Elemental Halogen Or Hydrogen Halide Utilized Patents (Class 562/863)
  • Patent number: 8455684
    Abstract: A method for converting an aromatic aldehyde or a mixture of aromatic aldehydes to a reaction product in a reaction medium that is free from xylene. The reaction product may be an aromatic acyl halide or a mixture of aromatic acyl halides. The method includes bringing the aromatic aldehyde or mixture of aromatic aldehydes in contact with a halogen to obtain the reaction product.
    Type: Grant
    Filed: March 10, 2010
    Date of Patent: June 4, 2013
    Assignee: Teijin Aramid B.V.
    Inventors: Hendrikus Bekx, Henk Knoester
  • Patent number: 8350082
    Abstract: This process for producing fluorine-containing compounds includes liquid-phase fluorination by introducing a raw material compound and fluorine gas into a solvent to replace hydrogen atoms in the raw material compound with fluorine atoms. More specifically, the process for producing fluorine-containing compounds includes (1) promoting fluorination by dissolving the raw material compound in anhydrous hydrofluoric acid and introducing into a liquid-phase fluorination solvent, or (2) promoting fluorination by dissolving the raw material compound in a perfluoro compound having a plurality of polar groups in a molecule thereof and introducing into a liquid-phase fluorination solvent. According to these processes, a fluorination reaction can be carried out at high yield and without containing hardly any isomers while using a hydrocarbon compound as is for the raw material.
    Type: Grant
    Filed: November 28, 2008
    Date of Patent: January 8, 2013
    Assignees: Mitsubishi Materials Corporation, Mitsubishi Materials Electronic Chemicals Co., Ltd.
    Inventors: Mitsuo Kurumaya, Tsunetoshi Honda, Kota Omori
  • 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
  • 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: 6951957
    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: April 24, 2003
    Date of Patent: October 4, 2005
    Assignee: Asahi Glass Company, Limited
    Inventors: Takashi Okazoe, Kunio Watanabe, Shin Tatematsu, Hidenobu Murofushi
  • Patent number: 6844468
    Abstract: The present invention relates to a process for preparing substituted benzoyl chlorides of the formula (1) where R, x and y have the meaning given below, which comprises reacting a benzaldehyde of the formula (2) where R, independently of each other, is identical or different and is an unsubstituted phenyl radical or a phenyl radical that is substituted by halogen, NO2, CN, (C1-C4)alkyl or (C1-C4)alkoxy, or is halogen, NO2, CN, NR?2, OR?, SO2R?, SO2OR?, COR? or CO2R?, where R? is an unbranched or branched C1-C10 alkyl radical, an unsubstituted phenyl radical or a phenyl radical which is substituted by halogen, NO2, CN, (C1-C4)alkyl or (C1-C4)alkoxy, x is 1 or 2 and y is 1, 2 or 3, with a chlorinating agent in the presence of a free-radical initiator and a solvent at from ?20 to +200° C.
    Type: Grant
    Filed: October 3, 2002
    Date of Patent: January 18, 2005
    Assignee: Clariant GmbH
    Inventors: Lars Bierer, Joachim Ritzer, Berthold Schiemenz, Thomas Wessel
  • Patent number: 6833477
    Abstract: The process for producing a vic-dichloro acid fluoride compound in a short process and in good yield from the starting material which is inexpensive and readily available is provided. (RH1—EH1—)CRH2RH3CH2—OCORHB (I) is fluorinated in a liquid phase to form (CF2ClCFCl—EFF1—) CRF2RF3CF2—OCORFB (II), and then, an ester bond of the compound (II) is decomposed to form (CF2ClCFCl—EF1—)CRF2RF3COF(III) or the compound (III) and FCORFB (IV).
