Preparing Unsaturated Compound Patents (Class 570/153)
  • Patent number: 8436216
    Abstract: A process is disclosed for making 1,1,1,4,4,4-hexafluoro-2-butene. The process involves reacting 2,2-dichloro-1,1,1-trifluoroethane with copper in the presence of an amide solvent and 2,2?-bipyridine. A process is also disclosed for making 1,1,1,4,4,4-hexafluoro-2-butene. The process involves reacting 2,2-dichloro-1,1,1-trifluoroethane with copper in the presence of an amide solvent and a Cu(I) salt. A process is further disclosed for making 1,1,1,4,4,4-hexafluoro-2-butene. The process involves reacting 2,2-dichloro-1,1,1-trifluoroethane with copper in the presence of an amide solvent, 2,2?-bipyridine and a Cu(I) salt.
    Type: Grant
    Filed: March 18, 2009
    Date of Patent: May 7, 2013
    Assignee: E I du Pont de Nemours and Company
    Inventors: Xuehui Sun, Mario Joseph Nappa, Win-Chung Lee
  • Patent number: 8436217
    Abstract: Disclosed is a fully integrated process for making 1,1,1,3,3-pentafluoropropane (HFC-245fa), trans-1-chloro-3,3,3-trifluoropropene (HCFO-1233zd(E)), and trans-1,3,3,3-tetrafluoropropene (HFO-1234ze(E)).
    Type: Grant
    Filed: April 25, 2011
    Date of Patent: May 7, 2013
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh Sung Tung, Ian Shankland
  • Publication number: 20130098396
    Abstract: Disclosed are compositions comprising unsaturated hydrofluorocarbons, an alkene with the formula of 1,1,1,4,4,5,5,6,6,6-decafluorohex-2-ene and its isomers (the “153-10 isomers”). The invention further relates to use of said compositions in methods to clean, degrease, deflux, dewater, deposit fluorolubricant, carrier fluid applications and heat transfer applications. The invention further relates to novel 153-10 isomer mixtures, their method of making and their use as cleaning compositions and in the methods listed above.
    Type: Application
    Filed: October 8, 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: 8410324
    Abstract: A process for isomerising a (hydrohalo)fiuoroalkene, the process comprising contacting the (hydrohalo)fluoroalkene with a catalyst comprising an unsupported Lewis acid, a chromia-containing catalyst containing at least one additional metal, an alumina, a supported liquid catalyst, and mixtures thereof.
    Type: Grant
    Filed: April 11, 2008
    Date of Patent: April 2, 2013
    Assignee: Mexichem Amanco Holding, S.A. de C.V.
    Inventors: Andrew Paul Sharratt, John Charles McCarthy
  • Patent number: 8404907
    Abstract: Disclosed is a process for making one isomer of CF3CH?CHCl. More particularly, the invention comprises the production of CF3C?CCl and its selective reduction to cis-1-chloro-3,3,3-trifluoropropene (CF3CH?CHCl).
    Type: Grant
    Filed: February 18, 2011
    Date of Patent: March 26, 2013
    Assignee: Honeywell International Inc.
    Inventors: Haridasan K. Nair, Andrew Joseph Poss, Rajiv Ratna Singh, Michael Van Der Puy, Ryan J. Hulse
  • Publication number: 20130060068
    Abstract: A process is disclosed for making CF3CH2CHF2, CF3CH?CHF, and/or CF3CH?CHCl. This process involves reacting at least one starting material selected from the group consisting of halopropenes of the formula CX3CH?CH2 and halopropenes of the formula CX2?CHCH2X, wherein each X is independently F or Cl, with HF and Cl2 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. The molar ratio of HF to the total amount of starting materials fed to the reaction zone is at least stoichiometric, and the molar ratio of Cl2 to total amount of starting material fed to the reaction zone is 2:1 or less.
    Type: Application
    Filed: October 23, 2012
    Publication date: March 7, 2013
    Applicant: E I DU PONT DE NEMOURS AND COMPANY
    Inventor: E I DU PONT DE NEMOURS AND COMPANY
  • Patent number: 8383867
    Abstract: Disclosed is a method for producing fluorinated organic compounds, including 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 Cl addition agent under conditions effective to produce a compound of formula (I).
