Forming The Carbonyl To Halide Bond Patents (Class 562/861)
  • Patent number: 10730819
    Abstract: A naphthalenedicarboxylic acid dichloride production method includes causing a reaction between naphthalenedicarboxylic acid and a chlorinating agent at a reaction temperature of 20° C. or higher and 75° C. or lower in presence of a solvent including tetrahydrofuran. The causing a reaction in the naphthalenedicarboxylic acid dichloride production method is preferably performed in presence of N,N-disubstituted formamide.
    Type: Grant
    Filed: September 18, 2019
    Date of Patent: August 4, 2020
    Assignee: KYOCERA Document Solutions Inc.
    Inventor: Jun Azuma
  • Patent number: 8993819
    Abstract: The present invention provides a process for preparing cycloheptene and derivatives thereof by ring-closing metathesis of unsymmetric 1,8-dienes whose C—C double bond at the 8 position is nonterminal. Cycloheptene and the cycloheptanone, cycloheptylamine, cycloheptanecarbaldehyde, cycloheptanecarboxylic acid and cycloheptanecarbonyl chloride conversion products thereof, and the derivatives thereof, are important synthesis units for active ingredient compounds. The ring-closing metathesis is preferably performed as a reactive distillation. The unsymmetric 1,8-dienes for the ring-closing metathesis can be obtained by catalytic decarbonylation or oxidative decarboxylation from the corresponding unsaturated carboxylic acids or carboxylic acid derivatives.
    Type: Grant
    Filed: July 10, 2012
    Date of Patent: March 31, 2015
    Assignee: BASF SE
    Inventors: Joaquim Henrique Teles, Michael Limbach, Richard Dehn, Stephan Deuerlein, Manuel Danz
  • 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
  • Patent number: 8785689
    Abstract: A method for purifying difluoroacetic acid chloride, including the step of bringing a difluoroacetic acid chloride composition that contains at least difluoroacetic acid fluoride into contact with calcium chloride at a temperature enabling reaction thereof thereby converting difluoroacetic acid fluoride into difluoroacetic acid chloride.
    Type: Grant
    Filed: March 28, 2012
    Date of Patent: July 22, 2014
    Assignee: Central Glass Company, Limited
    Inventors: Naoto Takada, Masamune Okamoto, Hideaki Imura
  • Patent number: 8642805
    Abstract: A method of producing a phthaloyl dichloride compound, the method including: providing a compound represented by the following formula (1) and a compound represented by the following formula (2); and bringing the compound represented by the following formula (1) and the compound represented by the following formula (2) into reaction, so as to form a compound represented by the following formula (3), in the presence of at least one compound selected from a zirconium compound, a hafnium compound, and zinc oxide; wherein, in formulae, X represents a hydrogen atom, a halogen atom, a nitro group, a methyl group, or a methoxy group; when the X is plural, Xs may be the same or different from each other; n represents an integer of from 0 to 2; R represents a halogen atom, a chlorocarbonyl group, a low carbon number alkyl group, or a halogen-substituted low carbon number alkyl group; when the R is plural, Rs may be the same or different from each other; and m represents an integer of from 0 to 2.
    Type: Grant
    Filed: July 27, 2009
    Date of Patent: February 4, 2014
    Assignees: Iharanikkei Chemical Industry Co., Ltd., Nippon Light Metal Company, Ltd.
    Inventors: Yoshikazu Kimura, Yoshihiro Takao, Toshimitsu Sugiyama, Takeshi Hanawa, Hiromichi Ito
  • Publication number: 20140031588
    Abstract: A method for purifying difluoroacetic acid chloride, including the step of bringing a difluoroacetic acid chloride composition that contains at least difluoroacetic acid fluoride into contact with calcium chloride at a temperature enabling reaction thereof thereby converting difluoroacetic acid fluoride into difluoroacetic acid chloride.
    Type: Application
    Filed: March 28, 2012
    Publication date: January 30, 2014
    Applicant: Central Glass Campany, Limited
    Inventors: Naoto Takada, Masamune Okamoto, Hideaki Imura
  • 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.
