Metal Halide Containing Catalyst Patents (Class 570/166)
  • Patent number: 11999673
    Abstract: A method for conversion of a composition containing HCFO-1233zd(Z) and HCFC-244fa to form HCFO-1233zd(E) by reacting a mixture including HCFO-1233zd(Z) and HCFC-244fa in a vapor phase in the presence of a catalyst to simultaneously isomerize HCFC-1233zd(Z) to form HCFO-1233zd(E) and dehydrohalogenate HCFC-244fa to form HCFO-1233zd(E). The catalyst may be a chromium-based catalyst such as chromium trifluoride, chromium oxyfluoride, or chromium oxide, for example.
    Type: Grant
    Filed: August 28, 2022
    Date of Patent: June 4, 2024
    Assignee: Honeywell International Inc.
    Inventors: Christian Jungong, Daniel C. Merkel
  • Patent number: 11912639
    Abstract: Processes for producing Z-1,1,1,4,4,4-hexafluorobut-2-ene and intermediates for producing same. A process for producing 2-chloro-1,1,1,4,4,4-hexafluorobutane comprises contacting 1,1,2,4,4-pentachlorobuta-1,3-diene with HF in the liquid phase in the presence of a fluorination catalyst. A process for producing 2,2-dichloro-1,1,1,4,4,4-hexafluorobutane comprises contacting 2-chloro-1,1,1,4,4,4-hexafluorobutane with a chlorine source. A process for producing 1,1,1,4,4,4-hexafluoro-2-butyne comprises contacting 2,2-dichloro-1,1,1,4,4,4-hexafluorobutane with a base. A process for producing Z-1,1,1,4,4,4-hexafluorobut-2-ene comprises contacting 1,1,1,4,4,4-hexafluoro-2-butyne with hydrogen.
    Type: Grant
    Filed: April 3, 2020
    Date of Patent: February 27, 2024
    Assignee: THE CHEMOURS COMPANY FC, LLC
    Inventors: Sheng Peng, Allen Capron Sievert
  • Patent number: 11760707
    Abstract: The present invention pertains to a novel process of manufacturing the compound 2,3,3,3-tetrafluoropropene (1234yf). The compound 1234yf is the newest refrigerant with zero OPD (Ozone Depleting Potential) and zero GWP (Global Warming Potential). Thus, the invention relates to a process, involving a carbene generation route, for the manufacture of the compound 2,3,3,3-tetrafluoropropene (1234yf), of the compound 243db (2,3-dichloro-1,1,1-trifluoropropane), and optionally of the compound 2-chloro-1,1,1-trifluoropropene (1233xf) via carbene route and compound 243db (2,3-dichloro-1,1,1-trifluoropropane). The invention also relates to a process for the manufacture of the compound 2,3,3,3-tetrafluoropropene (1234yf), wherein the compound 243db (2,3-dichloro-1,1,1-trifluoropropane) serves as a starting material, for the manufacture of the compound 2,3,3,3-tetrafluoropropene (1234yf).
    Type: Grant
    Filed: November 12, 2020
    Date of Patent: September 19, 2023
    Inventors: Changyue Zhou, Yong Wang
  • Patent number: 11565987
    Abstract: A method of making chlorofluorohydrocarbons including, contacting, a fluorinated hydrocarbon reagent in the vapor phase, with hydrogen chloride (HCl). The reaction is conducted in the presence of an effective amount of a catalyst, at an elevated temperature sufficient to effect hydrochlorination to form a reaction mixture including a chlorofluorohydrocarbon.
    Type: Grant
    Filed: August 12, 2019
    Date of Patent: January 31, 2023
    Assignee: THE CHEMOURS COMPANY FC, LLC
    Inventor: Xuehui Sun
  • Patent number: 11542231
    Abstract: The present invention aims to provide a method by which fluorine-containing sulfide compounds, particularly sulfide compounds that contain hydrogen and fluorine, can be produced in a simple, low-cost and industrial manner. Provided is a method of producing a fluorine-containing sulfide compound represented by the following formula (2): (F)n-A3-S-A4-(F)m??(2) (wherein A3 and A4 are independently an optionally substituted hydrocarbyl group with a carbon number of 1 to 3; n and m represent the numbers of fluorine atoms binding to A3 and A4, with n+m=1 to 13 being satisfied), comprising reacting a chlorine-containing sulfide compound represented by the following formula (1): (Cl)n-A1-S-A2-(Cl)m??(1) (wherein A1 and A2 are independently an optionally substituted hydrocarbyl group with a carbon number of 1 to 3; n and m represent the numbers of chlorine atoms binding to A1 and A2, with n+m=1 to 13 being satisfied) and a fluorinating agent.
