Utilizing Halogen Fluoride Or A Mixture Of Elemental Fluorine And Another Elemental Halogen Patents (Class 570/161)
  • Patent number: 9981891
    Abstract: The present invention relates to the field of saturated fluorohydrocarbons. The subject matter thereof is more particularly the production of 1-chloro-2,2-difluoroethane from 1,1,2-trichloroethane and/or 1,2-dichloroethylene. A process for producing 1-chloro-2,2-difluoroethane from 1,1,2-trichloroethane and/or 1,2-dichloroethylene including (i) at least one step during which the 1,1,2-trichloroethane and/or the 1,2-dichloroethylene reacts or react with hydrofluoric acid in the gas phase, optionally in the presence of an oxidizing agent, in the presence or in the absence of a fluorination catalyst, to give a stream including 1-chloro-2,2-difluoroethane, hydrochloric acid, hydrofluoric acid and at least one C compound(s) chosen from 1-chloro-2-fluoroethylenes (cis and trans), 1,2-dichloro-2-fluoroethane and, optionally, unreacted 1,1,2-trichloroethane and/or 1,2-dichloroethylene.
    Type: Grant
    Filed: November 28, 2014
    Date of Patent: May 29, 2018
    Assignee: ARKEMA FRANCE
    Inventors: Philippe Bonnet, Bertrand Collier, Dominique Garrait, Pierre-Marie Sedat
  • Patent number: 9000242
    Abstract: The invention is directed to a catalyst for the gas phase fluorination of 1,1,2-trichloroethane and/or 1,2-dichloroethene with HF to give 1-chloro-2,2-difluoroethane which catalyst is prepared by co-depositing FeCl3 and MgCl2 on chromia-alumina, or co-depositing Cr(NO3)3 and Ni(NO3)2 on active carbon, or by doping alumina with ZnCl2, and to a process for the preparation of 1-chloro-2,2-difluoroethane comprising a catalytic gas phase fluorination of 1,1,2-trichloroethane and/or 1,2-dichloroethene wherein one of the catalysts according to claim 2 or 3 is used.
    Type: Grant
    Filed: October 11, 2012
    Date of Patent: April 7, 2015
    Assignee: Bayer Intellectual Property
    Inventors: Norbert Lui, Shanthan Rao Pamulaparthy, Srinivas Pvss, Thomas Vijaya, Sridhar Madabhushi, Rambabu Yadla, Narsaiah Banda, Sergii Pazenok
  • Publication number: 20140350311
    Abstract: Disclosed are processes for the production of fluorinated olefins, preferably adapted to commercialization of CF3CF?CH2 (1234yf). In certain preferred embodiments the processes comprise first exposing a compound of Formula (IA) C(X)2?CClC(X)3 ??(IA) where each X is independently F, Cl or H, preferably CCl2?CClCH2Cl, to one or more sets of reaction conditions, but preferably a substantially single set of reaction conditions, effective to produce at least one chlorofluoropropane, preferably in accordance with Formula (IB): CF3CClX?C(X?)3 ??Formula (IB) where each X? is independently F, Cl or H, and then exposing the compound of Formula (IB) to one or more sets of reaction conditions, but preferably a substantially single set of reaction conditions, effective to produce a compound of Formula (II) CF3CF?CHZ ??(II) where Z is H, F, Cl, I or Br.
    Type: Application
    Filed: August 12, 2014
    Publication date: November 27, 2014
    Inventors: ROBERT C. JOHNSON, HSUEH S. TUNG, DANIEL C. MERKEL
  • Publication number: 20140330051
    Abstract: The invention is directed to a catalyst for the gas phase fluorination of 1,1,2-trichloroethane and/or 1,2-dichloroethene with HF to give 1-chloro-2,2-difluoroethane which catalyst is prepared by co-depositing FeCl3 and MgCl2 on chromia-alumina, or co-depositing Cr(NO3)3 and Ni(NO3)2 on active carbon, or by doping alumina with ZnCl2, and to a process for the preparation of 1-chloro-2,2-difluoroethane comprising a catalytic gas phase fluorination of 1,1,2-trichloroethane and/or 1,2-dichloroethene wherein one of the catalysts according to claim 2 or 3 is used.
