but are not limited to thermoforming, injection molding, extrusion, injection blow molding, injection stretch blow molding, and extrusion blow molding. The processes of this disclosure can include any thermoforming processes known in the art. The processes of this disclosure can include any blow molding processes known in the art including, but not limited to, extrusion blow molding, extrusion stretch blow molding, injection blow molding, and injection stretch blow molding.

[0283] Prior to processing the blended r-PET composition or any of the r-polyesters described herein to form an r-article, one or more additives suchas stabilizers, pigments, flame retardants, fillers, reinforcing agents, and / or processing aids may be added, but in amounts that do not significantly alter the properties of the final r-article. The r-articles formed from the r-PET blend composition or other r-polyesters may have one or more of the properties described previously with respect to the r-PET blend composition or r-polyesters.

[0284] This disclosure includes any injection blow molding manufacturing process known in the art. Although not limited thereto, a typical description of injection blow molding (IBM) manufacturing process involves: 1) melting the composition in a reciprocating screw extruder; 2) injecting the molten composition into an injection mold to form a partially cooled tube closed at one end (i.e. a preform); 3) moving the preform into a blow mold having the desired finished shape around the preform and closing the blow mold around the preform; 4) blowing air into the preform, causing the preform to stretch and expand to fill the mold; 5) cooling the molded article; 6) ejecting the article from the mold.

[0285] This disclosure includes any injection stretch blow molding manufacturing process known in the art. Although not limited thereto, a typical description of injection stretch blow molding (ISBM) manufacturing process involves: 1) melting the composition in a reciprocating screw extruder; 2) injecting the molten composition into an injection mold to form a partially cooled tube closed at one end (i.e. a preform); 3) moving the preform into a blow mold having the desired finished shape around the preform and closing the blow mold around the preform; 4) stretching the preform using an interior stretch rod, and blowing air into the preform causing the preform to stretch and expand to fill the mold; 5) cooling the molded article; 6) ejecting the article from the mold.

[0286] This disclosure includes any extrusion blow molding manufacturing process known in the art. Although not limited thereto, a typical description of extrusion blow molding manufacturing process involves: 1) melting the composition in an extruder; 2) extruding the molten composition through a die to form a tube of molten polymer (i.e. a parison); 3) clamping a mold having the desired finished shape around the parison; 4) blowing air into the parison, causing the extrudate to stretch and expand to fill the mold; 5)cooling the molded article; 6) ejecting the article of the mold; and 7) removing excess plastic (commonly referred to as flash) from the article.EXAMPLES

[0287] The following examples set forth methods in accordance with the disclosure. It is to be understood, however, that these examples are provided by way of illustration, and nothing therein should be taken as a limitation upon the overall scope.Example 1

[0288] This example provides a comparison of the compositional profiles of several dimethyl terephthalate (DMT) compositions. Comparative Sample A is virgin DMT commercially available from Eastman Chemical Company. Comparative Sample B is a recycled content DMT formed by depolymerizing waste PET in a glycolysis step followed by a methanolysis step. The resulting depolymerized material was crystallized and then melted. Comparative Sample B was taken from the molten r-DMT in the melt vessel. The remaining molten r-DMT was then subjected to reactive distillation in a column having 3 theoretical stages. The overhead stream withdrawn from the column was purified r-DMT, a portion of which was withdrawn as Disclosed Sample C.

[0289] Each of Comparative Sample A, Comparative Sample B, and Disclosed Sample C were subjected to several analysis to determine the compositions of each sample. GC-FID was used to determine the amount of free ethylene glycol, methanol, and DMT, while ICP-MS was used to determine the antimony content after full digestion in a strong hot acid. Finally, HPLC was used to determine the presence of MHT, MFB, DMP, BHET, and MHET. Each analysis was reproduced four times. Table 1 , below, summarizes the results of these analyses.Table 1: Compositional Profiles of Several DMT CompositionsExample 2

[0290] Each of the DMT compositions described in Example 1 above were used to form different types of polyester. First, each of the Comparative Sample A, Comparative Sample B, and Disclosed Sample C DMT compositions were polymerized with ethylene glycol and cyclohexane dimethanol under the same conditions. The resulting polyesters (Comparative Polyester A-1, Comparative Polyester B-1 , and Disclosed Polyester C-1) included 100 mole percent dimethyl terephthalate residues and 69 mole percent of ethylene glycol and 31 mole percent of cyclohexane dimethanol, based on the total moles of diol residues in the polyesters.

[0291] Next, additional polyesters were formed by polymerizing each of Comparative Sample A, Comparative Sample B, and Disclosed Sample C with cyclohexane dimethanol and 2,2,4,4-tetramethyl-1 ,3-cyclobutanediol under the same conditions. The resulting polyesters (Comparative Polyester A-2, Comparative Polyester B-2, and Disclosed Polyester C-2) included 100 mole percent dimethyl terephthalate residues and 65 mole percent of cyclohexane dimethanol and 35 mole percent of 2, 2, 4, 4-tetramethyl-1 ,3-cyclobutanediol, based on the total moles of diol residues in the polyesters.

[0292] The inherent viscosity and L*, a*, and b* color values of each of Comparative Polyesters A-1 , B-1, A-2, and B2, as well as Disclosed Polyesters C-1 and C-2 were tested according to the standards described herein. Each sample was tested 4 times, and the results were averaged. The results are summarized in Tables 2a and 2b, below.Table 2a: Properties of Several Polyesters formed from DMT CompositionsTable 2b: Properties of Several Polyesters formed from DMT CompositionsDEFINITIONS

[0293] It should be understood that the following is not intended to be an exclusive list of defined terms. Other definitions may be provided in the foregoing description, such as, for example, when accompanying the use of a defined term in context.

[0294] As used herein, the terms “Cx” or “Cx hydrocarbon” or “Cx component” refers to a hydrocarbon compound including “x” total carbons per molecule, and encompasses all olefins, paraffins, aromatics, heterocyclic, and isomers having that number of carbon atoms. For example, each of normal, iso, and tert-butane and butene and butadiene molecules would fall under the general description “C4” or “C4 components.”

[0295] As used herein, the term “lighter” refers to a component or fraction having a lower boiling point than another component or fraction.

[0296] As used herein, the term “heavier” refers to a component or fraction having a higher boiling point than another component or fraction.

[0297] As used herein, the term “upstream” refers to an item of facility that is positioned prior to another item or facility in a given process flow and may include intervening items and / or facilities.

[0298] As used herein, the term “downstream” refers to an item or facility that is positioned after another item or facility in a given process flow and may include intervening items and / or facilities.

[0299] As used herein, the term “predominantly” means more than 50 percent by weight. For example, a predominantly propane stream, composition, feedstock, or product is a stream, composition, feedstock, or product that contains more than 50 weight percent propane.

[0300] As used herein, the term “major portion” has the same meaning as “predominantly.”

[0301] As used herein, the term “waste” with reference to a material or component refers to used, scrap, and / or discarded material.

[0302] As used herein, the term “fluid communication” refers to the direct or indirect fluid connection between two or more processing, storage, or transportation facilities or zones.

[0303] As used herein, the terms “a,” “an,” and “the” mean one or more.

[0304] As used herein, the term “and / or,” when used in a list of two or more items, means that any one of the listed items can be employed by itself or any combination of two or more of the listed items can be employed. For example, if a composition is described as containing components A, B, and / or C, the composition can contain A alone; B alone; C alone; A and B in combination; A and C in combination, B and C in combination; or A, B, and C in combination.

[0305] As used herein, the phrase “at least a portion” includes at least a portion and up to and including the entire amount or time period.

[0306] As used herein, the term “chemical recycling” refers to a waste plastic recycling process that includes a step of chemically converting waste plastic polymers into lower molecular weight polymers, oligomers, monomers, and / or non-polymeric molecules (e.g., hydrogen, carbon monoxide, methane, ethane, propane, ethylene, and propylene) that are useful by themselves and / or are useful as feedstocks to another chemical production process(es).

[0307] As used herein, the terms “comprising,” “comprises,” and “comprise” are open-ended transition terms used to transition from a subject recited before the term to one or more elements recited after the term, where the element or elements listed after the transition term are not necessarily the only elements that make up the subject.

[0308] As used herein, the terms “waste plastic” and “plastic waste” refer to used, scrap, and / or discarded plastic materials.

[0309] As used herein, the term “continuous” means a process wherein the reactants are introduced, and the products are withdrawn simultaneously in an uninterrupted manner.

[0310] As used herein, the term “virgin” refers to a polymeric material that has not been used or processed.

