Antimony Halide Containing Catalyst Patents (Class 570/167)
  • Patent number: 7064240
    Abstract: The process for producing perfluorocarbons according to the present invention is characterized in that in the production of a perfluorocarbon by contacting an organic compound with a fluorine gas, the organic compound is contacted with the fluorine gas at a temperature of from 200 to 500° C. and the content of an oxygen gas within the reaction system is controlled to 2% by volume or less based on the gas components in the reaction starting material, whereby a perfluorocarbon reduced in the content of impurities is produced. According to the process for producing perfluorocarbons of the present invention, high-purity perfluorocarbons extremely suppressed in the production of impurities such as oxygen-containing compound can be obtained. The perfluorocarbons obtained by the production process of the present invention contain substantially no oxygen-containing compound and therefore, can be effectively used as an etching or cleaning gas for use in the process for producing a semiconductor device.
    Type: Grant
    Filed: February 21, 2002
    Date of Patent: June 20, 2006
    Assignee: Showa Denko K.K.
    Inventors: Hiromoto Ohno, Toshio Ohi
  • Patent number: 6930215
    Abstract: 1,1,1,3,3-pentafluoropropane is produced by reaction between 1,1,1,3,3-pentachloropropane and hydrogen fluoride in the presence of a hydrofluorination catalyst. The 1,1,1,3,3-pentachloropropane may advantageously be obtained by reaction between vinyl chloride and tetrachloromethane in the presence of a telomerization catalyst and of a nitrile.
    Type: Grant
    Filed: July 3, 2003
    Date of Patent: August 16, 2005
    Assignee: Solvey (Societe Anonyme)
    Inventors: Vincent Wilmet, Francine Janssens, Jean-Paul Schoebrechts
  • Patent number: 6900362
    Abstract: A process for the production of HFC-227ea from HF and HFP is provided. This process takes advantage of an azeotropic composition of HF and HFC-227ea in order to produce HFC-227ea essentially free of HF and recycle unreacted HF back to the reactor. The recycle of said azeotropic composition, also allows the use of HFC-227ea as a diluent to aid in control of reactor temperature for a highly exothermic reaction.
    Type: Grant
    Filed: October 31, 2002
    Date of Patent: May 31, 2005
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Ralph Newton Miller, Mario J. Nappa, Donald J. Toton
  • Patent number: 6891074
    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: Grant
    Filed: September 3, 2001
    Date of Patent: May 10, 2005
    Assignee: Ineos Fluor Holdings Limited
    Inventors: Clive Robert Giddis, Paul Hendry Stewart
  • Patent number: 6881698
    Abstract: The ionic liquids according to the invention result from the reaction of a halogenated or oxyhalogenated Lewis acid based on titanium, niobium, tantalum, tin or antimony with an organic salt of formula X+A? in which A? is a halide anion and X+ a quaternary ammonium, quaternary phosphonium or ternary sulphonium cation. These liquids can be used in particular in the liquid-phase fluorination using HF of saturated or unsaturated compounds having C—Cl groups.
    Type: Grant
    Filed: April 24, 2001
    Date of Patent: April 19, 2005
    Assignee: Atofina
    Inventors: Phillippe Bonnet, Eric Lacroix, Jean-Pierre Schirmann
  • Patent number: 6858762
    Abstract: A liquid phase process is disclosed for producing halogenated alkane adducts of the formula CAR1R2CBR3R4 (where A, B, R1, R2, R3, and R4 are as defined in the specification) which involves contacting a corresponding halogenated alkane, AB, with a corresponding olefin, CR1R2?CR3R4 in a dinitrile or cyclic carbonate ester solvent which divides the reaction mixture into two liquid phases and in the presence of a catalyst system containing (i) at least one catalyst selected from monovalent and divalent copper; and optionally (ii) a promoter selected from aromatic or aliphatic heterocyclic compounds which contain at least one carbon-nitrogen double bond in the heterocyclic ring. When hydrochlorofluorocarbons are formed, the chlorine content may be reduced by reacting the hydrochlorofluorocarbons with HF. New compounds disclosed include CF3CF2CCl2CH2CCl3, CF3CCl2CH2CH2Cl and CF3CCl2CH2CHClF. These compounds are useful as intermediates for producing hydrofluorocarbons.
