Processes For Forming The Carbonyl Group Patents (Class 562/851)
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Patent number: 8513458Abstract: 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: GrantFiled: September 26, 2006Date of Patent: August 20, 2013Assignee: Nat'l Institute of Advanced Industrial Science and TechnologyInventors: Heng-dao Quan, Masanori Tamura, Akira Sekiya
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Patent number: 8394989Abstract: Provided are fluorinated oxy-carboxylic acids, derivatives of oxy-carboxylic acids, and methods of preparing oxy-carboxylic acids and derivatives thereof.Type: GrantFiled: September 26, 2008Date of Patent: March 12, 2013Assignee: 3M Innovative Properties CompanyInventors: Werner Schwertfeger, Klaus Hintzer, Egon Obermaier
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Publication number: 20130018201Abstract: 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: ApplicationFiled: July 5, 2012Publication date: January 17, 2013Inventors: 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
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Publication number: 20110251427Abstract: 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: ApplicationFiled: July 17, 2007Publication date: October 13, 2011Applicant: Nippon Mektron, LimitedInventors: Daisuke Murai, Takashi Enokida, Seiichiro Murata
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Patent number: 7880039Abstract: 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: GrantFiled: February 9, 2005Date of Patent: February 1, 2011Assignee: Solvay Fluor GmbHInventors: Max Braun, Johannes Eicher
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Publication number: 20100191013Abstract: 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: ApplicationFiled: September 26, 2006Publication date: July 29, 2010Applicant: NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGYInventors: Heng-dao Quan, Masanori Tamura, Akira Sekiya
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Patent number: 7592484Abstract: 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: GrantFiled: April 26, 2005Date of Patent: September 22, 2009Assignee: Daikin Industries, Ltd.Inventors: Seiji Takubo, Takuji Kume, Akinori Yamamoto, Chie Sawauchi, Hisako Nakamura
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Patent number: 7083705Abstract: 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: GrantFiled: August 11, 2004Date of Patent: August 1, 2006Assignee: Asahi Glass Company, LimitedInventors: Takashi Okazoe, Kunio Watanabe, Shin Tatematsu, Hidenobu Murofushi
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Patent number: 6919480Abstract: The present invention provides novel processes for preparing a fluorinated acyl fluoride and a fluorinated vinyl ether.Type: GrantFiled: December 5, 2003Date of Patent: July 19, 2005Assignee: Asahi Glass Company, LimitedInventors: Takashi Okazoe, Kunio Watanabe, Masahiro Ito, Daisuke Shirakawa, Shin Tatematsu
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Publication number: 20040147779Abstract: 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: ApplicationFiled: January 12, 2004Publication date: July 29, 2004Applicant: Baxter International IncInventors: Leonid A. Rozov, Ralph A. Lessor
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Publication number: 20040147778Abstract: A process for the synthesis of (per)fluorinated mono-functional carbonyl compounds having the following formula (I):Type: ApplicationFiled: January 9, 2004Publication date: July 29, 2004Applicant: SOLVAY SOLEXIS S.p.A.Inventors: Giovanni Fontana, Walter Navarrini
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Patent number: 6747174Abstract: The present invention provides novel processes for preparing a fluorinated acyl fluoride and a fluorinated vinyl ether.Type: GrantFiled: January 28, 2003Date of Patent: June 8, 2004Assignee: Asahi Glass Company, LimitedInventors: Takashi Okazoe, Kunio Watanabe, Masahiro Ito, Daisuke Shirakawa, Shin Tatematsu
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Publication number: 20030236436Abstract: A process for preparing acylfluorides by reaction of carbonyl fluoride COF2 with compounds having general formula:Type: ApplicationFiled: June 16, 2003Publication date: December 25, 2003Applicant: SOLVAY SOLEXIS S.p.A.Inventors: Marco Galimberti, Walter Navarrini
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Patent number: 6586626Abstract: 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: GrantFiled: September 24, 2001Date of Patent: July 1, 2003Assignee: Asahi Glass Company, LimitedInventors: Takashi Okazoe, Kunio Watanabe, Shin Tatematsu, Hidenobu Murofushi
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Patent number: 6023002Abstract: 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: GrantFiled: January 26, 1998Date of Patent: February 8, 2000Assignee: 3M Innovative Properties CompanyInventors: Frederick E. Behr, Yuri Cheburkov
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Patent number: 6002055Abstract: Highly fluorinated epoxides are reacted with dihalogens in the presence of metal and metal containing reaction promoters to give dihalofluoromethanes and their homologues.Type: GrantFiled: August 19, 1998Date of Patent: December 14, 1999Assignee: E. I. du Pont de Nemours and CompanyInventor: Zhen-Yu Yang
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Patent number: 5905169Abstract: 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: GrantFiled: March 20, 1995Date of Patent: May 18, 1999Assignee: E. I. Du Pont De Nemours and CompanyInventor: Stephen Ernest Jacobson
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Patent number: 5712418Abstract: 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: GrantFiled: August 2, 1994Date of Patent: January 27, 1998Assignee: Research Corporation Technologies, Inc.Inventors: Louis A. Carpino, Ayman Ahmed El-Faham
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Patent number: 5684193Abstract: 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: GrantFiled: November 12, 1996Date of Patent: November 4, 1997Assignee: Hoechst AktiengesellschaftInventors: Gunter Siegemund, Raimund Franz
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Patent number: 5616794Abstract: 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: GrantFiled: November 17, 1995Date of Patent: April 1, 1997Assignee: Minnesota Mining and Manufacturing CompanyInventors: Frederick E. Behr, Yuri Cheburkov
