By Reacting With Hydrogen Fluoride Patents (Class 570/164)
  • Patent number: 10550054
    Abstract: An azeotropic or quasi-azeotropic composition including hydrogen fluoride, 3,3,3-trifluoropropene and one or more (hydro)halogen-carbon compounds including between 1 and 3 carbon atoms. Also, a preferred azeotropic or quasi-azeotropic composition including hydrogen fluoride, 3,3,3-trifluoropropene, and one or more compounds selected from among 1,1,1,2,2-pentafluoropropane, 2,3,3,3-tetrafluoropropene, 1,3,3,3-tetrafluoropropene, 3,3,3-trifluoro-2-chloropropene, E-3,3,3-trifluoro-l-chloropropene, trifluoropropyne, 1,1,1,3,3-pentafluoropropane, 1,1,1,3,3-pentafluoropropane, 1,1,1,3,3-pentafluoropropene, 1,1,1,2,3-pentafluoropropene and 2-chloro, 1,1,1,2-tetrafluoropropane.
    Type: Grant
    Filed: February 24, 2014
    Date of Patent: February 4, 2020
    Assignee: ARKEMA FRANCE
    Inventors: Philippe Bonnet, Bertrand Collier, Dominique Deur-Bert, Laurent Wendlinger
  • Patent number: 10450248
    Abstract: A method for producing 1,3,3,3-tetrafluoropropene (HFO-1234ze, or 1234ze) from 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd, or 1233zd). In one embodiment, HFO-1233zd is subjected to a disproportionation reaction in the presence of a catalyst at an elevated temperature to produce HFO-1234ze as well as 3,3-dichloro-1,1-difluoropropene (HCFO-1232zc). The catalyst may be at least one of a chromium oxyfluoride catalyst, a chromium oxide catalyst, or a metal fluoride catalyst. The reaction may be conducted in the vapor phase at a temperature between 100° C. and 450° C. Advantageously, in the present method, substantially no hydrogen fluoride (HF) is used as a reactant, and substantially no HF is produced as a product.
    Type: Grant
    Filed: November 1, 2018
    Date of Patent: October 22, 2019
    Assignee: Honeywell International Inc.
    Inventors: Christian Jungong, Daniel C. Merkel, Haiyou Wang
  • Patent number: 10343963
    Abstract: An azeotropic or quasi-azeotropic composition including hydrogen fluoride, E-3,3,3-trifluoro-1-chloropropene and optionally one or more (hydro)halogen-carbon compounds including between 1 and 3 carbon atoms. Also, a preferred azeotropic or quasi-azeotropic composition including hydrogen fluoride, E-3,3,3-trifluoro-1-chloropropene, and optionally one or more compounds selected from among 1,1,1,2,2-pentafluoropropane, 2,3,3,3-tetrafluoropropene, 3,3,3-trifluoropropene, 3,3,3-trifluoro-2-chloropropene, 1,3,3,3-tetrafluoropropene, trifluoropropyne, 1,1,1,3,3-pentafluoropropane, 1,1,1,3,3-pentafluoropropane, 1,1,1,3,3-pentafluoropropene, 1,1,1,2,3-pentafluoropropene and 2-chloro,1,1,1,2-tetrafluoropropane.
    Type: Grant
    Filed: August 13, 2018
    Date of Patent: July 9, 2019
    Assignee: ARKEMA FRANCE
    Inventors: Philippe Bonnet, Bertrand Collier, Dominque Deur-Bert, Laurent Wendlinger
  • Patent number: 10252913
    Abstract: An azeotropic or quasi-azeotropic composition including hydrogen fluoride, 2,3,3,3-tetrafluoropropene and one or more (hydro)halogen-carbon compounds including between 1 and 3 carbon atoms. Also a azeotropic or quasi-azeotropic composition including hydrogen fluoride, 2,3,3,3-tetrafluoropropene, and one or more organic compounds selected from among 1,1,1,2,2-pentafluoropropane, E-1,3,3,3-tetrafluoropropene, Z-1,3,3,3-tetrafluoropropene, 3,3,3-trifluoropropene, 3,3,3-trifluoro-2-chloropropene, E-3,3,3-trifluoro-1-chloropropene, trifluoropropyne, 1,1,1,3,3-pentafluoropropane, 1,1,1,3,3-pentafluoropropene, Z-1,1,1,2,3-pentafluoropropene and 2-chloro,1,1,1,2-tetrafluoropropane.
