Processes For Forming The Carbonyl To Fluoride Bond Patents (Class 562/852)
  • Patent number: 9099605
    Abstract: The fabrication and characterization of large scale inverted organic solar array fabricated using all-spray process is disclosed, consisting of four layers; ITO-Cs2CO3-(P3HT:PCBM)-modified PEDPT:PSS, on a substrate. With PEDPT:PSS as the anode, the encapsulated solar array shows more than 30% transmission in the visible to near IR range. Optimization by thermal annealing was performed based on single-cell or multiple-cell arrays. Solar illumination has been demonstrated to improve solar array efficiency up to 250% with device efficiency of 1.80% under AM1.5 irradiance. The performance enhancement under illumination occurs only with sprayed devices, indicating device enhancement under sunlight, which is beneficial for solar energy applications.
    Type: Grant
    Filed: May 31, 2013
    Date of Patent: August 4, 2015
    Assignee: University of South Florida
    Inventors: Xiaomei Jane Jiang, Jason Erik Lewis
  • Publication number: 20140336403
    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 25, 2014
    Publication date: November 13, 2014
    Inventors: Gerard John Harnett, John Hayes, Reinhard Reents, Dennis A. Smith, Andrew Walsh
  • Publication number: 20140312276
    Abstract: This invention relates to liquid crystal compound of formula I containing a difluoromethyleneoxy linking group that hydrogen substituted by deuterium and therefore being very suitable for formulating a liquid crystal mixture. A liquid crystal mixture containing such type of liquid crystal compounds can be applied in various display devices.
    Type: Application
    Filed: July 3, 2014
    Publication date: October 23, 2014
    Inventors: Wen Hai LU, Ze Feng HOU, Xing ZHANG, Guo Liang YUN, Rui Mao HUA, Jin WANG, Ya Jie DUAN
  • Patent number: 8829236
    Abstract: The present invention relates to a method for preparing a halogenoacetyl fluoride and the derivatives thereof. The inventive method for preparing a halogenoacetyl fluoride acid is characterized in that said method includes: a step of preparing a halogenoacetyl halide by photo-oxidation of a halogenoethylene compound in conditions such that the transformation rate of the halogenoethylene compound into halogenoacetyl halide is no higher than 80%, producing a reaction mixture essentially including halogenoacetyl halide and the excess halogenoethylene compound; a step of partial fluorination of the mixture obtained by reacting the latter with hydrofluoric acid suitable for obtaining a mixture of halogenoacetyl fluoride and the excess halogenoethylene compound; a step of separating the halogenoacetyl fluoride and the excess halogenoethylene compound. The invention can be used, specifically, for preparing the trichloroacetyl fluoride used as an intermediate species in the production of trifluoroacetic acid.
    Type: Grant
    Filed: July 7, 2010
    Date of Patent: September 9, 2014
    Assignee: Rhodia Operations
    Inventors: Laurent Saint-Jalmes, Francois Metz
  • Patent number: 8664438
    Abstract: An object of the invention is to provide efficient, simple and inexpensive processes for the production of carbonyl difluoride, which is an attractive and important compound as a semiconductor etching gas or a semiconductor cleaning gas. A process for producing carbonyl difluoride of the invention includes a step of reacting phosgene and hydrogen fluoride in a gas phase in the presence of a fluorination catalyst to produce carbonyl difluoride and hydrogen chloride, and a step of mixing a mixture containing the carbonyl difluoride and the hydrogen chloride with an organic solvent that is azeotropic with hydrogen chloride but zeotropic with carbonyl difluoride, and distilling the resultant mixture to separate the carbonyl difluoride.
    Type: Grant
    Filed: October 2, 2009
    Date of Patent: March 4, 2014
    Assignee: Showa Denko K.K.
    Inventors: Hiromoto Ohno, Toshio Ohi, Hidejiro Yokoo
  • Publication number: 20130245289
    Abstract: A process for producing a perfluorinated functional compound comprises the steps of: A) converting an at least partially hydrogenated alcohol into an at least partially hydrogenated ester compound; and B) reacting said at least partially hydrogenated ester compound with fluorine in the presence of at least one (per)haloolefin comprising at least one carbon-carbon double bond and having at least one fluorine or chlorine atom on either one of the carbon atoms of said double bond, to obtain a perfluorinated ester compound.