    Type: Grant
    Filed: November 3, 2006
    Date of Patent: February 26, 2013
    Assignee: Honeywell International Inc.
    Inventors: Sudip Mukhopadhyay, Haridasan K. Nair, Rajesh K. Dubey, Rajiv R. Singh, George A. Shia
  • Patent number: 8350101
    Abstract: The present invention relates to the method for obtaining vinylidene fluoride and the subject matter thereof is more particularly the production of vinylidene fluoride by pyrolysis of 1,2-dichloro-2,2-difluoroethane in the presence of hydrogen at a temperature of greater than or equal to 400° C.
    Type: Grant
    Filed: August 20, 2009
    Date of Patent: January 8, 2013
    Assignee: Arkema France
    Inventors: Sylvain Perdrieux, Serge Hub
  • Patent number: 8318991
    Abstract: An unsaturated hydrogen-containing fluoroolefin compound is obtained by bringing an unsaturated fluorine-containing halogen compound into contact with 0.1 to 3 molar equivalents of hydrogen relative to the unsaturated fluorine-containing halogen compound in a vapor phase in the presence of a supported palladium catalyst in which an amount of supported palladium is 0.1% by weight to 2.5% by weight.
    Type: Grant
    Filed: July 13, 2009
    Date of Patent: November 27, 2012
    Assignee: Zeon Corporation
    Inventors: Tatsuya Sugimoto, Takefumi Suzuki, Jo Konagawa
  • 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: 20120283490
    Abstract: A system, apparatus, and method for transferring chemical solutions and synthesizing a tracer. For transferring chemical solutions, the system comprises a primary container; a secondary container; a first line in communication with the primary container and the secondary container. The first line facilitates the flow of gas and/or liquid between the primary container and the secondary container. A valve located upstream of the secondary container and downstream of the primary container regulates flow within the first line; a second line in communication with the secondary container. For synthesizing a tracer, the system includes a source of a solution having a radionuclide. A first container has a tracer precursor and is in communication with the source of solution.
    Type: Application
    Filed: April 12, 2012
    Publication date: November 8, 2012
    Applicant: SIEMENS MEDICAL SOLUTIONS USA, INC.
    Inventors: Umesh B. Gangadharmath, Joseph C. Walsh, Hartmuth C. Kolb, Ricardo Rodriguez, Arkadij M. Elizarov, Carroll Edward Ball
  • Patent number: 8299309
    Abstract: Described herein is a process for the manufacture of hydrofluoroalkanols of the structure RfCFClCHROH. Also described herein are methods of manufacturing hydrofluoroalkenes of the structure RfCF?CHR from halofluorocarbons of the structure RfCFX2. In particular, 2,3,3,3,-tetrafluoro-1-propene may be manufactured with this process. Also described are compounds of the formula RfCFClCHROC(?O)R?.
    Type: Grant
    Filed: October 11, 2011
    Date of Patent: October 30, 2012
    Assignee: E I du Pont de Nemours and Company
    Inventors: Mario Joseph Nappa, Xuehui Sun, Lev Moiseevich Yagupolskii, Andrey Anatolievich Filatov, Vladimir Nikolaevich Boiko, Yurii Lvovich Yagupolskii
  • Publication number: 20120215039
    Abstract: The present invention pertains to ternary azeotrope and azeotrope-like composition including 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), HF, and either 1,1,2,3-tetrachloropropene (TCP) or 1,1,1,2,2-pentafluoropropane (HFC-245cb). The present invention also relates to binary azeotropes of 2,3,3,3-tetrachloropropene and HF. Such azeotropic and azeotrope-like compositions are useful as intermediates in the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf).
