Utilizing Unsaturated Compound Patents (Class 570/175)
-
Publication number: 20110087056Abstract: The present invention provides adiabatic plug flow reactors suitable for the production of chlorinated and/or fluorinated propene and higher alkenes from the reaction of chlorinated and/or fluorinated alkanes and chlorinated and/or fluorinated alkenes. The reactors comprise one or more designs that minimize the production of by-products at a desired conversion.Type: ApplicationFiled: October 8, 2010Publication date: April 14, 2011Applicant: DOW GLOBAL TECHNOLOGIESInventors: Max M. Tirtowidjojo, Hua Bai, Debashis Chakraborty, Juergen Eiffler, Heinz Groenewald, Kurt F. Hirsekorn, Manfred Kokott, William J. Kruper, JR., Thomas U. Luebbe, Thomas J. Parsons, Avani Maulik Patel, Marcus Wobser
-
Patent number: 7902410Abstract: A process for the production of fluorinated alkanes by contacting a feed stream containing a fluorinated olefin and a reducing agent, preferably with a first amount of catalyst to produce a fluorinated alkane, at a first conversion level, wherein a first effluent stream contains unreacted fluorinated olefin and reducing agent; and contacting the first effluent stream under conditions effective to produce a higher level of conversion than said conversion level.Type: GrantFiled: October 27, 2006Date of Patent: March 8, 2011Assignee: Honeywell International Inc.Inventors: Michael Van Der Puy, George R. Cook, Peter H. Scheidle, Kevin D. Uhrich
-
Publication number: 20110054226Abstract: Disclosed is a process and apparatus for the catalytic hydrogenation of fluoroolefins to fluorocarbons where the reaction is carried out in a multi-tube shell and tube reactor. Reactions involving hydrogenation of fluoro-olefins are typically exothermic. In commercial processes where a fluoro-olefin C(n)H(2n?x)F(x) to C(n)H(2n?x|2)F(x) is hydrogenated (e.g. hexafluoropropylene to 236ea, 1225ye to 245eb, and the like), inadequate management or control of heat removal may induce excess hydrogenation, decomposition and hot spots resulting in reduced yields and potential safety issues. In the hydrogenation of fluoro-olefins, it is therefore necessary to control the reaction temperature as precisely as practical to overcome challenges associated with heat management and safety.Type: ApplicationFiled: August 31, 2009Publication date: March 3, 2011Inventors: Haluk Kopkalli, Yuon Chiu, Orlando George Rodrigues, Gus Cerri, Hsueh Sung Tung, Stephen A. Cottrell
-
Patent number: 7786333Abstract: 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: GrantFiled: February 19, 2009Date of Patent: August 31, 2010Assignee: Honeywell International, Inc.Inventors: Michael Van Der Puy, George R. Cook, Peter H. Sheidle, Kevin D. Uhrich, Haiyou Wang, Hsueh Sung Tung
-
Patent number: 7759532Abstract: The present invention relates to compositions and processes of using perfluoropolyether to maintain or improve the oil return, lubrication, cooling capacity, or energy efficiency of a refrigeration, air conditioning or heat transfer system.Type: GrantFiled: July 11, 2007Date of Patent: July 20, 2010Assignee: E.I. du Pont de Nemours and CompanyInventors: Thomas J. Leck, Thomas Frank Saturno, Gregory A. Bell
-
Publication number: 20100137658Abstract: Provided is a process for making 2-chloro-1,1,1,2-tetrafluoropropane. The process has the step of hydrofluorinating 2-chloro-3,3,3-trifluoropropene in the presence of a catalyst selected from the group consisting of SbCl3, SbCl5, SbF5, TiCl4, SnCl4, Cr2O3, and fluorinated Cr2O3.Type: ApplicationFiled: December 4, 2009Publication date: June 3, 2010Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Daniel C. Merkel, Robert C. Johnson, Hsueh Sung Tung
-
Patent number: 7678949Abstract: A process for the manufacture of CF3CH?CHF and/or CF3CF?CH2 is disclosed. The process involves (a) reacting HF and chlorine and at least one halopropene of the formula CX3CCI?CCIX (where each X is independently F or Cl) to produce a product including both CF3CCI2CCIF2 and CF3CCIFCCI2F; (b) reacting CF3CCI2CCIF2 and CF3CCIFCCI2F produced in (a) with hydrogen to produce a product including both CF3CH2CHF2 and CF3CHFCH2F; (c) dehydrofluorinating CF3CH2CHF2 and CF3CHFCH2F produced in (b) to produce a product including both CF3CH?CHF and CF3CF?CH2; and (d) recovering CF3CH?CHF and/or CF3CF?CH2 from the product produced in (c). In (a), both CF3CCI2CCIF2 and CF3CCIFCCI2F are produced in the presence of a chlorofluorination catalyst consisting of (i) compositions comprising a crystalline alpha-chromium oxide where at least 0.05 atom % of the chromium atoms in the alpha-chromium oxide lattice are replaced by copper, and (ii) compositions of (i) which have been treated with a fluorinating agent.Type: GrantFiled: August 4, 2006Date of Patent: March 16, 2010Assignee: E.I. du Pont de Nemours and CompanyInventors: Velliyur Nott Mallikarjuna Rao, H. David Rosenfeld, Allen Capron Sievert, Shekhar Subramoney
