With Chain Terminating Agent (e.g., Telogen, Etc.) Patents (Class 570/139)
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Patent number: 9139498Abstract: A process is disclosed for producing addition compound CF3CCl2CH2CClXR, wherein X?H, F, Cl or Br, and R?H or a perhalogenated alkyl group, provided that X and R are not both H. The process involves a liquid phase reaction of 1,1,1-trichlorotrifluoroethane with CH2?CXR in the presence of an addition catalyst.Type: GrantFiled: November 7, 2011Date of Patent: September 22, 2015Assignee: THE CHEMOURS COMPANY FC, LLCInventors: Mario Joseph Nappa, Ekaterina N Swearingen, Sergei Rafailovich Sterlin
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Publication number: 20140171697Abstract: A process for producing a fluoroalkyl iodide as a telomer Rf(CF2CF2)nI (wherein Rf is a C1-10 fluoroalkyl group, and n is an integer of from 1 to 6) by telomerization from a fluoroalkyl iodide represented by the formula RfI (wherein Rf is as defined above) as a telogen and tetrafluoroethylene (CF2CF2) as a taxogen, which comprises a liquid phase telomerization step of supplying a homogeneous liquid mixture of the telogen and the taxogen from the lower portion of a tubular reactor, moving the mixture from the lower portion towards the upper portion of the reactor in the presence of a radical initiator over a retention time of at least 5 minutes while the reaction system is kept in a liquid phase state under conditions where no gas-liquid separation will take place, so that the taxogen supplied to the reactor is substantially consumed by the reaction in the reactor, and drawing the reaction product from the upper portion of the reactor.Type: ApplicationFiled: December 11, 2013Publication date: June 19, 2014Applicant: Asahi Glass Company, LimitedInventors: Shoji FURUTA, Yusuke SUGAHARA, Keiko NAKASE, Keisuke MORI
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Patent number: 8236425Abstract: A composition comprises a distribution of telomers of ethylene and at least one fluoroalkyl or perfluoroalkyl halide, the telomers comprising at least one polymethylene segment (—(CH2)n—) and at least one halomethyl group (—CXH2) and optionally comprising at least one non-fluorine heteroatom, and the halogen being selected from iodine and bromine; wherein the distribution has a number average ratio of methylene moieties of the polymethylene segment to the halomethyl groups of at least about 15.Type: GrantFiled: December 27, 2007Date of Patent: August 7, 2012Assignee: 3M Innovative Properties CompanyInventors: George G. I. Moore, Yu Yang, Richard M. Flynn
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Patent number: 8232434Abstract: A novel process for producing a fluoroalkyl iodide telomer is provided, which is able to obtain a fluoroalkyl iodide telomer having a desired chain length, efficiently. A fluoroalkyl iodide represented by the general formula RfI (wherein Rf is a C1-10 fluoroalkyl group) and tetrafluoroethylene are used as a telogen and a taxogen, respectively. These compounds are supplied to a distillation apparatus. In a reaction zone located in an intermediate part of the distillation apparatus, the compounds are subjected to a telomerization reaction in the presence of a metal catalyst with heating to generate a fluoroalkyl iodide telomer represented by the general formula Rf(CF2CF2)nI (wherein Rf is the same as defined above and n is an integer of 1-4). Thereafter, a fraction comprising the fluoroalkyl iodide telomer is separated by distillation.Type: GrantFiled: March 30, 2009Date of Patent: July 31, 2012Assignee: Daikin Industries, Ltd.Inventors: Takeomi Hirasaka, Yoshinori Tanaka
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Patent number: 7964553Abstract: RF-compositions including surfactants, foam stabilizers, monomers, polymers, urethanes, intermediates, metal complexes, phosphate esters as well as telomerization methods are provided.Type: GrantFiled: September 4, 2007Date of Patent: June 21, 2011Assignee: E. I. Dupont de Nmeours and CompanyInventors: Andrew Jackson, Vimal Sharma, E. Bradley Edwards, Janet Boggs, Vicki Hedrick, Stephan Brandstadter, John Chien, Edward Norman, Robert Kaufman, Bruno Ameduri, George K. Kostov