[0311] As used herein, the term “PET” refers to a homopolymer of polyethylene terephthalate, or polyethylene terephthalate modified with modifiers or containing residues or moieties of other than ethylene glycol (EG) and terephthalic acid (or a dimethyl terephthalate), such as isophthalic acid, 1 ,4-cyclohexanedicarboxylic acid, diethylene glycol, TMCD (2, 2,4,4-tetramethyl-1 ,3-cyclobutanediol), CHDM (cyclohexanedimethanol), propyleneglycol, isosorbide, 1 ,4-butanediol, 1 ,3- propane diol, and / or NPG (neopentyl glycol), or polyesters having repeating terephthalate units (and whether or not they contain repeating ethylene glycol based units) and one or more residues or moieties of TMCD (2,2,4,4-tetramethyl-1 ,3-cyclobutanediol), CHDM (cyclohexanedimethanol), propylene glycol, or NPG (neopentyl glycol), isosorbide, isophthalic acid, 1 ,4- cyclohexanedicarboxylic acid, 1 ,4-butanediol, 1,3-propane diol, and / or diethylene glycol, or combinations thereof. PET is defined according to ASTM D5047 as including at least 90 mole percent of polyethylene terephthalate residues and having a melting point of at least 225°C.

[0312] As used herein, the term “recovery percentage (of component A)” in a specific product stream exiting a given process step / zone is defined by the following formula: (Mass of component A in the specific product stream) I (Combined mass of component A introduced into the given process step in all streams), expressed as a percentage.

[0313] As used herein, the term “co-located” refers to the characteristic of at least two objects being situated on a common physical site, and / or within 5, within 2, within 1 , within 0.75, within 0.5, or within 0.25 miles of each other, measured as a straight-line distance between two designated points.

[0314] As used herein, the term “diol” refers to an organic compound including two or more hydroxyl groups (-OH) bonded to saturated carbon atoms. The term “glycol,” refers to an organic compound including two or more hydroxyl groups (-OH) bonded to saturated carbon atoms and is therefore encompassed by the term “diol.” As used herein, the term “alcohol” refers to an organic compound with a single hydroxyl (-OH) group bonded to a saturated carbon atom.

[0315] As used herein, the term “oligomer” refers to a polymeric species comprising in the range of from about 7 to about 50 chain lengths.

[0316] As used herein, the term “monomer” refers to a polymeric species comprising less than about three chain lengths, while the term “polymer” refers to a polymeric species comprising greater than about 50 chain lengths.

[0317] As used herein, “solid state polymerization” refers to a process in which the polymer chain lengths are increased by heating the polyester in the substantial absence of oxygen and water.

[0318] As used herein, the term “predominantly” means at least 50 weight (or mole) percent, as applicable.

[0319] As used herein, the term “residue” refers to the portion of the compound(s) which remains in the oligomer and / or polymer chain after the condensation reaction.CLAIMS NOT LIMITED TO DISCLOSED EMBODIMENTS

[0320] The preferred forms of the invention described above are to be used as illustration only and should not be used in a limiting sense to interpret the scope of the present invention. Modifications to the exemplary embodiments, set forth above, could be readily made by those skilled in the art without departing from the spirit of the present invention.

[0321] The inventors hereby state their intent to rely on the Doctrine of Equivalents to determine and assess the reasonably fair scope of the present invention as it pertains to any apparatus not materially departing from but outside the literal scope of the invention as set forth in the following claims.ADDITIONAL CLAIM SUPPORTING DESCRIPTION

[0322] In one embodiment, there is provided a process for chemically recycling waste plastic, the process comprising: (a) depolymerizing a waste plastic feed stream comprising polyethylene terephthalate (PET) in a depolymerization zone to thereby provide a terephthalate-containing depolymerization stream comprising recycled content dimethyl terephthalate (r-DMT); (b) crystallizing at least a portion of the terephthalate-containing depolymerization stream in a crystallization zone to thereby form a crude r-DMT solids stream; (c) melting at least a portion of the crude r-DMT solids stream in a melting zone to provide a molten crude r-DMT stream comprising r-DMT and one or more non-DMT impurities; and (d) distilling at least a portion of the molten crude r-DMT stream in a reactive distillation zone to thereby provide a purified r-DMT stream comprising a higher concentration of r-DMT than themolten crude r-DMT stream introduced into the reactive distillation zone, wherein the purified r-DMT stream comprises an amount of elemental antimony of less than 1 part per million by weight (ppm) and / or a free ethylene glycol (EG) content of not more than 250 ppm.

[0323] In one embodiment, there is provided a process for chemically recycling waste plastic, the process comprising: (a) depolymerizing a waste plastic feed stream comprising polyethylene terephthalate (PET) in a depolymerization zone to thereby provide a terephthalate-containing depolymerization stream comprising recycled content dimethyl terephthalate (r-DMT); (b) crystallizing at least a portion of the terephthalate-containing depolymerization stream in a crystallization zone to thereby form a crude r-DMT solids stream; (c) melting at least a portion of the crude r-DMT solids stream in a melting zone to provide a molten crude r-DMT stream comprising r-DMT and one or more non-DMT impurities; and (d) introducing a catalyst into the molten crude r-DMT stream, wherein the catalyst is selected to facilitate chemical reaction between two or more components within the molten crude r-DMT; and (e) distilling at least a portion of the molten crude r-DMT stream in a distillation zone to thereby provide a purified r-DMT product stream, wherein the purified r-DMT stream comprises an amount of elemental antimony of less than 1 part per million by weight (ppm) and / or a free ethylene glycol (EG) content of not more than 250 ppm.

[0324] In one embodiment, there is provided a process for chemically recycling waste plastic, the process comprising: (a) depolymerizing a waste plastic feed stream comprising polyethylene terephthalate (PET) in a depolymerization zone to thereby provide a terephthalate-containing depolymerization stream comprising recycled content dimethyl terephthalate (r-DMT); (b) crystallizing at least a portion of the terephthalate-containing depolymerization stream in a crystallization zone to thereby form a crude r-DMT solids stream; (c) melting at least a portion of the crude r-DMT solids stream in a melting zone to provide a molten crude r-DMT stream comprising r-DMT and one or more non-DMT impurities; and (d) purifying at least a portion of the molten crude r-DMT stream in a purification zone to thereby provide a purified r-DMT product stream, wherein the non-DMT impurities comprise free ethylene glycol (free EG) and wherein the purifying removes at least a portion of the freeEG such that the amount of free EG in the purified r-DMT product stream is less than 50 percent by weight of the amount of free EG in the molten crude r-DMT, wherein the purified r-DMT stream comprises an amount of elemental antimony of less than 1 part per million by weight (ppm) and / or a free ethylene glycol (EG) content of not more than 250 ppm.

[0325] In one embodiment, there is provided a recycled content dimethyl terephthalate (r-DMT) composition formed by depolymerization of waste polyethylene terephthalate (PET), the composition comprising: at least 95 weight percent of dimethyl terephthalate having recycled content (r-DMT); from 1 part per billion by weight (ppb) to 500 ppb of elemental antimony (Sb); and less than about 500 parts per million of total ethylene glycol (total EG), wherein all amounts are based on the total weight of the composition.

[0326] In one embodiment, there is provided a recycled content dimethyl terephthalate (r-DMT) composition formed by depolymerization of waste polyethylene terephthalate (PET), the composition comprising: at least 95 weight percent of dimethyl terephthalate having recycled content (r-DMT); from 1 ppb to 500 ppb of elemental antimony (Sb); not more than about 250 ppm of free ethylene glycol; not more than 700 ppm of mono(2-hydroxyethyl) terephthalate (MHET); from 7.5 ppm to 500 ppm of methyl hydrogen terephthalate (MHT), wherein all amounts are based on the total weight of the composition.

[0327] In one embodiment, there is provided a process for chemically recycling waste plastic, the process comprising: (a) depolymerizing a feed stream comprising waste polyethylene terephthalate (PET) to thereby provide a terephthalate-containing depolymerization stream; (b) crystallizing at least a portion of the terephthalate-containing depolymerization stream to thereby form a crystallized crude recycled content dimethyl terephthalate (r-DMT); (c) melting at least a portion of the crystallized crude r-DMT to thereby form a molten crude r-DMT stream that comprises r-DMT and one or more non-DMT impurities; and (d) purifying at least a portion of the molten crude r-DMT stream in a purification zone to thereby provide a purified r-DMT stream, wherein the purified r-DMT stream comprises: at least 95 percent by weight of dimethyl terephthalate; from 1 part per billion by weight (ppb) to 500 ppb of elemental antimony (Sb); and less than about 500 parts per million by weight (ppm) oftotal ethylene glycol (total EG), wherein all amounts are based on the total weight of the r-DMT stream.