    Type: Application
    Filed: October 11, 2012
    Publication date: November 6, 2014
    Applicant: BAYER INTELLECTUAL PROPERTY GMBH
    Inventors: Norbert Lui, Shanthan Rao Pamulaparthy, Srinivas Pvss, Thomas Vijaya, Sridhar Madabhushi, Rambabu Yadla, Narsaiah Banda, Sergii Pazenok
  • 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
  • Patent number: 8716538
    Abstract: Provided is a process for purifying an organic feedstock comprising (a) distilling a raw organic feedstock comprising hydrogen fluoride, 2-chloro-1,1,1,2-tetrafluoropropane, and 2-chloro-3,3,3-trifluoropropene to produce a first distillate stream comprising an azeotrope-like composition of 2-chloro-1,1,1,2-tetrafluoropropane, 2-chloro-3,3,3-trifluoropropene, and hydrogen fluoride, and a first bottoms stream rich in hydrogen fluoride; (b) cooling said first distillate stream to produce an intermediate composition comprising an organic layer rich in 2-chloro-1,1,1,2-tetrafluoropropane and 2-chloro-3,3,3-trifluoropropene, and an acid layer rich in hydrogen fluoride; and, optionally but preferably, (c) distilling said organic layer to produce a second distillate stream comprising an azeotrope-like composition of 2-chloro-1,1,1,2-tetrafluoropropane, 2-chloro-3,3,3-trifluoropropene, and hydrogen fluoride, and a second bottoms stream comprising a purified organic feedstock substantially free of hydrogen fluoride.
    Type: Grant
    Filed: August 2, 2013
    Date of Patent: May 6, 2014
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh S. Tung
  • Patent number: 8546623
    Abstract: The invention relates to a process for preparing a C3-6 hydrofluoroalkene comprising dehydrohalogenating a C3-6 hydrohalofluoroalkane in the presence of a zinc/chromia catalyst.
    Type: Grant
    Filed: October 3, 2007
    Date of Patent: October 1, 2013
    Assignee: Mexichem Amanco Holding S.A. de C.V.
    Inventors: Andrew Paul Sharratt, Leslie Seddon
  • Patent number: 8541634
    Abstract: Disclosed are azeotropic and azeotrope-like mixtures of (Z)-1-chloro-3,3,3-trifluoropropene (1233zd(Z)) and hydrogen fluoride. Such compositions are useful as an intermediate in the production of 1233zd(Z). The latter compound is useful as a nontoxic, zero ozone depleting fluorocarbon useful as a solvent, blowing agent, refrigerant, cleaning agent, aerosol propellant, heat transfer medium, dielectric, fire extinguishing composition and power cycle working fluid.
    Type: Grant
    Filed: January 14, 2013
    Date of Patent: September 24, 2013
    Assignee: Honeywell International Inc.
    Inventors: Ryan Hulse, Hang T Pham
  • Publication number: 20130245341
    Abstract: Process of catalytic fluorination in liquid phase of product 2-chloro-3, 3, 3-trifluoropropene into product 2-chloro-1, 1, 1, 2-tetrafluoropropane, with an ionic liquid based catalyst. Process for manufacturing 2, 3, 3, 3-tetrafluoropropene.
    Type: Application
    Filed: October 25, 2010
    Publication date: September 19, 2013
    Inventors: Anne Pigamo, Laurent Wendlinger, Phillppe Bonnet
  • Patent number: 8519201
    Abstract: Provided is a process for purifying an organic feedstock comprising (a) distilling a raw organic feedstock comprising hydrogen fluoride, 2-chloro-1,1,1,2-tetrafluoropropane, and 2-chloro-3,3,3-trifluoropropene to produce a first distillate stream comprising an azeotrope-like composition of 2-chloro-1,1,1,2-tetrafluoropropane, 2-chloro-3,3,3-trifluoropropene, and hydrogen fluoride, and a first bottoms stream rich in hydrogen fluoride; (b) cooling said first distillate stream to produce an intermediate composition comprising an organic layer rich in 2-chloro-1,1,1,2-tetrafluoropropane and 2-chloro-3,3,3-trifluoropropene, and an acid layer rich in hydrogen fluoride; and, optionally but preferably, (c) distilling said organic layer to produce a second distillate stream comprising an azeotrope-like composition of 2-chloro-1,1,1,2-tetrafluoropropane, 2-chloro-3,3,3-trifluoropropene, and hydrogen fluoride, and a second bottoms stream comprising a purified organic feedstock substantially free of hydrogen fluoride.
