Transition Metal Halide Containing Catalyst Patents (Class 570/168)
  • Patent number: 6218586
    Abstract: The invention relates to a method for preparing a fluorinated product that is a first perhalogenated five-membered cyclic compound (e.g., 1,2-dichlorohexafluorocyclopentene and 1,1-dichlorooctafluorocyclopentane). This method includes reacting in a gas phase a starting material that is a second perhalogenated five-membered cyclic compound having at least one unsaturated bond, at substantially the same time with chlorine and hydrogen fluoride, in the presence of a fluorination catalyst containing an activated carbon optionally carrying thereon a metal compound, thereby to decrease the number of the at least one unsaturated bond and to increase the number of fluorine atoms of the second compound. The method is appropriate for the production of the first perhalogenated five-membered cyclic compound in an industrial scale.
    Type: Grant
    Filed: November 5, 1999
    Date of Patent: April 17, 2001
    Assignees: Central Glass Company, Limited, Nippon Zeon Co., Ltd.
    Inventors: Naoto Takada, Masatomi Kanai, Hideaki Imura, Takeo Komata
  • Patent number: 6198010
    Abstract: The present invention relates to a method for producing 1,1,1,3,3-pentafluoropropane. This method includes a first step of fluorinating 1-chloro-3,3,3-trifluoropropene in a liquid phase by hydrogen fluoride in the presence of an antimony compound as a catalyst, or a second step of fluorinating 1-chloro-3,3,3-trifluoropropene in a gas phase by hydrogen fluoride in the presence of a fluorination catalyst. If the first step is taken, 1,1,1,3,3-pentafluoropropane can be produced with a high yield. If the second step is taken, 1,1,1,3,3-pentafluoropropane can continuously be easily produced. Therefore, the second step is useful for an industrial scale production thereof. According to the invention, 1-chloro-3,3,3-trifluoropropene may be produced by a method including a step of reacting 1,1,1,3,3-pentachloropropane with hydrogen fluoride in a gas phase in the presence of a fluorination catalyst. This method is useful, because yield of 1-chloro-3,3,3-trifluoropropene is high.
    Type: Grant
    Filed: October 6, 1998
    Date of Patent: March 6, 2001
    Assignee: Central Glass Company, Limited
    Inventors: Satoshi Yoshikawa, Ryouichi Tamai, Fuyuhiko Sakyu, Yasuo Hibino, Yoshihiko Gotoh
  • Patent number: 6187976
    Abstract: The invention relates to the preparation of 1-chloro-1,1,3,3,3-pentafluoropropane (HCFC-235fa), useful as an intermediate in the production of 1,1,1,3,3-pentafluoropropane (HFC-245fa). The invention further relates to a process for the preparation of HFC-245fa comprising reacting HCFC-235fa with hydrogen in the presence of a reduction catalyst wherein the said HCFC-235fa is prepared by reacting CCl3CHCCl3 with hydrogen fluoride in the presence of fluorination catalyst in either the liquid phase or the vapor phase.
    Type: Grant
    Filed: April 9, 1998
    Date of Patent: February 13, 2001
    Assignee: AlliedSignal Inc.
    Inventors: Michael Van Der Puy, Richard Elmer Eibeck, B. V. Bindu Madhavan, Hsueh Sung Tung, Lois Anne Short Ellis
  • Patent number: 6187975
    Abstract: Perfluoropropene (PFP) hydrofluorination process in gaseous phase to obtain CF3—CHF—CF3 (A-227ea), characterized in that as catalyst fluorinated alumina containing at least 90% by weight of AlF3, is used, the HF/PFP molar ratios range from about 4:1 to 20:1, the hydrofluorination process temperature being in the range 320°-420° C.
    Type: Grant
    Filed: June 16, 1999
    Date of Patent: February 13, 2001
    Assignee: Ausimont S.p.A.
    Inventors: Letanzio Bragante, Paolo Cuzzato
  • Patent number: 6177595
    Abstract: A process of producing chlorofluoroacetones represented by a general formula where X represents independently chlorine atom or fluorine atom. The production process comprises fluorinating in a liquid phase pentachloroacetone by hydrogen fluoride in the presence of a catalyst comprising tin tetrahalide.
    Type: Grant
    Filed: September 10, 1999
    Date of Patent: January 23, 2001
    Assignee: Central Glass Company, Limited
    Inventors: Ryo Nadano, Takashi Sakaya, Mineo Watanabe, Yoshihiko Goto, Toshihiro Nakamichi, Shigeru Suenaga
  • Patent number: 6172270
    Abstract: A dichlorotrifluoroethane or the like is fluorinated with hydrogen fluoride in the presence of a fluorination catalyst which is a compound oxide of at least one metal selected from the group consisting of zinc, zirconium and manganese, and chromium, to produce R-125 and related intermediate products.
    Type: Grant
    Filed: December 23, 1998
    Date of Patent: January 9, 2001
    Assignee: Asahi Glass Company, Ltd.
