Substituting Fluorine For A Different Halogen Patents (Class 570/160)
  • Patent number: 8207384
    Abstract: The invention provides a process for preparing 1234yf, comprising: (i) contacting 243db with hydrogen fluoride HF in gas phase in the presence of a fluorination catalyst under conditions sufficient to produce a reaction mixture; (ii) separating the reaction mixture into a first stream comprising HCl, 1234yf and a second stream comprising HF, 1233xf and 245cb; (iii) recycling at least a part of the second stream at least in part back to step (i).
    Type: Grant
    Filed: December 23, 2010
    Date of Patent: June 26, 2012
    Assignee: Arkema France
    Inventors: Laurent Wendlinger, Anne Pigamo, Dominique Deur-Bert
  • Publication number: 20120149951
    Abstract: Disclosed are processes for the production of fluorinated olefins, preferably adapted to commercialization of CF3CF?CH2 (1234yf). Three steps may be used in preferred embodiments in which a feedstock such as CCl2?CClCH2Cl is fluorinated to synthesize a compound such as CF3CCl?CH2. The CF3CCl?CH2 is preferably converted to CF3CFClCH3 (244-isomer) using a SbCl5 as the catalyst which is then transformed selectively to 1234yf. For the first step, a mixture of Cr2O3 and FeCl3/C is preferably used as the catalyst to achieve high selectivity to CF3CCl?CH2 (96%). In the second step, SbCl5/C is preferably used as the selective catalyst for transforming 1233xf to 244-isomer, CF3CFClCH3. The intermediates are preferably isolated and purified by distillation and used in the next step without further purification, preferably to a purity level of greater than about 95%.
    Type: Application
    Filed: November 22, 2011
    Publication date: June 14, 2012
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: SUDIP MUKHOPADHYAY, HSUEH S. TUNG, MICHAEL VAN DER PUY, DANIEL C. MERKEL, JING JI MA, CHERYL L. BORTZ, BARBARA A. LIGHT, STEVEN D. PHILLIPS, RAJESH K. DUBEY
  • Publication number: 20120123172
    Abstract: Production of trans-1,3,3,3-tetrafluoropropene by reacting 1-chloro-3,3,3-trifluoropropene with hydrogen fluoride to obtain a reaction product A containing formed trans-1,3,3,3-tetrafluoropropene, unreacted 1-chloro-3,3,3-trifloropropene and hydrogen fluoride, and by-product cis-1,3,3,3-tetrafluoropropene, 1,1,1,3,3-pentafluoropropane and hydrogen chloride; distilling reaction product A to recover a distillation bottom product containing 1-chloro-3,3,3-trifloropropene and hydrogen fluoride and supplying recovered distillation bottom product to the reacting step; recovering hydrogen fluoride from a residue B remaining after recovery of the distillation bottom product and supplying recovered hydrogen fluoride to the reacting step; contacting a residue C remaining after recovery of hydrogen fluoride with water or aqueous sodium hydroxide solution to separate hydrogen chloride; dehydrating a residue D remaining after separation of hydrogen chloride; and distilling a residue E remaining after the dehydration to ob
    Type: Application
    Filed: October 14, 2011
    Publication date: May 17, 2012
    Applicant: Central Glass Company, Limited
    Inventors: Yasuo Hibino, Satoshi Yoshikawa, Yoshio Nishiguchi, Satoru Okamoto, Fuyuhiko Sakyu
  • Publication number: 20120078020
    Abstract: In this invention we are disclosing a process for the synthesis of hydrocchlorofluoro olefins (HCFO) and/or hydrofluoroolefins (HFO). The process is based on the steps of fluorination of hydrochloropropenes or hydrochloropropanes to form hydrochlorofluoropropenes and/or hydrofluoropropenes, followed by gas phase, catalytic fluorination of the hydrochlorofluoropropenes to form hydrofluoropropenes.
    Type: Application
    Filed: November 16, 2011
    Publication date: March 29, 2012
    Applicant: Arkema Inc.
    Inventors: Maher Y. Elsheikh, Philippe Bonnet, Benjamin Bin Chen
  • Publication number: 20120065434
    Abstract: The present invention provides a process for preparing at least one chlorine-containing fluorocarbon compound selected from the group consisting of chlorine-containing fluoropropane compounds represented by Formula (1): CFnCl3-nCHClCH2—Cl, wherein n is 1 or 2, and chlorine-containing fluoropropene compounds represented by Formula (2): CFnCl3-nCCl?CH2, wherein n is 1 or 2, wherein the process includes the step of contacting at least one chlorine-containing compound selected from the group consisting of 1,1,1,2,3-pentachloropropane, 1,1,2,3-tetrachloropropene, and 2,3,3,3-tetrachloropropene with hydrogen fluoride in the absence of a catalyst while heating. According to the present invention, the chlorine-containing propane and propene compounds having 1 or 2 fluorine atoms can be prepared by an industrially applicable, simple and effective process.