    Type: Grant
    Filed: March 29, 2019
    Date of Patent: January 3, 2023
    Assignee: KANTO DENKA KOGYO CO., LTD.
    Inventors: Wataru Kashikura, Yoshihiko Iketani, Yuki Sato
  • Patent number: 11406965
    Abstract: A catalyst comprising chromia and at least one additional metal or compound thereof and wherein the catalyst has a total pore volume of greater than 0.3 cm3/g and the mean pore diameter is greater than or equal to 90 ?, wherein the total pore volume is measured by N2 adsorption porosimetry and the mean pore diameter is measured by N2 BET adsorption porosimetry, and wherein the at least one additional metal is selected from Li, Na, K, Ca, Mg, Cs, Sc, Al, Y, Ti, Zr, Hf, V, Nb, Ta, Cr, Mo, W, Mn, Re, Fe, Ru, Co, Rh, Ir, Ni, Pd, In, Pt, Cu, Ag, Au, Zn, La, Ce and mixtures thereof.
    Type: Grant
    Filed: September 7, 2017
    Date of Patent: August 9, 2022
    Assignee: Mexichem Fluor S.A. de C.V.
    Inventors: Claire Nicola Rees, Claire Elizabeth McGuinness, Andrew Paul Sharratt
  • Patent number: 10927469
    Abstract: A production method of aluminum including: a step of synthesizing an aluminum compound from a mixture including a halogenated aluminum hydrate and a perfluoroalkylsulfonimide-type or perfluoroalkylsulfonamide-type ionic liquid represented by general formula (1); a step of dissolving the aluminum compound in a nitrile-based organic solvent to prepare an aluminum electrolyte; a step of adding at least one ligand selected from a phosphorus compound and an organic compound having an amide group to the aluminum electrolyte and dehydrating water molecules from a hydrate included in the aluminum electrolyte; and a step of electrodepositing aluminum on a cathode by allowing electricity to pass between an anode and the cathode in the aluminum electrolyte after the dehydrating step.
    Type: Grant
    Filed: October 24, 2019
    Date of Patent: February 23, 2021
    Assignee: UACJ CORPORATION
    Inventors: Junji Nunomura, Yoichi Kojima, Mikito Ueda
  • Patent number: 10519083
    Abstract: The present invention provides a method for efficiently producing 1-chloro-3,3,3-trifluoropropene from a low-reactivity intermediate product. More specifically, provided is a method for producing trans-1-chloro-3,3,3-trifluoropropene, characterized by reacting a halogenated C3 hydrocarbon compound represented by the following general formula (1) with hydrogen fluoride in a gas phase in the presence of a solid catalyst and chlorine C3HXClYFZ??(1) wherein X is 2 or 3; when X=2, Y is an integer of 1 to 4, Z is an integer of 0 to 3, and Y+Z=4; and, when X=3, Y is an integer of 1 to 5, Z is an integer of 0 to 4, and Y+Z=5; provided that the general formula (1) represents any halogenated C3 hydrocarbon compound other than trans-1-chloro-3,3,3-trifluoropropene.
    Type: Grant
    Filed: January 12, 2017
    Date of Patent: December 31, 2019
    Assignee: Central Glass Company, Limited
    Inventors: Satoru Okamoto, Koji Ueda, Takamasa Kitamoto
  • Patent number: 10487030
    Abstract: There are provided: a solvent composition which is excellent in solubility of various organic substances and excellent in detergency, and has no adverse effect on a global environment, is excellent in stability, and is capable of suppressing corrosion of metal; a cleaning method using the solvent composition; a method of forming a coating film; a heat transfer fluid including the solvent composition; and a heat cycle system using the heat transfer fluid. A solvent composition including HCFO-1233yd and HCFC-244ca, in which a content of HCFC-244ca to a total of HCFO-1233yd and HCFC-244ca is 0.0001 to 1 mass %, a cleaning method of contacting the solvent composition with an article, a method of forming a coating film consisting of the nonvolatile organic compound using the solvent composition and a nonvolatile organic compound, a heat transfer fluid including the solvent composition, and a heat cycle system using the heat transfer fluid.
