Liquid Reclamation and Solid Foam Recycling / Regeneration: Compositions and Methods

Abstract

Methods and systems are provided for reclaiming spent liquid and solid materials formed using or including, but not limited to, haloolefin liquid refrigerants, solvents, immersion fluids, and foams. Reclaimed compositions and components that meet AHRI 700 2019 industry standards for quality are also provided.

Description

[Technical Field]

[0001] (CROSS-REFERENCE TO RELATED APPLICATIONS) This application claims priority to U.S. Patent Application No. 63 / 402,727, filed August 31, 2022, the disclosure of which is incorporated herein by reference in its entirety.

[0002] FIELD OF THE INVENTION The present invention relates to halogenated liquid and foam waste regeneration, whereby spent halogenated liquids such as refrigerants, solvents, immersion fluids, and foam waste are regenerated by physical and / or chemical treatment and converted into high purity components, compositions, and products, and optionally compositionally rebalanced to meet AHRI 700 2019 quality requirements for reuse and recycling. [Background technology]

[0003] The popularity of the circular economy concept and its adoption to reduce waste has garnered significant attention. Halogenated olefins, such as hydrochloroolefins (HCO), chlorofluoroolefins (CFO), hydrofluoroolefins (HFO), and hydrochlorofluoroolefins (HCFO), have been developed to replace the chlorofluorocarbons (CFC), hydrochlorofluorocarbons (HCFC), and hydrofluorocarbons (HFC), thereby providing heat transfer media with lower global warming potential (GWP) and ozone depleting potential (ODP) properties that need to be regenerated. Halogenated olefins HCO, HFO, and HCFO, as well as fluorinated ethers such as hydrofluoroethers (HFE), fluoropolyethers (PFPE, HFPE), hydrofluoroolefinic ethers (HFOE), and hydrofluorocarbons (HFC), collectively halogenated liquids, also find use as solvents, blowing agents, foam generators, cleaning, and dielectric fluids for electronic devices that need to be reclaimed after use to reduce waste. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] U.S. Patent Application No. 63 / 402,727 Summary of the Invention [Problem to be solved by the invention]

[0005] Therefore, there continues to be a need to apply circular economy concepts to all halogenated liquids and provide an integrated / comprehensive system and process for regeneration that reduces liquid halogenated waste and foam waste and produces high purity and high quality regenerated liquids and compositions that meet at least AHRI 700 2019 standards for recycling and use. [Means for solving the problem]

[0006] The present invention is directed to an integrated regeneration process for treating and converting used (e.g., used, contaminated) halogenated liquids and foam waste into high-purity liquids, compositions, and solids that meet industry standards for reuse and recycling. These halogenated liquids and foam waste are recovered (collected) from various sources, such as heat transfer liquid circulating systems, storage facilities, unwanted refrigerant sources, foam production facilities, and foam recycling centers. The physical and chemical properties of the used liquids are evaluated, and treatments are selected to remove contaminants, moisture, water, acidity, gases (e.g., air), oils, particles / solids, stabilizers, etc., to provide high-purity halogenated liquid components and mixtures / blends. For unsolubilized water levels above the saturation point in the halogenated liquid, distillation or decanting can also be used. Water removal can involve the use of molecular sieves or decanting, or a combination of the two. Distillation can be used to separate and / or purify the liquid mixture and liquid components of the spent halogenated liquid, for example, R-514A can be separated into dichloroethylene (R-1130) and 1,1,1,4,4,4-hexafluorobut-2-ene (Z-1336mzz).

[0007] Disclosed herein is an integrated process for the regeneration and production of high purity refrigerants, refrigerant blends, solvents, soak fluids, and polymers, including but not limited to the liquids identified in Table 1.

[0008] [Table 1-1]

[0009] [Table 1-2]

[0010] Disclosed herein is an integrated process for the regeneration and production of high purity refrigerants, refrigerant blends, solvents, soak fluids, and polymers, including but not limited to the liquids identified in Tables 2, 3, and 4.

[0011] [Table 2]

[0012] [Table 3-1]

[0013] [Table 3-2]

[0014] [Table 3-3]

[0015] [Table 4]

[0016] Also disclosed herein are methods for compositions, including but not limited to blends of at least one of HFO-E-1336mzz, HFO-Z-1336mzz, HFO-Z / E 1336mzz, HCFO-E-1224yd, HCFO-E-1233zd, HCFO-Z-1233zd, and HCFO-Z-1224yd, and compositionally re-balanced and optionally stabilized compositions from treatment using the disclosed regeneration process. The stabilizer package includes at least one of an antioxidant, an acid acceptor, and a metal stabilizer, wherein the antioxidant is selected from butylated hydroxytoluene, butylated hydroxyanisole, tert-butylhydroquinone, 4-methoxyphenol, and propyl 3,4,5-trihydroxybenzoate; the acid acceptor is selected from epoxybutane, an amine, and acetaldehyde di-methylhydrazone (ADH); and the metal stabilizer is selected from N,N'-bis(salicylidene)-1,2-propanediamine, benzotriazole, and derivatives thereof.

[0017] Disclosed herein is an integrated system and method for refrigerant regeneration, including but not limited to, HFO-E-1336mzz, HFO-Z-1336mzz, HFO-Z / E 1336mzz, HCFO-Z-1224yd, HCFO-E-1233zd, R-514A; HFO-E-1336mzz, HFO-Z-1336mzz, HCFO-1233zd, and HCFO-1224yd components and blends.

[0018] Disclosed herein is an integrated system and method for regenerating liquid blend blowing agents, including, but not limited to, at least one of E-1336mzz, Z-1336mzz, E-1233zd, and Z-1224yd.

[0019] Disclosed herein is an integrated system and method for solvent and immersion coolant regeneration, including, but not limited to, Vertrel™ specialty fluids such as Vertrel XF; Opteon™ specialty fluids such as SF10, SF30, SF33, CFX-70, SF79, SF80, SF01, SF05; Novec 7100, Novec 7200, Novec 7300, Novec 7500, Novec 649, Novec 71DE, Novec 71DA, Novec 72DA, Novec 72DE, Novec 71IPA, Novec 73DE; and 3M Hydrofluoroethers such as Microcare MCF.

[0020] Disclosed herein is an integrated system and method for converting foam waste into reusable polymers and distillable halogenated vapors for purification.

[0021] In one embodiment disclosed herein, spent halogenated liquids, including but not limited to liquid refrigerants, refrigerant blends, liquid blowing agents, solvents, and / or immersion coolants, are collected, evaluated, treated to remove at least one of acidity, oils, particulates / solids, stabilizers and spent stabilizers, and moisture, separated, and optionally compositionally re-equilibrated to produce high purity, industrially compatible halogenated liquid components and blends for reuse as refrigerants, liquid blowing agents, solvents, and / or immersion coolants (fluids).

[0022] In still further embodiments disclosed herein, one or more unrecycled (spent) chlorofluoroolefins (CFOs), hydrochloroolefins (HCOs), hydrofluoroolefins (HFOs), hydrochlorofluoroolefins (HCFOs), hydrofluoroethers (HFEs), hydrofluoroolefin ethers (HFOEs), hydrofluoroketones (HFKs), fluoroketones (FKs) liquids are recovered to produce high purity components and blends.

[0023] In further embodiments disclosed herein, hydrofluoroolefin (HFO) liquids and / or hydrochlorofluoroolefin (HCFO) liquids are regenerated.

[0024] In still further embodiments disclosed herein, hydrofluoroether (HFE) liquid is regenerated.

[0025] In further embodiments disclosed herein, one or more unregenerated (spent) hydrofluoroolefin (HFO) liquids and / or mixtures of hydrochlorofluoroolefin (HCFO) liquids and hydrofluoroether (HFE) liquids are regenerated to produce high purity HFO, HCFO, and HFE components and blends.

[0026] In still further embodiments disclosed herein, mixtures of one or more unregenerated (spent) chlorofluoroolefin (CFO) liquids, hydrochloroolefin liquids (HCO), hydrofluoroolefin (HFO) liquids, hydrochlorofluoroolefin (HCFO) liquids, hydrofluoroether (HFE) liquids, fluoroketone (FK), and hydrofluoroketone (HFK) liquids are regenerated to produce high purity CFO, CHO, HFO, HCFO, HFE, and HFK components and blends.

[0027] In another embodiment disclosed herein, the refrigerant liquid is regenerated.

[0028] In another embodiment disclosed herein, the solvent is regenerated.

[0029] In another embodiment disclosed herein, the submerged coolant is regenerated.

[0030] In other embodiments herein, one or more of the compounds identified in Table 1 are regenerated.

[0031] In other embodiments herein, one or more of the compounds identified in Table 2 are regenerated.

[0032] In other embodiments herein, one or more of the compounds identified in Table 3 are regenerated.

[0033] In other embodiments herein, one or more of the compounds identified in Table 4 are regenerated.

[0034] In another embodiment disclosed herein, any of the regenerated compositions disclosed herein is packaged in a container constructed of any suitable material and design capable of sealing the composition. Examples of suitable containers include pressure vessels such as tanks, filled cylinders, and secondary filled cylinders. The containers can be constructed from any suitable material, such as carbon steel, manganese steel, chromium-molybdenum steel, particularly low-alloy steel, stainless steel, and in some cases, aluminum alloys. The refrigerant-containing compositions stored in these containers can be transferred to heat transfer systems and used as working fluids.

[0035] In another embodiment of the present invention, post-consumer foam waste is collected and crushed to form processable solids and release trapped vapors, which are pelletized and the vapors are collected, separated, and refined into reusable components and compositions.

[0036] In one embodiment of the present invention, one or more molecular sieve beds are used to remove water, e.g., water above or below its saturation point (greater than 350 ppm), from halogenated liquids, such as refrigerants, solvents, blowing agents, and immersion fluids.

[0037] In another embodiment of the invention, unsolubilized water above its saturation point is removed from the refrigerant, solvent, blowing agent, trapped vapor, and immersion fluid using distillation or decanting.

[0038] In yet a further embodiment of the present invention, refrigerant blends, solvent blends, immersion fluids, and / or commercial blends are purified and separated into their constituent components, such as, for example, separating R-514A into dichloroethylene (DCE) and Z-1336mzz.

[0039] Disclosed herein are systems, methods, and additives for stabilizing refrigerants, refrigerant blends, liquid blowing agents, solvents, and electronic immersion fluids, where the stabilizer and / or stabilizer package includes, but is not limited to, an antioxidant selected from butylated hydroxytoluene (BHT), butylated hydroxyanisole (BHA), tert-butylhydroquinone, 4-methoxyphenol, propyl 3,4,5-trihydroxybenzoate, an acid acceptor (epoxybutane, amine, and acetaldehyde di-methylhydrazone (ADH)), and optionally a metal stabilizer (N,N'-bis(salicylidene)-1,2-propanediamine, benzotriazole, and derivatives thereof). [Brief explanation of the drawings]

[0040] [Figure 1] 1 illustrates a method and system for regenerating unregenerated halogenated liquid, according to an embodiment of the present invention. [Figure 2] 1 illustrates a method and system for foam waste recycling according to an embodiment of the present invention. [Figure 3] 1 illustrates a method and system for foam waste recycling according to another embodiment of the present invention. [Figure 4] 1 illustrates one embodiment of the present invention. [Figure 5] 1 shows a system for purifying unregenerated (unpurified) refrigerant liquid. [Figure 6] 1 shows a service center system. DETAILED DESCRIPTION OF THE INVENTION

[0041] The present invention is directed to an integrated regeneration process for treating and converting spent, e.g., contaminated, halogenated liquid and foam waste into high-purity liquids, compositions, and solids that meet industry standards for reuse and recycling. The properties of the spent halogenated liquid can be evaluated, and physical / chemical treatments can be selected to purify the spent halogenated liquid, for example, to remove contaminants, moisture, water, acidity, gases (e.g., air), oil, particles / solids, stabilizers, etc. For insoluble water levels above the saturation point, distillation or decanting can also be used. Water removal can involve the use of molecular sieves, decanting, etc. Distillation can be used to separate and / or purify the liquid and liquid components of the spent halogenated liquid, for example, to separate R-514A into dichloroethylene (R-1130) and 1,1,1,4,4,4-hexafluorobut-2-ene (Z-1336mzz).