    Type: Grant
    Filed: March 19, 2012
    Date of Patent: August 27, 2013
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh S. Tung
  • Patent number: 8420872
    Abstract: The present invention provides a process for preparing a fluorine-containing propene represented by the chemical formula CF3CF?CX1X2, wherein X1 is a hydrogen atom or chlorine atom, and X2 is a fluorine atom, chlorine atom, or hydrogen atom, by reacting a halogenated propene represented by the chemical formula CCIYZCF?CX1X2, wherein X1 and X2 are the same as above, and Y and Z may be the same or different and individually indicate a fluorine atom or chlorine atom, with anhydrous hydrogen fluoride in a gas phase in the presence of a chromium oxide or a fluorinated chromium oxide as a fluorination catalyst. The process of the present invention provides a fluorine-containing propene represented by the chemical formula CF3CF?CClX, wherein X is Cl, H or F, under relatively mild conditions at a high yield.
    Type: Grant
    Filed: June 25, 2009
    Date of Patent: April 16, 2013
    Assignee: Daikin Industries, Ltd.
    Inventors: Masatoshi Nose, Akinari Sugiyama, Atsushi Suzuki
  • Patent number: 8415516
    Abstract: It is an object of the present invention to provide a process for producing 1,2,3,4 -tetrachlorohexafluorobutane industrially inexpensively and efficiently by utilizing expensive fluorine gas efficiently and to provide a process which is capable of stably producing 1,2,3,4 -tetrachlorohexafluorobutane and in which, by carrying out fluorination reaction at a low temperature, side reactions such as formation of a low-boiling substance due to cleavage of C—C bonds and formation of an excess fluoride are difficult to occur. The process for producing 1,2,3,4-tetrachlorohexafluorobutane of the present invention is characterized in that it includes feeding fluorine gas to 1,2,3,4-tetrachlorobutane using plural reactors in the presence of a solvent and in the absence of a catalyst to allow the 1,2,3,4-tetrachlorobutane and the fluorine gas to react with each other, wherein a part or all of unreacted fluorine gas discharged from one reactor is introduced into a reactor different from said one reactor.
    Type: Grant
    Filed: May 11, 2009
    Date of Patent: April 9, 2013
    Assignee: Showa Denko K.K.
    Inventors: Hiromoto Ohno, Toshio Ohi
  • Patent number: 8404906
    Abstract: The present invention provides a process for producing 1,2,3,4-tetrachlorohexafluorobutane having a high purity at a low cost industrially and efficiently. The process for producing 1,2,3,4-tetrachlorohexafluorobutane according to the present invention comprises a step of allowing 1,2,3,4-tetrachlorobutane to react with a fluorine gas to prepare a reaction product containing 1,2,3,4-tetrachlorohexafluorobutane and hydrogen-containing compounds as an impurity, and a step of introducing the reaction product into single or plural distillation columns and distilling to separate the hydrogen-containing compounds from the reaction product and thereby preparing purified 1,2,3,4-tetrachlorohexafluorobutane wherein the at least one of distillation columns has a theoretical plate number of 15 or more.
    Type: Grant
    Filed: June 24, 2009
    Date of Patent: March 26, 2013
    Assignee: Showa Denko K.K.
    Inventors: Hiromoto Ohno, Toshio Ohi, Takami Ohe
  • Patent number: 8378158
    Abstract: Disclosed are azeotropic and azeotrope-like mixtures of (Z)-1-chloro-3,3,3-trifluoropropene (1233zd(Z)) and hydrogen fluoride. Such compositions are useful as an intermediate in the production of 1233zd(Z). The latter compound is useful as a nontoxic, zero ozone depleting fluorocarbon useful as a solvent, blowing agent, refrigerant, cleaning agent, aerosol propellant, heat transfer medium, dielectric, fire extinguishing composition and power cycle working fluid.
    Type: Grant
    Filed: October 5, 2011
    Date of Patent: February 19, 2013
    Assignee: Honeywell International Inc.
