By Dehalogenation Or Dehydrohalogenation Of Adjacent Carbon Atoms In A Compound Patents (Class 570/155)
  • Patent number: 10611710
    Abstract: The present invention provides a method for efficiently producing 1-chloro-1,2-difluoroethylene at low cost. Specifically, the present invention provides a method for producing 1-chloro-1,2-difluoroethylene, including the step of dehydrohalogenating chlorofluoroethane represented by formula (1) CFClX1—CHFX2 wherein X1 and X2 are different from each other and represent H, F, or Cl; and either X1 or X2 is H.
    Type: Grant
    Filed: July 11, 2017
    Date of Patent: April 7, 2020
    Assignee: DAIKIN INDUSTRIES, LTD.
    Inventors: Daisuke Karube, Satoshi Ohishi
  • Patent number: 10464869
    Abstract: Disclosed are processes for producing halogenated olefins, and preferably tetrafluorinated propene(s), from one or more alkanes having both fluorine substituents and non-fluorine substituents, preferably with a high degree of conversion and selectivity. Preferably the process comprises the use of a catalyzed reaction in which the catalyst is selected from the group consisting of activated carbons halogenated mono- and di-valent metal oxides, mono- and di-valent Lewis acid metal halides, zero-valent metals, and combinations of these.
    Type: Grant
    Filed: May 26, 2017
    Date of Patent: November 5, 2019
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Hsueh Sung Tung, Sudip Mukhopadhyay
  • Patent number: 10266465
    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-pentafluoropropane, 1,1,1,3,3-pentafluoropropene, 1,1,1,2,3-pentafluoropropene and 2-chloro, 1,1,1,2-tetrafluoropropane.
    Type: Grant
    Filed: July 6, 2018
    Date of Patent: April 23, 2019
    Assignee: ARKEMA FRANCE
    Inventors: Philippe Bonnet, Bertrand Collier, Dominque Deur-Bert, Laurent Wendlinger
  • Patent number: 10160703
    Abstract: The invention provides an improved process to manufacture 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) by reacting 2-chloro-3,3,3,-trifluoropropene (HCFO-1233xf) with hydrogen fluoride, in a liquid phase reaction in the presence of hydrogen chloride and a liquid phase fluorination catalyst. The hydrogen chloride is added into the reaction from an external source at a pressure of about 100 psig or more. The HCFC-244bb is an intermediate in the production of 2,3,3,3-tetrafluoropropene-1 (HFO-1234yf).
    Type: Grant
    Filed: November 9, 2015
    Date of Patent: December 25, 2018
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Daniel C. Merkel, Stephen A. Cottrell, Robert C. Johnson
  • Patent number: 10112879
    Abstract: The invention provides an improved process to manufacture 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) by reacting 2-chloro-3,3,3,-trifluoropropene (HCFO-1233x1) with hydrogen fluoride, in a liquid phase reaction in the presence of hydrogen chloride and a liquid phase fluorination catalyst. The hydrogen chloride is added into the reaction from an external source at a pressure of about 100 psig or more. The HCFC-244bb is an intermediate in the production of 2,3,3,3-tetrafluoropropene-1 (HFO-1234yf).
    Type: Grant
    Filed: February 21, 2017
    Date of Patent: October 30, 2018
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Daniel C. Merkel, Stephen A. Cottrell, Robert C. Johnson
  • Patent number: 10093601
    Abstract: Compounds with fire extinguishing properties having the formula: wherein R1 is —CR5R6R7 or —CR5R6CR8R9R10 as well as fire extinguishing units including one or more of the compounds.
    Type: Grant
    Filed: June 29, 2015
    Date of Patent: October 9, 2018
    Assignee: The Boeing Company
    Inventors: Kimberly-Alice D. Gregersen, James Craig Moreland, Ekaterina A. Badaeva, Andrew M. Zweig
  • Patent number: 10087127
    Abstract: The present invention relates, in part, to the discovery that the presence of HF in a HCFC-244bb feedstream in a reaction for the preparation of HFO-1234yf results in selectivity changeover from HFO-1234yf to HCFO-1233xf. By substantially removing HF, it is shown that the selectivity to HFO-1234yf via dehydrochlorination of HCFC-244bb is improved.