  • Publication number: 20130018205
    Abstract: The present invention provides a process for preparing cycloheptene and derivatives thereof by ring-closing metathesis of unsymmetric 1,8-dienes whose C—C double bond at the 8 position is nonterminal. Cycloheptene and the cycloheptanone, cycloheptylamine, cycloheptanecarbaldehyde, cycloheptanecarboxylic acid and cycloheptanecarbonyl chloride conversion products thereof, and the derivatives thereof, are important synthesis units for active ingredient compounds. The ring-closing metathesis is preferably performed as a reactive distillation. The unsymmetric 1,8-dienes for the ring-closing metathesis can be obtained by catalytic decarbonylation or oxidative decarboxylation from the corresponding unsaturated carboxylic acids or carboxylic acid derivatives.
    Type: Application
    Filed: July 10, 2012
    Publication date: January 17, 2013
    Applicant: BASF SE
    Inventors: Joaquim Henrique TELES, Michael Limbach, Richard Dehn, Stephan Deuerlein, Manuel Danz
  • Publication number: 20130012740
    Abstract: A production method of difluoroacetyl chloride according to the present invention includes a chlorination step of bringing a raw material containing at least either a 1-alkoxy-1,1,2,2-tetrafluoroethane or difluoroacetyl chloride into contact with calcium chloride at a reaction enabling temperature. A production method of 2,2-difluoroethyl alcohol according to the present invention includes a catalytic reduction step of causing catalytic reduction of the difluoroacetyl chloride obtained by the above production method. By these methods, the difluoroacetyl fluoride can be efficiently converted to the difluoroacetyl chloride and to the 2,2-difluoroethyl alcohol.
    Type: Application
    Filed: March 16, 2011
    Publication date: January 10, 2013
    Applicant: Central Glass Company ,Limited
    Inventors: Masamune Okamoto, Hideaki Imura, Naoto Takada
  • Patent number: 8198482
    Abstract: This invention relates to a method for producing a carboxylic acid chloride, which efficiently decomposes a Vilsmeier reagent type compound in a carboxylic acid chloride lacking a thermal stability or a carboxylic acid chloride hardly distilled in practice due to a high boiling point with a simple operation and has no adverse effect on a subsequent step, and more particularly to a method for producing a carboxylic acid chloride, characterized by comprising reacting a carboxylic acid with a chlorinating agent in the presence of a catalyst, removing the excessive chlorinating agent from a reaction system after the reaction, and then further adding 1.0 to 3.0 equivalents of the starting carboxylic acid based on the catalyst to the reaction system to decompose a Vilsmeier reagent type compound remaining in the reaction system.
    Type: Grant
    Filed: February 27, 2008
    Date of Patent: June 12, 2012
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Takeshi Kobayashi, Kiyomi Kido, Akinori Nagatomo
  • Patent number: 8153801
    Abstract: The invention provides synthetic processes and synthetic intermediates that can be used to prepare 4-oxoquinolone compounds having useful integrase inhibiting properties.
    Type: Grant
    Filed: September 11, 2008
    Date of Patent: April 10, 2012
    Assignee: Gilead Sciences, Inc.
    Inventors: Eric Dowdy, Steven Pfeiffer
  • Publication number: 20110282070
    Abstract: A benzoylpyrazole compound represented by the formula (I) or its salt: wherein R1 is alkyl or cycloalkyl, R2 is a hydrogen atom or alkyl, R3 is alkyl; cycloalkyl; haloalkyl; alkoxyalkyl; alkoxycarbonylalkyl; alkenyl; or arylalkyl which may be substituted by R8, R4 is alkyl; haloalkyl; alkoxy; halogen; nitro; cyano; alkylthio; alkylsulfinyl; or alkylsulfonyl, R5 is a hydrogen atom; alkyl; alkenyl; alkynyl; halogen; cyano; cyanoalkyl; cyanoalkeny; haloalkyl; alkoxyalkyl; haloalkoxyalkyl; amino(thiocarbonyl)alkyl which may be substituted by at least one substituent selected from alkyl, cyano, is cyanoalkyl, (alkylthio)carbonylalkyl, alkyl(thiocarbonyl)alkyl, —C(O)OR7 and —C(O)SR7; thiocyanatoalkyl; alkoxy; alkenyloxy; alkynyloxy; haloalkoxy; alkoxyalkoxy; haloalkoxyalkoxy; alkoxyhaloalkoxy; haloalkoxyhaloalkoxy; alkoxyalkoxyalkyl; alkylthio; alkoxyalkylthio; haloalkoxyalkylthio; alkoxyhaloalkylthio; haloalkoxyhaloalkylthio; alkylthioalkylthio; haloalkylthioalkylthio; alkylthiohaloalkylthio; haloalkylthiohalo
    Type: Application
    Filed: July 21, 2011
    Publication date: November 17, 2011
    Applicant: ISHIHARA SANGYO KAISHA, LTD.