    Inventor: Shin Tatematsu
  • Patent number: 6165931
    Abstract: A process is disclosed for increasing the fluorine content of a saturated or olefinic halogenated hydrocarbon starting material of the formula C.sub.n H.sub.a Cl.sub.b F.sub.c, wherein n is an integer from 1 to 6, a is an integer from 0 to to 12, b is an integer from 0 to 13 and c is an integer from 0 to 13. The process involves contacting the starting material in the vapor phase at a temperature in the range of about 150.degree. C. to about 500.degree. C. with HF and a catalytic metal supported on a trivalent lanthanum compound support (the catalytic metal being chromium, cobalt, nickel, zinc, magnesium, copper, silver and/or gold). Certain catalytic compositions including catalytic metal (e.g., chromium, nickel, cobalt, zinc and/or magnesium) supported on a support at trivalent lanthanum compound containing fluoride anion are also disclosed. The atomic ratio of catalytic metal to lanthanum in the compositions is from about 1:1 to 1:999.
    Type: Grant
    Filed: April 11, 1997
    Date of Patent: December 26, 2000
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: V. N. Mallikarjuna Rao
  • Patent number: 6166275
    Abstract: A liquid phase fluorination process for producing difluoromethane without corrosion is provided. In the process of this invention, methylene chloride and hydrogen fluoride are reacted in a reactor made of fluorinated polymer to produce a reaction product while a vaporized and superheated recycle stream of process reactants is fed into the reactor.
    Type: Grant
    Filed: September 17, 1999
    Date of Patent: December 26, 2000
    Inventors: Gustavo Cerri, Maurice William Hunt, David William Keeler, Frank Peter Young
  • Patent number: 6150572
    Abstract: Process for the regeneration of a fluorination catalyst based on Cr(III) compounds optionallay supported comprising a) the treatment at 350.degree. C.-400.degree. C. with an air/inert gas mixture and b) treatment at 300.degree. C.-380.degree. C. with a mixture of an inert gas containing from 1 to 10% by volume of hydrogen.
    Type: Grant
    Filed: May 2, 1997
    Date of Patent: November 21, 2000
    Assignee: Ausimont S.p.A.
    Inventors: Francesco Rinaldi, Paolo Cuzzato, Letanzio Bragante
  • Patent number: 6127586
    Abstract: A process for the production of pentafluoroethane which comprises the steps (i) producing a composition comprising a compound of formula C.sub.2 HCl.sub.x F.sub.y in which x=1,2 or 3 and y=2,3 or 4 provided that x+y is 5, contaminated with a compound of formula C.sub.2 Cl.sub.x+1 F.sub.y, (ii) separating the compound of formula C.sub.2 HCl.sub.x F.sub.y from the compound of formula C.sub.2 Cl.sub.x+1 F.sub.y, and (iii) contacting the compound of formula C.sub.2 HCl.sub.x F.sub.y with hydrogen fluoride in the presence of a fluorination catalyst to produce pentafluoroethane is disclosed.
    Type: Grant
    Filed: February 4, 1999
    Date of Patent: October 3, 2000
    Assignee: Imperial Chemical Industries PLC
    Inventors: John David Scott, Charles John Shields, Paul Nicholas Ewing
  • Patent number: 6127587
    Abstract: The present invention provides a process for the preparation of 1,1-difluoro-1,4-dichlorobutane by reacting 1,1,1,4-tetrachlorobutane or 1,1,4-trichlorobut-1-ene with hydrogen fluoride in the vapor phase.
    Type: Grant
    Filed: September 10, 1999
    Date of Patent: October 3, 2000
    Assignee: Zeneca Limited
    Inventor: Alfred Glyn Williams
  • Patent number: 6124511
    Abstract: A method for producing a hydrogen-containing fluorinated alkane, which comprises fluorinating at least one halogenated hydrocarbon selected from a chlorinated ethylene and a hydrogen-containing chlorinated alkane by hydrogen fluoride in the presence of a fluorination catalyst, in a reaction system where a corrosion-resistant metal material containing at least 10 wt % of aluminum, is present.
    Type: Grant
    Filed: July 30, 1997
    Date of Patent: September 26, 2000
    Assignee: Asahi Glass Company Ltd.
    Inventors: Keiichi Ohnishi, Hidekazu Okamoto
  • Patent number: 6111150
    Abstract: The present invention relates to a method for producing 1,1,1,3,3-pentafluoropropane. This method includes a step of adding hydrogen fluoride to 1,3,3,3-tetrafluoropropene in a liquid phase in the presence of a hydrohalogenation catalyst. This method is a useful method for producing 1,1,1,3,3-pentafluoropropane in an industrial scale, because yield of 1,1,1,3,3-pentafluoropropane is high. According to the invention, 1,3,3,3-tetrafluoropropene may be produced by a method including a step of reacting 1,1,1,3,3-pentachloropropane with hydrogen fluoride in a gas phase in the presence of a fluorination catalyst, or by another method including a step of reacting 1-chloro-3,3,3-trifluoropropene with hydrogen fluoride in a gas phase in the presence of a fluorination catalyst. According to the invention, 1-chloro-3,3,3-trifluoropropene may be produced by a method including a step of reacting 1,1,1,3,3-pentachloropropane with hydrogen fluoride in a gas phase in the presence of a fluorination catalyst.
