Transhalogenation Or Disproportionation Patents (Class 570/163)
  • Patent number: 8859829
    Abstract: The present invention relates in part to a method of stabilizing chloropropenes, such as 1,1,2,3-tetrachloropropene, otherwise known to decompose and degrade, and to the resulting stabilized chloropropene, using a morpholine compound and/or a trialkyl phosphate compound as defined herein. Such stabilized chloropropenes are useful in the manufacture of hydrofluoroolefins such as 2,3,3,3-tetrafluoroprop-1-ene (1234yf).
    Type: Grant
    Filed: March 11, 2014
    Date of Patent: October 14, 2014
    Assignee: Honeywell International Inc.
    Inventors: Haluk Kopkalli, Haiyou Wang, Hsueh Sung Tung, Daniel C. Merkel
  • Publication number: 20140275651
    Abstract: The invention relates to a process to prepare 2-chloro-3,3,3-trifluoropropene (HCO-1233xf) or 2-chloro-1,1,12-tetrafluoropropane (HCFC-244bb) using dichloro-trifluoropropanes and/or trichloro-difluoropropanes, and to prepare 2-chloro-3,3,3-trifluoropropene (HCO-1233xf) using various 242 and 243 isomers.
    Type: Application
    Filed: March 11, 2014
    Publication date: September 18, 2014
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Haiyou Wang, Daniel C. Merkel, Hsueh Sung Tung, Selma Bektesevic
  • Patent number: 8524955
    Abstract: Disclosed is a process for making hexafluoro-2-butyne comprising the steps of: (a) providing a composition comprising CF3CX?CXCF3, where X=halogen; and (b) treating CF3CX?CXCF3 with a dehalogenation catalyst in the presence of a halogen acceptor compound Y, where Y is not hydrogen. The halogen acceptor compound Y is a material capable of being halogenated, preferably a compound having a multiple bond, such as an alkyne, alkene, allene, or carbon monoxide. Another suitable material capable of being halogenated is a cyclopropane. A catalyst effectively transfers halogen from CF3CX?CXCF3 to the halogen acceptor compound. Since Y is not hydrogen, the formation of CF3CX?CHCF3 is greatly reduced or eliminated.
    Type: Grant
    Filed: May 19, 2011
    Date of Patent: September 3, 2013
    Assignee: Honeywell International Inc.
    Inventors: Andrew Joseph Poss, David Nalewajek, Haridasan K. Nair, Michael Van Der Puy, Rajiv Ratna Singh
  • Patent number: 8350099
    Abstract: Disclosed are fluorovinyl ether functionalized aromatic diesters and derivatives thereof. The compounds disclosed have utility as functionalized monomers and comonomers in polyesters, polyamides, and the like. It has been found that incorporation of the monomers into polymers provides improved soil resistance to shaped articles produced from the polymers.
    Type: Grant
    Filed: September 1, 2010
    Date of Patent: January 8, 2013
    Assignee: E I du Pont de Nemours and Company
    Inventors: Neville Everton Drysdale, Surbhi Mahajan, Kenneth Gene Moloy, Fredrik Nederberg, Joel M. Pollino, Joachim C. Ritter
  • Patent number: 8309774
    Abstract: The invention is directed to a process for preparing 2,2,2,3-tetrafluoropropene (1234yf), comprising: (i) contacting 1,1,2,3-tetrachloropropene (1230xa) with hydrogen fluoride HF in gas phase in the presence of a fluorination catalyst under conditions sufficient to produce a reaction mixture; (ii) separating the reaction mixture into a first stream comprising HCl, 2,2,2,3-tetrafluoropropene (1234yf) and a second stream comprising HF, 2-chloro-3,3,3-trifluoro-1-propene (1233xf) and 1,1,1,2,2-pentafluoropropane (245cb); (iii) recycling at least a part of the second stream at least in part back to step (i).
