Utilizing Unsaturated Compound Patents (Class 570/175)
  • Patent number: 7786333
    Abstract: A process for the production of fluorinated olefins, preferably fluorinated propenes, by contacting a feed stream containing a fluorinated olefin and hydrogen with a first amount of catalyst to produce the hydrofluorocarbon, wherein a first exit stream contains unreacted fluorinated olefin and hydrogen; contacting the first exit stream with a second amount of catalyst to produce a hydrofluorocarbon, wherein the second amount of catalyst is preferably greater than the first amount of catalyst; and contacting the hydrofluorocarbon with a catalyst for dehydrohalogenation to produce a product stream of fluorinated olefin.
    Type: Grant
    Filed: February 19, 2009
    Date of Patent: August 31, 2010
    Assignee: Honeywell International, Inc.
    Inventors: Michael Van Der Puy, George R. Cook, Peter H. Sheidle, Kevin D. Uhrich, Haiyou Wang, Hsueh Sung Tung
  • Patent number: 7759532
    Abstract: The present invention relates to compositions and processes of using perfluoropolyether to maintain or improve the oil return, lubrication, cooling capacity, or energy efficiency of a refrigeration, air conditioning or heat transfer system.
    Type: Grant
    Filed: July 11, 2007
    Date of Patent: July 20, 2010
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Thomas J. Leck, Thomas Frank Saturno, Gregory A. Bell
  • Publication number: 20100137658
    Abstract: Provided is a process for making 2-chloro-1,1,1,2-tetrafluoropropane. The process has the step of hydrofluorinating 2-chloro-3,3,3-trifluoropropene in the presence of a catalyst selected from the group consisting of SbCl3, SbCl5, SbF5, TiCl4, SnCl4, Cr2O3, and fluorinated Cr2O3.
    Type: Application
    Filed: December 4, 2009
    Publication date: June 3, 2010
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Daniel C. Merkel, Robert C. Johnson, Hsueh Sung Tung
  • Patent number: 7678949
    Abstract: A process for the manufacture of CF3CH?CHF and/or CF3CF?CH2 is disclosed. The process involves (a) reacting HF and chlorine and at least one halopropene of the formula CX3CCI?CCIX (where each X is independently F or Cl) to produce a product including both CF3CCI2CCIF2 and CF3CCIFCCI2F; (b) reacting CF3CCI2CCIF2 and CF3CCIFCCI2F produced in (a) with hydrogen to produce a product including both CF3CH2CHF2 and CF3CHFCH2F; (c) dehydrofluorinating CF3CH2CHF2 and CF3CHFCH2F produced in (b) to produce a product including both CF3CH?CHF and CF3CF?CH2; and (d) recovering CF3CH?CHF and/or CF3CF?CH2 from the product produced in (c). In (a), both CF3CCI2CCIF2 and CF3CCIFCCI2F are produced in the presence of a chlorofluorination catalyst consisting of (i) compositions comprising a crystalline alpha-chromium oxide where at least 0.05 atom % of the chromium atoms in the alpha-chromium oxide lattice are replaced by copper, and (ii) compositions of (i) which have been treated with a fluorinating agent.
    Type: Grant
    Filed: August 4, 2006
    Date of Patent: March 16, 2010
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Velliyur Nott Mallikarjuna Rao, H. David Rosenfeld, Allen Capron Sievert, Shekhar Subramoney
  • Patent number: 7663007
    Abstract: A process for the manufacture of CF3CH?CHF and/or CF3CH?CF2 is disclosed. The process involves (a) reacting HF and at least one halopropene of the formula CX3CCI?CCIX (where each X is independently F or CI) to produce a product including both CF3CCI?CF2 and CF3CHCICF3; (b) reacting CF3CCI?CF2 and/or CF3CHCICF3 produced in (a) with hydrogen to produce a product including CF3CH2CHF2 and/or CF3CH2CF3; (c) dehydrofluorinating CF3CH2CHF2 and/or CF3CH2CF3 produced in (b) to produce a product comprising CF3CH?CHF and/or CF3CH?CF2; and (d) recovering CF3CH?CHF and/or CF3CH?CF2 from the product produced in (c). In (a), the CF3CCI?CF2 and CF3CHCICF3 are produced in the presence of a fluorination catalyst comprising at least one chromium-containing component selected from (i) a crystalline alpha-chromium oxide where at least 0.