-
Patent number: 7663007Abstract: A process for the manufacture of CF3CH?CHF and/or CF3CH?CF2 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 CI) 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; (c) dehydrofluorinating CF3CH2CHF2 and/or CF3CH2CF3 produced in (b) to produce a product comprising CF3CH?CHF and/or CF3CH?CF2; and (d) recovering CF3CH?CHF and/or CF3CH?CF2 from the product produced in (c). 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.Type: GrantFiled: August 4, 2006Date of Patent: February 16, 2010Assignee: E.I. du Pont de Nemours and CompanyInventors: Velliyur Nott Mallikarjuna Rao, H. David Rosenfeld, Allen Capron Sievert, Shekhar Subramoney
-
Publication number: 20090227821Abstract: The present invention provides a novel method for preparing 4,4,4-trifluorobutane-2-one by providing a fluorobutene selected from the group consisting of 2,4,4,4-tetrafluoro-1-butene, (E)-1,1,1,3-tetrafluoro-2-butene, (Z)-1,1,1,3-tetrafluoro-2-butene, and mixture thereof; and reacting the fluorobutene(s) with a proton acid and water.Type: ApplicationFiled: October 18, 2004Publication date: September 10, 2009Applicant: CENTRAL GLASS CO., LTD.Inventors: Adam Alty, Frank Waters, Richard Du Boisson, Yokusu Kuriyama, Masamichi Maruta
-
Publication number: 20090216054Abstract: Disclosed is a process for producing 1,2,3,4-tetrachlorohexafluorobutane safely in a high yield in the industrial viewpoint and at low cost in the economical viewpoint. Specifically disclosed is a process for producing 1,2,3,4-tetrachlorohexafluorobutane which process comprises: (1) a step of chlorinating 1,3-butadiene, thereby preparing a mixture containing 1,2,3,4-tetrachlorobutane, and (2) a step of allowing the 1,2,3,4-tetrachlorobutane prepared in the step (1) to react with a fluorine gas in the presence of a diluting gas in a gas phase, thereby preparing a mixture containing 1,2,3,4-tetrachlorohexafluorobutane.Type: ApplicationFiled: April 25, 2007Publication date: August 27, 2009Applicant: SHOWA DENKO K.K.Inventors: Hiromoto Ohno, Toshio Ohi
-
Patent number: 7566809Abstract: Process for the separation of a mixture comprising at least one hydrofluoroalkane and hydrogen fluoride, according to which a hydrofluoroalkane/hydrogen fluoride mixture is reacted with at least one chlorinated or chlorofluorinated precursor of the hydrofluoroalkane. Process for the preparation of a hydrofluoroalkane comprising such a separation, in combination with a catalytic reaction stage. Azeotropic compositions.Type: GrantFiled: May 25, 2007Date of Patent: July 28, 2009Assignee: Solvay S.A.Inventors: Alain Lambert, Vincent Wilmet
-
Publication number: 20090131727Abstract: A process for producing hydrofluorocarbon compounds represented by the following formula: CF3CHFCHm+1Fn wherein m is 0 or 2; n is 0 or 2; and m+n=2. The process has the step of contacting, i.e., reacting, hydrogen with a precursor compound represented by the following formula: CF3CF?CHmFn wherein m is 0 or 2; n is 0 or 2; and m+n=2. The contact is carried out in the presence of a solid catalyst and in the presence or absence of an inert gas. The catalyst is selected from the group consisting of: Fe, Co, Ni, Cu, Cr, Ru, Rh, Ag, Re, Os, Ir, Pt, Au, Sn, and any combinations thereof. For the hydrogenation of 1234yf to 254eb, Pd can also be used as catalyst in addition to the other above-referenced metals. These metals are preferably supported on a carrier such as activated carbon.Type: ApplicationFiled: November 4, 2008Publication date: May 21, 2009Inventors: Shuwu Yang, Hsueh Sung Tung
-
Publication number: 20080269532Abstract: Disclosed is a method for the synthesis of fluorinated alkenes comprising contacting a fluorinated alkyne of the formula R1 C?C R2, wherein R1 and R2 are independently selected from CF3, C2F5, C3F7, and C4F9, in a pressure vessel, with a Lindlar catalyst, with substantially one molar equivalent of hydrogen, to make the corresponding cis-alkene of formula R1 C?C R2 with high selectivity, wherein said hydrogen is added in portions over a period of time, so as to produce an initial pressure in the pressure in the vessel of no more than about 100 psi.Type: ApplicationFiled: April 28, 2008Publication date: October 30, 2008Applicant: E. I. DU PONT DE NEMOURS AND COMPANYInventor: Ekaterina N. SWEARINGEN
-