    Type: Grant
    Filed: February 28, 2002
    Date of Patent: December 21, 2004
    Assignee: Asahi Glass Company, Limited
    Inventors: Takashi Okazoe, Kunio Watanabe, Masahiro Ito, Daisuke Shirakawa, Shin Tatematsu
  • Patent number: 6677479
    Abstract: Compounds of the formula (I) and also process for preparing them where substituents X1, X2, Y and Z are defined as follows: X1 is H or F X2 is H or F Y is CI, Br, or I Z is CHO or COOH or CN n is 0 or 1 and also their use as starting material for preparing agrochemicals, electronics materials and pharmaceuticals.
    Type: Grant
    Filed: November 12, 2002
    Date of Patent: January 13, 2004
    Assignee: Clariant Finance LBVI Limited
    Inventors: Wolfgang Schmidt, Rainer Wingen
  • 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: 6255524
    Abstract: An acid chloride can be produced at a high yield from a primary alcohol having a polyfluoroalkyl group and one methylene group by (1) a method in which RfCH2OH (wherein Rf is a polyfluoroalkyl group) is reacted with chlorine to produce RfCOCl, (2) a method in which RfCHO is reacted with chlorine to produce RfCOCl, and (3) a method for producing an acid chloride comprising (a) a step in which an aldehyde (RfCHO) is formed from an alcohol (RfCH2OH), (b) a step in which a monochloroester (RfCOOCHClRf) is formed from the aldehyde and an acid chloride (RfCOCl), and (c) a step in which the acid chloride (RfCOCl) is formed from the monochloroester.
    Type: Grant
    Filed: June 25, 1999
    Date of Patent: July 3, 2001
    Assignee: Daikin Industries Ltd.
    Inventors: Hirokazu Aoyama, Shoji Takagi, Shinichi Matsumura, Yoshinori Tanaka
  • Patent number: 6187952
    Abstract: The present invention relates to a process for the preparation of 3-chloro-4-fluorobenzoyl chloride which comprises reacting 4-fluorobenzaldehyde with a chlorinating agent in the presence of a free-radical initiator in the presence or absence of a solvent at from −20 to 200° C. to give 4-fluorobenzoyl chloride, and reacting the 4-fluorobenzoyl chloride with a chlorinating agent in the presence of a chlorination catalyst in the presence or absence of a solvent at from −20 to 200° C. to give 3-chloro-4-fluorobenzoyl chloride.
    Type: Grant
    Filed: December 10, 1998
    Date of Patent: February 13, 2001
    Assignee: Clariant GmbH
    Inventors: Ralf Pfirmann, Thomas Wessel
  • Patent number: 5939581
    Abstract: Processes for preparing aromatic carboxylic acids. Cinnamaldehyde is hydrogenated to produce a mixture of hydrogenation products, namely, hydrocinnamaldehyde and hydrocinnamic alcohol. The mixture is then oxidized using a suitable oxidizing agent to substantially completely convert both hydrocinnamaldehyde and hydrocinnamic alcohol to hydrocinnamic acid.
    Type: Grant
    Filed: August 20, 1997
    Date of Patent: August 17, 1999
    Assignee: First Chemical Corporation
    Inventors: August John Muller, Joseph Stanton Bowers, Jr., John Robert Ira Eubanks, Carey Cecil Geiger, John Gabriel Santobianco
  • Patent number: 5872290
    Abstract: Disclosed is a method of making an acid chloride having the general formula ##STR1## where each R contains no unsaturated groups and is preferably independently selected from aliphatic from C.sub.1 to C.sub.7 and aryl from C.sub.6 to C.sub.15. A solution is formed in an inert solvent of an aldehyde having the general formula ##STR2## and chlorine gas is sparged into said solution. The reaction between the aldehyde and the chlorine gas to produce the acid chloride is performed in the absence of a catalyst, an initiator, and ultraviolet light. A chlorinated acid chloride can be prepared from the acid chloride by reacting it with additional chlorine in the presence of a chlorine free radical generator.
