Preparation of high purity e-1,2-difluoroethylene

Abstract

A process includes providing a composition including E-1,2-difluoroethylene (HFO-E-1132), and Z-1,2-difluoroethylene (HFO-Z-1132), and separating the HFO-Z-1132 from the HFO-E-1132 by a separation process selected from extractive distillation of the composition, chemical absorption of the HFO-Z-1132 in the composition, and chemical reaction of the HFO-Z-1132 in the composition to provide a purified composition comprising the HFO-E-1132 and being free of or substantially free of HFO-Z-1132. In another aspect, the process includes distilling the HFO-E / Z-1132 composition to provide a first fraction including HFO-E-1132 and free of or substantially free of HFO-Z-1132 and a second fraction including a major amount of HFO-Z-1132 and a minor amount of HFO-E-1132, collecting the first fraction as a purified composition, converting the second fraction to 1,1,2-trifluoroethane, 1,2-dibromo-1,2-difluoroethane or 1,2-dichloro-1,2-difluoroethane, converting the 1,1,2-trifluoroethane, 1,2-dibromo-1,2-difluoroethane or 1,2-dichloro-1,2-difluoroethane to HFO-E / Z-1132, and recycling the HFO-E / Z-1132 for distillation.

Description

TS0073-W001TITLE OF THE INVENTIONPREPARATION OF HIGH PURITY E-1 ,2-DIFLUOROETHYLENECROSS REFERENCE TO RELATED APPLICATIONS

[0001] This application claims priority to U.S. Provisional Application No. 63 / 698,134, filed on September 24, 2024, the disclosure of which is herein incorporated by reference in its entirety.FIELD

[0002] The present disclosure relates to processes of olefin purification and purified compositions thereof. More specifically, the present disclosure relates to processes of E-1 ,2-difluoroethylene (E-CHF=CHF; HFO-E-1132) purification and purified compositions of HFO-E-1132.BACKGROUND

[0003] The fluorocarbon industry has been working for the past few decades to find replacement refrigerants for the ozone depleting chlorofluorocarbons (CFCs) and hydrochlorofluorocarbons (HCFCs) being phased out as a result of the Montreal Protocol. The solution for many applications has been the commercialization of hydrofluorocarbon (HFC) compounds for use as refrigerants, solvents, fire extinguishing agents, blowing agents and propellants. HFC refrigerants, such as HFC- 125 (C2HF5) and HFC- 134a (CH2FCF3), have zero ozone depletion potential (ODP) and thus are not affected by the regulatory phase-out as a result of the Montreal Protocol. In addition to ozone depleting concerns, however, global warming is another environmental concern in many of these applications. HFC refrigerants such as HFC-134a and HFC-125 respectively have global warming potentials (GWP) of 1 ,300 and 3,170 according to the UN's IPCC Fifth Assessment Report (AR5). Hydrofluoroolefins (HFOs) having low ODP and low GWP have been replacing saturated CFCs, HCFCs, and HFCs in a variety of applications for several years because saturated hydrohalocarbons tend to have high GWP values.

[0004] This regulatory landscape is continuously evolving, taking into consideration properties beyond just ODP and GWP. More particularly, there is aTS0073-W001 need for refrigerant compositions that not only meet low ODP standards and have low global warming potentials, but that also exhibit low or no flammability, provide superior performance in a variety of applications and which meet the standards of evolving regulations.

[0005] There is a need in this art for new refrigerants that meet evolving regulations as well as provide heat transfer and refrigerant characteristics that meet or exceed the effectiveness of conventional refrigerants.

[0006] Some fluoroethylenes, particularly difluoroethylenes, and more particularly the E-isomer of 1,2-difluoroethylene (HFO-E-1132, E-CHF=CHF), which has a boiling point of -52°C, is one such potential new refrigerant.

[0007] Conventional processes of making HFO-E-1132 make both the E-isomer and the Z-isomer (Z-1 ,2-difluoroethylene; Z-CHF=CHF; HFO-Z-1132). Indeed, current processing generally favors the production of the Z-isomer, which requires significant amounts to be isomerized to the E-isomer, which is more desirable as a refrigerant or refrigerant blend component.

[0008] Thus, there is a need for efficient and effective processes to produce H FOE-1132 that is free of or substantially free of HFO-Z-1132, which would further benefit both the environment and the global economy.SUMMARY

[0009] In an example embodiment, a process comprises providing a composition comprising E-1 ,2-difluoroethylene (HFO-E-1132) and Z-1,2-difluoroethylene (HFO-Z- 1132); and separating the HFO-Z-1132 from the HFO-E-1132 by a separation process selected from extractive distillation of the composition, chemical absorption of the HFO-Z-1132 in the composition, and chemical reaction of the HFO-Z-1132 in the composition to provide a purified composition comprising the HFO-E-1132.

[0010] In another example embodiment, a process comprises distilling a composition comprising E-1 ,2-difluoroethylene (HFO-E-1132) and Z-1 ,2- difluoroethylene (HFO-Z-1132) to provide at least one first fraction and at least one second fraction, the at least one first fraction comprising HFO-E-1132 and being free of or substantially free of HFO-Z-1132 and the at least one second fractionTS0073-W001 comprising a major amount of HFO-Z-1132 and a minor amount of HFO-E-1132; collecting the at least one first fraction as a purified composition; converting the at least one second fraction to 1,1,2-trifluoroethane (HFC-143), 1 ,2-dibromo-1,2- difluoroethane (HBFC-132B2) or 1 ,2-dichloro-1,2-difluoroethane (HCFC-132); converting the HFC-143, HBFC-132B2 or HCFC-132 to a HFO-E / Z-1132 mixture comprising a major amount of HFO-E-1132 and a minor amount of HFO-Z-1132; and recycling the HFO-E / Z-1132 mixture for distillation.

[0011] In yet another example embodiment, a purified composition formed by any of the processes disclosed herein includes HFO-E-1132 and is free of or substantially free of HFO-Z-1132.

[0012] Other features and advantages of the present disclosure will be apparent from the following more detailed description.DETAILED DESCRIPTION

[0013] One aspect of the present invention relates to a process comprising separating Z-1,2-difluoroethylene (HFO-Z-1132) from E-1 ,2-difluoroethylene (HFO- E-1132). One aspect of the present invention relates to a process comprising separating or removing HFO-Z-1132 from a composition comprising HFO-E-1132. In some embodiments, the removal or separating process includes an extractive distillation. In some embodiments, the removal or separating process includes a chemical absorption. In some embodiments, the removal or separating process includes distillation in combination with one or more chemical reactions which produce a product composition comprising primarily HFO-E-1132. The resulting composition of any of the processes of the present invention is free of or substantially free of the HFO-Z-1132.

[0014] As used herein, the term “extractive distillation” refers to a distillation of a composition in which a miscible high-boiling solvent that is not azeotropic with other components of the distillation has been added to separate components that would otherwise not separate by distillation as being azeotropic, azeotrope-like, or closeboiling.