    Type: Application
    Filed: January 23, 2012
    Publication date: August 23, 2012
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: RYAN HULSE, HANG T. PHAM, HSUEH SUNG TUNG, KONSTANTIN POKROVSKI, DANIEL C. MERKEL
  • Publication number: 20120184785
    Abstract: Disclosed is a process for the manufacture of 1234yf from 1,1,2,3-tetrachloropropene, abbreviated herein as “TCP,” in three integrated steps: (a) the R-1 hydrofluorination of TCP to form 1233xf in the vapor phase; (b) the R-2 hydrofluorination of 1233xf to form 244bb in either the liquid phase or in the liquid phase followed by the vapor phase; and (c) the R-3 dehydrochlorination of the 244bb in either the liquid or the vapor phase to produce 1234yf; wherein the vapor phase hydrofluorination of TCP in step (a) is carried out at a lower pressure than the liquid phase hydrofluorination of 123xf; and wherein the HCl generated during these steps is scrubbed with water to form an acid solution and the organic components are scrubbed with a caustic solution and then dried before further processing.
    Type: Application
    Filed: December 7, 2011
    Publication date: July 19, 2012
    Inventors: Stephen A. Cottrell, Yuon Chiu, Haluk Kopkalli, Hsueh Sung Tung, Kevin D. Uhrich, Peter Scheidle
  • Publication number: 20120178977
    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: Application
    Filed: December 7, 2011
    Publication date: July 12, 2012
    Inventors: Daniel C. Merkel, Hsueh Sung Tung, Konstantin A. Pokrovski, Haiyou Wang, Selma Bektesevic
  • Patent number: 8212091
    Abstract: A process for depolymerizing fluoropolymers includes continuously feeding a solid fluoropolymer, in particulate form, into a horizontal cylindrical first reaction zone. The fluoropolymer particles enter the first reaction zone at one end. Within the first reaction zone, a central axle from which protrudes at least one paddle, continuously rotates. The rotating paddle serves to advance the fluoropolymer particles along the reaction zone while agitating them. As the fluoropolymer particles pass along the reaction zone, they are subjected to an elevated temperature, thereby depolymerizing the fluoropolymer into a fluoro-containing compound-rich gas phase. A residual solids phase is withdrawn at the other end of the first reaction zone, as is the gas phase. Optionally, the gas phase is passed through a second reaction zone which is also at an elevated temperature. The gas phase is quenched, thereby to recover the fluoro-containing compounds as gaseous products.
    Type: Grant
    Filed: November 24, 2006
    Date of Patent: July 3, 2012
    Assignee: The South African Nuclear Energy Corporation Limited
    Inventors: Izak Jacobus Van Der Walt, Alfred Teo Grunenberg, Johannes Theodorus Nel
  • Publication number: 20120138841
    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: Application
    Filed: October 5, 2011
    Publication date: June 7, 2012
    Inventors: Ryan Hulse, Hang T. Pham
  • Publication number: 20120108859
    Abstract: The disclosure describes a process for dehalogenation of chlorofluorocompounds. The process comprises contacting a saturated chlorofluorocompound with hydrogen in the presence of a catalyst at a temperature sufficient to remove chlorine and/or fluorine substituents to produce a fluorine containing terminal olefin.
    Type: Application
    Filed: October 20, 2011
    Publication date: May 3, 2012
    Applicant: E. I. DU PONT DE NEMOURS AND COMPANY
    Inventors: MARIO JOSEPH NAPPA, Ekaterina N. Swearingen, Allen Capron Sievert, Xuehui Sun
  • 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
  • Publication number: 20120022300
    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: Application
    Filed: September 30, 2011
    Publication date: January 26, 2012
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Robert Johnson, Hsueh Sung Harry Tung
  • Publication number: 20110319677
    Abstract: The object is to provide a process for producing highly pure 2,3,3,3-tetrafluoropropene, whereby formation of 3,3,3-trifluoropropene is suppressed. A process for producing 2,3,3,3-tetrafluoropropene, which comprises reacting a raw material compound composed of 1,1-dichloro-2,3,3,3-tetrafluoropropene and/or 1-chloro-2,3,3,3-tetrafluoropropene, and hydrogen in a gas phase in a reactor having a catalyst layer packed with a catalyst-supporting carrier, while maintaining the maximum temperature of the catalyst layer to be at most 130° C., to obtain formed gas containing 2,3,3,3-tetrafluoropropene, and then, contacting the formed gas discharged from the reactor, with alkali at a temperature of at most 100° C.
