Processes For Forming The Carbonyl Group Patents (Class 562/851)
  • Patent number: 8513458
    Abstract: The present invention provides a method for inexpensively, efficiently, safely, and continuously producing COF2, without using highly toxic raw materials such as phosgene or difficult-to-get raw materials, with no risk of explosion or the like. Tetrafluoroethylene gas and oxygen gas are introduced into a reactor, and they are then heated in a gas phase in the absence of nitrogen gas for reaction, so as to produce carbonyl fluoride. The reactor is preferably a tubular reaction tube. As such tetrafluoroethylene gas, unpurified or purified tetrafluoroethylene gas obtained by heating HCFC-22 gas for thermal decomposition can be used. According to the present invention, COF2 that is useful as cleaning gas for CVD devices (chemical vapor deposition method) can be inexpensively, efficiently, and safely produced.
    Type: Grant
    Filed: September 26, 2006
    Date of Patent: August 20, 2013
    Assignee: Nat'l Institute of Advanced Industrial Science and Technology
    Inventors: Heng-dao Quan, Masanori Tamura, Akira Sekiya
  • Patent number: 8394989
    Abstract: Provided are fluorinated oxy-carboxylic acids, derivatives of oxy-carboxylic acids, and methods of preparing oxy-carboxylic acids and derivatives thereof.
    Type: Grant
    Filed: September 26, 2008
    Date of Patent: March 12, 2013
    Assignee: 3M Innovative Properties Company
    Inventors: Werner Schwertfeger, Klaus Hintzer, Egon Obermaier
  • Publication number: 20130018201
    Abstract: A process for the preparation of a compound of formula (I): which is useful as an intermediate in the preparation of pharmaceutically active compounds.
    Type: Application
    Filed: July 5, 2012
    Publication date: January 17, 2013
    Inventors: Beat Birrer, Leo Clarke, Walter Deichtmann, John Hayes, Julius Jeisy, Christian Lautz, Rainer E. Martin, Michael Meade, Joaquim Pintao, Michelangelo Scalone, Juergen Schaefer, Dennis Smith, Andreas Staempfli, Joachim Veits, Christian Walch, Andrew Walsh, Andreas Zogg
  • Publication number: 20110251427
    Abstract: A polyfluoroalkane carboxylic acid represented by the following general formula: CnF2n+1(CH2CF2)m(CF2CF2)l?1CF2COOM (M: an alkali metal, a NH4 group or H; n: an integer of 1 to 6; m: an integer of 1 to 4; and l: 1 or 2) can be produced by hydrolysis reaction of polyfluoroalkane carboxylic acid fluoride represented by the following general formula: CnF2n+1(CH2CF2)m(CF2CF2)l?1CF2COF , where its carboxylic acid salt can be formed as an alkali metal salt, or a NH4 salt. The polyfluoroalkane carboxylic acid (or its salt) can act as a surfactant having distinguished monomer emulsificability and latex stability when used as an emulsifying agent or as a dispersing agent for polymerization reaction of fluorine-containing monomers, or as an effective surfactant capable of enhancing the micelles solubility of fluorine-containing monomers such as vinylidene fluoride, etc., when used as an emulsifying agent or a dispersing agent for homopolymerization or copolymerization reaction of vinylidene fluoride.
    Type: Application
    Filed: July 17, 2007
    Publication date: October 13, 2011
    Applicant: Nippon Mektron, Limited
    Inventors: Daisuke Murai, Takashi Enokida, Seiichiro Murata
  • Patent number: 7880039
    Abstract: Carbonyl fluoride, which can also be used as an etching gas, can be prepared by photochemical oxidation of chlorodifluoromethane or trifluoromethane with light, for example with light of a wavelength ?280 nm in the presence of chlorine.