    Type: Grant
    Filed: February 21, 2014
    Date of Patent: April 9, 2019
    Assignee: ARKEMA FRANCE
    Inventors: Philippe Bonnet, Bertrand Collier, Dominique Deur-Bert, Laurent Wendlinger
  • Patent number: 10077221
    Abstract: An azeotropic or quasi-azeotropic composition including hydrogen fluoride, E-3,3,3-trifluoro-1-chloropropene and optionally one or more (hydro)halogen-carbon compounds including between 1 and 3 carbon atoms. Also, a preferred azeotropic or quasi-azeotropic composition including hydrogen fluoride, E-3,3,3-trifluoro-1-chloropropene, and optionally one or more compounds selected from among 1,1,1,2,2-pentafluoropropane, 2,3,3,3-tetrafluoropropene, 3,3,3-trifluoropropene, 3,3,3-trifluoro-2-chloropropene, 1,3,3,3-tetrafluoropropene, trifluoropropyne, 1,1,1,3,3-pentafluoropropane, 1,1,1,3,3-pentafluoropropane, 1,1,1,3,3-pentafluoropropene, 1,1,1,2,3-pentafluoropropene and 2-chloro,1,1,1,2-tetrafluoropropane.
    Type: Grant
    Filed: February 21, 2014
    Date of Patent: September 18, 2018
    Assignee: ARKEMA FRANCE
    Inventors: Philippe Bonnet, Bertrand Collier, Dominique Deur-Bert, Laurent Wendlinger
  • Patent number: 10029963
    Abstract: An azeotropic or quasi-azeotropic composition including hydrogen fluoride, 1,3,3,3-tetrafluoropropene and one or more (hydro)halogen-carbon compounds including between 1 and 3 carbon atoms. Also, a preferred azeotropic or quasi-azeotropic composition comprising hydrogen fluoride, 1,3,3,3-tetrafluoropropene, and one or more compounds selected from among 1,1,1,2,2-pentafluoropropane, 2,3,3,3-tetrafluoropropene, 3,3,3-trifluoropropene, 3,3,3-trifluoro-2-chloropropene, E-3,3,3-trifluoro-1-chloropropene, trifluoropropyne, 1,1,1,3,3-pentafluoropropane, 1,1,3,3-pentafluoropropene, 1,1,1,3,3-pentafluoropropene, 1,1,1,2,3-pentafluoropropene and 2-chloro, 1,1,1,2-tetrafluoropropane.
    Type: Grant
    Filed: February 24, 2014
    Date of Patent: July 24, 2018
    Assignee: ARKEMA FRANCE
    Inventors: Philippe Bonnet, Bertrand Collier, Dominique Deur-Bert, Laurent Wendlinger
  • Patent number: 9914680
    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: Grant
    Filed: May 5, 2015
    Date of Patent: March 13, 2018
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Daniel C. Merkel, Robert C. Johnson, Hsueh Sung Tung
  • Patent number: 9682905
    Abstract: The present invention is directed to processes for the production of 1233zd from 240fa and HF, with or without a catalyst, at a commercial scale. The 240fa and HF are fed to a reactor operating at high pressure. The resulting product stream comprising 1233zd, HCl, HF, and other byproducts is treated to one or more purification techniques including phase separation and one or more distillations to provide purified 1233zd, which meets commercial product specifications, i.e., having a GC purity of 99.5% or greater.
    Type: Grant
    Filed: January 30, 2015
    Date of Patent: June 20, 2017
    Assignee: Honeywell International Inc.
    Inventors: Stephen A. Cottrell, Hsueh Sung Tung, Konstantin A. Pokrovski
  • Patent number: 9593058
    Abstract: An object of the present invention is to provide a production method that makes it possible to produce 1,1-dibromo-1-fluoroethane easily and sustainably. The present invention provides a method for producing 1,1-dibromo-1-fluoroethane, the method comprising step A of reacting 1,1-dibromoethylene with hydrogen fluoride to obtain 1,1-dibromo-1-fluoroethane.