[0328] In one embodiment, there is provided a recycled content dimethyl terephthalate (r-DMT) composition formed by depolymerization of waste polyethylene terephthalate (PET), the composition comprising at least 95 weight percent of dimethyl terephthalate having recycled content (r-DMT); and from 1 part per billion by weight (ppb) and 500 ppb of elemental antimony, wherein all amounts are based on the total weight of the composition.

[0329] In one embodiment, there is provided a recycled content dimethyl terephthalate (r-DMT) composition formed by depolymerization of waste polyethylene terephthalate (PET), the composition comprising: at least 97.5 weight percent of dimethyl terephthalate having recycled content (r-DMT); from 1 ppb to 250 ppb of elemental antimony (Sb); and from about 7.5 ppm to about 500 ppm of methyl hydrogen terephthalate (MHT), wherein all amounts are based on the total weight of the composition.

[0330] In one embodiment, there is provided a process for chemically recycling waste plastic, the process comprising: (a) depolymerizing a feed stream comprising waste polyethylene terephthalate (PET) to thereby provide a terephthalate-containing depolymerization stream; (b) crystallizing at least a portion of the terephthalate-containing depolymerization stream to thereby form a crystallized crude recycled content dimethyl terephthalate (r-DMT); (c) melting at least a portion of the crystallized crude r-DMT to thereby form a molten crude r-DMT stream that comprises r-DMT and one or more non-DMT impurities; and (d) purifying at least a portion of the molten crude r-DMT stream in a purification zone to thereby provide a purified r-DMT stream, wherein the purified r-DMT stream comprises at least 95 percent by weight dimethyl terephthalate, and wherein the purified r-DMT stream comprises between 1 part per billion by weight (ppb) and 500 ppb of elemental antimony (Sb), based on the total weight of the purified r-DMT stream.

[0331] In one embodiment, there is provided a recycled content dimethyl terephthalate (r-DMT) composition formed by depolymerization of waste polyethylene terephthalate (PET), wherein the r-DMT composition comprises at least 95 weight percent of dimethyl terephthalate having recycled content (r-DMT); less than about 250 ppm of free ethylene glycol (free EG); andgreater than 7.5 ppm and less than 500 ppm of methyl hydrogen terephthalate (MHT), wherein all amounts are based on the total weight of the composition.

[0332] In one embodiment, there is provided a recycled content dimethyl terephthalate (r-DMT) composition formed by depolymerization of waste polyethylene terephthalate (PET), wherein the r-DMT composition comprises: at least 97.5 weight percent of dimethyl terephthalate having recycled content (r-DMT); less than 45 parts per million by weight (ppm) of dimethyl phthalate (DMP); less than 5 ppm of methyl formyl benzoate (MFB); less than 690 ppm of mono(2-hydroxyethyl) terephthalate (MHET); less than about 250 ppm of free ethylene glycol (free EG); and greater than 7.5 ppm and less than 500 ppm of methyl hydrogen terephthalate (MHT), wherein all amounts are based on the total weight of the r-DMT composition.

[0333] In one embodiment, there is provided a process for chemically recycling waste plastic, the process comprising: (a) depolymerizing a feed stream comprising waste polyethylene terephthalate (PET) to thereby provide a terephthalate-containing depolymerization stream; (b) crystallizing at least a portion of the terephthalate-containing depolymerization stream to thereby form a crystallized crude recycled content dimethyl terephthalate (r-DMT); (c) melting at least a portion of the crystallized crude r-DMT to thereby form a molten crude r-DMT stream that comprises r-DMT and one or more non-DMT impurities; and (d) purifying at least a portion of the molten crude r-DMT stream in a purification zone to thereby provide a purified r-DMT stream, wherein the purified r-DMT stream comprises at least 95 percent by weight dimethyl terephthalate; less than about 250 ppm of free ethylene glycol (free EG); and methyl hydrogen terephthalate (MHT) in an amount of 7.5 ppm to about 500 ppm, wherein all amounts are based on the total weight of the purified r-DMT stream.

[0334] In one embodiment, there is provided a recycled content dimethyl terephthalate (r-DMT) composition formed by depolymerization of waste polyethylene terephthalate (PET), the composition comprising: at least 95 weight percent of dimethyl terephthalate having recycled content (r-DMT); less than 250 parts per million by weight (ppm) of free ethylene glycol (EG); less than 700 ppm of mono(2-hydroxyethyl) terephthalate (MHET); and at least1 part per billion by weight (ppb) of elemental antimony, wherein all amounts are based on the total weight of the composition.

[0335] In one embodiment, there is provided a recycled content dimethyl terephthalate (r-DMT) composition formed by depolymerization of waste polyethylene terephthalate (PET), the composition comprising: at least 97.5 weight percent of dimethyl terephthalate having recycled content (r-DMT); from about 1 part per billion by weight (ppb) to less than 1 part per million by weight (ppm) of elemental antimony (Sb); and less than 500 ppm of mono(2-hydroxyethyl) terephthalate (MHET), wherein all amounts are based on the total weight of the r-DMT composition.

[0336] In one embodiment, there is provided a process for chemically recycling waste plastic, the process comprising: (a) depolymerizing a feed stream comprising waste polyethylene terephthalate (PET) to thereby provide a terephthalate-containing depolymerization product stream; (b) crystallizing at least a portion of the terephthalate-containing depolymerization product stream to thereby form a crystallized crude recycled content dimethyl terephthalate (r-DMT); (c) melting at least a portion of the crystallized crude r-DMT to thereby form a molten crude r-DMT stream that comprises r-DMT and one or more non-DMT impurities; and (d) purifying at least a portion of the molten crude r-DMT stream in a purification zone to thereby provide a purified r-DMT stream, wherein the purified r-DMT stream comprises at least 95 weight percent of dimethyl terephthalate having recycled content (r-DMT); not more than 250 parts per million by weight (ppm) of free ethylene glycol (EG); less than 700 ppm of mono(2-hydroxyethyl) terephthalate (MHET); and at least 1 part per billion by weight (ppb) of elemental antimony.

[0337] In one embodiment, there is provided a recycled content polyester (r-polyester) formed from recycled content dimethyl terephthalate (r-DMT) produced by depolymerization of waste plastic, the r-polyester comprising: (a) a diester component comprising: (i) from 70 to about 100 mole percent of residues of r-DMT; (ii) from 0 to 30 mole percent of residues of at least one modifying diester, wherein each of (i) and (ii) are based on the total moles of diester residues in the r-polyester; and (b) a diol component comprising: (i) from 1 to 99 mole percent of residues of 2,2,4,4-tetramethyl-1 ,4-cyclobutanediol (TMCD); and (ii) from 1 to 99 mole percent of residues of atleast one additional diol chosen from cyclohexanedimethanol (CHDM), ethylene glycol (EG), or combinations thereof, wherein each of (i) and (ii) are based on the total moles of diol residues in the r-polyester; and (c) elemental antimony in an amount in the range of from 1 part per billion by weight (ppb) to 850 ppb, based on the total weight of the r-polyester.

[0338] In one embodiment, there is provided a recycled content polyester (r-polyester) formed from recycled content dimethyl terephthalate (r-DMT) produced by depolymerization of waste plastic, the r-polyester comprising: (a) a diester component comprising (i) at least 95 mole percent of residues of r-DMT; and (ii) not more than 5 mole percent of residues of at least one modifying diester, wherein (i) and (ii) are based on the total moles of diester residues in the r-polyester; (b) a diol component comprising (i) or (ii): (i) from about 10 to about 65 mole percent of residues of TMCD and about 35 to about 90 mole percent of residues of CHDM; or (ii) from about 55 to about 99 mole percent of residues of EG and about 1 to about 45 mole percent of residues of TMCD, wherein (i) and (ii) are based on the total moles of diol residues in the r-polyester; and (c) elemental antimony (Sb) in an amount in the range of from 1 part per billion by weight (ppb) to 750 ppb, based on the total weight of the r-polyester.

[0339] In one embodiment, there is provided a process for producing recycled content polyester (r-polyester), the process comprising: (a) introducing reactants comprising recycled content dimethyl terephthalate (r-DMT), 2, 2,4,4-tetramethyl-1 ,4-cyclobutanediol (TMCD), and at least one additional diol chosen from cyclohexanedimethanol (CHDM) and ethylene glycol (EG) into a transesterification zone; (b) transesterifying at least a portion of the r-DMT, the TMCD, and the additional diol in the transesterification zone to thereby form a recycled content polyester oligomer (r-polyester oligomer); and (c) polycondensing at least a portion of the r-polyester oligomer in a polycondensation zone to thereby form a recycled content polyester (r-polyester), wherein the r-DMT introduced into the transesterification zone comprises (i) at least 95 weight percent of dimethyl terephthalate having recycled content (r-DMT); (ii) elemental antimony in an amount of at least 1 part per billion by weight (ppb) and less than 1 part per million by weight (ppm); (iii) at least one of the following (A) to (C): (A) less than 45 ppm of dimethylphthalate (DMP); (B) less than 700 ppm of mono(2-hydroxyethyl) terephthalate (MHET); and (C) less than 500 ppm of methyl hydrogen terephthalate (MHT).