    Type: Application
    Filed: May 12, 2010
    Publication date: March 15, 2012
    Inventors: Masatoshi Nose, Tsuneo Yamashita, Atsushi Suzuki
  • Patent number: 8133406
    Abstract: A process is disclosed for making CF3CF?CH2 or mixtures thereof with CHF2CF?CHF. This process involves (a) reacting CHCl2CF2CF3, and optionally CHClFCF2CClF2, with H2 in the presence of a catalytically effective amount of a hydrogenation catalyst to form CH3CF2CF3 and, when CHClFCF2CClF2 is present, CH2FCF2CHF2; (b) dehydrofluorinating CH3CF2CF3, and optionally any CH2FCF2CHF2, from (a) to form a product mixture including CF3CF?CH2 and, if CH2FCF2CHF2 is present, CHF2CF?CHF; and optionally (c) recovering CF3CF?CH2, or a mixture thereof with CHF2CF?CHF from the product mixture formed in (b) and/or (d) separating at least a portion of any CHF2CF?CHF in the product mixture formed in (b) from the CF3CF?CH2 in the product mixture formed in (b).
    Type: Grant
    Filed: October 31, 2007
    Date of Patent: March 13, 2012
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Mario Joseph Nappa, Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
  • Publication number: 20120059200
    Abstract: Disclosed is an integrated manufacturing process to co-produce (E)1-chloro-3,3,3-trifluoropropene, (E)1,3,3,3-tetrafluoropropene, and 1,1,1,3,3-pentafluoro-propane starting from a single chlorinated hydrocarbon feed stock, 240fa. The process includes a combined liquid or vapor phase reaction/purification operation which directly produces (E)1-chloro-3,3,3-trifluoropropene (1233zd(E)) from 240fa. In the second liquid phase fluorination reactor 1233zd(E) is contacted with HF in the presence of catalyst to produce 1,1,1,3,3-pentafluoropropane (245fa) with high conversion and selectivity. A third reactor is used for dehydrofluorination of 245fa to produce (E)1,3,3,3-tetrafluoropropene (1234ze(E)) by contacting in the liquid phase with a caustic solution or in the vapor phase using a dehydrofluorination catalyst. This operation may be followed by one or more purification processes to recover the 1234ze(E) product.
    Type: Application
    Filed: August 29, 2011
    Publication date: March 8, 2012
    Inventors: Konstantin A. Pokrovski, Daniel C. Merkel, Haiyou Wang, Hsueh Sung Tung, Ian Shankland
  • Publication number: 20120059199
    Abstract: Disclosed is process for the production of (E) 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd(E)) by conducting a continuous reaction without the use of a catalyst. Also disclosed is an integrated system for producing hydrofluoro olefins, particularly 1233zd(E). The manufacturing process includes six major unit operations: (1) a fluorination reaction of HCC-240fa (in continuous or semi-batch mode) using HF with simultaneous removal of by-product HCl and the product 1233zd(E); (2) recycle of unreacted HCC-240fa and HF together with under-fluorinated by-products back to (1); (3) separation and purification of by-product HCl; (4) separation of excess HF back to (1); (5) purification of final product, 1233zd(E); and (6) isomerization of by-product 1233zd(Z) to 1233zd(E) to maximize the process yield.
    Type: Application
    Filed: August 29, 2011
    Publication date: March 8, 2012
    Inventors: Konstantin A. Pokrovski, Daniel C. Merkel, Hsueh Sung Tung
  • Publication number: 20120059202
    Abstract: In this invention we are disclosing a process for the synthesis of hydrocchlorofluoro olefins (HCFO) and/or hydrofluoroolefins (HFO). The process is based on the gas phase, noncatalytic fluorination of hydrochlorofluoropropenes to form hydrofluoropropenes.
    Type: Application
    Filed: November 16, 2011
    Publication date: March 8, 2012
    Applicant: Arkema Inc.
    Inventors: Maher Y. Elsheikh, Philippe Bonnet, Benjamin Bin Chen
  • Publication number: 20120053372
    Abstract: The invention is directed to a ternary azeotrope-like mixture consisting essentially of effective amounts of 1,1,1,3,3-pentafluoropropane, 1-chloro-3,3,3-trifluoropropene, and hydrogen fluoride.
    Type: Application
    Filed: November 7, 2011
    Publication date: March 1, 2012
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: RYAN HULSE, RAJIV R. SINGH, HSUEH S. TUNG, IAN SHANKLAND
  • Publication number: 20120041239
    Abstract: The present invention provides an effective, selective, and industrially applicable process for producing 2,3,3,3-tetrafluoropropene. Specifically, the present invention provides a process for producing 2,3,3,3-tetrafluoropropene including reacting 2-chloro-3,3,3-trifluoropropene with hydrogen fluoride in the presence of oxygen and a catalyst comprising chromium oxide represented by the composition formula: CrOm (1.5<m<3), or fluorinated chromium oxide obtained by fluorinating the chromium oxide.