    Type: Grant
    Filed: March 9, 2012
    Date of Patent: November 13, 2012
    Assignee: Arkema France
    Inventors: Anne Pigamo, Dominique Deur-Bert, Laurent Wendlinger
  • Patent number: 8158836
    Abstract: The invention is directed to a process for preparing 2,3,3,3-tetrafluoropropene (1234yf), comprising: (i) contacting 1,1,2,3-tetrachloropropene (1230xa) with hydrogen fluoride HF in gas phase in the presence of a fluorination catalyst under conditions sufficient to produce a reaction mixture; (ii) separating the reaction mixture into a first stream comprising HCl, 2,3,3,3-tetrafluoropropene (1234yf) and a second stream comprising HF, 2-chloro-3,3,3-trifluoro-1-propene (1233xf) and 1,1,1,2,2-pentafluoropropane (245cb); (iii) recycling at least a part of the second stream at least in part back to step (i).
    Type: Grant
    Filed: December 23, 2010
    Date of Patent: April 17, 2012
    Assignee: Arkema France
    Inventors: Anne Pigamo, Dominique Deur-Bert, Laurent Wendlinger
  • Patent number: 7906693
    Abstract: A process is disclosed for making CH2?CFCF3. The process involves contacting CH2ClCF2CF3 with H2 in a reaction zone in the presence of a catalyst including a catalytically effective amount of palladium supported on a support selected from chromium oxide, fluorinated chromium oxide, chromium fluoride, aluminum oxide, aluminum fluoride and/or fluorinated alumina, to produce CH2?CFCF3. The mole ratio of H2 to the CH2ClCF2CF3 fed to the reaction zone is between about 1:1 and about 4:1.
    Type: Grant
    Filed: October 31, 2007
    Date of Patent: March 15, 2011
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Mario Joseph Nappa, Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
  • Publication number: 20100185027
    Abstract: The present invention involves methods for isomerization of 1234zc. Also provided are methods for managing 1,1,3,3-tetrafluoropropene produced as a byproduct in a process for synthesizing trans-1,3,3,3-tetrafluoropropene from 245fa, wherein 1234zc is converted into trans/cis-1234ze with the help of a catalyst in the absence of HF and in an isomerization reactor, or is converted into 1234zc and/or 245fa with the help of a catalyst in the presence of HF in a separate reactor or preferably in the same reactor of 245fa dehydrofluorination.
    Type: Application
    Filed: January 13, 2010
    Publication date: July 22, 2010
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: HAIYOU WANG, KONSTANTIN A. POKROVSKI, HSUEH S. TUNG, Michael Van Der Puy
  • Publication number: 20100152503
    Abstract: A crystalline alpha-chromium oxide where from about 0.05 atom % to about 5 atom % of the chromium atoms in the alpha-chromium oxide lattice are replaced by divalent copper (Cu+2) atoms is disclosed. Also disclosed is a chromium-containing catalyst composition comprising as a chromium-containing component the crystalline copper-substituted alpha-chromium oxide; and methods for preparing a composition comprising the crystalline copper-substituted alpha-chromium oxide. One method involves (a) co-precipitating a solid by adding ammonium hydroxide to an aqueous solution of a soluble copper salt and a soluble trivalent chromium salt that contains at least three moles of nitrate per mole of chromium in the solution and has a copper concentration of from about 0.
    Type: Application
    Filed: August 4, 2006
    Publication date: June 17, 2010
    Inventors: Velliyur Nott Mallikarjuna Rao, H. David Rosenfeld, Allen Sievert, Shekhar Subramoney
  • Publication number: 20100113322
    Abstract: An azeotrope-like composition consisting essentially of 1,1,2,3-tetrachloropropene and hydrogen fluoride is provided, as well as methods that involve such an azeotrope-like composition.
    Type: Application
    Filed: October 28, 2009
    Publication date: May 6, 2010
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: HSUEH S. TUNG, HANG T. PHAM, RAJIV R. SINGH, DANIEL C. MERKEL, ROBERT JOHNSON
  • Publication number: 20100113323
    Abstract: An azeotrope-like composition consisting essentially of 1,1,1,2,3-pentachloropropane and hydrogen fluoride is provided, as well as methods that involve such an azeotrope-like composition.
    Type: Application
    Filed: October 28, 2009
    Publication date: May 6, 2010
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: HSUEH S. TUNG, HANG T. PHAM, RAJIV R. SINGH, DANIEL C. MERKEL
  • Publication number: 20100022809
    Abstract: Disclosed is a method for forming HFO-1234ze, and for forming compositions comprising HFO-1234ze, by (a) converting, preferably by dehydrofluorination, pentafluorpropane (HFC-245), preferably 1,1,1,3,3-pentafluorpropane (HFC-245fa), preferably by contact with a caustic solution, to a reaction product comprising cis-HFO-1234ze and trans-HFO-1234ze; and (b) contacting at least a portion, preferably substantially portion, and in certain embodiments substantially all of said reaction product with at least one isomerization catalyst to convert at least a portion, and preferably at least a substantial portion, of cis-HFO-1234ze in said reaction product to trans-HFO-1234ze.