[0015] As used herein, the term "azeotrope-like” refers to a composition of two or more compounds that behaves like an azeotropic composition (i.e. , has constantTS0073-W001 boiling characteristics or a tendency not to fractionate upon boiling or evaporation). Hence, during boiling or evaporation, the vapor and liquid compositions, if they change at all, change only to a minimal or negligible extent. In contrast, the vapor and liquid compositions of non-azeotrope-like compositions change to a substantial degree during boiling or evaporation.

[0016] As used herein, the term "azeotrope-like behavior" refers to a behavior exhibiting dew point pressure and bubble point pressure with virtually no pressure differential. In some embodiments, the difference in the dew point pressure and bubble point pressure at a given temperature is 10% or less, alternatively 9% or less, alternatively 8% or less, alternatively 7% or less, alternatively 6% or less, alternatively 5% or less, alternatively 4% or less, alternatively 3% or less, alternatively 2% or less, alternatively 1% or less, or any value, range, or sub-range therebetween.

[0017] As used herein, the term “close-boiling” refers to compositions including at least two compounds having a boiling point difference within about 20°C, or within about 18°C, or within about 15°C, or within about 12°C, or within about 10°C. In some embodiments, the boiling point difference is less than about 9°C, alternatively less than about 8°C, alternatively less than about 7°C, alternatively less than about 6°C, alternatively less than about 5°C, alternatively less than about 4°C, alternatively less than about 3°C, alternatively less than about 2°C, or any value, range, or subrange therebetween.

[0018] As used herein, the term “scrubbing” is meant to include any process wherein a mixture of species is contacted with a media in which one or more components of the mixture are selectively removed from or reduced in amount in the mixture via chemical reaction or dissolution.

[0019] As used herein, the terms “comprises,” “comprising,” “includes,” “including,” “has,” “having”, or any other variation thereof, are intended to cover a non-exclusive inclusion. For example, a composition, process, method, article, or apparatus that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, process, method, article, or apparatus. Further, unless expressly stated to the contrary, “or” refers to an inclusive or and not to 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 notTS0073-W001 present), A is false (or not present) and B is true (or present), and both A and B are true (or present).

[0020] The transitional phrase “consisting of” excludes any element, step, or ingredient not specified. If in the claim such would close the claim to the inclusion of materials other than those recited except for impurities ordinarily associated therewith. When the phrase “consists of’ appears in a clause of the body of a claim, rather than immediately following the preamble, it limits only the element set forth in that clause; other elements are not excluded from the claim as a whole.

[0021] The transitional phrase “consisting essentially of’ is used to define a composition, method that includes materials, steps, features, components, or elements, in addition to those literally disclosed provided that these additional included materials, steps, features, components, or elements do not materially affect the basic and novel characteristic(s) of the claimed invention, especially the mode of action to achieve the desired result of any of the processes of the present invention. The term “consisting essentially of” occupies a middle ground between “comprising” and “consisting of”.

[0022] Where applicants have defined an invention or a portion thereof with an open-ended term such as “comprising”, it should be readily understood that (unless otherwise stated) the description should be interpreted to also include such an invention using the terms “consisting essentially of’ or “consisting of”.

[0023] Also, use of “a” or “an” are employed 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 read to include one or at least one and the singular also includes the plural unless it is obvious that it is meant otherwise.

[0024] Where a range of numerical values is recited herein, unless otherwise stated, the range is intended to include the endpoints thereof, and all integers and fractions within the range. It is not intended that the scope of the disclosure be limited to the specific values recited when defining a range. Moreover, all ranges set forth herein are intended to include not only the particular ranges specifically described, but also any combination of values therein, including the minimum and maximum values recited.TS0073-W001

[0025] When an amount, concentration, or other value or parameter is given as either a range, preferred range, or a list of upper preferable values and / or lower preferable values, this is to be understood as specifically disclosing all ranges formed from any pair of any upper range limit or preferred value and any lower range limit or preferred value, regardless of whether ranges are separately disclosed. Where a range of numerical values is recited herein, unless otherwise stated, the range is intended to include the endpoints thereof, and all integers and fractions within the range.

[0026] As used herein, the term “substantially free” means that less than about 0.5 percent by weight (wt%) or 5000 ppm is present, or less than about 0.4 wt% or 4000 ppm is present, or less than about 0.3 wt% or 3000 ppm is present, or less than about 0.2 wt% or 2000 ppm is present, or less than about 0.1 wt% or 1000 ppm is present, or preferably less than about 0.01 wt% or 100 ppm is present, more preferably less than about 0.001 wt% or 10 ppm is present, and most preferably less than about 0.0001 wt% or 1 ppm is present.

[0027] As used herein the term “about” in certain embodiments can be quantified to mean ± 1%, ± 2%, ± 3% and up to and including ±10% of the stated value, and all whole numbers and fractions therebetween.TABLE OF COMPOUNDS

[0028] By way of example, mention is made of the following compounds:TS0073-W001

[0029] Some of the compounds present in the compositions of the present disclosure identified in the Table of Compounds may exist as different configurational isomers or stereoisomers. The present disclosure is intended to include all single configurational isomers, single stereoisomers, or any combination or mixture thereof, unless otherwise specified as the Z-isomer or the E-isomer. For instance, 1-chloro-TS0073-W0011 ,2-difluoroethylene (HFO-1122a) exists as a Z-isomer, an E-isomer, or any combination or mixture of both isomers in any ratio. Single isomers or multiple isomers of the same compound may be used in any proportion.

[0030] In some embodiments, the process of the present invention involves a composition or product stream that includes both HFO-E-1132 and HFO-Z-1132. The process also includes separating the HFO-Z-1132 from the HFO-E-1132 from this starting composition or product stream. The resulting composition comprises HFO-E-1132 and is free of or substantially free of HFO-Z-1132.

[0031] The starting composition may be any composition including both HFO-E- 1132 and HFO-Z-1132. For example, the starting composition may be a product mixture or part of a product mixture produced by a reaction or series of reactions, such as any reaction(s) known to produce HFO-1132, as described in further detail herein.

[0032] In some embodiments, suitable starting compositions may include a total combined amount of HFO-E-1132 and HFO-Z-1132 of at least 50% by weight of the starting composition, alternatively at least 60% by weight, alternatively at least 75% by weight, alternatively at least 90% by weight, alternatively at least 95% by weight, alternatively at least 98% by weight, alternatively at least 99% by weight, or any value, range, or sub-range therebetween.

[0033] In some embodiments, a suitable weight ratio of HFO-Z-1132 to HFO-E- 1132 (i.e., Z / E ratio) of the starting composition may be less than 10:1 , alternatively less than 5:1, alternatively less than 3:1, alternatively less than 2:1 , alternatively less than 1 :1 , alternatively at least 1 :5, alternatively at least 1 :3, alternatively at least 1:2, alternatively at least 1 :1, or any value, range, or sub-range therebetween.