[0042] In some embodiments, the regenerated halogenated liquids can be reused in a wide variety of applications as replacements for compositions containing CFCs and less desirable HCFCs. For example, the regenerated halogenated liquids of the present invention are useful as blowing agents, refrigerants, heating agents, power cycle agents, immersion coolants, and cleaning agents. In some embodiments, the regenerated halogenated liquids disclosed herein are packaged in containers constructed of any suitable material and design capable of sealing the liquid and / or liquid compositions. Examples of suitable containers include pressure vessels such as tanks, filled cylinders, and secondary filled cylinders. The containers can be constructed from any suitable material, such as carbon steel, manganese steel, chromium-molybdenum steel, particularly low-alloy steel, stainless steel, and in some cases, aluminum alloys. Refrigerant-containing compositions stored in these containers can be transferred to heat transfer systems and used as working fluids.

[0043] In some embodiments disclosed herein, the regenerated liquid refrigerant, liquid blowing agent, solvent, and / or immersion coolant (dielectrically compatible heat transfer medium for electronic devices) is selected from at least one hydrofluoroolefin (HFO), hydrochlorofluoroolefin (HCFO), hydrofluoroether (HFE), fluoropolyether (PFPE, HFPE) or hydrofluoroolefin ether (HFOE), and hydrofluorocarbon (HFC).

[0044] In some embodiments disclosed herein, the liquid refrigerant and / or liquid heat transfer medium does not undergo a phase change and can be used in coolant circuits to remove / transfer heat from power systems, vehicles, vehicle exhaust systems, and internal combustion engines (ICEs).

[0045] Hydrofluoroethers (HFEs) are compounds that contain carbon, hydrogen, and fluorine and also contain an ether bond. Hydrofluoroolefins (HFOs) are compounds that contain carbon, hydrogen, and fluorine and also contain a double bond. Hydrofluoroolefins (HCFOs) are compounds that contain carbon, hydrogen, fluorine, and also contain a double bond.

[0046] As used herein, ODP is defined in the World Meteorological association report "Scientific Assessment of Ozone Depletion, 2002," which is incorporated herein by reference. As used herein, GWP is defined for the global warming of carbon dioxide over a 100-year period and is defined in the same document as ODP.

[0047] As used herein, a refrigerant is a compound or mixture of compounds used as a working fluid to transfer heat from a heat source to a heat sink. Such heat transfer compositions may also be useful as refrigerants in cycles where the fluid undergoes a phase change, i.e., where the fluid changes from a liquid to a gas and back to a liquid again, or vice versa. Examples of heat transfer systems include, but are not limited to, air conditioners, freezers, refrigerators, heat pumps, water chillers, flooded evaporative chillers, direct expansion chillers, walk-in coolers, high temperature heat pumps, mobile refrigerators, mobile air conditioning units, power storage cooling systems, battery cooling, immersion cooling systems, data center cooling systems, and combinations thereof.

[0048] As used herein, immersion cooling is used to cool electronic devices such as data center servers, insulated-gate bipolar transistor (IGBT) devices, telecommunications infrastructure, military electronics, televisions (TVs), cell phones, monitors, drones, automotive batteries, electric vehicle (EV) powertrains, avionics devices, power supply devices, and displays. An immersion cooling system is a heat transfer device that lacks a compressor and in which the heat transfer medium has suitable dielectric properties. Generally, the item to be cooled is at least partially immersed (in direct contact) with a heat transfer fluid contained within a bath. In some embodiments, the heat transfer fluid may evaporate and condense within the bath. In other embodiments, there may not be a phase change involved.

[0049] Provided herein is an integrated method for recycling foam waste, including, but not limited to, closed-cell polyurethane foam. As known to those skilled in the art, foam compositions are generally formed from compositions containing one or more components capable of forming a foam and a blowing agent. In some embodiments, the blowing agent compound is at least one of E-1336mzz, Z-1336mzz, E-1233zd, and Z-1224yd.

[0050] As used herein, a refrigerant is a compound or mixture (blend) of compounds that acts as a heat transfer fluid in a cycle in which the fluid changes phase from a liquid to a gas and back again.

[0051] As used herein, the terms "comprises," "comprising," "includes," "including," "has," "having," or any other variation thereof, are intended to cover non-exclusive inclusions. For example, a composition, process, method, article, or device that comprises listed elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent in such composition, process, method, article, device, etc. Furthermore, unless expressly stated to the contrary, "or" refers to an inclusive "or," not an exclusive "or." For example, a condition A or B is satisfied by any one of the following: A is true (or present) and B is false (or absent), A is false (or absent) and B is true (or present), and both A and B are true (or present).

[0052] The transitional phrase "consisting of" excludes any unspecified element, step, or ingredient. In a claim, such a phrase closes the claim to including materials other than those recited, except for impurities normally accompanying the materials. When the phrase "consists of" appears within a clause in the body of a claim rather than immediately following the introductory section, the phrase is limited to only the elements recited in that clause and does not exclude other elements from the claim as a whole.

[0053] The transitional phrase "consisting essentially of" is used to define compositions, methods, and compositions that include materials, steps, mechanisms, components, or elements in addition to those literally disclosed, provided that these additionally included materials, steps, mechanisms, ingredients, or elements do not materially affect the basic and novel characteristics of the claimed invention, particularly the mechanism of action for achieving any desired result of the inventive process. The term "consisting essentially of" occupies intermediate ground between "comprising" and "consisting of."

[0054] It should be readily understood that where applicants have defined an invention or part thereof with open-ended terms such as "comprising," the description should (unless expressly stated otherwise) be construed to also include inventions that use the terms "consisting essentially of" or "consisting of."

[0055] Additionally, the use of "a" or "an" is used to describe elements and components described herein. This is done merely for convenience and to give a general sense of the scope of the invention. This description should be interpreted to include one or at least one, and the singular also includes the plural unless it is clear that a different meaning is intended.

[0056] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Although methods and materials similar or equivalent to those described herein can be used in the practice or testing of embodiments of the present invention, suitable methods and materials are described below. All publications, patent applications, patents, and other references mentioned herein are incorporated by reference in their entirety, unless a specific passage is cited. In case of conflict, the present specification, including definitions, will control. Furthermore, the materials, methods, and examples are illustrative only and not intended to be limiting.

[0057] 1, 100 shows a non-limiting example of a process and system for regenerating halogenated liquids and / or vapors according to the present invention. Unregenerated liquid is recovered using system 110.

[0058] In one embodiment, the unregenerated (used) liquid comprises at least one of hydrofluoroolefins (HFOs), hydrochlorofluoroolefins (HCFOs), hydrofluoroethers (HFEs), and mixtures and blends, particularly E-1336mzz, Z-1336mzz, E-1233zd, and Z-1224yd, and R-514A.

[0059] In another embodiment, the unregenerated (spent) liquid is a fluorobutane and perfluorobutane, pentane, hexane, heptane, and octane, including but not limited to 1,1,1,2,2,3,3,4,4,5,5,6,6-tridecafluorooctane, 1,1,1,2,2,3,4,5,5,5-decafluoropentane, 1,1,1,3,3-pentafluorobutane, 1,1,2,2,3,3,4-heptafluorocyclopentane, and tridecafluorooctane.