    Inventors: Hiroshi SHIMOHARADA, Masamitsu Tsukamoto, Masahiko Ikeguchi, Hiroshi Kikugawa, Makiko Sano, Yoshinori Kitahara, Hidemasa Kominami, Tatsuya Okita
  • Publication number: 20100292480
    Abstract: The invention provides synthetic processes and synthetic intermediates that can be used to prepare 4-oxoquinolone compounds having useful integrase inhibiting properties.
    Type: Application
    Filed: September 11, 2008
    Publication date: November 18, 2010
    Applicant: Gilead Sciences, Inc
    Inventors: Eric Dowdy, Steven Pfeiffer
  • Publication number: 20100185013
    Abstract: A process for forming an ?,?-unsaturated carbonyl halide in a microreactor is described. The reactants comprise an ?,?-unsaturated carboxylic acid, a halogenating agent, and a catalyst. A first inlet stream, a second inlet stream, and an optional third inlet stream flow into a reaction chamber of a flow-through microreactor to form a reaction product comprising an ?,?-unsaturated carbonyl halide.
    Type: Application
    Filed: June 4, 2008
    Publication date: July 22, 2010
    Inventors: Matthew J. Pinnow, Eric R. Choban, Kim M. Vogel
  • Publication number: 20100099911
    Abstract: This invention relates to a method for producing a carboxylic acid chloride, which efficiently decomposes a Vilsmeier reagent type compound in a carboxylic acid chloride lacking a thermal stability or a carboxylic acid chloride hardly distilled in practice due to a high boiling point with a simple operation and has no adverse effect on a subsequent step, and more particularly to a method for producing a carboxylic acid chloride, characterized by comprising reacting a carboxylic acid with a chlorinating agent in the presence of a catalyst, removing the excessive chlorinating agent from a reaction system after the reaction, and then further adding 1.0 to 3.0 equivalents of the starting carboxylic acid based on the catalyst to the reaction system to decompose a Vilsmeier reagent type compound remaining in the reaction system.
    Type: Application
    Filed: February 27, 2008
    Publication date: April 22, 2010
    Applicant: Mitsui Chemicals, Inc
    Inventors: Takeshi Kobayashi, Kiyomi Kido, Akinori Nagatomo
  • Publication number: 20090312569
    Abstract: The present invention relates to a process for the preparation of 1-(2-ethyl-butyl)-cyclohexanecarboxylic acid which is useful as an intermediate in the preparation of pharmaceutically active compounds.
    Type: Application
    Filed: June 12, 2009
    Publication date: December 17, 2009
    Inventor: Bruno Lohri
  • Publication number: 20090076304
    Abstract: The present invention discloses methods for producing a carboxylic acid chloride compound which comprises the step of reacting an alkyl-substituted cyclohexyl carboxylic acid with a chlorinating agent in the presence of a specific urea compound. According to this invention, it is possible to produce a carboxylic acid chloride compound which has high reaction speed, and whose product has high purity or high yield. Thus produced carboxylic acid chloride compound is useful as an intermediate for producing D-phenylalanine derivatives which are used as agents for treating diabetes.
    Type: Application
    Filed: September 30, 2008
    Publication date: March 19, 2009
    Applicant: AJINOMOTO CO., INC.
    Inventors: Tatsuya Ishikawa, Shouichi Kondou, Satoji Takahashi
  • 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: 7034181
    Abstract: The invention relates to a method for producing o-chloromethyl benzoic acid chlorides of formula (I), in which R1 to R4 can be the same or different and represent hydrogen C1–C4 alkyl, halogen or trifluoromethyl, by reaction benzo condensed lactones of formula (II), in which R1 to R4 have the above-mentioned meaning, with thionyl chloride. The inventive method is characterized in that the reaction is carried out in the presence of catalytic quantities of a Lewis acid and in the presence of catalytic quantities of a phosphine derivative.
    Type: Grant
    Filed: November 27, 2000
    Date of Patent: April 25, 2006
    Assignee: BASF Aktiengesellschaft
    Inventors: Roland Götz, Norbert Götz, Michael Keil, Bernd Wolf, Adrian Steinmetz, Armin Stamm, Jochem Henkelmann
  • 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
  • Publication number: 20040171849
    Abstract: The present invention provides an efficient, simple, and commercially advantageous process for producing optically active azetidine-2-carboxylic acid, which is an important material for medicines.