[0034] The starting composition may have been formed by any appropriate forming process. In some embodiments, the starting composition may be or may have been formed by dechlorination of 1,2-dichloro-1,2-difluoroethane (HCFC-132). In some embodiments, the starting composition may be or may have been formed by dehydrofluorination of 1,1,2-trifluoroethane (HFC-143). In some embodiments, the starting composition may be or may have been formed by debromination of 1,2- dibromo-1,2-difluoroethane (HBFC-132B2, CHBrFCHBrF). In some embodiments,TS0073-W001 the appropriate forming process is selected to provide a high HFO-E / Z-1132 yield and a low Z / E ratio.

[0035] It will be understood by those skilled in the art that while specific processes for forming HFO-E / Z-1132 may be described herein, the invention is not limited to such processes. Rather, the starting composition may be produced by any known or yet to be developed forming process and then subjected to the inventive separation processes disclosed herein.

[0036] In some embodiments, the starting composition may comprise, consist of or consist essentially of HFO-E-1132, HFO-Z-1132 and one or more additional compounds selected from difluoromethane (HFC-32), 1,1, 1 ,2, 2 pentafluoroethane (HFC-125), E-1-chloro-1 ,2-difluoroethylene (HCFO-E-1122a), Z-1-chloro-1,2- difluoroethylene (HCFO-Z-1122a), 1,1,2-trifluoroethylene (HFO-1123), fluoroethylene (HFO-1141), 1-chloro-1,2,2-trifluoroethane (HCFC-133), 1-chloro-1 , 1 ,2- trifluoroethane (HCFC-133b), 1,1-dichloro-2,2,2-trifluoroethane (HCFC-123), 1 ,2- difluoroethane (HFC-152), 1,1 ,2-trifluoroethane (HFC-143), fluoromethane (HFC-41), chlorodifluoromethane (HCFC-22), ethylene, 1 -chloro- 1,2-difluoroethane (HCFC- 142a), 1 ,1 -difluoroethylene (HFO-1132a), 1-chloro-1-fluoroethene (HCFO-1131a), E- 1-chloro-2-fluoroethene (HCFO-E-1131), Z-1-chloro-1-fluoroethene (HCFO-Z-1131), 1-chloro-2,2-difluoroethylene (HCFO-1122), vinyl chloride (HCO-1140), acetylene and fluoroacetylene.

[0037] In one embodiment, the amount of additional compounds present in the starting composition can be greater than 0 and less than 1 wt% of the refrigerant composition, preferably less than 0.5 weight percent, or more preferably less than 0.1 weight percent, or any value, range, or sub-range therebetween. In some embodiments, the amount of additional compounds present can be greater than 0 ppm and less than 5,000 ppm and, in particular, can range from greater than zero to about 1,000 ppm, about 5 to about 500 ppm and about 1 to about 100 ppm, or any value, range, or sub-range therebetween. In one embodiment, the total amount of additional compounds is greater than zero and less than 1 weight percent based on the total weight of the composition, or any value, range, or sub-range therebetween. In one embodiment, the total amount of additional compounds is less than 1000 ppm, less than 500 ppm, less than 400 ppm, less than 300 ppm, less than 200 ppm,TS0073-W001 less than 100 ppm, less than 50 ppm, less than 10 ppm, less than 5 ppm, based on the total weight of the composition, or any value, range, or sub-range therebetween.

[0038] In some embodiments, the process of separating the E-isomer of HFO- 1132 from the Z-isomer includes an extractive distillation. The extractive distillation includes addition of a solvent to the composition including the HFO-Z-1132 and HFO-E-1132 to form a modified composition. More particularly, the extractive distillation comprises feeding the starting composition and a solvent to a first column, in which the starting composition and solvent are combined to form a modified composition which is then processed by the extractive distillation column to form separate fractions, one of which comprises HFO-E-1132 and one of which comprises HFO-Z-1132 and the solvent.

[0039] In some embodiments, the solvent has a higher boiling point than the HFO- Z-1132 and HFO-E-1132 of the starting composition and is miscible with the starting composition, and particularly the HFO-Z-1132 and HFO-E-1132, without forming an azeotrope.

[0040] HFO-Z-1132, having a dipole of about 2.93, is more polar than HFO-E- 1132, having a dipole of about zero. In some embodiments, the solvent is a polar solvent, such as, for example, a ketone, such as, for example, methyl isobutyl ketone (MIBK), methyl ethyl ketone (MEK), heptanone, pentanone, or cyclohexanone, or an ether, such as, for example, dimethylether or diethylether. In some embodiments, the solvent has an available empty lowest unoccupied molecular orbital (LIIMO). In some embodiments, the solvent is a carbonyl compound, such as, for example, a ketone, an aldehyde, or an ester, or a weak Lewis acid, such as, for example, a borate ester.

[0041] The modified composition is processed by the extractive distillation column to collect at least one fraction which comprises HFO-E-1132 and is free of or substantially free of HFO-Z-1132.

[0042] Further purification steps may be taken to remove or reduce the amount of additional compounds (e.g., compounds present in an amount of greater than about 0 and less than 1 wt.%) from the HFO-E-1132 fraction. For example, in some embodiments, the process further comprises a simple or fractional distillation of the HFO-E-1132 fraction after the extractive distillation in order to remove or reduce theTS0073-W001 amount of additional components from the composition. In some embodiments, the further distillation removes or reduces the amount of additional compounds from the composition comprising HFO-E-1132, such as, for example, HFO-Z-1132, acetylene, fluoroacetylene, HFC-152, HCO-1140, and / or HFO-1141. The treated and purified composition comprises HFO-E-1132 and is free of or substantially free of HFO-Z- 1132, acetylene, HFO-1141 and HFC-152.

[0043] In some embodiments, the process of separating the E-isomer of HFO- 1132 from the Z-isomer includes chemical absorption. In some embodiments, the chemical absorption includes contacting the composition comprising HFO-Z-1132 and HFO-E-1132 with a chemical absorbent that selectively reacts with the HFO-Z- 1132 over the HFO-E-1132 and produces a composition comprising HFO-E-1132 and which is free of or substantially free of HFO-Z-1132. Suitable chemical absorbents may include, but are not limited to, a low valent transition metalcontaining absorbent, such as, for example, absorbents containing one or more low valent transition metals selected from Or, Mn, Fe, Co, Ni, Cu, Mo, Ru, Rh, Pd, Ag, W, Re, Os, Ir, Pt, Zn and Au. In some embodiments, the chemical absorbent comprises one or more 3d metals. In some embodiments, the chemical absorbent comprises one or more 3d metals having electron donating ligands such as, but not limited to, phosphines (e.g., one or more of Ni(PRs)3, Ni(PRs)4, Pd (PRs)2, Fe(PRs)4, Fe(PRs)5, and / or Co(PR3)4, wherein R = alkyl or alkoxy, and wherein the ligands may be mono- or bidentate). The treated composition comprises HFO-E-1132 and is free of or substantially free of HFO-Z-1132.