    Type: Grant
    Filed: February 9, 2005
    Date of Patent: February 1, 2011
    Assignee: Solvay Fluor GmbH
    Inventors: Max Braun, Johannes Eicher
  • Publication number: 20100191013
    Abstract: The present invention provides a method for inexpensively, efficiently, safely, and continuously producing COF2, without using highly toxic raw materials such as phosgene or difficult-to-get raw materials, with no risk of explosion or the like. Tetrafluoroethylene gas and oxygen gas are introduced into a reactor, and they are then heated in a gas phase in the absence of nitrogen gas for reaction, so as to produce carbonyl fluoride. The reactor is preferably a tubular reaction tube. As such tetrafluoroethylene gas, unpurified or purified tetrafluoroethylene gas obtained by heating HCFC-22 gas for thermal decomposition can be used. According to the present invention, COF2 that is useful as cleaning gas for CVD devices (chemical vapor deposition method) can be inexpensively, efficiently, and safely produced.
    Type: Application
    Filed: September 26, 2006
    Publication date: July 29, 2010
    Applicant: NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY
    Inventors: Heng-dao Quan, Masanori Tamura, Akira Sekiya
  • Patent number: 7592484
    Abstract: The present invention relates to a method for producing carbonyl difluoride comprising a step of reacting trifluoromethane with oxygen or an oxygen-containing gas while heating.
    Type: Grant
    Filed: April 26, 2005
    Date of Patent: September 22, 2009
    Assignee: Daikin Industries, Ltd.
    Inventors: Seiji Takubo, Takuji Kume, Akinori Yamamoto, Chie Sawauchi, Hisako Nakamura
  • Patent number: 7083705
    Abstract: The invention provides a process for producing a fluorine-containing compound from an inexpensive material. Namely, Compound I such as RACH2OH is reacted with Compound II such as XCORB to form Compound III such as RACH2OCORB, followed by fluorination in a liquid phase to form Compound IV such as RAFCF2OCORBF, which is converted to Compound V such as RAFCOF and/or Compound VI such as RBFCOF. RA is an alkyl group or the like, RB is a perhalogenoalkyl group or the like, RAF and RBF are fluorinated RA and RB, and X is halogen.
    Type: Grant
    Filed: August 11, 2004
    Date of Patent: August 1, 2006
    Assignee: Asahi Glass Company, Limited
    Inventors: Takashi Okazoe, Kunio Watanabe, Shin Tatematsu, Hidenobu Murofushi
  • Patent number: 6919480
    Abstract: The present invention provides novel processes for preparing a fluorinated acyl fluoride and a fluorinated vinyl ether.
    Type: Grant
    Filed: December 5, 2003
    Date of Patent: July 19, 2005
    Assignee: Asahi Glass Company, Limited
    Inventors: Takashi Okazoe, Kunio Watanabe, Masahiro Ito, Daisuke Shirakawa, Shin Tatematsu
  • Publication number: 20040147779
    Abstract: Provided is a process of obtaining 1,1,1,3,3,3-hexafluoro-2-propanol (“HFIP”) from a composition comprising an HFIP hydrolyzable precursor. The HFIP hydrolyzable precursor is a compound, other than sevoflurane itself, that has an intact 1,1,1,3,3,3-hexafluoroisopropoxy moiety[(CF3)2CHO—], and contains one or more moieties susceptible to acidic hydrolysis, such that HFIP is released upon such treatment. The process is useful, among other things, for recovering HFIP from waste streams associated with the synthesis of the inhalation anesthetic, fluoromethyl 2,2,2-trifluoro-1-(trifluoromethyl)ethyl ether (“sevoflurane”). The process includes heating the composition with a strong protic acid to a temperature effective to hydrolyze at least some of the HFIP hydrolyzable precursor to HFIP, and then isolating the HFIP from the heated composition.
    Type: Application
    Filed: January 12, 2004
    Publication date: July 29, 2004
    Applicant: Baxter International Inc
    Inventors: Leonid A. Rozov, Ralph A. Lessor
  • Publication number: 20040147778
    Abstract: A process for the synthesis of (per)fluorinated mono-functional carbonyl compounds having the following formula (I):
    Type: Application
    Filed: January 9, 2004
    Publication date: July 29, 2004
    Applicant: SOLVAY SOLEXIS S.p.A.
    Inventors: Giovanni Fontana, Walter Navarrini
  • Patent number: 6747174
    Abstract: The present invention provides novel processes for preparing a fluorinated acyl fluoride and a fluorinated vinyl ether.