    Type: Grant
    Filed: June 12, 2003
    Date of Patent: February 22, 2005
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Ralph Thomas Baker, Ralph Newton Miller, Viacheslav Alexandrovich Petrov, Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
  • Patent number: 6849772
    Abstract: 1,1-Difluoroethane containing less than 10 mg/kg of vinyl chloride is obtained by treatment, with hydrogen fluoride, of a crude 1,1-difluoroethane containing less than 1 mol of hydrogen chloride per mole of 1,1-difluoroethane.
    Type: Grant
    Filed: October 7, 2002
    Date of Patent: February 1, 2005
    Assignee: Solvay (Societe Anonyme)
    Inventors: Charles-Marie Anciaux, Vincent Wilmet, Dominique Lecroc
  • Patent number: 6846963
    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: Grant
    Filed: February 11, 2004
    Date of Patent: January 25, 2005
    Assignee: Daikin Industries, Ltd.
    Inventors: Tatsuo Nakada, Seiji Takubo, Toshikazu Yoshimura, Takashi Shibanuma
  • Patent number: 6841706
    Abstract: Hydrofluorination catalyst based on a chromium oxide which is poor in ammonium salts.
    Type: Grant
    Filed: October 11, 1999
    Date of Patent: January 11, 2005
    Assignee: Solvay (Societe Anonyme)
    Inventors: Vincent Wilmet, Georges Lejeune
  • Patent number: 6841705
    Abstract: A method of producing difluoromethane (HFC-32), which includes firstly reacting methylene chloride with hydrogen fluoride in gas phase at 280 to 340° C. in the presence of a fluorination catalyst to produce chlorofluoro methane, and secondly reacting the chlorofluoro methane with hydrogen fluoride in liquid phase at 60 to 80° C. in the presence of an antimony chloride catalyst. The method is advantageous in that HFC-32 is produced in high yield under mild reaction conditions using a relatively small amount of energy.
    Type: Grant
    Filed: February 24, 2003
    Date of Patent: January 11, 2005
    Assignee: Ulsan Chemical Co., Ltd.
    Inventors: Iikubo Yuichi, Hae Seok Ji, Ook Jae Cho
  • Publication number: 20040171896
    Abstract: Highly fluorinated antimony, especially in the form of a hydrogen fluoride addition compound, can be used as an isomerization catalyst for the isomerization of certain halocarbon compounds or halogenated hydrocarbon compounds. For example, 1,1,1-trifluoro-2,2-dichoroethane can be produced from 1,1,2-trifluoro-1,2-dichloroethane. The method also is suitable for the purification of certain halocarbon or halogenated hydrocarbon compounds which are contaminated by isomerizable compounds.
    Type: Application
    Filed: March 3, 2004
    Publication date: September 2, 2004
    Applicant: Solvay Fluor und Derivate GmbH
    Inventors: Max Braun, Carsten Brosch
  • Patent number: 6755942
    Abstract: The invention relates to azeotropic compositions of halogenated propanes with HF.
    Type: Grant
    Filed: August 14, 2000
    Date of Patent: June 29, 2004
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Ralph Thomas Baker, Ralph Newton Miller, Viacheslav Alexandrovich Petrov, Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
  • Patent number: 6730817
    Abstract: 1,1,1,3,3-Pentafluoropropane is produced by reaction between 1,1,1,3,3-pentachloropropane and hydrogen fluoride in the presence of a hydrofluorination catalyst. The 1,1,1,3,3-pentachloropropane may advantageously be obtained by reaction between vinyl chloride and tetrachloromethane in the presence of a telomerization catalyst and of a nitrile.