    Inventors: Ryan Hulse, Hang T. Pham
  • Patent number: 8350082
    Abstract: This process for producing fluorine-containing compounds includes liquid-phase fluorination by introducing a raw material compound and fluorine gas into a solvent to replace hydrogen atoms in the raw material compound with fluorine atoms. More specifically, the process for producing fluorine-containing compounds includes (1) promoting fluorination by dissolving the raw material compound in anhydrous hydrofluoric acid and introducing into a liquid-phase fluorination solvent, or (2) promoting fluorination by dissolving the raw material compound in a perfluoro compound having a plurality of polar groups in a molecule thereof and introducing into a liquid-phase fluorination solvent. According to these processes, a fluorination reaction can be carried out at high yield and without containing hardly any isomers while using a hydrocarbon compound as is for the raw material.
    Type: Grant
    Filed: November 28, 2008
    Date of Patent: January 8, 2013
    Assignees: Mitsubishi Materials Corporation, Mitsubishi Materials Electronic Chemicals Co., Ltd.
    Inventors: Mitsuo Kurumaya, Tsunetoshi Honda, Kota Omori
  • Patent number: 8293954
    Abstract: This invention achieves a catalyst life improvement for the catalyzed vapor phase reaction of 1,1,1,3,3-pentachloropropane with hydrogen fluoride to form 1-chloro-3,3,3-trifluoropropene by introducing an oxygen co-feed into the fluorination reactor. By introduction of an oxygen co-feed to the reactor feed, the catalyst life was extended a minimum of two-fold (2×).
    Type: Grant
    Filed: March 10, 2010
    Date of Patent: October 23, 2012
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh Sung Tung
  • Patent number: 8293955
    Abstract: The production process for 1,2,3,4-tetrachlorohexafluorobutane of the present invention is characterized in that 1,2,3,4-tetrachlorobutane is reacted with fluorine in the presence of a solvent containing hydrogen fluoride. The 1,2,3,4-tetrachlorobutane may be obtained by chlorination of 3,4-dichlorobutene-1. Further, the present invention provides as well a process of refining 1,2,3,4-tetrachlorohexafluorobutane obtained in the manner described above. According to the present invention, 1,2,3,4-tetrachlorohexafluorobutane which is useful, for example, as a synthetic raw material for hexafluoro-1,3-butadiene used as an etching gas for semiconductors can industrially efficiently be produced by using 1,2,3,4-tetrachlorobutane which is a by-product of chloroprene and which has so far been disposed.
    Type: Grant
    Filed: March 26, 2008
    Date of Patent: October 23, 2012
    Assignee: Showa Denko K.K.
    Inventors: Hiromoto Ohno, Toshio Ohi, Nobutoshi Sasaki, Kiyoshi Nomura
  • Patent number: 8258352
    Abstract: The production process of the present invention for a chlorine-containing fluorine-containing compound is characterized in that a reaction of adding chlorine atoms to a carbon-carbon unsaturated bond of a hydrogen-containing compound having a carbon-carbon unsaturated bond is carried out under the presence of a fluorine gas. The hydrogen-containing compound having a carbon-carbon unsaturated bond may be 3,4-dichlorobutene-1. Further, the present invention provides a process for producing efficiently and economically 1,2,3,4 -tetrachlorohexafluorobutane from 3,4-dichlorobutene-1 described above. According to the present invention, chlorination and fluorination of the hydrogen-containing compound having a carbon-carbon unsaturated bond are carried out in a single step, and therefore a chlorine-containing fluorine-containing compound can be more economically produced at a higher yield than in a conventional process in which two reactions are individually carried out.
    Type: Grant
    Filed: March 27, 2008
    Date of Patent: September 4, 2012
    Assignee: Showa Denko K.K.
    Inventors: Hiromoto Ohno, Toshio Ohi, Takami Ohe
  • Patent number: 8058487
    Abstract: The present invention relates to a continuous process for the fluorination of perchloroethylene (PER) in the gas phase in a single stage with hydrofluoric acid (HF) in the presence of a catalyst to give, as major product, pentafluoroethane. The process is characterized in that it is carried out at a temperature of between 280 and 430° C. and with an HF/PER molar ratio of greater than or equal to 20.