    Type: Grant
    Filed: January 28, 2003
    Date of Patent: June 8, 2004
    Assignee: Asahi Glass Company, Limited
    Inventors: Takashi Okazoe, Kunio Watanabe, Masahiro Ito, Daisuke Shirakawa, Shin Tatematsu
  • Publication number: 20030236436
    Abstract: A process for preparing acylfluorides by reaction of carbonyl fluoride COF2 with compounds having general formula:
    Type: Application
    Filed: June 16, 2003
    Publication date: December 25, 2003
    Applicant: SOLVAY SOLEXIS S.p.A.
    Inventors: Marco Galimberti, Walter Navarrini
  • Patent number: 6586626
    Abstract: The invention provides a process for producing a fluorine-containing compound from an inexpensive material. Namely, Compound I such as RACH2OH is reacted with Compound II such as XCORB to form Compound III such as RACH2OCORB, followed by fluorination in a liquid phase to form Compound IV such as RAFCF2OCORBF, which is converted to Compound V such as RAFCOF and/or Compound VI such as RBFCOF. RA is an alkyl group or the like, RB is a perhalogenoalkyl group or the like, RAF and RBF are fluorinated RA and RB, and X is halogen.
    Type: Grant
    Filed: September 24, 2001
    Date of Patent: July 1, 2003
    Assignee: Asahi Glass Company, Limited
    Inventors: Takashi Okazoe, Kunio Watanabe, Shin Tatematsu, Hidenobu Murofushi
  • Patent number: 6023002
    Abstract: Described is a reaction of a fluorinated alkoxide with an alkyl fluorovinylalkyl ether, the alkyl fluorovinylalkyl ether having alpha-beta carbon-carbon unsaturation relative to the ether oxygen, to produce a hydrofluoroether.
    Type: Grant
    Filed: January 26, 1998
    Date of Patent: February 8, 2000
    Assignee: 3M Innovative Properties Company
    Inventors: Frederick E. Behr, Yuri Cheburkov
  • Patent number: 6002055
    Abstract: Highly fluorinated epoxides are reacted with dihalogens in the presence of metal and metal containing reaction promoters to give dihalofluoromethanes and their homologues.
    Type: Grant
    Filed: August 19, 1998
    Date of Patent: December 14, 1999
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Zhen-Yu Yang
  • Patent number: 5905169
    Abstract: A process is disclosed for preparing polyhaloacyl fluorides such as trifluoroacetyl fluoride and difluoroacetyl fluoride by oxidizing 1-chloro-1,2,2,2-trifluoroethanes and 1,1-dichloro-2,2-difluoroethane, respectively with oxygen.
    Type: Grant
    Filed: March 20, 1995
    Date of Patent: May 18, 1999
    Assignee: E. I. Du Pont De Nemours and Company
    Inventor: Stephen Ernest Jacobson
  • Patent number: 5712418
    Abstract: The present invention is directed to the process of preparing a peptide comprising reacting a first amino acid or peptide with an amino acid fluoride of the formula: ##STR1## or the acid fluoride salts thereof wherein BLK is an N-amino protecting groupAA is an amino acid residue andX is H or a protecting group useful,and the first amino and peptide have a free amino group and a blocked carboxy end.
    Type: Grant
    Filed: August 2, 1994
    Date of Patent: January 27, 1998
    Assignee: Research Corporation Technologies, Inc.
    Inventors: Louis A. Carpino, Ayman Ahmed El-Faham
  • Patent number: 5684193
    Abstract: The invention relates to a process for the preparation of perfluoropropionyl fluoride (II) by the isomerization of hexafluoropropene oxide (I): ##STR1## wherein the reaction medium used is a liquid complex ammonium hydrofluoride.
    Type: Grant
    Filed: November 12, 1996
    Date of Patent: November 4, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gunter Siegemund, Raimund Franz
  • Patent number: 5616794
    Abstract: A process for preparing fluorocarboxylic acid halides comprises the steps of (a) forming a starting composition comprising (i) at least one fluorosulfonic acid halide comprising at least one halosulfonyldifluoromethyl group (--Cf.sub.2 SO.sub.2 X, wherein X is halogen); and (ii) at least one Group III or Group V Lewis acid; and (b) allowing the fluorosulfonic acid halide and the Lewis acid to react to form a product composition comprising at least one fluorocarboxylic acid halide. The process enables the preparation of even higher molecular weight fluorocarboxylic acid halides in good yield.
