Metal Oxide Containing Catalyst Patents (Class 570/169)
  • Patent number: 6316681
    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: December 4, 1996
    Date of Patent: November 13, 2001
    Assignee: Central Glass Company, Limited
    Inventors: Satoshi Yoshikawa, Ryouichi Tamai, Fuyuhiko Sakyu, Yasuo Hibino, Yoshihiko Gotoh
  • Patent number: 6307114
    Abstract: In the preparation of 1,1,1-trifluoro-2-chloroethane (HCFC 133a) by means of hydrofluorination in the gas phase of trichloroethylene (TCE) in the presence of a carried catalyst based on Cr2O3 it is possible to prolong the catalyst life by feeding to the hydrofluorination reactor, along with trichloroethylene, little amounts (7-25 mols % calculated on the mixture with trichloroethylene) of 133a.
    Type: Grant
    Filed: June 30, 1997
    Date of Patent: October 23, 2001
    Assignee: Ausimont S.p.A.
    Inventor: Paolo Cuzzato
  • Patent number: 6300530
    Abstract: Catalyst comprising a supported Cr(III) amorphous compound, characterized in that the support is formed by an aluminum trifluoride (AlF3) having an high surface area obtainable by alumina fluorination with gaseous HF at an initial temperature lower than 300° C., the temperature is rised with a temperature gradient≦100° C./hour up to the final temperature>320° C. and <450° C., the fluorination is continued at the final temperature until feeding a HF molar amount at least equal to the stoichiometric with respect to the alumina, the fluorination being carried out until a fluorinated alumina with a fluorine content not lower than 95% of the stoichiometric is obtained.
    Type: Grant
    Filed: May 5, 1999
    Date of Patent: October 9, 2001
    Assignee: Ausimont S.p.A.
    Inventor: Paolo Cuzzato
  • Patent number: 6300531
    Abstract: A fluorination catalyst comprising chromium oxide having a specific surface area of from 170 m2/g to 300 m2/g, which can catalyze the fluorination of a halogenated hydrocarbon with hydrogen fluoride and has a high activity and a long catalyst life.
    Type: Grant
    Filed: May 5, 1995
    Date of Patent: October 9, 2001
    Assignee: Daikin Industries, Ltd.
    Inventors: Takashi Shibanuma, Yoshio Iwai, Satoshi Koyama
  • Patent number: 6297411
    Abstract: Mixed fluorination catalyst comprising one or more nickel and chromium oxides, halides and/or oxyhalides deposited on a support composed of aluminium fluoride or of a mixture of aluminium fluoride and alumina, characterized in that the weight of nickel/weight of chromium ratio is between 0.08 and 0.25, preferably between 0.1 and 0.2.
    Type: Grant
    Filed: December 4, 2000
    Date of Patent: October 2, 2001
    Assignee: Elf Atochem S.A.
    Inventors: Philippe Bonnet, Eric Jorda, Eric Lacroix
  • Patent number: 6288293
    Abstract: The invention relates to a process for the preparation of 1,1,1,2-tetrafluoroethane from 1,1,1-trifluoro-2-chloroethane and hydrogen fluoride in the gas phase, in which a catalyst containing chromium and magnesium is used which is obtainable by precipitating chromium(III) hydroxide by reacting 1 mol of a water-soluble chromium(III) salt with at least 1.5 mol of magnesium hydroxide or magnesium oxide in the presence of water, the reaction mixture is made into a paste containing chromium hydroxide and a magnesium salt, and the paste is then dried and treated with hydrogen fluoride at temperatures of 20 to 500° C.
    Type: Grant
    Filed: June 21, 1993
    Date of Patent: September 11, 2001
    Assignee: Solvay (Societe Anonyme)
    Inventors: Wolfgang Wanzke, Günter Siegemund, Wilfried Schmieder
  • Patent number: 6281395
    Abstract: A process is disclosed for the manufacture of CF3CHFCF3 containing less than 0.01 ppm (CF3)2C═CF2. The process involves (a) contacting hexafluoropropene in the vapor phase at a temperature of less than about 260° C. with hydrogen fluoride in the presence of a selected fluorination catalyst or produce a product containing less than 10 parts (CF3)2C═CF2 per million parts of CF3CHFCF3; and (b) treating the product of (a) as necessary to remove excess (CF3)2C═CF2. Suitable catalysts include: (i) an activated carbon treated to contain from about 0.1 to about 10 weight % added alkali or alkaline earth metals, (ii) three dimensional matrix porous carbonaceous materials, (iii) supported metal catalysts comprising trivalent chromium, and (iv) unsupported chrome oxide prepared by the pyrolysis of (NH4)2Cr2O7.