    Type: Grant
    Filed: November 30, 2006
    Date of Patent: November 15, 2011
    Assignee: Arkema France
    Inventors: Beatrice Boussand, Michel Devic
  • Patent number: 8030528
    Abstract: The process for producing a fluorine-containing compound such as 1,2,3,4-tetrachlorohexafluorobutane of the present invention is characterized in that a halogenated hydrocarbon compound such as 1,2,3,4-tetrachlorobutane is brought into contact with fluorine gas in a liquid phase or in a solid-liquid coexistence state in the absence of a solvent and a catalyst. According to the present invention, a fluorine-containing compound is readily produced from a halogenated hydrocarbon compound using neither a reaction solvent nor a reaction catalyst.
    Type: Grant
    Filed: April 14, 2008
    Date of Patent: October 4, 2011
    Assignee: Showa Denko K.K.
    Inventors: Hiromoto Ohno, Toshio Ohi
  • Patent number: 7982074
    Abstract: The present invention relates to a process for preparing a co-precipitated Cr2O3/Al2O3 catalyst promoted by Zinc, said process comprising co-precipatation of chromium and aluminum metal hydroxides from corresponding trivalent metal salt solutions using NH4OH, NaOH or KOH as a base and followed by calcination to give mixed oxide precatalyst in amorphous from which is impregnated with an activity promoting amount of Zinc compound. The catalyst is used for the preparation of HFC-134a by fluorination of trichloroethylene and fluorination of intermediate of the former reaction (HCFC-133a).
    Type: Grant
    Filed: December 22, 2006
    Date of Patent: July 19, 2011
    Assignee: Council of Scientific & Industrial Research
    Inventors: Jampani Madhusudana Rao, Shanthan Pamulaparthy Rao, Siva Attaluri Prasad, Banda Narasaiah, Narayan Sripathi Reddy, Radhakrishnan Kuppusamy, Vijayakumar Veeramachaneni, Patil Kamalakar Sukhadeorao, Rambabu Yadla, Koosampally Srinivas, Leelakrishna Kondaveti
  • Publication number: 20100312026
    Abstract: A method of catalytically converting 2,2, dichlorohexafluoropropane (HFC-216aa) into 2 chloro 1,1,1,2,3,3,3 heptafluoropropane (HFC-217ba) including the step of exposing the 2,2 dichlorohexafluoropropane to a chromium-containing catalyst comprising a metal oxide, a halogenated metal oxide or a metal oxyhalide, which chromium-containing catalyst comprises 0.01% to 5.0% by weight zinc or a compound of zinc.
    Type: Application
    Filed: November 10, 2008
    Publication date: December 9, 2010
    Inventors: Andrew P. Sharratt, John C. McCarthy
  • Patent number: 7799959
    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: Grant
    Filed: April 25, 2007
    Date of Patent: September 21, 2010
    Assignee: Showa Denko K.K.
    Inventors: Hiromoto Ohno, Toshio Ohi
  • Patent number: 7781626
    Abstract: The invention relates to azeotropic and azeotrope-like mixtures of 1,1,1,3,3-pentafluorobutane (HFC-365) and hydrogen fluoride and a process for separating the azeotrope-like mixtures. The compositions of the invention are useful as an intermediate in the production of HFC-365. The latter is useful as a nontoxic, zero ozone depleting fluorocarbon useful as a solvent, blowing agent, refrigerant, cleaning agent and aerosol to propellant.
    Type: Grant
    Filed: August 21, 2007
    Date of Patent: August 24, 2010
    Assignee: Honeywell International Inc
    Inventors: Hang T. Pham, Rajiv R. Singh, Hsueh S. Tung
  • Publication number: 20100105968
    Abstract: The production process of the present invention for a chlorine-containing fluorine-containing compound is characterized in that a reaction of adding chlorine atoms to a carbon-carbon unsaturated bond of a hydrogen-containing compound having a carbon-carbon unsaturated bond is carried out under the presence of a fluorine gas. The hydrogen-containing compound having a carbon-carbon unsaturated bond may be 3,4-dichlorobutene-1. Further, the present invention provides a process for producing efficiently and economically 1,2,3,4-tetrachlorohexafluorobutane from 3,4-dichlorobutene-1 described above. According to the present invention, chlorination and fluorination of the hydrogen-containing compound having a carbon-carbon unsaturated bond are carried out in a single step, and therefore a chlorine-containing fluorine-containing compound can be more economically produced at a higher yield than in a conventional process in which two reactions are individually carried out.