    Type: Grant
    Filed: November 14, 2016
    Date of Patent: October 2, 2018
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Haiyou Wang, Hsueh Sung Tung
  • Patent number: 10059647
    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 (which may be purchased or synthesized from 1,2,3-trichloropropane) is fluorinated (preferably with HF in gas-phase in the presence of a catalyst) to synthesize a compound such as CF3CCl?CH2, preferably in a 80-96% selectivity. The CF3CCl?CH2 is preferably converted to CF3CFClCH3 (244-isomer) using a SbCl5 as the catalyst which is then transformed selectively to 1234yf, preferably in a gas-phase catalytic reaction using activated carbon as the catalyst. 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.
    Type: Grant
    Filed: May 5, 2014
    Date of Patent: August 28, 2018
    Assignee: 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
  • Patent number: 10059648
    Abstract: Provided is an efficient method for producing a fluorine-containing compound without the need for a rectification column involving numerous stages, extractive distillation, etc. The method for producing a fluorine-containing compound includes the step of supplying a composition containing a mixture to a dehydrohalogenation step, the mixture being at least one member selected from the group consisting of mixtures of at least one fluoroolefin and at least one hydrofluorocarbon, the boiling points of which are close to each other, azeotropic mixtures of at least one fluoroolefin and at least one hydrofluorocarbon, and pseudo-azeotropic compounds of at least one fluoroolefin and at least one hydrofluorocarbon.
    Type: Grant
    Filed: May 18, 2016
    Date of Patent: August 28, 2018
    Assignee: DAIKIN INDUSTRIES, LTD.
    Inventor: Shun Ohkubo
  • Patent number: 10047326
    Abstract: An azeotropic-like composition containing 2-chloro-1,3,3,3-tetrafluoropropene and 1-chloro-3,3,3-trifluoropropene is provided. The azeotropic-like composition according to the present invention is non-flammable, has little influence on the environment, and has substantially the same composition ratio in the liquid phase and the gas phase. By use of an azeotropic-like composition according to the present invention, a washing detergent, a solvent, a silicone solvent, a foaming agent, a coolant, a heating medium for a heat pump, and a high temperature working fluid that are non-flammable, have little influence on the environment, and have substantially the same composition ratio in a liquid phase and a gas phase thereof may be provided.
    Type: Grant
    Filed: March 31, 2017
    Date of Patent: August 14, 2018
    Assignee: CENTRAL GLASS COMPANY, LIMITED
    Inventors: Masahiko Tani, Hideaki Imura, Yoshio Nishiguchi, Naoto Takada
  • Patent number: 9790149
    Abstract: A process for preparing 2,3,3,3-tetrafluoropropene (CF3CF?CH2). 3,3,3-trifluoro-2-chloropropene (CF3CCl?CH2) is fluorinated with HF in the vapour phase in the presence of a chromia-containing catalyst to produce an intermediate composition 1,1,1,2,2-pentafluoropropane (CF3CF2CH3), which is dehydrofluorinated to produce CF3CF?CH2.
    Type: Grant
    Filed: January 4, 2017
    Date of Patent: October 17, 2017
    Assignee: MEXICHEM AMANCO HOLDING S.A. DE C.V.
    Inventors: Andrew P Sharratt, Leslie R Seddon
  • Patent number: 9783471
    Abstract: The present invention concerns a method of producing at least one compound of formula (II): CF3—CX(Z)n-CHX(Z)n in which X represents, independently, a hydrogen, fluorine or chlorine atom, Z represents, independently, a hydrogen or fluorine atom, and n=0 or 1, from at least one compound of formula (I): CX(Y)2-CX(Y)m-CHmXY in which X and Y represent, independently, a hydrogen, fluorine or chlorine atom and m=0 or 1. The method comprises at least one step during which at least one compound of formula (I) reacts with HF in the gaseous phase in the presence of a fluorination catalyst in order to give at least one compound of formula (II), characterized in that the catalyst is made from chromium oxyfluoride containing at least nickel as the co-metal and at least one rare earth metal.