[0340] In one embodiment, there is provided a recycled content copolyester (r-polyester) comprising: (a) a diester component comprising residues of recycled content dimethyl terephthalate (r-DMT); and (b) a diol component comprising (i) at least 20 mole percent of residues of cyclohexanedimethanol (CHDM); (ii) not more than 75 mole percent of residues of ethylene glycol (EG); and (iii) less than 5 mole percent of residues of diols other than CHDM and EG, wherein each of (i) through (iii) are based on the total moles of diol residues present in the r-polyester, and wherein the r-polyester has an elemental antimony content in the range of from 1 part per billion by weight (ppb) to 850 ppb, based on the total weight of the r-polyester.

[0341] In one embodiment, there is provided a recycled content polyester (r-polyester) comprising: (a) a diester component comprising residues of recycled content dimethyl terephthalate (r-DMT); (b) a diol component comprising (i) about 25 to 100 mole percent of residues of cyclohexanedimethanol (CHDM); (ii) 0 to about 75 mole percent of residues of ethylene glycol (EG); and (iii) less than 3 mole percent of residues of glycols other than CHDM and EG, wherein each of (i) through (iii) are based on the total moles of diol residues present in the r-polyester, and wherein said r-polyester has an elemental antimony content in the range of from 1 part per billion by weight (ppb) to 500 ppb, based on the total weight of r-polyester.

[0342] In one embodiment, there is provided a process for producing recycled content polyester (r-polyester), the process comprising: (a) introducing dimethyl terephthalate comprising recycled content (r-DMT) and cyclohexanedimethanol (CHDM) into a transesterification zone; (b) transesterifying at least a portion of the r-DMT with at least a portion of the CHDM in the transesterification zone to thereby form a recycled content polyester oligomer (r-polyester oligomer); and (c) polycondensing at least a portion of the r-polyester oligomer in a polycondensation zone to thereby form a recycled content polyester (r-polyester), wherein the r-DMT introduced into the transesterification zone comprises: (i) at least 95 weight percent of dimethyl terephthalate having recycled content (r-DMT); (ii) elemental antimony in an amount of at least about 1 part per billion by weight (ppb) and less than 1 partper million by weight (ppm); (iii) at least one of the following (A) through (C): (A) less than 45 ppm of dimethyl phthalate (DMP); (B) less than 700 ppm of mono(2-hydroxyethyl) terephthalate (MHET); and (C) less than 500 ppm of methyl hydrogen terephthalate (MHT), wherein all amounts are based on the total weight of the r-DMT introduced into the transesterification zone.

[0343] In one embodiment, there is provided a recycled content polyethylene terephthalate (r-PET) formed from recycled content dimethyl terephthalate (r-DMT), the r-PET comprising: (a) a diester component comprising residues of recycled content (r-DMT); (b) a diol component comprising residues of ethylene glycol (EG); wherein the r-PET has an elemental antimony content in the range of from 1 part per billion by weight (ppb) to 850 ppb, based on the total weight of the r-PET.

[0344] In one embodiment, there is provided a process for producing recycled content polyester (r-PET), the process comprising: (a) introducing dimethyl terephthalate having recycled content (r-DMT), ethylene glycol, and optionally at least one additional diol other than ethylene glycol into a transesterification zone; (b) transesterifying at least a portion of the dimethyl terephthalate, the ethylene glycol, and, when present, the additional diol other than ethylene glycol in the transesterification zone to thereby form a recycled content polyester oligomer (r-PET oligomer); and (c) polycondensing at least a portion of the r-PET oligomer in a polycondensation zone to thereby form a recycled content polyester (r-PET), wherein the r-DMT introduced into the transesterification zone comprises (i) at least 95 weight percent of dimethyl terephthalate having recycled content (r-DMT); (ii) from about 1 part per billion by weight (ppb) to less than 1 part per million by weight (ppm) of elemental antimony; (iii) at least one of the following (A) through (C): (A) less than 45 ppm of dimethyl phthalate (DMP); (B) less than 700 ppm of mono(2-hydroxyethyl) terephthalate (MHET); and (C) less than 500 ppm of methyl hydrogen terephthalate (MHT).

[0345] In one embodiment, there is provided a recycled content polyester (r-polyester) formed from recycled content dimethyl terephthalate (r-DMT), the r-polyester comprising (a) a diester component comprising residues of recycled content dimethyl terephthalate (r-DMT); and (b)a diol component comprising at least 1 mole percent of isosorbide residues, wherein the r-polyester has an elemental antimony content in the range of from 1 part per billion by weight (ppb) to 1 part per million (ppm), based on the total weight of the r-polyester.

[0346] In one embodiment, there is provided a process for producing recycled content polyester (r-polyester), the process comprising: (a) introducing dimethyl terephthalate comprising recycled content dimethyl terephthalate (r-DMT) and at least one diol comprising isosorbide into a transesterification zone; (b) transesterifying at least a portion of the r-DMT and the diol in the transesterification zone to thereby form a recycled content polyester oligomer (r-polyester oligomer); and (c) polycondensing at least a portion of the r-polyester oligomer in a polycondensation zone to thereby form a recycled content polyester (r-polyester), wherein the r-DMT introduced into the transesterification zone comprises (i) at least 95 weight percent of dimethyl terephthalate having recycled content (r-DMT); (ii) from about 1 part per billion by weight (ppb) to less than 1 part per million by weight (ppm) of elemental antimony; and (iii) at least one of the following (A) through (C): (A) less than 45 ppm of dimethyl phthalate (DMP); (B) less than 700 ppm of mono(2-hydroxyethyl) terephthalate (MHET); and (C) less than 500 ppm of methyl hydrogen terephthalate (MHT), wherein all amounts are based on the total weight of the composition.

[0347] In one embodiment, there is provided a recycled content polyethylene terephthalate (r-PET) composition having a recycled content of greater than 50 percent and a haze value of at least 2% and not more than 20%, measured according to ASTM D-1003 using a 1 / 8-inch thick plaque.

[0348] In one embodiment, there is provided a recycled content polyethylene terephthalate (r-PET) composition having a recycled content of greater than 50 percent, wherein the r-PET composition comprises: (a) at least one characteristic (i) or (ii): (i) from about 0.2 to about 3 percent of methyl end groups based on the total number of end groups, as determined by NMR; and (ii) from about 0.1 to about 10 mole percent of residues of cyclohexanedimethanol (CHDM), based on the total moles of diol residues in the r-PET composition; (b) at least one characteristic (iii) to (v): (iii) at least 5 parts per million by weight (ppm) of total chloride (Cl); (iv) at least 5 ppm of totalnitrogen (N); and (v) a haze value of at least 2%, measured by ASTM D-1003 with a 1 / 8-inch plaque.

[0349] In one embodiment, there is provided a recycled content polyethylene terephthalate (r-PET) composition having a recycled content of at least 10 percent, wherein the r-PET composition comprises one or both of (a) and (b): (a) an amount of total chloride (Cl) at least 5 parts per million by weight (ppm) and less than 15 ppm; and / or (b) an amount of total nitrogen (N) at least 5 ppm and less than 15 ppm, wherein each amount (a) and (b) is based on the total weight of the r-PET composition, and wherein the r-PET composition does not include 100 weight percent of mechanically recycled PET (mr-PET).

[0350] In one embodiment, there is provided a recycled content PET (r-PET) composition comprising: 5 to 75 weight percent chemically recycled PET (cr-PET); 5 to 75 weight percent mechanically recycled PET (mr-PET); and optionally, 5 to 45 weight percent of virgin PET, wherein the combined amount of cr-PET, mr-PET, and virgin PET, when present, are at least 95 weight percent of the r-PET composition.

[0351] In one embodiment, there is provided a recycled content PET (r-PET) composition comprising at least 5 weight percent of chemically recycled PET (cr-PET), at least 5 weight percent of mechanically recycled PET (mr-PET), and optionally at least 5 weight percent of virgin PET, wherein the r-PET composition has a total recycled content of greater than 50%, wherein the combined amount of cr-PET, mr-PET, and virgin PET, when present, are at least 95 weight percent of the composition, and wherein the r-PET composition has one or both of the following properties (i) and / or (ii): (i) an L* value of at least 80, measured according to 1976 CIE L*a*b* Color Space; and / or (ii) a haze value of less than 20 percent, measured according to ASTM D-1003 Method A with a 1 / 8-inch plaque.