    Type: Grant
    Filed: August 4, 2006
    Date of Patent: February 16, 2010
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Velliyur Nott Mallikarjuna Rao, H. David Rosenfeld, Allen Capron Sievert, Shekhar Subramoney
  • Publication number: 20090227821
    Abstract: The present invention provides a novel method for preparing 4,4,4-trifluorobutane-2-one by providing a fluorobutene selected from the group consisting of 2,4,4,4-tetrafluoro-1-butene, (E)-1,1,1,3-tetrafluoro-2-butene, (Z)-1,1,1,3-tetrafluoro-2-butene, and mixture thereof; and reacting the fluorobutene(s) with a proton acid and water.
    Type: Application
    Filed: October 18, 2004
    Publication date: September 10, 2009
    Applicant: CENTRAL GLASS CO., LTD.
    Inventors: Adam Alty, Frank Waters, Richard Du Boisson, Yokusu Kuriyama, Masamichi Maruta
  • Publication number: 20090216054
    Abstract: Disclosed is a process for producing 1,2,3,4-tetrachlorohexafluorobutane safely in a high yield in the industrial viewpoint and at low cost in the economical viewpoint. Specifically disclosed is a process for producing 1,2,3,4-tetrachlorohexafluorobutane which process comprises: (1) a step of chlorinating 1,3-butadiene, thereby preparing a mixture containing 1,2,3,4-tetrachlorobutane, and (2) a step of allowing the 1,2,3,4-tetrachlorobutane prepared in the step (1) to react with a fluorine gas in the presence of a diluting gas in a gas phase, thereby preparing a mixture containing 1,2,3,4-tetrachlorohexafluorobutane.
    Type: Application
    Filed: April 25, 2007
    Publication date: August 27, 2009
    Applicant: SHOWA DENKO K.K.
    Inventors: Hiromoto Ohno, Toshio Ohi
  • 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: 20090131727
    Abstract: A process for producing hydrofluorocarbon compounds represented by the following formula: CF3CHFCHm+1Fn wherein m is 0 or 2; n is 0 or 2; and m+n=2. The process has the step of contacting, i.e., reacting, hydrogen with a precursor compound represented by the following formula: CF3CF?CHmFn wherein m is 0 or 2; n is 0 or 2; and m+n=2. The contact is carried out in the presence of a solid catalyst and in the presence or absence of an inert gas. The catalyst is selected from the group consisting of: Fe, Co, Ni, Cu, Cr, Ru, Rh, Ag, Re, Os, Ir, Pt, Au, Sn, and any combinations thereof. For the hydrogenation of 1234yf to 254eb, Pd can also be used as catalyst in addition to the other above-referenced metals. These metals are preferably supported on a carrier such as activated carbon.
    Type: Application
    Filed: November 4, 2008
    Publication date: May 21, 2009
    Inventors: Shuwu Yang, Hsueh Sung Tung
  • Publication number: 20080269532
    Abstract: Disclosed is a method for the synthesis of fluorinated alkenes comprising contacting a fluorinated alkyne of the formula R1 C?C R2, wherein R1 and R2 are independently selected from CF3, C2F5, C3F7, and C4F9, in a pressure vessel, with a Lindlar catalyst, with substantially one molar equivalent of hydrogen, to make the corresponding cis-alkene of formula R1 C?C R2 with high selectivity, wherein said hydrogen is added in portions over a period of time, so as to produce an initial pressure in the pressure in the vessel of no more than about 100 psi.
    Type: Application
    Filed: April 28, 2008
    Publication date: October 30, 2008
    Applicant: E. I. DU PONT DE NEMOURS AND COMPANY
    Inventor: Ekaterina N. SWEARINGEN
  • Publication number: 20080207963
    Abstract: A method for preparing a catalyst composition suitable for increasing the fluorine content in a hydrocarbon or a halogenated hydrocarbon is disclosed. The method involves (a) co-precipitating a solid by adding ammonium hydroxide to an aqueous solution of a soluble trivalent chromium salt and a soluble salt of a modifier metal selected from silver and palladium, that contains at least three moles of nitrate (i.e., NO3?) per mole of chromium (i.e., Cr+3) in the solution and has a modifier metal concentration of from about 0.05 atom % to about 10 atom % of the total concentration of modifier metal and chromium in the solution to form an aqueous mixture containing co-precipitated solid and dissolved ammonium nitrate; and after at least three moles of ammonium hydroxide per mole of chromium in the solution has been added to the solution, (b) drying said aqueous mixture formed in (a); and (c) calcining the dried solid formed in (b) in an atmosphere containing at least 10% oxygen by volume (e.g., air).
    Type: Application
    Filed: February 21, 2008
    Publication date: August 28, 2008
    Inventors: Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
  • Publication number: 20080191163
    Abstract: Disclosed herein are laser cutting/etching assist fluids and methods of use thereof. The compounds include unsaturated fluorocarbons appropriate for use in laser assist applications.