    Type: Application
    Filed: June 23, 2011
    Publication date: December 29, 2011
    Applicant: Asahi Glass Company, Limited
    Inventors: Satoshi KAWAGUCHI, Hidekazu Okamoto, Yu Takeuchi, Hirokazu Takagi, Kunio Watanabe, Koichi Yanase
  • Publication number: 20110319674
    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: Application
    Filed: June 24, 2010
    Publication date: December 29, 2011
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Haiyou Wang, Hsueh Sung Tung
  • Publication number: 20110319676
    Abstract: The object is to provide a process whereby it is possible to produce 2,3,3,3-tetrafluoropropene at a high conversion ratio constantly for a long period of time. A process for producing 2,3,3,3-tetrafluoropropene, which comprises reacting a raw material compound of at least one of 1,1-dichloro-2,3,3,3-tetrafluoropropene and 1-chloro-2,3,3,3-tetrafluoropropene, and hydrogen, in the presence of a noble metal catalyst supported on active carbon having an ash content of at most 3% as measured in accordance with ASTM D2866.
    Type: Application
    Filed: June 23, 2011
    Publication date: December 29, 2011
    Applicant: ASAHI GLASS COMPANY, LIMITED
    Inventors: Hirokazu TAKAGI, Hidekazu Okamoto, Satoshi Kawaguchi, Yu Takeuchi, Kunio Watanabe, Koichi Yanase, Shingo Nomura
  • Patent number: 8076521
    Abstract: In this invention we are disclosing a process for the synthesis of hydrochlorofluoro olefins (HCFO) and/or hydrofluoroolefins (HFO). The process is based on the following steps of liquid phase, noncatalytic fluorination of hydrochloropropenes to form hydrochlorofluoropropenes and/or hydrofluoropropenes, followed by gas phase, catalytic fluorination of the hydrochlorofluoropropenes to form hydrofluoropropenes.
    Type: Grant
    Filed: June 26, 2008
    Date of Patent: December 13, 2011
    Assignee: Arkema Inc.
    Inventors: Maher Y. Elsheikh, Philippe Bonnet, Benjamin Bin Chen
  • Patent number: 8071825
    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 1, 2008
    Date of Patent: December 6, 2011
    Assignee: Honeywell International Inc.
    Inventors: Robert C. Johnson, Hsueh S. Tung, Daniel C. Merkel
  • Patent number: 8058488
    Abstract: Described herein is a process for the manufacture of hydrofluoroalkanols of the structure RfCFClCHROH, comprising reacting a halofluorocarbon of the structure RfCFX2, wherein each X is independently selected from Cl, Br, and I, with an aldehyde and a reactive metal in a reaction solvent to generate a reaction product comprising a metal hydrofluoroalkoxide, neutralizing said metal hydrofluoroalkoxide to produce a hydrofluoroalkanol, and recovering the hydrofluoroalkanol.
    Type: Grant
    Filed: November 20, 2008
    Date of Patent: November 15, 2011
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mario Joseph Nappa, Xuehui Sun, Lev Moiseevich Yagupolskii, Andrey Anatolievich Filatov, Vladimir Nikolaevich Boiko, Yurii Lvovich Yagupolskii
  • Publication number: 20110269999
    Abstract: A process for the manufacture of halogenated olefins in semi-batch mode by dehydrohalogenation of halogenated alkanes in the presence of an aqueous base such as KOH which simultaneously neutralizes the resulting hydrogen halide. During the process, aqueous base is continuously added to the haloalkane which results in better yields, lower by-product formation and safer/more controllable operation.
