Organic compounds -- part of the class 532-570 series – Organic compounds – Halogen containing
Patent
1996-12-27
1998-12-08
Kight, John
Organic compounds -- part of the class 532-570 series
Organic compounds
Halogen containing
570161, C07C 1700
Patent
active
058472436
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
This invention relates to a novel process for producing a vic-dichloro-fluorinated alkene having chlorine atoms bonded to carbon atoms of the unsaturated bond, and a process for preparing a fluorinated alkane through the vic-dichloro-fluorinated alkene as an intermediate.
BACKGROUND ART
Halogenated hydrocarbons containing fluorine have heretofore been used as detergents, cooling mediums and others. In recent years, to cope with problem of the damage of the global environment, international restriction on the use of chlorine-containing fluorinated hydrocarbons is now being tightened, and thus, there is an increasing demand for substitutes therefor. Especially fluorinated alkane derivatives containing no chlorine attract attention in view of protection of the environment because they invite no destruction of the ozone layer.
For example, fluorinated alkanes represented by the following formula: or may form a perfluoroalkylene group together, and R.sup.3, R.sup.4, R.sup.5 and R.sup.6 independently represent a hydrogen or fluorine atom, are expected widely for uses such as detergents, solvents, propellants, heating mediums for heat pumps and others. As specific examples of the fluorinated alkanes, there can be mentioned 1,1,2,2,3,3-hexafluorocyclopentane disclosed as being useful for a detergent in U.S. Pat. No. 5,084,199, and 1,2,3,3,4,4,5,5-octafluorocyclopentane is disclosed as being useful for a detergent and a desiccating agent in Japanese Patent Application No. 5-88022.
Now there is an urgent request for establishment of a process for producing in a commercial scale fluorinated alkanes as substitutes for the chlorine-containing fluorinated hydrocarbons. Especially a process for producing intermediates used for the production of fluorinated alkanes in a commercial scale and at a reduced cost is eagerly required. Vic-dichloro-fluorinated alkenes having chlorine atoms bonded to the carbon atoms of the carbon-carbon unsaturation in the molecule and other fluorinated alkenes are used as intermediates for the production of the fluorinated alkanes. For example, there have been proposed a process for allowing 1,2-dichlorohexafluorocyclopentene to react with hydrogen in the presence of a palladium or nickel catalyst to yield 1,1,2,2,3,3-hexafluorocyclopentane in DE-A 3,735,467 and U.S. Pat. No. 5,084,199; a process for treating 1,2-dichlorohexafluorocyclopentene with a fluorinating agent such as a potassium fluoride to yield a fluorine-substituted compound in U.S. Pat. No. 3,024,290; and a process for allowing said fluorine-substituted compound to react with hydrogen in the presence of a palladium catalyst to yield 1,2,3,3,4,4,5,5-octafluorocyclopentane in Japanese Patent Application No. 5-88022.
As examples of the process for producing vic-dichloro-fluorinated alkene, there can be mentioned two processes, i.e., a process using a perchloro-olefin and a process using a perchloro-conjugated diene compound.
As an example of the process using a perchloro-olefin, a process has been proposed in J. Am. Chem. Soc., 67, 1235 (1945) wherein octachlorocyclopentene is allowed to react with a mixture of antimony trifluoride and antimonytrifluoro-dichloride to yield 1,2-dichlorohexafluorocyclopentene. However, the reaction involved in this process is stoichiometric, and thus an expensive reagent must be used in a salient amount, and the yield is low, i.e, about 50%.
As another example, a process has been proposed in DE-C 3,935,493 wherein octachlorocyclopentene is allowed to react with chlorine and hydrogen fluoride in the presence of antimony pentachloride to yield 1,2-dichlorohexafluorocyclopentene. It is described in this patent that the antimony pentachloride used is fluorinated by the action of hydrogen fluoride to pentavalent antimony fluoride which has a fluorinating action, and, simultaneously with the fluorination, trivalent antimony produced as a by-product during the fluorination reaction is reproduced into pentavalent antimony by the action of chlorine gas, and thus, the antimony compound can be
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Henne et al, Journal of the American Chemical Society, vol. 67, Aug. 9, 1945, No. 8, pp. 1234-1237.
Sekiya Akira
Watanabe Kazunori
Yamada Toshiro
Dahlen Garth M.
Japan as represented by Director General of the Agency of Indust
Kight John
Nippon Zeon Co. Ltd.
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