Process for producing 1,1,1,4,4,4-hexafluorobut-2-ene
AssigneeThe Chemours Company Fc, LLC
InventorsSHENG PENG, ALLEN CAPRON SIEVERT
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Abstract
A process for producing E-1,1,1,4,4,4-hexafluorobut-2-ene comprises contacting 1,1,2,4,4-pentachlorobuta-1,3-diene with hydrogen fluoride in the vapor phase in the presence of a fluorination catalyst. A process for producing Z-1,1,1,4,4,4-hexafluorobut-2-ene further comprises contacting E-1,1,1,4,4,4-hexafluoro-2-butene with chlorine in the presence of a catalyst to produce 2,3-dichloro-1,1,1,4,4,4-hexafluorobutane, followed by reaction with base to produce 1,1,1,4,4,4-hexafluoro-2-butyne, and subsequently hydrogenating hexafluoro-2-butyne to produce Z-1,1,1,4,4,4-hexafluoro-2-butene.
Claims29
A process for producing E-1,1,1,4,4,4-hexafluorobut-2-ene comprising contacting 1,1,2,4,4-pentachlorobuta-1,3-diene with HF in the vapor phase in the presence of a fluorination catalyst to produce a product mixture comprising E-1,1,1,4,4,4-hexafluorobut-2-ene.
A composition comprising 1,1,2,4,4-pentachlorobuta-1,3-diene, E-1,1,2,3,4-pentachlorobuta-1,3-diene, and Z-1,1,2,3,4-pentachlorobuta-1,3-diene.
A process for producing E-1,1,1,4,4,4-hexafluorobut-2-ene comprising:
- (a) producing 1,1,2,4,4-pentachlorobuta-1,3-diene by contacting trichloroethylene with a dimerization catalyst to produce a product mixture comprising 1,1,2,4,4-pentachlorobuta-1,3-diene;
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- (b) contacting 1,1,2,4,4-pentachlorobuta-1,3-diene with HF in the presence of a fluorination catalyst to produce a product mixture comprising E-1,1,1,4,4,4-hexafluorobut-2-ene, wherein the process is a vapor phase process.
A process for producing E-1,1,1,4,4,4-hexafluorobut-2-ene comprising:
- (a) producing 1,1,2,4,4-pentachlorobuta-1,3-diene by contacting trichloroethylene with a dimerization catalyst and pentachloroethane to produce a product mixture comprising 1,1,2,4,4-pentachlorobuta-1,3-diene;
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- (b) contacting 1,1,2,4,4-pentachlorobuta-1,3-diene with HF in the presence of a fluorination catalyst to produce a product mixture comprising E-1,1,1,4,4,4-hexafluorobut-2-ene, wherein the process is a vapor phase process.
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A process for producing 1,1,2,4,4-pentachlorobuta-1,3-diene comprising contacting trichloroethylene with pentachloroethane and a dimerization catalyst to produce a product mixture comprising 1,1,2,4,4-pentachlorobuta-1,3-diene.
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A process to produce Z-1,1,1,4,4,4-hexafluorobut-2-ene, comprising:
- (a) contacting trichloroethylene with a dimerization catalyst to produce a product mixture comprising 1,1,2,4,4-pentachlorobuta-1,3-diene;
- (b) contacting 1,1,2,4,4-pentachlorobuta-1,3-diene with HF in the presence of a fluorination catalyst to produce a product mixture comprising E-1,1,1,4,4,4-hexafluoro-2-butene, wherein the process is a vapor phase process;
- (c) contacting E-1,1,1,4,4,4-hexafluoro-2-butene with a chlorine source to produce a product mixture comprising 2,3-dichloro-1,1,1,4,4,4-hexafluorobutane;
- (d) contacting 2,3-dichloro-1,1,1,4,4,4-hexafluorobutane with base to produce a product mixture comprising 1,1,1,4,4,4-hexafluoro-2-butyne;
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- (e) contacting 1,1,1,4,4,4-hexafluoro-2-butyne with H2 to produce a product mixture comprising Z-1,1,1,4,4,4-hexafluorobut-2-ene.
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A composition comprising E-1,1,1,4,4,4-hexafluoro-2-butene, Z-1,1,1,4,4,4-hexafluoro-2-butene, 1,1,1,2,2,4,4,4-octafluorobutane, and one or more additional compounds chosen from 1,1,1,4,4,4-hexafluorobutane, Z-1,1,1,4,4,4-hexafluoro-2-chloro-2-butene, E-1,1,1,4,4,4-hexafluoro-2-chloro-2-butene and HCFO-1335, wherein HCFO-1335 is at least one of E-1-chloro-1,1,4,4,4-pentafluorobutene, Z-1-chloro-1,1,4,4,4-pentafluorobutene, E-2-chloro-1,1,4,4,4-pentafluorobutene, and Z-2-chloro-1,1,4,4,4-pentafluorobutene.
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A composition comprising E-1,1,1,4,4,4-hexafluoro-2-butene, 1,1,1,2,2,4,4,4-octafluorobutane, 1,1,1,4,4,4-hexafluorobutane, and Z-2-chloro-1,1,1,4,4,4-hexafluorobutene.
Dependencies are inferred from the claim text.