Method for separating 1-chloro-3,3,3-trifluoropropene and hydrogen fluoride, and method for producing 1-chloro-3,3,3-trifluoropropene by using same
US-9221732-B2 · Dec 29, 2015 · US
US2016152536A1 · US · A1
| Field | Value |
|---|---|
| Publication number | US-2016152536-A1 |
| Application number | US-201414903627-A |
| Country | US |
| Kind code | A1 |
| Filing date | Jul 8, 2014 |
| Priority date | Jul 12, 2013 |
| Publication date | Jun 2, 2016 |
| Grant date | — |
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A method of separating a composition containing at least one organofluorine compound from at least one inorganic compound by contacts the composition with a semipermeable membrane. Other methods separate a organofluorine compound from a composition containing at least one other organofluorine compound or chlorocarbon. Methods also include isolating a single organofluorine compound from a composition comprising a mixture of organofluorine compounds, chlorocarbons, and/or inorganic compounds.
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1 . A process for separating an organofluorine compound from a composition, comprising: contacting a feed stream comprising at least one organofluorine compound and at least one additional compound with a semipermeable membrane to form a first stream rich in the at least one organofluorine compound. 2 . The process of claim 1 , wherein the at least one additional compound is chosen from inorganic compounds, and additional organofluorine compounds, and organochlorines. 3 . The process of claim 2 , wherein the feed stream comprises at least one organofluorine compound and at least one inorganic compound, and contacting the feed stream with a semipermeable membrane forms a first stream rich in the at least one organofluorine compound and a second stream rich in the at least one inorganic compound. 4 . The process of claim 3 , wherein the at least one organofluorine compound and the at least one inorganic compound form an azeotrope or azeotrope-like mixture. 5 . The process of claim 3 , wherein the at least one inorganic compound is selected from the group consisting of hydrogen fluoride (HF), carbon monoxide (CO), carbon dioxide (CO 2 ), hydrogen chloride (HCl), water, oxygen, nitrogen, NOx, chlorine, and mixtures thereof. 6 . The process of claim 5 , wherein the at least one inorganic compound comprises HF. 7 . The process of claim 2 , wherein the feed stream comprises a first organofluorine compound and at least one additional organofluorine compound and/or chlorocarbon, and contacting the feed stream with a semipermeable membrane forms a first stream rich in the first organofluorine compound and a second stream rich in the at least one additional organofluorine compound and/or organochlorine. 8 . The process of claim 7 , further comprising subjecting the second stream to at an additional separation process selected from an adsorption process, a distillation process, a phase separation process, or an additional membrane separation process. 9 . The process of claim 2 , wherein the feed stream comprises a first organofluorine compound, at least one additional organofluorine compound and/or organochlorine, and at least one inorganic compound, wherein contacting the feed stream with a semipermeable membrane forms a first stream rich in the first organofluorine compound and the at least one additional organofluorine compound and/or organochlorine and a second stream rich in the at least one inorganic compound. 10 . The process of claim 9 , further comprising contacting the first stream with a second semipermeable membrane to form a first stream rich in the first organofluorine compound and a second stream rich in the at least one additional organofluorine compound and/or organochlorine. 11 . The process of claim 9 , further comprising separating the first organofluorine compound and each of the at least one additional organofluorine compound and/or chlorocarbon into individual streams by contacting the first stream rich in the first organofluorine compound and the at least one additional organofluorine compound and/or organochlorine with a series of additional semipermeable membranes. 12 . The process of claim 1 , wherein the at least one organofluorine compound is selected from the group consisting of hydrofluorocarbons (HFCs), hydrofluoroolefins (HFOs), hydrochlorofluorocarbons (HCFCs), hydrochlorofluoroolefins (HCFOs), and mixtures thereof. 13 . The process of claim 12 , wherein the at least one organofluorine compound is selected from the group consisting of HFC-134a, HFC-125, HFC-32, HFC-23, HFC-1132a, HFC-142b, HFO-1234yf, HFO-1234ze, HFO-1243zf, HFO-1336mzz, HCFO-1233zd, HCFO-1233xf, and mixtures thereof. 14 . The process of claim 1 , wherein the at least one inorganic, compound comprises a polar compound having a molecular weight of 50 Da or less. 15 . The process of claim 1 , wherein the at least one organofluorine compound comprises 3 to 6 carbon atoms. 16 . The process of claim 1 , wherein the semipermeable membrane is selected from a film, a laminate, structure, hollow fibers, and coated fibers. 17 . The process of claim 1 , wherein the semipermeable membrane comprises at least one polymer selected from the group consisting of polyimide, polypropylene, polytetrafluoroethylene, polyvinylidene fluoride, polyvinyl fluoride, polychlorotrifluoroethylene, perfluoroalkoxy polymer, fluorinated ethylene-propylene, polyethylenetetrafluoroethylene, and perfluoropolyether. 18 . The process of claim 17 , wherein the semipermeable membrane comprises polyvinylidene fluoride. 19 . The process of claim 1 , wherein the process is carried out at a temperature ranging from about 0° C. to about 150° C. 20 . The process of claim 1 , further comprising subjecting the first stream to an additional separation process selected from an adsorption process, a distillation process, or a phase separation process, or an additional membrane separation process.
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