Organic compounds -- part of the class 532-570 series – Organic compounds – Halogen containing
Patent
1995-03-29
1996-10-29
Siegel, Alan
Organic compounds -- part of the class 532-570 series
Organic compounds
Halogen containing
C07C 1908
Patent
active
055697968
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
This application is a 371 of PCT/JP93/01395 filed Sep. 30, 1993.
This invention relates to a process for producing a fluorinated saturated hydrocarbon.
BACKGROUND ART
Chloro Fluoro Carbons (CFCs) have heretofore been used as a detergent and a refrigeration medium. However, in recent years, an increasing attention has been paid to a problem of pollution nuisance in a global environment and restriction of the use of CFCs has been universally acceded to. Therefore, alternatives of CFCs have been intensively investigated and developed. Especially chlorine-free fluorinated saturated hydrocarbons attract public attention from a viewpoint of environmental protection because there is no problem of depletion of the ozone layer.
For example, fluorinated saturated hydrocarbons represented by the following formula (2): ##STR2## wherein R and R' represent a perfluoroalkyl group, or both R and R' are bonded together to form a perfluoroalkylene group which is a part of a ring, are expected to be used as detergents, solvents, propellants, and heating media for heat pumps. As a specific example of the fluorinated saturated hydrocarbons, 1,1,2,2,3,3-hexafluorocyclopentane is described as a detergent in U.S. Pat. No. 5,084,199.
As means for producing fluorinated saturated hydrocarbons which are expected to be widely used in future, a process is generally known wherein a corresponding unsaturated hydrocarbon having chlorine or bromine bonded to the carbon-to-carbon double bond is allowed to react with hydrogen in the presence of a base such as a basic alkali metal salt or amine by using a palladium catalyst or a nickel catalyst (for example, DE-A-3,735,467 and U.S. Pat. No. 5,084,199). As specific example of such process, there can be mentioned a process wherein 1,2-dichloro-3,3,4,4,5,5-hexafluoro-cyclopentene is hydrogenated in the presence of triethylamine by using a Raney nickel catalyst to produce 1,1,2,2,3,3-hexafluorocyclopentane, and a process wherein 1,2-dichloro-3,3,4,4,5,5-hexafluoro-cyclopentene is hydrogenated in the presence of sodium acetate by using a palladium catalyst to produce 1,1,2,2,3,3-hexafluorocyclopentane. However, these processes have problems in economy and operating characteristics because acidic substances such as hydrogen chloride or hydrogen bromide produced as by-products are deposited as an alkali metal salt or an amine salt and thus an operation of separating the target substance is indispensable.
DISCLOSURE OF INVENTION
To solve the problems of the prior art, the inventors conducted researches and found that, where a fluorinated unsaturated hydrocarbon represented by the formula (1) shown below is reacted with hydrogen by using a platinum catalyst, a fluorinated saturated hydrocarbon represented by the formula (2) shown below can be produced in a high yield; that, since a basic substance is not used, hydrogen fluoride produced by a side reaction can be separated from the target substance only by a distillation procedure; and further that the recovered hydrogen fluoride can be effectively utilized as a raw material for other reactions. The present invention has been completed on the basis of these findings.
In accordance with the present invention, there is provided a process for producing a fluorinated saturated hydrocarbon represented by the formula (2): ##STR3## wherein R and R' represent a perfluoroalkyl group or both R and R' are bonded together to form a perfluoroalkylene group which is a part of a ring, which comprises reacting a fluorinated unsaturated hydrocarbon represented by the formula (1): platinum catalyst.
BEST MODE FOR CARRYING OUT THE INVENTION
The starting compound used in the present invention is a fluorinated unsaturated hydrocarbon represented by the above-mentioned formula (1). As examples of R and R', there can be mentioned a perfluoroalkyl group having 1 to 4 carbon atoms such as a trifluoromethyl group, a pentafluoroethyl group, a heptafluoro-n-propyl group, a heptafluoro-isopropyl group, a nonafluoro-n-butyl group, a nonafluoro-isobutyl gro
REFERENCES:
patent: 4902839 (1990-02-01), Bielefeldt
patent: 4954666 (1990-09-01), Bielefeldt
Mitsuda Yasuhiro
Yamada Toshiro
Nippon Zeon Co. Ltd.
Siegel Alan
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