    Type: Grant
    Filed: January 9, 2018
    Date of Patent: November 26, 2019
    Assignee: AGC Inc.
    Inventors: Masahiko Nakamura, Hiroaki Mitsuoka, Mari Ichinokawa, Atsushi Fujimori, Hidekazu Okamoto
  • Patent number: 10301236
    Abstract: The disclosure relates to a method for hydrofluorination of an olefin of the formula: RCX=CYZ to produce a hydrofluoroalkane of formula RCXFCHYZ or RCHXCFYZ, wherein X, Y, and Z are independently the same or different and are selected from the group consisting of H, F, Cl, Br, and C1-C6 alkyl which is partially or fully substituted with chloro or fluoro or bromo; and R is a C1-C6 alkyl which is unsubstituted or substituted with chloro or fluoro or bromo, comprising reacting the olefin with HF in the liquid-phase, in the presence of SbF5, at a temperature ranging from about ?30° C. to about 65° C.
    Type: Grant
    Filed: May 20, 2016
    Date of Patent: May 28, 2019
    Assignee: THE CHEMOURS COMPANY FC, LLC
    Inventors: Xuehui Sun, Mario Joseph Nappa, Karl Krause
  • Patent number: 10266464
    Abstract: This invention provides a process for producing 2-chloro-3,3,3-trifluoropropene, comprising: reacting anhydrous hydrogen fluoride with at least one chlorine-containing compound selected from the group consisting of chloropropanes and chloropropenes represented by specific formulas in a gas phase in the presence of a chromium atom-containing fluorination catalyst while heating, the reaction being carried out in the presence of molecular chlorine or with a water content in the reaction system of 300 ppm or less. This invention enables suppression of catalyst deterioration and efficient production of 2-chloro-3,3,3-trifluoropropene in a simple and economically advantageous manner on an industrial scale.
    Type: Grant
    Filed: October 23, 2012
    Date of Patent: April 23, 2019
    Assignee: DAIKIN INDUSTRIES, LTD.
    Inventors: Yuzo Komatsu, Masayuki Kishimoto
  • Patent number: 10011546
    Abstract: Provided are azeotropic or azeotrope-like mixtures of 1,1,3,3-tetrachloroprop-1-ene (HCO-1230za) and hydrogen fluoride. Such compositions are useful as feed stock in the production of HFC-245fa and HCFO-1233zd.
    Type: Grant
    Filed: April 11, 2016
    Date of Patent: July 3, 2018
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Hsueh Sung Tung, Konstantin A. Pokrovski, Haiyou Wang, Stephen A. Cottrell, Hang T. Pham
  • Patent number: 9963410
    Abstract: The present invention provides a method for producing 1233yd that enables high conversion of the starting compound and high selectivity of 1233yd. The present invention provide a method for producing 1-chloro-2,3,3-trifluoropropene (1233yd), comprising the step of dehydrofluorinating 3-chloro-1,1,2,2-tetrafluoropropane (244ca).
    Type: Grant
    Filed: February 23, 2016
    Date of Patent: May 8, 2018
    Assignee: DAIKIN INDUSTRIES, LTD.
    Inventors: Daisuke Karube, Satoshi Ohishi, Michiaki Okada
  • Patent number: 9932282
    Abstract: A method for producing 1-chloro-3,3,3-trifluoropropene efficiently from an intermediate product having a low reactivity is provided. A method for producing trans-1-chloro-3,3,3-trifluoropropene comprising reacting a halogenated hydrocarbon compound having 3 carbon atoms represented by Formula (1) shown below in a gas phase with hydrogen fluoride in the presence of chlorine is provided. C3HXClYFZ (1) wherein X is 2 or 3; and when X=2, Y is an integer from 1 to 4, Z is an integer from 0 to 3, and Y+Z=4; and when X=3, Y is an integer from 1 to 5, Z is an integer from 0 to 4, and Y+Z=5; provided that Formula (1) shown above represents a halogenated hydrocarbon compound having 3 carbon atoms excluding trans-1-chloro-3,3,3-trifluoropropene.