    Type: Grant
    Filed: September 17, 2014
    Date of Patent: October 10, 2017
    Assignee: Arkema France
    Inventor: Laurent Wendlinger
  • Patent number: 9758450
    Abstract: The invention relates to a separation process whereby 2-chloro-3,3,3-trifluoropropene (1233xf) is separated from a mixture containing other fluorinated organics and high boiling materials such as dimers using azeotropes of HF formed by adding appropriate amounts to the mixture which facilitate separation by, e.g. distillation.
    Type: Grant
    Filed: April 8, 2016
    Date of Patent: September 12, 2017
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Haiyou Wang, Selma Bektesevic, Daniel C. Merkel, Hsueh Sung Tung, Konstantin A. Pokrovski
  • Patent number: 9663424
    Abstract: Disclosed are processes for producing halogenated olefins, and preferably tetrafluorinated propene(s), from one or more alkanes having both fluorine substituents and non-fluorine substituents, preferably with a high degree of conversion and selectivity. Preferably the process comprises the use of a catalyzed reaction in which the catalyst is selected from the group consisting of activated carbons, halogentated mono- and di-valent metal oxides, mono- and di-valent Lewis acid metal halides, zero-valent metals, and combinations of these.
    Type: Grant
    Filed: August 16, 2013
    Date of Patent: May 30, 2017
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Haiyou Wang, Hsueh Sung Tung, Sudip Mukhopadhyay
  • Patent number: 9586876
    Abstract: The present invention discloses a manufacturing process to produce high purity 1234yf from 245eb, which preferably includes the removal of impurities present in 245eb raw material, the dehydrofluorination of 245eb, and the removal of impurities present in final crude product. The disclosed manufacturing process allows the production of a 1234yf product with lower the levels of 1225ye and/or trifluoropropene, preferably in amounts of less than about 500, and 50 ppm, respectively.
    Type: Grant
    Filed: June 30, 2014
    Date of Patent: March 7, 2017
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Haiyou Wang, Hsueh Sung Tung, Rajiv R. Singh, Ian Shankland
  • Patent number: 9573867
    Abstract: The present invention relates to an improved method for manufacturing 2-chloro-3,3,3-trifluoropropene, (HCFC-1233xf) by reacting 1,1,2,3-tetrachloropropene, 1,1,1,2,3-pentachloropropane, and/or 2,3,3,3-tetrachloropropene with hydrogen fluoride, in a vapor phase reaction vessel in the presence of a vapor phase fluorination catalyst and stabilizer. HCFC-1233xf is an intermediate in the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf) which is a refrigerant with low global warming potential.
    Type: Grant
    Filed: January 4, 2016
    Date of Patent: February 21, 2017
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Daniel C. Merkel, Hsueh S. Tung
  • Patent number: 9540295
    Abstract: The present invention relates, in part, to the discovery that high temperatures during the fluorination of 1,1,2,3-tetrachloropropene (HCO-1230xa) to 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) results in catalyst instability, reduced selectivity of the conversion, and/or the formation of one or more undesirable by-products. By controlling the reaction temperature, it is shown that the catalyst life may be extended and the selectivity of the reaction improved. Such control similarly results in an overall improvement in the production of certain hydrofluoroolefins, particularly 2,3,3,3-tetrafluoropropene (HFO-1234yf).
    Type: Grant
    Filed: September 29, 2012
    Date of Patent: January 10, 2017
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Selma Bektesevic, Hsueh Sung Tung, Haiyou Wang
  • Patent number: 9440896
    Abstract: Disclosed is a process for producing hexafluoro-2-butyne comprising, reacting HCFC-336 with an aqueous solution of an alkali metal hydroxide in the presence of a quaternary alkylammonium salt which comprises at least one alkyl group of at least 8 carbons, and recovering the hexafluoro-2-butyne, wherein the conversion of dichloro-1,1,1,4,4,4-hexafluorobutane is at least 50% per hour. Also disclosed is a process for producing hexafluoro-2-butyne comprising, reacting HCFC-336 with an aqueous solution of an alkali metal hydroxide in the presence of a quaternary alkylammonium salt having alkyl groups of from four to ten carbon atoms, and mixtures thereof, and a non-ionic surfactant, and recovering the hexafluoro-2-butyne, and wherein the conversion of dichloro-1,1,1,4,4,4-hexafluorobutane to hexafluoro-2-butyne is at least 20% per hour.