    Type: Application
    Filed: April 22, 2010
    Publication date: February 16, 2012
    Inventors: Atsushi Suzuki, Masatoshi Nose, Tsuneo Yamashita
  • Publication number: 20120022303
    Abstract: The present invention provides a process for preparing 2-chloro-3,3,3-trifluoropropene including subjecting, in the absence of a catalyst, at least one chlorine-containing compound selected from the group consisting of chloropropane represented by formula (1): CClX2CHClCH2Cl, wherein each X is the same or different and each represents Cl or F, chloropropene represented by formula (2): CClY2CCl?CH2, wherein each Y is the same or different and each represents Cl or F, and chloropropene represented by formula (3): CZ2?CClCH2Cl, wherein each Z is the same or different and each represents Cl or F, to a reaction with hydrogen fluoride under heating in a gas phase. According to the present invention, 2-chloro-3,3,3-trifluoropropene (HCFC-1233xf) can be effectively prepared by an easy and economically advantageous process that is suitable for industrial scale production.
    Type: Application
    Filed: April 21, 2010
    Publication date: January 26, 2012
    Inventors: Masatoshi Nose, Atsushi Suzuki, Tsuneo Yamashita, Kenichi Katsukawa
  • Publication number: 20110319681
    Abstract: The object is to provide a process for producing highly pure 2,3,3,3-tetrafluoropropene, whereby formation of 3,3,3-trifluoropropene as a by-product is suppressed. A process for producing 2,3,3,3-tetrafluoropropene, which comprises introducing and reacting a raw material compound composed of at least one of 1,1-dichloro-2,3,3,3-tetrafluoropropene and 1-chloro-2,3,3,3-tetrafluoropropene, and hydrogen, in a catalyst layer packed with a catalyst-supporting carrier, wherein the temperature of the catalyst layer is controlled to be higher than the dew point of the raw material mixed gas comprising the raw material compound and the hydrogen, and the maximum temperature of the catalyst layer is maintained to be at most 130° C. during the reaction.
    Type: Application
    Filed: June 23, 2011
    Publication date: December 29, 2011
    Applicant: ASAHI GLASS COMPANY, LIMITED
    Inventors: Satoshi KAWAGUCHI, Hidekazu Okamoto, Yu Takeuchi, Hirokazu Takagi, Kunio Watanabe, Koichi Yanase
  • Patent number: 8076521
    Abstract: In this invention we are disclosing a process for the synthesis of hydrochlorofluoro olefins (HCFO) and/or hydrofluoroolefins (HFO). The process is based on the following steps of liquid phase, noncatalytic fluorination of hydrochloropropenes to form hydrochlorofluoropropenes and/or hydrofluoropropenes, followed by gas phase, catalytic fluorination of the hydrochlorofluoropropenes to form hydrofluoropropenes.
    Type: Grant
    Filed: June 26, 2008
    Date of Patent: December 13, 2011
    Assignee: Arkema Inc.
    Inventors: Maher Y. Elsheikh, Philippe Bonnet, Benjamin Bin Chen
  • Patent number: 8053613
    Abstract: A process is disclosed for making CH2ClCF2CClF2. The process involves reacting CH2ClF with CClF?CF2 in an addition reaction zone in the presence of an aluminum halide composition having a bulk formula of AlClxBryF3-x-y wherein the average value of x is 0 to 3, the average value of y is 0 to 3?x, provided that the average values of x and y are not both 0. Also disclosed is a process for making CH2FCF2CF3 that involves reacting the CH2ClCF2CClF2 with HF in a fluorination reaction zone in the presence of a fluorination catalyst. Also disclosed is a process for making CHF?CFCF3 that involves dehydrofluorinating the CH2FCF2CF3.
    Type: Grant
    Filed: September 5, 2007
    Date of Patent: November 8, 2011
    Assignee: E.I. du Pont de Nemours and Company
    Inventor: Allen Capron Sievert
  • Publication number: 20110245548
    Abstract: The present invention achieves a catalyst life improvement for the catalyzed vapor phase fluorination of a chlorocarbon in the presence of one catalyst and an oxygen feed. Specifically, in one non-limiting embodiment, the instant invention provides the conversion of 1,1,2,3-tetrachloropropene and/or 1,1,1,2,3-pentachloropropane to 2-chloro-3,3,3-trifluoropropene by introduction of a catalyst and oxygen co-feed to the fluorination reactor.
    Type: Application
    Filed: March 8, 2011
    Publication date: October 6, 2011
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: DANIEL C. MERKEL, KONSTANTIN A. POKROVSKI, HSUEH S. TUNG
  • Publication number: 20110207975
    Abstract: A method for preparing 2,3,3,3-tetrafluoroprop-1-ene comprising (a) providing a starting composition comprising at least one compound having a structure selected from Formulae I, II and III: CX2?CCl—CH2X??(Formula I) CX3—CCl?CH2??(Formula II) CX3—CHCl—CH2X??(Formula III) wherein X is independently selected from F, Cl, Br, and I, provided that at least one X is not fluorine; (b) contacting said starting composition with a first fluorinating agent to produce a first intermediate composition comprising 2-chloro-3,3,3-trifluoropropene and a first chlorine-containing byproduct; (c) contacting said first intermediate composition with a second fluorinating agent to produce a second intermediate composition comprising 2-chloro-1,1,1,2-tetrafluoropropane and a second chlorine-containing byproduct; and (d) catalytically dehydrochlorinating at least a portion of said 2-chloro-1,1,1,2-tetrafluoropropane to produce a reaction product comprising 2,3,3,3-tetrafluoroprop-1-ene.