    Type: Application
    Filed: January 14, 2004
    Publication date: September 2, 2004
    Inventors: Takeshi Kondo, Noboru Ueyama
  • Publication number: 20040024250
    Abstract: A perfluoropolyether and a composition comprising the perfluoropolyether are provided in which the perfluoropolyether comprises at least one bromine or iodine atom at the primary position of the perfluoropolyether. Also provided is a process for producing the composition in which the process comprises contacting a perfluoropolyether acid fluoride moiety with a metal bromide or metal iodide or a suitable polyether secondary iodide under a condition sufficient to effect the production of a perfluoropolyether comprising at least one bromine or iodine at the primary position.
    Type: Application
    Filed: July 25, 2003
    Publication date: February 5, 2004
    Inventors: Jon L. Howell, Erik W. Perez, Alfred Waterfeld, Chadron Mark Friesen, Joseph Stuart Thrasher, Ireneusz Nowak
  • 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: 6605743
    Abstract: The invention relates to a continuous process for the preparation of pivaloyl chloride and of aroyl chloride, in particular of benzoyl chloride, which consists in reacting pivalic acid with a trichloromethylated aromatic compound in the presence of a catalyst at a temperature of between 60° C. and 180° C. under reduced pressure. The products formed are continuously removed from the reaction region, the hydrogen chloride formed being treated in a washing region in which a trichloromethylated compound moves countercurrentwise.
    Type: Grant
    Filed: December 23, 1998
    Date of Patent: August 12, 2003
    Assignee: Elf Atochem S.A.
    Inventors: Christophe Ruppin, Philippe Corbiere
  • Publication number: 20030130537
    Abstract: The present invention relates to a process for preparing substituted benzoyl chlorides of the formula (1) 1
    Type: Application
    Filed: October 3, 2002
    Publication date: July 10, 2003
    Applicant: Clariant GmbH
    Inventors: Lars Bierer, Joachim Ritzer, Berthold Schiemenz, Thomas Wessel
  • 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: 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
  • Publication number: 20020040158
    Abstract: The present invention relates to a process for preparing substituted benzoyl chlorides of the formula (1) 1
    Type: Application
    Filed: July 26, 2001
    Publication date: April 4, 2002
    Applicant: Clariant GmbH
    Inventors: Lars Bierer, Joachim Ritzer, Berthold Schiemenz, Thomas Wessel
  • Patent number: 6329529
    Abstract: Disclosed are a fluorinating agent represented by the general formula (1): wherein R1 to R4 are a substituted or unsubstituted, saturated or unsaturated alkyl group or a substituted or unsubstituted aryl group, and can be the same or different; R1 and R2 or R3 and R4 can bond to form a ring including a nitrogen atom or a nitrogen atom and other hetero atoms; or R1 and R3 can bond to form a ring including a nitrogen atom or a nitrogen atom and other hetero atoms, for example: a preparation process of the fluorinating agent and a process for preparing fluorine compounds by reacting various compounds with the fluorinating agent. The invention has also disclosed that the fluorinating agent is very effective for fluorinating oxygen containing functional compounds.
    Type: Grant
    Filed: July 31, 1998
    Date of Patent: December 11, 2001
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Hiroshi Sonoda, Kazunari Okada, Akira Takahashi, Kouki Fukumura, Hidetoshi Hayashi, Teruyuki Nagata, Yasuhiro Takano
  • Patent number: 6313337
    Abstract: A method of making a benzoyl halide is disclosed. Into a reactor is placed a reaction mixture of a benzotrihalide and a benzaldehyde having the respective general formulas where each A is independently selected from halogen, CF3, R, or OR, each B is independently selected from halogen, CF3, or R, R is alkyl from C1 to C10 or aryl from C6 to C12, each X is independently selected from Cl and Br, m is 0 to 3, and n is 0 to 2. Also added is at least about 10 ppm of a catalyst selected from the group consisting of zinc salts and copper salts, and an optional solvent. The addition of an ammonium halide to the product mixture forms the corresponding amide, which can be dehydrated to form the corresponding nitrile.