    Type: Grant
    Filed: November 17, 1995
    Date of Patent: April 1, 1997
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Frederick E. Behr, Yuri Cheburkov
  • Patent number: 5569782
    Abstract: A process for preparing polyfluorochloro- and perfluorocarbonyl chlorides, for example for preparing perfluoropropionyl chloride, chlorodifluoroacetyl chloride or trifluoroacetyl chloride, in which starting materials are employed which have a CHCl.sub.2 group which is converted to a C(O)Cl group by photochemical oxidation with oxygen in the presence of added elemental chlorine and under exposure to activating irradiation by light having a wavelength .lambda..gtoreq.290 nm. The procedure is preferably unpressurized. Outstanding conversions with high selectivity are achieved using doped Hg light sources.
    Type: Grant
    Filed: December 20, 1994
    Date of Patent: October 29, 1996
    Assignee: Solvay Fluor und Derivate GmbH
    Inventors: Max Braun, Werner Rudolph, Kerstin Eichholz
  • Patent number: 5557010
    Abstract: Process for preparing a 2,3-dihaloperfluoropropionyl halide wherein an alkali metal chloride, bromide or iodide is contacted with a 3-haloperfluoropropene oxide in admixture in an inert liquid reaction medium.
    Type: Grant
    Filed: June 25, 1992
    Date of Patent: September 17, 1996
    Assignee: The Dow Chemical Company
    Inventors: Kevin P. Darst, Bobby R. Ezzell, Nobuyuki Ishibe
  • Patent number: 5504248
    Abstract: Halogenated compounds are prepared by ring opening reactions of highly fluorinated cyclopropanes with chlorine, bromine, iodine, or mixtures thereof at temperatures over 100.degree. C. A novel compound, which is one type of compound produced, is a highly fluorinated and halogenated ether and other novel compounds are starting materials or products. The products of the process are useful as chain transfer agents for certain free radical polymerizations, and as chemical intermediates in the preparation of various products such as surfactants and textile surface treatments.
    Type: Grant
    Filed: July 28, 1994
    Date of Patent: April 2, 1996
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Paul J. Krusic, Zhen-Yu Yang
  • Patent number: 5449825
    Abstract: Process for preparing haloperfluoro and perfluoro ethers wherein a metal halide is reacted with a 3-haloperfluoropropene oxide to obtain a 2,3-dihaloperfluorocarbonyl fluoride; a metal halide, 2,3-dihaloperfluorocarbonyl fluoride and 3-haloperfluoropropene oxide are reacted to obtain a 2-(2',3'-dihaloperfluoropropoxy)-3-haloperfluoropropionyl fluoride; 2-(2',3'-dihaloperfluoropropoxy)-3-haloperfluoropropionyl fluoride is decarboxylated and dehalogenated to obtain perfluorovinylallylether. Alternatively, 2-(2',3'-dihaloperfluoropropoxy)-3-haloperfluoropropionyl fluoride is reacted with metal halide and 3-haloperfluoropropene oxide to obtain a 2-[2'-(2",3"-dihaloperfluoropropoxy)-3'-haloperfluoropropoxy]-3-haloperflu oropropionyl fluoride, or a higher polyether, and 2-[2'-(2",3"-dihaloperfluoropropoxy)-3'-haloperfluoropropoxy]-3-haloperflu oropropionyl fluoride or the polyether is decarboxylated and dehalogenated to obtain a 3,6-dioxa-5-halodifluoromethylperfluoronona-1,8-diene or the corresponding polyether.