    Type: Application
    Filed: March 13, 2009
    Publication date: August 25, 2011
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Daniel C. Merkel, Hsueh Sung Tung, Konstantin A. Pokrovski, Selma Bektesevic, Robert Johnson, Haiyou Wang
  • Publication number: 20110196178
    Abstract: Compositions including chlorinated propenes and a phenolic antioxidant are described herein.
    Type: Application
    Filed: April 9, 2008
    Publication date: August 11, 2011
    Inventor: Janice M. Nyberg
  • Publication number: 20110178344
    Abstract: The present invention provides a process for producing 2,3,3,3-tetrafluoropropene represented by the formula CF3CF?CH2, comprising contacting a fluorine-containing propane represented by the formula CF2XCFYCH2Z, wherein X is Cl, Br, or I; one of Y and Z is H, and the other is F, Cl, Br, or I, with at least one catalyst selected from the group consisting of chromium oxides, fluorinated chromium oxides, and iron fluorides in a gas phase. According to the process of the invention, 2,3,3,3-tetrafluoropropene can be easily produced under economically advantageous conditions.
    Type: Application
    Filed: July 24, 2009
    Publication date: July 21, 2011
    Inventors: Masatoshi Nose, Daisuke Karube, Akinari Sugiyama, Takashi Shibanuma, Takehiro Chaki
  • Publication number: 20110178343
    Abstract: The present invention provides one-step processes for the production of chlorinated and/or fluorinated propenes. The processes provide good product yield with low, e.g., less than about 20%, or even less than 10%, concentrations of residues/by-products. Advantageously, the processes may be conducted at low temperatures relative to conventional processes, so that energy savings are provided, and/or at higher pressures so that high throughputs may also be realized. The use of catalysts may provide enhancements to conversion rates and selectivity over those seen in conventional processes, as may adjustments to the molar ratio of the reactants.
    Type: Application
    Filed: April 20, 2010
    Publication date: July 21, 2011
    Applicant: DOW GLOBAL TECHNOLOGIES, INC.
    Inventors: William J. Kruper, JR., Max M. Tirtowidjojo, Kurt F. Hirsekorn, Debashis Chakraborty, Juergen Eiffler
  • Publication number: 20110172472
    Abstract: According to the first characteristic of the present invention, there is provided a production process for 1,3,3,3-tetrafluoropropene including: the first step of reacting 1,1,1,3,3-pentachloropropane with hydrogen fluoride thereby obtaining 1-chloro-3,3,3-trifluoropropene; and the second step of reacting 1-chloro-3,3,3-trifluoropropene obtained in the first step with hydrogen fluoride in a gaseous phase in the presence of a fluorination catalyst. According to the second characteristic of the present invention, there is provided a dehydration process including bringing 1,3,3,3-tetrafluoropropene containing at least water into contact with zeolite.
    Type: Application
    Filed: September 24, 2009
    Publication date: July 14, 2011
    Applicant: Central Glass Company, Limited
    Inventors: Fuyuhiko Sakyu, Satoshi Yoshikawa, Satoru Okamoto, Yasuo Hibino, Yoshio Nishiguchi
  • Publication number: 20110155942
    Abstract: The invention is directed to a process for preparing 2,2,2,3-tetrafluoropropene (1234yf), comprising: (i) contacting 1,1,2,3-tetrachloropropene (1230xa) with hydrogen fluoride HF in gas phase in the presence of a fluorination catalyst under conditions sufficient to produce a reaction mixture; (ii) separating the reaction mixture into a first stream comprising HCl, 2,2,2,3-tetrafluoropropene (1234yf) and a second stream comprising HF, 2-chloro-3,3,3-trifluoro-1-propene (1233xf) and 1,1,1,2,2-pentafluoropropane (245cb); (iii) recycling at least a part of the second stream at least in part back to step (i).
    Type: Application
    Filed: December 23, 2010
    Publication date: June 30, 2011
    Applicant: Arkema France
    Inventors: Anne Pigamo, Dominique Deur-Bert, Laurent Wendlinger
  • Publication number: 20110130599
    Abstract: A one reactor, gas phase catalyzed process for the fluorination of 1,1,2,3-tetrachloropropene (1230xa) to produce 1,1,1,2-tetrafluoropropene (1234yf) is disclosed. The process of the present invention is a catalytic, gas phase fluorination using a high pressure activated catalyst which is supported or unsupported. Fluorination products of the formula CF3R, where R is selected from —CCl=CH2, —CF=CH2, —CF2—CH3, —CFCl—CH3 and mixtures thereof are produced. Co-produced materials are separated from the desired product and recycled to the same reactor.
