Preparing Unsaturated Compound Patents (Class 570/153)
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Patent number: 8436216Abstract: 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: GrantFiled: March 18, 2009Date of Patent: May 7, 2013Assignee: E I du Pont de Nemours and CompanyInventors: Xuehui Sun, Mario Joseph Nappa, Win-Chung Lee
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Patent number: 8436217Abstract: 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: GrantFiled: April 25, 2011Date of Patent: May 7, 2013Assignee: Honeywell International Inc.Inventors: Haiyou Wang, Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh Sung Tung, Ian Shankland
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Publication number: 20130098396Abstract: 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: ApplicationFiled: October 8, 2012Publication date: April 25, 2013Applicant: E I DU PONT DE NEMOURS AND COMPANYInventor: E I DU PONT DE NEMOURS AND COMPANY
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Patent number: 8426655Abstract: 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: GrantFiled: March 11, 2011Date of Patent: April 23, 2013Assignee: Honeywell International Inc.Inventors: Hsueh Sung Tung, Haiyou Wang
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Patent number: 8410324Abstract: 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: GrantFiled: April 11, 2008Date of Patent: April 2, 2013Assignee: Mexichem Amanco Holding, S.A. de C.V.Inventors: Andrew Paul Sharratt, John Charles McCarthy
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Patent number: 8404907Abstract: 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: GrantFiled: February 18, 2011Date of Patent: March 26, 2013Assignee: Honeywell International Inc.Inventors: Haridasan K. Nair, Andrew Joseph Poss, Rajiv Ratna Singh, Michael Van Der Puy, Ryan J. Hulse
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Publication number: 20130060068Abstract: 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: ApplicationFiled: October 23, 2012Publication date: March 7, 2013Applicant: E I DU PONT DE NEMOURS AND COMPANYInventor: E I DU PONT DE NEMOURS AND COMPANY
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Patent number: 8383867Abstract: 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: GrantFiled: November 3, 2006Date of Patent: February 26, 2013Assignee: Honeywell International Inc.Inventors: Sudip Mukhopadhyay, Haridasan K. Nair, Rajesh K. Dubey, Rajiv R. Singh, George A. Shia
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Patent number: 8350101Abstract: 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: GrantFiled: August 20, 2009Date of Patent: January 8, 2013Assignee: Arkema FranceInventors: Sylvain Perdrieux, Serge Hub
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Patent number: 8318991Abstract: 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: GrantFiled: July 13, 2009Date of Patent: November 27, 2012Assignee: Zeon CorporationInventors: Tatsuya Sugimoto, Takefumi Suzuki, Jo Konagawa
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Patent number: 8309774Abstract: 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: GrantFiled: March 9, 2012Date of Patent: November 13, 2012Assignee: Arkema FranceInventors: Anne Pigamo, Dominique Deur-Bert, Laurent Wendlinger
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Publication number: 20120283490Abstract: 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: ApplicationFiled: April 12, 2012Publication date: November 8, 2012Applicant: SIEMENS MEDICAL SOLUTIONS USA, INC.Inventors: Umesh B. Gangadharmath, Joseph C. Walsh, Hartmuth C. Kolb, Ricardo Rodriguez, Arkadij M. Elizarov, Carroll Edward Ball
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Patent number: 8299309Abstract: 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: GrantFiled: October 11, 2011Date of Patent: October 30, 2012Assignee: E I du Pont de Nemours and CompanyInventors: Mario Joseph Nappa, Xuehui Sun, Lev Moiseevich Yagupolskii, Andrey Anatolievich Filatov, Vladimir Nikolaevich Boiko, Yurii Lvovich Yagupolskii
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Publication number: 20120215039Abstract: 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: ApplicationFiled: January 23, 2012Publication date: August 23, 2012Applicant: HONEYWELL INTERNATIONAL INC.Inventors: RYAN HULSE, HANG T. PHAM, HSUEH SUNG TUNG, KONSTANTIN POKROVSKI, DANIEL C. MERKEL
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Publication number: 20120184785Abstract: 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: ApplicationFiled: December 7, 2011Publication date: July 19, 2012Inventors: Stephen A. Cottrell, Yuon Chiu, Haluk Kopkalli, Hsueh Sung Tung, Kevin D. Uhrich, Peter Scheidle
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Publication number: 20120178977Abstract: 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: ApplicationFiled: December 7, 2011Publication date: July 12, 2012Inventors: Daniel C. Merkel, Hsueh Sung Tung, Konstantin A. Pokrovski, Haiyou Wang, Selma Bektesevic
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Patent number: 8212091Abstract: 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: GrantFiled: November 24, 2006Date of Patent: July 3, 2012Assignee: The South African Nuclear Energy Corporation LimitedInventors: Izak Jacobus Van Der Walt, Alfred Teo Grunenberg, Johannes Theodorus Nel