    Type: Grant
    Filed: January 18, 1994
    Date of Patent: September 12, 1995
    Assignee: The Dow Chemical Company
    Inventors: Nobuyuki Ishibe, Tien K. Tran, Charles W. Martin
  • Patent number: 5414119
    Abstract: Hexafluoropropylene oxide (HFPO) compounds, including polymers, expressed by the general chemical formula (1) below: ##STR1## wherein R.sup.1 is a single bond, an alkylene group of 1 to 10 carbon atoms, or said alkylene group in which a part of, or all of, the hydrogen atoms are substituted by fluorine atoms, Rf is a fluorine atom, a perfluoroalkyl group of 1 to 10 carbon atoms, or a perfluoroalkyl ether group, and n is 0 or an integer of at least 1. A manufacturing method for the HFPO compounds which is characterized by the reaction between hexafluoropropylene oxide and a vinyl group containing compound, expressed by the general chemical formula (2) below: ##STR2## wherein R.sup.1 and Rf are same as above. The compounds have utility as important intermediate raw materials for the production of novel functional silicone compounds having HFPO polymer units.
    Type: Grant
    Filed: March 1, 1994
    Date of Patent: May 9, 1995
    Assignee: Shin Etsu Chemical Co., Ltd.
    Inventors: Yasuo Tarumi, Noriyuki Koike, Toshio Takago
  • Patent number: 5399754
    Abstract: A process of producing a perfluorocarboxylic acid fluoride having the formula (1): ##STR1## wherein n is an integer of at least 2, comprising effecting oligomerization of hexafluoropropylene oxide in the presence of an alkali metal fluoride a sulfone or a mixture of a sulfone with an ether having the formula (2):CH.sub.3 O(CH.sub.2 CH.sub.2 O).sub.m CH.sub.3 (2)where m is an integer of 2 to 6. This process makes it possible to improve production yield of hexafluoropropylene oxide oligomers remarkably, and to raise a reaction temperature for the oligomerization, as compared with conventional methods, thereby shortening reaction time therefor.
    Type: Grant
    Filed: April 26, 1994
    Date of Patent: March 21, 1995
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Masayuki Oyama, Kazutoshi Munezawa, Hitoshi Kinami
  • Patent number: 5241115
    Abstract: A method for the preparation of carbonyl difluoride which comprises contacting carbonyl chloride fluoride with an active carbon catalyst.
    Type: Grant
    Filed: March 10, 1989
    Date of Patent: August 31, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: David Ashton, Thomas A. Ryan
  • Patent number: 5208373
    Abstract: A process for the preparation of perfluoropolyetheracyl fluorides of formula (I)F.sub.3 C(CF.sub.2).sub.2 --O--[CF(CF.sub.3)CF.sub.2 --O--].sub.n CF(CF.sub.3)COF (I)in which n is an integer from 0-60, wherein hexafluoropropylene oxide is oligomerized in the presence of CsF and a polyethylene glycol dimethyl ether and the reaction mixture thus formed is reacted with at least one of the halogen compounds HCl, HBr, BCl.sub.3, PCl.sub.3, SCl.sub.2 and R.sub.m SiCl.sub.4-m, where m=0, 1, 2 or 3 and R=C.sub.1 -C.sub.3 -alkyl or phenyl, dissolved in an aprotic solvent.
    Type: Grant
    Filed: February 12, 1992
    Date of Patent: May 4, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Matthias Meyer
  • Patent number: 5093523
    Abstract: A perfluorosuccinylfluoride is prepared by the reaction of a gaseous mixture of 1,4-dibromoperfluorobutane with SO.sub.3 in oleum with at least 65% of free SO.sub.3 containing a catalyst comprising, besides mono- and bi-valent mercury sulphates, B.sub.2 O.sub.3 in quantities of from 0.3% to 8% by weight with respect to the free SO.sub.3 present in the "oleum" during course of the reaction.
    Type: Grant
    Filed: April 26, 1990
    Date of Patent: March 3, 1992
    Assignee: Ausimont S.r.l.
    Inventor: Claudio Gervasutti
  • Patent number: 5093522
    Abstract: The present invention relates to new carboxylic acid halides containing trifluoromethyl groups, of the formula (I) ##STR1## in which the symbols used have the meanings given in the description, a process for their preparation by reaction of perhalogenoalkanes with carbon monoxide and an olefin and their use for the preparation of textile auxiliaries.
    Type: Grant
    Filed: September 12, 1990
    Date of Patent: March 3, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Dietmar Bielefeldt, Heinz Ziemann
  • Patent number: 5087748
    Abstract: A continuous process for the preparation of perfluorinated carbonyl fluorides from hexafluoropropene oxide (HFPO), in which HFPO is continuously oligomerized in a catalyst solution in devices which allow separation of the heavy product phase from the catalyst phase during the reaction, is described. Different oligomer distributions can be achieved by choice of the catalyst and different operating temperatures. The reaction itself takes place always in the substantial absence of the product which is formed, and achieves a considerable saving in time.