    Type: Application
    Filed: April 29, 2010
    Publication date: November 3, 2011
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: George R. Cook, Haluk Kopkalli, Stephen A. Cottrell, Yuon Chiu, Peter Scheidle, Daniel C. Merkel
  • Publication number: 20110172471
    Abstract: A process is disclosed for the conversion of fluorocarbons into fluorinated unsaturated compounds useful as monomers or other chemical precursors, such as C2H2F2. The process comprises reacting a hydrocarbon feed (20) arid a fluorocarbon feed (10) in a high temperature reactor (26), at sufficiently high temperature and sufficiently short resident time to form product mixture (28) having the fluorinated unsaturated compound as the major reaction product, and cooling (18) to a temperature sufficiently low to inhibit polymerisation of the unsaturated compound. The reaction product may then be processed by removal of higher molecular weight compounds (35) and acids (32) and optionally separated (44) into product components.
    Type: Application
    Filed: March 22, 2011
    Publication date: July 14, 2011
    Applicant: PACIFITECH PTY LIMITED
    Inventors: Eric Miles Kennedy, Bogdan Zygmunt Dlugogorski
  • Publication number: 20110160497
    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: Application
    Filed: December 23, 2010
    Publication date: June 30, 2011
    Applicant: Arkema France
    Inventors: Dominique Deur-Bert, Laurent Wendlinger, Anne Pigamo
  • Publication number: 20110124928
    Abstract: An apparatus for producing a gas using a raw material gas having high reactivity, in particular, a fluorinated hydrocarbon, or a vessel for supplying the gas, characterized in that the surface of a portion thereof contacting with the gas has an average roughness of 1 ?m or less in terms of a center line average roughness Ra. It is preferred that an oxide-based passivated film such as a film based on chromium oxide, aluminum oxide, yttrium oxide, magnesium oxide or the like is formed on the surface having a roughness controlled as above. The above apparatus and vessel can be suitably used for preventing the contamination of a raw material gas originated from a gas production apparatus or a vessel for supplying the gas.
    Type: Application
    Filed: January 12, 2011
    Publication date: May 26, 2011
    Applicant: Zeon Corporation
    Inventors: Tadahiro Ohmi, Yasuyuki Shirai, Takeyoshi Kato, Kimiaki Tanaka, Masahiro Nakamura, Katsutomo Tanaka
  • Publication number: 20110124929
    Abstract: The present invention provides a process for preparing a fluorine-containing propene represented by the chemical formula CF3CF?CX1X2, wherein X1 is a hydrogen atom or chlorine atom, and X2 is a fluorine atom, chlorine atom, or hydrogen atom, by reacting a halogenated propene represented by the chemical formula CCIYZCF?CX1X2, wherein X1 and X2 are the same as above, and Y and Z may be the same or different and individually indicate a fluorine atom or chlorine atom, with anhydrous hydrogen fluoride in a gas phase in the presence of a chromium oxide or a fluorinated chromium oxide as a fluorination catalyst. The process of the present invention provides a fluorine-containing propene represented by the chemical formula CF3CF?CClX, wherein X is Cl, H or F, under relatively mild conditions at a high yield.
    Type: Application
    Filed: June 25, 2009
    Publication date: May 26, 2011
    Inventors: Masatoshi Nose, Akinari Sugiyama, Atsushi Suzuki
  • Publication number: 20110118513
    Abstract: The invention provides a process for preparing 1,1,1-trifluoro-2,3-dichloropropane (243db), which process comprises contacting 3,3,3-trifluoropropene (1243zf) with chlorine in the presence of a catalyst, wherein the catalyst comprises activated carbon, alumina and/or an oxide of a transition metal.
    Type: Application
    Filed: April 9, 2009
    Publication date: May 19, 2011
    Applicant: INEOS FLUOR HOLDINGS LIMITED
    Inventors: John W. Smith, Claire McGuiness, Andrew P. Sharratt
  • Publication number: 20110112338
    Abstract: The invention provides a process for the preparation of 1234yf comprising (a) contacting 1,1,2,3,3,3-hexafluoropropene (1216) with hydrogen in the presence of a hydrogenation catalyst to produce 1,1,2,3,3,3-hexafluoropropane (236ea); (b) dehydrofluorinating 236ea to produce 1,2,3,3,3-pentafluoropropene (1225ye); (c) contacting 1225ye with hydrogen in the presence of a hydrogenation catalyst to produce 1,2,3,3,3-pentafluoropropane (245eb); and (d) dehydrofluorinating (245eb) to produce (1234yf).