    Type: Application
    Filed: May 21, 2008
    Publication date: January 28, 2010
    Applicant: HONEYWELL INTERNATIONAL, INC.
    Inventors: Stephen A. Cottrell, Hsueh S. Tung, Haiyou Wang
  • Patent number: 7566809
    Abstract: Process for the separation of a mixture comprising at least one hydrofluoroalkane and hydrogen fluoride, according to which a hydrofluoroalkane/hydrogen fluoride mixture is reacted with at least one chlorinated or chlorofluorinated precursor of the hydrofluoroalkane. Process for the preparation of a hydrofluoroalkane comprising such a separation, in combination with a catalytic reaction stage. Azeotropic compositions.
    Type: Grant
    Filed: May 25, 2007
    Date of Patent: July 28, 2009
    Assignee: Solvay S.A.
    Inventors: Alain Lambert, Vincent Wilmet
  • Publication number: 20080262277
    Abstract: Methods and systems for producing halogenated hydrocarbon compounds with an inorganic fluoride (e.g., germanium tetrafluoride (GeF4)) are disclosed herein.
    Type: Application
    Filed: September 11, 2007
    Publication date: October 23, 2008
    Inventor: Bamidele Omotowa
  • Publication number: 20080262276
    Abstract: Methods and systems for producing hydrofluorocarbon with an inorganic fluoride (e.g., germanium tetrafluoride (GeF4)) are disclosed herein.
    Type: Application
    Filed: September 11, 2007
    Publication date: October 23, 2008
    Inventor: Bamidele Omotowa
  • Publication number: 20080194779
    Abstract: A process is disclosed for the manufacture of CHClF2 which involves contacting CHCl3, HF and pentavalent antimony catalyst in the liquid phase; passing reactor vapor effluent to a reflux column to produce a reflux column vapor effluent of CHClF2 and HCl; passing the reflux column vapor effluent to a condenser to produce a condenser liquid effluent of CHClF2 and a condenser vapor effluent of CHClF2 and HCl; passing the condenser liquid effluent to the reflux column upper end; and recovering CHClF2 from the condenser vapor effluent.
    Type: Application
    Filed: October 15, 2004
    Publication date: August 14, 2008
    Applicant: E.I. DU PONT DE NEMOURS AND COMPANY
    Inventors: Mark John Christmas, Yiannis Nicolas Dimitratos
  • Patent number: 7348461
    Abstract: Methods and materials are provided for the production of essentially isomerically pure perhalogenated and partially halogenated compounds. One embodiment of the present invention provides a process for the production of essentially isomerically pure CFC-216aa. Other embodiments include processes for the production of CFC-217ba and HFC-227ea. Particular embodiments of the present invention provide separation techniques for the separation of chlorofluorocarbons from HF, from other chlorofluorocarbons, and the separation of isomers of halogenated compounds. Still other embodiments of the present invention provide catalytic synthetic techniques that demonstrate extended catalyst lifetime. In other embodiments, the present invention provides catalytic techniques for the purification of isomeric mixtures.
    Type: Grant
    Filed: October 31, 2003
    Date of Patent: March 25, 2008
    Assignee: Great Lakes Chemical Corporation
    Inventors: Yuichi Iikubo, Stephen Owens, Mitchel Cohn, Stephan M. Brandstadter, Vicki E. Hedrick, Janet K. Boggs, John Qian, Julie Sacarias
  • Patent number: 7329786
    Abstract: Methods and materials are provided for the production of essentially isomerically pure perhalogenated and partially halogenated compounds. One embodiment of the present invention provides a process for the production of essentially isomerically pure CFC-216aa. Other embodiments include processes for the production of CFC-217ba and HFC-227ea. Particular embodiments of the present invention provide separation techniques for the separation of chlorofluorocarbons from HF, from other chlorofluorocarbons, and the separation of isomers of halogenated compounds. Still other embodiments of the present invention provide catalytic synthetic techniques that demonstrate extended catalyst lifetime. In other embodiments, the present invention provides catalytic techniques for the purification of isomeric mixtures.