[0060] In still further embodiments, the unregenerated (spent) liquid may comprise fluorinated and perfluorinated C4-C7 unsaturated compounds, such as 1,1,1,2,3,4,4,4-octafluoro-2-butene (CFCF=CFCF), 1,1,2,3,3,4,4,4-octafluoro-1-butene (CFCFCF=CF), 1,1,1,2,4,4,4-heptafluoro-2-butene (CFCF=CHCF), 1,2,3,3,4,4,4-heptafluoro-1-butene (CHF=CFCFCF), 1,1,1,2,3,4,4-heptafluoro- Fluoro-2-butene (CHF2CF=CFCF3), 1,3,3,3-tetrafluoro-2-(trifluoromethyl)-1-propene ((CF3)2C=CHF), 1,1,3,3,4,4,4-heptafluoro-1-butene (CF2=CHCF2CF3), 1,1,2,3,4,4,4-heptafluoro-1-butene (CF2=CFCHFCF3), 1,1,2,3,3,4,4-heptafluoro-1-butene (CF2=CFCF2CHF2), 2,3,3,4,4,4-hexafluoro-1-butene (CF3CF2CF=CH2), 1,3,3 ,4,4,4-Hexafluoro-1-butene (CHF=CHCF2CF3), 1,2,3,4,4,4-Hexafluoro-1-butene (CHF=CFCHFCF3), 1,2,3,3,4,4-Hexafluoro-1-butene (CHF=CFCF2CHF2), 1,1,2,3,4,4-Hexafluoro-2-butene (CHF2CF=CFCHF2), 1,1,1,2,3,4-Hexafluoro-2-butene (CH2FCF=CFCF3), 1,1,1,2,4,4-Hexafluoro-2-butene (CHF2CH=CFCF3), 1,1,1,3, 4,4-Hexafluoro-2-butene (CF3CH=CFCHF2), 1,1,2,3,3,4-Hexafluoro-1-butene (CF2=CFCF2CH2F), 1,1,2,3,4,4-Hexafluoro-1-butene (CF2=CFCHFCHF2), 3,3,3-Trifluoro-2-(trifluoromethyl)-1-propene (CH2=C(CF3)2), 1,1,1,2,4-Pentafluoro-2-butene (CH2FCH=CFCF3), 1,1,1,3,4-Pentafluoro-2-butene (CF3CH=CFCH2F), 3,3,4,4,4-Pentafluoro-1-butene (CF3CF2CH=CH2), 1,1,1,4,4-pentafluoro-2-butene (CHF2CH=CHCF3), 1,1,1,2,3-pentafluoro-2-butene (CH3CF=CFCF3), 2,3,3,4,4-pentafluoro-1-butene (CH2=CFCF2CHF2), 1,1,2,4,4-pentafluoro-2-butene (CHF2CF=CHCHF 2), 1,1,2,3,3-pentafluoro-1-butene (CH3CF2CF=CF2), 1,1,2,3,4-pentafluoro-2-butene (CH2FCF=CFCHF2), 1,1,3,3,3-pentafluoro-2-methyl-1-propene (CF2=C(CF3)(CH3)), 2-(difluoromethyl)-3,3,3-trifluoro-1-propene (CH2=C(CHF2)(CF3)), 2 ,3,4,4,4-Pentafluoro-1-butene (CH2=CFCHFCF3), 1,2,4,4,4-Pentafluoro-1-butene (CHF=CFCH2CF3), 1,3,4,4,4-Pentafluoro-1-butene (CHF=CHCHFCF3), 1,3,3,4,4-Pentafluoro-1-butene (CHF=CHCF2CHF2), 1,2,3,4,4-Pentafluoro-1-butene (CHF= CFCHFCHF2), 3,3,4,4-tetrafluoro-1-butene (CH2=CHCF2CHF2), 1,1-difluoro-2-(difluoromethyl)-1-propene (CF2=C(CHF2)(CH3)), 1,3,3,3-tetrafluoro-2-methyl-1-propene (CHF=C(CF3(CH3)), 3,3-difluoro-2-(difluoromethyl)-1-propene (CH2=C(CHF, 22), 1,1,1,2-tetrafluoro-2-butene (CF3CF=CHCH3), 1,1,1,3-tetrafluoro-2-butene (CH3CF=CHCF3), 1,1,1,2,3,4,4,5,5,5-decafluoro-2-pentene (CF3CF=CFCF2CF3), 1,1,2,3,3,4,4,5,5,5-decafluoro-1-pentene (CF2=CFCF2CF2CF3), 1,1,1,4,4,4-hexafluoro-2-(trifluoromethyl)-2-butene ((CF3)2C=CHCF3), 1,1,1,2,4,4,5,5,5-nonafluoro 1,1,1,3,4,4,5,5,5-Nonafluoro-2-pentene (CF3CH=CFCF2CF3), 1,2,3,3,4,4,5,5,5-Nonafluoro-1-pentene (CHF=CFCF2CF2CF3), 1,1,3,3,4,4,5,5,5-Nonafluoro-1-pentene (CF2=CHCF2CF2CF3), 1,1,2,3,3,4,4,5,5,5-Nonafluoro-1-pentene (CF2=CFCF2CF2CHF2), 1,1,2,3,4,4,5,5,5-Nonafluoro-2-pentene 1,1,1,2,3,4,4,5,5-Nonafluoro-2-pentene (CF3CF=CFCF2CHF2), 1,1,1,2,3,4,5,5,5-Nonafluoro-2-pentene (CF3CF=CFCHFCF3), 1,2,3,4,4,4-Hexafluoro-3-(trifluoromethyl)-1-butene (CHF=CFCF(CF3)2), 1,1,2,4,4,4-Hexafluoro-3-(trifluoromethyl)-1-butene (CF2=CFCH(CF3)2), 1,1,1,4,4,4-Hexafluoro- 2-(trifluoromethyl)-2-butene (CF3CH=C(CF3)2), 1,1,3,4,4,4-hexafluoro-3-(trifluoromethyl)-1-butene (CF2=CHCF(CF3)2), 2,3,3,4,4,5,5,5-octafluoro-1-pentene (CH2=CFCF2CF2CF3), 1,2,3,3,4,4,5,5-octafluoro-1-pentene (CHF=CFCF2CF2CHF2), 3,3,4,4,4-pentafluoro-2-(trifluoromethyl)-1-butene (CH2=C(CF3)CF2CF3), 1,1,4,4,4-Pentafluoro-3-(trifluoromethyl)-1-butene (CF2=CHCH(CF3)2), 1,3,4,4,4-pentafluoro-3-(trifluoromethyl)-1-butene (CHF=CHCF(CF3)2), 1,1,4,4,4-pentafluoro-2-(trifluoromethyl)-1-butene (CF2=C(CF3)CH2CF3), 3,4,4,4-tetrafluoro-3-(trifluoromethyl)-1-butene ((CF3)2CFCH=CH2), 3,3,4,4,5,5,5-heptafluoro-1-pentene (CF3CF 2CF2CH=CH2), 2,3,3,4,4,5,5-heptafluoro-1-pentene (CH2=CFCF2CF2CHF2), 1,1,3,3,5,5,5-heptafluoro-1-butene (CF2=CHCF2CH2CF3), 1,1,1,2,4,4,4-heptafluoro-3-methyl-2-butene (CF3CF=C(CF3)(CH3)), 2,4,4,4-tetrafluoro-3-(trifluoromethyl)-1-butene (CH2=CFCH(CF3)2), 1,4,4,4-tetrafluoro-3-(trifluoromethyl)-1-butene ( CHF=CHCH(CF3)2), 1,1,1,4-tetrafluoro-2-(trifluoromethyl)-2-butene (CH2FCH=C(CF3)2), 1,1,1,3-tetrafluoro-2-(trifluoromethyl)-2-butene (CH3CF=C(CF3)2), 1,1,1-trifluoro-2-(trifluoromethyl)-2-butene ((CF3)2C=CHCH3), 3,4,4,5,5,5-hexafluoro-2-pentene (CF3CF2CF=CHCH3), 1,1,1,4,4,4-hexafluoro-2-methyl-2-butene (CF3 C(CH3)=CHCF3), 3,3,4,5,5,5-hexafluoro-1-pentene (CH2=CHCF2CHFCF3), 4,4,4-trifluoro-2-(trifluoromethyl)-1-butene (CH2=C(CF3)CH2CF3), 1,1,2,3,3,4,4,5,5,6,6,6-dodecafluoro-1-hexene (CF3(CF2)3CF=CF2), 1,1,1,2,2,3,4,5,5,6,6,6-dodecafluoro-3-hexene (CF3CF2CF=CFCF2CF3), 1,1,1,4,4,4-hexafluoro-2,3-bis(trifluoromethyl)-2-butene ((CF3)2C=C(CF3)2), 1,1,1,2,3,4,5,5,5-nonafluoro-4-(trifluoromethyl)-2-pentene ((CF3)2CFCF=CFCF3), 1,1,1,4,4,5,5,5-octafluoro-2-(trifluoromethyl)-2-pentene ((CF3)2C=CHC2F5), 1,1,1,3,4,5,5,5-octafluoro-4-(trifluoro, methyl)-2-pentene ((CF3)2CFCF=CHCF3), 3,3,4,4,5,5,6,6,6-nonafluoro-1-hexene (CF3CF2CF2CF2CH=CH2), 4,4,4-trifluoro-3,3-bis(trifluoromethyl)-1-butene (CH2=CHC(CF3)3), 1,1,1,4,4,4-hexafluoro-3-methyl-2-(trifluoromethyl)-2-butene ((CF3)2C=C(CH3)(CF3)), 2,3,3,5,5,5-hexafluoro-4-(trifluoromethyl)-1-pentene (CH2 =CFCF2CH(CF3)2), 1,1,1,2,4,4,5,5,5-nonafluoro-3-methyl-2-pentene (CF3CF=C(CH3)CF2CF3), 1,1,1,5,5,5-hexafluoro-4-(trifluoromethyl)-2-pentene (CF3CH=CHCH(CF3)2), 3,4,4,5,5,6,6,6-octafluoro-2-hexene (CF3CF2CF2CF=CHCH3), 3,3,4,4,5,5,6,6-octafluoro-1-hexene (CH2=CHCF2CF2CF2CHF2), 1,1,1,4,4-pentene 3,3,4,4,5,5,5-Heptafluoro-2-(trifluoromethyl)-2-pentene ((CF3)2C=CHCF2CH3), 4,4,5,5,5-pentafluoro-2-(trifluoromethyl)-1-pentene (CH2=C(CF3)CH2C2F5), 3,3,4,4,5,5,5-heptafluoro-2-methyl-1-pentene (CF3CF2CF2C(CH3)=CH2), 4,4,5,5,6,6,6-heptafluoro-2-hexene (CF3CF2CF2CH=CHCH3), 4,4,5,5,6,6,6-heptafluoro-1-hexene (CH2=CHCH2C F2C2F5), 1,1,1,2,2,3,4-heptafluoro-3-hexene (CF3CF2CF=CFC2H5), 4,5,5,5-tetrafluoro-4-(trifluoromethyl)-1-pentene (CH2=CHCH2CF(CF3)2), 1,1,1,2,5,5,5-heptafluoro-4-methyl-2-pentene (CF3CF=CHCH(CF3)(CH3)), 1,1,1,3-tetrafluoro-2-(trifluoromethyl)-2-pentene ((CF3)2C=CFC2H5), 1,1,1,2,3,4,4,5,5,6,6,7,7,7-Tetradecafluoro-2-heptene (CF3CF=CFCF2CF2C2F5), 1,1,1,2,2,3,4,5,5,6,6,7,7,7-Tetradecafluoro-3-heptene (CF3CF2CF=CFCF2C2F5), 1,1,1,3,4,4,5,5,6,6,7,7,7-Tridecafluoro-2-heptene (CF3CH=CFCF2CF2C2F5), 1,1,1,2,4,4,5,5,6,6,7,7,7-Tridecafluoro-2-heptene (CF3CH=CFCF2CF2C2F5), Ridecafluoro-2-heptene (CFCF=CHCFCFCF), 1,1,1,2,2,4,5,5,6,6,7,7,7-tridecafluoro-3-heptene (CFCFCH=CFCFCF), 1,1,1,2,2,3,5,5,6,6,7,7,7-tridecafluoro-3-heptene (CFCFCF=CHCFCF) alone or in mixtures with other HFOs, HCFOs, and HFC compounds.

[0061] In another embodiment, the unregenerated (spent) solvent includes, but is not limited to, saturated or unsaturated compounds containing only carbon, fluorine, and hydrogen atoms, and the number of carbons is from 4 to 10. Specific examples include tridecafluorooctane, decafluoropentane, pentafluorobutane, heptafluorocyclopentane, pentadecafluoroheptane, and hexafluorobutene.

[0062] In still further embodiments, unregenerated (spent) halogenated liquids, e.g., immersion coolants and solvents, include, for example, Z-1,1,1,4,4,4-hexafluoro-2-butene, 1,3,4,4,4-pentafluoro-3-trifluoromethyl-1-butene, 1,1,1,4,4,5,5,5-octafluoro-2-pentene, perfluorobutyl methyl ether, perfluorobutyl ethyl ether, perfluoroisopropyl methyl ether, perfluoroethyl isopropyl ketone, heptafluorosilane, clopentane and E-1,1,1-trifluoro-3-chloro-2-propene, alone or in combination with the fluoroethers disclosed in U.S. Pat. No. 9,840,685 B2, the disclosure of which is incorporated herein by reference in its entirety, and methylperfluoroheptene ether (MPHE) and trans-1,2-dichloroethylene, or in combination with the compositions of U.S. Pat. No. 9,428,717 B2, the disclosure of which is incorporated herein by reference in its entirety.

[0063] In still further embodiments, the unregenerated (used) liquid may include any of the immersion cooling liquids disclosed in U.S. Patent Application Publication No. 2020 / 0178414, the disclosure of which is incorporated herein by reference in its entirety.

[0064] In still further embodiments, the unregenerated (spent) liquid is (a) a compound of formula CF3(CF2) x CF=CFCF(OR)(CF2) y CF3, CF3(CF2) x C(OR)=CFCF2(CF2) y CF3, CF3CF = CFCF(OR)(CF2) x (CF2) y CF3, CF3(CF2) x CF=C(OR)CF2(CF2) y CF3, or mixtures thereof, where R can be either CH3, C2H5, or mixtures thereof, and x and y are independently 0, 1, 2, or 3, and x + y = 0, 1, 2, or 3, and (b) a compound of formula CF3(CF2) xCF=CFCF(OR)(CF2) y CF3, CF3(CF2) x C(OR)=CFCF2(CF2) y CF3, CF3CF = CFCF(OR)(CF2) x (CF2) y CF3, CF3(CF2) x CF=C(OR)CF2(CF2) y CF3, and mixtures thereof, wherein x and y are independently 0, 1, 2, 3, or 4, and x + y = 0, 1, 2, 3, or 4; and R is 2,2,3,3-tetrafluoro-1-propyl, 2,2,3,3,3-pentafluoro-1-propyl, 2,2,2-trifluoro-1-ethyl, 2,2,3,3,4,4,5,5-octafluoro-1-pentyl, or 1,1,1,3,3,3-hexafluoro-2-propyl; and (c) 5-methoxyperfluoro-3-heptene, 3-methoxyperfluoro-3-heptene, 5 ... and mixtures of compounds from (a) and (b), including, but not limited to, at least one of 4-methoxyperfluoro-3-heptene, 4-methoxyperfluoro-2-heptene, 3-methoxyperfluoro-2-heptene, or mixtures thereof, 4-methoxyperfluoro-2-pentene, 2-methoxyperfluoro-2-pentene, 3-methoxyperfluoro-2-pentene, 2-methoxyperfluoro-3-pentene, or mixtures thereof, and at least one of cis- and trans-2-methoxyperfluoro-2-octene, 2-methoxyperfluoro-3-octene, or mixtures thereof.

[0065] The regenerated halogenated liquid, in a quantity and type as described herein, is transferred from the recovery / collection system 110, and the liquid is analyzed in a station or system 120 to detect and measure impurities, including, but not limited to, NAG (non-absorbable gas), acid, solids, water, and / or high-boiling residual content, as needed, to determine its quantity. The unregenerated halogenated liquid, e.g., refrigerant, liquid blowing agent, solvent, immersion cooling fluid, is analyzed using analytical techniques such as GC-FID, GC-TCD, GC-MS, FTIR, Goetz Bub, Karl Fischer, Byk-Garner Color, and various other analytical methods to determine and optionally confirm the identity of the unregenerated halogenated liquid. Typically, organic product analysis involves gas chromatography (GC / MS) or liquid chromatography.

[0066] The concentration of non-condensable gas (NCG) or non-absorbable gas (NAG) may be varied or modified to achieve a concentration of less than 1.5 volume percent at 25°C per AHRI 700, preferably less than 0.9 volume percent at 25°C per AHRI 700. NAG typically includes air (typically composed of 78% nitrogen, 21% oxygen, and about 1% argon) accumulated in the vapor phase of refrigerants where air has very low solubility in the liquid phase. While it can be important to reduce the total amount of NAG contained within the liquid, it is typically more desirable to reduce the oxygen-containing portion of the NAG preferentially over the nitrogen portion. Under certain circumstances, the oxygen-containing portion may increase the tendency of certain olefins to decompose or form unwanted polymeric materials. NCG can be detected using one of an infrared sensor, a UV sensor, an NIR sensor, an ion mobility or plasma chromatography, a gas chromatography, a refractive index measurement, a mass spectrometry, a high temperature thick film sensor, a thin film field effect sensor, a pellistor sensor, a Taguchi sensor, and a quartz crystal microbalance sensor, as disclosed in U.S. Patent Application Publication No. 2008 / 0069177, which is incorporated herein by reference in its entirety.