    Type: Application
    Filed: March 27, 2008
    Publication date: April 29, 2010
    Applicant: Showa Denko K.K.
    Inventors: Hiromoto Ohno, Toshio Ohi, Takami Ohe
  • Patent number: 7683222
    Abstract: A method of producing a fluorine-containing compound, which contains the step of: fluorinating a substrate in a solvent with fluorine gas, wherein as said substrate, a substrate that cannot substantially undergo fluorinating reaction independently, is allowed to react, in the presence of a substrate that rapidly undergoes fluorinating reaction independently.
    Type: Grant
    Filed: October 5, 2005
    Date of Patent: March 23, 2010
    Assignee: Fujifilm Corporation
    Inventors: Yushi Kaneko, Takayuki Ito, Taizo Ono
  • Patent number: 7659436
    Abstract: A process for the manufacture of CF3CH2CHF2 and/or 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 Cl) 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; and (c) recovering CF3CH2CHF2 and/or CF3CH2CF3 from the product produced in (b). 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 0.05 atom % of the chromium atoms in the alpha-chromium oxide lattice are replaced by divalent copper, and (ii) a chromium-containing composition of (i) which has been treated with a fluorinating agent.
    Type: Grant
    Filed: August 4, 2006
    Date of Patent: February 9, 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: 7659435
    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 CF3CCl2CF3 and CF3CClFCClF2 are produced in the presence of a chlorofluorination catalyst including (i) a crystalline alpha-chromium oxide where at least 0.05 atom % of the chromium atoms in the alpha-chromium oxide lattice are replaced by divalent copper, and/or (ii) a chromium-containing composition of (i) which has been treated with a fluorinating agent.
    Type: Grant
    Filed: August 4, 2006
    Date of Patent: February 9, 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: 7524999
    Abstract: A process for the preparation of 1,1,1,3,3,3-hexafluoropropane is disclosed. The process involves (a) contacting at least one halopropane of the formula CF3CH2CHyX3-y (where each X is independently F, Cl or Br, and y is 3, 2, or 1) with Cl?2#191 in the presence of light or a free radical initiator to produce a mixture comprising CF3CH2CCIyX3-y; (b) contacting the CF3CH2CCIyX3-y produced in step (a) with HF, optionally in the presence of a fluorination catalyst, to produce a product mixture comprising CF3CH2CF3; and (c) recovering CF3CH2CF3 from the mixture produced in step (b).
    Type: Grant
    Filed: December 19, 2005
    Date of Patent: April 28, 2009
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mario Joseph Nappa, Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
  • Publication number: 20090105510
    Abstract: A method for the preparation of a novel fluorinated compound, particularly 1,1,1,3,3-pentafluoropropane (HFC-245fa), by using a fluorination catalyst obtained by treating a metal salt containing a chromium salt such as chromium oxide with chlorine gas and/or oxygen gas. Examples of the metal salt may include, besides a chromium salt, one or more catalytically active metal salts selected from magnesium salts, aluminum salts, zinc salts, sodium salts, nickel salts, iron salts, cobalt salts, vanadium salts, manganese salts and copper salts.
    Type: Application
    Filed: December 17, 2008
    Publication date: April 23, 2009
    Applicant: NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY
    Inventors: Heng-dao Quan, Huie Yang, Masanori Tamura, Akira Sekiya
  • Publication number: 20080108853
    Abstract: A process for the preparation of 1,1,1,3,3,3-hexafluoropropane is disclosed. The process involves (a) contacting at least one halopropane of the formula CF3CH2CHyX3-y (where each X is independently F, Cl or Br, and y is 3, 2, or 1) with Cl?2#191 in the presence of light or a free radical initiator to produce a mixture comprising CF3CII2CCIyX3-y; (b) contacting the CF3CH2CCIyX3-y produced in step (a) with HF, optionally in the presence of a fluorination catalyst, to produce a product mixture comprising Cl3CH2Cl3; and (c) recovering Cl3CH2Cl3 from the mixture produced in step (b).