    Type: Grant
    Filed: September 28, 2001
    Date of Patent: February 12, 2008
    Assignee: Great Lakes Chemical Corporation
    Inventors: Yuichi Iikubo, Stephen Owens, Mitchel Cohn, Stephan M. Brandstadter, Vicki E. Hedrick, Janet K. Boggs, John Chengping Chien, Julie Sacarias, Vimal Sharma
  • Patent number: 7223892
    Abstract: Process for the separation of a mixture comprising at least one hydrofluoroalkane and hydrogen fluoride, according to which a hydrofluoroalkane/hydrogen fluoride mixture is reacted with at least one chlorinated or chlorofluorinated precursor of the hydrofluoroalkane. Process for the preparation of a hydrofluoroalkane comprising such a separation, in combination with a catalytic reaction stage. Azeotropic compositions.
    Type: Grant
    Filed: June 28, 2006
    Date of Patent: May 29, 2007
    Assignee: Solvay S.A.
    Inventors: Alain Lambert, Vincent Wilmet
  • Patent number: 7214839
    Abstract: A manufacturing process for making hydrofluorocarbons (HFCs), by reacting a hydrochlorocarbon and HF in a liquid phase catalytic reactor using a large mole ratio of HF to hydrochlorocarbon to minimize formation of high boiling by-products and improve HF consumption and hydrofluorocarbon yields.
    Type: Grant
    Filed: May 23, 2003
    Date of Patent: May 8, 2007
    Assignee: Honeywell International Inc.
    Inventors: Hsueh Sung Tung, Chad L. Marks, Stephen A. Cottrell
  • Patent number: 7109386
    Abstract: Process for the preparation of a halogenated olefin by reaction of an alkyne and/or of an allene compound with a hydrogen halide in a liquid medium comprising at least one hydrohalogenation catalyst comprising at least one palladium compound.
    Type: Grant
    Filed: March 20, 2002
    Date of Patent: September 19, 2006
    Assignee: Solvay (Societe Anonyme)
    Inventor: Véronique Mathieu
  • Patent number: 7094934
    Abstract: In a process for producing a hydrogen-containing fluorinated hydrocarbon in which a halogenated hydrocarbon reaction raw material, which includes a chlorinated alkene and/or a hydrogen-containing chlorinated alkane, is subjected to a fluorination reaction with hydrogen fluoride in a liquid phase in a reactor in the presence of a fluorination catalyst to obtain a reaction mixture which includes the hydrogen-containing fluorinated hydrocarbon, the reactor to be used has a portion which is able to contact with the reaction mixture, at least a part of this portion being made of an alloy material of 18 to 20% by weight of chromium, 18 to 20% by weight of molybdenum, 1.5 to 2.2% by weight of at least one element selected from niobium and tantalum and the balance of nickel.
    Type: Grant
    Filed: January 31, 2001
    Date of Patent: August 22, 2006
    Assignee: Daikin Industries, Ltd.
    Inventors: Noriaki Shibata, Tatsuo Nakada, Takashi Shibanuma
  • Patent number: 7071368
    Abstract: A process for producing 1,1,1-trifluoroethane (HFC-143a) which process comprises reacting hydrogen fluoride with vinylidene chloride along with one or more of 1,1,-dichloro-1-fluoroethane (HCFC-141b), 1-chloro-1,1-difluoroethane (HCFC-142b) and 1,1,1-trichloroethane (HCC-140a) in the presence of pentavalent antimony as a fluorination catalyst under conditions to produce 1,1,1-trifluoroethane (HFC-143a), generally in yields of 90% or more.
    Type: Grant
    Filed: February 9, 2005
    Date of Patent: July 4, 2006
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Hsueh Sung Tung, Robert C. Johnson
  • Patent number: 7038095
    Abstract: A mixture of fluoroalkyl iodide telomers represented by the formula: Rf(CF2CF2)nI wherein Rf represents a fluoroalkyl group whose number of carbon atoms is in the range of 1 to 10, with the polymerization degree n equal to or more than k that is an integer of 3 or more, is obtained by reacting a fluoroalkyl iodide with tetrafluoroethylene in a first reactor followed by fractionating a first reaction mixture which contains fluoroalkyl iodide telomers of low polymerization degree, as well as by reacting the telomer with n of (k?1) separated from the first reaction mixture with tetrafluoroethylene in the second reactor.