    Type: Grant
    Filed: January 6, 2017
    Date of Patent: April 3, 2018
    Assignee: CENTRAL GLASS COMPANY, LIMITED
    Inventors: Satoru Okamoto, Fuyuhiko Sakyu, Masatomi Kanai, Takamasa Kitamoto
  • Patent number: 9862662
    Abstract: The present invention discloses high purity E-1-chloro-3,3,3-trifluoropropene (1233zd(E)) and methods to produce the same. More specifically, the present invention discloses the methods of making 1233zd(E) essentially free of toxic impurities (e.g. 2-chloro-3,3,3-trifluoropropene (1233xf), chlorotetrafluoro-propene (1224), and 3,3,3-trifluoropropyne). The present invention further provides methods for making high purity 1233zd(E) with concentration of 1233xf and 1224 at or below 200 parts per million (ppm) and 3,3,3-trifluoropropyne impurities at or below 20 ppm. Formation of 1233xf impurity can be avoided if pure 1,1,1,3,3-pentachloropropane is used as a starting material. It was also found that formation of 1233xf is avoided if a liquid phase manufacturing process is used.
    Type: Grant
    Filed: August 31, 2015
    Date of Patent: January 9, 2018
    Assignee: Honeywell International Inc.
    Inventors: Konstantin A. Pokrovski, Rajiv Ratna Singh, Ian Shankland, Hsueh Sung Tung
  • Patent number: 9708234
    Abstract: The present invention provides a process for producing a fluoroolefin by reacting, in a gas phase, a fluorinating agent and a chlorine-containing alkene or a chlorine-containing alkane in the presence of at least one catalyst selected from the group consisting of chromium oxide, at least part of which is crystallized, and fluorinated chromium oxide obtained by fluorinating the chromium oxide. According to the present process, a target fluoroolefin can be obtained at a high conversion rate of the starting material and with high selectivity.
    Type: Grant
    Filed: July 10, 2013
    Date of Patent: July 18, 2017
    Assignee: DAIKIN INDUSTRIES, LTD.
    Inventors: Takehiro Chaki, Daisuke Karube, Masami Nishiumi
  • Patent number: 9592412
    Abstract: Various compositions, including particularly aerosol compositions, containing fluorinated olefins, including particularly tetra- and penta-fluoropropenes, in a variety of applications are disclosed.
    Type: Grant
    Filed: June 27, 2016
    Date of Patent: March 14, 2017
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Rajiv R. Singh, Hang T. Pham, David P. Wilson, Raymond H. Thomas, Gary Knopeck
  • Patent number: 9487459
    Abstract: The present invention provides a method for producing a fluorine-containing olefin, the method comprising reacting a chlorine-containing compound represented by a specific formula with anhydrous hydrogen fluoride in the presence of a chromium atom-containing fluorination catalyst, the reaction being carried out at a temperature within the range of 200 to 350° C. in the presence of 0.0001 to 0.03 mol of molecular chlorine per mol of the chlorine-containing compound. The present invention is capable of achieving the effect of suppressing catalyst deterioration, maintaining the starting material conversion and the target product selectivity within excellent ranges, and reducing adverse effects caused by the use of a large amount of non-condensable gas.
    Type: Grant
    Filed: March 7, 2014
    Date of Patent: November 8, 2016
    Assignee: DAIKIN INDUSTRIES, LTD.
    Inventors: Daisuke Karube, Tatsuya Takakuwa, Yuzo Komatsu
  • Patent number: 9272969
    Abstract: Provided are azeotropic or azeotrope-like mixtures of 1,3,3-trichloro-1,1-difluoro-propane (HCFC-242fa) and hydrogen fluoride. Such compositions are useful as a feed stock or intermediate in the production of HFC-245fa and HCFO-1233zd.
    Type: Grant
    Filed: March 13, 2013
    Date of Patent: March 1, 2016
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh Sung Tung, Haiyou Wang, Stephen A. Cottrell, Hang T. Pham
  • Patent number: 9255044
    Abstract: Process of catalytic fluorination in liquid phase of product 2-chloro-3,3,3-trifluoropropene into product 2-chloro-1,1,1,2-tetrafluoropropane, with an ionic liquid based catalyst. Process for manufacturing 2,3,3,3-tetrafluoropropene.