    Type: Application
    Filed: June 23, 2009
    Publication date: June 2, 2011
    Applicant: Arkema Inc
    Inventors: Maher Y. Elsheikh, Philippe Bonnet
  • Publication number: 20110087055
    Abstract: The present invention provides continuous, gas phase, free radical processes for the production of chlorinated and/or fluorinated propenes or higher alkenes from the reaction of chlorinated and/or fluorinated alkanes and chlorinated and/or fluorinated alkenes, wherein wherein at least a portion of any intermediate boiler by-products generated by the process are removed from the process
    Type: Application
    Filed: October 8, 2010
    Publication date: April 14, 2011
    Applicant: DOW GLOBAL TECHNOLOGIES
    Inventors: Max M. Tirtowidjojo, Patrick H. Au-Yeung, Debashis Chakraborty, Juergen Eiffler, Heinz Groenewald, Kurt F. Hirsekorn, Manfred Kokott, William J. Kruper, JR., Thomas U. Luebbe, Holger Meeman, Shirley S. Sexton, Peter Wenzel, Marcus Wobser
  • Publication number: 20100204529
    Abstract: The present invention provides a simple and efficient process for producing 2,3,3,3-tetrafluoropropene(HFC-1234yf), the process being useful for industrial production. More specifically, the present invention relates to: a process for producing 2,3,3,3-tetrafluoropropene, comprising the steps of: (I) reacting a compound expressed by Formula (1): CF3CF2CH2X ??(1) wherein X represents Cl, Br or I, with a base to produce a compound expressed by Formula (2): CF3CF?CHX ??(2) wherein X is the same as above; and (II) reducing the compound expressed by Formula (2) with hydrogen in the presence of a catalyst to produce 2,3,3,3-tetrafluoropropene.
    Type: Application
    Filed: September 10, 2008
    Publication date: August 12, 2010
    Inventors: Junpei Terada, Takuji Ishikawa
  • Publication number: 20100185030
    Abstract: In this invention we are disclosing a process for the synthesis of hydrochlorofluoro olefins (HCFO) and/or hydrofluoroolefins (HFO). The process is based on the following steps of liquid phase, noncatalytic fluorination of hydrochloropropenes to form hydrochlorofluoropropenes and/or hydrofluoropropenes, followed by gas phase, catalytic fluorination of the hydrochlorofluoropropenes to form hydrofluoropropenes.
    Type: Application
    Filed: June 26, 2008
    Publication date: July 22, 2010
    Applicant: Arkema Inc.
    Inventors: Maher Y. Elsheikh, Philippe Bonnet, Benjamin Bin Chen
  • Publication number: 20100160696
    Abstract: Disclosed is a process for the preparation of fluorine-containing olefins comprising contacting a chlorofluoroalkene with hydrogen in the presence of a catalyst at a temperature sufficient to cause replacement of the chlorine substituents of the chlorofluoroalkene with hydrogen to produce a fluorine-containing olefin, wherein said catalyst is a composition comprising chromium, nickel and optionally an alkali metal selected from potassium and cesium. Also disclosed are catalyst compositions for the hydrodechlorination of chlorofluoroalkenes comprising copper, nickel, and an alkali metal selected from potassium and cesium, and methods of making such catalysts.
    Type: Application
    Filed: December 18, 2009
    Publication date: June 24, 2010
    Applicant: E. I. DU PONT DE NEMOURS AND COMPANY
    Inventors: MARIO JOSEPH NAPPA, Ekaterina N. Swearingen
  • Publication number: 20100072415
    Abstract: A process is disclosed for making CF3CF2CH3, CF3CF?CH2 and/or CF3CCl?CH2. The process involves reacting at least one starting material selected from the group consisting of halopropanes of the formula CX3CHClCH2X, halopropenes of the formula CClX2CCl?CH2 and halopropenes of the formula CX2?CClCH2X, wherein each X is independently F or Cl, with HF in a reaction zone to produce a product mixture comprising HF, HCl, CF3CF2CH3, CF3CF?CH2 and CF3CCl?CH2; and recovering the CF3CF2CH3, CF3CF?CH2 and/or CF3CCl?CH2 from the product mixture. Also disclosed is a process for making CF3CH2CHF2, CF3CH?CHF and/or CF3CH?CHCl.
    Type: Application
    Filed: October 31, 2007
    Publication date: March 25, 2010
    Applicant: E.I. DU PONT DE NEMOURS AND COMPANY
    Inventors: Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
  • Publication number: 20100048961
    Abstract: The invention provides a method for separating halocarbons. In particular, a method for separating 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) from 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) based on differences in melting points of these compounds. More particularly the invention pertains to a method for separating HCFC-244bb from HCFO-1233xf which are useful as intermediates in the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf).