    Type: Application
    Filed: December 19, 2005
    Publication date: May 8, 2008
    Inventors: Mario Joseph Nappa, Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
  • Patent number: 7361795
    Abstract: The invention relates to azeotropic and azeotrope-like mixtures of 1,1,1,3,3-pentafluorobutane (HFC-365) and hydrogen fluoride and a process for separating the azeotrope-like mixtures. The compositions of the invention are useful as an intermediate in the production of HFC-365. The latter is useful as a nontoxic, zero ozone depleting fluorocarbon useful as a solvent, blowing agent, refrigerant, cleaning agent and aerosol to propellant.
    Type: Grant
    Filed: October 14, 2003
    Date of Patent: April 22, 2008
    Assignee: Honeywell International, Inc.
    Inventors: Hang T. Pham, Rajiv R. Singh, Hsueh S. Tung
  • Patent number: 7335805
    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: February 26, 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
  • Publication number: 20070265478
    Abstract: The invention is a method for continuously preparing highly pure octafluorocyclopentene for use in dry-etching processes. The method includes reacting octachlorocyclopentene with KF in a continuous manner, and purifying crude octafluorocyclopentene. In the reacting step, two KF-charged filters are installed in parallel and allowed to communicate with a reactor containing octachlorocyclopentene in an alternating manner to produce crude octafluorocyclopentene. In the purifying step, organics having lower boiling points than octafluorocyclopentene are removed, and metal ingredients and organics having boiling points higher than octafluorocyclopentene are separated to recover octafluorocyclopentene as a gas. The gaseous octafluorocyclopentene composition contains C5F8 in an amount of 99.995 vol % or higher, nitrogen in an amount of 50 vol ppm or less, oxygen in an amount of 5 vol ppm or less, water in an amount of 5 vol ppm or less, and metal ingredients in an amount of 5 wt ppb or less.
    Type: Application
    Filed: September 25, 2006
    Publication date: November 15, 2007
    Applicant: ULSAN CHEMICAL Co., Ltd.
    Inventors: Hae Seok JI, Ook Jae Cho, Jae Gug Ryu, Jong Yeol Yang, Young Hoon Ahn, Bong Suk Kim, Dong Hyun Kim
  • Patent number: 7268261
    Abstract: Methods and materials are disclosed for the recovery of valuable hydrofluorocarbons and subsequent conversion to environmentally inert compounds. More specifically methods and materials are provided for recovering hydrofluorocarbons such as HFC-227, HFC-236, HFC-245, HFC-125, HFC-134, HFC-143, HFC-152, HFC-32, HFC-23 and their respective isomers. Processes are provided for converting hydrofluorocarbons such as these to fluoromonomer precursors such as CFC-217, CFC-216, CFC-215, CFC-115, CFC-114, CFC-113, CFC-112, HCFC-22, CFC-12, CFC-13 and their respective isomers. Materials, methods and schemes are provided for the conversion of these fluoromonomer precursors to fluoromonomers such as HFP, PFP, TFP, TFE, and VDF.
    Type: Grant
    Filed: August 31, 2005
    Date of Patent: September 11, 2007
    Assignee: Great Lakes Chemical Corporation
    Inventors: Yuichi Iikubo, Vicki Hedrick, Stephen M. Brandstadter, Mitchel Cohn
  • Patent number: 7250539
    Abstract: Methods and materials are disclosed for the recovery of valuable hydrofluorocarbons and subsequent conversion to environmentally inert compounds. More specifically methods and materials are provided for recovering hydrofluorocarbons such as HFC-227, HFC-236, HFC-245, HFC-125, HFC-134, HFC-143, HFC-152, HFC-32, HFC-23 and their respective isomers. Processes are provided for converting hydrofluorocarbons such as these to fluoromonomer precursors such as CFC-217, CFC-216, CFC-215, CFC-115, CFC-114, CFC-113, CFC-112, HCFC-22, CFC-12, CFC-13 and their respective isomers. Materials, methods and schemes are provided for the conversion of these fluoromonomer precursors to fluoromonomers such as HFP, PFP, TFP, TFE, and VDF.