    Type: Grant
    Filed: December 12, 1996
    Date of Patent: August 29, 2000
    Assignee: Central Glass Company, Limited
    Inventors: Fuyuhiko Sakyu, Yasuo Hibino, Satoshi Yoshikawa, Ryouichi Tamai, Yoshihiko Gotoh
  • Patent number: 6103944
    Abstract: Water present in a hot gaseous product stream from a reactor system A.B (FIG. 1) containing hydrogen fluoride is separated from the stream in order to eliminate a potentially corrosive combination of water and HF. The water is removed by contacting the gaseous product stream with liquid HF in a distillation column so as to obtain a bottoms product containing liquid HF and water and a top product containing dry HF and the product to be recovered. The invention encompasses the separation process, a vessel for carrying out the process (FIGS. 2 to 4), a control system for the liquid HF supply to the distillation column (FIGS. 5 and 6) and a recovery system for recovering HF employed during operation of the reactor system in different regimes employing HF as a fluorination agent, as a diluent during catalyst regeneration and/or catalyst prefluorination (FIG. 7).
    Type: Grant
    Filed: May 2, 1994
    Date of Patent: August 15, 2000
    Assignee: Imperial Chemical Industries PLC
    Inventors: Charles Brian Blake, James Malcolm Forsyth, Ann San Liow, Stephen John Adams, Ralph Jones Doy, Rowland John Porter Brierley, Jane Andrea Eileen Roberts, Brian Schofield, Neil David Shilling
  • Patent number: 6080899
    Abstract: A process for producing a fluorinated organic compound comprising: (a) reacting an organic starting material with hydrogen fluoride in the presence of a fluorination catalyst and an HFC reaction solvent to produce a product stream containing the fluorinated organic compound wherein the reaction solvent has a boiling point higher than that of the fluorinated organic compound; and (b) recovering the fluorinated organic compound from the product stream.
    Type: Grant
    Filed: January 25, 1999
    Date of Patent: June 27, 2000
    Assignee: AlliedSignal Inc.
    Inventors: David E. Bradley, Kevin Benson, David Nalewajek, Alagappan Thenappan
  • Patent number: 6080900
    Abstract: A halogenated hydrocarbon is effectively fluorinated by reacting the halogenated hydrocarbon with hydrogen fluoride in the presence of a fluorination catalyst which comprises a partially fluorinated chromium oxide containing at least one metal selected from the group consisting of ruthenium and platinum.
    Type: Grant
    Filed: September 7, 1993
    Date of Patent: June 27, 2000
    Assignee: Daikin Industries Limited
    Inventors: Takashi Shibanuma, Takashi Kanemura, Satoshi Koyama
  • Patent number: 6075172
    Abstract: The present invention provides the novel chlorofluorohydrocarbon 1,1-difluoro-1,4-dichlorobutane, and a process for its preparation comprising reacting 1,1,1,4-tetrachlorobutane or 1,1,4-trichlorobut-1-ene with hydrogen fluoride in the liquid or vapor phase. The product has useful solvent properties and is also useful in synthetic chemistry for the introduction of fluorocarbon functionality.
    Type: Grant
    Filed: January 9, 1998
    Date of Patent: June 13, 2000
    Assignee: Zeneca Limited
    Inventors: Alfred Glyn Williams, Martin Charles Bowden, Stephen Martin Brown
  • Patent number: 6074985
    Abstract: A supported Lewis acid catalyst such as antimony V on a fluorine-treated moisture-free activated carbon support is provided, as are fluorination processes using such a catalyst.
    Type: Grant
    Filed: August 3, 1999
    Date of Patent: June 13, 2000
    Assignee: Elf Atochem North America, Inc.
    Inventors: Maher Y. Elsheikh, Bin Chen
  • Patent number: 6066769
    Abstract: A process is disclosed for producing a compound of the formula: CF.sub.3 CHXCF.sub.3-z Y.sub.2 where X and Y are independently selected from the group consisting of H and Cl, and z is 0 or 1. The process involves (1) contacting CCl.sub.3 CHXCC.sub.3-z Y.sub.z,CCl.sub.2-z .dbd.CXCC.sub.3, and/or CCl.sub.2 CX.dbd.CC.sub.3-z Y.sub.z starting material, with hydrogen fluoride at a temperature of less than 200.degree. C. to produce a fluorination product of said starting material which includes at least 90 mole percent total of C.sub.3 HXY.sub.z Cl.sub.6-z-x F.sub.x saturated compounds and C.sub.3 XY.sub.z Cl.sub.5-z-y F.sub.y olefinic compounds, wherein x is an integer from 1 to 6-z and y is an integer from 1 to 5-z, (the fluorination product including no more than about 40 mole percent of the desired product, CF.sub.3 CHXCF.sub.3-z Y.sub.z); (2) contacting saturated compounds and olefinic compounds produced in (1) with hydrogen fluoride in the vapor phase at a temperature of from 200.degree. C. to about 400.