    Type: Grant
    Filed: October 25, 2010
    Date of Patent: February 9, 2016
    Assignee: Arkema France
    Inventors: Anne Pigamo, Laurent Wendlinger, Philippe Bonnet
  • 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: 8987533
    Abstract: A production method of 1-chloro-3,3,3-trifluoropropene according to the present invention includes reaction of 1,1,1,3,3-pentachloropropane with hydrogen fluoride, characterized in that the concentrations of respective catalytic components in the 1,1,1,3,3-pentachloropropane as the raw material is controlled to a predetermined level or less. By controlling the concentrations of the respective catalytic components in the 1,1,1,3,3-pentachloropropane to the predetermined level or less, it is possible to improve the problems of shortening of catalyst life, retardation of reaction and scaling or corrosion of equipment in the production of the 1-chloro-3,3,3-trifluoropropene. In addition, the 1,1,1,3,3-pentachloropropane can be obtained selectively with high yield by telomerization reaction of carbon tetrachloride and vinyl chloride. The present invention is thus useful as the method for industrially advantageous, high-yield production of the 1-chloro-3,3,3-trifluoropropene.
    Type: Grant
    Filed: November 22, 2012
    Date of Patent: March 24, 2015
    Assignee: Central Glass Company, Limited
    Inventors: Yasuo Hibino, Satoshi Yoshikawa, Fuyuhiko Sakyu
  • 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
  • Publication number: 20140100393
    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 the presence of a fluorination catalyst, where by using 2-chloro-3,3,3,-trifluoropropene (HCFO-1233xf) of high purity, the need to add an oxidizing agent (typically chlorine) to keep the catalyst active can be avoided. The HCFC-244bb is then used as an intermediate in the production of 2,3,3,3-tetrafluoropropene-1 (HFO-1234yf).
    Type: Application
    Filed: June 28, 2010
    Publication date: April 10, 2014
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Robert C. Johnson, Daniel C. Merkel
  • 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: 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
  • Publication number: 20130102815
    Abstract: The invention provides a process for the preparation of 2,3,3,3-tetrafluoropropene (1234yf) comprising (a) contacting 1,1,1-trifluoro-2,3-difluoropropane (243db) with hydrogen fluoride (HF) in the presence of a zinc/chromia catalyst to produce a compound having the formula CF3CHFCH2X, wherein X is Cl or F, and (b) dehydrohalogenating the
    Type: Application
    Filed: December 12, 2012
    Publication date: April 25, 2013
    Applicant: Mexichem Amanco Holding S.A. de C.V.
    Inventor: Mexichem Amanco Holding S.A. de C.V.
  • Patent number: 8426656
    Abstract: The disclosed integrated manufacturing process includes a combined liquid phase reaction and purification operation which directly produces trans-1-chloro-3,3,3-trifluoropropene and 3-chloro-1,1,1,3-tetrafluoropropane which is a precursor to the manufacture of trans-1,3,3,3-tetrafluoropropene. The mixture of co-products is easily separated by conventional distillation and 3-chloro-1,1,1,3-tetrafluoropropane is then dehydrochlorinated to produce trans-1,3,3,3-tetrafluoropropene by contacting in the liquid phase with a caustic solution or in the vapor phase using a dehydrochlorination catalyst.
    Type: Grant
    Filed: April 5, 2010
    Date of Patent: April 23, 2013
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Robert Johnson, Hsueh Sung Tung, Haiyou Wang, Konstantin A. Pokrovski
  • Patent number: 8378158
    Abstract: Disclosed are azeotropic and azeotrope-like mixtures of (Z)-1-chloro-3,3,3-trifluoropropene (1233zd(Z)) and hydrogen fluoride. Such compositions are useful as an intermediate in the production of 1233zd(Z). The latter compound is useful as a nontoxic, zero ozone depleting fluorocarbon useful as a solvent, blowing agent, refrigerant, cleaning agent, aerosol propellant, heat transfer medium, dielectric, fire extinguishing composition and power cycle working fluid.
    Type: Grant
    Filed: October 5, 2011
    Date of Patent: February 19, 2013
    Assignee: Honeywell International Inc.
    Inventors: Ryan Hulse, Hang T. Pham
  • Patent number: 8309774
    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: Grant
    Filed: March 9, 2012
    Date of Patent: November 13, 2012
    Assignee: Arkema France
    Inventors: Anne Pigamo, Dominique Deur-Bert, Laurent Wendlinger
  • Publication number: 20120203036
    Abstract: A multi-step process for preparing 2,3,3,3-tetrafluoro-1-propene comprising the steps of (a) contacting a starting material comprising 2-chloro-3,3,3-trifluoro-1-propene with hydrogen fluoride in the presence of activated first catalyst selected from the group consisting of antimony-halides, iron-halides, titanium halides, and tin-halides, to produce an intermediate composition; and (b) contacting said intermediate composition with a second catalyst of activated carbon to produce a final product comprising 2,3,3,3-tetrafluoro-1-propene.