    Type: Application
    Filed: May 15, 2009
    Publication date: May 12, 2011
    Applicant: MEXICHEM/ AMANCO HOLDING S.A. DE C.V.
    Inventors: John W. Smith, Claire McGuiness, Andrew P. Sharratt, Andrew M. Taylor
  • Publication number: 20110060170
    Abstract: An unsaturated hydrogen-containing fluoroolefin compound is obtained by bringing an unsaturated fluorine-containing halogen compound into contact with 0.1 to 3 molar equivalents of hydrogen relative to the unsaturated fluorine-containing halogen compound in a vapor phase in the presence of a supported palladium catalyst in which an amount of supported palladium is 0.1% by weight to 2.5% by weight.
    Type: Application
    Filed: July 13, 2009
    Publication date: March 10, 2011
    Applicant: ZEON CORPORATION
    Inventors: Tatsuya Sugimoto, Takefumi Suzuki, Jo Konagawa
  • Publication number: 20110028769
    Abstract: A process is disclosed for making 1,1,1,4,4,4-hexafluoro-2-butene. The process involves reacting 2,2-dichloro-1,1,1-trifluoroethane with copper in the presence of an amide solvent and 2,2?-bipyridine. A process is also disclosed for making 1,1,1,4,4,4-hexafluoro-2-butene. The process involves reacting 2,2-dichloro-1,1,1-trifluoroethane with copper in the presence of an amide solvent and a Cu(I) salt. A process is further disclosed for making 1,1,1,4,4,4-hexafluoro-2-butene. The process involves reacting 2,2-dichloro-1,1,1-trifluoroethane with copper in the presence of an amide solvent, 2,2?-bipyridine and a Cu(I) salt.
    Type: Application
    Filed: March 18, 2009
    Publication date: February 3, 2011
    Applicant: E.I. Du Pont De Nemours and Company
    Inventors: Xuehui Sun, Mario Joseph Nappa, Win-Chung Lee
  • Patent number: 7829748
    Abstract: The invention provides an economic process for the manufacture of 1,3,3,3-tetrafluoropropene (HFO-1234ze) by a two stage process. A vapor phase hydrofluorination of 1-chloro-3,3,3-trifluoropropene (HCFC-1233zd) into 1-chloro-1,3,3,3-tetrafluoropropane (HCFC-244fa) and/or 1,1,1,3,3-pentafluoropropane (HFC-245fa) is conducted, followed by the thermal dehydrochlorination of HCFC-244fa and dehydro fluorination of HFC-245fa into HFO-1234ze in the presence of a catalyst which comprises one or more of alkali metal halides, alkaline earth metal halides, halogenated metal oxides, zero oxidation state metals, zinc halides, palladium halides, and activated carbon.
    Type: Grant
    Filed: September 21, 2009
    Date of Patent: November 9, 2010
    Assignee: Honeywell International Inc.
    Inventors: Hsuehsung Tung, Robert C. Johnson, Daniel C. Merkel, Haiyou Wang
  • Publication number: 20100210883
    Abstract: Disclosed are methods for producing fluorinated organic compounds, including hydrofluoropropenes, which preferably comprises converting at least one compound of formula (I): CF3CHXCH2X ??(I) to at least one compound of formula (II) CF3CZCHZ ??(II). where X is independently Cl, Br, I or F, and Z independently is H or F. In certain preferred embodiments, each Z is different.