Publication number: 20080207963Abstract: A method for preparing a catalyst composition suitable for increasing the fluorine content in a hydrocarbon or a halogenated hydrocarbon is disclosed. The method involves (a) co-precipitating a solid by adding ammonium hydroxide to an aqueous solution of a soluble trivalent chromium salt and a soluble salt of a modifier metal selected from silver and palladium, that contains at least three moles of nitrate (i.e., NO3?) per mole of chromium (i.e., Cr+3) in the solution and has a modifier metal concentration of from about 0.05 atom % to about 10 atom % of the total concentration of modifier metal and chromium in the solution to form an aqueous mixture containing co-precipitated solid and dissolved ammonium nitrate; and after at least three moles of ammonium hydroxide per mole of chromium in the solution has been added to the solution, (b) drying said aqueous mixture formed in (a); and (c) calcining the dried solid formed in (b) in an atmosphere containing at least 10% oxygen by volume (e.g., air).Type: ApplicationFiled: February 21, 2008Publication date: August 28, 2008Inventors: Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
-
Publication number: 20080191163Abstract: Disclosed herein are laser cutting/etching assist fluids and methods of use thereof. The compounds include unsaturated fluorocarbons appropriate for use in laser assist applications.Type: ApplicationFiled: February 5, 2008Publication date: August 14, 2008Inventor: Michael T. Mocella
-
Patent number: 7348461Abstract: 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: GrantFiled: October 31, 2003Date of Patent: March 25, 2008Assignee: Great Lakes Chemical CorporationInventors: Yuichi Iikubo, Stephen Owens, Mitchel Cohn, Stephan M. Brandstadter, Vicki E. Hedrick, Janet K. Boggs, John Qian, Julie Sacarias
-
Patent number: 7345209Abstract: 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: GrantFiled: April 29, 2005Date of Patent: March 18, 2008Assignee: Honeywell International Inc.Inventors: Sudip Mukhopadhyay, Haridasan K. Nair, Hsueh S. Tung, Michael Van Der Puy
-
Patent number: 7285691Abstract: A process is disclosed for the manufacture of 1,1,1,3,3,3-hexafluoropropane (HFC-236fa) and at least one 1,1,1,2,3,3-hexafluoropropane (HFC-236ea) and 1,1,1,2,3,3,3-heptafluoropropane (HFC-227ea). The process involves (a) reacting HF, Cl2, and at least one halopropene of the formula CX3CCl=CX2 (where each X is independently F or Cl) to produce a product including both CF3CCl2CF3 and CF3CClFCClF2; (b) reacting CF3CCl2CF3 and CF3CClFCClF2 produced in (a) with hydrogen to produce a product comprising CF3CH2CF3 and at least one compound selected from the group consisting of CHF2CHFCF3, and CF3CHFCF3; and (c) recovering from the product produced in (b), CF3CH2CF3 and at least one compound selected from the group consisting of CHF2CHFCF3 and CF3CHFCF3.Type: GrantFiled: October 13, 2004Date of Patent: October 23, 2007Assignee: E.I. du Pont de Nemours and CompanyInventors: Velliyur Nott Mallikarjuna Rao, Allen C. Sievert
-
Patent number: 7285690Abstract: A process for the manufacture of CF3CH2CHF2 and 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 CI) to produce a product including both CF3CCI=CF2 and CF3CHCICF3; (b) reacting CF3CCI=CF2 and CF3CHCICF3 produced in (a) with hydrogen to produce a product including both CF3CH2CHF2 and CF3CH2CF3; and (c) recovering CF3CH2CHF2 and CF3CH2CF3 from the product produced in (b). In (a), the CF3CCI=CF2 and CF3CHCICF3 are produced in the presence of a fluorination catalyst including a ZnCr2O4/crystalline ?-chromium oxide composition, a ZnCr2O4/crystalline ?-chromium oxide composition which has been treated with a fluorinating agent, a zinc halide/?-chromium oxide composition and/or a zinc halide/?-chromium oxide composition which has been treated with a fluorinating agent.Type: GrantFiled: October 13, 2004Date of Patent: October 23, 2007Assignee: E.I. du Pont de Nemours and CompanyInventors: Velliyur Nott Mallikarjuna Rao, Allen C. Sievert
-
Patent number: 7285692Abstract: A process is disclosed for the manufacture of CF3CH2CHF2 and CF3CHFCH2F. The process involves (a) reacting hydrogen fluoride, chlorine, and at least one halopropene of the formula CX3CCl?CClX (where each X is independently F or Cl) to produce a product including both CF3CCl2CClF2 and CF3CClFCCl2F; (b) reacting CF3CCl2CClF2 and CF3CClFCCl2F produced in (a) with hydrogen to produce a product including both CF3CH2CHF2, and CF3CHFCH2F; and (c) recovering CF3CH2CHF2 and CF3CHFCH2F from the product produced in (b). In (a), the CF3CCl2CClF2 and CF3CClFCCl2F are produced in the presence of a chlorofluorination catalyst including a ZnCr2O4/crystalline ?-chromium oxide composition, a ZnCr2O4/crystalline ?-chromium oxide composition which has been treated with a fluorinating agent, a zinc halide/?-chromium oxide composition and/or a zinc halide/?-chromuim oxide composition which has been treated with a fluorinating agent.Type: GrantFiled: October 13, 2004Date of Patent: October 23, 2007Assignee: E.I. du Pont de Nemours and CompanyInventors: Velliyur Nott Mallikarjuna Rao, Allen C. Sievert