    Type: Grant
    Filed: September 27, 2013
    Date of Patent: September 13, 2016
    Assignee: THE CHEMOURS COMPANY FC, LLC
    Inventors: Sheng Peng, Mario Joseph Nappa
  • Patent number: 9416074
    Abstract: The present invention relates, in part, to the discovery that the presence of impurities in a reactor for dehydrochlorinating HCFC-244bb to HFO-1234yf results in a reduced conversion rate and/or a selectivity changeover from HFO-1234yf to HCFO-1233xf. By substantially removing such impurities, it is shown that the conversion rate may be improved and selectivity to HFO-1234yf via dehydrochlorination of HCFC-244bb is also improved.
    Type: Grant
    Filed: October 10, 2012
    Date of Patent: August 16, 2016
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Haiyou Wang, Hsueh Sung Tung, Daniel C. Merkel
  • Patent number: 9353030
    Abstract: Disclosed is a one step process for making of 1,1,1,4,4,4-hexafluoro-2-butene. More specifically, the present invention provides a process for making hexafluoro-2-butene, continuously, from 2-chloro-3,3,3-trifluoropronene using Fe2O3/NiO impregnated carbon catalyst at 600° to 650° C.
    Type: Grant
    Filed: June 12, 2015
    Date of Patent: May 31, 2016
    Assignee: Honeywell International Inc.
    Inventors: Haridasan K. Nair, David Nalewajek, Glenn Matthies
  • Patent number: 9334208
    Abstract: The present invention provides a process for preparing 2,3,3,3-tetrafluoropropene from 1,1,1,2,3-pentachloropropane and/or 1,1,2,2,3-pentachloropropane, comprising the following steps: (a) catalytic reaction of 1,1,1,2,3-pentachloropropane and/or 1,1,2,2,3-pentachloropropane with HF into a reaction mixture comprising HCl, 2-chloro-3,3,3-trifluoropropene, 2,3,3,3-tetrafluoropropene, unreacted HF, and optionally 1,1,1,2,2-pentafluoropropane; (b) separating the reaction mixture into a first stream comprising HCl and 2,3,3,3-tetrafluoropropene and a second stream comprising HF, 2-chloro-3,3,3-trifluoropropene and optionally 1,1,1,2,2-pentafluoropropane; (c) catalytic reaction of the second stream into a reaction mixture comprising 2,3,3,3-tetrafluoropropene, HCl, unreacted 2-chloro-3,3,3-trifluoropropene, unreacted HF and optionally 1,1,1,2,2-pentafluoropropane and (d) feeding the reaction mixture of step (c) directly without separation to step (a).
    Type: Grant
    Filed: December 14, 2011
    Date of Patent: May 10, 2016
    Assignee: Arkema France
    Inventors: Dominique Deur-Bert, Bertrand Collier, Laurent Wendlinger
  • Patent number: 9302962
    Abstract: A method of producing a fluoropropane of formula CF3CH?CHF, comprising contacting a mixture of 1,1,1,3,3-pentafluoropropane and Z-1,3,3,3-tetrafluoropropene in the gas phase with a catalyst comprising at least one catalyst selected from the group consisting of fluorinated Cr2O3 or Cr/Ni on fluoride alumina, in the presence of an oxygen containing gas, to form a mixture comprising Z-1,3,3,3-tetrafluoropropane, E-1,3,3,3,-tetrafluoropropene, hydrogen fluoride, and optionally unreacted 1,1,1,3,3-pentafluoropropane, separating the E-1,3,3,3-tetrafluoropropene from the Z-isomer and any unreacted 1,1,1,3,3-pentafluoropropane, if present, and recovering said E-1,3,3,3-tetrafluoropropene.
    Type: Grant
    Filed: August 6, 2015
    Date of Patent: April 5, 2016
    Assignee: THE CHEMOURS COMPANY FC, LLC
    Inventors: Sheng Peng, Mario Joseph Nappa
  • Patent number: 9296669
    Abstract: Disclosed is a process for passivating a surface of a dehydrochlorination reactor comprising: stopping a flow of hydrochlorofluoropropane to a reactor, passing a gas mixture comprising hydrogen gas through the reactor at a temperature of at least 25° C. for a period of time sufficient to restore the selectivity of a dehydrochlorination reaction, stopping the flow of the hydrogen gas mixture, and resuming the flow of hydrochlorofluoropropane to the dehydrochlorination reaction.