    Type: Application
    Filed: February 8, 2010
    Publication date: August 19, 2010
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Sudip Mukhopadhyay, Haridasan K. Nair, Hsueh S. Tung, Michael Van Der Puy, Daniel C. Merkel, Rajesh K. Dubey, Jing Ji Ma
  • Publication number: 20100145110
    Abstract: A process is disclosed for the conversion of fluorocarbons into fluorinated unsaturated compounds useful as monomers or other chemical precursors, such as C2H2F2. The process comprises reacting a hydrocarbon feed (20) and a fluorocarbon feed (10) in a high temperature reactor (26), at sufficiently high temperature and sufficiently short resident time to form a reaction product mixture (28) having the fluorinated unsaturated compound as the major reaction product, and cooling (18) to a temperature sufficiently low to inhibit polymerisation of the unsaturated compound. The reaction product may then be processed by removal of higher molecular weight compounds (35) and acids (32) and optionally separated (44) into product components.
    Type: Application
    Filed: September 14, 2009
    Publication date: June 10, 2010
    Applicant: Pacifitech PTY Limited
    Inventors: Eric Miles Kennedy, Bogdan Zygmunt Dlugogorski
  • Publication number: 20100121117
    Abstract: Disclosed herein is a process of preparing decafluorocyclohexene using hexafluorobenzene as a raw material. The hexafluorobenzene reacts with an activated fluorinating agent at 60-200° C. in an inert gas atmosphere. The activated fluorinating agent is prepared by mixing 1-50 wt % of cobalt difluoride with 50-99 wt % of other metal fluoride selected from calcium fluoride, magnesium fluoride, aluminum fluoride, sodium fluoride and potassium fluoride. The mixture reacts with fluorine gas at 200-400° C.
    Type: Application
    Filed: February 19, 2009
    Publication date: May 13, 2010
    Applicant: FOOSUNG Co. Ltd.
    Inventors: Hyang Ja JANG, Jong Yool Yang, Chul Ho Kim, Young Gu Cho, Jung Eun Lee
  • Publication number: 20100121115
    Abstract: Disclosed is a process for the manufacture of hydrofluoroolefins of the structure CF3CF?CHY, wherein Y can be H or F, comprising reacting at least one fluoropropane reactant of the structure CF3CFXCFYH1 wherein X can be either F or H, and Y can be either F or H, provided that both X and Y? are not both F, with a basic aqueous solution in the presence of a non-aqueous, non-alcoholic solvent, and in the presence of a phase transfer catalyst.
    Type: Application
    Filed: September 5, 2007
    Publication date: May 13, 2010
    Applicant: E. I. DU PONT DE NEMOURS AND COMPANY
    Inventors: Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert, Mario Joseph Nappa
  • Patent number: 7700815
    Abstract: Disclosed is a method for producing fluorinated organic compounds, including petnafluoropropenes, which preferably comprises converting at least one compound of formula (I): CFnXmCFaXbCH2X??(I) to at least one compound of formula (II) CF3CF?CHF??(II) where each X is independently Cl, I or Br; n is 2 or 3; m is 0 or 1, a is 1 or 2, b is 0 or 1, m+n=3 and a+b=2.
    Type: Grant
    Filed: September 28, 2007
    Date of Patent: April 20, 2010
    Assignee: Honeywell International Inc
    Inventors: Hsueh Sung Tung, Rajiv R. Singh, Michael Van Der Puy
  • Patent number: 7592494
    Abstract: The invention provides an economic process for the manufacture of 1,3,3,3-tetrafluoropropene (HFC-1234ze) by a two stage process. A hydrofluorination of 1-chloro-3,3,3-trifluoropropene (HCFC-1233zd) into 1-chloro-1,3,3,3-tetrafluoropropane (HCFC-244fa) and 1,1,1,3,3-pentafluoropropane (HFC-245fa) is conducted, followed by the dehydrochlorination of HCFC-244fa and dehydrofluorination of HFC-245fa into HFC-1234ze.
    Type: Grant
    Filed: July 25, 2003
    Date of Patent: September 22, 2009
    Assignee: Honeywell International Inc.