    Type: Grant
    Filed: June 8, 1998
    Date of Patent: May 4, 2004
    Assignee: Solvay (Societe Anonyme)
    Inventors: Vincent Wilmet, Francine Janssens, Jean-Paul Schoebrechts
  • Patent number: 6723887
    Abstract: A process for vapor phase fluorination of methylene chloride with anhydrous hydrogen fluoride (AHF) in the presence of a coprecipitated chromia-alumina impregnated with zinc salt as catalyst, removing HCl and heavier components by distillation, subjecting HFC-32 rich cut to a further step of fluorination in the presence of a fluorination catalyst.
    Type: Grant
    Filed: July 12, 2002
    Date of Patent: April 20, 2004
    Assignee: SFR Limited
    Inventors: Rajasekaran Ramanathan, Rajdeep Anand, Anurag Jain, Jampani Madhusudana Rao
  • Patent number: 6720464
    Abstract: Octafluoropropane is produced by a process comprising a step (1) of reacting hexafluoropropene with hydrogen fluoride in a gas phase at a temperature of from 150 to 450° C. in the presence of a fluorination catalyst to obtain 2H-heptafluoropropane and a step (2) of reacting 2H-heptafluoropropane obtained in step (1) with fluorine gas in a gas phase at a temperature of from 250 to 500° C. in the absence of a catalyst to obtain octafluoropropane. High-purity octafluoropropane is obtained which can be used in a process for producing a semiconductor device.
    Type: Grant
    Filed: April 29, 2002
    Date of Patent: April 13, 2004
    Assignee: Showa Denko K.K.
    Inventors: Hiromoto Ohno, Toshio Ohi
  • Publication number: 20040049088
    Abstract: Catalysts which are useful in the fluorination of halogenated hydrocarbons by HF in the gas phase are obtained by simple impregnation of a bulk chromium oxide with a solution of a nickel derivative, the chromium oxide used exhibiting a BET specific surface of greater than 150 m2/g and a pore volume of greater than 0.15 ml/g.
    Type: Application
    Filed: September 10, 2003
    Publication date: March 11, 2004
    Inventors: Eric Lacroix, Jean-Pierre Schirmann
  • Patent number: 6689924
    Abstract: A process for the catalytic fluorination of hydrochlorocarbons and hydrochlorofluorocarbons in the liquid phase. The process is useful for fluorinating hydrochloropropanes, hydrochlorofluoropropanes, hydrochloropropenes and hydrochlorofluoropropenes and most particularly useful for fluorinating 1,1,1,3,3-pentachloropropane to 1,1,1,3,3-pentafloropropane.
    Type: Grant
    Filed: December 20, 1999
    Date of Patent: February 10, 2004
    Assignee: Honeywell International Inc.
    Inventors: Alagappan Thenappan, Hsueh S. Tung, Robert L. Bell
  • Patent number: 6686509
    Abstract: A method for producing an &agr;,&agr;-difluorocycloalkane at high purity with good efficiency, which comprises a step of treating a fluorocycloalkene with hydrogen fluoride wherein the fluorocycloalkene has one fluorine atom directly bonded to a carbon atom of carbon—carbon unsaturated double bond, more preferably, a step of directly adding the hydrogen fluoride to a reaction mixture obtained by treating the cycloalkanone with the de-oxygen fluorinating agent.
    Type: Grant
    Filed: September 24, 2002
    Date of Patent: February 3, 2004
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Kouki Fukumura, Hiroshi Sonoda, Hidetoshi Hayashi, Masahiko Kusumoto
  • Patent number: 6639115
    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: January 18, 2001
    Date of Patent: October 28, 2003
    Assignee: Atofina
    Inventors: Benoit Requieme, Sylvain Perdrieux, Bernard Cheminal, Eric Lacroix, Andre Lantz
  • Patent number: 6635790
    Abstract: The subject of the invention is a continuous process for the manufacture of difluoromethane (F32) from methylene chloride (F30) and hydrogen fluoride in the presence of chlorine, in the gas phase, over a fluorination catalyst. According to the invention, the gas flow exiting from the reactor is subjected to a distillation in order to separate, at the top, a flow containing virtually all the HCl and at least 90% of the F32 produced by the reaction and, at the bottom, a flow containing at least 90% of the unconverted reactants (F31, F30 and HF) and the latter flow is recycled directly to the reactor, without any purification operation.