    Type: Application
    Filed: November 17, 2011
    Publication date: September 19, 2013
    Applicant: SOLVAY SPECIALTY POLYMERS ITALY S.P.A.
    Inventors: Vito Tortelli, Marco Galimberti
  • Publication number: 20130197257
    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: March 14, 2013
    Publication date: August 1, 2013
    Applicant: Hoffmann-La Roche Inc.
    Inventor: Hoffmann-La Roche Inc.
  • Patent number: 8299300
    Abstract: The invention relates to a method for preparing difluoroacetic acid and the salts thereof. The invention also relates to the preparation of difluoroacetyl fluoride used as an intermediate product in the preparation of difluoroacetic acid. The method for preparing difluoroacetic acid according to the invention is characterized in that the same comprises the step of preparing difluoroacetyl fluoride by reacting dichloroacetyl chloride with hydrofluoric acid in a gaseous phase and in the presence of a chromium-based catalyst, followed by the step of hydrolysing the difluoroacetyl fluoride thus obtained.
    Type: Grant
    Filed: March 9, 2009
    Date of Patent: October 30, 2012
    Assignee: Rhodia Operations
    Inventors: François Metz, Laurent Saint-Jalmes
  • Patent number: 8232416
    Abstract: A method of manufacturing a compound represented by formula (2) is provided, the method including thermally decomposing a compound represented by formula (1) under a reduced pressure: wherein Rf1 and Rf2 each independently represents a fluorine atom or a perfluorinated monovalent substituent, Rf3 and Rf4 each independently represents a fluorine atom, a perfluorinated monovalent substituent or a perfluorinated divalent substituent, Rf3 and Rf4 may combine with each other to form a ring, each of Rf3 and Rf4 may combine with Rf5 to form a ring, and Rf5 represents a perfluorinated (n+1)-valent to (2n+2)-valent linkage group, provided that n represents an integer of 1 to 5.
    Type: Grant
    Filed: February 25, 2009
    Date of Patent: July 31, 2012
    Assignee: FUJIFILM Corporation
    Inventors: Hiroki Sugiura, Masayuki Harada
  • Publication number: 20120108801
    Abstract: The invention relates to disubstituted-aminodifluorosulfinium salts represented by the formula (I). Processes for preparing same and methods of use as deoxofluorinating reagent is also provided.
    Type: Application
    Filed: June 18, 2010
    Publication date: May 3, 2012
    Applicant: OMEGACHEM INC
    Inventors: Michel A. Couturier, Alexandre L'Heureux
  • Publication number: 20110184209
    Abstract: An object of the invention is to provide efficient, simple and inexpensive processes for the production of carbonyl difluoride, which is an attractive and important compound as a semiconductor etching gas or a semiconductor cleaning gas. A process for producing carbonyl difluoride of the invention includes a step of reacting phosgene and hydrogen fluoride in a gas phase in the presence of a fluorination catalyst to produce carbonyl difluoride and hydrogen chloride, and a step of mixing a mixture containing the carbonyl difluoride and the hydrogen chloride with an organic solvent that is azeotropic with hydrogen chloride but zeotropic with carbonyl difluoride, and distilling the resultant mixture to separate the carbonyl difluoride.
    Type: Application
    Filed: October 2, 2009
    Publication date: July 28, 2011
    Applicant: SHOWA DENKO K.K.
    Inventors: Hiromoto Ohno, Toshio Ohi, Hidejiro Yokoo
  • Patent number: 7807858
    Abstract: It was found that a fluoro derivative can be produced by reacting a hydroxy derivative with sulfuryl fluoride (SO2F2) in the presence of an organic base or in the presence of an organic base and “a salt or complex comprising an organic base and hydrogen fluoride”. According to the present production process, it is not necessary to use perfluoroalkanesulfonyl fluoride, which is not preferable in industrial use, and it is possible to advantageously produce optically-active fluoro derivatives, which are important intermediates of medicines, agricultural chemicals and optical materials, specifically 4-fluoroproline derivatives, 2?-deoxy-2?-fluorouridine derivatives, optically-active ?-fluorocarboxylate derivatives, and the like, even in a large scale.