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Patent number: 5569782Abstract: 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: GrantFiled: December 20, 1994Date of Patent: October 29, 1996Assignee: Solvay Fluor und Derivate GmbHInventors: Max Braun, Werner Rudolph, Kerstin Eichholz
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Patent number: 5557010Abstract: 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: GrantFiled: June 25, 1992Date of Patent: September 17, 1996Assignee: The Dow Chemical CompanyInventors: Kevin P. Darst, Bobby R. Ezzell, Nobuyuki Ishibe
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Patent number: 5504248Abstract: 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: GrantFiled: July 28, 1994Date of Patent: April 2, 1996Assignee: E. I. Du Pont de Nemours and CompanyInventors: Paul J. Krusic, Zhen-Yu Yang
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Patent number: 5449825Abstract: 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: GrantFiled: January 18, 1994Date of Patent: September 12, 1995Assignee: The Dow Chemical CompanyInventors: Nobuyuki Ishibe, Tien K. Tran, Charles W. Martin
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Patent number: 5414119Abstract: 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: GrantFiled: March 1, 1994Date of Patent: May 9, 1995Assignee: Shin Etsu Chemical Co., Ltd.Inventors: Yasuo Tarumi, Noriyuki Koike, Toshio Takago
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Patent number: 5399754Abstract: 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: GrantFiled: April 26, 1994Date of Patent: March 21, 1995Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Masayuki Oyama, Kazutoshi Munezawa, Hitoshi Kinami
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Patent number: 5241115Abstract: A method for the preparation of carbonyl difluoride which comprises contacting carbonyl chloride fluoride with an active carbon catalyst.Type: GrantFiled: March 10, 1989Date of Patent: August 31, 1993Assignee: Imperial Chemical Industries PLCInventors: David Ashton, Thomas A. Ryan
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Patent number: 5208373Abstract: 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: GrantFiled: February 12, 1992Date of Patent: May 4, 1993Assignee: Hoechst AktiengesellschaftInventor: Matthias Meyer
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Patent number: 5093523Abstract: 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: GrantFiled: April 26, 1990Date of Patent: March 3, 1992Assignee: Ausimont S.r.l.Inventor: Claudio Gervasutti
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Patent number: 5093522Abstract: 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: GrantFiled: September 12, 1990Date of Patent: March 3, 1992Assignee: Bayer AktiengesellschaftInventors: Dietmar Bielefeldt, Heinz Ziemann
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Patent number: 5087748Abstract: 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: GrantFiled: January 11, 1990Date of Patent: February 11, 1992Assignee: Hoechst AktiengesellschaftInventors: Manfred Finke, Gunter Siegemund, Heinz Strutz
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Patent number: 5047584Abstract: 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: GrantFiled: December 9, 1985Date of Patent: September 10, 1991Assignee: Occidental Chemical Corp.Inventors: James J. Maul, Byron R. Cotter
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Patent number: 5025105Abstract: 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: GrantFiled: June 27, 1990Date of Patent: June 18, 1991Assignee: AUSIMONT S.r.l.Inventors: Silvana Modena, Ezio Strepparola
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Patent number: 5025093Abstract: 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: GrantFiled: January 5, 1990Date of Patent: June 18, 1991Assignee: Exfluor Research CorporationInventors: Richard J. Lagow, Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu M. Kawa
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Patent number: 4987254Abstract: 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: GrantFiled: August 3, 1989Date of Patent: January 22, 1991Assignee: Hoechst AktiengesellschaftInventors: Werner Schwertfeger, Klaus Hintzer, Peter Blickle
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Patent number: 4985594Abstract: 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: GrantFiled: August 3, 1989Date of Patent: January 15, 1991Assignee: Hoechst AktiengesellschaftInventors: Peter Blickle, Klaus Hintzer, Werner Schwertfeger, Heinz Strutz
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Patent number: 4973749Abstract: 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: GrantFiled: January 11, 1990Date of Patent: November 27, 1990Assignee: Hoechst AktiengesellschaftInventors: Gunter Siegemund, Manfred Finke
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Patent number: 4973740Abstract: 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: GrantFiled: September 28, 1989Date of Patent: November 27, 1990Assignees: Mitsubishi Gas Chemical Co., Inc., Kao CorporationInventors: Masami Ishihara, Takeshi Morokuma
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Patent number: 4973748Abstract: 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: GrantFiled: January 11, 1990Date of Patent: November 27, 1990Assignee: Hoechst AktiengesellschaftInventor: Heinz Strutz
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Patent number: 4962232Abstract: 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: GrantFiled: November 13, 1987Date of Patent: October 9, 1990Assignee: Societe Chimique des Charbonnages, S.A.Inventors: Serge Delavarenne, Michel Fauconet, Michel Simon, Jean Sommer
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Patent number: 4894484Abstract: 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: GrantFiled: September 3, 1987Date of Patent: January 16, 1990Assignee: Exfluor Research CorporationInventors: Richard J. Lagow, Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu M. Kawa
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Patent number: 4874557Abstract: 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: GrantFiled: November 3, 1988Date of Patent: October 17, 1989Assignee: Hoechst AktiengesellschaftInventors: Alfred Kruse, Gunter Siegemund, Werner Schwertfeger