    Inventors: Hsueh Sung Tung, Robert C. Johnson, Daniel C. Merkel
  • Publication number: 20090209791
    Abstract: A process for the production of fluorinated olefins, preferably fluorinated propenes, by contacting a feed stream containing a fluorinated olefin and hydrogen with a first amount of catalyst to produce the hydrofluorocarbon, wherein a first exit stream contains unreacted fluorinated olefin and hydrogen; contacting the first exit stream with a second amount of catalyst to produce a hydrofluorocarbon, wherein the second amount of catalyst is preferably greater than the first amount of catalyst; and contacting the hydrofluorocarbon with a catalyst for dehydrohalogenation to produce a product stream of fluorinated olefin.
    Type: Application
    Filed: February 19, 2009
    Publication date: August 20, 2009
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Michael Van Der Puy, George R. Cook, Peter H. Sheidle, Kevin D. Uhrich, Haiyou Wang, Hsueh Sung Tung
  • Publication number: 20090069589
    Abstract: Methods and systems for producing hydrohalocarbon and/or halocarbon compounds with an inorganic fluoride (e.g., silicon tetrafluoride (SiF4)) are disclosed herein.
    Type: Application
    Filed: September 3, 2008
    Publication date: March 12, 2009
    Applicant: International Isotopes Inc.
    Inventor: Bamidele Omotowa
  • Publication number: 20090036719
    Abstract: A process is disclosed for the conversion of fluorocarbons into fluorinated unsaturated compounds useful as monomers or other chemical precursors, such as C2H2F2. The process comprises reacting a hydrocarbon feed (20) and a fluorocarbon feed (10) in a high temperature reactor (26), at sufficiently high temperature and sufficiently short resident time to form a reaction product mixture (28) having the fluorinated unsaturated compound as the major reaction product, and cooling (18) to a temperature sufficiently low to inhibit polymerisation of the unsaturated compound. The reaction product may then be processed by removal of higher molecular weight compounds (35) and acids (32) and optionally separated (44) into product components.
    Type: Application
    Filed: August 25, 2008
    Publication date: February 5, 2009
    Applicant: Pacifitech PTY Limited
    Inventors: Eric Miles Kennedy, Bogdan Zygmunt Dlugogorski
  • Publication number: 20090012335
    Abstract: Disclosed herein is a process for the preparation of fluorine-containing olefins comprising contacting a chlorofluoroalkene with hydrogen in the presence of a catalyst at a temperature sufficient to cause replacement of the chlorine substituents with hydrogen. Also disclosed is a catalyst composition for the hydrodechlorination of chlorofluoroalkenes comprising copper metal deposited on a support.
    Type: Application
    Filed: June 27, 2008
    Publication date: January 8, 2009
    Applicant: E.I.du pont de Nemours and Company
    Inventors: Mario Joseph Nappa, Ekaterina N. Swearingen
  • Patent number: 7473810
    Abstract: Provided is a method for selectively preparing 2-chloropentafluoropropene comprising catalytic dechlorination of 1,2,2-trichloro-1,1,3,3,3-pentafluoropropane in the presence of hydrogen and a noble metal catalyst. Also provided is method for dechlorinating a vicinal chloride substituted organic compound using a palladium/barium sulfate catalyst.
    Type: Grant
    Filed: October 12, 2007
    Date of Patent: January 6, 2009
    Assignee: Honeywell International Inc.
    Inventors: Michael Van Der Puy, Jingji Ma
  • Patent number: 7439408
    Abstract: The present invention relates to a process for preparing a compound of formula (V) where R is H or F, by reacting a compound of formula (IV) where R is H or F, with hydrogen sulphide or salts thereof, optionally in the presence of a reaction auxiliary and optionally in the presence of a diluent.
    Type: Grant
    Filed: April 13, 2006
    Date of Patent: October 21, 2008
    Assignee: Bayer Cropscience AG
    Inventor: Alexander Straub
  • Publication number: 20080242901
    Abstract: A method for preparing fluorinated organic compounds wherein at least one fluorinated olefin is reacted with methyl fluoride in the gas-phase and in the presence of a Lewis Acid catalyst to form at least one product having at least 3 carbon atoms.
    Type: Application
    Filed: June 6, 2008
    Publication date: October 2, 2008
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Sudip Mukhopadhyay, Hsueh Sung Tung, Haridasan K. Nair, Jingji Ma