-
Patent number: 7223892Abstract: Process for the separation of a mixture comprising at least one hydrofluoroalkane and hydrogen fluoride, according to which a hydrofluoroalkane/hydrogen fluoride mixture is reacted with at least one chlorinated or chlorofluorinated precursor of the hydrofluoroalkane. Process for the preparation of a hydrofluoroalkane comprising such a separation, in combination with a catalytic reaction stage. Azeotropic compositions.Type: GrantFiled: June 28, 2006Date of Patent: May 29, 2007Assignee: Solvay S.A.Inventors: Alain Lambert, Vincent Wilmet
-
Patent number: 7145046Abstract: Inorganic and organic compounds containing fluorine can be produced, for example, from corresponding chlorine-containing compounds by chlorine/fluorine exchange using fluorinating agents. Monocyclic or bicyclic compounds containing at least two nitrogen atoms, at least one of which is incorporated into the ring system, can be used as catalysts or fluorinating agents for chlorine/fluorine exchange reactions to produce sulfurylchlorofluoride, sulfurylfluoride or a carboxylic acid fluoride. It is likewise possible to carry out HF addition to unsaturated carbon-carbon bonds or chlorine/fluorine exchange at carbon atoms. For example, monochloro or dichloro malonic acid esters can be converted to difluoro malonic acid esters. Work-up of the reaction mixture can be simplified by using suitable solvents which force the reaction mixture to exist in two phases.Type: GrantFiled: August 1, 2003Date of Patent: December 5, 2006Assignee: Solvay Fluor und Derivate GmbHInventors: Max Braun, Carsten Brosch
-
Patent number: 7094936Abstract: Methods and materials are provided for the production and purification of halogenated compounds and intermediates in the production of 1,1,1,3,3-pentafluoropropane. In a preferred embodiment, the process steps include: (1) reacting carbon tetrachloride with vinyl chloride to produce 1,1,1,3,3-pentachloropropane; (2) dehydrochlorinating the 1,1,1,3,3-pentachloropropane with a Lewis acid catalyst to produce 1,1,3,3-tetrachloropropene; (3) fluorinating the 1,1,3,3-tetrachloropropene to produce 1-chloro-3,3,3-trifluoropropene; (4) fluorinating the 1-chloro-3,3,3-trifluoropropene to produce a product mixture containing 1,1,1,3,3-pentafluoropropane; and (5) separating 1,1,1,3,3-pentafluoropropane from by-products.Type: GrantFiled: October 16, 2003Date of Patent: August 22, 2006Assignee: Great Lakes Chemical CorporationInventors: Stephen Owens, Andrew Jackson, Vimal Sharma, Mitchel Cohn, John Cheng-Ping Qian, Julia Ann Sacarias, Yuichi Iikubo
-
Patent number: 7067707Abstract: Process for the manufacture of pentafluoroethane, according to which tetrafluoroethylene is subjected to reaction with an organic nitrogenous base hydrofluoride at a temperature of greater than 100° C. and not exceeding 160° C.Type: GrantFiled: August 22, 2003Date of Patent: June 27, 2006Assignee: Solvay (Societe Anonyme)Inventors: Eberhard Piepho, Vincent Wilmet, Olivier Buyle
-
Patent number: 7053253Abstract: Perfluoro-4-methyl-2-pentene containing the undesirable perfluoro-2-methyl-2-pentene may be purified by contacting the mixture with at least a stoichiometric equivalent of an aqueous inorganic base (relative to the perfluoro-2-methyl-2-pentene), in the presence of a polar solvent.Type: GrantFiled: May 2, 2005Date of Patent: May 30, 2006Assignee: 3M Innovative Properties CompanyInventors: Zhongxing Zhang, Zai-Ming Qiu
-
Patent number: 7041859Abstract: A method for obtaining a halogenated organic compound, whereby an organotrifluoroborate compound is reacted with a halide ion in the presence of an oxidizing agent to produce the corresponding halogenated organic compound. The method may be used for producing radiohalogenated organic compounds.Type: GrantFiled: July 5, 2005Date of Patent: May 9, 2006Assignee: University of Tennessee Research FoundationInventor: George W. Kabalka
-