    Type: Grant
    Filed: January 8, 2013
    Date of Patent: March 29, 2016
    Assignee: E.I. DU PONT DE NEMOURS AND COMPANY
    Inventors: Xuehui Sun, Mario Joseph Nappa, Haiyou Wang, Haluk Kopkalli
  • Patent number: 9227893
    Abstract: The present invention relates to an improved method for manufacturing 2-chloro-3,3,3,-trifluoropropene (HCFC-1233xf) by reacting 1,1,2,3-tetrachloropropene, 1,1,1,2,3-pentachloropropane, and/or 2,3,3,3-tetrachloropropene with hydrogen fluoride, in a vapor phase reaction vessel in the presence of a vapor phase fluorination catalyst and stabilizer. HCFC-1233xf is an intermediate in the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf) which is a refrigerant with low global warming potential.
    Type: Grant
    Filed: December 15, 2014
    Date of Patent: January 5, 2016
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Daniel C. Merkel, Hsueh S. Tung
  • Patent number: 9174896
    Abstract: A vapor phase process is disclosed for making internal fluorobutenes. The process involves contacting a halobutane starting material selected from the group consisting of CF2HCHClCH2CCl2H, CF2HCHClCH2CCl3, CF3CHClCH2CCl2H, CF3CHClCH2CCl3, CF3CHClCHClCCl2H, CF3CHClCHClCCl3, CF3CCl2CH2CCl2H, CF3CCl2CH2CCl3, CF3CCl2CHClCCl2H, CF3CCl2CHClCCl3, CF3CClFCHClCCl2H, CF3CClFCHClCCl3, CF3CClFCH2CCl2H, CF3CClFCH2CCl3, CF3CClFCHFCCl2H, CF3CClFCHFCCl3, CF3CClHCHFCCl2H and CF3CClHCHFCCl3, with HF in a reaction zone in the presence of a chromium oxyfluoride catalyst to produce a product mixture comprising an internal fluorobutene. Another vapor phase process is disclosed for making internal fluoropentenes.
    Type: Grant
    Filed: November 7, 2011
    Date of Patent: November 3, 2015
    Assignee: THE CHEMOURS COMPANY FC, LLC
    Inventors: Mario Joseph Nappa, Ekaterina N Swearingen
  • Patent number: 9162945
    Abstract: Provided is a process for preparing 2-chloro-3,3,3-trifluoropropene, wherein at least one chlorine-containing compound selected from the group consisting of chloropropane represented by formula (1): CX3CHClCH2Cl, 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, is used as a starting compound, and said at least one chlorine-containing compound is reacted with hydrogen fluoride while being heated in a gaseous state in the presence of 50 ppm or more of water relative to the chlorine-containing compound. The process of the present invention makes it possible to produce 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) in a manner that is easily conducted, economically advantageous, and suitable for industrial scale production.
    Type: Grant
    Filed: March 21, 2013
    Date of Patent: October 20, 2015
    Assignee: DAIKIN INDUSTRIES, LTD.
    Inventors: Masayuki Kishimoto, Yuzo Komatsu
  • Patent number: 9102580
    Abstract: The present disclosure provides a fluorination process which involves reacting a hydrohaloalkene of the formula RfC—Cl?CH2 with HF in a reaction zone in the presence of a fluorination catalyst selected from the group consisting of TaF5 and TiF4 to produce a product mixture containing a hydrohaloalkane of the formula RfCFClCH3, wherein Rf is a perfluorinated alkyl group.
    Type: Grant
    Filed: November 9, 2012
    Date of Patent: August 11, 2015
    Assignee: THE CHEMOURS COMPANY FC, LLC
    Inventors: Mario Joseph Nappa, Andrew Jackson, Daniel C. Merkel
  • Patent number: 9067856
    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: Grant
    Filed: August 12, 2014
    Date of Patent: June 30, 2015
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Robert C. Johnson, Hsueh S. Tung, Daniel C. Merkel
  • Patent number: 9061957
    Abstract: Disclosed is a method for producing fluorinated organic compounds, including reacting CF2?CFCl with CH2FCl under conditions effective to produce a product composition including CF3CClFCH2Cl. The present invention also relates to the production of hydrofluoropropenes, which preferably comprises converting at least one compound of formula (I): CF3CFnCHmXa?m??(I) to at least one compound of formula (II) CF3CZCHZ??(II). where each X is independently Cl, F, I or Br; each Z is independently H or F; n is 1 or 2; m is 1, 2 or 3, provided that when n is 1, m is 1 or 2; a is 2 or 3, and a?m?0. Certain embodiments include the step of reacting fluorinated C2 olefin, such as tetrafluoroethylene, with a C1 addition agent under conditions effective to produce a compound of formula (I).