    Type: Application
    Filed: February 5, 2008
    Publication date: August 14, 2008
    Inventor: Michael T. Mocella
  • 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: 7345209
    Abstract: Disclosed is a process for the synthesis of 1,3,3,3-tetrafluoropropene that comprises, in one preferred embodiment, providing a compound of the formula CF3CH2CHFX, wherein X is a selected from the group consisting of chlorine, bromine and iodine, and exposing said compound to reaction conditions effective to convert said compound to 1,3,3,3-tetrafluoropropene. Other processes for forming 1,3,3,3-tetrafluoropropene are also disclosed.
    Type: Grant
    Filed: April 29, 2005
    Date of Patent: March 18, 2008
    Assignee: Honeywell International Inc.
    Inventors: Sudip Mukhopadhyay, Haridasan K. Nair, Hsueh S. Tung, Michael Van Der Puy
  • Patent number: 7285691
    Abstract: A process is disclosed for the manufacture of 1,1,1,3,3,3-hexafluoropropane (HFC-236fa) and at least one 1,1,1,2,3,3-hexafluoropropane (HFC-236ea) and 1,1,1,2,3,3,3-heptafluoropropane (HFC-227ea). The process involves (a) reacting HF, Cl2, and at least one halopropene of the formula CX3CCl=CX2 (where each X is independently F or Cl) to produce a product including both CF3CCl2CF3 and CF3CClFCClF2; (b) reacting CF3CCl2CF3 and CF3CClFCClF2 produced in (a) with hydrogen to produce a product comprising CF3CH2CF3 and at least one compound selected from the group consisting of CHF2CHFCF3, and CF3CHFCF3; and (c) recovering from the product produced in (b), CF3CH2CF3 and at least one compound selected from the group consisting of CHF2CHFCF3 and CF3CHFCF3.
    Type: Grant
    Filed: October 13, 2004
    Date of Patent: October 23, 2007
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Velliyur Nott Mallikarjuna Rao, Allen C. Sievert
  • Patent number: 7285692
    Abstract: A process is disclosed for the manufacture of CF3CH2CHF2 and CF3CHFCH2F. The process involves (a) reacting hydrogen fluoride, chlorine, and at least one halopropene of the formula CX3CCl?CClX (where each X is independently F or Cl) to produce a product including both CF3CCl2CClF2 and CF3CClFCCl2F; (b) reacting CF3CCl2CClF2 and CF3CClFCCl2F produced in (a) with hydrogen to produce a product including both CF3CH2CHF2, and CF3CHFCH2F; and (c) recovering CF3CH2CHF2 and CF3CHFCH2F from the product produced in (b). In (a), the CF3CCl2CClF2 and CF3CClFCCl2F are produced in the presence of a chlorofluorination catalyst including a ZnCr2O4/crystalline ?-chromium oxide composition, a ZnCr2O4/crystalline ?-chromium oxide composition which has been treated with a fluorinating agent, a zinc halide/?-chromium oxide composition and/or a zinc halide/?-chromuim oxide composition which has been treated with a fluorinating agent.
    Type: Grant
    Filed: October 13, 2004
    Date of Patent: October 23, 2007
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Velliyur Nott Mallikarjuna Rao, Allen C. Sievert
  • Patent number: 7285690
    Abstract: A process for the manufacture of CF3CH2CHF2 and CF3CH2CF3 is disclosed. The process involves (a) reacting HF and at least one halopropene of the formula CX3CCI=CCIX (where each X is independently F or CI) to produce a product including both CF3CCI=CF2 and CF3CHCICF3; (b) reacting CF3CCI=CF2 and CF3CHCICF3 produced in (a) with hydrogen to produce a product including both CF3CH2CHF2 and CF3CH2CF3; and (c) recovering CF3CH2CHF2 and CF3CH2CF3 from the product produced in (b). In (a), the CF3CCI=CF2 and CF3CHCICF3 are produced in the presence of a fluorination catalyst including a ZnCr2O4/crystalline ?-chromium oxide composition, a ZnCr2O4/crystalline ?-chromium oxide composition which has been treated with a fluorinating agent, a zinc halide/?-chromium oxide composition and/or a zinc halide/?-chromium oxide composition which has been treated with a fluorinating agent.
    Type: Grant
    Filed: October 13, 2004
    Date of Patent: October 23, 2007
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Velliyur Nott Mallikarjuna Rao, Allen C. Sievert
  • 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: 7145046
    Abstract: Inorganic and organic compounds containing fluorine can be produced, for example, from corresponding chlorine-containing compounds by chlorine/fluorine exchange using fluorinating agents. Monocyclic or bicyclic compounds containing at least two nitrogen atoms, at least one of which is incorporated into the ring system, can be used as catalysts or fluorinating agents for chlorine/fluorine exchange reactions to produce sulfurylchlorofluoride, sulfurylfluoride or a carboxylic acid fluoride. It is likewise possible to carry out HF addition to unsaturated carbon-carbon bonds or chlorine/fluorine exchange at carbon atoms. For example, monochloro or dichloro malonic acid esters can be converted to difluoro malonic acid esters. Work-up of the reaction mixture can be simplified by using suitable solvents which force the reaction mixture to exist in two phases.