[0044] Further purification steps may be taken to remove or reduce the amount of additional compounds from the HFO-E-1132 composition. For example, in some embodiments, the process further comprises a solvent scrubbing after the chemical absorption. In some embodiments, the solvent scrubbing includes treatment with a solvent selected from acetone, 2-butanone, 3-pentanone, methanol, ethanol, N,N- dimethylformamide, and N-methyl-pyrrolidinone. In some embodiments, the solvent scrubbing removes or reduces the amount of additional compounds from the composition, such as, for example, acetylene, fluoroacetylene, HFC-152, HCO-1140, and / or HFO-1141. The treated and purified composition comprises HFO-E-1132 and is free of or substantially free of HFO-Z-1132, acetylene, HFO-1141 and HFC-152.TS0073-W001

[0045] In some embodiments, the process of separating the E-isomer of HFO- 1132 from the Z-isomer includes a chemical reaction. In some embodiments, the chemical reaction includes contacting the composition comprising HFO-Z-1132 and HFO-E-1132 with a reagent that selectively reacts with the HFO-Z-1132 over the HFO-E-1132. Appropriate reagents may include, but are not limited to, a carbene that selectively reacts with HFO-Z-1132 such as via a Simmons-Smith reaction, or a diene that selectively reacts with HFO-Z-1132, including, but not limited to, cyclopentadiene, pentadiene, or 1,3-butadiene.

[0046] In some embodiments, the reaction converts the HFO-Z-1132 to a high boiling point compound that can easily be separated from the HFO-E-1132 by a simple or fractional distillation. Thus, the process produces at least one fraction or composition which comprises HFO-E-1132 and is free of or substantially free of HFO-Z-1132.

[0047] The simple or fractional distillation may also remove or reduce the amount of additional components from the composition, or a further simple or fractional distillation may be carried out to do so. In some embodiments, the distillation also removes or reduces the amount of additional compounds from the composition comprising HFO-E-1132, such as, for example, acetylene, fluoroacetylene, HFC- 152, HCO-1140, and / or HFO-1141. As such, in some embodiments, the process produces a treated and purified composition comprising HFO-E-1132 and which is free of or substantially free of HFO-Z-1132, acetylene, HFO-1141 and HFC-152.

[0048] In some embodiments, the process of separating the E-isomer of HFO- 1132 from the Z-isomer includes a simple or fractional distillation or an extractive distillation of the starting composition of HFO-E / Z-1132 to provide at least one first fraction and at least one second fraction. The first fraction comprises HFO-E-1132 and is free of or substantially free of HFO-Z-1132. For example, in one embodiment, the first fraction comprises greater than about 99 wt.% HFO-E-1132 and less than about 1 wt.% HFO-Z-1132. The second fraction comprises HFO-Z-1132 and small amounts of HFO-E-1132. For example, in one embodiment, the second fraction comprises greater than about 99 wt.% HFO-Z-1132 and less than about 1 wt.% HFO-E-1132.TS0073-W001

[0049] Thus, the process produces at least one fraction or composition which comprises HFO-E-1132 and is free of or substantially free of HFO-Z-1132. The process further comprises collecting the at least one first fraction as a purified composition of HFO-E-1132, and optionally further purifying the HFO-E-1132 composition (e.g., by additional distillation or solvent scrubbing as described above) to remove or reduce the amount of additional compounds present therein, such as but not limited to acetylene, fluoroacetylene, HFC-152, HCO-1140, and / or HFO- 1141. Thus, the process produces a treated and purified composition comprising HFO-E-1132 and which is free of or substantially free of HFO-Z-1132, acetylene, HFO-1141 and HFC-152.

[0050] In some embodiments, the process further comprises contacting the at least one second fraction (which comprises more HFO-Z-1132 than HFO-E-1132) with hydrogen fluoride (HF) under conditions to convert the HFO-Z-1132 and HFO-E- 1132 to HFC-143. The hydrofluorination of the HFO-E / Z-1132 mixture to produce HFC-143 is followed by dehydrofluorination of the HFC-143 under conditions to convert the HFC-143 to HFO-E / Z-1132. In some embodiments, the resulting HFO- E / Z-1132 has a high E / Z ratio (i.e., the dehydrofluorination of HFC-143 provides a mixture having more HFO-E-1132 than HFO-Z-1132). The resulting HFO-E / Z-1132 is then recycled to the simple or fractional distillation or extractive distillation. Thus, in this manner, the second fraction rich in HFO-Z-1132 can be processed to make additional amounts of HFO-E-1132.

[0051] In some embodiments, the process further comprises bromination of the at least one second fraction (which comprises more HFO-Z-1132 than HFO-E-1132) in the presence of Br2 and acetic acid under conditions to convert the HFO-Z-1132 and HFO-E-1132 to 1,2-dibromo-1,2-difluoroethane (HBFC-132B2, CHBrFCHBrF). The bromination of the HFO-E / Z-1132 mixture to produce HBFC-132B2 is followed by followed by debromination of the HBFC-132B2 in the presence of a metal powder, such as, for example, zinc or copper, under conditions to convert the HBFC-132B2 to HFO-E / Z-1132. In some embodiments, the resulting HFO-E / Z-1132 has a high E / Z ratio (i.e., the debromination of HBFC-132B2 provides a mixture having more HFO-E-1132 than HFO-Z-1132). The resulting HFO-E / Z-1132 is then recycled to the simple or fractional distillation or extractive distillation. Thus, in this manner, theTS0073-W001 second fraction rich in HFO-Z-1132 can be processed to make additional amounts of HFO-E-1132.

[0052] In some embodiments, the process further comprises chlorination of the at least one second fraction (which comprises more HFO-Z-1132 than HFO-E-1132) in the presence of CI2 with or without a catalyst under conditions to convert the HFO-Z- 1132 and HFO-E-1132 to 1,2-dichloro-1 ,2-difluoroethane (HCFC-132 CHCIFCHCIF). The chlorination of the HFO-E / Z-1132 mixture to produce HCFC-132 is followed by dechlorination of the HCFC-132 in the presence of a metal powder, such as, for example, magnesium, zinc or copper, under conditions to convert the HCFC-132 to HFO-E / Z-1132. In some embodiments, the resulting HFO-E / Z-1132 has a high E / Z ratio (i.e., the dechlorination of HCFC-132 provides a mixture having more HFO-E- 1132 than HFO-Z-1132). The resulting HFO-E / Z-1132 is then recycled to the simple or fractional distillation or extractive distillation. Thus, in this manner, the second fraction rich in HFO-Z-1132 can be processed to make additional amounts of HFO- E-1132.

[0053] In some embodiments, the composition formed by any of the processes disclosed herein comprises, consists of or consists essentially of HFO-E-1132.

[0054] In some embodiments, the composition formed by any of the processes disclosed herein comprises, consists of or consists essentially of HFO-E-1132 and is free of or substantially free of HFO-Z-1132.

[0055] In some embodiments, the composition formed by any of the processes disclosed herein comprises, consists of or consists essentially of HFO-E-1132 and is free of or substantially free of HFO-Z-1132, acetylene, HFO-1141 and HFC-152.