    Type: Grant
    Filed: October 6, 1998
    Date of Patent: May 23, 2000
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mario Joseph Nappa, Allen Capron Sievert, Edwin J. Warwas
  • Patent number: 6063970
    Abstract: A process is disclosed for the preparation of a chlorofluoro aliphatic hydrocarbon having the formulaCH.sub.a F.sub.3-a --CH.sub.2 --CH.sub.c Cl .sub.3-c-b F.sub.bwherein a and c are 0 or the integer 1 or 2 and b is the integer 1, 2 or 3. The process comprises reacting a chlorinated fluoroolefinic hydrocarbon of the formulaCH.sub.a F.sub.3-a --CH.dbd.CH.sub.c Cl.sub.2-cwherein a and c are as previously described, with anhydrous hydrogen fluoride and a is as described previously. This reaction is catalyzed with a compound that is a metal oxide or metal halide. The metallic part of such compound is arsenic, antimony, tin, boron or is selected from a metal in Group IVb, Vb, VIb, VIIb or VIIIb of the Periodic Table of the Elements. The desired chlorofluoro aliphatic hydrocarbon is then recovered.
    Type: Grant
    Filed: October 8, 1998
    Date of Patent: May 16, 2000
    Assignee: Laroche Industries, Inc.
    Inventors: C. Bradford Boyce, Randolph K. Belter, Terry Parker
  • Patent number: 6063969
    Abstract: A process for the preparation of 142 is provided, wherein 1130 is fluorinated in the gas phase in the presence of a catalyst which is a supported or unsupported fluorinated salt of one or more of chromium, iron, niobium, nickel, antimony, tin, tantalum or titanium. 142 is a known foam blowing agent.
    Type: Grant
    Filed: December 8, 1998
    Date of Patent: May 16, 2000
    Assignee: Elf Atochem North America, Inc.
    Inventors: Michael S. Bolmer, Bin Chen
  • Patent number: 6049016
    Abstract: There is provided a process for producing HFC-125 and/or HCFC-124 from PCE, characterized by the first reaction step of fluorinating PCE in the presence of catalyst in a liquid phase to form HCFC-123 and/or HCFC-122 and the second reaction step of fluorinating HCFC-123 and/or HCFC-122 in the presence of catalyst in a vapor phase to form HFC-125 and/or HCFC-124.This process is improved in the yield of objective products, and life of catalyst, and the controllability of reaction temperature.
    Type: Grant
    Filed: July 26, 1999
    Date of Patent: April 11, 2000
    Assignee: Daikin Industries Ltd.
    Inventors: Toshikazu Yoshimura, Yukio Homoto, Yasufu Yamada, Takehide Tsuda, Takashi Shibanuma
  • Patent number: 6040485
    Abstract: The invention relates to novel fluorinated organic compounds having the following molecular structure: ##STR1## where R.sub.F is a fluorinated carbon chain, R.sub.1H is hydrogen or a saturated hydrogenated carbon chain, R.sub.2H is hydrogen or a saturated hydrogenated carbon chain, R.sub.1H and R.sub.2H being not simultaneously hydrogen, the group ##STR2## comprising a principal chain and at least one linear or cyclic branch. These compounds may be prepared by reacting a phosphine with a halide under heating, and then hot reacting in a solvent the resulting phosphonium salt with a branched aldehyde or a ketone. These compounds have an excellent stability, a good biocompatibility and a high capacity to solubilize gases and particularly oxygen, such properties allowing their use in applications of the ophthalmological type or as an organ preservation medium.
    Type: Grant
    Filed: February 26, 1998
    Date of Patent: March 21, 2000
    Assignee: Chauvin Opsia
    Inventors: Isabelle Lattes, Bernard Feurer, Brigitte Guidetti, Viviane Payrou
  • Patent number: 6040486
    Abstract: A process is disclosed for producing HCFC-133a which includes reacting certain trihaloethene starting materials (e.g., trichloroethene) with HF in the gaseous phase at an elevated temperature in the presence of certain supported metal catalysts containing effective amounts of zinc. A catalyst of metal fluoride on a fluorinated alumina support having an atomic ratio of F to Al of at least 2.7:1 and containing .beta.-aluminum fluoride, is employed.
    Type: Grant
    Filed: December 20, 1993
    Date of Patent: March 21, 2000
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: David Richard Corbin, V. N. Mallikarjuna Rao
  • Patent number: 6028026
    Abstract: This invention provides a crystalline chromium fluoride having a cubic crystal structure (i.e., chromium trifluoride having an X-ray diffraction powder pattern as shown in Table I); and a catalytic composition comprising cubic chromium trifluoride. This invention also provides a process for changing the fluorine content of halogenated hydrocarbons containing from one to six carbon atoms, in the presence of a chromium-containing catalyst. The process is characterized by the chromium-containing catalyst comprising cubic chromium trifluoride.