    Type: Grant
    Filed: April 17, 2000
    Date of Patent: November 6, 2001
    Assignee: Occidental Chemical Corporation
    Inventors: Dean R. Lagerwall, Daniel R. Thielen, Pravin M. Khandare, Mark F. Lechner
  • Patent number: 6201152
    Abstract: Disclosed is a method of making 3,5-dichloro-p-toluoyl chloride. A mixture is prepared of methyl-3,5-dichloro-4-methylbenzoate, about 1 to about 1.4 equivalents of an &agr;,&agr;,&agr;-trichloromethylbenzene, and about 0.01 to about 0.2 equivalents of a catalyst selected from the group consisting of ammonium septamolybdate, ammonium dimolybdate, and mixtures thereof. The mixture is heated to a temperature of about 150 to about 180° C.
    Type: Grant
    Filed: November 5, 1999
    Date of Patent: March 13, 2001
    Assignee: Occidental Chemical Corporation
    Inventors: Michael J. Fifolt, Sanjay Mandal, William S. Derwin
  • Patent number: 5945565
    Abstract: Novel routes for the preparation of acetonylbenzamides are provided by the reaction of an amine and acyl chloride. Novel routes to various intermediates used in the manufacture of acetonylbenzamides are also disclosed.
    Type: Grant
    Filed: October 22, 1998
    Date of Patent: August 31, 1999
    Assignee: Rohm and Haas Company
    Inventors: Enrique Luis Michelotti, Heather Lynnette Rayle, Randall Wayne Stephens, William Joseph Zabrodski
  • 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: 5919341
    Abstract: A process for preparing chlorodifluoroacetyl chloride from 1,1-difluoro-2,2-dichloroethylene and dichloroacetyl chloride from trichloroethylene or 1,1,2,2-tetrachloroethane, in which the starting compounds are continuously reacted in the gaseous phase with oxygen to obtain a photochemical oxidation reaction, chlorine being added as a sensitizer, the reaction mixture being irradiated with light having a wavelength .lambda..gtoreq.280 nm, the reaction preferably being carried out unpressurized. Particularly high yields with height selectivity are achieved by using doped high pressure mercury vapor lamps to irradiate the reaction mixture.
    Type: Grant
    Filed: December 23, 1997
    Date of Patent: July 6, 1999
    Assignee: Solvay Fluor und Derivate GmbH
    Inventors: Max Braun, Werner Rudolph, Kerstin Eichholz
  • Patent number: 5912371
    Abstract: A method for preparing fatty acid chlorides. The method comprises reacting a silylation product of a fatty acid comprising at 1east 2 aliphatically unsaturated bonds per molecule and a chlorinating agent.
    Type: Grant
    Filed: October 27, 1997
    Date of Patent: June 15, 1999
    Assignee: Dow Corning Toray Silicone Co., Ltd.
    Inventors: Koji Nakanishi, Tadashi Okawa
  • 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: 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: 5623082
    Abstract: Acyl chlorides are prepared by reacting a carboxylic acid or its anhydride with carbonyl chloride in the presence of a carboxamide of the formula I ##STR1## where R.sup.1 is a radical of the formula ##STR2## R.sup.2 and R.sup.3 are each alkyl of 1 to 9 carbon atoms, R.sup.4 and R.sup.5 are each hydrogen or alkyl of 1 to 9 carbon atoms and the two radicals R.sup.1 and R.sup.2 may furthermore be a hydrocarbon radical which completes the moiety ##STR3## to form a heterocyclic structure, and the stated alkyl and hydrocarbon radicals may furthermore contain substituents which are inert under the reaction conditions.
    Type: Grant
    Filed: July 11, 1995
    Date of Patent: April 22, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Martin Decker, Wolfgang Franzischka, Rudolf Irnich, deceased, Manfred Sauerwald
  • Patent number: 5616787
    Abstract: The invention relates to a process for the preparation of polyalkylated aromatic carboxylic acids of formula I ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are each independently of one another hydrogen, C.sub.1 -C.sub.20 alkyl, halogen or C.sub.5 -C.sub.8 cycloalkyl, with the proviso that at least two of the substituents R.sub.1, R.sub.2, R.sub.3, R.sub.4 or R.sub.5 are alkyl and/or cycloalkyl, by reacting corresponding aromatic hydrocarbons with carbon dioxide, which reaction is carried out observing special ratios of temperature and pressure. The invention furthermore relates to a one-pot process for the preparation of the corresponding acyl halides.