[0352] In one embodiment, there is provided a recycled content polyethylene terephthalate (r-PET) composition comprising at least 5 weight percent of chemically recycled PET (cr-PET), at least 5 weight percent of mechanically recycled PET (mr-PET), and at least 5 weight percent of virgin PET, wherein the r-PET composition has a total recycled content of greater than 50%, wherein the combined amount of cr-PET, mr-PET, and virgin PET are at least 95 weight percent of the composition, and wherein the r-PET compositionhas one or both of the following properties (i) and / or (ii): (i) an L* value, measured according to 1976 CIE L*a*b* Color Space, within about 15 of the L* value of the virgin PET; and / or (ii) a haze value, measured according to ASTM D-1003 with a 1 / 8-inch plaque, within about 20 percent of the haze value of the virgin PET.

[0353] In one embodiment, there is provided a method of making a recycled content polyethylene terephthalate (r-PET) composition, said method comprising mixing mechanically recycled PET (mr-PET) and chemically recycled PET (cr-PET) to form a blended r-PET composition.

[0354] In one embodiment, there is provided a method of making a recycled content polyethylene terephthalate (r-PET) composition, the method comprising: (a) setting a target value for at least one property of the r-PET composition; (b) blending mechanically recycled PET (mr-PET) and virgin PET to provide a first r-PET blend; (c) measuring a value of the property in (a) for the first r-PET blend to provide a first measured value; (d) comparing the first measured value with the target value to determine a first difference; (e) based on the first difference, mixing an amount of chemically recycled PET (cr-PET) with an amount of mechanically recycled PET (mr-PET) to form a second r-PET blend; (f) measuring a value of the property in (a) for the second r-PET blend to provide a second measured value; (g) comparing the second measured value with the target value to determine a second difference; and (h) when the second difference is greater than 50 percent of the target value, repeating (e) through (g) until the second difference is 50 percent or less of the target value, as determined by the formula: absolute value of (target value - second measured value) I target value, expressed as a percent.

[0355] In one embodiment, there is provided a recycled content article of manufacture (r-article) formed from a recycled content polyethylene terephthalate (r-PET) composition, wherein r-article has a recycled content of greater than 50 percent and has a haze value, measured according to ASTM D-1003 using a 1 / 8-in thick plaque, of at least 2% and not more than 20%.

[0356] In one embodiment, there is provided a recycled content plastic article (r-article) formed from a recycled content polyethylene terephthalate (r-PET) composition, said r-article having a recycled content of greater than 50 percent, wherein the article comprises: (a) at least one characteristic (i) or (ii):(i) from about 0.2 to about 3 percent of methyl end groups based on the total number of end groups, as determined by NMR; (ii) from about 0.1 to about 10 mole percent of residues of cyclohexanedimethanol (CHDM), based on the total moles of diol residues in the r-PET composition; and (b) at least one characteristic (iii) to (v): (iii)at least 5 parts per million by weight (ppm) of total chloride (Cl); (iv) at least 5 ppm of total nitrogen (N); and (v) a haze value of at least 3%, measured byASTM D-1003 with a 1 / 8-inch plaque.

[0357] In one embodiment, there is provided a recycled content plastic article (r-article) formed from a recycled content polyethylene terephthalate (r-PET) composition, said r-article having a recycled content of at least 10 percent and wherein the r-article composition comprises one or both of (a) and (b): (a) an amount of total chloride (Cl) at least 5 parts per million by weight (ppm) and less than 15 ppm; and / or (b) an amount of total nitrogen (N) at least 5 ppm and less than 15 ppm, wherein each amount (a) and (b) is based on the total weight of the r-article, and wherein the r-article is not formed from 100 weight percent of mechanically recycled PET (mr-PET).

[0358] In one embodiment, there is provided a recycled content plastic article (r-article) formed from a recycled content polyethylene terephthalate (r-PET) composition comprising: 5 to 75 weight percent chemically recycled PET (cr-PET); 5 to 75 weight percent mechanically recycled PET (mr-PET); and optionally, 5 to 45 weight percent of virgin PET, wherein the combined amount of cr-PET, mr-PET, and virgin PET, when present, are at least 95 weight percent of the r-PET composition.

[0359] In one embodiment, there is provided a recycled content plastic article (r-article) formed from a recycled content polyethylene terephthalate (r-PET) composition comprising at least 5 weight percent of chemically recycled PET (cr-PET), at least 5 weight percent of mechanically recycled PET (mr-PET), and optionally at least 5 weight percent of virgin PET, wherein the r-PET composition has a total recycled content of greater than 50%, wherein the combined amount of cr-PET, mr-PET, and virgin PET, when present, are at least 95 weight percent of the composition, and wherein the r-article has one or both of the following properties (i) and / or (ii): (i) an L* value of at least 80, measured according to 1976 CIE L*a*b* Color Space; and / or (ii) a haze value of less than20 percent, measured according to ASTM D-1003 Method A using a 1 / 8-inch plaque.

[0360] In one embodiment, there is provided a recycled content plastic article (r-article) formed from a recycled content polyethylene terephthalate (r-PET) composition comprising at least 5 weight percent of chemically recycled PET (cr-PET), at least 5 weight percent of mechanically recycled PET (mr-PET), and at least 5 weight percent of virgin PET, wherein the combined amount of cr-PET, mr-PET, and virgin PET are at least 95 weight percent of the composition, wherein the r-PET composition has a total recycled content of greater than 50%, and wherein the r-article has one or both of the following properties (i) and / or (ii): (i) an L* value, measured according to 1976 CIE L*a*b* Color Space, within about 15 of the L* value of the virgin PET; and / or (ii) a haze value, measured according to ASTM D-1003 with a 1 / 8-inch plaque, within about 20 percent of the haze value of the virgin PET.

[0361] The embodiments described in the preceding paragraphs can also include one or more of the additional aspects / features listed in the following paragraphs. Each of the below additional features can be standalone features or can be combined with one or more of the other additional features to the extent consistent. Thus, to the extent consistent, any of the below features may be combined, alone or with one or more other features, with any of the above embodiments. Note that the values in parenthesis denote alternate upper and / or lower limits to the ranges provided, as appropriate. It should be understood that the phrase “at least about” and / or “not more than about” apply equally to all values provided in parenthesis as applicable.

[0362] Any of the embodiments listed herein, wherein the waste plastic feed stream in (a) comprises at least about 75 (80, 85, 90, 92, 95, 97, 98, 98.5, 99, 99.5, or 99.9) percent polyethylene terephthalate (PET), based on the total weight of the waste plastic feed stream introduced into the depolymerization zone.

[0363] Any of the embodiments listed herein, wherein the waste plastic feed stream in (a) comprises not more than about 25 (20, 15, 10, 5, 3, 2, 1,5, 1 , 0.5, or 0.1 ) weight percent of components other than PET, based on the total weight of the waste plastic feed stream introduced into the depolymerization zone.

[0364] Any of the embodiments listed herein, wherein the components other than PET comprise one or more non-polyester polymers chosen from polyvinyl chloride (PVC), polycarbonate (PC), nylon, elastane, polyolefins (PO) such as polyethylene (PE) and / or polypropylenes (PP), or combinations thereof.

[0365] Any of the embodiments listed herein, wherein the components other than PET comprise non-polymeric materials.

[0366] Any of the embodiments listed herein, wherein the non-polymeric materials comprise organic non-polymeric materials (e.g., cotton, cellulosic fibers, paper, cardboard, wood, food, dirt, etc.) and / or inorganic non-polymeric materials (e.g., metal, glass, etc.).

[0367] Any of the embodiments listed herein, wherein the waste plastic feed stream in (a) has a total moisture content of at least about 0.01 (0.05 or 1 ) weight percent and / or not more than about 10 (8, 5, 3, 2, or 1) weight percent, based on the total weight of the stream.

[0368] Any of the embodiments listed herein, wherein the waste plastic feed stream in (a) comprises post-consumer PET.

[0369] Any of the embodiments listed herein, wherein the waste plastic feed stream in (a) comprises post-industrial PET.

[0370] Any of the embodiments listed herein, wherein the waste plastic feed stream in (a) comprises less than about 1 (0.5, 0.1, 0.05, or 0.01) weight percent of virgin PET, based on the total weight of the stream.

[0371] Any of the embodiments listed herein, wherein the waste plastic feed stream of (a) comprises PET fibers.

[0372] Any of the embodiments listed herein, wherein the waste plastic feed stream of (a) comprises PET flakes, pellets, or fines.

[0373] Any of the embodiments listed herein, wherein the waste plastic feed stream of (a) comprises PET films or sheets.

[0374] Any of the embodiments listed herein, wherein the PET comprises less than about 25 (20, 15, 10, 5, 2, or 1) mole percent of at least one comonomer.