    Type: Grant
    Filed: September 3, 2014
    Date of Patent: March 14, 2017
    Assignee: DAIKIN INDUSTRIES, LTD.
    Inventors: Atsushi Shirai, Masatoshi Nose, Yosuke Kishikawa, Tatsuya Ohtsuka, Sumi Ishihara
  • Patent number: 9255045
    Abstract: A production process for the production of E-1-chloro-3,3,3-trifluoropropene, the process including at least one stage during which 1,1,3,3 -tetrachloropropene reacts with anhydrous hydrofluoric acid in the liquid phase, in the absence of a catalyst, with an HF/1,1,3,3-tetrachloropropene molar ratio between 3 and 20 inclusive, at a temperature between 50° C. and 150° C. inclusive and an absolute pressure of between 1 and 20 bar inclusive.
    Type: Grant
    Filed: January 13, 2014
    Date of Patent: February 9, 2016
    Assignee: ARKEMA FRANCE
    Inventors: Anne Pigamo, John Wismer, Bertrand Collier, Philippe Bonnet
  • Patent number: 9227894
    Abstract: The present invention is directed to processes for the production of 1233zd from 240fa and HF, with or without a catalyst, at a commercial scale. The 240fa and HF are fed to a reactor operating at high pressure. The resulting product stream comprising 1233zd, HCl, HF, and other byproducts is treated to one or more purification techniques including phase separation and one or more distillations to provide purified 1233zd, which meets commercial product specifications, i.e., having a GC purity of 99.5% or greater.
    Type: Grant
    Filed: January 30, 2015
    Date of Patent: January 5, 2016
    Assignee: Honeywell International Inc.
    Inventors: Stephen A. Cottrell, Hsueh Sung Tung, Konstantin A. Pokrovski
  • Patent number: 9040760
    Abstract: This invention provides a process for producing 2,3,3,3-tetrafluoropropene, the process comprising: (1) a first reaction step of reacting hydrogen fluoride with at least one chlorine-containing compound selected from the group consisting of a chloropropane represented by Formula (1): CClX2CHClCH2Cl, wherein each X is the same or different and is CI or F, a chloropropene represented by Formula (2): CClY2CCl?CH2, wherein each Y is the same or different and is CI or F, and a chloropropene represented by Formula (3): CZ2?CClCH2Cl, wherein each Z is the same or different and is CI or F in a gas phase in the absence of a catalyst while heating; and (2) a second reaction step of reacting hydrogen fluoride with a reaction product obtained in the first reaction step in a gas phase in the presence of a fluorination catalyst while heating. According to the process of this invention, 2,3,3,3-tetrafluoropropene (HFO-1234yf) can be obtained with high selectivity, and catalyst deterioration can be suppressed.
    Type: Grant
    Filed: October 27, 2011
    Date of Patent: May 26, 2015
    Assignee: DAIKIN INDUSTRIES, LTD.
    Inventors: Kazuhiro Takahashi, Yuzo Komatsu, Akinori Ueda
  • Patent number: 9000240
    Abstract: The present invention is directed to processes for the production of 1233zd from 240fa and HF, with or without a catalyst, at a commercial scale. The 240fa and HF are fed to a reactor operating at high pressure. The resulting product stream comprising 1233zd, HCl, HF, and other byproducts is treated to one or more purification techniques including phase separation and one or more distillations to provide purified 1233zd, which meets commercial product specifications, i.e., having a GC purity of 99.5% or greater.
    Type: Grant
    Filed: May 15, 2012
    Date of Patent: April 7, 2015
    Assignee: Honeywell International Inc.
    Inventors: Stephen A. Cottrell, Hsueh Sung Tung, Konstantin A. Pokrovski
  • Publication number: 20150094502
    Abstract: The present invention provides a process of fluorination in liquid phase in a solvent medium of a compound of formula (II) CX1X2=CZCX3X4X5, in which Z represents H, Cl or F, and each X1 represents independently hydrogen or chlorine, given that at least one of the X1 represents a chlorine.