    Type: Grant
    Filed: March 17, 2006
    Date of Patent: October 5, 2010
    Assignee: Central Glass Company, Limited
    Inventors: Akihiro Ishii, Takashi Ootsuka, Manabu Yasumoto, Hideyuki Tsuruta, Kenjin Inomiya, Koji Ueda, Kaori Mogi
  • Patent number: 7507866
    Abstract: The present invention relates to a process for preparing optically active hydroxy-, alkoxy-, amino-, alkyl-, aryl- or chlorine-substituted alcohols or hydroxy carboxylic acids having from 3 to 25 carbon atoms or their acid derivatives or cyclization products by hydrogenating the correspondingly substituted optically active mono- or dicarboxylic acids or their acid derivatives in the presence of a catalyst whose active component consists of rhenium or of rhenium and comprises at least one further element having an atomic number of from 22 to 83, with the provisos that a. the at least one further element having an atomic number of from 22 to 83 is not ruthenium and b.
    Type: Grant
    Filed: February 8, 2005
    Date of Patent: March 24, 2009
    Assignee: BASF AG
    Inventors: Heiko Urtel, Markus Rösch, Andrea Haunert, Markus Schubert
  • Patent number: 7425646
    Abstract: A compound represented by the formula AF(—COF)n, provided that AF and n have the following meanings. AF: a fluorinated adamantane residue which is an n-valent group having an n number of hydrogen atoms removed from adamantane (provided that when n is at least 2, the removed hydrogen atoms are hydrogen atoms bonded to different carbon atoms), wherein at least one of the remaining hydrogen atoms is substituted by a fluorine atom, and the remaining hydrogen atoms may be substituted by a C1-6 alkyl group or fluoroalkyl group, and n: an integer of from 1 to 4, provided the when n is 1, AF has at least one hydrogen atom.
    Type: Grant
    Filed: December 15, 2006
    Date of Patent: September 16, 2008
    Assignee: Asahi Glass Company, Limited
    Inventors: Kazuya Oharu, Takashi Okazoe, Eisuke Murotani, Kunio Watanabe, Masahiro Ito
  • Patent number: 7375253
    Abstract: A process for the synthesis of (per)fluorinated mono-functional carbonyl compounds having the following formula (I): F-A-RF—B—C(O)X1??(I) wherein: X1=F, CF3; A, B equal to or different from each other, are independently (per)fluoroalkylene or (per)fluorooxyalkylene groups; RF is —ORf1O— wherein Rf1=perfluoroalkylene or —ORf2, wherein Rf2 is a perfluorooxyalkylene chain; said process comprising the following steps: A) obtainment of the formula (II) mono-hypofluorite: FO—CFX2-A-RF—B—C(O)X1??(II) by partial fluorination with elemental fluorine of the carbonyl groups of the formula (III) compound: X2(O)C-A-RF—B—C(O)X1??(III) in the presence of a formula MeFy catalyst, Me being an alkaline or alkaline-earth metal or Ag, y=1 or 2; B) thermal decomposition of the compound (II) to give the compounds according to the following scheme: FO—CFX2-A-RF—B—C(O)X1 (II) - - - ?F-A-RF—B—C(O)X1 (I)+(O)CFX2.
    Type: Grant
    Filed: January 9, 2004
    Date of Patent: May 20, 2008
    Assignee: Solvay Solexis S.p.A.
    Inventors: Giovanni Fontana, Walter Navarrini
  • Patent number: 7371898
    Abstract: A method for producing carbonyl fluoride by continuously supplying carbon monoxide and fluorine into a reaction chamber together with a diluent gas and letting them react with each other, where hydrogen fluoride or carbonyl fluoride is used as the diluent gas.
    Type: Grant
    Filed: June 9, 2006
    Date of Patent: May 13, 2008
    Assignee: Asahi Glass Company, Limited
    Inventor: Yuki Mitsui
  • Patent number: 7371899
    Abstract: To provide a method for producing carbonyl fluoride by employing carbon monoxide and fluorine as starting materials, without such a problem as vigorous heat generation or a decrease in the reaction yield due to a side reaction.