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Publication number: 20110028768Abstract: A novel process for producing a fluoroalkyl iodide telomer is provided, which is able to obtain a fluoroalkyl iodide telomer having a desired chain length, efficiently. A fluoroalkyl iodide represented by the general formula RfI (wherein Rf is a C1-10 fluoroalkyl group) and tetrafluoroethylene are used as a telogen and a taxogen, respectively. These compounds are supplied to a distillation apparatus. In a reaction zone located in an intermediate part of the distillation apparatus, the compounds are subjected to a telomerization reaction in the presence of a metal catalyst with heating to generate a fluoroalkyl iodide telomer represented by the general formula Rf(CF2CF2)nI (wherein Rf is the same as defined above and n is an integer of 1-4). Thereafter, a fraction comprising the fluoroalkyl iodide telomer is separated by distillation.Type: ApplicationFiled: March 30, 2009Publication date: February 3, 2011Inventors: Takeomi Hirasaka, Yoshinori Tanaka
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Patent number: 7601878Abstract: A solid catalyst used in, for example, production of a perfluoroalkyl iodide telomer is effectively and continuously recovered and the recovered catalyst is continuously recycled to the reactor for reuse. A slurry containing a reaction product and the catalyst is drawn from the reaction system, and the catalyst in the drawn slurry is classified by means of a hydrocyclone, whereby a high-concentration slurry whose catalyst concentration is higher than that of the drawn slurry and a low-concentration slurry whose catalyst concentration is lower than that of the drawn slurry are obtained, and the high-concentration slurry is recycled to the reaction system.Type: GrantFiled: March 16, 2007Date of Patent: October 13, 2009Assignee: Daikin Industries, Ltd.Inventors: Tatsuya Hirata, Kouzou Noda, Jun Miki
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Patent number: 7214815Abstract: The present invention provides a metallic copper catalyst for use in an ethylene addition reaction to polyfluoroalkyl iodides, a process for efficiently producing a polyfluoroalkylethyl iodide using such a metal copper catalyst in an ethylene addition reaction to a polyfluoroalkyl iodide, and a process for efficiently producing a polyfluoroalkylethyl iodide from a polyfluoroalkyl iodide using the same metallic copper catalyst in a telomerization reaction and a subsequent ethylene addition reaction.Type: GrantFiled: June 17, 2003Date of Patent: May 8, 2007Assignee: Daikin Industries, Ltd.Inventors: Yoshirou Funakoshi, Jun Miki
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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
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Patent number: 6825389Abstract: The present invention involves a process for the manufacture of &agr;, &ohgr;-diiodoperfluoroalkanes of the formula I—(CF2CF2)n—I, wherein n is an integer between 2 and 6. The latter compounds are produced at relatively high conversions and under relatively mild reaction temperatures and pressures, compared to prior art processes, by the elimination of the gaseous byproduct perfluorocyclobutane throughout the process.Type: GrantFiled: November 21, 2002Date of Patent: November 30, 2004Assignee: DuPont Dow Elastomers LLCInventors: Hasan Dindi, John Joseph Hagedorn, Ming-Hong Hung
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Patent number: 5908966Abstract: Disclosed herein is a telomerization process for preparing fluorinated alkyl iodide telomers, comprising telomerizing a starting polyfluoroalkyl iodide with a terminally unsaturated perfluoro olefin or monochlorofluoro olefin.Type: GrantFiled: December 9, 1997Date of Patent: June 1, 1999Assignee: E. I. du Pont de Nemours and CompanyInventors: Carl George Krespan, Viacheslav A. Petrov
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Patent number: 5639923Abstract: The selectivity of copper as the catalyst for the reaction of short-chain perfluoroalkyl iodides with tetrafluoroethylene is increased if a further transition metal is employed as a cocatalyst.Type: GrantFiled: December 21, 1995Date of Patent: June 17, 1997Assignee: Hoechst AktiengesellschaftInventor: Konrad Von Werner
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Patent number: 5446214Abstract: A cotelomer of --CH.sub.2 CF.sub.2 -- (VDF) units and CF.sub.2 CF(CF.sub.3)-- (HFP) units characterized in that the HEP units comprise at least 33% of all VDF and HFP units in the cotelomer combined. Also claimed is a process for preparing a cotelomer in the liquid state comprising reacting (A) a bromine geminal telogen having the general formula RC(R')Br.sub.2 wherein R and R' are selected from the group consisting of F and perfluorinated alkyl radicals having 1 to 8 carbon atoms; (B) 1,1-difluoroethene, and (C) hexafluoropropene, the molar ratio of said components (A):(B):(C) being x:1:1 to x:1:5, in which x is 1 to 5.Type: GrantFiled: October 27, 1994Date of Patent: August 29, 1995Assignee: Dow Corning CorporationInventors: Gerardo Caporiccio, Richard D. Chambers, Lee D. Proctor