    Type: Grant
    Filed: January 11, 1990
    Date of Patent: February 11, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Manfred Finke, Gunter Siegemund, Heinz Strutz
  • Patent number: 5047584
    Abstract: A process for the preparation of pentahaloethoxy benzoyl halide compounds comprisingA) chlorinating p-cresyl trifluoroacetate to form p-.alpha., .alpha.-dichloro-.beta.-,.beta.-,.beta.-trifluoroethoxy benzotrichloride;B) converting the p-.alpha., .alpha.-dichloro-.beta.-,.beta.-,.beta.-trifluoroethoxy benzotrichloride to p-pentafluoroethoxy benzoyl fluoride.
    Type: Grant
    Filed: December 9, 1985
    Date of Patent: September 10, 1991
    Assignee: Occidental Chemical Corp.
    Inventors: James J. Maul, Byron R. Cotter
  • Patent number: 5025105
    Abstract: A process for preparing bromodifluoroacetylfluoride characterized in that a gaseous stream of oxygen-diluted ozone is reacted, at temperatures ranging from -100.degree. C. to +80.degree. C., with 1,4-dibromohexafluorobutene-2 optionally dissolved in a solvent which is inert under the reaction conditions, with consequent obtainment of the corresponding ozonide and, subsequently, the ozonide is subjected to a heat treatment at temperatures ranging from 100.degree. to 300.degree. C., with consequent obtainment of bromodifluoroacetylfluoride.
    Type: Grant
    Filed: June 27, 1990
    Date of Patent: June 18, 1991
    Assignee: AUSIMONT S.r.l.
    Inventors: Silvana Modena, Ezio Strepparola
  • Patent number: 5025093
    Abstract: A method of breaking down perfluoropolyethers into lower molecular weight fragments by pyrolysis is disclosed. The perfluoropolyethers are pyrolyzed generally at above about 350.degree. C. Volatile lower molecular weight components are condensed and collected. Various molecular weight fractions and collected. Various molecular weight fractions can be obtained by taking appropriate distillation cuts.
    Type: Grant
    Filed: January 5, 1990
    Date of Patent: June 18, 1991
    Assignee: Exfluor Research Corporation
    Inventors: Richard J. Lagow, Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu M. Kawa
  • Patent number: 4987254
    Abstract: Fluorinated carboxylic acid fluorides of the formula I ##STR1## can be prepared from fluorinated vinyl ethers of the formula II ##STR2## by reacting the vinyl ethers with an oxygen-containing gas in the presence of a catalytic amount of a Lewis acid. Perfluorinated carboxylic acids and derivatives thereof can be prepared from the carboxylic acid fluorides by secondary reactions, for example hydrolysis, esterification or aminolysis.
    Type: Grant
    Filed: August 3, 1989
    Date of Patent: January 22, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Werner Schwertfeger, Klaus Hintzer, Peter Blickle
  • Patent number: 4985594
    Abstract: Process for the preparation of fluorinated carboxylic acid fluoridesFluorinated carboxylic acid fluorides of the Formula I ##STR1## can be prepared from fluorinated vinyl ethers of the Formula II ##STR2## by heating the vinyl ethers to a temperature of 100.degree. to 350.degree. C.Perfluorinated carboxylic acids and derivatives thereof can be prepared from the carboxylic acid fluorides by secondary reactions, for example hydrolysis, esterification or aminolysis.
    Type: Grant
    Filed: August 3, 1989
    Date of Patent: January 15, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Peter Blickle, Klaus Hintzer, Werner Schwertfeger, Heinz Strutz
  • Patent number: 4973740
    Abstract: A process for producing a tricyclodecanecarboxylic acid ester by reacting dihydrodicyclopentadiene with CO and an alcohol in the presence of anhydrous HF is disclosed. The reaction is performed in a solvent at a temperature of from -20.degree. to 60.degree. C. under a CO partial pressure of from 5 to 50 atm. The alcohol is used in an amount of 0.7 to 5 moles per mole of the dihydrodicyclopentadiene. The anhydrous HF is used in an amount of at least 5 moles per mole of the dihydrodicyclopentadiene. The product tricyclodecanecarboxylic acid ester is useful as a flavor.