    Type: Application
    Filed: October 8, 2014
    Publication date: April 2, 2015
    Applicant: ARKEMA FRANCE
    Inventor: Anne PIGAMO
  • Patent number: 8921621
    Abstract: A process for the manufacture of 1-chloro-3,3,3-trifluoropropene (HCFC-1233zd) at commercial scale from the reaction of HCC-240 and HF is disclosed. In one embodiment, HCC-240fa and HF are fed to a reactor operating at high pressure. Several different reactor designs useful in this process include; a stirred-tank reactor (batch and/or continuous flow); a plug flow reactor; a static mixer used as a reactor; at least one of the above reactors operating at high pressure; optionally combined with a distillation column running at a lower pressure; and combinations of the above; and/or with a distillation column. The resulting product stream consisting of 1233zd, HCl, HF, and other byproducts is partially condensed to recover HF by phase separation. The recovered HF phase is recycled to the reactor. The HCl is scrubbed from the vapor stream and recovered as an aqueous solution.
    Type: Grant
    Filed: February 4, 2013
    Date of Patent: December 30, 2014
    Assignee: Honeywell International Inc.
    Inventors: Stephen A. Cottrell, Hsueh Sung Tung, Konstantin A. Pokrovski, Haiyou Wang, Daniel C. Merkel
  • Patent number: 8912369
    Abstract: A production method of 1-chloro-3,3,3-trifluoropropene according to the present invention includes bringing a composition containing a compound of the general formula (1): CF3—CH2—CHClX (where X is a fluorine atom or a chlorine atom) into contact with a solid catalyst in the presence of hydrogen chloride. In this production method, the composition containing ozone depleting HCFC such as 3-chloro-1,1,1,3-tetraluoforpropane or 3,3-dichloro-1,1,1-trifluoropropane can be efficiently converted to the 1-chloro-3,3,3-trifluoropropene, which has less influence on the global environment and is useful as a solvent, a cleaning agent, a coolant, a working fluid, a propellant, a raw material for fluorinated resins etc.
    Type: Grant
    Filed: June 27, 2013
    Date of Patent: December 16, 2014
    Assignee: Central Glass Company, Limited
    Inventors: Hideaki Imura, Naoto Takada
  • Patent number: 8895788
    Abstract: The invention relates to a process for manufacturing 1,1,1,2-tetrafluoropropene (1234yf, CF3—CF?CH2) from 1,1,3,3-tetrachlororopropene (1230za, CCl2?CH—CHCl2) and/or 1,1,1,3,3-pentachloropropane (240fa, CCl3CH2CHCl2). The process comprises a step of isomerization of 1,1,3,3-tetrafluoropropene (1230za) to 1,1,2,3-tetrachloropropene (1230xa) followed by conversion of the 1,1,2,3-tetrachloropropene (1230xa) to 1,1,1,2-tetrafluoropropene (1234yf) via a hydrofluorination process.
    Type: Grant
    Filed: January 21, 2014
    Date of Patent: November 25, 2014
    Assignee: Arkema Inc.
    Inventors: Maher Y. Elsheikh, Philippe Bonnet, John A. Wismer
  • Publication number: 20140343331
    Abstract: The invention relates to a process to produce HCFC-244bb from HCFO-1233xf wherein, in one embodiment, co-feed species HFC-245cb is added to the reaction at a pressure of at least about 100 psig; and in another embodiment it is added to maintain a mole ratio of HFC-245cb to HCFO-1233xf of between about 0.005:1 to about 1:1. The HFC-245cb may be added as recycled by-product of the reaction and/or added as fresh feed. The HFC-245cb provides elevated pressures to the reaction thereby facilitating reactor operation, mixing and HCFC-244bb product removal. Other co-feed species are also disclosed.
    Type: Application
    Filed: March 13, 2014
    Publication date: November 20, 2014
    Applicant: HONEWELL INTERNATIONAL, INC.
    Inventors: Haluk Kopkalli, Daniel C. Merkel, Ron Joseph Roof
  • Patent number: 8889925
    Abstract: The present invention provides a process of fluorination in liquid phase in a solvent medium of a compound of formula (II) CX1X2?CZCX3X4X5, in which Z represents H, Cl or F, and each X1 represents independently hydrogen or chlorine, given that at least one of the X1 represents a chlorine.