    Type: Grant
    Filed: August 20, 1998
    Date of Patent: February 22, 2000
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: V. N. Mallikarjuna Rao, Munirpallam A. Subramanian
  • Patent number: 6018083
    Abstract: A process is disclosed for the separation of a mixture of HF and CF.sub.3 CClFCF.sub.3. The process involves placing the mixture in a separation zone at a temperature of from about -30.degree. C. to about 100.degree. C. and at a pressure sufficient to maintain the mixture in the liquid phase, whereby an organic-enriched phase comprising less than 50 mole percent HF is formed as the bottom layer and an HF-enriched phase comprising more than 90 mole percent HF is formed as the top layer. The organic-enriched phase can be withdrawn from the bottom of the separation zone and subjected to distillation in a distillation column to recover essentially pure CF.sub.3 CClFCF.sub.3. The distillate comprising HF and CF.sub.3 CClFCF.sub.3 can be removed from the top of the distillation column while essentially pure CF.sub.3 CClFCF.sub.3 can be recovered from the bottom of the distillation column.
    Type: Grant
    Filed: April 1, 1999
    Date of Patent: January 25, 2000
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: William H. Manogue, Mario Joseph Nappa, Allen Capron Sievert, V. N. Mallikarjuna Rao
  • Patent number: 6018084
    Abstract: A manufacturing method for 1,1,1,3,3-pentafluoropropane comprises a first process, in which 1,1,1-trifluoro-3-chloro-2-propene is obtained by inducing a reaction between 1,1,1,3,3-pentafluoropropane and hydrogen fluoride in the vapor phase, and a second process, in which the 1,1,1,3,3-pentafluoropropane is obtained by inducing a reaction between 1,1,1-trifluoro-3-chloro-2-propene and hydrogen in the vapor phase, and 1,1,1-trifluoro-3-chloro-2-propene obtained in the first process is supplied to the second process after removing the HCl by-products. This invention can provide a new economic manufacturing method of 1,1,1,3,3-pentafluoropropane with high yield and selectivity.
    Type: Grant
    Filed: June 25, 1998
    Date of Patent: January 25, 2000
    Assignee: Daikin Industries Ltd.
    Inventors: Tatsuo Nakada, Hirokazu Aoyama, Akinori Yamamoto
  • Patent number: 6013846
    Abstract: An azeotrope containing HF and 1233zd is provided, as are methods for separating this azeotrope from mixtures of HF and 1233zd which are HF-rich or 1233zd-rich and methods for making use of the azeotrope and separation methods to improve processes for preparing 1233zd, an intermediate used in the preparation of 245fa. 245fa is a known foam blowing agent and refrigerant.
    Type: Grant
    Filed: March 5, 1998
    Date of Patent: January 11, 2000
    Assignee: Elf Atochem North America, Inc.
    Inventors: John A. Wismer, Michael S. Bolmer, Bin Chen
  • Patent number: 6011185
    Abstract: There is provided a process for producing HFC-125 and/or HCFC-124 from PCE, characterized by the first reaction step of fluorinating PCE in the presence of catalyst in a liquid phase to form HCFC-123 and/or HCFC-122 and the second reaction step of fluorinating HCFC-123 and/or HCFC-122 in the presence of catalyst in a vapor phase to form HFC-125 and/or HCFC-124.This process is improved in the yield of objective products, and life of catalyst, and the controllability of reaction temperature.
    Type: Grant
    Filed: August 20, 1997
    Date of Patent: January 4, 2000
    Assignee: Daikin Industries Ltd.
    Inventors: Toshikazu Yoshimura, Yukio Homoto, Yasufu Yamada, Takehide Tsuda, Takashi Shibanuma
  • Patent number: 5981814
    Abstract: A process is disclosed for the preparation of a fluorinated aliphatic hydrocarbon having the formulaCH.sub.a F.sub.3-a --CH.sub.2 --CH.sub.b F.sub.3-bwherein a is 0 or the integer 1 or 2 and b is 0 or the integer 1, 2 or 3. The reaction occurs in the vapor phase. A chlorofluoro olefin of the formulaCH.sub.c Cl.sub.2-c .dbd.CH--CH.sub.d F.sub.3--dwherein c is 0 or the integer 1 or 2, and d is 0 or the integer 1 or 2 is treated in the vapor phase with hydrogen fluoride. This treating is catalyzed with a compound that is a metal oxide, a metal halide or a mixture thereof. The metallic part of such compound is selected from a metal in Group IIIa, IIIb, IVa, Va, IVb, Vb, VIa, VIb, VIIb and VIII of the Periodic Table of the Elements. The treating is carried out for a time sufficient to form the desired fluorinated aliphatic hydrocarbon which is subsequently recovered from the vapor phase reaction.The process is particularly suitable for the preparation of 1,1,1,3,3-pentafluoropropane.