    Type: Grant
    Filed: February 5, 2002
    Date of Patent: May 2, 2006
    Assignee: Daikin Industries, Ltd.
    Inventors: Yukio Homoto, Kunitada Tanaka
  • Patent number: 7012165
    Abstract: The subject invention provides methods of fluorinating an aromatic or chloroaromatic compound comprising combining an aromatic compound, a chloroaromatic compound, a mixture of aromatic compounds, a mixture of chloroaromatic compounds, or a mixture of chloroaromatic and aromatic compounds and a fluorinating composition comprising at least one active fluorinating agent selected from the group consisting of CuF2, AgF, HgF2, TeF4, MnF4, FeF3, and CoF2-4 and at least one support selected from the group consisting of activated carbon, ZnF2, CaF2, MgF2, AlF3, and combinations of activated carbon, ZnF2, CaF2, MgF2, or AlF3.
    Type: Grant
    Filed: October 31, 2003
    Date of Patent: March 14, 2006
    Assignee: University of Florida
    Inventors: William R. Dolbier, Jr., Buvaneswari Gopal
  • Publication number: 20040236160
    Abstract: A manufacturing process for making hydrofluorocarbons (HFCs), by reacting a hydrochlorocarbon and HF in a liquid phase catalytic reactor using a large mole ratio of HF to hydrochlorocarbon to minimize formation of high boiling by-products and improve HF consumption and hydrofluorocarbon yields.
    Type: Application
    Filed: May 23, 2003
    Publication date: November 25, 2004
    Applicant: Honeywell International Inc.
    Inventors: Hsueh Sung Tung, Chad L. Marks, Stephen A. Cottrell
  • Publication number: 20040162451
    Abstract: In a process for producing 1,1,1,3,3-pentafluoropropane which has a liquid-phase reaction step for fluorination of 1,1,1,3,3-pentahalopropane (wherein at least one of halogen atoms is not fluorine) with HF in the presence of antimony pentahalide catalyst in a reactor to obtain a reaction mixture comprising 1,1,1,3,3-pentafluoropropane and the antimony pentahalide catalyst, the fluorination is conducted at a reaction temperature less than 50° C.
    Type: Application
    Filed: February 11, 2004
    Publication date: August 19, 2004
    Applicant: Daikin Industries, Ltd.
    Inventors: Tatsuo Nakada, Seiji Takubo, Toshikazu Yoshimura, Takashi Shibanuma
  • Publication number: 20040092781
    Abstract: The present invention relates to a process for preparing polyhaloalkanes and to their use for preparing intermediates for agrochemicals and pharmaceuticals.
    Type: Application
    Filed: November 7, 2003
    Publication date: May 13, 2004
    Inventors: Albrecht Marhold, Axel Pleschke
  • Patent number: 6706935
    Abstract: A method is disclosed for increasing in a composition the mole fraction of a compound selected from the group CF3CHCl2, CF3CHF2 and CF3CHClF relative to the total mole fraction of the other two compounds of the group. The method comprises (a) providing a gaseous composition comprising at least one compound of said group provided that (i) if the selected compound is either CF3CHCl2 or CF3CHF2, said gaseous composition comprises CF3CHFCl and the mole fraction of the selected compound relative to the other two compounds in said gaseous composition is less than its equilibrium amount at 50° C., and (ii) if the selected compound is CF3CHFCl, said gaseous composition comprises both CF3CHCl2 and CF3CHF2 and the mole fraction of the selected compound relative to the other two compounds in said gaseous composition is less than its equilibrium amount at 500° C.
    Type: Grant
    Filed: February 6, 2003
    Date of Patent: March 16, 2004
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Leo Ernest Manzer, Frank Julian Weigert
  • Publication number: 20040024270
    Abstract: A process for the production of a hydrofluoroalkane, which process comprises contacting a hydrochlorofluoroethane of formula CClXYCFHZ, wherein X and Y are each independently chlorine or fluorine and Z is chlorine, fluorine or hydrogen, in the liquid phase with hydrogen fluoride and a fluorination catalyst and recovering a hydrofluoroalkane from the resulting products.
