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US 2011/0237843 A1Published application
Process for the manufacture of hexafluoro-2-butene
AssigneeHoneywell International Inc.
InventorsHsueh Sung Tung, Haiyou Wang
Life of this patent
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Abstract
Hexafluoro-2-butene (HFO-1336) is a low global warming potential blowing agent, refrigerant and solvent. This invention provides methods for making the compound, including the cis-isomer, from the readily available raw materials, carbon tetrachloride and ethylene. The trans-isomer formed in the process can be isomerized into cis-isomer by the use of an isomerization catalyst.
Claims44
A process for the manufacture of 1,1,1,4,4,4-hexafluoro-2-butene comprising the steps of:
- (a) contacting carbon tetrachloride with ethylene in the presence of an effective amount of a metal catalyst complex comprising a metal and an organic ligand under conditions effective to facilitate an addition reaction and to form a product stream comprising 1,1,1,2,4,4,4-heptachlorobutane, and
- (b) contacting HF with the 1,1,1,2,4,4,4-heptachlorobutane formed in step (a) under conditions effective to facilitate a fluorination reaction and to form a product stream mixture comprising 1,1,1,4,4,4-hexafluoro-2-butene and/or 1,1,1,4,4,4-hexafluoro-2-chlorobutane and isolating the 1,1,1,4,4,4-hexafluoro-2-butene therefrom.
A process for the manufacture of 1,1,1,4,4,4-hexafluoro-2-butene comprising the steps of:
- (a) contacting carbon tetrachloride with ethylene in the presence of an effective amount of a metal catalyst complex comprising a metal and an organic ligand under conditions effective to facilitate an addition reaction and to form a first product stream comprising 1,1,1,3-tetrachloropropane,
- (b) dehydrochlorinating the 1,1,1,3-tetrachloropropane formed in step (a) under conditions effective to form a second product stream mixture comprising 3,3,3-trichloro-1-propene and/or 1,1,3-trichloro-1-propene,
- (c) contacting carbon tetrachloride with the product stream mixture formed in step (b) in the presence of an effective amount of a metal catalyst complex comprising a metal and an organic ligand under conditions effective to facilitate an addition reaction and to form a third product stream comprising 1,1,1,2,4,4,4-heptachlorobutane, and
- (d) contacting HF with the 1,1,1,2,4,4,4-heptachlorobutane formed in step (c) under conditions effective to facilitate a fluorination reaction and to form a fourth product stream mixture comprising 1,1,1,4,4,4-hexafluoro-2-butene and/or 1,1,1,4,4,4-hexafluoro-2-chlorobutane and isolating the 1,1,1,4,4,4-hexafluoro-2-butene therefrom.
1 more element
Dependencies are inferred from the claim text.