    Type: Grant
    Filed: June 15, 2007
    Date of Patent: May 13, 2008
    Assignee: Asahi Glass Company, Limited
    Inventors: Yuuki Mitsui, Koichi Yanase
  • 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: 7071272
    Abstract: The present invention provides a method for preparing a compound of CF3CF2CF2OCF?CF2 by pyrolyzing a compound expressed by CF3CF2CF2OCF(CF3)COOCF2CF(CF3)OCF2CF2CF3 in a gas phase at a temperature of from 200° C. to 500° C.
    Type: Grant
    Filed: December 2, 2002
    Date of Patent: July 4, 2006
    Assignee: Asahi Glass Company, Limited
    Inventors: Takashi Okazoe, Kunio Watanabe, Shin Tatematsu, Masakuni Sato, Hidenobu Murofushi, Koichi Yanase, Yasuhiro Suzuki
  • Patent number: 6969776
    Abstract: The present invention provides a process whereby fluorinated ketones of various structures can be produced by short process steps and which is useful as an industrial production process.
    Type: Grant
    Filed: June 17, 2004
    Date of Patent: November 29, 2005
    Assignee: Asahi Glass Company, Limited
    Inventors: Takashi Okazoe, Kunio Watanabe, Masahiro Ito, Daisuke Shirakawa, Shin Tatematsu, Hirokazu Takagi
  • Patent number: 6956138
    Abstract: The present invention provides a method for obtaining a compound useful as a raw material for various fluororesins in high yield by a short process by using a starting material which is inexpensive and readily available.
    Type: Grant
    Filed: April 28, 2004
    Date of Patent: October 18, 2005
    Assignee: Asahi Glass Company, Limited
    Inventors: Takashi Okazoe, Kunio Watanabe, Shin Tatematsu, Masahiro Ito, Daisuke Shirakawa, Masao Iwaya, Hidekazu Okamoto
  • 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
  • Patent number: 6803488
    Abstract: The present invention provides a process whereby fluorinated ketones of various structures can be produced by short process steps and which is useful as an industrial production process.
    Type: Grant
    Filed: February 26, 2003
    Date of Patent: October 12, 2004
    Assignee: Asahi Glass Company, Limited
    Inventors: Takashi Okazoe, Kunio Watanabe, Masahiro Ito, Daisuke Shirakawa, Shin Tatematsu, Hirokazu Takagi
  • Publication number: 20040147780
    Abstract: A process for the synthesis of (per)fluorinated mono-functional carbonyl compounds having the following formula:
    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
  • Patent number: 6723874
    Abstract: Acid fluorides, for example carboxylic acid fluorides and sulfuryl fluoride are produced by reacting the corresponding acid chlorides with hydrogen fluoride adducts of ammonium fluoride or amine hydrofluorides (which act as a catalyst or as a fluorination agent). Consumed HF adducts may be regenerated with HF.
    Type: Grant
    Filed: May 30, 2001
    Date of Patent: April 20, 2004
    Assignee: Solvay Fluor und Derivate GmbH
    Inventors: Max Braun, Matthias Rieland, Francine Janssens, Kerstin Eichholz, Stefan Palsherm
  • Publication number: 20030171616
    Abstract: A process for efficiently producing an acyl fluoride and a carboxylic acid salt while inhibiting side reactions.
    Type: Application
    Filed: March 27, 2003
    Publication date: September 11, 2003
    Applicant: ASAHI GLASS COMPANY LIMITED
    Inventors: Kunio Watanabe, Takashi Okazoe, Masahiro Ito, Shin Tatematsu, Hiroki Kamiya, Eisuke Murotani
  • Patent number: 6613929
    Abstract: A process for the preparation of fluoroformates of the formula wherein R1 is a saturated or unsaturated, substituted or unsubstituted and primary or secondary aliphatic, a saturated or unsaturated, substituted or unsubstituted secondary cycloaliphatic or a substituted or unsubstituted aromatic or heteroaromatic, and n is equal to 1, 2 or 3, comprising reacting a corresponding chloroformate of formula I with an alkali metal fluoride in ethylene carbonate at a temperature wherein the ethylene carbonate is liquid whereby it is possible to very rapidly obtain the fluoroformates with excellent yields and high purity.