    Type: Grant
    Filed: October 11, 1995
    Date of Patent: April 1, 1997
    Assignee: Ciba-Geigy Corporation
    Inventors: Rinaldo Husler, Ivan Orban, Martin Holer
  • Patent number: 5543568
    Abstract: A process for the preparation of .alpha.,.beta.-unsaturated .beta.-oxycarboxylic acid chlorides of the formula I ##STR1## where R.sup.1 is a C-organic radical, and R.sup.2 and R.sup.3, independently of one another, are hydrogen or a C-organic radical, comprises carrying out the addition reaction of an enol derivative of the formula II ##STR2## with a compound of the formula IIIa, IIIb or IIIc ##STR3## and converting the resultant acid chloride of the formula ##STR4## into I by elimination of hydrogen chloride (HCl).
    Type: Grant
    Filed: September 7, 1993
    Date of Patent: August 6, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Jochem Henkelmann, Lutz Tietze
  • Patent number: 5532411
    Abstract: A process for preparing carboxylic acid halides and carboxylate salts by reacting metal or "onium" halides with carboxylic anhydrides, which process is very suitable for working-up anhydrous, spent catalyst preparations. The resulting carboxylic acid halide or carboxylate salt can be used as an acylating reagent or alkylating reagent, and metal halide or "onium" halide liberated during this can be reacted anew with carboxylic anhydride and regenerated, thereby making it possible to effect a hydrolysis-free alkylation or acylation without forming salt-type waste products. If the mixture of carboxylic acid halide and carboxylate salt is allowed to react with an alcohol, preferably in situ, the resulting ester can be isolated without hydrolysis.
    Type: Grant
    Filed: April 26, 1994
    Date of Patent: July 2, 1996
    Assignee: Solvay Fluor und Derivate GmbH
    Inventors: Max Braun, Werner Rudolph, Stefan Palsherm, 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: 5504245
    Abstract: Disclosed is a process for the preparation of cyclopropanecarboxylic acid by the non-catalytic, oxidation of cyclopropanecarboxaldehyde using molecular oxygen as the oxidant. Also disclosed are processes for the preparation of amides, esters and acid chlorides from cyclopropanecarboxylic acid.
    Type: Grant
    Filed: September 30, 1994
    Date of Patent: April 2, 1996
    Assignee: Eastman Chemical Company
    Inventors: Shaowo Liang, Timothy W. Price
  • Patent number: 5504249
    Abstract: A process for preparing o-chloromethylbenzoyl chlorides of the formula I ##STR1## where m is 0 or an integer from 1 to 4 andX is halogen or C-organic radicals,entails reacting a corresponding lactone of the formula II ##STR2## with thionyl chloride in the presence of a catalyst.
    Type: Grant
    Filed: March 31, 1995
    Date of Patent: April 2, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Heinz Isak, Herbert Bayer, Michael Keil, Thomas Wettling
  • Patent number: 5493054
    Abstract: The subject of the present invention is a new catalytic system and a process for the synthesis of acid halides, especially from haloforms. This process for halogenating by means of a haloform is characterized by the use of a metal chloride, advantageously trivalent, as a catalyst, the solubility of which in the reaction mixture is at least equal to one millimole, preferably 1/100 mole per liter, and the metal chloride also being at least half, advantageously two-thirds and preferably three-quarters in the dissolved state.
    Type: Grant
    Filed: September 27, 1994
    Date of Patent: February 20, 1996
    Assignee: Rhone-Poulenc Chimie
    Inventors: Gerard Forat, Laurent Gilbert
  • 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: 5395966
    Abstract: Acryloyl chloride is obtained by reaction of acrylic acid with phenylchloroform in the presence of at least one Lewis acid as catalyst and of at least one polymerization inhibitor. According to the invention the catalyst is chosen from zinc oxide and zirconium tetrachloride and the reaction is conducted at a temperature of at least 105.degree. C. In a preferred embodiment acrylic acid is added to the mixture consisting of phenylchloroform, the catalyst and the polymerization inhibitor and heated to a temperature of at least 105.degree. C., the acryloyl chloride formed distilling off as soon as the introduction of acrylic acid begins.Acryloyl chloride is a highly reactive synthesis intermediate.
    Type: Grant
    Filed: July 22, 1994
    Date of Patent: March 7, 1995
    Assignee: Atochem
    Inventors: Jean-Francois Croizy, Paul Grosius
  • 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: 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