[0067] The unregenerated liquid components or composition, even if provided by a customer, can be analyzed as described above to evaluate the physical and chemical properties of the unregenerated liquid composition and perform a purity check to see how it compares to the AHRI-700 industry standard. Based on the analytical (test) results from the weighing and testing station, i.e., system 120, a first or primary purification is performed using a distillation column (adsorption / desorption and cryogenic cooling, and / or other separation techniques) in system 130, and the first-stage purified liquid is reanalyzed and reconfirmed for purity. The first or primary purification system optionally includes a column containing an absorbent / adsorbent to remove inhibitors and / or stabilizers in the unregenerated liquid composition as disclosed herein. The column (not shown) can be upstream or downstream of the distillation component of system 130. If silica gel or other molecular sieve material is used as a medium for removing inhibitors and / or stabilizers, the unregenerated liquid can be passed through a bed of silica gel, and the inhibitor-free "partially" regenerated product can be optionally transferred to one or more distillation columns to separate and isolate the individual liquid components. If the primary purification does not provide a treated product that meets AHRI-700 standards, it can be transferred from system 130 to system 140 for further processing, including targeted purification for NAG (purge station), water (distillation / desiccant dryer), solids (filter), acidity (base bath), and high-boiling residue / chlorides (distillation), where it is reanalyzed and reconfirmed in a weighing and testing station to verify purity and industry compliance in system 140. A NAG reduction station (not shown) can contact the partially regenerated liquid composition with a reducing agent, such as a metal powder, which can react with oxygen or other oxidizable components of the unregenerated liquid composition. In one embodiment, the reducing agent can include iron powder. Treatment by the NAG reduction station may reduce the concentration of one or more components of the partially regenerated liquid composition to below one or more predetermined thresholds.

[0068] Thereafter, in system 150, the regenerated liquid components from 130 or 140 are mixed with additional fresh / virgin / high-purity liquid components to provide a reconstituted, compositionally rebalanced, regenerated liquid, e.g., refrigerant, solvent, immersion coolant, blowing agent, composition, that meets AHRI 700-19 standards in system 150. Tracers, stabilizers, and conventional additives are added in system 160, and then a final purity check is performed to ensure that the regenerated and reconstituted liquid is AHRI 700-19 compliant. Each system 110, 120, 130, 140, 150, and 160 includes components for receiving and transferring liquid compositions between upstream and downstream systems, such as flow lines, valves, pumps, controls (not shown), etc.

[0069] In another embodiment, the NAG is separated from the refrigerant using a membrane positioned such that the NAG can pass through the membrane and be removed while the refrigerant does not pass through the membrane.

[0070] In Figure 2, system 200 illustrates a non-limiting example of a system and method for foam waste recycling. Foam waste, including but not limited to rigid polyurethane, is delivered, collected, sorted, and weighed in recovery system 210, and then, after sorting and weighing, transferred to processing system 220, where the dimensions of the foam waste are physically reduced to a suitable size by crushing or other techniques. If the foam waste contains closed cells, the rigid polyurethane foam, foam blowing agent, and air remain within the cells. When the rigid foam is crushed, crushed, or shredded, the blowing agent and air are released. The released blowing agents include, but are not limited to, combinations of HFC and / or HFO components selected from HFC-134a, HFC-245fa, HFC-365mfc, HFC-227ea, HCFO1233zd(E), HCFO-1224yd(Z), HFO-1336mzz(E), and HFO-1336mzz(Z). Hydrocarbons such as cyclopentane, isopentane, and normal pentane may also be included. Generally, the released foam gas is composed of 50-99.5% by volume air, with the remainder composed of HFCs and / or HFOs. Concentrations can vary depending on the amount of blowing agent used to create the foam, the amount lost to the atmosphere during the foam's lifetime, the amount of air permeating the foam during its lifetime, and the amount of air introduced during the regeneration and / or recycling process, as well as the efficiency of foam milling.

[0071] Because the treatment zone is typically operated under reduced pressure, a vapor stream is formed and sent from system 240 to one of purification systems 130 and / or 140, or to a dedicated distillation system (not shown). Preferably, the foam gas composition is known prior to processing, since recovering the blowing agent is a simpler process for pure HFC or HFO / air mixtures. However, because the integrated regeneration system includes a testing station to identify the components of the regenerated product, vapors removed during crushing can be analyzed prior to purification. Crushed and / or pelletized foam waste from system 220 is collected and stored.

[0072] In Figure 3, foam waste is sent through a process under vacuum (partial or total) where the foam is crushed and pulverized under vacuum, and the vapor stream is sent to a distillation process for liquid recovery. The solids are sent to a pelletizer for subsequent recycling. Once the foam is crushed, the remaining solid portion is no longer foam, but polyurethane solids. These solids can be recovered, pelletized, or compacted, incinerated for fuel value, used as concrete filler, or recycled by glycolysis to chemically reduce the solids to a liquid polyol, which can be used again to make another polyurethane foam.

[0073] Because the crushing process is performed under vacuum, excess air is minimized, and distillation separates primarily CO2, 1336mzzZ / E, 1233zdE, 1224ydZ, and / or air. The vapor stream from the crusher is sent to a vessel containing a liquid (e.g., 1336mzzZ or 1233zdE). By bubbling the vapor through the liquid, a gas absorber can capture the blowing agent, which is then sent to the distillation operation of system 130 or 140 for purification.

[0074] FIG. 4 shows a non-limiting example of a service center 400 including one or more systems 110, 120, 130, 140, 150, and 160 that can be connected to a mobile transport vehicle 420 to input regenerated refrigerant / refrigerant blends from system 410 via line 412 or re-input refrigerants or refrigerant blends that have been processed in system 410 via line 412, and optionally withdraw used refrigerant from vehicle 420 via line 422 for processing within system 410.

[0075] FIG. 5 shows a system 500 for purifying unregenerated (unpurified) refrigerant liquid from a mixture of N chemically distinct liquids collected in unit 510 in step 1, which contains an unpurified liquid mixture, Liquid 1, Liquid 2, ..., Liquid N. In step 2, the liquid components of the liquid mixture are separated by a separation process, such as distillation. In step 3, the unpurified separated liquid may require further processing, such as additional distillative removal of NAG. In step 4, the purified liquid components from step 4 are compared to industry-quality standards, including removal of moisture, solids, and volatile impurities. In step 5, additive and / or tracer components are introduced into each purified individual component. In step 6, the separated, purified, and added components can be recombined into other blends or used as pure components.

[0076] 6 shows a service center system 600 in which a source of regenerated / reblended refrigerant 610 from a system such as that shown in FIG. 5 is connected to a refrigerant circuit 650 of a transportation vehicle (not shown), which generally includes, in series, an input valve 612, an expansion device 614, a heat exchange section 620, a compressor 630, a heat exchange section 640, and flow lines 613, 615, 622, 631, and 641. The regenerated / reblended refrigerant 610 is input via line 611 in fluid communication with input valve 612, and is input to refrigerant circuit 650 when input valve 612 is opened.

[0077] One embodiment disclosed herein comprises a system including a contained supply of regenerated / reblended refrigerant, a refrigerant circuit including at least an input valve and a compressor, and a controllable transfer line connecting the contained supply of regenerated / reblended refrigerant to the input valve of the circuit. Another embodiment disclosed herein comprises a purification system, a contained supply of purified refrigerant that receives a product from the purification system, a refrigerant circuit including at least an input valve and a compressor, and a controllable transfer line connecting the contained supply of regenerated / reblended refrigerant to the input valve.

[0078] Additional Embodiments a) treating foam waste and / or spent halogenated liquid to produce a reclaimed foam polymer or a reclaimed halogenated liquid, wherein the foam waste or spent halogenated liquid is selected from one of refrigerants and refrigerant blends, blowing agents, solvents, and immersion coolants; and b) collecting or packaging the halogenated liquid components and foam waste. Prior to step a), the waste or spent halogenated liquid is recovered from various sources, such as systems circulating heat transfer liquids, storage facilities, or sources of unwanted refrigerant.

[0079] Process embodiments in which the spent halogenated liquid of a) is treated to comprise at least one of chlorofluoroolefins (CFOs), hydrochloroolefins (HCOs), hydrofluoroolefins (HFOs), hydrochlorofluoroolefins (HCFOs), hydrofluoroethers (HFEs), hydrofluoroolefin ethers (HFOEs), hydrofluoroketones (HFKs), fluoroketones (FKs), or a) is foam waste and is treated by shredding.

[0080] A process embodiment in which the foam waste and / or spent halogenated liquid of a) is collected from the unrecycled foam waste or unrecycled halogenated liquid prior to processing in (i)a).

[0081] A process embodiment wherein the unregenerated halogenated liquid of a) is analyzed prior to a) to determine the composition of the unregenerated halogenated liquid and the presence and nature of any contaminants.

[0082] A process embodiment wherein the physical and chemical properties of the unregenerated halogenated liquid are determined prior to a).

[0083] The process embodiment of a) wherein the treating includes physical and chemical treatment.

[0084] The process embodiment, wherein the treating of a) comprises at least one of water removal, contaminant removal, and distillation.

[0085] a1) an unregenerated halogenated liquid selected from chlorofluoroolefins (CFOs), hydrochloroolefins (HCOs), hydrofluoroolefins (HFOs), hydrochlorofluoroolefins (HCFOs), hydrofluoroethers (HFEs), hydrofluoroolefin ethers (HFOEs), fluoroketones (FKs), hydrofluoroketones (HFKs), and mixtures of two or more; a2) optionally identifying the contaminants of a1); a3) selecting a physical and / or chemical treatment based on a1) and optionally a2); and a4) treating the unregenerated halogenated liquids of a1) and a2) using the physical and / or chemical treatment selected in step a3). a5) comparing the purity of the at least partially regenerated halogenated liquid of a3) to an industry standard; a6) optionally further processing the partially unregenerated halogenated liquid of a3) to produce a fully regenerated halogenated liquid; a7) optionally comparing the purity of the at least partially regenerated halogenated liquid of a5) to an industry standard; a8) optionally compositionally re-equilibrating the partially or fully regenerated halogenated liquid to an industry-compatible product; and a9) collecting or packaging the product of a8).

[0086] A process embodiment in which the post-consumer waste of a) comprises halogenated hydrocarbon-generating foam, and ab) the foam is crushed under vacuum to produce crushed foam and a vapor stream, and the vapor stream is removed from the crushed foam.

[0087] A process embodiment wherein the crushed foam of ab) is isolated and pelletized.

[0088] Process embodiments in which the spent halogenated liquid of a) or the unregenerated halogenated liquid of a1) is selected from one of HFO-E / Z-1336mzz, HCFO-E / Z-1224yd, HCFO-E / Z-1233zd, R-514A (an olefin blend composed of cis-1,1,1,4,4,4-hexafluorobut-2-ene (R-1336mzz(Z)) and trans-1,2-dichloroethene (R-1130(E), HFO-Z / E 1336mzz blend, liquid HFC-245fa, and Vertrel XF.

[0089] A process embodiment in which the spent halogenated liquid of a) or the unregenerated halogenated liquid of a1) is selected from one of Vertrel XF, SF10, SF79, SF80, SF01, SF05, SF30, SF33, F33E, F22E, and F44E (see Tables 1-4).

[0090] The process embodiment, wherein the spent halogenated liquid of a) or the unregenerated halogenated liquid of a1) is selected from halogenated liquids and comprises one of a hydrofluoroether (HFE) and a hydrofluoroolefin ether (HFOE).

[0091] Process embodiments in which the used halogenated liquid of a) or the unregenerated halogenated liquid of a1) is a hydrofluoroether (HFE) and comprises one of Novec 7100, Novec 7200, Novec 7300, Novec 7500, Novec 71DE, Novec 71DA, Novec 72DA, Novec 72DE, Novec 71IPA, and Novec 73DE (see Table 1).