    Type: Grant
    Filed: March 10, 2010
    Date of Patent: November 18, 2014
    Assignee: Arkema France
    Inventor: Anne Pigamo
  • Patent number: 8877989
    Abstract: A process for dehydrating a hydrofluorocarbon or hydrochlorofluorocarbon, which can be done by simple equipment, and a continuous process of producing 1,3,3,3-tetrafluoropropene using the dehydration process. The dehydration process includes cooling the hydrofluorocarbon or hydrochlorofluorocarbon in gaseous form containing water with a heat exchanger, thereby condensing and liquefying the hydrofluorocarbon or hydrochlorofluorocarbon while freezing and solidifying the water.
    Type: Grant
    Filed: July 22, 2011
    Date of Patent: November 4, 2014
    Assignee: Central Glass Company, Limited
    Inventors: Yoshio Nishiguchi, Yasuo Hibino
  • Publication number: 20140275654
    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-nCHClCH2Cl, 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 29, 2014
    Publication date: September 18, 2014
    Applicant: DAIKIN INDUSTRIES, LTD.
    Inventors: Masatoshi NOSE, Tsuneo YAMASHITA, Atsushi SUZUKI
  • Patent number: 8829254
    Abstract: The present invention describes a process for making CF3CH?CHF (HFO-1234ze). The process involves the addition of carbon tetrachloride (CCl4) to 1,2-dichloroethylene to form CCl3CHClCHCl2. The compound CCl3CHClCHCl2 thus can then either be treated with HF to produce CF3CHClCHClF as the main product, or it can be converted to CCl2?CHCHCl2 (1230za) by dechlorination. CCl2?CHCHCl2 can be treated with HF such that the main product obtained is CF3CHClCHClF. CF3CH?CHCl may be produced as a by-product, but upon treatment with HF, it affords the compound CF3CHClCHClF. The desired compound, CF3CH?CHF (HFO-1234ze), is obtained as a trans/cis mixture by dehydrochlorination of CF3CH2CHClF or by dechlorination of CF3CHClCHClF.
    Type: Grant
    Filed: February 4, 2013
    Date of Patent: September 9, 2014
    Assignee: Honeywell International Inc.
    Inventors: Haridasan K. Nair, Rajiv Ratna Singh, David Nalewajek, Andrew Joseph Poss
  • Patent number: 8822741
    Abstract: A process for the fluorination of haloolefins with elemental fluorine in the presence of anhydrous HF proceeds with high yield and selectivity in the product deriving from the addition of fluorine to the carbon-carbon double bond.
    Type: Grant
    Filed: July 5, 2011
    Date of Patent: September 2, 2014
    Assignee: Solvay Specialty Polymers Italy S.p.A.
    Inventors: Vito Tortelli, Marco Galimberti
  • Patent number: 8816140
    Abstract: The present invention provides a process for producing a fluorine-containing alkene of the general formula CF3(CX2)nCF?CH2, wherein X each independently represents F or Cl, and n is an integer of 0 to 2. The process includes a first reaction step of allowing a specific chlorine-containing compound to react with a fluorinating agent under increased pressure in a gas phase in the presence of at least one fluorination catalyst selected from the group consisting of chromium oxide and fluorinated chromium oxide, and a second reaction step of heating the product of the first reaction step in a gas phase under a pressure lower than the pressure in the first reaction step. The process of the present invention can produce a fluorine-containing alkene with a high selectivity with the use of a catalyst that can be easily handled, while suppressing production of by-products that cannot be easily converted into the target or separated.
    Type: Grant
    Filed: February 8, 2011
    Date of Patent: August 26, 2014
    Assignee: Daikin Industries, Ltd.
    Inventors: Daisuke Karube, Yuzo Komatsu, Atsushi Suzuki
  • Patent number: 8779219
    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: Grant
    Filed: May 12, 2010
    Date of Patent: July 15, 2014
    Assignee: Daikin Industries, Ltd.