    Type: Grant
    Filed: March 23, 1998
    Date of Patent: November 9, 1999
    Assignee: LaRoche Industries Inc.
    Inventors: C. Bradford Boyce, Randolph K. Belter
  • Patent number: 5969198
    Abstract: A process for preparing 1,1,1,3,3-pentafluoropropane from a hydrochlorocarbon of the formula C.sub.3 H.sub.y Cl.sub.x, wherein x is an integer from 3 to 5, y is an integer from 1 to 3, x+y=4, 6, or 8, and x-y=2 is provided.
    Type: Grant
    Filed: June 27, 1997
    Date of Patent: October 19, 1999
    Assignee: AlliedSignal Inc.
    Inventors: Alagappan Thenappan, Michael Van Der Puy, Hsueh S. Tung
  • Patent number: 5959166
    Abstract: A method for concurrently producing different hydrofluoro carbons, comprising the reaction of halocarbon or hydrohalocarbon with hydrogen fluoride in a reaction system consisting of a series of at least two discrete reactors, in the presence of catalysts, said reactors each being provided with different reactant materials and differing in reaction conditions including the catalysts and/or reaction temperature, thereby flexibly controlling their production rates in accordance with fluctuations in their demand, and eliminating the risk of constructing large scale plants responsible for individual hydrofluorocarbons.
    Type: Grant
    Filed: November 7, 1997
    Date of Patent: September 28, 1999
    Assignee: Korea Institute of Science and Technology
    Inventors: Hoon Sik Kim, Moon Jo Chung, Kun You Park, Young Soo Kwon
  • Patent number: 5932776
    Abstract: The invention relates to catalytic fluorination of perchloroethylene or of pentachloroethane in the gas phase by means of hydrofluoric acid.A mixed catalyst is employed, made up of nickel and chromium oxides, halides and/or oxyhalides deposited on a support consisting of aluminium fluoride or of a mixture of aluminium fluoride and alumina.
    Type: Grant
    Filed: November 6, 1996
    Date of Patent: August 3, 1999
    Inventors: Bernard Cheminal, Eric Lacroix, Andre Lantz
  • Patent number: 5919993
    Abstract: At least one halogenated compound selected from the group consisting of 1,1,1,4,4,4-hexafluoro-2,3-dichlorobutane, 1,1,1,4,4,4-hexafluoro-2-chloro-2-butene, 1,1,1,2,4,4,4-heptafluoro-2-butene and 1,1,1,2,2,4,4,4-octafluorobutane, is prepared by reacting 1,1,2,3,4,4-hexachloro-1,3-butadiene with hydrogen fluoride in a gas phase in the presence of a fluorinating catalyst. Desired products can be prepared commercially according to the present invention.
    Type: Grant
    Filed: September 3, 1993
    Date of Patent: July 6, 1999
    Assignee: Daikin Industries Ltd.
    Inventors: Tatsuo Nakada, Hirokazu Aoyama, Satoshi Koyama
  • Patent number: 5902912
    Abstract: A process for producing a hydrofluorocarbon (HFC) comprising (a) providing a fluoropolymer-lined reactor; (b) adding a chlorinated organic compound in liquid phase and a fluorination agent to the reactor; and (c) reacting at least a portion of the chlorinated organic compound with at least a portion of the fluorination agent to produce the HFC.
    Type: Grant
    Filed: June 26, 1997
    Date of Patent: May 11, 1999
    Assignee: AlliedSignal Inc.
    Inventors: Hsueh Sung Tung, Daniel Christopher Merkel, Addison Miles Smith
  • Patent number: 5902913
    Abstract: A process for the co-production of two or more hydrofluoroalkanes which comprises contacting an alkene or a halogenated alkane with hydrogen fluoride at elevated temperature in the presence of a fluorination catalyst to produce a first hydrofluoroalkane and wherein an organic precursor to a second hydrofluoroalkane is provided in the process whereby to produce a second hydrofluoroalkane in addition to the first hydrofluoroalkane. In particularly preferred embodiments of the process, the first hydrofluoroalkane is 1,1,1,2-tetrafluoroethane derived from 1-chloro-2,2,2-trifluoroethane or trichloroethylene and the second hydrofluoroalkane is one or more of pentafluoroethane, difluoromethane and 1,1,2,2-tetrafluoroethane.
    Type: Grant
    Filed: February 6, 1997
    Date of Patent: May 11, 1999
    Assignee: Imperial Chemical Industries PLC
    Inventors: Richard Llewellyn Powell, John David Scott, Charles John Shields, David William Bonniface
  • Patent number: 5900514
    Abstract: The invention relates to the manufacture of difluoromethane by catalytic gas-phase fluorination of methylene chloride.The operation is carried out in the presence of oxygen at a temperature of between 330 and 450.degree. C. and with a bulk or supported chromium catalyst.
    Type: Grant
    Filed: June 14, 1996
    Date of Patent: May 4, 1999
    Assignee: Elf Atochem S.A.