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Publication number: 20120138841Abstract: 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: ApplicationFiled: October 5, 2011Publication date: June 7, 2012Inventors: Ryan Hulse, Hang T. Pham
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Publication number: 20120108859Abstract: 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: ApplicationFiled: October 20, 2011Publication date: May 3, 2012Applicant: E. I. DU PONT DE NEMOURS AND COMPANYInventors: MARIO JOSEPH NAPPA, Ekaterina N. Swearingen, Allen Capron Sievert, Xuehui Sun
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Patent number: 8158836Abstract: 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: GrantFiled: December 23, 2010Date of Patent: April 17, 2012Assignee: Arkema FranceInventors: Anne Pigamo, Dominique Deur-Bert, Laurent Wendlinger
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Publication number: 20120022300Abstract: 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: ApplicationFiled: September 30, 2011Publication date: January 26, 2012Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Robert Johnson, Hsueh Sung Harry Tung
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Publication number: 20110319677Abstract: 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: ApplicationFiled: June 23, 2011Publication date: December 29, 2011Applicant: Asahi Glass Company, LimitedInventors: Satoshi KAWAGUCHI, Hidekazu Okamoto, Yu Takeuchi, Hirokazu Takagi, Kunio Watanabe, Koichi Yanase
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Publication number: 20110319674Abstract: 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: ApplicationFiled: June 24, 2010Publication date: December 29, 2011Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Haiyou Wang, Hsueh Sung Tung
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Publication number: 20110319676Abstract: 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: ApplicationFiled: June 23, 2011Publication date: December 29, 2011Applicant: ASAHI GLASS COMPANY, LIMITEDInventors: Hirokazu TAKAGI, Hidekazu Okamoto, Satoshi Kawaguchi, Yu Takeuchi, Kunio Watanabe, Koichi Yanase, Shingo Nomura
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Patent number: 8076521Abstract: 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: GrantFiled: June 26, 2008Date of Patent: December 13, 2011Assignee: Arkema Inc.Inventors: Maher Y. Elsheikh, Philippe Bonnet, Benjamin Bin Chen
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Patent number: 8071825Abstract: 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: GrantFiled: August 1, 2008Date of Patent: December 6, 2011Assignee: Honeywell International Inc.Inventors: Robert C. Johnson, Hsueh S. Tung, Daniel C. Merkel
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Patent number: 8058488Abstract: 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: GrantFiled: November 20, 2008Date of Patent: November 15, 2011Assignee: E. I. du Pont de Nemours and CompanyInventors: Mario Joseph Nappa, Xuehui Sun, Lev Moiseevich Yagupolskii, Andrey Anatolievich Filatov, Vladimir Nikolaevich Boiko, Yurii Lvovich Yagupolskii
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Publication number: 20110269999Abstract: 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: ApplicationFiled: April 29, 2010Publication date: November 3, 2011Applicant: HONEYWELL INTERNATIONAL INC.Inventors: George R. Cook, Haluk Kopkalli, Stephen A. Cottrell, Yuon Chiu, Peter Scheidle, Daniel C. Merkel
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Publication number: 20110172471Abstract: 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: ApplicationFiled: March 22, 2011Publication date: July 14, 2011Applicant: PACIFITECH PTY LIMITEDInventors: Eric Miles Kennedy, Bogdan Zygmunt Dlugogorski
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Publication number: 20110160497Abstract: 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: ApplicationFiled: December 23, 2010Publication date: June 30, 2011Applicant: Arkema FranceInventors: Dominique Deur-Bert, Laurent Wendlinger, Anne Pigamo
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Publication number: 20110124928Abstract: 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: ApplicationFiled: January 12, 2011Publication date: May 26, 2011Applicant: Zeon CorporationInventors: Tadahiro Ohmi, Yasuyuki Shirai, Takeyoshi Kato, Kimiaki Tanaka, Masahiro Nakamura, Katsutomo Tanaka
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Publication number: 20110124929Abstract: 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: ApplicationFiled: June 25, 2009Publication date: May 26, 2011Inventors: Masatoshi Nose, Akinari Sugiyama, Atsushi Suzuki
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Publication number: 20110118513Abstract: 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: ApplicationFiled: April 9, 2009Publication date: May 19, 2011Applicant: INEOS FLUOR HOLDINGS LIMITEDInventors: John W. Smith, Claire McGuiness, Andrew P. Sharratt