    Inventors: Masatoshi Nose, Tsuneo Yamashita, Atsushi Suzuki
  • Patent number: 8680345
    Abstract: Disclosed is a method for the production of 1233xf comprising the continuous low temperature liquid phase reaction of 1,1,1,2,3-pentachloropropane and anhydrous HF, without the use of a catalyst, wherein the reaction takes place in one or more reaction vessels, each one in succession converting a portion of the original reactants fed to the lead reaction vessel and wherein the reactions are run in a continuous fashion.
    Type: Grant
    Filed: December 7, 2011
    Date of Patent: March 25, 2014
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Hsueh Sung Tung, Konstantin A. Pokrovski, Haiyou Wang, Selma Bektesevic
  • Patent number: 8680346
    Abstract: The subject of the invention is a process for the preparation of 2,3-dichloro-1,1,1-trifluoropropane by chlorination of 3,3,3-trifluoropropene at a pressure greater than 2 bar. Application in the synthesis of 1234yf.
    Type: Grant
    Filed: September 11, 2009
    Date of Patent: March 25, 2014
    Assignee: Arkema France
    Inventors: Anne Pigamo, Michel Devic, Laurent Wendlinger
  • Patent number: 8653311
    Abstract: The present invention relates to an azeotropic or azeotrope-like mixture consisting essentially of 1,1,1,2,3,3-hexafluoropropane, hexafluoropropene and hydrogen fluoride.
    Type: Grant
    Filed: April 11, 2013
    Date of Patent: February 18, 2014
    Assignee: Honeywell International Inc.
    Inventors: Ryan Hulse, Hang T. Pham, Rajiv R. Singh, Hsueh S. Tung, Daniel C. Merkel, Konstantin A. Pokrovski
  • Patent number: 8648221
    Abstract: Disclosed is an integrated process to co-produce trans-1-chloro-3,3,3-trifluoro-propene (1233zd(E)), trans-1,3,3,3-tetrafluoropropene (1234ze(E)), and 1,1,1,3,3-pentafluoropropane (245fa). Overall the co-production is a three-step process. The chemistry involves the steps of: (1) the reaction of 240fa with anhydrous HF in excess in a liquid-phase catalyzed reactor in such a way as to co-produce primarily 1233zd(E) and 244fa (plus byproduct HCl); (2) the 244fa stream can then be used to directly produce any of the three desired products; (3a) the 244fa stream can be dehydrochlorinated to produce the desired second product 1234ze(E); and/or (3b) the 244fa stream can be dehydrofluorinated to produce 1233zd(E) if more of that product is desired; and/or (3c) the 244fa stream can be further fluorinated to form 245fa.
    Type: Grant
    Filed: December 9, 2011
    Date of Patent: February 11, 2014
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Haiyou Wang, Konstantin A. Pokrovski, Hsueh Sung Tung, Ian Shankland
  • Patent number: 8618340
    Abstract: Disclosed is a process for the manufacture of HFO-1234yf from TCP in three integrated steps that include hydrofluorination of TCP (tetrachloropropene) to HCFC-1233xf in the vapor phase followed by hydrofluorination of HCFC-1233xf to HCFC-244bb in the liquid phase which is then followed by dehydrochlorination in liquid or vapor phase to produce HFO-1234yf. The vapor phase hydrofluorination is carried out at a higher pressure than the liquid phase hydrofluorination, thereby eliminating the need for compression and/or intermediate recovery. Also, any HCl generated from this reaction is fed to the liquid phase hydrofluorination section to promote agitation and mixing. This results in a more economical process from an initial capital and operating cost versus conducting the 3-steps sequentially.
    Type: Grant
    Filed: November 3, 2009
    Date of Patent: December 31, 2013
    Assignee: Honeywell International Inc.
    Inventors: Haluk Kopkalli, Yuon Chiu, Stephen A. Cottrell, Hsueh Sung Tung, Kevin Uhrich
  • Patent number: 8604257
    Abstract: Disclosed is a process for the preparation of fluorine-containing olefins comprising contacting a chlorofluoroalkane with hydrogen in the presence of a catalyst at a temperature sufficient to cause replacement of the chlorine substituents of the chlorofluoroalkane with hydrogen to produce a fluorine-containing olefin. Also disclosed are catalyst compositions for the hydrodechlorination of chlorofluoroalkanes comprising copper metal deposited on a support, and comprising palladium deposited on calcium fluoride, poisoned with lead and reducing the in the presence or absence of a dehydrochlorination catalyst under conditions effective to form a product stream comprising cis-1,1,1,4,4,4-hexafluoro-2-butene (HFO-1336).