    Type: Grant
    Filed: April 1, 1999
    Date of Patent: August 28, 2001
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mario Joseph Nappa, V. N. Mallikarjuna Rao, Allen Capron Sievert
  • Patent number: 6268541
    Abstract: The invention provides a process for the preparation of 1,1,1,2,2-pentafluoroethane by fluorinating in the gas phase a halogenated hydrocarbon feedstock containing 2-chloro-1,1,1,2-tetrafluoroethane with hydrogen fluoride, the process being characterized in that: (i) a fluorinated chromium oxide obtained by fluorinating a chromium oxide represented by the formula: CrOm (1.5<m<3) is used as the catalyst, (ii) the mixing ratio (by mole) of hydrogen fluoride to halogenated hydrocarbon feedstock ranges from 1.5 to 10, and (iii) the fluorination is conducted at a temperature of 250 to 350° C. The process makes it possible to prepare easily HFC-125 reduced in the contents of CFCs.
    Type: Grant
    Filed: April 5, 2000
    Date of Patent: July 31, 2001
    Assignee: Daikin Industries, Ltd.
    Inventors: Satoru Kono, Takashi Shibanuma, Takashi Kanemura, Toshikazu Yoshimura, Kazuhiro Takahashi
  • Patent number: 6242659
    Abstract: The invention relates to the synthesis of difluoromethane by gas-phase catalytic fluorination of methylene chloride. To lengthen the lifetime of the catalyst the operation is carried out in the presence of chlorine.
    Type: Grant
    Filed: June 14, 1996
    Date of Patent: June 5, 2001
    Assignee: Elf Atochem, S.A.
    Inventors: Benoit Requieme, Sylvain Perdrieux, Bernard Cheminal, Eric Lacroix, Andre Lantz
  • Patent number: 6232514
    Abstract: Process for preparing pentafluoroethane (HFC-125) wherein 1,1,1-trifluorodichloroethane (HFC-123) is reacted with HF at a temperature from 310° to 380° C., in the presence of a catalyst comprising Cr2O3 supported on preformed AlF3. HFC-125 is obtained with high yields (up to 60-70% and over), high conversions (over 80%) and high selectivity, i.e. formation of by-product in very low amounts (5% by moles at most) Moreover, the catalyst maintains a high activity for a long time also with high organic charges.
    Type: Grant
    Filed: March 5, 1997
    Date of Patent: May 15, 2001
    Assignee: Ausimont S.p.A.
    Inventors: Paolo Cuzzato, Antonio Masiero, Francesco Rinaldi
  • 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: 6194621
    Abstract: A process for the production of difluoromethane which comprises contacting bis(fluoromethyl)ether in the liquid phase with boron trifluoride under conditions such that the molar ratio of boron trifluoride to bis(fluoromethyl) ether is at least 0.5:1.
    Type: Grant
    Filed: June 11, 1996
    Date of Patent: February 27, 2001
    Assignee: Imperial Chemical Industries, PLC
    Inventors: Paul David Bernard Bujac, Jane Lesley Butcher
  • 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: 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: 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: 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: 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: 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: 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: 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: 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: 5981813
    Abstract: Fluorination process of halogenated organic compounds with gaseous anhydrous HF characterized in that a catalyst comprising a supported Cr(III) amorphous compound is used, wherein the support consists in an aluminum trifluoride (AlF.sub.3) having an high surface area and an high pore volume obtainable by fluorination with gaseous HF of alumina having surface area of at least 150 m.sup.2 /g and pore volume not lower than 0.3 cc/g and wherein said alumina comprises from 0.5 up to 15% by weight of silicon oxide, the chromium amount being comprised between 1 and 20% by weight.
    Type: Grant
    Filed: May 20, 1997
    Date of Patent: November 9, 1999
    Assignee: Ausimont S.p.A.
    Inventors: Paolo Cuzzato, Letanzio Bragante, Francesco Rinaldi
  • Patent number: 5962753
    Abstract: Process for the manufacture of pentafluoroethane ?HFC 125! by reaction of perchloroethylene with hydrogen fluoride in the vapor phase over a fluorination catalyst in a fluorination reactor with recycle of dichlorotrifluoroethane ?HCFC 123! and chlorotetrafluoroethane ?HCFC 124! to the fluorination reactor, wherein tetrafluoroethane ?HFC 134a! is also recycled to the fluorination reactor. The tetrafluoroethane and the chlorotetrafluoroethane can both be separated from the product stream in a single distillation column and recycled, together to the fluorination reactor.
    Type: Grant
    Filed: February 18, 1997
    Date of Patent: October 5, 1999
    Assignee: Imperial Chemical Industries PLC
    Inventors: Charles John Shields, Paul Nicholas Ewing
  • 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: 5919728
    Abstract: A fluorination catalyst based on of an amorphous Cr (III) compound and on a compound of another metal selected from Mg, Ca, Sr, Ba, Sc, Ti and Zr, wherein the atomic ratio of Cr/other metal is between 50:1 and 1:1, said compounds are supported on a AlF.sub.3 support and being prepared by impregnating the support with a concentrated aqueous solution containing a soluble Cr (III) salt and a soluble salt of the other metal. The catalyst can be used in gaseous phase reactions.