Patent number: 7038095Abstract: A mixture of fluoroalkyl iodide telomers represented by the formula: Rf(CF2CF2)nI wherein Rf represents a fluoroalkyl group whose number of carbon atoms is in the range of 1 to 10, with the polymerization degree n equal to or more than k that is an integer of 3 or more, is obtained by reacting a fluoroalkyl iodide with tetrafluoroethylene in a first reactor followed by fractionating a first reaction mixture which contains fluoroalkyl iodide telomers of low polymerization degree, as well as by reacting the telomer with n of (k?1) separated from the first reaction mixture with tetrafluoroethylene in the second reactor.Type: GrantFiled: February 5, 2002Date of Patent: May 2, 2006Assignee: Daikin Industries, Ltd.Inventors: Yukio Homoto, Kunitada Tanaka
-
Patent number: 6992229Abstract: The present invention has an object to provide a method for purifying a fluorinated hydroxyl compound of the formula 1 safely in a high yield under industrially practical conditions. Namely, a mixture containing a fluorinated hydroxyl compound of Rf—CR1R2—OH (Formula 1, wherein Rf is a C1-20 polyfluoroalkyl group, and each of R1 and R2 is a hydrogen atom or a C1-3 alkyl group) such as 2,2,3,3-tetrafluoropropanol, and a compound having an unshared electron pair, is distilled by heating in the presence of a solid acid catalyst such as a cation exchange resin catalyst, or by adding a proton source such as water.Type: GrantFiled: November 19, 2002Date of Patent: January 31, 2006Assignee: Asahi Glass Company, LimitedInventors: Hidekazu Okamoto, Akihiro Wada, Toshihiko Toma, Nobuyuki Yamagishi
-
Patent number: 6958422Abstract: The present invention relates to the pyrolysis of hydrochlorofluorocarbons to form fluoromonomers such as tetrafluoroethylene, the pyrolysis being carried out in a reaction zone lined with nickel and mechanically supported by a jacket of other corrosion resistant metal, the nickel lining providing an improved yield of valuable reaction products.Type: GrantFiled: December 17, 2003Date of Patent: October 25, 2005Assignee: E. I. du Pont de Nemours and CompanyInventors: Charles Joseph Noelke, Velliyur Nott Mallikarjuna Rao
-
Patent number: 6946582Abstract: The present invention provides a process for producing a fluoroalkyl iodide represented by the general formula (II): Rf-CH2CH2I??(II) wherein Rf is a perfluoroalkyl or polyfluoroalkyl group comprising 1 to 20 carbons, the process comprising reacting hydrogen iodide gas with a fluoroalkene in the presence of a catalyst. The present invention also provides a process for producing a fluoroester by reacting the fluoroalkyl iodide with a carboxylate.Type: GrantFiled: November 20, 2002Date of Patent: September 20, 2005Assignee: Daikin Industries, Ltd.Inventors: Toshiyuki Katsube, Kouzou Noda, Jun Miki
-
Patent number: 6924403Abstract: The present invention relates to the process of pyrolyzing tetrafluoroethylene to hexafluoropropylene by carrying out the pyrolysis in a tubular reactor that is lined with either nickel or nickel alloy which contains no greater than 8 wt % chromium.Type: GrantFiled: May 7, 2003Date of Patent: August 2, 2005Assignee: E. I. du Pont de Nemours and CompanyInventors: John James Barnes, Kenneth Paul Kelch, Thomas D. Sandbrook, David John Van Bramer
-
Patent number: 6919490Abstract: The present invention relates to a process for continuously producing a perfluoroalkyl iodide represented by the general formula Rf(CF2CF2)nI, wherein Rf is a C1-6 perfluoroalkyl and n is an integer from 1 to 4, the method comprising continuously supplying a perfluoroalkyl iodide as a telogen represented by the general formula RfI, wherein Rf is as defined above, and tetrafluoroethylene as a taxogen to a tubular reactor packed with a metal catalyst comprising a powdery spherical metal or a sintered metal; and conducting telomerization at a temperature of 60 to 160° C. under a pressure of 0.1 to 5 MPa (gauge pressure). According to the present invention, medium-chain perfluoroalkyl iodides can be continuously and efficiently produced with little generation of impurities, such as hydrogen-containing organic compounds and the like.Type: GrantFiled: April 17, 2002Date of Patent: July 19, 2005Assignee: Daikin Industries, Ltd.Inventors: Yoshio Funakoshi, Jun Miki
-
Patent number: 6897344Abstract: Divalent and trivalent metal salts are added to the solution containing the fluorine compound to precipitate the layered double hydroxide containing the fluorine compound between layers. By these processes, the fluorine compound can be fixed with high rate. Moreover, if necessary, the precipitated layered double hydroxide can be recovered to separate the fluorine compound or its salt between layers. Therefore, the burden to environment or the ecosystem by the fluorine compound can be reduced.Type: GrantFiled: July 26, 2001Date of Patent: May 24, 2005Assignee: Jemco Inc.Inventors: Kiyoshi Fuda, Toshiaki Matsunaga, Takeshi Kamiya, Kota Omori