    Type: Grant
    Filed: May 19, 2011
    Date of Patent: December 10, 2013
    Assignee: Honeywell International Inc.
    Inventors: Andrew Joseph Poss, Michael Van Der Puy, Rajiv Ratna Singh, David Nalewajek, Haridasan K. Nair
  • Patent number: 8575407
    Abstract: A support of metal oxyfluoride or metal halide for a metal-based hydrogenation catalyst useful in hydrogenating fluoroolefins is provided.
    Type: Grant
    Filed: March 20, 2012
    Date of Patent: November 5, 2013
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Hsueh Sung Tung
  • 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
  • Patent number: 8530709
    Abstract: The present invention provides a method for the preparation of suitable chlorofluorocarbon and hydrochlorofluorocarbon materials or chlorofluorocarbon and hydrochlorofluorocarbon alkene and alkyne intermediates which serve as useful feedstock for fluorination and reduction to cis-1,1,1,4,4,4-hexafluoro-2-butene. Also presented is a continuous process for the production of cis-1,1,1,4,4,4-hexafluoro-2-butene from the alkene and alkyne intermediates.
    Type: Grant
    Filed: May 19, 2011
    Date of Patent: September 10, 2013
    Assignee: Honeywell International Inc.
    Inventors: Andrew Joseph Poss, David Nalewajek, Michael Van Der Puy, Haridasan K. Nair
  • Patent number: 8519200
    Abstract: Provided are azeotropic or azeotrope-like mixtures of 1,1,3,3-tetrachloro-1-fluoropropane (HCFC-241fa) and hydrogen fluoride. Such compositions are useful as an intermediate in the production of HFC-245fa and HCFO-1233zd.
    Type: Grant
    Filed: February 23, 2012
    Date of Patent: August 27, 2013
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hang T. Pham, Hsueh Sung Tung, Ryan Hulse
  • Patent number: 8481793
    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: Grant
    Filed: July 26, 2012
    Date of Patent: July 9, 2013
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Hsueh S. Tung, Konstantin A. Pokrovski
  • Patent number: 8461401
    Abstract: Hexafluoro-2-butene (HFO-1336) is a low global warming potential blowing agent, refrigerant and solvent. This invention provides a method for making the compound, including the cis-isomer, from the readily available raw materials, carbon tetrachloride and 3,3,3-trifluoropropene. The trans-isomer formed in the process can be isomerized into cis-isomer by the use of an isomerization catalyst.
    Type: Grant
    Filed: March 11, 2011
    Date of Patent: June 11, 2013
    Assignee: Honeywell International Inc.
    Inventors: Hsueh Sung Tung, Haiyou Wang
  • Patent number: 8445736
    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: Grant
    Filed: June 23, 2009
    Date of Patent: May 21, 2013
    Assignee: Arkema Inc.
    Inventors: Maher Y. Elsheikh, Philippe Bonnet
  • Publication number: 20130116483
    Abstract: A process for the fluorination of haloolefins with elemental fluorine in the presence of anhydrous HF proceeds with high yield and selectivity in the product deriving from the addition of fluorine to the carbon-carbon double bond.
    Type: Application
    Filed: July 5, 2011
    Publication date: May 9, 2013
    Applicant: SOLVAY SPECIALTY POLYMERS ITALY S.P.A.
    Inventors: Vito Tortelli, Marco Galimberti
  • Patent number: 8436218
    Abstract: The present invention relates to an azeotropic or azeotrope-like mixture consisting essentially of 1,1,1,2,3,3-hexafluoropropane, hexafluoropropene and hydrogen fluoride.
    Type: Grant
    Filed: May 27, 2010
    Date of Patent: May 7, 2013
    Assignee: Honeywell International Inc.