    Type: Application
    Filed: May 13, 2003
    Publication date: February 5, 2004
    Inventors: Clive Robert Giddis, Paul Hendry Stewart
  • Publication number: 20030139634
    Abstract: A method is disclosed for increasing in a composition the mole fraction of a compound selected from the group CF3CHCl2, CF3CHF2 and CF3CHClF relative to the total mole fraction of the other two compounds of the group. The method comprises (a) providing a gaseous composition comprising at least one compound of said group provided that (i) if the selected compound is either CF3CHCl2 or CF3CHF2, said gaseous composition comprises CF3CHFCl and the mole fraction of the selected compound relative to the other two compounds in said gaseous composition is less than its equilibrium amount at 50° C., and (ii) if the selected compound is CF3CHFCl, said gaseous composition comprises both CF3CHCl2 and CF3CHF2 and the mole fraction of the selected compound relative to the other two compounds in said gaseous composition is less than its equilibrium amount at 500° C.
    Type: Application
    Filed: February 6, 2003
    Publication date: July 24, 2003
    Inventors: Leo Ernest Manzer, Frank Julian Weigert
  • Patent number: 6521199
    Abstract: Hydrogen fluoride adducts and ammonium fluorides are used for fluorinating acid chlorides and halocarbon compounds such as chloroalkanes or chloronated ethers. The used adducts can be regenerated and then reused in the fluorination reactions.
    Type: Grant
    Filed: March 4, 2002
    Date of Patent: February 18, 2003
    Assignee: Solvay Fluor und Derivate GmbH
    Inventors: Max Braun, Stefan Palsherm
  • Publication number: 20020183568
    Abstract: The present invention intends to provide a process for producing CF3CF3 with good profitability using CF3CHF2 containing a compound having chlorine atom within the molecule, and use thereof.
    Type: Application
    Filed: January 14, 2002
    Publication date: December 5, 2002
    Inventors: Hiromoto Ohno, Kazunari Kaga, Toshio Ohi
  • Publication number: 20020173681
    Abstract: Hydrogen fluoride adducts and ammonium fluorides are used for fluorinating acid chlorides and halocarbon compounds such as chloroalkanes or chloronated ethers. The used adducts can be regenerated and then reused in the fluorination reactions.
    Type: Application
    Filed: March 4, 2002
    Publication date: November 21, 2002
    Inventors: Max Braun, Stefan Palsherm
  • Patent number: 6479717
    Abstract: A gaseous process for eliminating chlorine atoms from a chlorofluorocarbon (CFC) of formula CnFxCly, wherein n is an integer from 1 to 3 and x+y=2n+2, wherein said compound is reacted with an hydrofluorocarbon of formula Cn′Fx′Hy′, wherein n′, x′, y′ are as above defined, in the presence of a fluorination catalyst in solid phase at temperatures in the range 200° C.-400° C.
    Type: Grant
    Filed: July 17, 2000
    Date of Patent: November 12, 2002
    Assignee: Ausimont S.p.A.
    Inventors: Paolo Cuzzato, Sergio Peron
  • Patent number: 6437200
    Abstract: A gaseous process for obtaining pentafluoroethane by dismutation of chlorotetrafluoroethane in the presence of a supported catalyst, said catalyst being formed of a mixture of trivalent chromium oxide with at least an alkaline-earth metal oxide selected from Mg, Ca, Sr and Ba.
    Type: Grant
    Filed: May 11, 2000
    Date of Patent: August 20, 2002
    Assignee: Ausimont S.p.A
    Inventor: Paolo Cuzzato
  • Patent number: 6417413
    Abstract: A process for preparing halogenated ethanes, particularly pentafluoroethane, from a mixture produced by the reaction of perchloroethylene, hydrogen fluoride and a recycle stream. The preferred process utilizes phase separation techniques to ensure that less than the azzeotropic amount of HF is included in the product stream, thereby minimizing the hydrogen fluoride that is carried off with the desired products after they are separated from the reaction mixture, and at the same time prevents undesirable byproducts from being recycled to the reaction.
    Type: Grant
    Filed: November 3, 1999
    Date of Patent: July 9, 2002
    Assignee: AlliedSignal Inc.