[0375] Any of the embodiments listed herein, wherein the comonomer is chosen from cyclohexanedimethanol, 2,2,4,4-tetramethyl-1,3-cyclobutanediol (TMCD), neopentyl diol, propanediol, butanediol, diethylene glycol (DEG),isosorbide, hexanediol, methyl-2,4-pentanediol, poly(tetramethylene ether) glycol, polyethylene glycol, isomers thereof, or combinations thereof.

[0376] Any of the embodiments listed herein, wherein the comonomer is chosen from dimethyl isophthalate, cyclohexanedicarboxylic diester, or combinations thereof.

[0377] Any of the embodiments listed herein, further comprising prior to (a), treating a stream of mixed plastic waste to provide the waste plastic feed stream in step (a), wherein the treating comprises at least one processing step chosen from washing, drying, sorting, or size reducing at least a portion of the crude feed stream.

[0378] Any of the embodiments listed herein, wherein the depolymerizing comprises depolymerizing the PET in a first depolymerization zone with a first depolymerization solvent to provide a first dialkyl terephthalate and transesterifying at least a portion of the first dialkyl terephthalate with a solvent comprising methanol to form the r-DMT.

[0379] Any of the embodiments listed herein, wherein the depolymerizing performed in the first depolymerization zone is carried out at an average temperature in the range of at least about 100°C (110, 115, 120, 125, 130, 135, 140, 145, 150, 160, 165, 170, 175, 180, 185, or 190°C) and / or not more than about 275°C (250, 240, 230, 220, 215, 210, 205, 200, 195, 190, 185, 180, or 175°C) and a pressure of 0 to 500 psig, 0 to 250 psig, 0 to 100 psig, 0 to 50 psig, or 1 to 25 psig for a time period of 5 minutes to 24 hours, 30 minutes to 12 hours, 2 hours to 10 hours, or 3 hours to 8 hours.

[0380] Any of the embodiments listed herein, wherein the first depolymerization solvent comprises a C2 to C14 alcohol or a C2 to C14 diol.

[0381] Any of the embodiments listed herein, wherein the transesterifying is carried out at a temperature of at least about 25 (30, 35, 40)°C and / or not more than about 80 (75, 70, 65, 60, 55, or 50)°C and a pressure of 0 to 1 MPa, 0 to 0.5 MPa, or 0.1 to 0.25 MPa for a time period of 1 to 16 hours, 1.5 to 12 hours, or 4 to 10 hours.

[0382] Any of the embodiments listed herein, wherein the depolymerizing comprises depolymerizing at least a portion of the PET in a depolymerization zone in the presence of methanol to form the r-DMT.

[0383] Any of the embodiments listed herein, wherein the depolymerizing is carried out in the presence of a solvent chosen from water, C1 to C14 alcohols, C2 to C14 diols, ammonia, combinations thereof,

[0384] Any of the embodiments listed herein, wherein the solvent comprises ethylene glycol.

[0385] Any of the embodiments listed herein, wherein the solvent comprises methanol.

[0386] Any of the embodiments listed herein, wherein the solvent comprises C2 to C14 alcohols or diols.

[0387] Any of the embodiments listed herein, wherein the solvent comprises 2-ethylhexanol.

[0388] Any of the embodiments listed herein, wherein the depolymerizing is carried out at an average temperature in the range of at least about 100°C (110, 115, 120, 125, 130, 135, 140, 145, or 150°C) and / or not more than about 275°C (250, 225, 200, 195, 190, or 185°C).

[0389] Any of the embodiments listed herein, wherein the depolymerizing is carried out in the presence of at least one depolymerization catalyst.

[0390] Any of the embodiments listed herein, wherein the catalyst is chosen from Lewis diesters or bases; metal acetates, titanium alkoxides, tinbased catalysts (e.g., tin oxalate, monobutyltin oxide, monobutyltin tris(2-ethylhexanoate); potassium carbonate, potassium bicarbonate, potassium acetate, sodium acetate, titanium tetra(isopropoxide), or combinations thereof.

[0391] Any of the embodiments listed herein, wherein the depolymerization catalyst is present in an amount of from about 0.001 (0.005, 0.0075, or 0.010) and / or not more than about 0.10 (0.075, 0.05, or 0.025) equivalents of catalyst per PET unit.

[0392] Any of the embodiments listed herein, further comprising prior to the crystallizing of (b), separating at least a portion of the depolymerized intermediate stream in a separation zone to provide a light organics stream and a heavy organics stream comprising r-DMT and crystallizing at least a portion of the heavy organics stream in the crystallizing of (b).

[0393] Any of the embodiments listed herein, wherein the r-terephthalyl stream comprises r-DMT in an amount of at least about 10 (15, 20, 25, or 30)weight percent and / or not more than about 80 (75, 70, 65, 60, 55, 50, 45, 40, 35, or 30) weight percent, based on the total weight of the stream.

[0394] Any of the embodiments listed herein, wherein the r-terephthalyl stream comprises ethylene glycol in an amount of at least 1 (2, 5, 10, 15, or 20) weight percent and / or not more than about 50 (45, 40, 35, 30, or 25) weight percent, based on the total weight of the stream.

[0395] Any of the embodiments listed herein, wherein the r-terephthalyl stream comprises methanol in an amount of at least about 10 (15, 20, 25, or 30) weight percent and / or not more than about 75 (70, 65, 60, or 55) weight percent, based on the total weight of the stream.

[0396] Any of the embodiments listed herein, wherein the r-terephthalyl stream comprises one or more additional recycled content diols and / or diesters in an amount of at least about 0.1 (0.5, 1 , 2, 3, 5, or 10) weight percent and / or not more than about 40 (35, 30, 25, 20, or 15) weight percent, based on the total weight of the stream.

[0397] Any of the embodiments listed herein, wherein the additional recycled content diols and / or diesters are chosen from one or more of recycled content cyclohexanedimethanol (r-CHDM), recycled content dimethyl isophthalate (r-DMI), recycled content neopentyl diol (r-NPG), recycled content propanediol (r-PDO), recycled content butanediol (r-BDO), or recycled content diethylene glycol (r-DEG).

[0398] Any of the embodiments listed herein, wherein said crystallizing comprises heating the recycled content terephthalate stream to form an r-DMT solution and then cooling the r-DMT solution to precipitate the crystallized crude r-DMT.

[0399] Any of the embodiments listed herein, further comprising, prior to the melting of (c), washing the crude r-DMT solids stream with a solvent to provide a washed crude r-DMT solids stream and melting the washed crude r-DMT solids stream in (c).

[0400] Any of the embodiments listed herein, wherein the solvent comprises a C1 to C14 alcohol or diol.

[0401] Any of the embodiments listed herein, wherein the solvent comprises methanol.

[0402] Any of the embodiments listed herein, wherein the washing includes subjecting the crude r-DMT solids stream from about 1 to about 10 (1 to 8, 1 to 6, 1 to 5, 2 to 6, 2 to 4, or 1 to 3) wash steps.

[0403] Any of the embodiments listed herein, wherein the mass ratio of solvent to DMT for each wash step is at least about 1:1 (1.1:1, 1.25:1, or 1.5:1) and / or not more than about 10:1 (7: 1 , 5: 1 , or 3: 1 ).

[0404] Any of the embodiments listed herein, wherein the solvent has a temperature of at least about 25 (30, 35, or 40)°C and / or not more than about 65 (60, 55, 50, or 45)°C when contacting the crude r-DMT solids stream.

[0405] Any of the embodiments listed herein, wherein prior to the washing, the crude r-DMT solids stream comprises DMT in an amount of at least about 60 (65, 70, or 75) weight percent and / or not more than about 95 (93, 90, 85, 80, or 75) weight percent, based on the total weight of the crude r-DMT solids stream.

[0406] Any of the embodiments listed herein, wherein prior to the washing, the crude r-DMT solids stream comprises methanol in an amount of at least about 1 (2, 5, 7, or 10) weight percent and / or not more than about 30 (25, 20, or 15) weight percent, based on the total weight of the crude r-DMT solids stream.

[0407] Any of the embodiments listed herein, wherein prior to the washing, the crude r-DMT solids stream comprises ethylene glycol in an amount of at least about 0.1 (0.25, 0.5, 1, 2, or 5) weight percent and / or not more than about 30 (25, 20, or 15) weight percent, based on the total weight of the crude r-DMT solids stream.

[0408] Any of the embodiments listed herein, wherein prior to the washing, the crude r-DMT solids stream comprises one or more recycled content co-monomers in an amount of at least about 0.001 (0.01 , 0.05, 0.1 , 0.5, 1 , or 2) weight percent and / or not more than about 5 (3, 2, 1.5, 1 , or 0.5) weight percent, based on the total weight of the crude r-DMT solids stream.