    Inventors: Ryan Hulse, Hang T. Pham, Rajiv Ratna Singh, Hsueh Sung Tung, Daniel C. Merkel, Konstantin A. Pokrovski
  • Publication number: 20130102814
    Abstract: A process is disclosed for making CF3CH2CHF2, CF3CH?CHF and/or CF3CH?CHCl. The process involves reacting at least one starting material selected from the group consisting of halopropanes of the formula CX3CHClCH2X, halopropenes of the formula CX3CCl?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, CF3CH2CHF2, CF3CH?CHF and CF3CH?CHCl; and recovering the CF3CH2CHF2, CF3CH?CHF and/or CF3CH?CHCl from the product mixture. Also disclosed is a process for making CF3CF2CH3 and/or CF3CF?CH2.
    Type: Application
    Filed: November 29, 2012
    Publication date: April 25, 2013
    Applicant: E I Du Pont De Nemours and Company
    Inventor: E I Du Pont De Nemours and Company
  • Patent number: 8426655
    Abstract: Hexafluoro-2-butene (HFO-1336) is a low global warming potential blowing agent, refrigerant and solvent. This invention provides methods for making the compound, including the cis-isomer, from the readily available raw materials, carbon tetrachloride and ethylene. The trans-isomer formed in the process can be isomerized into cis-isomer by the use of an isomerization catalyst.
    Type: Grant
    Filed: March 11, 2011
    Date of Patent: April 23, 2013
    Assignee: Honeywell International Inc.
    Inventors: Hsueh Sung Tung, Haiyou Wang
  • 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
  • Publication number: 20130023703
    Abstract: A process for the selective dehydrofluorination of hydrochlorofluoroalkanes and novel hydrochlorofluoroalkenes is described wherein an effective amount of a catalytically active metal compound is applied which is selected from the group consisting of AlF3??, MgAlxF2+3x?? and MgZryF2+4y??, wherein x and y have, independently of one another, values in the range of from 0 to 0.33 and ? has a value in the range of from 0 to 0.1. Certain hydrofluorochloroalkenes are also described, as well as their use as intermediates in chemical reactions.
    Type: Application
    Filed: March 31, 2011
    Publication date: January 24, 2013
    Applicant: SOLVAY SA
    Inventors: Johannes Eicher, Ercan Uenveren, Erhard Kemnitz
  • Patent number: 8344191
    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: Grant
    Filed: July 24, 2009
    Date of Patent: January 1, 2013
    Assignee: Daikin Industries, Ltd.
    Inventors: Masatoshi Nose, Daisuke Karube, Akinari Sugiyama, Takashi Shibanuma, Takehiro Chaki
  • Patent number: 8252965
    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: Grant
    Filed: August 12, 2009
    Date of Patent: August 28, 2012
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Hsueh Sung Tung, Konstantin A. Pokrovski
  • Publication number: 20120190901
    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: Application
    Filed: March 19, 2012
    Publication date: July 26, 2012
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: DANIEL C. MERKEL, KONSTANTIN A. POKROVSKI, HSUEH SUNG TUNG
  • 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
  • Patent number: 8207383
    Abstract: The present invention provides a process for preparing 1234yf, comprising: (i) contacting 1233xf 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, unreacted 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: Dominique Deur-Bert, Laurent Wendlinger, Anne Pigamo
  • Patent number: 8153018
    Abstract: Disclosed are compositions and systems having utility in numerous situations, including in particular solvent cleaning systems, as well as refrigerant lubricants and/or compatibilizing agents, and to methods which utilize such compositions and systems. More particularly, the present invention in preferred aspects is directed to solvents, blowing agents, heat transfer fluids and compatibilizing agents comprising the compound 3-chloro-1,1,1,6,6,6-hexafluoro-2,4-hexadiene. In particular, this invention provides a method for the production of the compound of Formula I, 3-chloro-1,1,1,6,6,6- hexafluoro-2,4-hexadiene,comprising reacting 1,1,1,3,3-pentachloropropane with hydrogen fluoride in the presence of a catalyst, in a reactor.
    Type: Grant
    Filed: September 30, 2011
    Date of Patent: April 10, 2012
    Assignee: Honeywell International Inc.
    Inventors: Robert C. Johnson, Hsueh Sung Tung