-
Patent number: 6872861Abstract: The invention relates to a process for preparing polyfluoroalkyl-lithium compounds by deprotonation of polyfluoroalkyl compounds by means of lithium bases.Type: GrantFiled: June 7, 2002Date of Patent: March 29, 2005Assignee: Bayer AktiengesellschaftInventors: Marielouise Schneider, Albrecht Marhold, Alexander Kolomeitsev, Alexander Kadyrov, Gerd-Volker Röschenthaler, Jan Barten
-
Patent number: 6861565Abstract: A process for producing a fluoroalkanol which can easily be industrially practiced with high selectivity, is provided. CHR1R2OH, a radical initiator and CF2?CFRf are continuously supplied and reacted at from 105 to 135° C., and H—(RfCFCF2)n—CR1R2—OH formed, is continuously discharged. Here, each of R1 and R2 is a hydrogen atom or a C1-3 alkyl group, Rf is a fluorine atom or a C1-4 polyfluoroalkyl group, and n is an integer of from 1 to 4.Type: GrantFiled: March 10, 2003Date of Patent: March 1, 2005Assignee: Asahi Glass Company, LimitedInventors: Toshihiko Tohma, Akihiro Wada
-
Patent number: 6858763Abstract: The present invention relates to a process for preparing an elastomeric ethylene-hexafluoropropylene copolymer with excellent vulcanization properties, which comprises emulsion polymerizing ethylene, hexafluoropropylene and when in demand, a monomer copolymerizable therewith in a aqueous medium at a low temperature of ?20° C. to 40° C. using a radical polymerization initiator.Type: GrantFiled: September 19, 2001Date of Patent: February 22, 2005Assignee: Daikin Industries, Ltd.Inventors: Mitsuo Tsukamoto, Masao Otsuka, Mitsuhiro Otani, Tatsuya Morikawa, Hideya Saito
-
Patent number: 6774270Abstract: A method of removing hexafluoropropylene dimers (“HFP dimers”), dimer hydrides and other oligomers from a fluid is described. The method comprises heating the fluid to isomerize the HFP dimers to the thermodynamic isomer, and contacting the fluid with a tertiary amine (or salts thereof) to form a hexafluoropropylene dimer—tertiary amine adduct. The method may further comprise the step of separating the dimer adducts from the reaction mixture.Type: GrantFiled: April 1, 2003Date of Patent: August 10, 2004Assignee: 3M Innovative Properties CompanyInventors: Zhongxing Zhang, Zai-Ming Qiu, Daniel R. Vitcak, Richard M. Flynn
-
Patent number: 6747178Abstract: According to the present invention there is provided a method of carrying out a chemical reaction between at least two fluids, the method comprising providing respective flow paths for the at least two fluids, said flow paths communicating with each other in a region in which the at least two fluids may contact each other, and flowing the at least two fluids along said flow paths such that in said region the at least two fluids contact each other and a chemical reaction occurs between them, said region having a width perpendicular to the direction of flow in the range 10-10,000 micrometers. It has been found that using a so-called “microreactor”, that is a reactor having dimensions perpendicular to the flow direction of less than 10,000 micrometers, according to the present method, improved control over a fluid chemical reaction can be achieved, which can result in significant improvements in reaction product yield and/or purity, as well as other benefits.Type: GrantFiled: October 2, 2000Date of Patent: June 8, 2004Assignee: British Nuclear Fuels plcInventors: Paul Harston, Malcolm John Atherton, Robert G. Holmes, Richard Dickinson Chambers, Robert Spink
-
Patent number: 6743957Abstract: Divalent and trivalent metal salts are added to the solution containing the fluorine compound and the polymer containing fluorine to precipitate the layered double hydroxide containing the fluorine compound between layers. At this time, the polymer containing fluorine suspended in the solution is also coagulated to precipitate. By these processes, the fluorine compound is fixed with high rate to separate from the solution with the polymer containing fluorine, and recovered if necessary. By this treatment process, the fluorine compound and the polymer containing fluorine, contained in the wastewater etc. can be separated easily, and the burden to environment or ecosystem can be reduced.Type: GrantFiled: June 26, 2002Date of Patent: June 1, 2004Assignee: JEMCO, Inc.Inventors: Kiyoshi Fuda, Toshiaki Matsunaga, Takeshi Na Kamiya, Kota Omori
-