[0409] Any of the embodiments listed herein, wherein after the washing, the crude r-DMT solids stream comprises DMT in an amount of at least about 75 (80, 85, 88, or 90) weight percent and / or not more than about 99 (97, 95, 92, or 90) weight percent, based on the total weight of the crude r-DMT solids stream.

[0410] Any of the embodiments listed herein, wherein after the washing, the crude r-DMT solids stream comprises methanol in an amount of at least about 1 (2, 5, 7, or 10) weight percent and / or not more than about 25 (20, 15, 10, or 5) weight percent, based on the total weight of the crude r-DMT solids stream.

[0411] Any of the embodiments listed herein, wherein after the washing, the crude r-DMT solids stream comprises ethylene glycol in an amount of at least about 0.001 (0.005 or 0.01) weight percent and / or not more than about 0.5 (0.25, 0.10, or 0.05) weight percent, based on the total weight of the crude r-DMT solids stream.

[0412] Any of the embodiments listed herein, wherein after the washing, the crude r-DMT solids stream comprises one or more recycled content comonomers in an amount of at least about 0.5 (1, 1.5, 2, or 5) parts per million by weight (ppm) and / or not more than about 500 (250, 100, 50, or 25) ppm, based on the total weight of the crude r-DMT solids stream.

[0413] Any of the embodiments listed herein, wherein the melting includes heating the crude r-DMT solids stream to an average temperature of at least about 140 (145, 150, 155, or 160)°C and / or not more than about 210 (205, 200, 195, 190, 185, 180, 175, or 170)°C.

[0414] Any of the embodiments listed herein, wherein the melting of (c) is carried out at a pressure of at least about 0 (0.10, or 0.25) psi and / or not more than about 5 (3, 2, 1) psi.

[0415] Any of the embodiments listed herein, wherein the melting is carried out in an agitated vessel.

[0416] Any of the embodiments listed herein, wherein during the melting of (c), recovering vapor generated during the melting, wherein the vapor comprises ethylene glycol, methanol, and other volatile compounds.

[0417] Any of the embodiments listed herein, wherein the molten crude r-DMT stream comprises DMT in an amount of at least about 75 (80, 82, 85, 87, or 90) weight percent and / or not more than about 95, 92, 90, 87, or 85) weight percent, based on the total weight of the mixture.

[0418] Any of the embodiments listed herein, wherein the molten crude r-DMT stream comprises methanol in an amount of 0 weight percent, or at leastabout 100 ppm (500, 750, or 1000 ppm) and / or not more than about 10 (7, 5, 3, 2, 1 , or 0.5) weight percent, based on the total weight of the mixture.

[0419] Any of the embodiments listed herein, wherein the molten crude r-DMT stream comprises ethylene glycol in an amount of at least about 0.01 (0.05, 0.10, 0.50, 1, 2, 3, or 5) weight percent and / or not more than about 10 (7.5, 5, 2.5, 2, 1.5, 1 , 0.5, 0.25, 0.1 weight percent or not more than about 750 ppm, 500 ppm, 300 ppm, 250 ppm), based on the total weight of the mixture.

[0420] Any of the embodiments listed herein, wherein the molten crude r-DMT stream comprises one or more of the following components in the following amounts, based on the total weight of the stream or composition: methyl formyl benzoate (MFB) in an amount of 0 ppm or less than about 1 (0.5 or 0.25) ppm; dimethyl phthalate (DMP) in an amount of 0 ppm or less than about 1 (0.5 or 0.25) ppm; bis(2-hydroxyethyl)terephthalate (BHET) in an amount of at least about 1 (10, 50, 100, 200, 250, 500, 750, 1000, 2500, or 5000) ppm and / or not more than about 10, 7, 5, 2.5, or 1 weight percent, or not more than about 5000 ppm, 1000 ppm, 750 ppm, 500, 250, 100 ppm; mono(2-hydroxyethyl)terephthalate (MHET) in an amount of at least about 1 (10, 50, 100, 200, 250, 500, 750, 1000, 2500, or 5000) ppm and / or not more than about 10, 7, 5, 2.5, or 1 weight percent, or not more than about 5000 ppm, 1000 ppm, 750 ppm, 500, 250, 100 ppm; and / or methyl hydrogen terephthalate(MHT) in an amount of at least about 1000 (1500, 2000, 2500, 3000, 3500, or 5000) ppm and / or not more than about 0.10 weight percent or not more than about 7500 (5000, 3500, 3000, or 2500 ppm).

[0421] Any of the embodiments listed herein, wherein the molten crude r-DMT stream comprises elemental antimony in an amount of at least about 1 (2.5, 5, 10, 25, 50, 75, 100, 125, or 150) ppm and / or not more than about 5000 (3500, 2500, 1000, 750, 500, 350, 300, 200, 100, or 50) ppm.

[0422] Any of the embodiments listed herein, wherein the molten crude r-DMT stream is a liquid when fed to the distillation zone (reactive distillation zone or purification zone).

[0423] Any of the embodiments listed herein, wherein the molten crude r-DMT stream has a total solids content of not more than about 1 (0.5, 0.25, or 0.1) weight percent, based on the total weight of the stream.

[0424] Any of the embodiments listed herein, prior to the distilling, combining a catalyst-containing stream with the molten crude r-DMT stream to provide a catalyst-containing molten r-DMT stream.

[0425] Any of the embodiments listed herein, wherein the combining is carried out prior to introducing the molten crude r-DMT stream into the distillation zone (or reactive distillation zone or purification zone).

[0426] Any of the embodiments listed herein, wherein the combining is carried out in the distillation zone (reactive distillation zone or purification zone) by simultaneously introducing the catalyst-containing stream and the molten crude r-DMT stream into a distillation column.

[0427] Any of the embodiments listed herein, wherein the catalystcontaining stream comprises at least one catalyst and at least one solvent.

[0428] Any of the embodiments listed herein, wherein the solvent is chosen from a C1 to C14 alcohol or a C2 to C14 diol.

[0429] Any of the embodiments listed herein, wherein the solvent comprises methanol.

[0430] Any of the embodiments listed herein, wherein the catalyst is present in the catalyst-containing stream in an amount of at least about 0.01 (0.02, 0.025, or 0.03) weight percent and / or not more than about 1 (0.75, 0.50, 0.25, 0.1, or 0.05) weight percent, based on the total weight of the catalystcontaining stream.

[0431] Any of the embodiments listed herein, wherein the catalystcontaining molten r-DMT stream comprises the catalyst in an amount of at least about 5 (10, 20, 25, 30, 35, 50, 75, 100, or 250) ppm and / or not more than about 1000 (750, 500, 300, 200, 100, 75, or 50) ppm, based on the total weight of the stream.

[0432] Any of the embodiments listed herein, wherein the distilling is carried out in at least one distillation column.

[0433] Any of the embodiments listed herein, wherein the average overhead temperature of the distillation column during the distilling is at least about 150 (155, 160, 165, 170, 175, or 180)°C and / or not more than about 225 (220, 215, 210, 205, 200, 195, or 190)°C.

[0434] Any of the embodiments listed herein, wherein the average bottom temperature of the distillation column during the distilling is at leastabout 190 (195, 200, 205, 210, 215, or 220)°C and / or not more than about 260 (255, 250, 245, 240, 235, or230)°C.

[0435] Any of the embodiments listed herein, wherein the average overhead temperature of the distillation column during the distilling is less than 760 (400, 350, 300, or 250) mm Hg or is at least about 5 (10, 15, 20, 25, 30, or 35) mm Hg and / or not more than about 200 (150, 125, 100, or 75) mm Hg.

[0436] Any of the embodiments listed herein, wherein the distillation column is operated at a reflux ratio of at least about 0.1 (0.2, 0.25, or 0.3) and / or not more than about 3 (2.5, 2, 1.5, or 1 ) during the distilling.

[0437] Any of the embodiments listed herein, wherein the distillation column is a reactive distillation column.

[0438] Any of the embodiments listed herein, wherein the distillation column is a conventional distillation column.

[0439] Any of the embodiments listed herein, wherein the conventional distillation column comprises at least 2 (3, 5, 8, or 10) theoretical distillation stages and / or not more than about 35 (20, 25, 20, or 15) theoretical distillation stages, calculated according to the McCabe-Thiele method.

[0440] Any of the embodiments listed herein, wherein the distillation column comprises not more than (or less than) 5 (4, or 3) theoretical stages, or from 1 to 5 (1 to 4, or 1 to 3) theoretical stages, calculated according to the McCabe-Thiele method.

[0441] Any of the embodiments listed herein, wherein the distillation column comprises at least about 1 (2, or 3) and / or not more than about 8 (6, 5, or 4) actual distillation stages.