    Type: Grant
    Filed: January 28, 2000
    Date of Patent: October 21, 2003
    Assignee: Atofina
    Inventors: Dominique Garrait, Emmanuel Guiraud
  • Patent number: 6630610
    Abstract: A process for producing a fluorinated organic compound comprising: (a) reacting an organic starting material with a fluorination agent in the presence of a liquid fluorination catalyst under conditions which are effective to vaporize one or more chlorinated organic by-products and to produce a gaseous product stream containing said fluorinated organic compound and said one or more chlorinated organic by-products; and (b) recovering said fluorinated organic compound from said product stream, and a system for performing the aforementioned process and recovering the chlorinated by-product.
    Type: Grant
    Filed: March 6, 2001
    Date of Patent: October 7, 2003
    Assignee: AlliedSignal Inc.
    Inventors: Charles F. Swain, Stephen A. Cottrell, Clifford Scott Riegel, Curtis A. Brescher
  • Patent number: 6596910
    Abstract: Disclosed is an improved HFC manufacturing processes of the type which produces an intermediate product stream that includes a mixture of HF and at least one compound, usually an HCFC, which is relatively resistant to further fluorination. The improvement involves separating the unreactive compound(s) from the product stream, preferably using liquid:liquid phase separation, and substantially avoiding recycle of the unreactive compound to the fluorination reaction. The separated unreactive compound(s) are substantially free of HF.
    Type: Grant
    Filed: January 25, 2002
    Date of Patent: July 22, 2003
    Assignee: Honeywell International Inc.
    Inventors: Hsueh Sung Tung, Clayton Herbert Carson, Hang Thanh Pham
  • Patent number: 6548712
    Abstract: The invention relates to a process for producing 1,1,1,5,5,5-hexafluoroacetylacetone. This process includes (a) hydrolyzing a metal complex of 1,1,1,5,5,5-hexafluoroacetylacetone into a 1,1,1,5,5,5-hexafluoroacetylacetone hydrate; and (b) dehydrating the hydrate into the 1,1,1,5,5,5-hexafluoroacetylacetone with high purity from a material containing a metal complex of 1,1,1,5,5,5-hexafluoroacetylacetone.
    Type: Grant
    Filed: March 15, 2001
    Date of Patent: April 15, 2003
    Assignee: Central Glass Company, Limited
    Inventors: Takeo Komata, Nariaki II
  • Patent number: 6538165
    Abstract: According to a process for producing difluoromethane and difluorochloromethane, which comprises fluorinating dichloromethane and trichloromethane with hydrogen fluoride in a liquid phase in the presence of a catalyst in one reaction apparatus under the conditions that a reaction pressure is from 1 to 20 kg/cm2 and a reaction temperature is from 50 to 150° C., difluoromethane and difluorochloroethane can be simultaneously or alternatively produced in an economical/safe manner by one reaction apparatus.
    Type: Grant
    Filed: August 8, 1997
    Date of Patent: March 25, 2003
    Assignee: Daikin Industries Ltd.
    Inventors: Takehide Tsuda, Takashi Shibanuma
  • Patent number: 6528691
    Abstract: A gas phase process for the preparation of 245fa is provided, wherein 1233zd is contacted with HF in the presence of a supported antimony catalyst.
    Type: Grant
    Filed: May 14, 1999
    Date of Patent: March 4, 2003
    Assignee: Atofina Chemicals, Inc.
    Inventors: Maher Y. Elsheikh, Bin Chen
  • Patent number: 6521802
    Abstract: The present invention provides a process for preparing a fluorine-containing halogenated hydrocarbon compound by fluorinating, in a reaction field where an antimony halide compound represented by the general formula: SbClpF5−p  (I) wherein p is a value within a range from 0 to 2, and hydrogen fluoride and a halogenated hydrocarbon compound as a raw material exist, the halogenated hydrocarbon compound in a molar ratio of the antimony halide compound to hydrogen fluoride within a range from 40/60 to 90/10. According to this process, a fluorine-containing halogenated hydrocarbon compound (HFC), which is important as a substitute compound of CFC or HCFC, can be prepared economically advantageously with good selectivity while suppressing a corrosive action of a reaction vessel.