    Type: Application
    Filed: November 5, 2008
    Publication date: August 9, 2012
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Sudip Mukhopadhyay, Barbara A. Light, Kim M. Fleming, Steven D. Phillips, Rajesh K. Dubey
  • 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: 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: 8158836
    Abstract: The invention is directed to a process for preparing 2,3,3,3-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, 2,3,3,3-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: Grant
    Filed: December 23, 2010
    Date of Patent: April 17, 2012
    Assignee: Arkema France
    Inventors: Anne Pigamo, Dominique Deur-Bert, Laurent Wendlinger
  • Patent number: 8071826
    Abstract: A process for the preparation of 2,3,3,3-tetrafluoropropene (HFO-1234yf). HFO-1234yf is a refrigerant with low global warming potential. A process comprises a) reacting chlorotrifluoroethylene with a methyl halide to form an intermediate product stream; and b) reacting the intermediate product stream with hydrogen fluoride to thereby produce a result comprising 2,3,3,3-tetrafluoropropene.
    Type: Grant
    Filed: February 24, 2009
    Date of Patent: December 6, 2011
    Assignee: Honeywell International Inc.
    Inventor: Michael Van Der Puy
  • Publication number: 20100331583
    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 the presence of a fluorination catalyst, where by using 2-chloro-3,3,3,-trifluoropropene (HCFO-1233xf) of high purity, the need to add an oxidizing agent (typically chlorine) to keep the catalyst active can be avoided. The HCFC-244bb is then used as an intermediate in the production of 2,3,3,3-tetrafluoropropene-1 (HFO-1234yf).
    Type: Application
    Filed: June 28, 2010
    Publication date: December 30, 2010
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Robert C. Johnson, Daniel C. Merkel
  • Publication number: 20100191025
    Abstract: The present invention relates to a process for preparing (hydro)(chloro)fluoroolefins comprising at least one step of fluorination in the liquid phase of a (hydro)haloalkane or of a (hydro)haloalkene in the presence of at least one ionic liquid as a catalyst. The ionic liquids are derivatives of Lewis acids based on aluminum, titanium, niobium, tantalum, tin, antimony, nickel, zinc or iron.
    Type: Application
    Filed: May 13, 2008
    Publication date: July 29, 2010
    Applicant: Arkema France
    Inventor: Sylvain Perdrieux
  • Publication number: 20100185027
    Abstract: The present invention involves methods for isomerization of 1234zc. Also provided are methods for managing 1,1,3,3-tetrafluoropropene produced as a byproduct in a process for synthesizing trans-1,3,3,3-tetrafluoropropene from 245fa, wherein 1234zc is converted into trans/cis-1234ze with the help of a catalyst in the absence of HF and in an isomerization reactor, or is converted into 1234zc and/or 245fa with the help of a catalyst in the presence of HF in a separate reactor or preferably in the same reactor of 245fa dehydrofluorination.
    Type: Application
    Filed: January 13, 2010
    Publication date: July 22, 2010
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: HAIYOU WANG, KONSTANTIN A. POKROVSKI, HSUEH S. TUNG, Michael Van Der Puy
  • Patent number: 7714177
    Abstract: Disclosed is a process for the synthesis of 1,3,3,3-tetrafluoropropene comprising: a) reacting a compound of the formula (I) CHFX2 with a compound of formula (II) CH2?CF2 to produce a reaction product comprising a compound of formula (III) CHXFCH2CXF2, wherein each X is independently selected from the group consisting of chlorine, bromine and iodine; and (b) exposing said compound of formula (III) to reaction conditions effective to convert said compound to 1,3,3,3-tetrafluoropropene.
    Type: Grant
    Filed: January 7, 2008
    Date of Patent: May 11, 2010
    Assignee: Honeywell International Inc.
    Inventors: Sudip Mukhopadhyay, Haridasan K. Nair, Hsueh S. Tung, Michael Van Der Puy
  • Patent number: 7659436
    Abstract: A process for the manufacture of CF3CH2CHF2 and/or CF3CH2CF3 is disclosed. The process involves (a) reacting HF and at least one halopropene of the formula CX3CCI?CCIX (where each X is independently F or Cl) to produce a product including both CF3CCI?CF2 and CF3CHCICF3; (b) reacting CF3CCI?CF2 and/or CF3CHCICF3 produced in (a) with hydrogen to produce a product including CF3CH2CHF2 and/or CF3CH2CF3; and (c) recovering CF3CH2CHF2 and/or CF3CH2CF3 from the product produced in (b). In (a), the CF3CCI?CF2 and CF3CHCICF3 are produced in the presence of a fluorination catalyst comprising at least one chromium-containing component selected from (i) a crystalline alpha-chromium oxide where at least 0.05 atom % of the chromium atoms in the alpha-chromium oxide lattice are replaced by divalent copper, and (ii) a chromium-containing composition of (i) which has been treated with a fluorinating agent.