    Type: Grant
    Filed: August 1, 2003
    Date of Patent: December 5, 2006
    Assignee: Solvay Fluor und Derivate GmbH
    Inventors: Max Braun, Carsten Brosch
  • Patent number: 7094936
    Abstract: Methods and materials are provided for the production and purification of halogenated compounds and intermediates in the production of 1,1,1,3,3-pentafluoropropane. In a preferred embodiment, the process steps include: (1) reacting carbon tetrachloride with vinyl chloride to produce 1,1,1,3,3-pentachloropropane; (2) dehydrochlorinating the 1,1,1,3,3-pentachloropropane with a Lewis acid catalyst to produce 1,1,3,3-tetrachloropropene; (3) fluorinating the 1,1,3,3-tetrachloropropene to produce 1-chloro-3,3,3-trifluoropropene; (4) fluorinating the 1-chloro-3,3,3-trifluoropropene to produce a product mixture containing 1,1,1,3,3-pentafluoropropane; and (5) separating 1,1,1,3,3-pentafluoropropane from by-products.
    Type: Grant
    Filed: October 16, 2003
    Date of Patent: August 22, 2006
    Assignee: Great Lakes Chemical Corporation
    Inventors: Stephen Owens, Andrew Jackson, Vimal Sharma, Mitchel Cohn, John Cheng-Ping Qian, Julia Ann Sacarias, Yuichi Iikubo
  • Patent number: 7067707
    Abstract: Process for the manufacture of pentafluoroethane, according to which tetrafluoroethylene is subjected to reaction with an organic nitrogenous base hydrofluoride at a temperature of greater than 100° C. and not exceeding 160° C.
    Type: Grant
    Filed: August 22, 2003
    Date of Patent: June 27, 2006
    Assignee: Solvay (Societe Anonyme)
    Inventors: Eberhard Piepho, Vincent Wilmet, Olivier Buyle
  • Patent number: 7053253
    Abstract: Perfluoro-4-methyl-2-pentene containing the undesirable perfluoro-2-methyl-2-pentene may be purified by contacting the mixture with at least a stoichiometric equivalent of an aqueous inorganic base (relative to the perfluoro-2-methyl-2-pentene), in the presence of a polar solvent.
    Type: Grant
    Filed: May 2, 2005
    Date of Patent: May 30, 2006
    Assignee: 3M Innovative Properties Company
    Inventors: Zhongxing Zhang, Zai-Ming Qiu
  • Patent number: 7041859
    Abstract: A method for obtaining a halogenated organic compound, whereby an organotrifluoroborate compound is reacted with a halide ion in the presence of an oxidizing agent to produce the corresponding halogenated organic compound. The method may be used for producing radiohalogenated organic compounds.
    Type: Grant
    Filed: July 5, 2005
    Date of Patent: May 9, 2006
    Assignee: University of Tennessee Research Foundation
    Inventor: George W. Kabalka
  • 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: 6992229
    Abstract: The present invention has an object to provide a method for purifying a fluorinated hydroxyl compound of the formula 1 safely in a high yield under industrially practical conditions. Namely, a mixture containing a fluorinated hydroxyl compound of Rf—CR1R2—OH (Formula 1, wherein Rf is a C1-20 polyfluoroalkyl group, and each of R1 and R2 is a hydrogen atom or a C1-3 alkyl group) such as 2,2,3,3-tetrafluoropropanol, and a compound having an unshared electron pair, is distilled by heating in the presence of a solid acid catalyst such as a cation exchange resin catalyst, or by adding a proton source such as water.
    Type: Grant
    Filed: November 19, 2002
    Date of Patent: January 31, 2006
    Assignee: Asahi Glass Company, Limited
    Inventors: Hidekazu Okamoto, Akihiro Wada, Toshihiko Toma, Nobuyuki Yamagishi
  • Patent number: 6958422
    Abstract: The present invention relates to the pyrolysis of hydrochlorofluorocarbons to form fluoromonomers such as tetrafluoroethylene, the pyrolysis being carried out in a reaction zone lined with nickel and mechanically supported by a jacket of other corrosion resistant metal, the nickel lining providing an improved yield of valuable reaction products.