    Type: Grant
    Filed: December 30, 2002
    Date of Patent: July 31, 2007
    Assignee: Great Lakes Chemical Corp.
    Inventors: Yuichi Iikubo, Vicki Hedrick, Stephen M. Brandstadter, Mitchel Cohn
  • 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: 7067705
    Abstract: A convenient and economical process for the preparation of 1,1-dichloro-3,3,3-trifluoropropane (HCFC-243) by the reaction of 1,1,1,3,3-pentachloropropane (HCC-240) with hydrogen fluoride in the presence of an activated hydrofluorination catalyst. Also, the selective fluorination of hydrochlorocarbons and/or hydrochlorofluorocarbons, or mixtures thereof is shown. A HCFC-243 reaction product yield of greater than 40% is obtained.
    Type: Grant
    Filed: September 10, 2004
    Date of Patent: June 27, 2006
    Assignee: Honeywell International Inc.
    Inventor: Joseph J. Moscoe
  • 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: 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: 6967260
    Abstract: Tetrafluoromethane containing ethylene compound, hydrocarbon compounds, carbon monoxide and/or carbon dioxide is contacted with zeolite having an average pore size of 3.4 to 11 ? and an Si/Al ratio of 1.5 or less and/or a carbonaceous adsorbent having an average pore size of 3.4 to 11 ?. Thus, high-purity tetrafluoromethane can be obtained which is advantageous in industry and provides good profitability.
    Type: Grant
    Filed: April 26, 2001
    Date of Patent: November 22, 2005
    Assignee: Showa Denko K.K.
    Inventors: Hiromoto Ohno, Toshio Ohi
  • Patent number: 6955789
    Abstract: The present invention relates to a reactor suitable for liquid-phase fluorination and provided, as heating means, with at least one element fixed to the cover so as to be immersed to the bottom of the vessel, characterized in that the parts of said reactor that are liable to be in contact with the reaction medium, other than the heating element, are coated with a tetrafluoroethylene/hexafluoropropylene copolymer and in that the part of the heating element liable to be in contact with the reaction medium is made of silicon carbide.
    Type: Grant
    Filed: January 30, 2003
    Date of Patent: October 18, 2005
    Assignee: ARKEMA
    Inventors: Michel Devic, Philippe Bonnet, Eric Lacroix
  • Publication number: 20040245505
    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: July 7, 2004
    Publication date: December 9, 2004
    Applicant: Daikin Industries, Ltd.
    Inventors: Norihiko Yoneda, Tsuyoshi Fukuhara, Kazuhiro Shimokawa, Kenji Adachi, Satoshi Oishi
  • Patent number: 6784327
    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: Grant
    Filed: December 10, 2002
    Date of Patent: August 31, 2004
    Assignee: Daikin Industries, Ltd.
    Inventors: Norihiko Yoneda, Tsuyoshi Fukuhara, Kazuhiro Shimokawa, Kenji Adachi, Satoshi Oishi
  • Publication number: 20040010168
    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: Application
    Filed: July 12, 2002
    Publication date: January 15, 2004
    Inventors: Rajasekaran Ramanathan, Rajdeep Anand, Anurag Jain, Jampani Madhusudana Rao
  • Patent number: 6673264
    Abstract: The invention relates to azeotropic and azeotrope-like mixtures of 1,1,1,3,3-pentafluorobutane (HFC-365) and hydrogen fluoride and a process for separating the azeotrope-like mixtures. The compositions of the invention are useful as an intermediate in the production of HFC-365. The latter is useful as a nontoxic, zero ozone depleting fluorocarbon useful as a solvent, blowing agent, refrigerant, cleaning agent and aerosol to propellant.
    Type: Grant
    Filed: June 3, 2002
    Date of Patent: January 6, 2004
    Assignee: Honeywell International Inc.
    Inventors: Hang T. Pham, Rajiv R. Singh, Hsueh S. Tung
  • 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
  • Publication number: 20030105368
    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: Application
    Filed: September 28, 2001
    Publication date: June 5, 2003
    Inventors: Yuichi Iikubo, Stephen Owens, Mitchel Cohn, Stephan M. Brandstadter, Vicki E. Hedrick, Janet K. Boggs, John Qian, Julie Sacarias