[0442] Any of the embodiments listed herein, further comprising, recovering an overhead vapor stream comprising purified r-DMT from the distillation zone (reactive distillation zone) and condensing at least a portion of the overhead vapor stream to provide the purified r-DMT product stream.

[0443] Any of the embodiments listed herein, wherein the purifying comprises conventional (non-reactive) distillation.

[0444] Any of the embodiments listed herein, wherein the purifying comprises subjecting the molten crude r-DMT stream to multiple washes with at least one solvent to provide the purified r-DMT product.

[0445] Any of the embodiments listed herein, wherein the solvent comprises a C1 to C14 alcohol or a C2 to C14 diol.

[0446] Any of the embodiments listed herein, wherein the solvent comprises methanol.

[0447] Any of the embodiments listed herein, wherein a first wash is conducted with a first solvent and a second wash is conducted with a second solvent different from the first solvent.

[0448] Any of the embodiments listed herein, wherein the solvent has a temperature of at least about 10 (15, 20, 25, or 30)°C and / or not more than about 60 (55, 50, 45, 40, or 35)°C during the washes.

[0449] Any of the embodiments listed herein, wherein the multiple washes include at least 2 (3, 4, or 5) and / or not more than about 20 (15, 12, 10, or 8) individual wash steps.

[0450] Any of the embodiments listed herein, wherein the purifying comprises dissolving at least a portion of the molten crude r-DMT stream in a solvent to form a crude r-DMT solution and then crystallizing the crude r-DMT solution to provide the purified r-DMT product as precipitated DMT solids.

[0451] Any of the embodiments listed herein, wherein the crystallizing is carried out for a time period of at least about 2 (4, 6, 8, 10, 12, 15, 18, or 20) hours and / or not more than about 48 (40, 35, 30, or 24) hours and under similar temperature and pressure conditions as noted previously.

[0452] Any of the embodiments listed herein, wherein the concentration, by weight, of free ethylene glycol in the purified r-DMT product stream is less than 50 percent of the concentration, by weight, of free ethylene glycol in the molten crude r-DMT stream.

[0453] Any of the embodiments listed herein, wherein the total weight of free ethylene glycol removed from the (reactive) distillation column (all steams) is at least about 45 (50, 55, 60, 65, 70, or 75) percent and / or not more than about 99 (95, 90, 85, or 80) percent of the total weight of free ethylene glycol introduced into the (reactive) distillation column (all streams).

[0454] Any of the embodiments listed herein, wherein the following recovery percentages of each component introduced into the distillation (or reactive distillation or purification) zone exits that zone in the purified r-DMT product stream: at least about 50 (75, 80, 85, 87, or 90) perc...

Claims

CLAIMSWe claim - 1. A recycled content article of manufacture (r-article) formed from a recycled content polyethylene terephthalate (r-PET) composition, wherein the r-article has a recycled content of greater than 50 percent and has a haze value, measured according to ASTM D-1003 using a 1 / 8-in thick plaque, of at least 2% and not more than 20%.

2. The r-article of claim 1 , wherein the r-article has a recycled content of at least 75 percent, and wherein the r-PET composition comprises chemically recycled PET (cr-PET) and mechanically recycled PET (mr-PET).

3. The r-article of claim 2, wherein the r-PET composition further comprises virgin PET.

4. The r-article of claim 1, wherein the r-PET composition comprises from about 0.2 to about 3 percent of methyl end groups, as determined by NMR, and wherein the r-PET composition comprises less than 5 weight percent of residues of monomers other than dimethyl terephthalate, terephthalic acid, and ethylene glycol.

5. The r-article of claim 1 , wherein the article is thermoformed.

6. The r-article of claim 1, wherein the r-article is injection blow molded, injection stretch blow molded, or extrusion blow molded.

7. The r-article of claim 1, wherein the r-article is extruded or calendered.

8. The r-article of claim 1 , wherein the r-article is chosen from a fiber, a filament, a yam, or a textile.

9. The r-article of claim 1, wherein the r-articles is chosen from a bottle, a container, or a preform.

10. The r-article of claim 1, wherein the r-article is chosen from a film or a sheet.

11. A recycled content plastic article (r-article) formed from a recycled content polyethylene terephthalate (r-PET) composition, said r-article having a recycled content of greater than 50 percent, wherein the article comprises:(a) at least one characteristic (i) or (ii) - (i) from about 0.2 to about 3 percent of methyl end groups based on the total number of end groups, as determined by NMR;(ii) from about 0.1 to about 10 mole percent of residues of cyclohexanedimethanol (CHDM), based on the total moles of diol residues in the r-PET composition; and(b) at least one characteristic (iii) to (v) - (iii) at least 5 parts per million by weight (ppm) of total chloride (Cl);(iv) at least 5 ppm of total nitrogen (N); and(v) a haze value of at least 3%, measured by ASTM D-1003 with a 1 / 8-inch plaque.

12. The r-article of claim 11, wherein the r-PET composition used to form the r-article has a combined amount of chemically recycled PET (cr-PET) and mechanically recycled PET (mr-PET) of at least 75 weight percent, based on the total weight of the r-PET composition.

13. The r-article of claim 11 , wherein the r-PET composition comprises one or more of total nitrogen (N), total chloride (Cl), and total silicon (Si), and wherein the combined amount of N, Cl, and Si is in the range of from about 5 to about 60 parts per million by weight (ppm), based on the total weight of the r-PET composition.

14. A recycled content plastic article (r-article) formed from a recycled content polyethylene terephthalate (r-PET) composition, said r-article having arecycled content of at least 10 percent and wherein the r-article composition comprises one or both of (a) and (b) - (a) an amount of total chloride (Cl) at least 5 parts per million by weight (ppm) and less than 15 ppm; and / or(b) an amount of total nitrogen (N) at least 5 ppm and less than 15 ppm, wherein each amount (a) and (b) is based on the total weight of the r-article, andwherein the r-article is not formed from 100 weight percent of mechanically recycled PET (mr-PET).

15. The r-article of claim 14, wherein the r-article is chosen from bottles, medical containers, personal care containers, or cosmetic containers.

16. A recycled content plastic article (r-article) formed from a recycled content polyethylene terephthalate (r-PET) composition comprising:5 to 75 weight percent chemically recycled PET (cr-PET);5 to 75 weight percent mechanically recycled PET (mr-PET); and optionally, 5 to 45 weight percent of virgin PET,wherein the combined amount of cr-PET, mr-PET, and virgin PET, when present, are at least 95 weight percent of the r-PET composition.

17. The r-article of claim 16, wherein the r-PET composition comprises from 45 to 90 weight percent of cr-PET and from 5 to 55 weight percent of mr-PET.

18. The r-article of claim 16, wherein the r-PET composition further comprises from 5 to 25 weight percent virgin PET.

19. The r-article of claim 16, wherein the combined amount of cr-PET and mr-PET in the r-PET composition is at least 75 percent, based on the total weight of the r-PET composition.

20. The r-article of claim 16, wherein the r-article has a haze of from 3 to 20 percent, measured according to ASTM D-1003 using a 1 / 8-inch plaque,and wherein the r-PET composition comprises less than 5 weight percent of residues other than residues of dimethyl terephthalate, terephthalic acid, and ethylene glycol.

21. A recycled content plastic article (r-article) formed from a recycled content polyethylene terephthalate (r-PET) composition comprising at least 5 weight percent of chemically recycled PET (cr-PET), at least 5 weight percent of mechanically recycled PET (mr-PET), and optionally at least 5 weight percent of virgin PET,wherein the r-PET composition has a total recycled content of greater than 50%,wherein the combined amount of cr-PET, mr-PET, and virgin PET, when present, are at least 95 weight percent of the composition, and wherein the r-article has one or both of the following properties (i) and / or (ii):(i) an L* value of at least 80, measured according to 1976 CIE L*a*b* Color Space; and / or(ii) a haze value of less than 20 percent, measured according to ASTM D-1003 Method A using a 1 / 8-inch plaque.

22. A recycled content plastic article (r-article) formed from a recycled content polyethylene terephthalate (r-PET) composition comprising at least 5 weight percent of chemically recycled PET (cr-PET), at least 5 weight percent of mechanically recycled PET (mr-PET), and at least 5 weight percent of virgin PET, wherein the combined amount of cr-PET, mr-PET, and virgin PET are at least 95 weight percent of the composition,wherein the r-PET composition has a total recycled content of greater than 50%,and wherein the r-article has one or both of the following properties (i) and / or (ii):(i) an L* value, measured according to 1976 CIE L*a*b* Color Space, within about 15 of the L* value of the virgin PET; and / or(ii) a haze value, measured according to ASTM D-1003 with a 1 / 8-inch plaque, within about 20 percent of the haze value of the virgin PET.

Images