    Type: Grant
    Filed: December 17, 2003
    Date of Patent: October 25, 2005
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Charles Joseph Noelke, Velliyur Nott Mallikarjuna Rao
  • Patent number: 6946582
    Abstract: The present invention provides a process for producing a fluoroalkyl iodide represented by the general formula (II): Rf-CH2CH2I??(II) wherein Rf is a perfluoroalkyl or polyfluoroalkyl group comprising 1 to 20 carbons, the process comprising reacting hydrogen iodide gas with a fluoroalkene in the presence of a catalyst. The present invention also provides a process for producing a fluoroester by reacting the fluoroalkyl iodide with a carboxylate.
    Type: Grant
    Filed: November 20, 2002
    Date of Patent: September 20, 2005
    Assignee: Daikin Industries, Ltd.
    Inventors: Toshiyuki Katsube, Kouzou Noda, Jun Miki
  • Patent number: 6924403
    Abstract: The present invention relates to the process of pyrolyzing tetrafluoroethylene to hexafluoropropylene by carrying out the pyrolysis in a tubular reactor that is lined with either nickel or nickel alloy which contains no greater than 8 wt % chromium.
    Type: Grant
    Filed: May 7, 2003
    Date of Patent: August 2, 2005
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: John James Barnes, Kenneth Paul Kelch, Thomas D. Sandbrook, David John Van Bramer
  • Patent number: 6919490
    Abstract: The present invention relates to a process for continuously producing a perfluoroalkyl iodide represented by the general formula Rf(CF2CF2)nI, wherein Rf is a C1-6 perfluoroalkyl and n is an integer from 1 to 4, the method comprising continuously supplying a perfluoroalkyl iodide as a telogen represented by the general formula RfI, wherein Rf is as defined above, and tetrafluoroethylene as a taxogen to a tubular reactor packed with a metal catalyst comprising a powdery spherical metal or a sintered metal; and conducting telomerization at a temperature of 60 to 160° C. under a pressure of 0.1 to 5 MPa (gauge pressure). According to the present invention, medium-chain perfluoroalkyl iodides can be continuously and efficiently produced with little generation of impurities, such as hydrogen-containing organic compounds and the like.
    Type: Grant
    Filed: April 17, 2002
    Date of Patent: July 19, 2005
    Assignee: Daikin Industries, Ltd.
    Inventors: Yoshio Funakoshi, Jun Miki
  • Patent number: 6897344
    Abstract: Divalent and trivalent metal salts are added to the solution containing the fluorine compound to precipitate the layered double hydroxide containing the fluorine compound between layers. By these processes, the fluorine compound can be fixed with high rate. Moreover, if necessary, the precipitated layered double hydroxide can be recovered to separate the fluorine compound or its salt between layers. Therefore, the burden to environment or the ecosystem by the fluorine compound can be reduced.
    Type: Grant
    Filed: July 26, 2001
    Date of Patent: May 24, 2005
    Assignee: Jemco Inc.
    Inventors: Kiyoshi Fuda, Toshiaki Matsunaga, Takeshi Kamiya, Kota Omori
  • Patent number: 6872861
    Abstract: The invention relates to a process for preparing polyfluoroalkyl-lithium compounds by deprotonation of polyfluoroalkyl compounds by means of lithium bases.
    Type: Grant
    Filed: June 7, 2002
    Date of Patent: March 29, 2005
    Assignee: Bayer Aktiengesellschaft
    Inventors: Marielouise Schneider, Albrecht Marhold, Alexander Kolomeitsev, Alexander Kadyrov, Gerd-Volker Röschenthaler, Jan Barten
  • Patent number: 6861565
    Abstract: A process for producing a fluoroalkanol which can easily be industrially practiced with high selectivity, is provided. CHR1R2OH, a radical initiator and CF2?CFRf are continuously supplied and reacted at from 105 to 135° C., and H—(RfCFCF2)n—CR1R2—OH formed, is continuously discharged. Here, each of R1 and R2 is a hydrogen atom or a C1-3 alkyl group, Rf is a fluorine atom or a C1-4 polyfluoroalkyl group, and n is an integer of from 1 to 4.
    Type: Grant
    Filed: March 10, 2003
    Date of Patent: March 1, 2005
    Assignee: Asahi Glass Company, Limited
    Inventors: Toshihiko Tohma, Akihiro Wada
  • Patent number: 6858763
    Abstract: The present invention relates to a process for preparing an elastomeric ethylene-hexafluoropropylene copolymer with excellent vulcanization properties, which comprises emulsion polymerizing ethylene, hexafluoropropylene and when in demand, a monomer copolymerizable therewith in a aqueous medium at a low temperature of ?20° C. to 40° C. using a radical polymerization initiator.