[0056] In some embodiments, the composition formed by any of the processes disclosed herein and comprising, consisting of, or consisting essentially of HFO-E- 1132 include an amount of HFO-E-1132 of at least 95% by weight of the resulting composition, alternatively at least 96% by weight, alternatively at least 97% by weight, alternatively at least 98% by weight, alternatively at least 99% by weight, alternatively at least 99.5% by weight, alternatively at least 99.9% by weight, or any value, range, or sub-range therebetween.TS0073-W001

[0057] In some embodiments, the compositions formed by any of the processes disclosed herein and comprising, consisting of, or consisting essentially of HFO-E- 1132 may further comprise additional compounds.

[0058] In some embodiments, the composition formed by any of the processes disclosed herein comprises, consists of or consists essentially of HFO-E-1132 and at least one additional compound selected from E-1-chloro-2-fluoroethylene (HCFO-E- 1131), Z-1-chloro-2-fluoroethylene (HCFO-Z-1131), and 1 -chloro- 1 -fluoroethylene (HCFO-1131a), while being free of or substantially free of HFO-Z-1132, and in some embodiments, being free of or substantially free of HFO-Z-1132, acetylene, HFO- 1141 and HFC-152.

[0059] In some embodiments, the composition formed by any of the processes disclosed herein comprises, consists of or consists essentially of HFO-E-1132 and at least one additional compound selected from HFC-32, HFC-125, HCFO-E-1122a, HCFO-Z-1122a, HFO-1123, HCFC-133, HCFC-133b, HCFC-123, HFC-143, HFC-41 , HCFC-22, ethylene, HCFC-142a, HFO-1132a, HCFO-1131a, HCFO-E-1131, HCFO- Z-1131, HCFO-1122, HCO-1140, acetylene and fluoroacetylene, while being free of or substantially free of HFO-Z-1132, and in some embodiments, being free of or substantially free of HFO-Z-1132, HFO-1141 and HFC-152.

[0060] In some embodiments, the composition formed by any of the processes disclosed herein comprises, consists of or consists essentially of HFO-E-1132 and at least one additional compound selected from HFC-32, HFC-125, HCFO-E-1122a, HCFO-Z-1122a, HFO-1123, HCFC-133, HCFC-133b, HCFC-123, HFC-143, HFC-41 , HCFC-22, ethylene, HCFC-142a, HFO-1132a, HCFO-1131a, HCFO-E-1131, HCFO- Z-1131, HCFO-1122, HCO-1140 and fluoroacetylene, while being free of or substantially free of HFO-Z-1132, and in some embodiments, being free of or substantially free of HFO-Z-1132, acetylene, HFO-1141 and HFC-152.

[0061] In some embodiments, the composition treated or formed by any of the processes disclosed herein may contain additional compounds in an amount of greater than 0 and less than 1 wt% of the refrigerant composition, preferably less than 0.5 weight percent, or more preferably less than 0.1 weight percent, or any value, range, or sub-range therebetween. In some embodiments, the amount of additional compounds present can be greater than 0 ppm and less than 5,000 ppmTS0073-W001 and, in particular, can range from greater than zero to about 1 ,000 ppm, about 5 to about 500 ppm and about 1 to about 100 ppm, or any value, range, or sub-range therebetween. In one embodiment, the total amount of additional compounds is greater than zero and less than 1 weight percent based on the total weight of the composition, or any value, range, or sub-range therebetween. In one embodiment, the total amount of additional compounds is less than 1000 ppm, less than 500 ppm, less than 400 ppm, less than 300 ppm, less than 200 ppm, less than 100 ppm, less than 50 ppm, less than 10 ppm, less than 5 ppm, based on the total weight of the composition, or any value, range, or sub-range therebetween.

[0062] The following Examples are provided to illustrate certain aspects of the invention and shall not limit the scope of the appended claims.EXAMPLESExample 1 : Extractive Distillation

[0063] A miscible high-boiling solvent is added to a composition including HFO-E- 1132 and HFO-Z-1132 to form a modified composition.

[0064] The miscible high-boiling solvent is methyl isobutyl ketone (MIBK), methyl ethyl ketone (MEK), heptanone, pentanone, cyclohexanone, dimethylether, diethylether, or a borate ester.

[0065] The modified composition is distilled by extractive distillation to separate a first fraction including the HFO-E-1132 from a second fraction including the HFO-Z- 1132 and extractive solvent. The first fraction is substantially free of HFO-Z-1132.

[0066] The first fraction is subjected to a simple or fractional distillation to remove or reduce the amount of one or more other impurities in the first fraction and provide the purified HFO-E-1132.

[0067] The second fraction is subjected to a simple distillation to recover the solvent, and recycle the solvent back to the extractive distillation column.Example 2: Chemical Absorption

[0068] A composition including HFO-E-1132 and HFO-Z-1132 is contacted with a chemical absorbent that selectively reacts with HFO-Z-1132 over HFO-E-1132 toTS0073-W001 form a modified composition. In some embodiments, the chemical absorbent comprises a low valent transition metal-containing absorbent, such as, for example, absorbents containing one or more of Cr, Mn, Fe, Co, Ni, Cu, Mo, Ru, Rh, Pd, Ag, W, Re, Os, Ir, Pt, Zn and Au.

[0069] The modified composition is then separated from the chemical absorbent.

[0070] Acetone, 2-butanone, 3-pentanone, methanol, ethanol, N,N- dimethylformamide, or N-methyl-pyrrolidinone is added to the modified composition for solvent scrubbing to remove or reduce the amount of any acetylene, fluoroacetylene, HCO-1140, or HFO-1141 impurities.

[0071] The modified composition is subjected to at least one of the following treatments: a simple or fractional distillation to remove or reduce the amount of one or more other impurities in the first fraction and provide the purified HFO-E-1132, drying, or passing through alumina bed for acid removal.Example 3: Chemical Reaction

[0072] A composition including HFO-E-1132 and HFO-Z-1132 is contacted with a chemical reagent that selectively reacts with the HFO-Z-1132 over the HFO-E-1132 to form a modified composition. The chemical reagent is a carbene, cyclopentadiene, pentadiene, or 1 ,3-butadiene. The HFO-Z-1132 is converted to a high boiling point compound.

[0073] The modified composition is subjected to a simple or fractional distillation to separate the high boiling compound from the HFO-E-1132 and remove or reduce the amount of one or more other impurities in composition to provide the purified HFO-E- 1132.Example 4: Distillation / Hydrochlorination / Dehydrochlorination

[0074] A composition of HFO-E / Z-1132 is distilled by simple or fractional distillation or extractive distillation and a first fraction including the HFO-E-1132 and substantially free of HFO-Z-1132 and a second fraction including mostly HFO-Z- 1132 and some HFO-E-1132 are collected.TS0073-W001

[0075] The first fraction is subjected to a simple or fractional distillation to remove or reduce the amount of one or more other impurities in the first fraction and provide the purified HFO-E-1132.

[0076] The second fraction is contacted with HF under conditions to hydrofluorinate the HFO-Z-1132 and HFO-E-1132 to HFC-143.

[0077] The HFC-143 is dehydrofluorinated under conditions to convert the HFC- 143 to HFO-E / Z-1132.