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Patent number: 5268516Abstract: The invention relates to a continuous process for the preparation of perfluoroalkyl iodides containing from 4 to 12 carbon atoms by thermal telomerization of tetrafluoroethylene by pentafluoroethyl iodide or heptafluoroisopropyl iodide in a tubular reactor.According to the invention, 30 to 75% of the tetrafluoroethylene is supplied at the head of the reactor; the remainder is introduced at a point in the reactor located between the 2/5 and 3/4 of the length of the tube.The proportion of undesirable heavy telomers is reduced in this way.Type: GrantFiled: January 13, 1993Date of Patent: December 7, 1993Assignee: Elf Atochem S.A.Inventors: Rene Bertocchio, Georges Lacote, Christophe Verge
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Patent number: 5254773Abstract: A process is disclosed wherein a telomer having the formula BrCH.sub.2 CH.sub.2 (CF.sub.2 CFX).sub.n CH.sub.2 CH.sub.2 Br is prepared by reacting a telogen of the formula Br(CF.sub.2 CFX).sub.n CH.sub.2 CH.sub.2 Br with ethylene in the presence of an organic free-radical generator, wherein X is fluorine or a trifluoromethyl radical and n is an integer having a value of 1-5. It has been found that, when at least 0.05 mole of said free-radical generator is used for each mole of said telogen, the conversion of the telogen to the telomer is surprisingly increased.Type: GrantFiled: February 26, 1993Date of Patent: October 19, 1993Assignee: Dow Corning CorporationInventor: Antony P. Wright
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Patent number: 5196614Abstract: The present invention relates to a novel, catalyst-free method for preparing brominated telomers of chlorotrifluoroethylene. The process comprises reacting chlorotrifluoroethylene with a brominated telogen at a temperature in excess of 200.degree. C. for a time sufficient to produce the telomer.Type: GrantFiled: April 29, 1992Date of Patent: March 23, 1993Assignee: Dow Corning CorporationInventors: Gerardo Caporiccio, Gerald A. Gornowicz, Bernard Boutevin
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Patent number: 5068471Abstract: A process for continuous telomerization is described, in which at least one telogenic compound and at least one taxogenic compound are reacted at from 40.degree. to 150.degree. C. under a pressure of from 0.1 to 3 MPa in the presence of at least one catalyst in an elongate cylindrical reaction space. After it has left the reaction space, the reaction mixture is separated, for example by distillation, the desired higher-molecular telomers are discharged as the bottom product, and the undesired low-molecular telomerization products are stripped off over the top, condensed and recycled into the process in a first circulation. In a second circulation, a part of the reaction mixture is taken off towards the end of the reaction space and reintroduced into the initial part of the reaction space. This allows an improved space-time yield and a better selection of defined product cuts.Type: GrantFiled: December 19, 1990Date of Patent: November 26, 1991Assignee: Hoechst AktiengesellschaftInventors: Norbert Paul, Rudolf Huber, Ingolf Mielke
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Patent number: 5015790Abstract: Fluorine-containing iodo-substituted 1-hexenes, their preparation by the addition of two moles of ethylene to fluorine-containing iodo olefins, and their dehydroiodination to fluorine-containing 1,5-dienes are disclosed.Type: GrantFiled: December 13, 1989Date of Patent: May 14, 1991Assignee: E. I. Du Pont de Nemours and CompanyInventor: Ming-Hong Hung
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Patent number: 4849556Abstract: Telomers are prepared by reacting chlorotrifluoroethylene with 1,1,2-trichlorotrifluoroethane (CCl.sub.2 FCF.sub.2 Cl) in the presence of metallic iron or stainless steel, and optionally, a halide-containing compound selected from the group consisting of tetrabutyl ammonium bromide, tetramethyl ammonium chloride, n-chlorosuccinimide, triethylamine hydrochloride, LiCl, MoCl.sub.5 and FeCl.sub.3. The reaction is conducted at a temperature of from about 150.degree. C. to about 200.degree. C. in a nitrile group-containing solvent selected from the group consisting of acetonitrile, propionitrile and ethyl cyanoacetate. Preferably, the CCl.sub.2 FCF.sub.2 Cl and chlorotrifluoroethylene are present in a mole ratio of from about 1:1 to about 3:1. respectively, to minimize the amount of high molecular weight species formed during the reaction. The telomers of this invention are useful for preparing non-flammable hydraulic fluids.Type: GrantFiled: November 5, 1987Date of Patent: July 18, 1989Assignee: Occidental Chemical CorporationInventors: Bobby F. Dannels, Deborah J. Olsen