    Type: Grant
    Filed: September 19, 2001
    Date of Patent: February 22, 2005
    Assignee: Daikin Industries, Ltd.
    Inventors: Mitsuo Tsukamoto, Masao Otsuka, Mitsuhiro Otani, Tatsuya Morikawa, Hideya Saito
  • Patent number: 6774270
    Abstract: A method of removing hexafluoropropylene dimers (“HFP dimers”), dimer hydrides and other oligomers from a fluid is described. The method comprises heating the fluid to isomerize the HFP dimers to the thermodynamic isomer, and contacting the fluid with a tertiary amine (or salts thereof) to form a hexafluoropropylene dimer—tertiary amine adduct. The method may further comprise the step of separating the dimer adducts from the reaction mixture.
    Type: Grant
    Filed: April 1, 2003
    Date of Patent: August 10, 2004
    Assignee: 3M Innovative Properties Company
    Inventors: Zhongxing Zhang, Zai-Ming Qiu, Daniel R. Vitcak, Richard M. Flynn
  • Patent number: 6747178
    Abstract: According to the present invention there is provided a method of carrying out a chemical reaction between at least two fluids, the method comprising providing respective flow paths for the at least two fluids, said flow paths communicating with each other in a region in which the at least two fluids may contact each other, and flowing the at least two fluids along said flow paths such that in said region the at least two fluids contact each other and a chemical reaction occurs between them, said region having a width perpendicular to the direction of flow in the range 10-10,000 micrometers. It has been found that using a so-called “microreactor”, that is a reactor having dimensions perpendicular to the flow direction of less than 10,000 micrometers, according to the present method, improved control over a fluid chemical reaction can be achieved, which can result in significant improvements in reaction product yield and/or purity, as well as other benefits.
    Type: Grant
    Filed: October 2, 2000
    Date of Patent: June 8, 2004
    Assignee: British Nuclear Fuels plc
    Inventors: Paul Harston, Malcolm John Atherton, Robert G. Holmes, Richard Dickinson Chambers, Robert Spink
  • Patent number: 6743957
    Abstract: Divalent and trivalent metal salts are added to the solution containing the fluorine compound and the polymer containing fluorine to precipitate the layered double hydroxide containing the fluorine compound between layers. At this time, the polymer containing fluorine suspended in the solution is also coagulated to precipitate. By these processes, the fluorine compound is fixed with high rate to separate from the solution with the polymer containing fluorine, and recovered if necessary. By this treatment process, the fluorine compound and the polymer containing fluorine, contained in the wastewater etc. can be separated easily, and the burden to environment or ecosystem can be reduced.
    Type: Grant
    Filed: June 26, 2002
    Date of Patent: June 1, 2004
    Assignee: JEMCO, Inc.
    Inventors: Kiyoshi Fuda, Toshiaki Matsunaga, Takeshi Na Kamiya, Kota Omori
  • 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: 20030208090
    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.
    Type: Application
    Filed: June 12, 2003
    Publication date: November 6, 2003
    Inventors: Ralph Thomas Baker, Ralph Newton Miller, Viacheslav Alexandrovich Petrov, Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
  • Patent number: 6638365
    Abstract: A method of preparing a silicon surface for a subsequent processing said such as thermal oxidation, or metal silicide formation, via use of a novel wet chemical clean procedure, has been developed. The novel wet chemical clean procedure is comprised of three specific stages, with the first stage featuring the removal of organic contaminants and the growth of a native oxide layer on the silicon surface. A second stage features removal of the native oxide layer and removal of metallic contaminants from the silicon surface, while the third stage is used to dry the silicon surface. The novel wet chemical clean procedure is performed in less time, and using less chemicals, then counterpart wet chemical cleans also used for the preparation of silicon surfaces for subsequent processing steps.
    Type: Grant
    Filed: October 9, 2001
    Date of Patent: October 28, 2003
    Assignees: Chartered Semiconductor Manufacturing Ltd., Institute of Materials Research and Engineering
    Inventors: Jianhui Ye, Simon Chooi, Alex See
  • Publication number: 20030176747
    Abstract: A process for the production of a fluorinated organic compound, characterized by fluorinating an organic compound having a hydrogen atoms using IF5; and a novel fluorination process for fluorinating an organic compound having a hydrogen atoms by using a fluorinating agent containing IF5 and at least one member selected from the group consisting of acids, bases, salts and additives.