Patent number: 6720464Abstract: Octafluoropropane is produced by a process comprising a step (1) of reacting hexafluoropropene with hydrogen fluoride in a gas phase at a temperature of from 150 to 450° C. in the presence of a fluorination catalyst to obtain 2H-heptafluoropropane and a step (2) of reacting 2H-heptafluoropropane obtained in step (1) with fluorine gas in a gas phase at a temperature of from 250 to 500° C. in the absence of a catalyst to obtain octafluoropropane. High-purity octafluoropropane is obtained which can be used in a process for producing a semiconductor device.Type: GrantFiled: April 29, 2002Date of Patent: April 13, 2004Assignee: Showa Denko K.K.Inventors: Hiromoto Ohno, Toshio Ohi
-
Publication number: 20030208090Abstract: A liquid phase process is disclosed for producing halogenated alkane adducts of the formula CAR1R2CBR3R4 (where A, B, R1, R2, R3, and R4 are as defined in the specification) which involves contacting a corresponding halogenated alkane, AB, with a corresponding olefin, CR1R2═CR3R4 in a dinitrile or cyclic carbonate ester solvent which divides the reaction mixture into two liquid phases and in the presence of a catalyst system containing (i) at least one catalyst selected from monovalent and divalent copper; and optionally (ii) a promoter selected from aromatic or aliphatic heterocyclic compounds which contain at least one carbon-nitrogen double bond in the heterocyclic ring. When hydrochlorofluorocarbons are formed, the chlorine content may be reduced by reacting the hydrochlorofluorocarbons with HF.Type: ApplicationFiled: June 12, 2003Publication date: November 6, 2003Inventors: Ralph Thomas Baker, Ralph Newton Miller, Viacheslav Alexandrovich Petrov, Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
-
Patent number: 6638365Abstract: A method of preparing a silicon surface for a subsequent processing said such as thermal oxidation, or metal silicide formation, via use of a novel wet chemical clean procedure, has been developed. The novel wet chemical clean procedure is comprised of three specific stages, with the first stage featuring the removal of organic contaminants and the growth of a native oxide layer on the silicon surface. A second stage features removal of the native oxide layer and removal of metallic contaminants from the silicon surface, while the third stage is used to dry the silicon surface. The novel wet chemical clean procedure is performed in less time, and using less chemicals, then counterpart wet chemical cleans also used for the preparation of silicon surfaces for subsequent processing steps.Type: GrantFiled: October 9, 2001Date of Patent: October 28, 2003Assignees: Chartered Semiconductor Manufacturing Ltd., Institute of Materials Research and EngineeringInventors: Jianhui Ye, Simon Chooi, Alex See
-
Publication number: 20030176747Abstract: A process for the production of a fluorinated organic compound, characterized by fluorinating an organic compound having a hydrogen atoms using IF5; and a novel fluorination process for fluorinating an organic compound having a hydrogen atoms by using a fluorinating agent containing IF5 and at least one member selected from the group consisting of acids, bases, salts and additives.Type: ApplicationFiled: December 10, 2002Publication date: September 18, 2003Inventors: Norihiko Yoneda, Tsuyoshi Fukuhara, Kazuhiro Shimokawa, Kenji Adachi, Satoshi Oishi
-
Patent number: 6583328Abstract: A method for the production of 1,1,1,3,3-pentafluoropropene, and particularly to a method characterized by high conversion, yield and selectivity by contacting 2,2-dichloro-1,1,1,3,3,3-hexafluoropropane with hydrogen in the presence of a metal-containing catalyst. The 1,1,1,3,3-pentafluoropropene then can be reacted with hydrogen in the presence of a metal-containing catalyst to produce 1,1,1,3,3-pentafluoropropane.Type: GrantFiled: April 5, 1999Date of Patent: June 24, 2003Assignee: PCBU Services, Inc.Inventors: John Cheng-Ping Qian, Julia Ann Sacarias
-
Patent number: 6403846Abstract: A composition containing less than 95 mol % of a trihydrofluorinated saturated hydrocarbon represented by the following formula (I) Rf1—R1—Rf2 (I) (wherein R1 represents a carbon chain in which CHF and CH2 are bound, and Rf1 and Rf2 are bound to each other to form a ring by a perfluoroalkylene chain of 2 to 4 carbon atoms) and the balance of a tetrahydrofluorinated saturated hydrocarbon having the same carbon number and the same carbon structure as the trihydrofluorinated saturated hydrocarbon, as represented by the following formula (II) Rf1—R2—Rf2 (II) (wherein R2 represents a carbon chain in which CH2 and CH3 are bound, and Rf1 and Rf2 are as defined above) is provided as a composition containing, in a high proportion, trihydrofluorocarbon, a hydrofluorocarbon (HFC) known to have a small global heating coefficient, which has less influence on the global environment, shows less toxicity to animals, and is chemically stable.Type: GrantFiled: February 3, 2000Date of Patent: June 11, 2002Assignees: Japan as Represented by Director General of Agency of Industrial Science and Technology, Nippon Zeon Co., Ltd.Inventors: Akira Sekiya, Toshirou Yamada, Takashi Uruma, Tatsuya Sugimoto