    Type: Grant
    Filed: January 22, 2013
    Date of Patent: June 23, 2015
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Sudip Mukhopadhyay, Haridasan K. Nair, Rajesh K. Dubey, Rajiv R. Singh, George A. Shia
  • Patent number: 9056808
    Abstract: Processes for the production of chlorinated propenes are provided. The present processes make use of 1,2-dichloropropane, a by-product in the production of chlorohydrin, as a low cost starting material, alone or in combination with 1,2,3-trichloropropane. The present processes can also generate anhydrous HCl as a byproduct that can be removed from the process and used as a feedstock for other processes, providing further time and cost savings. Finally, the processes are advantageously conducted in the liquid phase, thereby presenting additional savings as compared to conventional, gas phase processes.
    Type: Grant
    Filed: May 18, 2012
    Date of Patent: June 16, 2015
    Assignee: Dow Global Technologies, LLC
    Inventors: Max M. Tirtowidjojo, William J. Kruper, Jr., Barry B. Fish, David S. Laitar
  • Publication number: 20150148570
    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: Application
    Filed: January 30, 2015
    Publication date: May 28, 2015
    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: 9035112
    Abstract: Disclosed is a process for producing 2-chloro-1,3,3,3-tetrafluoropropene (1224), including a first step of separating 2,3-dichloro-1,1,1,3-tetrafluoropropane (234da) into erythro form and threo form, and a second step of bringing the separated erythro form or threo form in contact with a base to obtain 2-chloro-1,3,3,3-tetrafluoropropene (1224). The first step is a step of separating 234da by distillation to achieve a separation into a fraction containing mainly erythro form and a fraction containing mainly threo form. In the second step, 1224 cis form is obtained from the erythro form, and 1224 trans form is obtained from the threo form. By this process, it is possible to selectively and efficiently produce cis form or trans form of 2-chloro-1,3,3,3-tetrafluoropropene (1224).
    Type: Grant
    Filed: May 8, 2014
    Date of Patent: May 19, 2015
    Assignee: Central Glass Company, Ltd.
    Inventors: Hideaki Imura, Yoshio Nishiguchi, Masamune Okamoto, Tatsuya Hayasaka, Minako Oomura, Satoru Okamoto, Naoto Takada
  • Patent number: 9029616
    Abstract: The present invention provides routes for making 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd) from commercially available raw materials. More specifically, this invention provides routes for HCFO-1233zd from inexpensive and commercially available trifluoromethane (HFC-23).
    Type: Grant
    Filed: July 14, 2014
    Date of Patent: May 12, 2015
    Assignee: Honeywell International Inc.
    Inventors: Haridasan K. Nair, Andrew Joseph Poss, David Nalewajek, Yian Zhai
  • Patent number: 9018429
    Abstract: The subject of the invention is a process for the preparation of fluoroolefin compounds.
    Type: Grant
    Filed: January 12, 2010
    Date of Patent: April 28, 2015
    Assignee: Arkenna France
    Inventors: Pierre-Marie Sedat, Jean-Michel Bossoutrot
  • Patent number: 9018428
    Abstract: Disclosed is a reactor and agitator useful in a high pressure process for making 1-chloro-3,3,3-trifluoropropene (1233zd) from the reaction of 1,1,1,3,3-pentachloropropane (240fa) and HF, wherein the agitator includes one or more of the following design improvements: (a) double mechanical seals with an inert barrier fluid or a single seal; (b) ceramics on the rotating faces of the seal; (c) ceramics on the static faces of seal; (d) wetted o-rings constructed of spring-energized Teflon and PTFE wedge or dynamic o-ring designs; and (e) wetted metal surfaces of the agitator constructed of a corrosion resistant alloy.