[0092] Process embodiments in which the spent halogenated liquid of a) or the unregenerated halogenated liquid of a1) comprises a chlorofluoroolefin (CFO), a hydrochloroolefin (HCO), a hydrochlorofluoroolefin (HCFO), a fluoroketone (FK), or a hydrofluoroketone (HFK).

[0093] A process embodiment in which the spent halogenated liquid of a) or the unregenerated halogenated liquid of a1) is regenerated, and a tracer is added to at least one of the partially regenerated or fully regenerated halogenated liquid.

[0094] A process embodiment in which the spent halogenated liquid of a) or the unregenerated halogenated liquid of a1) is regenerated, and a stabilizer package is added to at least one of the partially regenerated or fully regenerated halogenated liquids, comprising at least one antioxidant, at least one acid acceptor, and at least one metal stabilizer, wherein the antioxidant is selected from butylated hydroxytoluene, butylated hydroxyanisole, tert-butylhydroquinone, 4-methoxyphenol, propyl 3,4,5-trihydroxybenzoate, the acid acceptor is selected from epoxybutane, amines, and acetaldehyde di-methylhydrazone (ADH), and the metal stabilizer is selected from N,N'-bis(salicylidene)-1,2-propanediamine, benzotriazole, and derivatives thereof.

[0095] Process embodiments wherein the spent halogenated liquid of a) or the unregenerated halogenated liquid of a1) comprises a HFO-E / Z-1336mzz and HFO-Z / E 1336mzz blend.

[0096] The process embodiment wherein the spent halogenated liquid of a) or the unregenerated halogenated liquid of a1) comprises HCFO-E / Z-1224yd.

[0097] The process embodiment wherein the spent halogenated liquid of a) or the unregenerated halogenated liquid of a1) comprises HCFO-E / Z-1233zd.

[0098] Process embodiments wherein the spent halogenated liquid of a) or the unregenerated halogenated liquid of a1) comprises cis-1,1,1,4,4,4-hexafluorobut-2-ene (R-1336mzz(Z)) and trans-1,2-dichloroethene (R-1130(E)).

[0099] Process embodiments wherein the spent halogenated liquid of a) or the unregenerated halogenated liquid of a1) comprises Vertrel XF (1,1,1,2,3,4,4,5,5,5-decafluoropentane).

[0100] The used halogenated liquid in a) or the unregenerated halogenated liquid in a1) may be a blend of MPHE (Opteon™ SF10), 94% trans-1,2-dichloroethylene, 5% MPHE, and 1% Vertrel XF (1,1,1,2,3,4,4,5,5,5-decafluoropentane (Opteon™ SF79), 94% trans-1,2-dichloroethylene, 5% MPHE, and 1% Z-1336mzz (Opteon™ SF80), 98.4% Z-1336mzz and 1.6% ethanol (Opteon™ SF01), 60% Z-1336mzz, 25% MPHE, and 15% ethanol (Opteon™ SF05), 75% Z-1336mzz and 25% trans (Z)-1,2-dichloroethylene (Opteon™ SF30), (Z)-1,1,1,4,4,4-hexafluoro-2-butene (Opteon™ SF33), 1,1,1,2,2,3,3,6,6,7,7,8,8,8-tetradecafluoro-4-octene (F33E), 1,1,1,2,2,5,5,6,6,6-decafluorohex-3-ene (F22E), and 1,1,1,2,2,3,3,4,4,7,7,8,8,9,9,10,10,10-octadecafluorodec-5-ene (F44E).

[0101] A process embodiment wherein the spent halogenated liquid of a) or the unregenerated halogenated liquid of a1) comprises a chlorofluoroolefin.

[0102] Process embodiments wherein the spent halogenated liquid of a) or the unregenerated halogenated liquid of a1) comprises hydrofluoroketone (HFK).

[0103] Composition embodiments of partially or completely regenerated spent halogenated liquids of a) or unregenerated halogenated liquids of a1).

[0104] A system or method using an embodiment, comprising: - a non-recycled liquid collection station; - waste foam collection station; - a weighing / dosing and testing station for measuring HFO-E / Z-1336mzz, HCFO-E / Z-1224yd, HCFO-E / Z-1233zd, R-514A (an olefin blend composed of cis-1,1,1,4,4,4-hexafluorobut-2-ene (R-1336mzz(Z)) and trans-1,2-dichloroethene (R-1130(E))), HFO-Z / E 1336mzz blend, liquid HFC-245fa, 1,1,1,2,3,4,4,5,5,5-decafluoropentane (Vertrel XF), MPHE (Opteon™ SF10), 94% trans-1,2-dichloroethylene, 5% MPHE, and 1% Vertrel XF (a blend containing 1,1,1,2,3,4,4,5,5,5-decafluoropentane (Opteon™ SF79), a blend containing 94% trans-1,2-dichloroethylene, 5% MPHE, and 1% Z-1336mzz (Opteon™ SF80), a blend containing 98.4% Z-1336mzz and 1.6% ethanol (Opteon™ SF01), a blend containing 60% Z-1336mzz, 25% MPHE, and 15% ethanol (Opteon™ SF05), a blend containing 75% Z-1336mzz and 25% trans-1,2-dichloroethylene (Opteon™ SF06), a blend containing 10% Z-1336mzz and 1.6% ethanol (Opteon™ SF07), a blend containing 10% Z-1336mzz and 1.6% ethanol (Opteon™ SF08), a blend containing 10% Z-1336mzz and 1.6% ethanol (Opteon™ SF09 ... a weigh / weigh and test station comprising an analytical system for determining physical and chemical properties of an unregenerated liquid selected from one of: (Z)-1,1,1,4,4,4-hexafluoro-2-butene (Opteon™ SF30), (Z)-1,1,1,4,4,4-hexafluoro-2-butene (Opteon™ SF33), 1,1,1,2,2,3,3,6,6,7,7,8,8,8-tetradecafluoro-4-octene (F33E), 1,1,1,2,2,5,5,6,6,6-decafluorohex-3-ene (F22E), 1,1,1,2,2,3,3,4,4,7,7,8,8,9,9,10,10,10-octadecafluorodec-5-ene (F44E); a waste foam processing station comprising at least one crusher, at least one solids separator, at least one pelletizer with steam separation; a first purification system for receiving and treating unregenerated liquid from the weighing and testing station, vapor from the waste foam treatment station, and a first transfer line; a second purification system for receiving and processing liquid from the first purification system and the second transfer line; - a target refrigerant system including a blending station in fluid communication with the first and second transfer lines for receiving treated liquid from the first and second purification systems to adjust the levels of regenerated liquid constituents to target refrigerant levels of the AHRI 700 standard following purification at the first and second purification stations, and for providing a regenerated liquid blend constituent consistent with the AHRI 700 standard; - a stabilizer package dispensing station for adding an effective amount of a stabilizer package comprising at least one antioxidant, at least one acid acceptor, and at least one metal stabilizer; a purity verification station for verifying the purity of the unregenerated liquid before purification, the purity after the first and / or second purification treatments, and the purity of the at least one first treated product, and determining whether the first treated product meets or exceeds AHRI 700 standards.

[0105] A system or method using an embodiment wherein the weighing and testing station includes at least one of a balance, a GC-FID, a GC-TCD, a GC-MS, an FTIR, a Goetz Bub, a Karl Fischer, and a Byk-Garner Color detector.

[0106] A system or method using an embodiment, wherein the weighing and testing station includes one of an infrared sensor, a UV sensor, a NIR sensor, an ion mobility or plasma chromatograph, a gas chromatography, a refractive index measurement, a mass spectrometry, a high temperature thick film sensor, a thin film field effect sensor, a pellistor sensor, a Taguchi sensor, and a quartz crystal microbalance sensor.

[0107] A system or method using an embodiment wherein the weighing and testing station includes a scale, a GC-MS, and a Taguchi sensor.

[0108] A system or method using an embodiment wherein at least one of the first and second purification systems includes one of a distillation column, an adsorption / desorption column, and a cryogenic refrigerator.

[0109] A system or method using an embodiment, wherein at least one of the first and second purification systems includes one of an NCG purge unit, a water distillation or desiccant dryer unit, a solids filter unit, and an acidity neutralizer, and a high distillation bottoms column.

[0110] (a) Formula CF3(CF2) x CF=CFCF(OR)(CF2) y CF3, CF3(CF2) x C(OR)=CFCF2(CF2) y CF3, CF3CF = CFCF(OR)(CF2) x (CF2) y CF3, CF3(CF2) x CF=C(OR)CF2(CF2) y CF3, or mixtures thereof (wherein R can be either CH3, C2H5, or mixtures thereof, and x and y are independently 0, 1, 2, or 3, where x + y = 0, 1, 2, or 3); and (b) a regenerated compound of formula CF3(CF2). x CF=CFCF(OR)(CF2) y CF3, CF3(CF2) x C(OR)=CFCF2(CF2) y CF3, CF3CF = CFCF(OR)(CF2) x (CF2) y CF3, CF3(CF2) x CF=C(OR)CF2(CF2) yCF3, and mixtures thereof (wherein x and y are independently 0, 1, 2, 3, or 4, x + y = 0, 1, 2, 3, or 4, and R is 2,2,3,3-tetrafluoro-1-propyl, 2,2,3,3,3-pentafluoro-1-propyl, 2,2,2-trifluoro-1-ethyl, 2,2,3,3,4,4,5,5-octafluoro-1-pentyl, or 1,1,1,3,3,3-hexafluoro-2-propyl), and (c) 5-methoxyperfluoro-3-heptene, 3-methoxyperfluoro-3-heptene, 4-methoxyperfluoro-2-heptene, 3 and a mixture of compounds from (a) and (b), including, but not limited to, at least one of cis- and trans-2-methoxyperfluoro-2-octene, 2-methoxyperfluoro-3-octene, or mixtures thereof, 4-methoxyperfluoro-2-heptene, 4-methoxyperfluoro-2-pentene, 2-methoxyperfluoro-2-pentene, 3-methoxyperfluoro-2-pentene, 2-methoxyperfluoro-3-pentene, or mixtures thereof, and at least one of cis- and trans-2-methoxyperfluoro-2-octene, 2-methoxyperfluoro-3-octene, or mixtures thereof.

[0111] Regenerated hydrofluoroethers (HFEs), such as methoxy-nonafluorobutane (Novec™ 7100), ethoxy-nonafluorobutane (Novec™ 7200), 1,1,1,2,2,3,4,5,5,5-decafluoro-3-methoxy-4-(trifluoromethyl)pentane (Novec™ 7300), 3-ethoxy-1,1,1,2,3,4,4,5,5,6,6,6-dodecafluoro-2-(trifluoromethyl)pentane (Novec™ 7400), (fluoromethyl)hexane (Novec™ 7500), dodecafluoro-2-methylpentan-3-one (Novec™ 649), a blend containing 50% methyl nonafluorobutyl ether and 50% trans-1,2-dichloroethylene (Novec™ 71DE), a blend containing 52.7% methyl nonafluorobutyl ether, 44.6% trans-1,2-dichloroethylene, and 2.7% ethanol. and / or a blend comprising 1,1,1,2,2,3,4,5,5,5-decafluoro-3-methoxy-4-(trifluoromethyl)pentane and trans-1,2-dichloroethylene (Novec™ 73DE).

[0112] Processes using embodiments in which recycled hydrofluoroketones (HFK) (Novec 649) including but not limited to trifluoroacetone, dodecafluoro-2-methylpentan-3-one are used to exchange heat.

