Patent number: 5714655
Abstract: 2,2,3-trichloro-1,1,1,3,3-pentafluoropropane is used as a raw material, to which not less than 4.5 equivalent parts of hydrogen are added to effect a hydrogenation reaction in the presence of a noble metal catalyst, particularly a palladium catalyst, by the vapor phase method to manufacture 1,1,1,3,3-pentafluoropropane. Further, propane, propene, and hexachloropropene, etc. are chlorofluorinated in the presence of a metal catalyst to produce 2,2,3-trichloro-1,1,1,3,3-pentafluoropropane, then this compound is reduced with hydrogen in the presence of a noble metal catalyst to produce 1,1,1,3,3-pentafluoropropane. 2,2,3-trichloro-1,1,1,3,3-pentafluoropropane and 1,1,1,3,3-pentafluoropropane can thus be efficiently and economically produced.
Type:
Grant
Filed:
December 8, 1995
Date of Patent:
February 3, 1998
Assignee:
Daikin Industries, Ltd.
Inventors:
Akinori Yamamoto, Eiji Seki, Hirokazu Aoyama, Seiji Takubo, Tatsuo Nakada
Patent number: 5714654
Abstract: A method is proposed for producing 1,1,1,3,3-pentafluoropropane, in which 1,1,3,3,3-pentafluoropropene is reduced at a temperature between 40.degree. C. and 300.degree. C. by reacting it with hydrogen in a gas phase in the presence of a palladium catalyst. Further, a method is proposed for producing 1,1,1,3,3-pentafluoropropane and/or 1,1,3,3,3-pentafluoropropene, in which the raw material 2-chloro-1,1,3,3,3-pentafluoropropene is hydrogenated especially at a temperature between 30.degree. C. and 450.degree. C. in the presence of a catalyst composed of at least one metal selected from palladium, platinum and rhodium. Further, a method is proposed of producing 1,1,3,3,3-pentafluoropropene, in which 1,1,1,3,3-pentafluoro-2,3-dichloropropane is dechlorinated by using hydrogen in the presence of a metal oxide catalyst. Based on these production methods, 1,1,1,3,3-pentafluoropropane and/or 1,1,3,3,3-pentafluoropropene can thus be produced with high yield rates.
Type:
Grant
Filed:
December 8, 1995
Date of Patent:
February 3, 1998
Assignee:
Daikin Industries Ltd.
Inventors:
Akinori Yamamoto, Eiji Seki, Hirokazu Aoyama, Tatsuo Nakada
Patent number: 5679875
Abstract: The present inventions provide manufacturing methods of 1,1,1,2,3-pentafluoropropene characterized by the reaction of removing HF by means of the contact of 1,1,1,2,3,3-hexafluoropropane in the gas state with active carbon or active carbon added with metallic salt. 1,1,1,2,3-pentafluoropropene can be produced from easily available 1,1,1,2,3,3-hexafluoropropane by cost-effective industrial methods at high yields according to these inventions.The inventions also provide manufacturing methods of 1,1,1,2,3-pentafluoropropane characterized by reducing 1,1,1,2,3-pentafluoropropene with hydrogen under the presence of a hydrogenation catalyst consisting of palladium added with one or more of silver, copper, gold, tellurium, zinc, chromium, molybdenum, and thallium or under the presence of a rhodium catalyst. The desired product can be produced at high reactivities and high selectivities according to these inventions.
Type:
Grant
Filed:
November 30, 1994
Date of Patent:
October 21, 1997
Assignee:
Daikin Industries, Ltd.
Inventors:
Hirokazu Aoyama, Eiji Seki
Patent number: 5608128
Abstract: The present invention provides a production method of obtaining the mixture of 1,1,1,4,4,4-hexafluoro-2,3-dichloro-2-butene, 1,1,1,4,4,4-hexafluoro-2-chloro-2-butene and 1,1,1,4,4,4-hexafluoro-2-butene (1,1,1,4,4,4-hexafluoro-2-butene compounds) by reacting at least one of butane, butene and butadiene with chlorine and HF in the presence of a suitable catalyst, and also a production method of obtaining 1,1,1,4,4,4-hexafluorobutane by reducing said products in the presence of a noble metal catalyst.
Type:
Grant
Filed:
July 27, 1995
Date of Patent:
March 4, 1997
Assignee:
Daikin Industries, Ltd.
Inventors:
Tatsuo Nakada, Hirokazu Aoyama, Seiji Takubo
Patent number: 5599783
Abstract: A cleaning solvent composition comprising at least one selected from the group consisting of 1H,2H/-hexafluorocyclobutane, 1,2,2,3,3-pentafluoro-cyclobutane, 1,2,2,3,3,4,4,5,5-nonafluorocyclopentane, 1H/2H-octafluorocyclopentane, 1H,2H/-octafluorocyclopentane, 1H/3H-octafluorocyclopentane, 1H,4H,2H/-heptafluorocyclopentane, 1H,2H/4H-heptafluorocyclopentane, 1H,2H,4H/-heptafluorocyclopentane, 1H,3H/2H-heptafluorocyclopentane, 1H,2H/3H-heptafluorocyclopentane and 1H,2H/3H-heptafluorocyclopentane and a method for cleaning or drying acticles employing thereof and use of the composition as a cleaning agent.
Type:
Grant
Filed:
May 9, 1995
Date of Patent:
February 4, 1997
Assignee:
Daikin Industries, Ltd.
Inventors:
Satoshi Ide, Takahiro Matsuda, Hirokazu Aoyama, Akinori Yamamoto
Patent number: 5557019
Abstract: A new 3,3-dichloro-1,1,1,2,2,4,4,5,5,5-decafluoropentane as a precursor of alternatives of refrigerants, etc.A method to obtain the target products at high yield and high selectivity by reacting tetrafluoroethylene and difluorodichloromethane under the Lewis acid catalyst to produce the new compound and an economical method in a continuous reaction state.A production method of 1,1,1,2,2,4,4,5,5,5-decafluoropentane at high yield by reducing 3,3-dichloro-1,1,1,2,2,4,4,5,5,5-decafluoropentane.
Type:
Grant
Filed:
August 24, 1994
Date of Patent:
September 17, 1996
Assignee:
Daikin Industries Ltd.
Inventors:
Hirokazu Aoyama, Satoru Kohno, Satoshi Koyama
Patent number: 5516951
Abstract: 1,1,1,4,4,4-Hexafluoro-2-butene is prepared by reacting 1,1,1-trifluoro-2,2-dichloroethane with copper and an amine, and then 1,1,1,4,4,4-hexafluorobutane is prepared by reacting 1,1,1,4,4,4-hexafluoro-2-butene with hydrogen.1,1,1,4,4,4-Hexafluorobutane, which is used as a coolant, a blowing agent or a cleaner and can reserves the environment, is easily obtained, and 1,1,1,4,4,4-hexafluoro-2-butene, which is useful as an intermediate for the 1,1,1,4,4,4-hexafluorobutane, or as a monomer of fluorine-containing polymers is easily prepared in a good yield.
Type:
Grant
Filed:
May 19, 1995
Date of Patent:
May 14, 1996
Assignee:
Daikin Industries Ltd.
Inventor:
Hirokazu Aoyama