    Type: Grant
    Filed: March 14, 2013
    Date of Patent: April 28, 2015
    Assignee: Honeywell International Inc.
    Inventor: Stephen A. Cottrell
  • Patent number: 9012702
    Abstract: A dehydrochlorination process is disclosed. The process involves contacting RfCFClCH2X with a catalyst in a reaction zone to produce a product mixture comprising RfCF?CHX, wherein said catalyst comprises MY supported on carbon, and wherein Rf is a perfluorinated alkyl group, X ?H, F, Cl, Br or I, M=K, Na or Cs, and Y?F, Cl or Br.
    Type: Grant
    Filed: February 10, 2012
    Date of Patent: April 21, 2015
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Xuehui Sun, Mario Joseph Nappa
  • 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: 8987536
    Abstract: The present disclosure relates to processes for reducing the concentration of RfC?CX impurities in fluoroolefins. The process involves: contacting a mixture comprising at least one fluoroolefin and at least one RfC?CX impurity with at least one amine to reduce the concentration of the at least one RfC?CX impurity in the mixture; wherein Rf is a perfluorinated alkyl group, and X is H, F, Cl, Br or I. The present disclosure also relates to processes for making at least one hydrotetrafluoropropene product selected from the group consisting of CF3CF?CH2, CF3CH?CHF, and mixtures thereof and reducing the concentration of CF3C?CH impurity generated during the process. The present disclosure also relates to processes for making at least one hydrochlorotrifluoropropene product selected from the group consisting of CF3CCl?CH2, CF3CH?CHCl, and mixtures thereof and reducing the concentration of CF3C?CH impurity generated during the process.
    Type: Grant
    Filed: June 6, 2013
    Date of Patent: March 24, 2015
    Assignee: E I du Pont de Nemours and Company
    Inventors: Xuehui Sun, Mario Joseph Nappa
  • Publication number: 20150080618
    Abstract: A production method of cis-1,3,3,3-tetrafluoropropene according to the present invention includes the steps of: subjecting 1,1,1,3,3-pentafluoropropane to dehydrofluorination to form a reaction mixture (A) containing cis-1,3,3,3-tetrafluoropropene, trans-1,3,3,3-tetrafluoropropene and unreacted 1,1,1,3,3-pentafluoropropane; distilling the reaction mixture (A) to separate the trans-1,3,3,3-tetrafluoropropene from the reaction mixture (A) and collect a reaction mixture (B) containing the cis-1,3,3,3-tetrafluoropropene and the 1,1,1,3,3-pentafluoropropane; and reacting the reaction mixture (B) with a base and thereby obtaining the cis-1,3,3,3-tetrafluoropropene from the reaction mixture (B). This production method enables efficient production of high-purity cis-1,3,3,3-tetrafluoropropene and thus has industrial advantages.
    Type: Application
    Filed: April 2, 2013
    Publication date: March 19, 2015
    Inventors: Satoshi Yoshikawa, Satoru Okamoto, Yoshio Nishiguchi, Fuyuhiko Sakyu
  • Patent number: 8975454
    Abstract: The instant invention relates to a process and method for manufacturing 2,3,3,3-tetrafluoropropene by dehydrohalogenating a reactant stream of 2-chloro-1,1,1,2-tetrafluoropropane that is substantially free from impurities, particularly halogenated propanes, propenes, and propynes.
    Type: Grant
    Filed: October 25, 2011
    Date of Patent: March 10, 2015
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh S. Tung, Haiyou Wang
  • Publication number: 20150057471
    Abstract: The use of sulfuryl chloride, either alone or in combination with chlorine, as a chlorinating agent is disclosed.
    Type: Application
    Filed: May 18, 2012
    Publication date: February 26, 2015
    Applicant: DOW GLOBAL TECHNOLOGIES LLC
    Inventors: Max M Tirtowidjojo, Matthew Lee Grandbois, John D. Myers, William J. Kruper, JR.
  • Publication number: 20150045588
    Abstract: The present invention provides routes for making 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd) from commercially available raw materials. More specifically, this invention provides routes for HCFO-1233zd from inexpensive and commercially available trifluoromethane (HFC-23).