[0078] The HFO-E / Z-1132 is recycled for simple or fractional distillation or extractive distillation.Example 5: Distillation / Bromination / Debromination

[0079] A composition of HFO-E / Z-1132 is distilled by simple or fractional distillation or extractive distillation and a first fraction including the HFO-E-1132 and substantially free of HFO-Z-1132 and a second fraction including mostly HFO-Z- 1132 and some HFO-E-1132 are collected.

[0080] The first fraction is subjected to a simple or fractional distillation to remove or reduce the amount of one or more other impurities in the first fraction and provide the purified HFO-E-1132.

[0081] The second fraction is contacted with bromine and acetic acid under conditions to brominate the HFO-Z-1132 and HFO-E-1132 to HBFC-132B2.

[0082] The HBFC-132B2 is debrominated under conditions to convert the HBFC- 132B2 to HFO-E / Z-1132.

[0083] The HFO-E / Z-1132 is recycled for simple or fractional distillation or extractive distillation.Example 6: Distillation / Chlorination / Dechlorination

[0084] A composition of HFO-E / Z-1132 is distilled by simple or fractional distillation or extractive distillation and a first fraction including the HFO-E-1132 and substantially free of HFO-Z-1132 and a second fraction including mostly HFO-Z- 1132 and some HFO-E-1132 are collected.TS0073-W001

[0085] The first fraction is subjected to a simple or fractional distillation to remove or reduce the amount of one or more other impurities in the first fraction and provide the purified HFO-E-1132.

[0086] The second fraction is contacted with chlorine, with or without a catalyst, under conditions to chlorinate the HFO-Z-1132 and HFO-E-1132 to HCFC-132.

[0087] The HCFC-132 is dechlorinated under conditions to convert the HCFC-132 to HFO-E / Z-1132.

[0088] The HFO-E / Z-1132 is recycled for simple or fractional distillation or extractive distillation.OTHER EMBODIMENTS

[0089] Embodiment 1 : a process comprising: providing a composition comprising E- 1 ,2-difluoroethylene (HFO-E-1132), and Z-1 ,2-difluoroethylene (HFO-Z-1132); and separating the HFO-Z-1132 from the HFO-E-1132 by a separation process selected from extractive distillation of the provided composition, chemical absorption of the HFO-Z-1132 in the provided composition, and chemical reaction of the HFO-Z-1132 in the provided composition to provide a purified composition comprising the HFO-E- 1132.

[0090] Embodiment 2: the process of embodiment 1 , wherein the separation process is the extractive distillation of the provided composition.

[0091] Embodiment 3: the process of embodiment 2, wherein the separation process comprises adding a miscible high-boiling solvent to the provided composition to form a modified composition and distilling the modified composition to collect at least one fraction comprising HFO-E-1132 and substantially free of HFO-Z-1132.

[0092] Embodiment 4: the process of embodiment 3 further comprising distilling the at least one fraction to remove or reduce an amount of at least one impurity from the at least one fraction and form the purified composition comprising HFO-E-1132.

[0093] Embodiment 5: the process of embodiment 3, wherein the miscible high- boiling solvent is selected from methyl isobutyl ketone, methyl ethyl ketone, heptanone, pentanone, cyclohexanone, dimethylether, diethylether, and a borate ester.TS0073-W001

[0094] Embodiment 6: the process of embodiment 1 , wherein the separation process is the chemical absorption of the HFO-Z-1132.

[0095] Embodiment 7: the process of embodiment 6, wherein the chemical absorption comprises exposing the provided composition to a chemical absorbent that selectively reacts with the HFO-Z-1132 over the HFO-E-1132.

[0096] Embodiment 8: the process of embodiment 7, wherein the chemical absorbent comprises one or more low valent transition metals selected from Cr, Mn, Fe, Co, Ni, Cu, Mo, Ru, Rh, Pd, Ag, W, Re, Os, Ir, Pt, Zn and Au.

[0097] Embodiment 9: the process of embodiment 7 further comprising a solvent scrubbing following the chemical absorption to remove or reduce an amount of at least one impurity.

[0098] Embodiment 10: the process of embodiment 1 , wherein the separation process is the chemical reaction of the HFO-Z-1132.

[0099] Embodiment 11 : the process of embodiment 10, wherein the chemical reaction includes adding a reagent to the composition that selectively reacts with the HFO-Z-1132 over the HFO-E-1132.

[0100] Embodiment 12: the process of embodiment 11, wherein the reagent is a carbene that selectively react with HFO-Z-1132 via a Simmons-Smith reaction.

[0101] Embodiment 13: the process of embodiment 11, wherein the reagent is a diene selected from cyclopentadiene, pentadiene, and 1 ,3-butadiene.

[0102] Embodiment 14: the process of embodiment 11, wherein the chemical reaction forms a high boiling point compound, the process further comprising a simple or fractional distillation following the chemical reaction to separate the high boiling point compound from the HFO-E-1132 and provide the purified composition.

[0103] Embodiment 15: a process comprising: providing a composition comprising E-1 ,2-difluoroethylene (HFO-E-1132), and Z-1 ,2-difluoroethylene (HFO-Z-1132); distilling the provided composition to provide at least one first fraction comprising H FOE-1132 and substantially free of HFO-Z-1132 and at least one second fraction comprising a major amount of HFO-Z-1132 and a minor amount of HFO-E-1132; collecting the at least one first fraction as a purified composition; converting the atTS0073-W001 least one second fraction to 1 ,1 ,2-trifluoroethane, 1 ,2-dibromo-1,2-difluoroethane or 1 ,2-dichloro-1 ,2-difluoroethane and then to HFO-E / Z-1132; and recycling the HFO- E / Z-1132 for distilling.

[0104] Embodiment 16: the process of embodiment 15, wherein the converting comprises hydrofluorinating the at least one second fraction under conditions to convert the HFO-Z-1132 and HFO-E-1132 to the 1 ,1 ,2-trifluoroethane and then dehydrofluorinating the 1 ,1 ,2-trifluoroethane under conditions to convert the 1,1 ,2- trifluoroethane to HFO-E / Z-1132.

[0105] Embodiment 17: the process of embodiment 15, wherein the converting comprises brominating the at least one second fraction under conditions to convert the HFO-Z-1132 and HFO-E-1132 to the 1 ,2-dibromo-1,2-difluoroethane and then debrominating the 1,2-dibromo-1 ,2-difluoroethane under conditions to convert the 1 ,2- dibromo-1 ,2-difluoroethane to HFO-E / Z-1132.

[0106] Embodiment 18: the process of embodiment 15, wherein the converting comprises chlorinating the at least one second fraction under conditions to convert the HFO-Z-1132 and HFO-E-1132 to the 1 ,2-dichloro-1 ,2-difluoroethane and then dechlorinating the 1 ,2-dichloro-1 ,2-difluoroethane under conditions to convert the 1 ,2- dichloro-1 ,2-difluoroethane to HFO-E / Z-1132.