    Type: Grant
    Filed: December 18, 2002
    Date of Patent: September 2, 2003
    Assignee: Isochem
    Inventors: Alphonse Alarcon-Lorca, Thierry Malfroot, Jean-Pierre Senet
  • 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
  • Publication number: 20020147364
    Abstract: Active fluoride catalysts that are useful in producing electrophilic fluorination agents; especially useful in producing BDM from the reaction of fluorine with carbon dioxide and FTM from the reaction of fluorine with carbonyl fluoride. The fluoride catalyst comprises a mixture of two or more fluorides selected from a transition metal fluoride, an alkali metal fluoride and/or an alkaline earth metal fluoride. Alternately, the fluoride catalyst is one or more fluorides, such as alkali metal fluorides, alkaline earth metal fluorides, and/or transition metal fluorides, deposited on an inert support.
    Type: Application
    Filed: February 15, 2001
    Publication date: October 10, 2002
    Inventors: Robert George Syvret, Philip Bruce Henderson, Donald Elson Fowler, Beth Ann Campion, Frederick Carl Wilhelm
  • Patent number: 6420601
    Abstract: 3,5-Bis(trifluoromethyl)benzoyl chlorides optionally substituted with fluorine or chlorine are advantageously prepared by converting 3,5-dimethylbenzoic acids optionally substituted with fluorine or chlorine into the corresponding acid chlorides; completely free-radically chlorinating said chlorides in the side chains, giving 3,5-bis(trichloromethyl)benzoyl chlorides optionally substituted by fluorine or chlorine; fluorinating the latter with anhydrous hydrogen fluoride and/or antimony pentafluoride, giving 3,5-bis(trifluoromethyl)benzoyl fluorides optionally substituted with fluorine or chlorine; and then reacting the 3,5-bis(trifluoromethyl)benzoyl fluorides with silicon tetrachloride in the presence of a further Lewis acid. Some of the 3,5-bis(trihalogenomethyl) and 3,5-dimethylbenzoyl halides which arise as intermediates are novel compounds.
    Type: Grant
    Filed: January 25, 2001
    Date of Patent: July 16, 2002
    Assignee: Bayer Aktiengesellschaft
    Inventors: Albrecht Marhold, Jörn Stölting
  • Patent number: 6166252
    Abstract: Process for preparing dichlorofluoroacetylfluoride (CFCl.sub.2 COF) comprising the following steps:a) fluorination with hydrofluoric acid (HF) of the trichloroacetyl halide in a fixed or fluidized tubular bed reactor, filled with fluorination catalysts and having a temperature profile between the inlet of the reactants and the outlet of the reaction products, in the range from 175.degree. C. to 275.degree. C.b) distillation of the reaction products with trichloroacetylfluoride recycle and recovery of a mixture formed by HF and CFCl.sub.2 COF;c) separation of the HF/CFCl.sub.2 COF mixture components by cooling at temperatures lower than -10.degree. C., and optionally the HF recycle.
    Type: Grant
    Filed: January 7, 1999
    Date of Patent: December 26, 2000
    Assignee: Ausimont S.p.A.
    Inventors: Piero Gavezotti, Julio A. Abusleme, Vito Tortelli
  • 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: 5780672
    Abstract: A process for the preparation of compounds of the formula (1) in which R.sup.1, R.sup.2 and R.sup.3 are as defined in the specification, which includes reacting alcohols or carboxylic acids of the formula (2) in which R.sup.1, R.sup.2 and R.sup.3 are as defined in the specification, with a fluorinating agent of the formula (3) as defined in the specification.
    Type: Grant
    Filed: July 11, 1996
    Date of Patent: July 14, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Sergej Pasenok, Wolfgang Appel
  • Patent number: 5750779
    Abstract: A preparation process of acyl halide or sulfonyl halide which comprises reacting corresponding carboxylic acid or sulfonic acid with a haloiminium salt represented by the general formula (1): ##STR1## wherein R.sup.1 and R.sup.2 are same or different lower alkyl groups, X is a halogen atom, and n is an integer of 2 or 3.
    Type: Grant
    Filed: May 31, 1996
    Date of Patent: May 12, 1998
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Teruyuki Nagata, Hidetoshi Hayashi, Hideki Mizuta
  • 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: 5672748
    Abstract: The invention relates to the preparation of trifluoroacetyl fluoride by reacting trichloroacetyl chloride with anhydrous hydrogen fluoride in the gaseous phase on a catalyst which is obtainable by reacting a water-soluble chromium (III) salt with magnesium hydroxide or magnesium oxide in the presence of water, converting the reaction mixture into a paste, drying the paste and treating it with hydrogen fluoride.