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Patent number: 4833274Abstract: New perfluoroalkanes and haloperfluoroalkanes, having low melting point and high thermal and chemical stability, constituted by preferably branched perfluorinated and haloperfluorinated chains, obtained by starting from precursors containing two halogen atoms equal to or different from each other, one of them necessarily being an iodine atom, which are reacted with C.sub.3 F.sub.6 and possibly subsequently halogenated with either fluorine or chlorine or bromine.Type: GrantFiled: January 28, 1988Date of Patent: May 23, 1989Assignee: Ausimont S.p.A.Inventors: Gerardo Caporiccio, Gianangelo Bargigia, Claudio Tonelli, Vito Tortelli
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Patent number: 4808760Abstract: Telomers are prepared by reacting chlorotrifluoroethylene with 1,2-dibromo-2-chlorotrifluoroethane (CBrClFCF.sub.2 Br) in the presence of a redox catalyst system comprising a metal halide selected from the group consisting of FeCl.sub.3, FeBr.sub.3, CuBr.sub.2, CuCl.sub.2, TiCl.sub.4, VCl.sub.3, and NiCl.sub.2, and a reducing agent selected from the group consisting of Fe, Ni, Cu, Ti, V and benzoin. The preferred catalyst system is ferric chloride and nickel. The telomers of this invention have the structural formula ##STR1## where n is in the range of 1 to 10, and are useful for preparing non-flammable hydraulic fluids.Type: GrantFiled: January 6, 1986Date of Patent: February 28, 1989Assignee: Occidental Chemical CorporationInventors: Bobby F. Dannels, Michael J. Fifolt, David Y. Tang
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Patent number: 4691065Abstract: An improved process for preparaing telomers of chlorotrifluoroethylene comprises the solution telomerization reaction of chlorotrifluoroethylene with carbon tetrachloride in the presence of a catalytic amount of cupric chloride (CuCl.sub.2) and an iron reductant. Preferably, the solvent for the system comprises acetonitrile, and the telomerization is carried out under elevated pressure conditions and at a temperature in the range of from about 90.degree. C. to about 150.degree. C. The crude telomer prepared by this process can be fluorinated to produce a stabilized oil or grease.Type: GrantFiled: November 2, 1983Date of Patent: September 1, 1987Assignee: Occidental Chemical CorporationInventor: Bobby F. Dannels
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Patent number: 4577044Abstract: Telomers formed by reacting chlorotrifluoroethylene with fluoroxytrifluoromethane are disclosed. The telomerization reaction is conducted in either liquid chlorotrifluoroethylene without a solvent or in solution. The telomers thus formed can optionally be fluorinated by reaction with a suitable fluorinating agent to improve their stability.Type: GrantFiled: February 11, 1985Date of Patent: March 18, 1986Assignee: Occidental Chemical CorporationInventors: Donald H. Campbell, Michael J. Fifolt, Mohan S. Saran
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Patent number: 4533762Abstract: A telomerization process comprises reacting chlorotrifluoroethylene with bisfluoroxydifluoromethane. The telomerization reaction is conducted in either liquid chlorotrifluoroethylene without a solvent or in solution. The telomers thus formed can optionally be fluorinated by reaction with a suitable fluorinating agent to improve their stability.Type: GrantFiled: October 24, 1983Date of Patent: August 6, 1985Assignee: Occidental Chemical CorporationInventors: Donald H. Campbell, Michael J. Fifolt, Mohan S. Saran
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Patent number: 4296265Abstract: Hexafluoropropene oligomers are prepared from hexafluoropropene in a high conversion by contacting gaseous hexafluoropropene with a catalyst comprising an alkali metal fluoride supported on activated charcoal or nickel oxide.Type: GrantFiled: July 18, 1980Date of Patent: October 20, 1981Assignee: Daikin Kogyo Co., Ltd.Inventors: Yohnosuke Ohsaka, Takashi Tohzuka