    Type: Grant
    Filed: September 28, 1989
    Date of Patent: November 27, 1990
    Assignees: Mitsubishi Gas Chemical Co., Inc., Kao Corporation
    Inventors: Masami Ishihara, Takeshi Morokuma
  • Patent number: 4973749
    Abstract: A process for the preparation of the dimer of hexafluoropropene oxide (HFPO), in which the HFPO is dimerized in an aprotic polar solvent in the presence of a catalyst mixture, is described. The catalyst mixture is composed of a metal salt of the elements of the 1st transition metal series of the periodic table and of a tertiary diamine. By bringing in a molar ratio of metal salt to tertiary diamine in the range from 2:1 to 1:2, in particular 1:1, the selectivity for the dimeric compound is greatest, with high yields of the dimer being obtained.
    Type: Grant
    Filed: January 11, 1990
    Date of Patent: November 27, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Gunter Siegemund, Manfred Finke
  • Patent number: 4973748
    Abstract: A process for the preparation of perfluorinated carbonyl fluorides from hexafluoropropene oxide (HFPO) is described, in which HFPO is oligomerized in an aprotic polar solvent in the presence of a tertiary diamine in the absence or presence of at least one protonic compound. Preferably employed are tetraalkyl-substituted tertiary aliphatic diamine compounds. Protonic compounds which are possibly and preferably used are water, methanol, glycol, ammonia or diethylamine. The selectivity can be displaced in favor of shorter-chain oligomers, in particular of the dimer, by an increased content of these compounds.
    Type: Grant
    Filed: January 11, 1990
    Date of Patent: November 27, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Heinz Strutz
  • Patent number: 4962232
    Abstract: Catalytic process for the manufacture of acid fluoride selected from isobutyryl fluoride, methyl-2 butyryl fluoride, and pivaloyl fluoride from carbon monoxide, hydrogen fluoride, and an aliphatic hydrocarbon stream comprising principally an alkane having 3 to 4 carbon atoms, comprising the following series of stages:(a) introduction of at least one fluid chosen from carbon monoxide and the hydrocarbon stream into a reactor in the presence of a superacidic catalyst system comprising hydrogen fluoride, antimony pentafluoride, and at least one compound chosen from bromine, iodine, bromides, and iodides,(b) where appropriate, if it has not already been introduced during stage (a), introduction into the reactor of a fluid chosen from carbon monoxide and the hydrocarbon stream, under conditions that are suitable to permit the formation, principally, of a complex consisting of the alkyloxocarbonium cation and the anion SbF.sub.6.sup.
    Type: Grant
    Filed: November 13, 1987
    Date of Patent: October 9, 1990
    Assignee: Societe Chimique des Charbonnages, S.A.
    Inventors: Serge Delavarenne, Michel Fauconet, Michel Simon, Jean Sommer
  • Patent number: 4894484
    Abstract: A method of breaking down perfluoropolyethers into lower molecular weight fragments by pyrolysis is disclosed. The perfluoropolyethers are pyrolyzed generally at above about 350.degree. C. Volatile lower molecular weight components are condensed and collected. Various molecular weight fractions can be obtained by taking appropriate distillation cuts.
    Type: Grant
    Filed: September 3, 1987
    Date of Patent: January 16, 1990
    Assignee: Exfluor Research Corporation
    Inventors: Richard J. Lagow, Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu M. Kawa
  • Patent number: 4874557
    Abstract: The invention relates to a process for the preparation of perfluorinated carbonyl fluorides of the formula ##STR1## by oligomerization of hexafluoropropene oxide in the presence of a catalyst. The catalyst comprises a mixture of an alkali metal fluoride, a carboxylic acid dinitrile and a polyethylene glycol dimethyl ether.
    Type: Grant
    Filed: November 3, 1988
    Date of Patent: October 17, 1989
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Alfred Kruse, Gunter Siegemund, Werner Schwertfeger