    Inventors: Gustavo Cerri, Yuon Chiu, Biju Z. Perincheril
  • Patent number: 6323379
    Abstract: A process for obtaining pentafluoroethane HFC 125 by dismutation of gaseous tetrafluorochloroethane HCFC 124, at temperatures in the range 200°-300° C., on a trivalent chromium oxide (Cr2O3) catalyst, supported on aluminum fluoride, by feeding HF in such amount that the HCFC 124/HF molar ratio is in the range 10/1-1/1.
    Type: Grant
    Filed: May 11, 2000
    Date of Patent: November 27, 2001
    Assignee: Ausimont S.p.A.
    Inventors: Paolo Cuzzato, Letanzio Bragante, Francesco Rinaldi
  • Patent number: 6300529
    Abstract: Process for preparing HCFC-123 with a content of olefins lower than 10 ppm and very small amounts of HCFC-123a and 123b by dismutation of HCFC-124 in gaseous phase by contact with a catalyst which essentially consists of three valence chromium oxide supported on aluminum fluoride, at temperatures in the range 150°-260° C., and with contact times between 5-25 sec.
    Type: Grant
    Filed: May 26, 1998
    Date of Patent: October 9, 2001
    Assignee: Ausimont S.p.A.
    Inventors: Paolo Cuzzato, Francesco Rinaldi, Letanzio Bragante
  • Patent number: 6274780
    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. The process involves producing the catalyst by heating a single phase solid catalyst precursor having the formula (NH3)6Cr2−xMxF6 (where x is in the range of 0.1 to 1 and M is at least one metal selected from the group consisting of Al, Sc, V, Fe, Ga and In) to about 400° or less to produce a multiphase composition wherein a phase containing crystalline M fluoride is homogeneously dispersed with a phase containing chromium fluoride. Also disclosed are multiphase catalyst compositions consisting essentially of chromium fluoride and a crystalline fluoride of at least one metal selected from the above group (provided the atom percent of Cr is at least equal to the atom percent of the crystalline fluoride metals). Phases of the crystalline fluorides are homogeneously dispersed with phases of the chromium fluoride.
    Type: Grant
    Filed: July 9, 1996
    Date of Patent: August 14, 2001
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: V. N. Mallikarjuna Rao, Munirpallam A. Subramanian
  • Patent number: 6235951
    Abstract: The present invention relates to a method for producing 1,1,1,3,3-pentafluoropropane. This method includes the steps of (a) adding hydrogen fluoride to 1-chloro-3,3,3-trifluoropropene in the presence of an addition catalyst to obtain 1,1,1,3-tetrafluoro-3-chloropropane; and (b) disproportionating the 1,1,1,3-tetrafluoro-3-chloropropane into the 1,1,1,3,3-pentafluoropropane and 1,1,1-trifluoro-3,3-dichloropropane, in the presence of a disproportionation catalyst. This method is a useful method for producing 1,1,1,3,3-pentafluoropropane in an industrial scale, because its steps (a) and (b) are respectively superior in selectivity and yield. 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: November 20, 1996
    Date of Patent: May 22, 2001
    Assignee: Central Glass Company, Limited
    Inventors: Fuyuhiko Sakyu, Satoshi Yoshikawa, Yasuo Hibino, Yoshihiko Gotoh, Ryouichi Tamai
  • Patent number: 6204418
    Abstract: A process is provided for the chlorination of aliphatic hydrocarbons containing 1 to 4 carbon atoms using hydrogen chloride as the source of chlorine. The process comprises reaction steps operated in tandem in separate zones. First, an unsaturated aliphatic fluorocarbon is oxychlorinated to give the corresponding saturated perchlorofluorocarbon and water, and second, the saturated perchlorofluorocarbon is reacted in the vapor phase with a hydrocarbon to produce the desired chlorinated hydrocarbon, hydrogen chloride and the unsaturated aliphatic fluorocarbon, third, hydrogen chloride and unsaturated aliphatic fluorocarbon are separated from the chlorinated hydrocarbon and recycled to the first step, and fourth, the chlorinated hydrocarbon is further purified by subjecting it to addition chlorination to convert traces of unsaturated aliphatic fluorocarbon to the corresponding saturated perchlorofluorocarbon, which is separated and recycled to the second step.