    Inventors: Benoit Requieme, Eric Lacroix, Andre Lantz
  • Patent number: 5898088
    Abstract: A process for the production of pentafluoroethane which comprises the steps (i) producing a composition comprising a compound of formula C.sub.2 HCl.sub.x F.sub.y in which x=1, 2 or 3 and y=2, 3 or 4 provided that x+y is 5, contaminated with a compound of formula C.sub.2 Cl.sub.x+1 F.sub.y, (ii) separating the compound of formula C.sub.2 HCl.sub.x F.sub.y from the compound of formula C.sub.2 Cl.sub.x+1 F.sub.y and (iii) contacting the compound of formula C.sub.2 HCl.sub.x F.sub.y with hydrogen fluoride in the presence of a fluorination catalyst whereby to produce pentafluoroethane.
    Type: Grant
    Filed: June 14, 1996
    Date of Patent: April 27, 1999
    Assignee: Imperial Chemical Industries PLC
    Inventors: John David Scott, Charles John Shields, Paul Nicholas Ewing
  • Patent number: 5894075
    Abstract: The addition of hydrogen fluoride to unsaturated C--C groups and the chlorine-fluorine exchange on perhalogenated carbon atoms can be advantageously catalyzed by a catalyst mixture which comprises at least partially fluorinated titanium halide in combination with tin (IV) halide.
    Type: Grant
    Filed: December 23, 1996
    Date of Patent: April 13, 1999
    Assignee: Solvay Fluor und Derivate GmbH
    Inventors: Max Braun, Werner Rudolph, Stefan Palsherm
  • Patent number: 5866729
    Abstract: A process for the selective and high yield preparation of 1,1-difluoroethane (CHF.sub.2 --CH.sub.3, HFC-152a) from chloroethene and anhydrous hydrogen fluoride is disclosed. The process involves the reaction of chloroethene with anhydrous hydrogen fluoride in a liquid phase between the temperatures of 30.degree. and 160.degree. C. in the presence of a tin catalyst and at least one compound selected from the group consisting of alkali metal halides and saturated halogenated hydrocarbons.
    Type: Grant
    Filed: January 2, 1997
    Date of Patent: February 2, 1999
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mario Joseph Nappa, William Robert Williams
  • Patent number: 5849963
    Abstract: According to the method for producing difluoromethane and 1,1,1,2-tetrafluoroethane, having the steps of:(1) reacting methylene chloride and 1,1,2-trichloroethylene with hydrogen fluoride in a vapor phase In the presence of a fluorinating catalyst and 1,1,1,2-tetrafluoroethane in a first reactor; and(2) reacting 1,1,1-trifluorochloroethane with hydrogen fluoride in a vapor phase in the presence of a fluorinating catalyst in a second reactor, and supplying the reaction mixture from the second reactor to the first reactor, HFC-32 can be obtained in high conversion and high selectivity by fluorinating HCC-30 using commonly a large (excess) amount of HF which is required for producing HFC-134a.
    Type: Grant
    Filed: June 7, 1996
    Date of Patent: December 15, 1998
    Assignee: Daikin Industries, Ltd.
    Inventors: Yukio Homoto, Kunitada Tanaka, Takashi Shibanuma, Satoshi Komatsu, Satoshi Koyama
  • Patent number: 5847244
    Abstract: A production method in which reaction processes are divided into two regions comprising one reaction region where mainly perohloroethylene is made to react with HF in a vapor phase in the presence of a catalyst and the other reaction region where HCFC-123 (CF.sub.3 CHCl.sub.2) and/or HCFC-124 (CF.sub.3 CFHCl) is made to react with HF in a vapor phase in the presence of a catalyst, the former region being kept at a higher pressure and the latter region at a lower pressure during the reaction procedure. By this method it is possible to keep the conversion of perchloroethylene at a high level while securing the life of a catalyst, and it is also possible to raise the selectivity of HFC-125. This is a method of producing HFC-125 in which the content of CFC-115 is lowered to not more than 15 vol % of the total amount of HFC-125 and CFC-115, and then CFC-115 is made to react with hydrogen in the presence of a catalyst.
    Type: Grant
    Filed: February 13, 1998
    Date of Patent: December 8, 1998
    Assignee: Daikin Industries, Ltd.
    Inventors: Takashi Shibanuma, Yukio Homoto, Satoshi Komatsu, Toshikazu Yoshimura
  • Patent number: 5847242
    Abstract: A process is disclosed for changing the fluorine content of halogenated hydrocarbons containing from 1 to 6 carbon atoms, in the presence of a multiphase catalyst, which is characterized by preparing certain single phase solid catalyst precursors containing two metal components (e.g., a divalent component of Mn, Co, Zn, Mg and/or Cd and a trivalent component of Al, Ga, Cr and/or V) which have structures that collapse at about 600.degree. C. or less; and producing said catalyst by heating the precursor to produce a multiphase composition wherein a phase containing one of the metal components is homogeneously dispersed with a phase containing the other metal component, and at least when the precursor contains no fluoride, contacting said multiphase composition with a vaporizable fluorine-containing fluorination compound at a temperature of from about 200.degree. C. to 450.degree. C. Also disclosed are single phase fluoride compositions having the formula MM'F.sub.5 (H.sub.2 O).sub.