    Type: Grant
    Filed: June 29, 1995
    Date of Patent: September 30, 1997
    Assignee: Solvay
    Inventors: Frank Ebmeyer, Tobias Metzenthin, Gunter Siegemund
  • Patent number: 5648530
    Abstract: Carbonyl fluoride is produced by reacting fluorine-containing compound such as metal fluoride with CO in an excited state, such as produced by a plasma, to obtain a gaseous reaction mixture, which can then be quenched to obtain the COF.sub.2.
    Type: Grant
    Filed: December 18, 1995
    Date of Patent: July 15, 1997
    Inventor: James Lang Webster
  • Patent number: 5633399
    Abstract: A process for the preparation of 2-chloro-4,5-difluorobenzoic acid and 2,4,5-trifluorobenzoic acid as well as synthetic intermediates useful in and prepared according thereto, comprising reacting a nitrobenzene having the formula ##STR1## wherein X is chloro or fluoro, with an appropriate carbanion to form a compound having the formula ##STR2## wherein one of Y and Z is chloro and the other is nitro, and R is a radical selected from the group consisting of --CCl.sub.3, --CH.sub.2 NO.sub.2, --CH(NO.sub.2)R.sup.1, --CH(CO.sub.2 R.sup.1).sub.2, --CH(C(O)R.sup.2).sub.2, --CH(CN)CO.sub.2 R.sup.1, --CH(CO.sub.2 R.sup.1)COR.sup.2 and --COR.sup.2 where R.sup.1 is alkyl or arylalkyl and R.sup.2 is alkyl, aryl or arylalkyl and, where appearing more than once in such a radical, R.sup.1 and R.sup.2 may be the same or different at each occurrence.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: May 27, 1997
    Assignee: Abbott Laboratories
    Inventors: Xiu C. Wang, Panos Kalaritis, Michelle L. Chang
  • 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: 5466877
    Abstract: A process for converting perfluorinated carboxylic acid esters to perfluorinated acyl fluorides and/or perfluorinated ketones comprises the step of combining at least one perfluorinated carboxylic acid ester with at least one initiating reagent selected from the group consisting of gaseous, non-hydroxylic nucleophiles; liquid, non-hydroxylic nucleophiles; and mixtures of at least one non-hydroxylic nucleophile (gaseous, liquid, or solid) and at least one solvent which is inert to acylating agents. The process enables the dissociation of even high molecular weight, perfluorinated esters.
    Type: Grant
    Filed: March 15, 1994
    Date of Patent: November 14, 1995
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: George G. I. Moore
  • Patent number: 5362909
    Abstract: 2,4,5-Trihalogenobenzene derivatives of the formula ##STR1## in which R is --COOH, --COCl, --COF, --CN, --CONH.sub.2, --CH.sub.2 OH, --CH.sub.2 Cl, --CHCl.sub.2, --CCl.sub.3 or --CHO,R.sup.1 is H, Cl or F, andR.sup.2 is Cl or F,it only being possible for R.sup.1 or R.sup.2 to be F, and processes for their preparation starting from benzonitriles reacted with potassium fluoride. The novel compounds are intermediates for antibacterials such as quinolone carboxylic acids.
    Type: Grant
    Filed: October 29, 1992
    Date of Patent: November 8, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Erich Klauke, Uwe Petersen, Klaus Grohe
  • 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: 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: 4985556
    Abstract: Perfluorocarboxylic acid fluorides represented by the formula A-B, wherein A is either ##STR1## and B stands for a perfluoro-di-substituted amino group, and perfluoro(dialkylaminopropenes) represented by the formula A"-B", wherein A" stands for ##STR2## and B" has the same meaning as B defined above, are novel compounds. Methods for the production of these novel compounds are also disclosed.
    Type: Grant
    Filed: September 9, 1988
    Date of Patent: January 15, 1991
    Assignees: Agency of Industrial Science & Technology, Ministry of International Trade & Industry
    Inventors: Takashi Abe, Eiji Hayashi
  • 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