    Type: Grant
    Filed: July 27, 1999
    Date of Patent: March 20, 2001
    Inventor: John E. Stauffer
  • 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: 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: 5841006
    Abstract: Process for preparing pentafluoroethane (125) containing amounts of 115 lower than 0.02% by weight wherein pentafluoroethane is obtained by a dismutation process of tetrafluorochloroethane CF.sub.3 CHClF (HCFC-124) in gaseous phase in the presence of a chrome oxide catalyst (CR.sub.2 O.sub.3) supported on a AlF.sub.3 support, wherein one operates at temperatures from 140.degree.-180.degree. C. for contact times comprised between 15-30 seconds, from >180.degree. C. to 240.degree. C. for contact times between 5 to 15 seconds, from >240.degree. C. to 260.degree. C. for contact times between 1 to 5 seconds, from >260.degree. to 300.degree. C. for contact times between 0.1 to 1 second.
    Type: Grant
    Filed: November 26, 1996
    Date of Patent: November 24, 1998
    Assignee: Ausimont S.p.A.
    Inventor: Paolo Cuzzato
  • Patent number: 5672785
    Abstract: A process for producing 1,1-dichloro-1,2,2,2-tetrafluoroethane, which comprises isomerizing 1,1,2-trichloro-1,2,2-trifluoroethane to form 1,1,1-trichloro-2,2,2-trifluoroethane, followed by fluorination with hydrofluoric acid.
    Type: Grant
    Filed: February 17, 1995
    Date of Patent: September 30, 1997
    Assignee: Asahi Glass Company Ltd.
    Inventors: Shinsuke Morikawa, Shunichi Samejima, Masaru Yoshitake, Shin Tatematsu
  • Patent number: 5600037
    Abstract: 1,1,2-trifluoro-1,2-dichloroethane (Al23a) is isomerized to 1,1,1-tri-fluoro-2,2-dichloroethane (Al23) by contacting it with AlF.sub.3 at temperatures ranging from 180.degree. to 400.degree. C. Advantageously, it is operated with mixtures of Al23a with Al23 and/or other chlorofluorocarbons coming from the preparation of Al23 by hydrofluorination of perchloroethylene.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: February 4, 1997
    Assignee: Ausimont S.p.A.
    Inventors: Paolo Cuzzato, Letanzio Bragante, Antonio Masiero
  • Patent number: 5414167
    Abstract: The 1,1,2-trifluoro-1,2-dichloroethane content is reduced or removed from 1,1,1-trifluoro-2,2-dichloroethane by contacting a gaseous mixture comprising said compounds with chrome oxide (Cr.sub.2 O.sub.3) either as such or supported, at temperatures from 180.degree. to 400.degree. C.
    Type: Grant
    Filed: April 28, 1994
    Date of Patent: May 9, 1995
    Assignee: Ausimont S.p.A.
    Inventors: Letanzio Bragante, Paolo Cuzzato, Antonio Masiero
  • Patent number: 5406009
    Abstract: Gas phase and liquid phase processes are disclosed which use interconversion of CF.sub.3 CHFCl and CF.sub.2 HCF.sub.2 Cl in contact with catalyst consisting essentially of halided aluminum oxide and/or aluminum halide at elevated temperatures to increase the mole ratio of one of said compounds in a composition relative to the other. Also disclosed is use of said interconversion along with hydrogenolysis in processes for producing mixtures of CF.sub.3 CH.sub.2 F and CF.sub.2 HCF.sub.2 H from certain compositions comprising CF.sub.2 HCF.sub.2 Cl such that the mole ratio of CF.sub.3 CH.sub.2 F to CF.sub.2 HCF.sub.2 H in the product mixtures produced from said compositions may be increased or decreased.
    Type: Grant
    Filed: February 28, 1991
    Date of Patent: April 11, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: William H. Manogue, V. N. Mallikarjuna Rao, Frank J. Weigert
  • Patent number: 5345014
    Abstract: Pentafluoroethane (HFC 125) is selectively prepared by dismutation of tetrafluorochloroethane (HCFC 124) effected by contacting the latter, in the gas phase, with a Cr.sub.2 O.sub.3 catalyst at temperatures ranging from 150.degree. to 330.degree. C. Along with HFC 125, also HCFC 123 substantially free from isomers 123a and 123b is obtained.
    Type: Grant
    Filed: May 11, 1993
    Date of Patent: September 6, 1994
    Assignee: Ausimont S.p.A.
    Inventor: Paolo Cuzzato