    Type: Grant
    Filed: November 21, 1996
    Date of Patent: December 8, 1998
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Velliyur Nott Mallikarjuna Rao, Munirpallam A. Subramanian
  • Patent number: 5841007
    Abstract: The present invention relates to a process for manufacturing 1,1,1,2-tetrafluoroethane (HFC-134a) from trichloroethylene (TCE) and hydrogen fluoride (HF) by reacting the HCFC-133a with the HF to produce the HFC-134a and reacting the TCE with the HF to produce 1-choro-2,2,2-trifluoroethane (HCFC-133a), characterized by that a part of said HF is mixed with the mixture containing the HFC-134a and the remaining portion of said HF is fed with said TCE in portions to at least two sections of a reactor for producing said HCFC-133a. According the present process, the temperature change in the reactor for producing HCFC-133a is maintained within a narrow range over the whole reaction procedures, and the catalytic activity is well maintained. Further, the formation of by-products is considerably prevented and thus the productivity is remarkably enhanced.
    Type: Grant
    Filed: April 12, 1996
    Date of Patent: November 24, 1998
    Assignee: Korea Institute of Science and Technology
    Inventors: Byoung Sung Ahn, Young Soo Kwon, Kun You Park, Moon Jo Chung
  • Patent number: 5831136
    Abstract: This invention relates to processes for the manufacturing of 1,1-dichlorotetrafluoroethane (i.e., CF.sub.3 CCl.sub.2 F or CFC-114a), and more particularly to processes for manufacturing CF.sub.3 CCl.sub.2 F substantially free of its isomer, 1,2-dichlorotetrafluoroethane (i.e., CClF.sub.2 CClF.sub.2 or CFC-114).
    Type: Grant
    Filed: April 29, 1996
    Date of Patent: November 3, 1998
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Velliyur Nott Mallikarjuna Rao
  • Patent number: 5824828
    Abstract: This invention relates to a process for the manufacture of C.sub.2 Cl.sub.3 F.sub.3 reaction product from a mixture of C.sub.2 Cl.sub.4 F.sub.2 isomers, and more particularly to the manufacture of C.sub.2 Cl.sub.3 F.sub.3 reaction product which is substantially free of CClF.sub.2 CClF.sub.2.
    Type: Grant
    Filed: April 29, 1996
    Date of Patent: October 20, 1998
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Velliyur Nott Mallikarjuna Rao
  • Patent number: 5817894
    Abstract: Difluoromethane is produced from dichloromethane and hydrogen fluoride by continuous reaction in a liquid medium comprising an inorganic fraction and an organic fraction, in which a content by weight of the said organic fraction in the liquid medium is maintained at less than or equal to 25% of the sum of the inorganic and organic fractions and a content by weight of dichloromethane in the liquid medium is maintained at less than or equal to 10% of the sum of the inorganic and organic fractions.
    Type: Grant
    Filed: September 3, 1997
    Date of Patent: October 6, 1998
    Assignee: Solvay (Societe Anonyme)
    Inventors: Vincent Wilmet, Francine Janssens
  • Patent number: 5770779
    Abstract: This invention is a process for the selective preparation of fluorinated hydrocarbons from chlorinated hydrocarbons while minimizing formation of oligomeric and polymeric byproducts. The process comprises providing a liquid phase containing chlorinated hydrocarbon, HF, a tin catalyst, and at least one compound selected from the group consisting of metal and nonmetal alkoxides, and heating the mixture and isolating the fluorinated hydrocarbon formed.
    Type: Grant
    Filed: January 2, 1997
    Date of Patent: June 23, 1998
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mario Joseph Nappa, William Robert Williams
  • Patent number: 5763707
    Abstract: There is provided a process for the production of pentafluoroethane which comprises contacting a hydrofluorochloroethane having the formula: C.sub.2 H.sub.1 Cl.sub.1+x F.sub.1+y wherein x and y are each independently 0,1,2 or 3 provided x+y is 3 with hydrogen fluoride in the vapor phase and in the presence of a fluorination catalyst which comprises zinc or a compound of zinc and chromia, chromium fluoride or chromium oxyfluoride.
    Type: Grant
    Filed: September 19, 1996
    Date of Patent: June 9, 1998
    Assignee: Imperial Chemical Industries PLC
    Inventors: John David Scott, Michael John Watson, Paul Nicholas Ewing
  • Patent number: 5763704
    Abstract: There is provided a process for the production of difluoromethane which comprises contacting a dichloromethane with hydrogen fluoride in the presence of a fluorination catalyst comprising zinc or a compound of zinc and metal oxide, fluoride or oxyfluoride.
    Type: Grant
    Filed: September 6, 1995
    Date of Patent: June 9, 1998
    Assignee: Imperial Chemical Industries PLC
    Inventors: John David Scott, Michael John Watson, David William Bonniface