    Type: Application
    Filed: August 12, 2009
    Publication date: February 25, 2010
    Inventors: Daniel C. Merkel, Hsueh Sung Tung, Konstantin A. Pokrovski
  • Publication number: 20090240090
    Abstract: A method for preparing 2,3,3,3-tetrafluoroprop-1-ene comprising (a) providing a starting composition comprising at least one compound having a structure selected from Formulae I, II and III: CX2?CCl—CH2X??(Formula I) CX3—CCl?CH2??(Formula II) CX3—CHCl—CH2X??(Formula III) wherein X is independently selected from F, Cl, Br, and I, provided that at least one X is not fluorine; (b) contacting said starting composition with a first fluorinating agent to produce a first intermediate composition comprising 2-chloro-3,3,3-trifluoropropene and a first chlorine-containing byproduct; (c) contacting said first intermediate composition with a second fluorinating agent to produce a second intermediate composition comprising 2-chloro-1,1,1,2-tetrafluoropropane and a second chlorine-containing byproduct; and (d) catalytically dehydrochlorinating at least a portion of said 2-chloro-1,1,1,2-tetrafluoropropane to produce a reaction product comprising 2,3,3,3-tetrafluoroprop-1-ene.
    Type: Application
    Filed: March 13, 2009
    Publication date: September 24, 2009
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Daniel C. Merkel, Hsueh Sung Tung, Konstantin A. Pokrovski, Selma Bektesevic, Robert Johnson, Haiyou Wang
  • Publication number: 20090216053
    Abstract: Disclosed is a process for producing hexafluoro-1,3-butadiene, which is used for an etching gas capable of being used in fine processing for semiconductors, safely in industrialization and at low cost economically. Specifically disclosed is a process for producing hexafluoro-1,3-butadiene comprises (1) a step comprising allowing a compound having four carbon atoms each which bonds to an atom selected from the group consisting of a bromine atom, an iodine atom and a chlorine atom, to react with a fluorine gas in the presence of a diluting gas in a gas phase, thereby preparing a mixture containing a product (A), and (2) a step comprising eliminating halogens excluding a fluorine atom with a metal from the product (A) prepared in the step (1) in the presence of a solvent, thereby preparing a mixture containing hexafluoro-1,3-butadiene.
    Type: Application
    Filed: April 25, 2007
    Publication date: August 27, 2009
    Applicant: Showa Denko K.K.
    Inventors: Hiromoto Ohno, Toshio Ohi
  • 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: 20090099396
    Abstract: Disclosed is a process for the synthesis of fluorinated olefins, and in particularly preferred embodiments tetrafluorinated olefins having F on an unsaturated, non-terminal carbon, such as 2,3,3,3-tetrafluoropropene. The preferred processes of the present invention in accordance with one embodiment generally comprise: (a) reacting a compound of formula (I) X1X2??(I) with a compound of formula (II) CX1X2X3CX1?CX1X2??(II) to produce a reaction product comprising a compound of formula (III) CF3CHX1CH2X2??(III), and (b) exposing said compound of formula (III) to reaction conditions effective to convert said compound of formula (III) to a compound of formula (IV) CF3CZ=CH2??(IV) wherein X1, X2, and X3 are each independently selected from the group consisting of hydrogen, chlorine, bromine, fluorine and iodine, provided that X1 and X2 in formula (I) are not both hydrogen and Z is Cl, I, Br, or F.
    Type: Application
    Filed: October 12, 2008
    Publication date: April 16, 2009
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Sudip Mukhopadhyay, Cheryl L. Bortz, Barbara A. Light, Cheryl L. Cantlon, Robert C. Johnson
  • Patent number: 7319174
    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: Grant
    Filed: September 25, 2006
    Date of Patent: January 15, 2008
    Assignee: 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: 7294747
    Abstract: Process for the manufacture of 1,1-difluoroethane by liquid-phase fluorination of 1,2-dichloroethane using hydrofluoric acid in the presence of a Lewis acid as catalyst and of FeCl3 as cocatalyst. Process for the manufacture of 1,1-difluoroethylene employing it.
    Type: Grant
    Filed: October 17, 2003
    Date of Patent: November 13, 2007
    Assignee: Arkema France
    Inventor: Phillipe Bonnet
  • Patent number: 7189884
    Abstract: Disclosed in one embodiment is a process for the synthesis of 1,3,3,3-tetrafluoropropene that comprises (a) reacting a compound of formula (I) X1X2 with a compound of formula (II) CF3CH?CH2 to produce a reaction product comprising a compound of formula (III) CF3CHX1CH2X2, wherein X1 and X2 are each independently selected from the group consisting of hydrogen, chlorine, bromine and iodine, provided that X1 and X2 are not both hydrogen; (b) when X2 in formula (III) is not fluorine, fluorinating the compound of formula (III) to produce a reaction product comprising a compound of formula (III) wherein X1 is as described above and X2 is fluorine; and (c) exposing said compound of formula (III) to reaction conditions effective to convert said compound to 1,3,3,3-tetrafluoropropene.
    Type: Grant
    Filed: April 29, 2005
    Date of Patent: March 13, 2007
    Assignee: Honeywell International
    Inventors: Sudip Mukhopadhyay, Haridasan K. Nair, HsuehSung Tung, Michael Van Der Puy
  • Patent number: 6395940
    Abstract: The invention relates to a method for producing a first perhalogenated cyclopentene represented by the general formula: C5ClBF8−B where B is an integer of from 0 to 7. The method includes a step of (a) fluorinating a second perhalogenated cyclopentene by hydrogen fluoride in a gas phase in the presence of a fluorination catalyst. The second perhalogenated cyclopentene is represented by general formula: C5ClAF8−A where A is an integer of from 1 to 8, and A is not smaller than B. With this method, the first perhalogenated cyclopentene (e.g., 1,2-dichloro-3,3,4,4,5,5-hexafluorocyclopentene, another chlorofluorinated cyclopentene, or octafluorocyclopentene) can continuously easily be produced, for example, from octachlorocyclopentene obtained by chlorination of hexachlorocyclopentadiene that is easily available. Therefore, the above method is very useful as an industrial scale production method.