    Type: Application
    Filed: December 10, 2002
    Publication date: September 18, 2003
    Inventors: Norihiko Yoneda, Tsuyoshi Fukuhara, Kazuhiro Shimokawa, Kenji Adachi, Satoshi Oishi
  • Patent number: 6583328
    Abstract: A method for the production of 1,1,1,3,3-pentafluoropropene, and particularly to a method characterized by high conversion, yield and selectivity by contacting 2,2-dichloro-1,1,1,3,3,3-hexafluoropropane with hydrogen in the presence of a metal-containing catalyst. The 1,1,1,3,3-pentafluoropropene then can be reacted with hydrogen in the presence of a metal-containing catalyst to produce 1,1,1,3,3-pentafluoropropane.
    Type: Grant
    Filed: April 5, 1999
    Date of Patent: June 24, 2003
    Assignee: PCBU Services, Inc.
    Inventors: John Cheng-Ping Qian, Julia Ann Sacarias
  • Patent number: 6403846
    Abstract: A composition containing less than 95 mol % of a trihydrofluorinated saturated hydrocarbon represented by the following formula (I) Rf1—R1—Rf2  (I) (wherein R1 represents a carbon chain in which CHF and CH2 are bound, and Rf1 and Rf2 are bound to each other to form a ring by a perfluoroalkylene chain of 2 to 4 carbon atoms) and the balance of a tetrahydrofluorinated saturated hydrocarbon having the same carbon number and the same carbon structure as the trihydrofluorinated saturated hydrocarbon, as represented by the following formula (II) Rf1—R2—Rf2  (II) (wherein R2 represents a carbon chain in which CH2 and CH3 are bound, and Rf1 and Rf2 are as defined above) is provided as a composition containing, in a high proportion, trihydrofluorocarbon, a hydrofluorocarbon (HFC) known to have a small global heating coefficient, which has less influence on the global environment, shows less toxicity to animals, and is chemically stable.
    Type: Grant
    Filed: February 3, 2000
    Date of Patent: June 11, 2002
    Assignees: Japan as Represented by Director General of Agency of Industrial Science and Technology, Nippon Zeon Co., Ltd.
    Inventors: Akira Sekiya, Toshirou Yamada, Takashi Uruma, Tatsuya Sugimoto
  • Patent number: 6156163
    Abstract: A reagent comprising a compound of formula (I): R.sub.f --M(X) (Z).sub.n --Y--R, wherein R is a hydrocarbon radical advantageously having at most 10 carbon atoms and being selected from alkyls and aryls; R.sub.f is a radical of formula II: R.sub.1 --(C.XI..sub.2).sub.m --CF.sub.2 --, where R.sub.1 is a fluorine or chlorine atom or a carbon radical, m is 0 or a integer from 0-12, and each .XI., which may be the same or different, is a chlorine or preferably fluorine atom, with the proviso that when m is 0, R.sub.1 is electroattractive, preferably a fluorine atom;n is 0 or 1; M is a non-metal selected from carbon and chalcogens with an atomic number higher than oxygen; and each of X, Y and Z, which are the same or different, is a chalcogen; as well as a generator, for consecutive or simultaneous addition. The reagent is useful for organic synthesis.
    Type: Grant
    Filed: November 6, 1997
    Date of Patent: December 5, 2000
    Assignee: Rhodia Chimie
    Inventors: Bernard Langlois, Nicolas Roques, Claude Wakselman, Marc Tordeux, Gerard Forat
  • Patent number: 6121212
    Abstract: The present invention concerns a lubricant for improving the gliding properties of skis and its application to skiing. The lubricant possesses an elevated molecular weight but has a very low melting point. Furthermore, the lubricant does not crystallize easily and thus remains oily or waxy also at low temperatures. The lubricant is constituted of four perfluorinated chains attached to a hydrogenated core in a symmetrical arrangement in such a manner that a tetra-substituted derivative or tetrakis derivative is formed according to the following formula ##STR1## wherein each R.sub.x group can be the same or different and comprises a perfluorinated alkyl group.
    Type: Grant
    Filed: March 3, 1999
    Date of Patent: September 19, 2000
    Assignee: Centeiro Trading LDA
    Inventor: Gian Paolo Gambaretto
  • Patent number: 6093859
    Abstract: A process is disclosed for producing the hydrofluorocarbon CF.sub.3 CH.dbd.CF.sub.2. The process involves dehydrofluorinating CF.sub.3 CH.sub.2 CF.sub.3 at an elevated temperature in the vapor phase over a catalyst of (1) aluminum fluoride, (2) fluorided alumina, (3) metal supported on a trivalent aluminum compound containing fluoride anion, (4) lanthanum fluoride, (5) fluorided lanthanum oxide, (6) metal supported on a trivalent lanthanum compound containing fluoride anion, (7) trivalent chromium compounds and/or (8) catalysts of (a) at least one compound selected from the oxides, fluorides and oxyfluorides of magnesium, zinc and mixtures of magnesium and zinc, and optionally (b) at least one compound selected from the oxides, fluorides and oxyfluorides of aluminum, provided that the atomic ratio of aluminum to the total of magnesium and zinc in said catalyst is about 1:4, or less, to produce a product containing CF.sub.3 CH.dbd.CF.sub.2 and HF. The CF.sub.3 CH.dbd.CF.sub.