    Type: Grant
    Filed: May 29, 2002
    Date of Patent: February 18, 2003
    Assignee: Daikin Industries, Ltd.
    Inventors: Seiji Takubo, Noriaki Shibata, Tatsuo Nakada, Takashi Shibanuma
  • Patent number: 6479718
    Abstract: An improved liquid phase process is provided for the fluorination of perchloroethylene to 1,1-dichloro-2,2,2-trifluoroethane in the presence of an antimony catalyst.
    Type: Grant
    Filed: March 28, 2002
    Date of Patent: November 12, 2002
    Assignee: Atofina Chemicals, Inc.
    Inventors: Maher Y. Elsheikh, Jonathan M. Tracy, John A. Wismer
  • Patent number: 6472573
    Abstract: A method of preparation for 1,1,1,3,3-pentafluoropropane (HFC-245fa) wherein the first process gives mainly 1,3,3,3-tetrafluoropropene (1234ze) by reacting 1-chloro-3, 3,3,-trifluoropropene (1233zd) with hydrogen fluoride in the gas phase and subsequently the second process gives 1,1,1,3,3-pentafluoropropane (HFC-245fa) by reacting 1,3,3,3-tetrafluoropropene (1234ze), separated as a component that does not contain hydrogen chloride from crude products obtained by the first process, with hydrogen fluoride in the gas phase. To provide a process that is capable of preparing economically HFC-245fa which does not require the separation of HFC-245fa and 1233zd.
    Type: Grant
    Filed: August 2, 2000
    Date of Patent: October 29, 2002
    Assignee: Daikin Industries, Ltd.
    Inventors: Akinori Yamamoto, Noriaki Shibata, Tatsuo Nakada, Takashi Shibanuma
  • Patent number: 6437201
    Abstract: An improved process for the manufacture of CF3CHF2 by contacting 1,2-dichloro-1,1,2-trifluoroethane (CClF2CHClF) or 1-chloro-1,1,2,2-tetrafluoroethane (CHF2CClF2) or mixtures of CF3CHCl2 and CClF2CHClF or mixtures of CF3CHClF and CHF2CClF2 with HF in the presence of a Cr2O3 catalyst prepared by pyrolysis of ammonium dichromate, the reaction being conducted under controlled conditions whereby the production of CF3CHF2 is maximized, and the formation of chloropentafluoroethane (CF3CClF2) and other perhalo derivatives is minimized. The subject hydrogen-containing compound is useful as a blowing agent, propellant, refrigerant, fire extinguishing agent, or sterilant carrier gas.
    Type: Grant
    Filed: April 24, 1997
    Date of Patent: August 20, 2002
    Assignee: Ineos Fluor Holdings Limited
    Inventors: Paul Nicholas Ewing, Richard Llewellyn Powell, Michael Anthony Davies, Christopher John Skinner
  • Patent number: 6407296
    Abstract: A process is disclosed for producing difluoromethane by fluorinating dichloromethane with hydrogen fluoride in a liquid phase in the presence of a catalyst, wherein the reaction is conducted at a temperature within the range from 80 to 150° C. under a pressure within the range from 8 to 80 kg/cm2 using a mixture of antimony pentafluoride and antimony trifluoride, or antimony pentafluoride as the fluorinating catalyst. The process economically and safely produces difluoromethane from dichloromethane and hydrogen fluoride.
    Type: Grant
    Filed: December 23, 1996
    Date of Patent: June 18, 2002
    Assignee: Daikin Industries Ltd.