[0107] Embodiment 19: the process of any one of embodiments 1-18, wherein the provided composition further comprises at least one additional compound from acetylene, tetrahydrofuran, ethylene, ethane, trifluoromethane (HFC-23), difluoromethane (HFC-32), 1 ,2-dichloro-1,2-difluoroethane (HCFC-132), 1 , 1 ,2,2- tetrafluoroethane (HFC-134), 1 ,1 ,1 ,2-tetrafluoroethane (HFC-134a), 1-chloro-1 ,2- difluoroethane (HCFC-142a), 1 ,1 ,2-trifluoroethane (HFC-143), 1 ,1 ,1 -trifluoroethane (HFC-143a), 1 ,1 -difluoroethane (HFC-152a), tetrafluoroethylene (CFO-1114), 1- chloro-2,2-difluoroethylene (HCFO-1122), 1-chloro-1 ,2-difluoroethylene (HCFO- 1122a), trifluoroethylene (HFO-1123), Z-1-chloro-2-fluoroethylene (HCFO-Z-1131), E- 1-chloro-2-fluoroethylene (HCFO-E-1131), and 1-chloro-1 -fluoroethylene (HCFO- 1131a), fluoroethylene (HFO-1141), Z-1-chloro-2, 3, 3, 3, -tetrafluoropropene (HCFO-Z- 1224yd), 2,3,3,3-tetrafluoropropene (HFO-1234yf), E-1 ,1 ,1 ,3-tetrafluoropropene (HFO- E-1234ze), Z-1 ,1 ,1 ,3-tetrafluoropropene (HFO-Z-1234ze), and E-1 , 1 ,1, 4,4,4- hexafluoro-2-butene (HFO-E-1336mzz).TS0073-W001

[0108] Embodiment 20: The purified composition formed by the process of any one of embodiments 1-19, wherein the purified composition is substantially free of HFO-Z- 1132.

[0109] Embodiment 21 : the purified composition of embodiment 20, wherein the purified composition further comprises at least one compound selected from acetylene, tetrahydrofuran, ethylene, ethane, trifluoromethane (HFC-23), difluoromethane (HFC-32), 1 ,2-dichloro-1,2-difluoroethane (HCFC-132), 1 , 1 ,2,2- tetrafluoroethane (HFC-134), 1 ,1 ,1 ,2-tetrafluoroethane (HFC-134a), 1-chloro-1 ,2- difluoroethane (HCFC-142a), 1 ,1 ,2-trifluoroethane (HFC-143), 1 ,1 ,1 -trifluoroethane (HFC-143a), 1 ,1 -difluoroethane (HFC-152a), tetrafluoroethylene (CFO-1114), 1- chloro-2,2-difluoroethylene (HCFO-1122), 1-chloro-1 ,2-difluoroethylene (HCFO- 1122a), trifluoroethylene (HFO-1123), Z-1-chloro-2-fluoroethylene (HCFO-Z-1131), E- 1-chloro-2-fluoroethylene (HCFO-E-1131), and 1-chloro-1 -fluoroethylene (HCFO- 1131a), fluoroethylene (HFO-1141), Z-1-chloro-2, 3, 3, 3, -tetrafluoropropene (HCFO-Z- 1224yd), 2,3,3,3-tetrafluoropropene (HFO-1234yf), E-1 ,1 ,1 ,3-tetrafluoropropene (HFO- E-1234ze), Z-1 ,1 ,1 ,3-tetrafluoropropene (HFO-Z-1234ze), and E-1 , 1 ,1, 4,4,4- hexafluoro-2-butene (HFO-E-1336mzz).

[0110] Embodiment 22: the purified composition of embodiment 21 , wherein the at least one compound is selected from E-1-chloro-2-fluoroethylene (HCFO-E-1131), Z-1-chloro-2-fluoroethylene (HCFO-Z-1131), and 1-chloro-1 -fluoroethylene (HCFO-1131a).

[0111] Embodiment 23: the purified composition of embodiment 21 , wherein the at least one compound comprises HCFO-Z-1131.

[0112] Embodiment 24: the purified composition of embodiment 21 , wherein the at least one compound comprises HCFO-E-1131.

[0113] Embodiment 25: the purified composition of embodiment 21 , wherein the at least one compound comprises HCFO-1131a.

[0114] Embodiment 26: the purified composition of embodiment 20, wherein the purified composition is substantially free of fluoroethylene (HFO-1141).

[0115] Embodiment 27: the purified composition of embodiment 20, wherein the purified composition is substantially free of 1 ,2-difluoroethane (H FC-152).TS0073-W001

[0116] Embodiment 28: the purified composition of embodiment 20, wherein the purified composition is substantially free of acetylene.

[0117] Embodiment 29: the purified composition of embodiment 20, wherein the composition comprises at least 95 mol% HFO-E-1132.

[0118] Embodiment 30: the purified composition of embodiment 28, wherein the composition comprises at least 98 mol% HFO-E-1132.

[0119] Embodiment 31: the purified composition of embodiment 29, wherein the composition comprises at least 99 mol% HFO-E-1132.

[0120] While this specification contains many specific implementation details, these should not be construed as limitations on the scope of any inventions or of what may be claimed, but rather as descriptions of features specific to particular implementations of particular inventions. Certain features that are described in this specification in the context of separate implementations can also be implemented in combination in a single implementation. Conversely, various features that are described in the context of a single implementation can also be implemented in multiple implementations separately or in any suitable sub-combination. Moreover, although features may be described above as acting in certain combinations and even initially claimed as such, one or more features from a claimed combination can in some cases be excised from the combination, and the claimed combination may be directed to a sub-combination or variation of a sub-combination.

[0121] Similarly, while operations are depicted in a particular order, this should not be understood as requiring that such operations be performed in the particular order shown or in sequential order, or that all illustrated operations be performed, to achieve desirable results. In certain circumstances, multitasking and parallel processing may be advantageous. Moreover, the separation of various system components in the implementations described above should not be understood as requiring such separation in all implementations, and it should be understood that the described program components and systems can generally be integrated together in a single software product or packaged into multiple software products.

[0122] Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinaryTS0073-W001 skill in the art to which example embodiments belong. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that is consistent with their meaning in the context of the relevant art and will not be interpreted in an idealized or overly formal sense unless expressly so defined herein.

[0123] While the disclosure has been described with reference to a preferred embodiment, it will be understood by those skilled in the art that various changes may be made, and equivalents may be substituted for elements thereof without departing from the scope of the disclosure. In addition, many modifications may be made to adapt a particular situation or material to the teachings of the disclosure without departing from the essential scope thereof. While various aspects and embodiments have been disclosed herein, other aspects and embodiments will be apparent to those skilled in the art. The various aspects and embodiments disclosed herein are for purposes of illustration and are not intended to be limiting, with the true scope and spirit being indicated by the following claims.

Claims

TS0073-W001CLAIMSWhat is claimed is:

1. A process comprising: providing a composition comprising E-1 ,2-difluoroethylene (HFO-E-1132), and Z-1 ,2-difluoroethylene (HFO-Z-1132); and separating the HFO-Z-1132 from the HFO-E-1132 by a separation process selected from the group consisting of extractive distillation of the composition, chemical absorption of the HFO-Z-1132 in the composition, and chemical reaction of the HFO-Z-1132 in the composition to provide a purified composition comprising the HFO-E-1132.