    Type: Grant
    Filed: August 4, 2006
    Date of Patent: February 9, 2010
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Velliyur Nott Mallikarjuna Rao, H. David Rosenfeld, Allen Capron Sievert, Shekhar Subramoney
  • Publication number: 20100010277
    Abstract: A process is disclosed to increase the Z/E ratio of 1,2,3,3,3-pentafluoropropene. The process involves contacting a starting material comprising 1,2,3,3,3-pentafluoropropene with a catalyst on AlF3 or carbon, wherein the catalyst is selected from the group consisting of SbClwF5-w, TiClxF4-x, SnClyF4-y and TaCl2F5-z wherein w is from 0 to 4, x is from 0 to 3, y is from 0 to 3, z is from 0 to 4, to obtain a product wherein the Z/E ratio of 1,2,3,3,3-pentafluoropropene is increased relative to the Z/E ratio of 1,2,3,3,3-pentafluoropropene in the starting material. A process is also disclosed to decrease the Z/E ratio of 1,2,3,3,3-pentafluoropropene.
    Type: Application
    Filed: July 11, 2007
    Publication date: January 14, 2010
    Inventors: Mario Joseph Nappa, Donald J. Toton
  • Publication number: 20090124837
    Abstract: A multi-step process for preparing 2,3,3,3-tetrafluoro-1-propene comprising the steps of (a) contacting a starting material comprising 2-chloro-3,3,3-trifluoro-1-propene with hydrogen fluoride in the presence of activated first catalyst selected from the group consisting of antimony-halides, iron-halides, titanium halides, and tin-halides, to produce an intermediate composition; and (b) contacting said intermediate composition with a second catalyst of activated carbon to produce a final product comprising 2,3,3,3-tetrafluoro-1-propene.
    Type: Application
    Filed: November 5, 2008
    Publication date: May 14, 2009
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Sudip Mukhopadhyay, Barbara A. Light, Kim M. Fleming, Steven D. Phillips, Rajesh K. Dubey
  • Patent number: 7504358
    Abstract: A crystalline alpha-chromium oxide where from about 0.05 atom % to about 2 atom % of the chromium atoms in the alpha-chromium oxide lattice are substituted by nickel atoms, and optionally, additional chromium atoms in the alpha-chromium oxide lattice are substituted by trivalent cobalt atoms (provided that the total amount of the nickel atoms and the trivalent cobalt atoms in the alpha-chromium oxide lattice is no more than 6 atom %) is disclosed. Also disclosed is a chromium-containing catalyst composition comprising as a chromium-containing component the crystalline substituted alpha-chromium oxide; and a method for preparing a composition comprising the crystalline substituted alpha-chromium oxide.
    Type: Grant
    Filed: August 21, 2003
    Date of Patent: March 17, 2009
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Velliyur Nott Mallikarjuna Rao, H. David Rosenfeld, Allen C. Sievert, Shekhar Subramoney, Munirpallam Appadorai Subramanian
  • Publication number: 20080262276
    Abstract: Methods and systems for producing hydrofluorocarbon with an inorganic fluoride (e.g., germanium tetrafluoride (GeF4)) are disclosed herein.
    Type: Application
    Filed: September 11, 2007
    Publication date: October 23, 2008
    Inventor: Bamidele Omotowa
  • Patent number: 7348461
    Abstract: Methods and materials are provided for the production of essentially isomerically pure perhalogenated and partially halogenated compounds. One embodiment of the present invention provides a process for the production of essentially isomerically pure CFC-216aa. Other embodiments include processes for the production of CFC-217ba and HFC-227ea. Particular embodiments of the present invention provide separation techniques for the separation of chlorofluorocarbons from HF, from other chlorofluorocarbons, and the separation of isomers of halogenated compounds. Still other embodiments of the present invention provide catalytic synthetic techniques that demonstrate extended catalyst lifetime. In other embodiments, the present invention provides catalytic techniques for the purification of isomeric mixtures.