[0113] HFO-E / Z-1336mzz, HCFO-E / Z-1224yd, HCFO-E / Z1233zd, R-514A (an olefin blend composed of cis-1,1,1,4,4,4-hexafluorobut-2-ene (R-1336mzz(Z)) and trans-1,2-dichloroethene (R-1130(E))), HFO-Z / E 1336mzz blend, liquid HFC-245fa, 1,1,1,2,3,4,4,5,5,5-decafluoropentane (Vertrel XF), MPHE (Opteon™ SF10), 94% trans-1,2-dichloroethylene, 5% MPHE, and 1% Vertrel XF (a blend containing 1,1,1,2,3,4,4,5,5,5-decafluoropentane (Opteon™ SF79), a blend containing 94% trans-1,2-dichloroethylene, 5% MPHE, and 1% Z-1336mzz (Opteon™ SF80), a blend containing 98.4% Z-1336mzz and 1.6% ethanol (Opteon™ SF01), a blend containing 60% Z-1336mzz, 25% MPHE, and 15% ethanol (Opteon™ SF05), a blend containing 75% Z-1336mzz and 25% trans-1,2-dichloroethylene (Opteon™ SF06), a blend containing 1,1,1,2,3,4,4,5,5,5-decafluoropentane (Opteon™ SF79), a blend containing 94% trans-1,2-dichloroethylene, 5% MPHE, and 1% Z-1336mzz (Opteon™ SF80), a blend containing 98.4% Z-1336mzz and 1.6% ethanol (Opteon™ SF01), a blend containing 60% Z-1336mzz, 25% MPHE, and 15% ethanol (Opteon™ SF06), a blend containing 75% Z-1336mzz and 25% trans-1,2-dichloroethylene (Opteon™ SF06), a blend containing 1,1,1,2,3,4,4,5,5,5-decafluoropentane (Opteon™ SF79), a blend containing 1,1,1,2,3,4,4,5,5,5-decafluoropentane (Opteon™ SF80), a blend containing 1,1,1,2,3,4,4,5,5,5-decafluoropentane (Opteon™ 10. A process using an embodiment in which heat is exchanged using a regenerated fluid selected from a blend containing ethylene (Opteon™ SF30), (Z)-1,1,1,4,4,4-hexafluoro-2-butene (Opteon™ SF33), 1,1,1,2,2,3,3,6,6,7,7,8,8,8-tetradecafluoro-4-octene (F33E), 1,1,1,2,2,5,5,6,6,6-decafluorohex-3-ene (F22E), and 1,1,1,2,2,3,3,4,4,7,7,8,8,9,9,10,10,10-octadecafluorodec-5-ene (F44E).

[0114] Recycled fluorinated and perfluorinated C4-C7 unsaturated compounds, such as 1,1,1,2,3,4,4,4-octafluoro-2-butene (CF3CF=CFCF3), 1,1,2,3,3,4,4,4-octafluoro-1-butene (CF3CF2CF=CF2), 1,1,1,2,4,4,4-heptafluoro-2-butene (CF3CF=CHCF3), 1,2,3,3,4,4,4-heptafluoro-1-butene (CHF=CFCF2CF3), 1,1,1,2,3,4,4-heptafluoro-2-butene (CHF2CF=CFCF3), 1,3,3 ,3-Tetrafluoro-2-(trifluoromethyl)-1-propene ((CF3)2C=CHF), 1,1,3,3,4,4,4-heptafluoro-1-butene (CF2=CHCF2CF3), 1,1,2,3,4,4,4-heptafluoro-1-butene (CF2=CFCHFCF3), 1,1,2,3,3,4,4-heptafluoro-1-butene (CF2=CFCF2CHF2), 2,3,3,4,4,4-hexafluoro-1-butene (CF3CF2CF=CH2), 1,3,3,4,4,4-hexafluoro-1-butene (CHF=CHCF2C F3), 1,2,3,4,4,4-hexafluoro-1-butene (CHF=CFCHFCF3), 1,2,3,3,4,4-hexafluoro-1-butene (CHF=CFCF2CHF2), 1,1,2,3,4,4-hexafluoro-2-butene (CHF2CF=CFCHF2), 1,1,1,2,3,4-hexafluoro-2-butene (CH2FCF=CFCF3), 1,1,1,2,4,4-hexafluoro-2-butene (CHF2CH=CFCF3), 1,1,1,3,4,4-hexafluoro-2-butene (CF3CH=CFCHF2), 1, 1,2,3,3,4-Hexafluoro-1-butene (CF2=CFCF2CH2F), 1,1,2,3,4,4-Hexafluoro-1-butene (CF2=CFCHFCHF2), 3,3,3-Trifluoro-2-(trifluoromethyl)-1-propene (CH2=C(CF3)2), 1,1,1,2,4-Pentafluoro-2-butene (CH2FCH=CFCF3), 1,1,1,3,4-Pentafluoro-2-butene (CF3CH=CFCH2F), 3,3,4,4,4-Pentafluoro-1-butene (CF3CF2CH=CH2), 1,1,1,4,4-Pentafluoro-2-butene (CHF2CH=CHCF3), 1,1,1,2,3-pentafluoro-2-butene (CH3CF=CFCF3), 2,3,3,4,4-pentafluoro-1-butene (CH2=CFCF2CHF2), 1,1,2,4,4-pentafluoro-2-butene (CHF2CF=CHCHF2), 1,1,2,3,3-pentafluoro-1-butene (C H3CF2CF=CF2), 1,1,2,3,4-pentafluoro-2-butene (CH2FCF=CFCHF2), 1,1,3,3,3-pentafluoro-2-methyl-1-propene (CF2=C(CF3)(CH3)), 2-(difluoromethyl)-3,3,3-trifluoro-1-propene (CH2=C(CHF2)(CF3)), 2,3,4,4,4-pentafluoro-1- Butene (CH2=CFCHFCF3), 1,2,4,4,4-pentafluoro-1-butene (CHF=CFCH2CF3), 1,3,4,4,4-pentafluoro-1-butene (CHF=CHCHFCF3), 1,3,3,4,4-pentafluoro-1-butene (CHF=CHCF2CHF2), 1,2,3,4,4-pentafluoro-1-butene (CHF=CFCHFCHF2) , 3,3,4,4-tetrafluoro-1-butene (CH2=CHCF2CHF2), 1,1-difluoro-2-(difluoromethyl)-1-propene (CF2=C(CHF2)(CH3)), 1,3,3,3-tetrafluoro-2-methyl-1-propene (CHF=C(CF3(CH3)), 3,3-difluoro-2-(difluoromethyl)-1-propene (CH2=C(CHF, 22), 1,1,1,2-tetrafluoro-2-butene (CF3CF=CHCH3), 1,1,1,3-tetrafluoro-2-butene (CH3CF=CHCF3), 1,1,1,2,3,4,4,5,5,5-decafluoro-2-pentene (CF3CF=CFCF2CF3), 1,1,2,3,3,4,4,5,5,5-decafluoro-1-pentene (CF2=CFCF2CF2CF3), 1,1,1,4,4,4-hexafluoro-2-(trifluoromethyl)-2-butene ((CF3)2C=CHCF3), 1,1,1,2,4,4,5,5,5-nonafluoro 1,1,1,3,4,4,5,5,5-Nonafluoro-2-pentene (CF3CH=CFCF2CF3), 1,2,3,3,4,4,5,5,5-Nonafluoro-1-pentene (CHF=CFCF2CF2CF3), 1,1,3,3,4,4,5,5,5-Nonafluoro-1-pentene (CF2=CHCF2CF2CF3), 1,1,2,3,3,4,4,5,5,5-Nonafluoro-1-pentene (CF2=CFCF2CF2CHF2), 1,1,2,3,4,4,5,5,5-Nonafluoro-2-pentene 1,1,1,2,3,4,4,5,5-Nonafluoro-2-pentene (CF3CF=CFCF2CHF2), 1,1,1,2,3,4,5,5,5-Nonafluoro-2-pentene (CF3CF=CFCHFCF3), 1,2,3,4,4,4-Hexafluoro-3-(trifluoromethyl)-1-butene (CHF=CFCF(CF3)2), 1,1,2,4,4,4-Hexafluoro-3-(trifluoromethyl)-1-butene (CF2=CFCH(CF3)2), 1,1,1,4,4,4-Hexafluoro- 2-(trifluoromethyl)-2-butene (CF3CH=C(CF3)2), 1,1,3,4,4,4-hexafluoro-3-(trifluoromethyl)-1-butene (CF2=CHCF(CF3)2), 2,3,3,4,4,5,5,5-octafluoro-1-pentene (CH2=CFCF2CF2CF3), 1,2,3,3,4,4,5,5-octafluoro-1-pentene (CHF=CFCF2CF2CHF2), 3,3,4,4,4-pentafluoro-2-(trifluoromethyl)-1-butene (CH2=C(CF3)CF2CF3), 1,1,4,4,4-Pentafluoro-3-(trifluoromethyl)-1-butene (CF2=CHCH(CF3)2), 1,3,4,4,4-pentafluoro-3-(trifluoromethyl)-1-butene (CHF=CHCF(CF3)2), 1,1,4,4,4-pentafluoro-2-(trifluoromethyl)-1-butene (CF2=C(CF3)CH2CF3), 3,4,4,4-tetrafluoro-3-(trifluoromethyl)-1-butene ((CF3)2CFCH=CH2), 3,3,4,4,5,5,5-heptafluoro-1-pentene (CF3CF 2CF2CH=CH2), 2,3,3,4,4,5,5-heptafluoro-1-pentene (CH2=CFCF2CF2CHF2), 1,1,3,3,5,5,5-heptafluoro-1-butene (CF2=CHCF2CH2CF3), 1,1,1,2,4,4,4-heptafluoro-3-methyl-2-butene (CF3CF=C(CF3)(CH3)), 2,4,4,4-tetrafluoro-3-(trifluoromethyl)-1-butene (CH2=CFCH(CF3)2), 1,4,4,4-tetrafluoro-3-(trifluoromethyl)-1-butene ( CHF=CHCH(CF3)2), 1,1,1,4-tetrafluoro-2-(trifluoromethyl)-2-butene (CH2FCH=C(CF3)2), 1,1,1,3-tetrafluoro-2-(trifluoromethyl)-2-butene (CH3CF=C(CF3)2), 1,1,1-trifluoro-2-(trifluoromethyl)-2-butene ((CF3)2C=CHCH3), 3,4,4,5,5,5-hexafluoro-2-pentene (CF3CF2CF=CHCH3), 1,1,1,4,4,4-hexafluoro-2-methyl-2-butene (CF3 C(CH3)=CHCF3), 3,3,4,5,5,5-hexafluoro-1-pentene (CH2=CHCF2CHFCF3), 4,4,4-trifluoro-2-(trifluoromethyl)-1-butene (CH2=C(CF3)CH2CF3), 1,1,2,3,3,4,4,5,5,6,6,6-dodecafluoro-1-hexene (CF3(CF2)3CF=CF2), 1,1,1,2,2,3,4,5,5,6,6,6-dodecafluoro-3-hexene (CF3CF2CF=CFCF2CF3), 1,1,1,4,4,4-hexafluoro-2,3-bis(trifluoromethyl)-2-butene ((CF3)2C=C(CF3)2), 1,1,1,2,3,4,5,5,5-nonafluoro-4-(trifluoromethyl)-2-pentene ((CF3)2CFCF=CFCF3), 1,1,1,4,4,5,5,5-octafluoro-2-(trifluoromethyl)-2-pentene ((CF3)2C=CHC2F5), 1,1,1,3,4,5,5,5-octafluoro-4-(trifluoromethyl)-2-pentene ((CF3), 2CFCF=CHCF3), 3,3,4,4,5,5,6,6,6-nonafluoro-1-hexene (CF3CF2CF2CF2CH=CH2), 4,4,4-trifluoro-3,3-bis(trifluoromethyl)-1-butene (CH2=CHC(CF3)3), 1,1,1,4,4,4-hexafluoro-3-methyl-2-(trifluoromethyl)-2-butene ((CF3)2C=C(CH3)(CF3)), 2,3,3,5,5,5-hexafluoro-4-(trifluoromethyl)-1-pentene (CH2=CFCF2CH(CF3) 2), 1,1,1,2,4,4,5,5,5-nonafluoro-3-methyl-2-pentene (CF3CF=C(CH3)CF2CF3), 1,1,1,5,5,5-hexafluoro-4-(trifluoromethyl)-2-pentene (CF3CH=CHCH(CF3)2), 3,4,4,5,5,6,6,6-octafluoro-2-hexene (CF3CF2CF2CF=CHCH3), 3,3,4,4,5,5,6,6-octafluoro-1-hexene (CH2=CHCF2CF2CF2CHF2), 1,1,1,4,4-pentafluoro-2-( trifluoromethyl)-2-pentene ((CF3)2C=CHCF2CH3), 4,4,5,5,5-pentafluoro-2-(trifluoromethyl)-1-pentene (CH2=C(CF3)CH2C2F5), 3,3,4,4,5,5,5-heptafluoro-2-methyl-1-pentene (CF3CF2CF2C(CH3)=CH2), 4,4,5,5,6,6,6-heptafluoro-2-hexene (CF3CF2CF2CH=CHCH3), 4,4,5,5,6,6,6-heptafluoro-1-hexene (CH2=CHCH2CF2C2 F5), 1,1,1,2,2,3,4-heptafluoro-3-hexene (CF3CF2CF=CFC2H5), 4,5,5,5-tetrafluoro-4-(trifluoromethyl)-1-pentene (CH2=CHCH2CF(CF3)2), 1,1,1,2,5,5,5-heptafluoro-4-methyl-2-pentene (CF3CF=CHCH(CF3)(CH3)), 1,1,1,3-tetrafluoro-2-(trifluoromethyl)-2-pentene ((CF3)2C=CFC2H5), 1,1,1,2,3,4,4,5,5,6,6,7,7,7-Tetradecafluoro-2-heptene (CF3CF=CFCF2CF2C2F5), 1,1,1,2,2,3,4,5,5,6,6,7,7,7-Tetradecafluoro-3-heptene (CF3CF2CF=CFCF2C2F5), 1,1,1,3,4,4,5,5,6,6,7,7,7-tridecafluoro-2-heptene (CF3CH=CFCF2CF2C2F5), 1,1,1,2,4,4,5,5,6,6,7,7,7-tridecafluoro-2- A process using an embodiment in which heat is exchanged using heptene (CFCF=CHCFCFCF), 1,1,1,2,2,4,5,5,6,6,7,7,7-tridecafluoro-3-heptene (CFCFCH=CFCFCF), 1,1,1,2,2,3,5,5,6,6,7,7,7-tridecafluoro-3-heptene (CFCFCF=CHCFCF), alone or in admixture with other HFOs, HCFOs, and HFC compounds.

