With Chain Terminating Agent (e.g., Telogen, Etc.) Patents (Class 570/139)
  • Patent number: 9139498
    Abstract: 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: Grant
    Filed: November 7, 2011
    Date of Patent: September 22, 2015
    Assignee: THE CHEMOURS COMPANY FC, LLC
    Inventors: Mario Joseph Nappa, Ekaterina N Swearingen, Sergei Rafailovich Sterlin
  • Publication number: 20140171697
    Abstract: 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: Application
    Filed: December 11, 2013
    Publication date: June 19, 2014
    Applicant: Asahi Glass Company, Limited
    Inventors: Shoji FURUTA, Yusuke SUGAHARA, Keiko NAKASE, Keisuke MORI
  • Patent number: 8236425
    Abstract: 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: Grant
    Filed: December 27, 2007
    Date of Patent: August 7, 2012
    Assignee: 3M Innovative Properties Company
    Inventors: George G. I. Moore, Yu Yang, Richard M. Flynn
  • Patent number: 8232434
    Abstract: 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: Grant
    Filed: March 30, 2009
    Date of Patent: July 31, 2012
    Assignee: Daikin Industries, Ltd.
    Inventors: Takeomi Hirasaka, Yoshinori Tanaka
  • Patent number: 7964553
    Abstract: RF-compositions including surfactants, foam stabilizers, monomers, polymers, urethanes, intermediates, metal complexes, phosphate esters as well as telomerization methods are provided.
    Type: Grant
    Filed: September 4, 2007
    Date of Patent: June 21, 2011
    Assignee: E. I. Dupont de Nmeours and Company
    Inventors: Andrew Jackson, Vimal Sharma, E. Bradley Edwards, Janet Boggs, Vicki Hedrick, Stephan Brandstadter, John Chien, Edward Norman, Robert Kaufman, Bruno Ameduri, George K. Kostov
  • Publication number: 20110028768
    Abstract: 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: Application
    Filed: March 30, 2009
    Publication date: February 3, 2011
    Inventors: Takeomi Hirasaka, Yoshinori Tanaka
  • Patent number: 7601878
    Abstract: 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: Grant
    Filed: March 16, 2007
    Date of Patent: October 13, 2009
    Assignee: Daikin Industries, Ltd.
    Inventors: Tatsuya Hirata, Kouzou Noda, Jun Miki
  • Patent number: 7214815
    Abstract: 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: Grant
    Filed: June 17, 2003
    Date of Patent: May 8, 2007
    Assignee: Daikin Industries, Ltd.
    Inventors: Yoshirou Funakoshi, Jun Miki
  • Patent number: 7038095
    Abstract: 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: Grant
    Filed: February 5, 2002
    Date of Patent: May 2, 2006
    Assignee: Daikin Industries, Ltd.
    Inventors: Yukio Homoto, Kunitada Tanaka
  • Patent number: 6825389
    Abstract: 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: Grant
    Filed: November 21, 2002
    Date of Patent: November 30, 2004
    Assignee: DuPont Dow Elastomers LLC
    Inventors: Hasan Dindi, John Joseph Hagedorn, Ming-Hong Hung
  • Patent number: 5908966
    Abstract: 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: Grant
    Filed: December 9, 1997
    Date of Patent: June 1, 1999
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Carl George Krespan, Viacheslav A. Petrov
  • Patent number: 5639923
    Abstract: 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: Grant
    Filed: December 21, 1995
    Date of Patent: June 17, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Konrad Von Werner
  • Patent number: 5446214
    Abstract: 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: Grant
    Filed: October 27, 1994
    Date of Patent: August 29, 1995
    Assignee: Dow Corning Corporation
    Inventors: Gerardo Caporiccio, Richard D. Chambers, Lee D. Proctor
  • Patent number: 5268516
    Abstract: 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: Grant
    Filed: January 13, 1993
    Date of Patent: December 7, 1993
    Assignee: Elf Atochem S.A.
    Inventors: Rene Bertocchio, Georges Lacote, Christophe Verge
  • Patent number: 5254773
    Abstract: 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: Grant
    Filed: February 26, 1993
    Date of Patent: October 19, 1993
    Assignee: Dow Corning Corporation
    Inventor: Antony P. Wright
  • Patent number: 5196614
    Abstract: 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: Grant
    Filed: April 29, 1992
    Date of Patent: March 23, 1993
    Assignee: Dow Corning Corporation
    Inventors: Gerardo Caporiccio, Gerald A. Gornowicz, Bernard Boutevin
  • Patent number: 5068471
    Abstract: 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: Grant
    Filed: December 19, 1990
    Date of Patent: November 26, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Norbert Paul, Rudolf Huber, Ingolf Mielke
  • Patent number: 5015790
    Abstract: 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: Grant
    Filed: December 13, 1989
    Date of Patent: May 14, 1991
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Ming-Hong Hung
  • Patent number: 4849556
    Abstract: 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: Grant
    Filed: November 5, 1987
    Date of Patent: July 18, 1989
    Assignee: Occidental Chemical Corporation
    Inventors: Bobby F. Dannels, Deborah J. Olsen
  • Patent number: 4833274
    Abstract: 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: Grant
    Filed: January 28, 1988
    Date of Patent: May 23, 1989
    Assignee: Ausimont S.p.A.
    Inventors: Gerardo Caporiccio, Gianangelo Bargigia, Claudio Tonelli, Vito Tortelli
  • Patent number: 4808760
    Abstract: 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: Grant
    Filed: January 6, 1986
    Date of Patent: February 28, 1989
    Assignee: Occidental Chemical Corporation
    Inventors: Bobby F. Dannels, Michael J. Fifolt, David Y. Tang
  • Patent number: 4691065
    Abstract: 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: Grant
    Filed: November 2, 1983
    Date of Patent: September 1, 1987
    Assignee: Occidental Chemical Corporation
    Inventor: Bobby F. Dannels
  • Patent number: 4577044
    Abstract: 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: Grant
    Filed: February 11, 1985
    Date of Patent: March 18, 1986
    Assignee: Occidental Chemical Corporation
    Inventors: Donald H. Campbell, Michael J. Fifolt, Mohan S. Saran
  • Patent number: 4533762
    Abstract: 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: Grant
    Filed: October 24, 1983
    Date of Patent: August 6, 1985
    Assignee: Occidental Chemical Corporation
    Inventors: Donald H. Campbell, Michael J. Fifolt, Mohan S. Saran
  • Patent number: 4296265
    Abstract: 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: Grant
    Filed: July 18, 1980
    Date of Patent: October 20, 1981
    Assignee: Daikin Kogyo Co., Ltd.
    Inventors: Yohnosuke Ohsaka, Takashi Tohzuka