    Type: Grant
    Filed: October 31, 2003
    Date of Patent: March 25, 2008
    Assignee: Great Lakes Chemical Corporation
    Inventors: Yuichi Iikubo, Stephen Owens, Mitchel Cohn, Stephan M. Brandstadter, Vicki E. Hedrick, Janet K. Boggs, John Qian, Julie Sacarias
  • Patent number: 7345209
    Abstract: Disclosed is a process for the synthesis of 1,3,3,3-tetrafluoropropene that comprises, in one preferred embodiment, providing a compound of the formula CF3CH2CHFX, wherein X is a selected from the group consisting of chlorine, bromine and iodine, and exposing said compound to reaction conditions effective to convert said compound to 1,3,3,3-tetrafluoropropene. Other processes for forming 1,3,3,3-tetrafluoropropene are also disclosed.
    Type: Grant
    Filed: April 29, 2005
    Date of Patent: March 18, 2008
    Assignee: Honeywell International Inc.
    Inventors: Sudip Mukhopadhyay, Haridasan K. Nair, Hsueh S. Tung, Michael Van Der Puy
  • Publication number: 20080051611
    Abstract: This invention relates a process for the manufacture of the HFO trans-1,3,3,3-tetrafluoropropene (HFO trans-1234ze). More particularly, the invention pertains to a process for the manufacture of the HFO trans-1234ze by first dehydrofluorinating 1,1,1,3,3-pentafluoropropane to thereby produce a mixture of cis-1,3,3,3-tetrafluoropropene, trans-1,3,3,3-tetrafluoropropene and hydrogen fluoride. Then optionally recovering hydrogen fluoride and then recovering trans-1,3,3,3-tetrafluoropropene.
    Type: Application
    Filed: July 10, 2007
    Publication date: February 28, 2008
    Inventors: Haiyou Wang, Hsueh Sung Tung
  • Patent number: 7329786
    Abstract: Methods and materials are provided for the production of essentially isomerically pure perhalogenated and partially halogenated compounds. One embodiment of the present invention provides a process for the production of essentially isomerically pure CFC-216aa. Other embodiments include processes for the production of CFC-217ba and HFC-227ea. Particular embodiments of the present invention provide separation techniques for the separation of chlorofluorocarbons from HF, from other chlorofluorocarbons, and the separation of isomers of halogenated compounds. Still other embodiments of the present invention provide catalytic synthetic techniques that demonstrate extended catalyst lifetime. In other embodiments, the present invention provides catalytic techniques for the purification of isomeric mixtures.
    Type: Grant
    Filed: September 28, 2001
    Date of Patent: February 12, 2008
    Assignee: Great Lakes Chemical Corporation
    Inventors: Yuichi Iikubo, Stephen Owens, Mitchel Cohn, Stephan M. Brandstadter, Vicki E. Hedrick, Janet K. Boggs, John Chengping Chien, Julie Sacarias, Vimal Sharma
  • Patent number: 7317071
    Abstract: Processes for producing a fluoromonomer from a fluoropolymer, among which one that can be carried out more simply is a process wherein thermal decomposition of a fluoropolymer is preformed by means of a rotary kiln (5) so as to produce a fluoromonomer, the process comprising feeding a fluoropolymer and steam (3) into a rotary kiln and heating the fluoropolymer.
    Type: Grant
    Filed: February 27, 2003
    Date of Patent: January 8, 2008
    Assignee: Daikin Industries, Ltd.
    Inventors: Takuya Ichida, Yukio Homoto
  • Patent number: 7312367
    Abstract: The invention provides an economic process for the manufacture of the hydrofluorocarbon 1,1,3,3,3-pentafluoropropene (HFC-1225zc). HFC-1225zc can be made from the dehydrochlorination of 1-chloro-1,1,3,3,3-pentafluoropropane (HCFC-235fa). Alternatively, HFC-1225zc can also be made from the dehydrofluorination of 1,1,1,3,3,3-hexafluoropropane (HFC-236fa). HFC-1225zc) is a compound that has the potential to be used as a low Global Warming Potential refrigerant, blowing agent, aerosol propellant, or solvent.
    Type: Grant
    Filed: June 14, 2006
    Date of Patent: December 25, 2007
    Assignee: Honeywell International Inc.
    Inventors: Hsueh Sung Tung, Daniel C. Merkel, Rajiv R. Singh