    Type: Grant
    Filed: November 7, 1997
    Date of Patent: February 16, 1999
    Assignee: Occidental Chemical Corporation
    Inventors: James G. Colson, Ramesh Krishnamurti, Rose Adinolfe
  • Patent number: 5872291
    Abstract: Provided is a process for producing benzoyl chlorides which comprises reacting an aromatic aldehyde with chlorine in liquid phase in the presence of inert gas, whereby the generation of benzal chlorides by products whose separation is difficult can be suppressed.
    Type: Grant
    Filed: December 18, 1997
    Date of Patent: February 16, 1999
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Takeshi Koshikawa, Toshihiro Hashimoto, Makoto Takagawa
  • Patent number: 5672749
    Abstract: The yield of acetyl chloride from the reaction between acetic anhydride and hydrogen chloride is increased by withdrawing acetyl chloride, optionally together with at least some of the acetic acid by-product, from the reaction mixture as the reaction proceeds and recycling the remainder of the reaction mixture to the reactor for reaction with additional hydrogen chloride.
    Type: Grant
    Filed: April 9, 1996
    Date of Patent: September 30, 1997
    Assignee: Albemarle Corporation
    Inventors: W. Bryan Waites, Robert E. Young, Phillip R. DeVrou
  • Patent number: 5599981
    Abstract: Provided is a process for producing alkylbenzoyl chloride which comprises reacting alkylbenzaldehyde with chlorine at a temperature of -10.degree. to 80.degree. C. under a pressure of 5 kg/cm.sup.2 or below in a liquid phase, whereby alkylbenzoyl chloride can be produced in a high yield and at a low price.
    Type: Grant
    Filed: January 24, 1996
    Date of Patent: February 4, 1997
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Norio Fushimi, Kenichi Nakamura, Makoto Takagawa
  • 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: 5506358
    Abstract: There is disclosed a process for producing an alkoxyiminoacetamide compound which is useful as agricultural fungicides. Also dislclosed are novel intermediate compounds for the above process and their production.
    Type: Grant
    Filed: March 8, 1994
    Date of Patent: April 9, 1996
    Assignee: Shionogi & Co., Ltd.
    Inventors: Akira Takase, Hiroyuki Kai, Moriyasu Masui, Kazuo Ueda, Tsuneo Iwakawa
  • Patent number: 5504250
    Abstract: The invention relates to a process for the preparation of D-(-)-phenylglycine chloride hydrochloride by chlorinating D-(-)-phenylglycine hydrochloride, which as such is prepared in situ from D-(-)-phenylglycine and hydrochloric acid gas, in a solvent. According to the invention chlorination of the hydrochloride is carried out in a non-chlorinated solvent or a mixture of non-chlorinated solvents in the presence of a reaction promoting medium.Chlorination is carried out through the addition of PCl.sub.5, but preferably the PCl.sub.5 is prepared in situ from PCl.sub.3 and Cl.sub.2 gas.
    Type: Grant
    Filed: February 28, 1994
    Date of Patent: April 2, 1996
    Assignee: Westpur Investments Limited
    Inventor: Raoul Kessels
  • Patent number: 5473095
    Abstract: The present invention relates to a process for the preparation of compounds of the formula ##STR1## in which R.sup.1 is --CN, --COOH, --COOR', R' being an organic radical having 1 to 6 carbon atoms, --CONH.sub.2, --COCl or --CHO and R.sup.2 is H or Cl, which comprises reacting a compound of the formula ##STR2## in which R.sup.1 is as defined above and R.sup.3 is H or Cl, with a chlorinating agent in the presence of a chlorination catalyst at -10.degree. to 200.degree. C.
    Type: Grant
    Filed: January 27, 1994
    Date of Patent: December 5, 1995
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ralf Pfirmann, Theodor Papenfuhs, Georg Weichselbaumer
  • Patent number: 5344977
    Abstract: An improved process for the preparation of 2,3-dibromopropionyl chloride, which comprises brominating acrylic acid, adding iron powder or an iron salt to the resultant melt, chlorinating the dibromopropionic acid obtained, and removing the volatile components. The 2,3-dibromopropionyl chloride is obtained in high yield and purity and is an intermediate for synthesising in particular reactive dyes.