2. The process of claim 1, wherein the separation process is the extractive distillation of the composition.

3. The process of claim 2, wherein the separation process comprises adding a solvent to the composition to form a modified composition and distilling the modified composition to collect at least one fraction comprising HFO-E-1132 and free of or substantially free of HFO-Z-1132.

4. The process of claim 3 further comprising distilling the at least one fraction to remove or reduce an amount of additional compounds from the at least one fraction and form the purified composition.

5. The process of any of claims 3 or 4, wherein the solvent is selected from the group consisting of methyl isobutyl ketone, methyl ethyl ketone, heptanone, pentanone, cyclohexanone, dimethylether, diethylether, and a borate ester.

6. The process of claim 1, wherein the separation process is the chemical absorption of the HFO-Z-1132.

7. The process of claim 6, wherein the chemical absorption comprises contacting the composition with a chemical absorbent that selectively reacts with the HFO- Z-1132 over the HFO-E-1132.

8. The process of claim 7, wherein the chemical absorbent comprises one or more low valent transition metals selected from the group consisting of Or, Mn, Fe, Co, Ni, Cu, Mo, Ru, Rh, Pd, Ag, W, Re, Os, Ir, Pt, Zn and Au.TS0073-W0019. The process of any of claims 6 to 8, further comprising a solvent scrubbing following the chemical absorption to remove or reduce an amount of at least one additional compound.

10. The process of claim 1, wherein the separation process is the chemical reaction of the HFO-Z-1132.

11. The process of claim 10, wherein the chemical reaction includes contacting the composition with a reagent that selectively reacts with the HFO-Z-1132 over the HFO-E-1132.

12. The process of claim 11 , wherein the reagent is a carbene that selectively reacts with HFO-Z-1132 via a Simmons-Smith reaction.

13. The process of claim 11 , wherein the reagent is a diene selected from the group consisting of cyclopentadiene, pentadiene, and 1 ,3-butadiene.

14. The process of any of claims 10 to 13, wherein the chemical reaction forms a high boiling point compound, the process further comprising a simple or fractional distillation following the chemical reaction to separate the high boiling point compound from the HFO-E-1132 and provide the purified composition.

15. A process comprising: providing a composition comprising E-1 ,2-difluoroethylene (HFO-E-1132) and Z-1 ,2-difluoroethylene (HFO-Z-1132); distilling the composition to provide at least one first fraction comprising HFO-E-1132 and free of or substantially free of HFO-Z-1132 and at least one second fraction comprising a major amount of HFO-Z-1132 and a minor amount of HFO-E-1132; collecting the at least one first fraction as a purified composition; converting the at least one second fraction to 1,1,2-trifluoroethane (HFC- 143), 1 ,2-dibromo-1,2-difluoroethane (HBFC-132B2) or 1 ,2-dichloro-1 ,2- difluoroethane (HCFC-132);TS0073-W001 converting the HFC-143, HBFC-132B2 or HCFC-132 to a mixture comprising a major amount of HFO-E-1132 and a minor amount of HFO-Z- 1132; and recycling the mixture for distillation.

16. The process of claim 15, wherein the at least one second fraction is converted to HFC-143 by hydrofluorination, and wherein the HFC-143 is converted to the mixture comprising a major amount of HFO-E-1132 and a minor amount of HFO-Z-1132 by dehydrofluorination.

17. The process of claim 15, wherein the at least one second fraction is converted to HBFC-132B2 by bromination, and wherein the HBFC-132B2 is converted to the mixture comprising a major amount of HFO-E-1132 and a minor amount of HFO-Z-1132 by debromination.

18. The process of claim 15, wherein the at least one second fraction is converted to HCFC-132 by chlorination, and wherein the HCFC-132 is converted to the mixture comprising a major amount of HFO-E-1132 and a minor amount of HFO-Z-1132 by dechlorination.

19. The process of any one of claims 1-18, wherein the composition comprises, consists of or consists essentially of HFO-E-1132, HFO-Z-1132 and one or more additional compounds selected from difluoromethane (HFC-32), 1,1 , 1,2, 2 pentafluoroethane (HFC-125), E-1-chloro-1,2-difluoroethylene (HCFO-E- 1122a), Z-1-chloro-1 ,2-difluoroethylene (HCFO-Z-1122a), 1 ,1 ,2- trifluoroethylene (HFO-1123), fluoroethylene (HFO-1141), 1-chloro-1,2,2- trifluoroethane (HCFC-133), 1 -chloro- 1,1,2-trifluoroethane (HCFC-133b), 1 ,1- dichloro-2,2,2-trifluoroethane (HCFC-123), 1 ,2-difluoroethane (HFC-152), 1,1 ,2- trifluoroethane (HFC-143), fluoromethane (HFC-41), chlorodifluoromethane (HCFC-22), ethylene, 1-chloro-1 ,2-difluoroethane (HCFC-142a), 1 ,1- difluoroethylene (HFO-1132a), 1-chloro-1-fluoroethene (HCFO-1131a), E-1- chloro-2-fluoroethene (HCFO-E-1131), Z-1-chloro-1 -fluoroethene (HCFO-Z- 1131), 1-chloro-2,2-difluoroethylene (HCFO-1122), vinyl chloride (HCO-1140), acetylene and fluoroacetylene.TS0073-W00120. A purified composition formed by the process of any one of claims 1-19, wherein the purified composition is free of or substantially free of HFO-Z-1132.

21. The purified composition of claim 20, wherein the purified composition further comprises at least one additional compound selected from the group consisting of HFO-E-1132 and at least one additional compound selected from HFC-32, HFC-125, HCFO-E-1122a, HCFO-Z-1122a, HFO-1123, HCFC-133, HCFC- 133b, HCFC-123, HFC-143, HFC-41 , HCFC-22, ethylene, HCFC-142a, HFO- 1132a, HCFO-1131a, HCFO-E-1131, HCFO-Z-1131 , HCFO-1122, HCO-1140, acetylene and fluoroacetylene.

22. The purified composition of claim 21, wherein the at least one compound is selected from the group consisting of E-1-chloro-2-fluoroethylene (HCFO-E- 1131), Z-1-chloro-2-fluoroethylene (HCFO-Z-1131), and 1-chloro-1- fluoroethylene (HCFO-1131a).

23. The purified composition of claim 21 , wherein the at least one compound comprises HCFO-Z-1131.

24. The purified composition of claim 21 , wherein the at least one compound comprises HCFO-E-1131.

25. The purified composition of claim 21 , wherein the at least one compound comprises HCFO-1131a.

26. The purified composition of any of claims 20 to 25, wherein the purified composition is free of or substantially free of fluoroethylene (HFO-1141).

27. The purified composition of any of claims 21 to 26, wherein the purified composition is free of or substantially free of 1,2-difluoroethane (HFC-152).

28. The purified composition of any of claims 20 to 27, wherein the purified composition is free of or substantially free of acetylene.

29. The purified composition of any of claims 20 to 28, wherein the composition comprises at least 95 mol% HFO-E-1132, preferably at least 98 mol% HFO-E- 1132, more preferably at least 99 mol% HFO-E-1132.