    Type: Grant
    Filed: June 1, 1999
    Date of Patent: July 25, 2000
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mario Joseph Nappa, V. N. Mallikarjuna Rao, Allen Capron Sievert
  • Patent number: 6093860
    Abstract: A method for producing perfluoro(n-pentane), which comprises fluorinating perfluoro(2-pentene) by bringing the perfluoro(2-pentene) into contact with a fluorine gas in the presence of a solvent.
    Type: Grant
    Filed: June 22, 1999
    Date of Patent: July 25, 2000
    Assignee: Asahi Glass Company Ltd.
    Inventors: Kunio Watanabe, Takashi Okazoe, Shin Tatematsu
  • Patent number: 5986151
    Abstract: A process for the preparation of fluorinated propanes and propenes. CF.sub.3 CH.dbd.CH.sub.2 is produced from CF.sub.3 CH.sub.2 CHF.sub.2 by the sequential steps of dehydrofluorination, a reduction, and a second dehydrofluorination in which the same catalyst is preferably used for each step. Preferably the catalysts is palladium on carbon. The process provides the steps of passing CF.sub.3 CH.sub.2 CHF.sub.2 over a Pd/C catalyst to form CF.sub.3 CH.dbd.CHF; hydrogenating CF.sub.3 CH.dbd.CHF over a Pd/C catalyst to give CF.sub.3 CH.sub.2 CH.sub.2 F; and passing CF.sub.3 CH.sub.2 CH.sub.2 F over a Pd/C catalyst to give CF.sub.3 CH.dbd.CH.sub.2.
    Type: Grant
    Filed: August 28, 1998
    Date of Patent: November 16, 1999
    Assignee: AlliedSignal Inc.
    Inventor: Michael Van Der Puy
  • Patent number: 5969199
    Abstract: The invention relates to a process for the addition of HF to halogenated alkenes by reacting these with at least one hydrofluoride of the formula [B.cndot.n HF], in which B is an organic nitrogen base and n is an integer or fraction .ltoreq.4, it being intended that the reaction of perfluoroiso-butene CF.sub.2 =C(CF.sub.3).sub.2 is excluded.
    Type: Grant
    Filed: June 8, 1998
    Date of Patent: October 19, 1999
    Assignee: Solvay S.A.
    Inventors: Raimund Franz, Gunter Siegemund
  • Patent number: 5945573
    Abstract: A process is disclosed for producing the hydrofluorocarbon CF.sub.3 CH.sub.2 CHF.sub.2. The process involves dehydrofluorinating CF.sub.3 CH.sub.2 CF.sub.3 at an elevated temperature in the vapor phase over a catalyst of (1) aluminum fluoride, (2) fluorided alumina, (3) metal supported on a trivalent aluminum compound containing fluoride anion, (4) lanthanum fluoride, (5) fluorided lanthanum oxide, (6) metal supported on a trivalent lanthanum compound containing fluoride anion, (7) trivalent chromium compounds and/or (8) catalysts of (a) at least one compound selected from the oxides, fluorides and oxyfluorides of magnesium, zinc and mixtures of magnesium and zinc, and optionally (b) at least one compound selected from the oxides, fluorides and oxyfluorides of aluminum, provided that the atomic ratio of aluminum to the total of magnesium and zinc in said catalyst is about 1:4, or less, to produce a product containing CF.sub.3 CH.dbd.CF.sub.2 and HF; and reacting the CF.sub.3 CH.dbd.CF.sub.
    Type: Grant
    Filed: January 9, 1998
    Date of Patent: August 31, 1999
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mario Joseph Nappa, V. N. Mallikarjuna Rao, Allen Capron Sievert
  • Patent number: 5914432
    Abstract: A halogenated compound (I) containing one or more >C.dbd.O, olefinic and/or aromatic >C.dbd.C< groups is hydrogenated for producing a halogenated compound (II) having no or a decreased level of >C.dbd.O, olefinic and/or aromatic >C.dbd.C< groups. In the hydrogenation process a liquid feed stream comprising one or more of these compounds (I) is contacted with a hydrogen-rich gaseous stream and a liquid recycle stream comprising one or more of these compounds (II) in the presence of a catalyst.
    Type: Grant
    Filed: March 27, 1997
    Date of Patent: June 22, 1999
    Assignee: The Dow Chemical Company
    Inventor: Celio Lume-Pereira