    Inventors: Yasufu Yamada, Takashi Shibanuma, Takehide Tsuda
  • Patent number: 6403847
    Abstract: One or more materials selected from 1,1,1,3,3-pentachloropropane, 1,1,3,3-tetrachloropropene and 1,3,3,3-tetrachloropropene are used as the specific materials described above. Before submitting the materials and HF to a fluorination reaction, almost all water is removed from them. To continuously manufacture useful intended products efficiently as well as to prevent deactivation of the catalyst and the accumulation of organic substances with high boiling points when manufacturing said useful 1,1,1,3,3-pentafluoropropane and/or 1-chloro-3,3,3-trifluoropropene, by fluorinating the specific materials with HF in the presence of a catalyst.
    Type: Grant
    Filed: March 20, 2001
    Date of Patent: June 11, 2002
    Assignee: Daikin Industries Ltd.
    Inventors: Tatsuo Nakada, Takashi Shibanuma, Noriaki Shibata
  • Patent number: 6392106
    Abstract: A process for producing 1,1,1,2,2-pentafluoroethane by fluorinating with hydrogen fluoride at least one of 2,2-dichloro-1,1,1-trifluoroethane and 2-chloro-1,1,1,2-tetrafluoroethane as a starting material, the process being characterized by separating the reaction mixture resulting from the fluorination into a product portion A mainly containing 1,1,1,2,2-pentafluoroethane and a product portion B mainly containing 2,2-dichloro-1,1,1-trifluoroethane, 2-chloro-1,1,1,2-tetrafluoroethane and hydrogen fluoride, removing a fraction mainly containing 2,2-dichloro-1,1,1,2-tetrafluoroethane from the product portion B, and recycling the rest of the product portion B as part of feedstocks for fluorination. According to the process of the invention, the amount of CFC-115 contained in the target HFC-125 can be remarkably reduced through a simplified procedure.
    Type: Grant
    Filed: April 5, 2000
    Date of Patent: May 21, 2002
    Assignee: Daikin Industries, Ltd.
    Inventors: Satoru Kono, Toshikazu Yoshimura, Takashi Shibanuma
  • Patent number: 6369285
    Abstract: Halohydrocarbons containing at least 3 carbon atoms are obtained by reaction between a haloalkane and an olefin in the presence of a catalyst in a reaction medium which is essentially free of water.
    Type: Grant
    Filed: September 29, 2000
    Date of Patent: April 9, 2002
    Assignee: Solvay (Societe Anonyme)
    Inventors: Véronique Mathieu, Charles-Marie Anciaux
  • Patent number: 6362383
    Abstract: Improved process for the catalytic hydro-fluorination of saturated or unsaturated organic compounds corresponding to the general formula CwHxClyFz (I) in which w is an integer between 1 and 6, x is an integer between 0 and (2w+1) or between 0 and (2w−1), y is an integer between 1 and (2w+1) or between 1 and (2w−1), z is an integer between 0 and (2w+1) or between 0 and (2w−1) and the sum (x+y+z) is equal to (2w+2), comprising a continuous feed of hydrogen chloride. Process for preparing 1,1,1,3,3-pentafluoropropane starting with 1,1,1,3,3-pentachloropropane, comprising two catalytic reaction steps, in which hydrogen chloride is preferably fed continuously into the reaction medium of at least one of the two reaction steps.
    Type: Grant
    Filed: September 29, 2000
    Date of Patent: March 26, 2002
    Assignee: Solvay (Societe Anonyme)
    Inventors: Vincent Wilmet, Francine Janssens
  • Patent number: 6350926
    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 vapour phase. The product has useful solvent properties and is also useful in synthetic chemistry for the introduction of fluorocarbon functionality.
    Type: Grant
    Filed: December 14, 1999
    Date of Patent: February 26, 2002
    Assignee: Syngenta Limited
    Inventor: Alfred Glyn Williams
  • Patent number: 6339178
    Abstract: The subject of the invention is the manufacture of 1,1,1-trifluoroethane by fluorination or 1-chloro-1,1-difluoroethane with anhydrous hydrofluoric acid. The reaction is carried out in the liquid phase and in the presence of a fluorination catalyst.