[0115] 1,1,1,2,3,4,4,5,5,5-Decafluoropentane (Vertrel XF), MPHE (Opteon™ SF10), 94% trans-1,2-dichloroethylene, 5% MPHE, and 1% Vertrel XF (a blend containing 1,1,1,2,3,4,4,5,5,5-decafluoropentane (Opteon™ SF79), a blend containing 94% trans-1,2-dichloroethylene, 5% MPHE, and 1% Z-1336mzz (Opteon™ SF80), a blend containing 98.4% Z-1336mzz and 1.6% ethanol (Opteon™ SF01), a blend containing 60% Z-1336mzz, 25% MPHE, and 15% ethanol (Opteon™ SF05), a blend containing 75% Z-1336mzz and 25% trans-1,2-dichloroethylene (Opteon™ SF06), a blend containing 1,1,1,2,3,4,4,5,5,5-decafluoropentane (Opteon™ SF79), a blend containing 94% trans-1,2-dichloroethylene, 5% MPHE, and 1% Z-1336mzz (Opteon™ SF80), a blend containing 98.4% Z-1336mzz and 1.6% ethanol (Opteon™ SF01), a blend containing 60% Z-1336mzz, 25% MPHE, and 15% ethanol (Opteon™ SF06), a blend containing 75% Z-1336mzz and 25% trans-1,2-dichloroethylene (Opteon™ SF06), a blend containing 1,1,1,2,3,4,4,5,5,5-decafluoropentane (Opteon™ SF79), a blend containing 1,1,1,2,3,4,4,5,5,5-decafluoropentane (Opteon™ SF80), a blend containing 1,1,1,2,3,4,4,5,5,5-decafluoropentane (Opteon™ 10. A process using an embodiment in which heat is exchanged using a regenerated fluid selected from a blend containing ethylene (Opteon™ SF30), (Z)-1,1,1,4,4,4-hexafluoro-2-butene (Opteon™ SF33), 1,1,1,2,2,3,3,6,6,7,7,8,8,8-tetradecafluoro-4-octene (F33E), 1,1,1,2,2,5,5,6,6,6-decafluorohex-3-ene (F22E), and 1,1,1,2,2,3,3,4,4,7,7,8,8,9,9,10,10,10-octadecafluorodec-5-ene (F44E).

[0116] A process using an embodiment in which recycled fluoroketone (FK) or hydrofluoroketone (HF) is used to exchange heat.

[0117] and a process using an embodiment in which the reclaimed halogenated liquid selected from one of hydrofluoroolefins (HFOs), hydrochlorofluoroolefins (HCFOs), hydrofluoroethers (HFEs), and hydrofluoroolefin ethers (HFOEs) is used as a heat exchanging aerosol propellant, a refrigerant, a cleaning agent, a blowing agent for thermoplastic and thermoset foams, a heat transfer medium, a liquid dielectric, a power cycle working fluid, a polymerization medium, a particle removal fluid, a carrier fluid, a buffing abrasive, and a displacement drying agent.

[0118] A heat exchange embodiment comprising: charging a working fluid selected from at least one of recycled hydrofluoroolefins (HFOs), hydrochlorofluoroolefins (HCFOs), hydrofluoroethers (HFEs), and hydrofluoroolefin ethers (HFOEs) to a system; and circulating the working fluid.

[0119] A cooling embodiment, wherein cooling comprises directly contacting the electrical component with at least one recycled hydrofluoroolefin (HFO), hydrochlorofluoroolefin (HCFO), hydrofluoroether (HFE), hydrofluoroolefin ether (HFOE).

[0120] A heat exchange embodiment comprising: introducing a working fluid selected from at least one of a regenerated fluoroketone (FK) or a hydrofluoroketone (HFK) into a system; and circulating the working fluid.

[0121] A cooling embodiment, wherein cooling comprises directly contacting the electrical component with at least one of a recycled fluoroketone (FK) or a hydrofluoroketone (HFK).

[0122] Process embodiments comprising using at least one recycled hydrofluoroolefin (HFO), hydrochlorofluoroolefin (HCFO), hydrofluoroether (HFE), hydrofluoroolefin ether (HFOE) in refrigeration, in air conditioning, in heating, in heat transfer, in converting heat to mechanical work in power cycles, as a foam blowing agent, as a solvent, or in preventing or quenching electrical discharge.

[0123] Process embodiments comprising using at least one recycled hydrofluoroolefin (HFO), hydrochlorofluoroolefin (HCFO), hydrofluoroether (HFE), hydrofluoroolefin ether (HFOE), hydrofluoroketone (HFK) with a refrigerant component, an air conditioning component, a heating component, a heat transfer component, a working fluid component, a blowing agent component, a solvent component, or a dielectric component.

[0124] Process embodiments comprising using at least one recycled fluoroketone (FK) or hydrofluoroketone (HFK) in refrigeration, in air conditioning, in heating, in heat transfer, in converting heat to mechanical work in power cycles, as a foam blowing agent, as a solvent, or in preventing or quenching electrical discharges.

[0125] Process embodiments including at least one recycled fluoroketone (FK) or hydrofluoroketone (HFK) with a refrigerant component, an air conditioning component, a heating component, a heat transfer component, a working fluid component, a blowing agent component, a solvent component, or a dielectric component.

[0126] A composition embodiment comprising one or more regenerated compounds, wherein the regenerated compound is one of the compounds listed in Table 1, and optionally contains a tracer.

[0127] A composition embodiment comprising one or more regenerated compounds, wherein the regenerated compound is one of the compounds listed in Table 2, and optionally contains a tracer.

[0128] A composition embodiment comprising one or more regenerated compounds, wherein the regenerated compound is one of the compounds listed in Table 3, and optionally contains a tracer.

[0129] A composition embodiment comprising one or more regenerated compounds, wherein the regenerated compound is one of the compounds listed in Table 4, and optionally contains a tracer.

[0130] In some embodiments, for any of the composition and process embodiments disclosed herein, HFO-E / Z-1336mzz includes HFO-E 1336mzz, HFO-Z 1336mzz, and a mixture of HFO-E 1336mzz and HFO-Z 1336mzz; HFO-E / Z-1224yd includes HFO-E 1336mzz, HFO-Z 1224yd, and a mixture of HFO-E 1224yd and HFO-Z 1224yd; and HCFO-E / Z-1233zd includes HCFO-E-1233zd, HCFO-Z-1233zd, and a mixture of HCFO-E-1233zd and HCFO-Z-1233zd.

[0131] While certain aspects, embodiments, and principles have been described above, it is understood that this description is made by way of example only and does not limit the scope of the invention or the appended claims. The various aspects, embodiments, and principles described above can be used alone and in combination with each other.

Claims

1. A process comprising: a) treating foam waste or spent halogenated liquid to produce a reclaimed foam polymer or a reclaimed halogenated liquid, wherein the foam waste and / or spent halogenated liquid is selected from the group consisting of a refrigerant, a refrigerant blend, a blowing agent, a solvent, and an immersion coolant; b) collecting or packaging the recycled foam polymer or recycled halogenated liquid; The process includes:

2. 10. The process of claim 1, wherein the spent halogenated liquid is treated to comprise at least one of hydrochloroolefins (HCO), hydrofluoroolefins (HFO), hydrochlorofluoroolefins (HCFO), hydrofluoroethers (HFE), hydrofluoroolefin ethers (HFOE), chlorofluoroolefins (CFO), fluoroketones, or hydrofluoroketones (HFK).

3. 10. The process of claim 1, wherein the foam waste is treated by crushing.

4. 4. The process of any one of claims 1 to 3, wherein the foam waste and / or used halogenated liquid is collected from unregenerated foam waste or unregenerated halogenated liquid prior to a).

5. 5. The process of claim 4, wherein the unregenerated halogenated liquid is analyzed prior to a) to determine the composition of the unregenerated halogenated liquid and the presence and nature of any contaminants.

6. 5. The process of claim 4, wherein the physical and chemical properties of the unregenerated halogenated liquid are determined prior to a).

7. 6. The process of claim 5, wherein said treating said foam waste and / or spent halogenated liquid comprises physical and chemical treatment.

8. 6. The process of claim 5, wherein said treating said foam waste and / or spent halogenated liquid comprises at least one of water removal, contaminant removal, and distillation.

9. A process comprising: a) identifying an unregenerated halogenated liquid selected from the group consisting of hydrochloroolefins (HCO), hydrofluoroolefins (HFO), hydrochlorofluoroolefins (HCFO), hydrofluoroethers (HFE), hydrofluoroolefin ethers (HFOE), hydrofluoroketones (HFK), and mixtures of two or more; b) optionally identifying contaminants in the unregenerated halogenated liquid of step a); c) selecting a physical and / or chemical treatment based on step a) and optionally step b); c) treating the unregenerated halogenated liquid of steps a) and b) using the physical and / or chemical treatment selected in step c) to produce an at least partially regenerated halogenated liquid; d) comparing the purity of the at least partially regenerated halogenated liquid of step c) with industry standards; e) optionally further processing the partially unregenerated halogenated liquid of step c) to produce a fully regenerated halogenated liquid; f) optionally comparing the purity of the at least partially regenerated halogenated liquid of step e) with an industry standard; g) optionally, compositionally re-equilibrating the partially or fully regenerated halogenated liquid to an industrially compatible product; h) collecting or packaging the product of step g).

10. 10. The process of claim 1, wherein the foam waste comprises halogenated hydrocarbon-generating foam that is crushed under vacuum to produce crushed foam and a vapor stream.

11. The process of claim 10 wherein the vapor stream is removed from the fractured foam.

12. 12. The process of claim 11, wherein the crushed foam is isolated and pelletized.

13. 10. The process of any one of claims 1 to 9, wherein the halogenated liquid is selected from the group consisting of E 1,2-dichloroethene, HFO-E / Z-1336mzz, HCFO-E / Z-1224yd, HCFO-E / Z-1233zd, R-514A (HCO+HFO) olefin blend composed of cis-1,1,1,4,4,4-hexafluorobut-2-ene and (R-1336mzz(Z)) and trans-1,2-dichloroethene (R-1130(E)), HFO-Z / E 1336mzz blend, liquid HFC-245fa, and 1,1,1,2,3,4,4,5,5,5-decafluoropentane.