    Type: Application
    Filed: July 14, 2014
    Publication date: February 12, 2015
    Inventors: Haridasan K. Nair, Andrew Joseph Poss, David Nalewajek, Yian Zhai
  • Publication number: 20150038749
    Abstract: Disclosed is a process for producing 2-chloro-1,3,3,3-tetrafluoropropene (1224), including a first step of separating 2,3-dichloro-1,1,1,3-tetrafluoropropane 234da) into erythro form and threo form, and a second step of bringing the separated erythro form or threo form in contact with a base to obtain 2-chloro-1,3,3,3-tetrafluoropropene (1224). The first step is a step of separating 234da by distillation to achieve a separation into a fraction containing mainly erythro form and a fraction containing mainly threo form. In the second step, 1224 cis form is obtained from the erythro form, and 1224 trans form is obtained from the threo form. By this process, it is possible to selectively and efficiently produce cis form or trans form of 2-chloro-1,3,3,3-tetrafluoropropene (1224).
    Type: Application
    Filed: May 8, 2014
    Publication date: February 5, 2015
    Applicant: Central Glass Company, Limited
    Inventors: Hideaki IMURA, Yoshio NISHIGUCHI, Masamune OKAMOTO, Tatsuya HAYASAKA, Minako OOMURA, Satoru OKAMOTO, Naoto TAKADA
  • Patent number: 8940948
    Abstract: Provided are methods for producing fluorinated organic compounds, which preferably comprises converting at least one compound of formula (I) CH2XCHZCF3 to at least one compound of formula (II) CHX?CZCF3 where X and Z are independently H or F, with the proviso that X and Z are not the same. The converting step comprises catalytically reacting at least one compound of formula (I), preferably via dehydrogenation or oxidative dehydrogenation. In another aspect, the inventive method of preparing fluorinated organic compounds comprises converting a reaction stream comprising at least one pentafluoropropene to a product stream comprising at least one pentafluoropropane and at least one compound of formula (I), separating out the compound of formula (I) from the product stream, and converting the compound of formula (I) separated from the product stream to at least one compound of formula (II), wherein the conversion the compound of formula (I) to 3,3,3-trifluoropropyne is substantially limited.
    Type: Grant
    Filed: July 17, 2013
    Date of Patent: January 27, 2015
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Hsueh Sung Tung
  • Patent number: 8936757
    Abstract: Apparatuses and processes are provided for stripping gaseous hydrocarbons from particulate material. One process comprises the step of contacting particles containing hydrocarbons with a stripping vapor in countercurrent flow to remove at least a portion of the hydrocarbons with the stripping vapor to form stripped particles. Contacting the particles includes advancing the particles down a sloping element of a structured packing toward a reinforcing rod that is disposed along a lower channel portion of the sloping element. The particles are advanced over the reinforcing rod. The particles are contacted with the stripping vapor that is rising up adjacent to the lower channel portion.
    Type: Grant
    Filed: December 28, 2011
    Date of Patent: January 20, 2015
    Assignee: UOP LLC
    Inventors: Erick D. Gamas-Castellanos, Mitchell John Kowalczyk
  • Publication number: 20150011805
    Abstract: The present invention provides a process for purifying a (E)-1-chloro-3,3,3-trifluoropropene composition (OF-1233E composition) in which at hydrogen fluoride and 2-chloro-1,1,1,3,3-pentafluoropropane are contained by bringing the (E)-1-chloro-3,3,3-trifluoropropene composition into contact with a weak base and a method for producing (E)-1-chloro-3,3,3-trifluoropropene composition by distilling the (E)-1-chloro-3,3,3-trifluoropropene composition obtained by such a purification process. This makes it possible to efficiently produce OF-1233E by removing the hydrogen fluoride from the OF-1233E composition, without generating any new component difficult to separate by distillation, and subjecting the resulting composition to distillation.
    Type: Application
    Filed: October 3, 2012
    Publication date: January 8, 2015
    Inventors: Masamune Okamoto, Hideaki Imura, Naoto Takada, Tatsuya Hayasaka
  • Patent number: 8921622
    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: Grant
    Filed: March 31, 2011
    Date of Patent: December 30, 2014
    Assignee: Solvay SA
    Inventors: Johannes Eicher, Ercan Uenveren, Erhard Kemnitz
  • 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