-
Patent number: 6156163Abstract: A reagent comprising a compound of formula (I): R.sub.f --M(X) (Z).sub.n --Y--R, wherein R is a hydrocarbon radical advantageously having at most 10 carbon atoms and being selected from alkyls and aryls; R.sub.f is a radical of formula II: R.sub.1 --(C.XI..sub.2).sub.m --CF.sub.2 --, where R.sub.1 is a fluorine or chlorine atom or a carbon radical, m is 0 or a integer from 0-12, and each .XI., which may be the same or different, is a chlorine or preferably fluorine atom, with the proviso that when m is 0, R.sub.1 is electroattractive, preferably a fluorine atom;n is 0 or 1; M is a non-metal selected from carbon and chalcogens with an atomic number higher than oxygen; and each of X, Y and Z, which are the same or different, is a chalcogen; as well as a generator, for consecutive or simultaneous addition. The reagent is useful for organic synthesis.Type: GrantFiled: November 6, 1997Date of Patent: December 5, 2000Assignee: Rhodia ChimieInventors: Bernard Langlois, Nicolas Roques, Claude Wakselman, Marc Tordeux, Gerard Forat
-
Patent number: 6121212Abstract: The present invention concerns a lubricant for improving the gliding properties of skis and its application to skiing. The lubricant possesses an elevated molecular weight but has a very low melting point. Furthermore, the lubricant does not crystallize easily and thus remains oily or waxy also at low temperatures. The lubricant is constituted of four perfluorinated chains attached to a hydrogenated core in a symmetrical arrangement in such a manner that a tetra-substituted derivative or tetrakis derivative is formed according to the following formula ##STR1## wherein each R.sub.x group can be the same or different and comprises a perfluorinated alkyl group.Type: GrantFiled: March 3, 1999Date of Patent: September 19, 2000Assignee: Centeiro Trading LDAInventor: Gian Paolo Gambaretto
-
Patent number: 6093859Abstract: A process is disclosed for producing the hydrofluorocarbon CF.sub.3 CH.dbd.CF.sub.2. The process involves dehydrofluorinating CF.sub.3 CH.sub.2 CF.sub.3 at an elevated temperature in the vapor phase over a catalyst of (1) aluminum fluoride, (2) fluorided alumina, (3) metal supported on a trivalent aluminum compound containing fluoride anion, (4) lanthanum fluoride, (5) fluorided lanthanum oxide, (6) metal supported on a trivalent lanthanum compound containing fluoride anion, (7) trivalent chromium compounds and/or (8) catalysts of (a) at least one compound selected from the oxides, fluorides and oxyfluorides of magnesium, zinc and mixtures of magnesium and zinc, and optionally (b) at least one compound selected from the oxides, fluorides and oxyfluorides of aluminum, provided that the atomic ratio of aluminum to the total of magnesium and zinc in said catalyst is about 1:4, or less, to produce a product containing CF.sub.3 CH.dbd.CF.sub.2 and HF. The CF.sub.3 CH.dbd.CF.sub.Type: GrantFiled: June 1, 1999Date of Patent: July 25, 2000Assignee: E. I. du Pont de Nemours and CompanyInventors: Mario Joseph Nappa, V. N. Mallikarjuna Rao, Allen Capron Sievert
-
Patent number: 6093860Abstract: A method for producing perfluoro(n-pentane), which comprises fluorinating perfluoro(2-pentene) by bringing the perfluoro(2-pentene) into contact with a fluorine gas in the presence of a solvent.Type: GrantFiled: June 22, 1999Date of Patent: July 25, 2000Assignee: Asahi Glass Company Ltd.Inventors: Kunio Watanabe, Takashi Okazoe, Shin Tatematsu
-
Patent number: 5986151Abstract: A process for the preparation of fluorinated propanes and propenes. CF.sub.3 CH.dbd.CH.sub.2 is produced from CF.sub.3 CH.sub.2 CHF.sub.2 by the sequential steps of dehydrofluorination, a reduction, and a second dehydrofluorination in which the same catalyst is preferably used for each step. Preferably the catalysts is palladium on carbon. The process provides the steps of passing CF.sub.3 CH.sub.2 CHF.sub.2 over a Pd/C catalyst to form CF.sub.3 CH.dbd.CHF; hydrogenating CF.sub.3 CH.dbd.CHF over a Pd/C catalyst to give CF.sub.3 CH.sub.2 CH.sub.2 F; and passing CF.sub.3 CH.sub.2 CH.sub.2 F over a Pd/C catalyst to give CF.sub.3 CH.dbd.CH.sub.2.Type: GrantFiled: August 28, 1998Date of Patent: November 16, 1999Assignee: AlliedSignal Inc.Inventor: Michael Van Der Puy