14. The halogenated liquid may be a blend comprising 1,1,1,2,3,4,4,5,5,5-decafluoropentane, MPHE, 94% trans-1,2-dichloroethylene, 5% MPHE, and 1% 1,1,1,2,3,4,4,5,5,5-decafluoropentane, a blend comprising 94% trans-1,2-dichloroethylene, 5% MPHE, and 1% Z-1336mzz, a blend comprising 98.4% Z-1336mzz and 1.6% ethanol, a blend comprising 60% Z-1336mzz, 25% MPHE, and 15% ethanol, a blend comprising 75% Z-1336mzz and 25% trans 10. The process of any one of claims 1 to 9, wherein the blend comprises a liquid selected from the group consisting of 1,2-dichloroethylene, (Z)-1,1,1,4,4,4-hexafluoro-2-butene, 1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)pent-2-ene, 1,1,1,2,2,3,3,6,6,7,7,8,8,8-tetradecafluoro-4-octene, 1,1,1,2,2,5,5,6,6,6-decafluorohex-3-ene, and 1,1,1,2,2,3,3,4,4,7,7,8,8,9,9,10,10,10-octadecafluorodec-5-ene.

15. 10. The process of any one of claims 1 to 9, wherein the halogenated liquid comprises one of a hydrofluoroether (HFE) and a hydrofluoroolefin ether (HFOE).

16. The hydrofluoroether (HFE) may be methoxy-nonafluorobutane, ethoxy-nonafluorobutane, 1,1,1,2,2,3,4,5,5,5-decafluoro-3-methoxy-4-(trifluoromethyl)pentane, 3-ethoxy-1,1,1,2,3,4,4,5,5,6,6,6-dodecafluoro-2-(trifluoromethyl)hexane, a blend containing 50% methyl nonafluorobutyl ether and 50% trans-1,2-dichloroethylene, a blend containing 52.7% methyl nonafluorobutyl ether, 44.6% trans-1,2-dichloroethylene, and 2.7% ethanol, 10% methyl nonafluorobutyl ether, 16. The process of claim 15, comprising a liquid selected from the group consisting of a blend comprising 20% ​​ethyl nonafluorobutyl ether, 68% trans-1,2-dichloroethylene, and 2% isopropanol, a blend comprising 10% methyl nonafluorobutyl ether, 20% ethyl nonafluorobutyl ether, and 70% trans-1,2-dichloroethylene, a blend comprising 95.5% methyl nonafluorobutyl ether and 4.5% isopropanol, and / or a blend comprising 1,1,1,2,2,3,4,5,5,5-decafluoro-3-methoxy-4-(trifluoromethyl)pentane and trans-1,2-dichloroethylene.

17. 17. The process of any one of claims 1 to 9 and 13 to 16, wherein a tracer is added to at least one of the partially regenerated or fully regenerated halogenated liquid.

18. 17. The process of any one of claims 1-9 and 13-16, wherein a stabilizer package is added to at least one of the partially regenerated or fully regenerated halogenated liquids and comprises at least one antioxidant, at least one acid acceptor, and at least one metal stabilizer, wherein the antioxidant is selected from the group consisting of butylated hydroxytoluene, butylated hydroxyanisole, tert-butylhydroquinone, 4-methoxyphenol, propyl 3,4,5-trihydroxybenzoate, the acid acceptor is selected from epoxybutane, amines, and acetaldehyde di-methylhydrazone (ADH), and the metal stabilizer is selected from N,N'-bis(salicylidene)-1,2-propanediamine, benzotriazole, and derivatives thereof.

19. 17. The process of any one of claims 1-9 and 13-16, wherein one of the spent and unregenerated halogenated liquid comprises a blend of HFO-E / Z-1336mzz and HFO-Z / E 1336mzz.

20. 17. The process of any one of claims 1-9 and 13-16, wherein one of the spent and unregenerated halogenated liquid comprises HCFO-E / Z-1224yd.

21. 17. The process of any one of claims 1-9 and 13-16, wherein one of the spent and unregenerated halogenated liquid comprises HCFO-E / Z-1233zd.

22. 17. The process of any one of claims 1 to 9 and 13 to 16, wherein one of the spent and unregenerated halogenated liquids comprises cis-1,1,1,4,4,4-hexafluorobut-2-ene (R-1336mzz(Z)) and trans-1,2-dichloroethene (R-1130(E)).

23. 6. The process of claim 5, wherein the unregenerated halogenated liquid is analyzed using at least one analytical technique selected from the group consisting of GC-FID, GC-TCD, GC-MS, FTIR, Goetz Bub, Karl Fischer, Byk-Garner Color, and the contaminants include one or more of acidity, moisture, and NAG.

24. 10. The process of claim 9, wherein the testing of step b) comprises GC-MS or FTIR, the testing being for acidity, moisture, and NAG content.

25. 25. The process of claim 24, wherein the NAG testing involves using one of an infrared sensor, a UV sensor, a NIR sensor, an ion mobility or plasma chromatography, a gas chromatography, a refractive index measurement, a mass spectrometry, a high temperature thick film sensor, a thin film field effect sensor, a pellistor sensor, a Taguchi sensor, and a quartz crystal microbalance sensor.

26. 10. The process of claim 1 or 9, wherein the treating comprises at least one treatment selected from the group consisting of distillation, adsorption, desorption, cryogenic cooling, water removal by distillation and / or desiccant drying, solids filtration, acidity neutralization, and high boiling residue / chloride distillation.

27. 14. The partially or fully regenerated composition of claim 13.

28. 15. The partially or fully regenerated composition of claim 14.

29. 16. The partially or fully regenerated composition of claim 15.

30. 17. The partially or fully regenerated composition of claim 16.

31. An integrated system, - a non-recycled liquid collection station; - a waste foam collection station; - A weighing and testing station for HFO-E / Z-1336mzz, HCFO-1224yd, HCFO-1233zd, R-514A (an olefin blend composed of cis-1,1,1,4,4,4-hexafluorobut-2-ene (R-1336mzz(Z)) and trans-1,2-dichloroethene (R-1130(E))), HFO-Z / E A blend containing 94% trans-1,2-dichloroethylene, 5% MPHE, and 1% 1,1,1,2,3,4,4,5,5,5-decafluoropentane, a blend containing 94% trans-1,2-dichloroethylene, 5% MPHE, and 1% Z-1336mzz, a blend containing 98.4% Z-1336mzz and 1.6% ethanol, a blend containing 60% Z-1336mzz, 25% MPHE, and 15% ethanol, a blend containing 75% Z-1336mzz and 25% trans-1,2- a weighing and testing station comprising an analytical system for determining physical and chemical properties of said unregenerated liquid selected from the group consisting of a blend comprising dichloroethylene, (Z)-1,1,1,4,4,4-hexafluoro-2-butene, 1,1,1,4,5,5,5-heptafluoro-4-(trifluoromethyl)pent-2-ene, 1,1,1,2,2,3,3,6,6,7,7,8,8,8-tetradecafluoro-4-octene, 1,1,1,2,2,5,5,6,6,6-decafluorohex-3-ene, and 1,1,1,2,2,3,3,4,4,7,7,8,8,9,9,10,10,10-octadecafluorodec-5-ene; a waste foam processing station comprising at least one crusher, at least one solids separator, at least one pelletizer with steam separation; a first purification system for receiving and treating the unregenerated liquid from the weighing and testing station, the waste foam treatment station and the vapor from the first transport line; a second purification system for receiving and processing liquid from said first purification system and the second transfer line; a target refrigerant system including a blending station in fluid communication with first and second transfer lines for receiving treated liquid from the first and second purification systems to adjust the levels of regenerated liquid constituents to target refrigerant levels of the AHRI 700 standard following purification at said first and second purification stations, and for providing regenerated liquid blend constituents consistent with the AHRI 700 standard; a stabilizer package dispensing station for adding an effective amount of a stabilizer package comprising at least one antioxidant, at least one acid acceptor, and at least one metal stabilizer; a purity verification station for verifying the purity of the unregenerated liquid before purification, the purity after the first and / or second purification treatment, and the purity of at least one first treated product, and for determining whether said first treated product meets or exceeds the AHRI 700 standard; An integrated system comprising one or more of:

32. 32. The system of claim 31 , wherein the weighing and testing station includes a scale and at least one of a GC-FID, a GC-TCD, a GC-MS, an FTIR, a Goetz Bub, a Karl Fischer, and a Byk-Garner Color detector.

33. 32. The system of claim 31 , wherein the weighing and testing station includes one of an infrared sensor, a UV sensor, a NIR sensor, an ion mobility or plasma chromatography, a gas chromatography, a refractive index measurement, a mass spectrometry, a high temperature thick film sensor, a thin film field effect sensor, a pellistor sensor, a Taguchi sensor, and a quartz crystal microbalance sensor.

34. 32. The system of claim 31, wherein the weighing and testing station includes a scale, a GC-MS, and a Taguchi sensor.

35. 32. The system of claim 31, wherein at least one of the first and second purification systems includes one of a distillation column, an adsorption / desorption column, and a cryogenic refrigerator.

36. 32. The system of claim 31 , wherein at least one of the first and second purification systems includes at least one of an NCG purge unit, a water distillation or desiccant dryer unit, a solids filter unit, and an acidity neutralizer, and a high distillation bottoms column.

37. 31. A process for exchanging heat, comprising circulating the regenerated halogenated liquid of any one of claims 1 to 30 and transferring heat to and from the regenerated halogenated liquid.

38. 31. A process for using the regenerated halogenated liquid of any one of claims 1 to 30 as a heat exchanging aerosol propellant, a refrigerant, a cleaning agent, an expansion agent for thermoplastic and thermoset foams, a heat transfer medium, a liquid dielectric, a power cycle working fluid, a polymerization medium, a particle removal fluid, a carrier fluid, a buffing abrasive, and a displacement drying agent.

39. 1. A process for exchanging heat, comprising: introducing a working fluid selected from at least one of recycled hydrofluoroolefins (HFOs), hydrochlorofluoroolefins (HCFOs), hydrofluoroethers (HFEs), and hydrofluoroolefin ethers (HFOEs) into a system; and circulating the working fluid.

40. 1. A process for cooling an electrical component, comprising directly contacting the component with at least one of recycled hydrofluoroolefins (HFOs), hydrochlorofluoroolefins (HCFOs), hydrochloroolefins (HCOs), hydrofluoroethers (HFEs), and hydrofluoroolefin ethers (HFOEs).

41. 31. A process comprising using the regenerated halogenated composition of any one of claims 1 to 30 in refrigeration, in air conditioning, in heating, in heat transfer, in converting heat to mechanical work in a power cycle, as a foam blowing agent, as a solvent, or in preventing or quenching electrical discharge.

42. 31. A process comprising using the regenerated halogenated composition of any one of claims 1 to 30 with a refrigerant component, an air conditioning component, a heating component, a heat transfer component, a working fluid component, a blowing agent component, a solvent component, or a dielectric component.

43. 13. The process of any one of claims 1, 10, 11, and 12, wherein the foam waste is polyurethane foam that is crushed, pelletized, and converted into a chemically reduced liquid polyol.

44. 32. The system of claim 31, wherein the waste foam processing station is adapted to crush and pelletize polyurethane foam for one of subsequent use or recycling into liquid polyol.

45. At least one of a vessel and a tank filled with the regenerated composition of any one of claims 17 or 27-30.

46. The process of any one of claims 1 to 9, wherein the halogenated liquid comprises one or more of a fluoroketone (FK) and / or a hydrofluoroketone (HFK).

47. The process of any one of claims 1 to 9, wherein the halogenated liquid comprises one or more fluoroketones.

48. 48. The process of claim 47, wherein the fluoroketone comprises dodecafluoro-2-methylpentan-3-one.

49. 1. A composition comprising at least one regenerated compound, wherein the at least one regenerated compound is selected from one of Table 1, Table 2, Table 3, or Table 4, and comprises one or more tracers.

50. 50. The composition of claim 49, wherein the at least one regenerated compound is selected from Table 2.

51. 50. The composition of claim 49, wherein the at least one regenerated compound is selected from Table 1.

52. 50. The composition of claim 49, wherein the at least one regenerated compound is selected from Table 3.

53. 50. The composition of claim 49, wherein the at least one regenerated compound is selected from Table 4.

54. 1. A system comprising: a contained supply of regenerated / reblended refrigerant; a refrigerant circuit including at least an input valve and a compressor; and a controllable transfer line connecting the contained supply of regenerated / reblended refrigerant to the input valve.

55. 1. A system comprising: a purification system; a contained supply of regenerated / reblended refrigerant connected to the system; a refrigerant circuit including at least an input valve and a compressor; and a controllable transfer line connecting the contained supply of regenerated / reblended refrigerant to the input valve.

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