    Type: Grant
    Filed: January 22, 1993
    Date of Patent: September 6, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Alfons Arquint, Peter Leupin
  • Patent number: 5296640
    Abstract: A process for preparing perhaloacyl chlorides such as trifluoroacetyl chloride by oxidizing lower perfluoroalkyl and monochloroperfluoroalkyl dichloromethane within the supercritical region and in the absence of water.
    Type: Grant
    Filed: September 15, 1992
    Date of Patent: March 22, 1994
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Stephen E. Jacobson, Wayne B. Ely
  • Patent number: 5037512
    Abstract: A process for the purification of crude benzoic acid obtained by the catalytic oxidation of toluene in the liquid phase, which is contaminated with impurities including phthalic acid and benzylbenzoate, the process involves distilling the crude benzoic acid in a first distillation in the presence of an aliphatic amine or a mixture of aliphatic amines of the formulaHNR.sup.1 R.sup.2whereinR.sup.1 represents hydrogen or a straight-chain or branched hydroxyalkyl or aminoalkyl radical with 1 to 6 carbon atoms andR.sup.2 represents a straight-chain or branched hydroxyalkyl or aminoalkyl radical with 1 to 6 carbon atoms,and/or the salts of these amines, recovering from this distillation (a) a purified benzoic acid and (b) a benzylbenzoate containing residue, working up the residue by a second distillation and chlorinating the distillate resulting from this second distillation to give a benzoylchloride virtually free of benzonitrile.
    Type: Grant
    Filed: August 17, 1989
    Date of Patent: August 6, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventor: Werner Schulte-Huermann
  • Patent number: 4990661
    Abstract: A process for the preparation of a compound of the formula ##STR1## in which X.sup.1 and X.sup.2 each independently is chlorine or fluorine, andY is chlorine, bromine, fluorine or iodine, comprising subjecting a compound of the formula ##STR2## to a Sandmeyer or Balz-Schiemann reaction thereby to produce a carboxylic acid of the formula ##STR3## and converting the carboxylic acid (Ia) into an acyl chloride of the formula ##STR4## The compound (II) is new. The products are known intermediates for anti-bacterials.
    Type: Grant
    Filed: March 29, 1989
    Date of Patent: February 5, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Uwe Petersen, Michael Schriewer, Ernst Kysela, Klaus Grohe
  • Patent number: 4968852
    Abstract: A novel compound, trifluoromethylbenzoyl bromide, is formed by bromination of trifluoromethylbenzoic acid with, e.g., phosphorus tribromide or by halogen exchange reaction of trifluoromethylbenzoyl chloride with bromine in the presence of a metal bromide. Decarbonylation of 2-, 3- or 4-trifluoromethylbenozyl bromide using a catalyst such as a phosphine-rhodium complex gives 2-, 3- or 4-bromobenzotrifluoride without forming isomers.
    Type: Grant
    Filed: December 28, 1989
    Date of Patent: November 6, 1990
    Assignee: Central Glass Company, Limited
    Inventors: Toshikazu Kawai, Hideki Oshio
  • Patent number: 4851160
    Abstract: A process for the preparation of a compound of the formula ##STR1## in which X.sup.1 and X.sup.2 each independently is chlorine or fluorine, andY is chlorine, bromine, fluorine or iodine, comprising subjecting a compound of the formula ##STR2## to a Sandmeyer or Balz-Schiemann reaction thereby to produce a carboxylic acid of the formula ##STR3## and converting the carboxylic acid (Ia) into an acyl chloride of the formula ##STR4## The compound (II) is new. The products are known intermediates for anti-bacterials.
    Type: Grant
    Filed: August 28, 1987
    Date of Patent: July 25, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Uwe Petersen, Michael Schriewer, Ernst Kysela, Klaus Grohe