    Type: Grant
    Filed: March 1, 2000
    Date of Patent: May 28, 2002
    Assignees: Central Glass Company, Limited, Nippon Zeon Co., Ltd.
    Inventors: Takeo Komata, Takayuki Nishimiya, Fuyuhiko Sakyu, Hideaki Imura, Mikio Ujiie, Masatomi Kanai
  • Publication number: 20020022752
    Abstract: The invention provides a process for producing a fluorine-containing compound from an inexpensive material.
    Type: Application
    Filed: September 24, 2001
    Publication date: February 21, 2002
    Applicant: ASAHI GLASS COMPANY, LIMITED
    Inventors: Takashi Okazoe, Kunio Watanabe, Shin Tatematsu, Hidenobu Murofushi
  • Patent number: 6211420
    Abstract: In a process for preparing a fluorinated olefin having a carbon—carbon double bond, the carbon atoms of which have a fluorine atom, by reacting a halogenated olefin having at least one carbon—carbon double bond, a carbon atom or the carbon atoms of which bond have a chlorine atom or atoms bound thereto, and, in which the carbon atom or atoms with a single bond in the molecule have no halogen atom other than a fluorine atom, with an alkali metal fluoride, said reaction of the halogenated olefin with the alkali metal fluoride is conducted in the presence of an organic halogen-containing compound having a carbon—carbon single bond, a carbon or the carbons of which have at least one halogen atom other than fluorine atom.
    Type: Grant
    Filed: November 13, 1998
    Date of Patent: April 3, 2001
    Assignee: Japan as represented by Director General of Agency of Industrial Science and Technology
    Inventors: Akira Sekiya, Toshiro Yamada, Mitsuru Sugawara
  • Patent number: 6211421
    Abstract: An uncatalyzed liquid phase process is provided for producing 1,1,1-trifluoropropene via the fluorination of 1,1,3-trichloro-1-propene.
    Type: Grant
    Filed: September 26, 2000
    Date of Patent: April 3, 2001
    Assignee: Atofina Chemicals, Inc.
    Inventors: Maher Y. Elsheikh, Bin Chen
  • Patent number: 6166274
    Abstract: A liquid phase process is provided for the preparation of 1233zd with reduced oligomer formation via the fluorination of 1230za with HF in the presence of a catalyst selected from TFA and triflic acid. The 1233zd is a known intermediate useful for preparing 245fa.
    Type: Grant
    Filed: December 15, 1999
    Date of Patent: December 26, 2000
    Assignee: ATOFINA Chemicals, Inc.
    Inventors: Bin Chen, Michael S. Bolmer, Maher Y. Elsheikh
  • Patent number: 5969197
    Abstract: Avoiding hexachlorobutadiene as the starting material, 2-chloro- and 2,3-dichloro-1,1,1,4,4,4-hexafluoro-2-butene are prepared by reacting a chlorobutene derivative of the formula (I)Cl.sub.2 C.dbd.CH-X (I)in whichX represents CCl.dbd.CCl.sub.2 or CCl.sub.2 --CCl.sub.2 H with hydrogen fluoride and chlorine in the presence of a catalyst at temperatures in the range of 50 to 550.degree. C.
    Type: Grant
    Filed: June 9, 1994
    Date of Patent: October 19, 1999
    Assignee: Bayer Aktiengesellschaft
    Inventors: Norbert Lui, Albrecht Marhold, Dietmar Bielefeldt
  • Patent number: 5919993
    Abstract: At least one halogenated compound selected from the group consisting of 1,1,1,4,4,4-hexafluoro-2,3-dichlorobutane, 1,1,1,4,4,4-hexafluoro-2-chloro-2-butene, 1,1,1,2,4,4,4-heptafluoro-2-butene and 1,1,1,2,2,4,4,4-octafluorobutane, is prepared by reacting 1,1,2,3,4,4-hexachloro-1,3-butadiene with hydrogen fluoride in a gas phase in the presence of a fluorinating catalyst. Desired products can be prepared commercially according to the present invention.
    Type: Grant
    Filed: September 3, 1993
    Date of Patent: July 6, 1999
    Assignee: Daikin Industries Ltd.
    Inventors: Tatsuo Nakada, Hirokazu Aoyama, Satoshi Koyama
  • Patent number: 5877359
    Abstract: An uncatalyzed liquid phase process is provided for the preparation of oligomer free 1233zd via the fluorination of 1230za with a high molar excess of HF. The 1233zd is a known intermediate useful for preparing 245fa.