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Publication number: 20110112338Abstract: 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: ApplicationFiled: May 15, 2009Publication date: May 12, 2011Applicant: MEXICHEM/ AMANCO HOLDING S.A. DE C.V.Inventors: John W. Smith, Claire McGuiness, Andrew P. Sharratt, Andrew M. Taylor
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Publication number: 20110060170Abstract: 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: ApplicationFiled: July 13, 2009Publication date: March 10, 2011Applicant: ZEON CORPORATIONInventors: Tatsuya Sugimoto, Takefumi Suzuki, Jo Konagawa
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Publication number: 20110028769Abstract: 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: ApplicationFiled: March 18, 2009Publication date: February 3, 2011Applicant: E.I. Du Pont De Nemours and CompanyInventors: Xuehui Sun, Mario Joseph Nappa, Win-Chung Lee
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Patent number: 7829748Abstract: 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: GrantFiled: September 21, 2009Date of Patent: November 9, 2010Assignee: Honeywell International Inc.Inventors: Hsuehsung Tung, Robert C. Johnson, Daniel C. Merkel, Haiyou Wang
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Publication number: 20100210883Abstract: 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: ApplicationFiled: February 8, 2010Publication date: August 19, 2010Applicant: 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
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Publication number: 20100145110Abstract: 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: ApplicationFiled: September 14, 2009Publication date: June 10, 2010Applicant: Pacifitech PTY LimitedInventors: Eric Miles Kennedy, Bogdan Zygmunt Dlugogorski
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Publication number: 20100121117Abstract: 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: ApplicationFiled: February 19, 2009Publication date: May 13, 2010Applicant: FOOSUNG Co. Ltd.Inventors: Hyang Ja JANG, Jong Yool Yang, Chul Ho Kim, Young Gu Cho, Jung Eun Lee
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Publication number: 20100121115Abstract: 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: ApplicationFiled: September 5, 2007Publication date: May 13, 2010Applicant: E. I. DU PONT DE NEMOURS AND COMPANYInventors: Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert, Mario Joseph Nappa
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Patent number: 7700815Abstract: 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: GrantFiled: September 28, 2007Date of Patent: April 20, 2010Assignee: Honeywell International IncInventors: Hsueh Sung Tung, Rajiv R. Singh, Michael Van Der Puy
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Patent number: 7592494Abstract: 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: GrantFiled: July 25, 2003Date of Patent: September 22, 2009Assignee: Honeywell International Inc.Inventors: Hsueh Sung Tung, Robert C. Johnson, Daniel C. Merkel
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Publication number: 20090209791Abstract: 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: ApplicationFiled: February 19, 2009Publication date: August 20, 2009Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Michael Van Der Puy, George R. Cook, Peter H. Sheidle, Kevin D. Uhrich, Haiyou Wang, Hsueh Sung Tung
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Publication number: 20090069589Abstract: Methods and systems for producing hydrohalocarbon and/or halocarbon compounds with an inorganic fluoride (e.g., silicon tetrafluoride (SiF4)) are disclosed herein.Type: ApplicationFiled: September 3, 2008Publication date: March 12, 2009Applicant: International Isotopes Inc.Inventor: Bamidele Omotowa
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Publication number: 20090036719Abstract: 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: ApplicationFiled: August 25, 2008Publication date: February 5, 2009Applicant: Pacifitech PTY LimitedInventors: Eric Miles Kennedy, Bogdan Zygmunt Dlugogorski
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Publication number: 20090012335Abstract: 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: ApplicationFiled: June 27, 2008Publication date: January 8, 2009Applicant: E.I.du pont de Nemours and CompanyInventors: Mario Joseph Nappa, Ekaterina N. Swearingen
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Patent number: 7473810Abstract: 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: GrantFiled: October 12, 2007Date of Patent: January 6, 2009Assignee: Honeywell International Inc.Inventors: Michael Van Der Puy, Jingji Ma
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Patent number: 7439408Abstract: 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: GrantFiled: April 13, 2006Date of Patent: October 21, 2008Assignee: Bayer Cropscience AGInventor: Alexander Straub
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Publication number: 20080242901Abstract: 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: ApplicationFiled: June 6, 2008Publication date: October 2, 2008Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Sudip Mukhopadhyay, Hsueh Sung Tung, Haridasan K. Nair, Jingji Ma