    Type: Grant
    Filed: June 22, 2000
    Date of Patent: January 15, 2002
    Assignee: Atofina
    Inventors: Andre Lantz, Sylvain Perdrieux, Dominique Garrait, Laurent Wendlinger
  • Patent number: 6329559
    Abstract: A process is disclosed for the manufacture of CF3CF═CF2, and optionally a least one compound selected from CF3CH2CF3 and CF3CHFCHF2. The process involves contacting a reactor feed including a precursor stream of at least one halogenated propane of the formula CX3CH2CHyX(3−y) and/or halogenated propene of the formula CX3CH═CHyX(2−y), where each X is Cl or F and y is 0, 1 or 2 (provided that the average fluorine content of the precursor stream is no more than 5 fluorine substituents per molecule) with HF and Cl2 in a chlorofluorination reaction zone containing a fluorination catalyst and operating at a temperature between about 150° C. and 400° C.
    Type: Grant
    Filed: November 27, 2000
    Date of Patent: December 11, 2001
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Allen Capron Sievert, V. N. Mallikarjuna Rao, Francis J. Walczak
  • Patent number: 6329560
    Abstract: A method for producing a hydrogen-containing fluorinated hydrocarbon includes supplying HF to a gap between an inner reactor made of a material resistant to the reaction and an outer container made of a material resistant to HF; supplying HF to the inner reactor; supplying a halogenated hydrocarbon selected from a chlorinated alkene and a hydrogen-containing chlorinated alkane to the inner reactor; and reacting HF with halogenated hydrocarbon in the presence of a fluorination catalyst in the inner reactor to obtain the reaction product containing the hydrogen-containing fluorinated hydrocarbon.
    Type: Grant
    Filed: January 12, 2001
    Date of Patent: December 11, 2001
    Assignee: Daikin Industries, Ltd.
    Inventors: Tatsuo Nakada, Noriaki Shibata, Takashi Shibanuma
  • 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: 6291728
    Abstract: A manufacturing method for 1,1,1,3,3-pentafluoropropane, wherein 1,1,1,3,3-pentafluoropropane (HFC-245fa) is obtained by reacting halogenated propane, for example, 1,1,1,3,3-pentachloropropane and so on, which is represented by the general formula: CX3CH2CHX2 [In the general formula, X is fluorine atom (F) or chlorine atom (Cl), and all of X can not be fluorine atoms at the same time], with anhydrous hydrofluoric acid (HF) under the presence of antimony catalyst. HFC-245fa can be obtained with high yield and economical advantages through simple process.
    Type: Grant
    Filed: March 27, 1998
    Date of Patent: September 18, 2001
    Assignee: Daikin Industries, Ltd.
    Inventors: Hirokazu Aoyama, Tatsuo Nakada, Akinori Yamamoto
  • 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: 6268540
    Abstract: The present invention provides catalysts and processes for the fluorination of hydrohalomethanes. In particular, the invention provides a process for the fluorination of hydrohalomethanes using hydrogen fluoride and a Lewis Acid catalyst. More specifically, catalysts and a process for the fluorination of dichloromethane are provided.
    Type: Grant
    Filed: June 24, 1996
    Date of Patent: July 31, 2001
    Assignee: AlliedSignal Inc.
    Inventors: Alagappan Thenappan, Addison Miles Smith, Jeffrey Warren McKown, Robert Louis Bell
  • 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: 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: 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: 6165426
    Abstract: Disclosed is a method of removing a soluble antimony compound from a liquid in which it is dissolved. The liquid is contacted with a hydrated compound, particularly a hydrated compound that forms carbonate ions, bicarbonate ions, or both in the liquid, such as carbonic acid or hydrates of sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, ammonium carbonate, or ammonium bicarbonate. An antimony compound is formed that is insoluble in the liquid and it is separated from the liquid.
    Type: Grant
    Filed: July 16, 1999
    Date of Patent: December 26, 2000
    Assignee: Occidental Chemical Corporation
    Inventor: Sanjay K. Mandal
  • 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: 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