    Type: Grant
    Filed: January 27, 1998
    Date of Patent: March 2, 1999
    Assignee: Elf Atochem North America, Inc.
    Inventor: Maher Y. Elsheikh
  • Patent number: 5847243
    Abstract: A vic-dichloro-fluorinated alkene of the formula: R.sup.1 --CCl.dbd.CCl--R.sup.2, and a fluorinated alkane of the formula: R.sup.1 --CR.sup.3 R.sup.4 --CR.sup.5 R.sup.6 --R.sup.2, wherein each of R.sup.1 and R.sup.2 independently represents a perfluoroalkyl group or both of R.sup.1 and R.sup.2 form together a perfluoroalkylene group, and R.sup.3, R.sup.4, R.sup.5 and R.sup.6 independently represent hydrogen or fluorine, are produced from an inexpensive raw material. More specifically, hexachlorocyclopentadiene is reacted with gaseous chlorine using an antimony catalyst, and then the reaction product is reacted with hydrogen fluoride to give 1,2-dichlorohexafluorocyclopentene. Thus-obtained compound is either (i) hydrogenated, or (ii) treated with a fluorinating agent to substitute the chlorine atoms by fluorine atoms, and then hydrogenated, to give the intended fluorinated alkane.
    Type: Grant
    Filed: December 27, 1996
    Date of Patent: December 8, 1998
    Assignees: Japan as represented by Director General of the Agency of Industrial Science and Technology, Nippon Zeon Co. Ltd.
    Inventors: Akira Sekiya, Toshiro Yamada, Kazunori Watanabe
  • Patent number: 5714655
    Abstract: 2,2,3-trichloro-1,1,1,3,3-pentafluoropropane is used as a raw material, to which not less than 4.5 equivalent parts of hydrogen are added to effect a hydrogenation reaction in the presence of a noble metal catalyst, particularly a palladium catalyst, by the vapor phase method to manufacture 1,1,1,3,3-pentafluoropropane. Further, propane, propene, and hexachloropropene, etc. are chlorofluorinated in the presence of a metal catalyst to produce 2,2,3-trichloro-1,1,1,3,3-pentafluoropropane, then this compound is reduced with hydrogen in the presence of a noble metal catalyst to produce 1,1,1,3,3-pentafluoropropane. 2,2,3-trichloro-1,1,1,3,3-pentafluoropropane and 1,1,1,3,3-pentafluoropropane can thus be efficiently and economically produced.
    Type: Grant
    Filed: December 8, 1995
    Date of Patent: February 3, 1998
    Assignee: Daikin Industries, Ltd.
    Inventors: Akinori Yamamoto, Eiji Seki, Hirokazu Aoyama, Seiji Takubo, Tatsuo Nakada
  • Patent number: 5345016
    Abstract: This invention provides an improved process for the manufacture of 1,1,1,2-tetrafluoroethane by the reaction of HF and trichloroethylene in the presence of a catalyst to form a mixture comprising 2-chloro-1,1,1-trifluoroethane and 1,1,1,2-tetrafluoroethane and, optionally, other organic by-products. The improvement resides in conducting the reaction in a single reaction zone while recovering the 1,1,1,2-tetrafluoroethane from the mixture and recycling the 2-chloro-1,1,1-trifluoroethane and, optionally, other organic by-products from the mixture to the reaction along with trichloroethylene and HF.
    Type: Grant
    Filed: February 4, 1993
    Date of Patent: September 6, 1994
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Leo E. Manzer
  • Patent number: 5334788
    Abstract: Substrate compounds are reacted by passing them through an eductor with fluorine gas optionally in the presence of a liquid medium and preferably in a loop reactor with cooling means thereby providing rapid but controlled reaction suitable for industrial scale production. Vinylidene chloride, for example, smoothly produces dichlorodifluoroethane and dichlorotrifluoroethane in good yield.
    Type: Grant
    Filed: May 1, 1992
    Date of Patent: August 2, 1994
    Assignee: PCR Group, Inc.
    Inventors: Keith B. Baucom, Adam C. Alty, Earl J. Kimmel
  • Patent number: 5233105
    Abstract: Bismuth/alkaline earth metal catalysts which contain 0.005-0.8 g-atom of bismuth per mol of the alkaline earth metal compound employed and can furthermore contain promoters and/or inert additives, and lanthanide catalysts with or without catalyst supports can be employed as catalysts for halogen-fluorine exchange in organic compounds by means of hydrogen fluoride.
    Type: Grant
    Filed: October 25, 1990
    Date of Patent: August 3, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Helmut Schwarz, Rudolf Braden
  • Patent number: 5210340
    Abstract: 1,1,1,2,4,4,4-Heptafluoro-2-butene and 2-chloro-1,1,1,4,4,4-hexafluoro-2-butene 1,V5VjV9are prepared simultaneously by reacting hexachlorobutadiene with hydrogen fluoride with the addition of catalytic amounts of titanium halide, antimony trihalide and/or antimony pentahalide.
    Type: Grant
    Filed: April 10, 1992
    Date of Patent: May 11, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Dietmar Bielefeldt, Albrecht Marhold