    Type: Grant
    Filed: April 15, 1997
    Date of Patent: July 6, 1999
    Assignee: Ausimont S.P.A.
    Inventors: Francesco Rinaldi, Paolo Cuzzato, Letanzio Bragante
  • 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: 5895825
    Abstract: A process for the preparation of 245fa is provided, wherein 1233zd is first fluorinated to 1234ze, followed by fluorination of 1234ze to 245fa. 245fa is a known foam blowing agent and refrigerant.
    Type: Grant
    Filed: December 1, 1997
    Date of Patent: April 20, 1999
    Assignee: Elf Atochem North America, Inc.
    Inventors: Maher Y. Elsheikh, Michael S. Bolmer, Bin Chen
  • Patent number: 5880317
    Abstract: The present invention relates to a process for the reduction dechlorination of ClCF.sub.2 CFClCF.sub.2 Cl to HCF.sub.2 CHFCF.sub.2 H comprising the step of contacting 1,2,3-trichloropentafluoroethane and H.sub.2 over a catalyst selected from the group consisting of palladium, platinum, ruthinium, rhodium, iridium and mixtures thereof under reaction conditions sufficent to produce a product stream containing 1,1,2,3,3-pentafluoropropane. The present invention further relates to a three step process wherein the ClCF.sub.2 CFClCF.sub.2 Cl to be reduced is synthesized by:(a) reacting HF with a compound of formula I: XCH.dbd.CYCH.sub.2 X, where X is H, Cl, or F, Y is H or Cl;to give a compound of formula II: CH.sub.2 XCFYCH.sub.2 X, where X and Y are the same as in the compound of formula I:(b) chlorinating the compound of formula II to give a compound of formula III: CCl.sub.3-m F.sub.m CFClCCl.sub.3-m F.sub.m where m is zero or 1, and(c) fluorinating the compound of formula III to give CClF.sub.2 CFClCF.sub.
    Type: Grant
    Filed: September 30, 1993
    Date of Patent: March 9, 1999
    Assignee: AlliedSignal Inc.
    Inventor: M. Van Der Puy
  • Patent number: 5880316
    Abstract: 1,1,1,2-tetrafluoroethane (134a) is prepared by reacting, in the gas phase, trichloroethylene with 1,1,1-trifluorochloroethane (133a) and hydrofluoric acid with trichloroethylene/133a molar ratios ranging from 5/95 to 50/50, in the presence of a catalyst consisting of Cr.sub.2 O.sub.3 carried on AlF.sub.3.The process provides 134a yields higher than 90% and permits an exceptionally long life of the catalyst. In this way it is possible to realize a continuous process by recycling the unreacted trichloroethylene and 133a, thereby making up for the relatively low global conversion of the reagents.
    Type: Grant
    Filed: November 19, 1996
    Date of Patent: March 9, 1999
    Assignee: Ausimont S.p.A.
    Inventors: Paolo Cuzzato, Antonio Masiero
  • Patent number: 5852222
    Abstract: The present invention provides the novel chlorofluorohydrocarbon 1,1-difluoro-1,4-dichlorobutane, and a process for its preparation by reacting 1,1,1,4-tetrachlorobutane with hydrogen fluoride in the liquid phase. The product has useful solvent properties and is also useful in synthetic chemistry for the introduction of fluorocarbon functionality.
    Type: Grant
    Filed: September 3, 1996
    Date of Patent: December 22, 1998
    Assignee: Zeneca Limited
    Inventors: Alfred Glyn Williams, Martin Charles Bowden, Stephen Martin Brown
  • 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: 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: 5817895
    Abstract: Process for the regeneration of a fluorination catalyst based on Cr(III) compounds optionally supported, which comprise a) treatment at 350.degree.-40.degree. C. with an air/inert gas mixture and b) treatment at 300.degree.-380.degree. C. with a mixture of an inert gas containing from 0.5 to 5% by volume of an aliphatic hydrocarbon C.sub.1 -C.sub.8.
    Type: Grant
    Filed: May 2, 1997
    Date of Patent: October 6, 1998
    Assignee: Ausimont, S.p.A.
    Inventors: Paolo Cuzzato, Francesco Rinaldi, Letanzio Bragante
  • Patent number: 5811603
    Abstract: A process for the fluorination of 1230za is provided, wherein 1230za is contacted with HF in the gas phase in the presence of an aluminum fluoride or chromium-based fluorination catalyst under conditions sufficient to produce a reaction mixture containing 1233zd, 1234ze and 245fa. 245fa is a known foam blowing agent and refrigerant, while 1233zd and 1234ze are known intermediates useful for preparing 245fa.
    Type: Grant
    Filed: December 1, 1997
    Date of Patent: September 22, 1998
    Assignee: Elf Atochem North America, Inc.
    Inventor: Maher Y. Elsheikh
  • 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