Preparation By Halogenating Acid Or Anhydride Patents (Class 562/603)
  • Patent number: 9187400
    Abstract: The present invention pertains to a process for separating monochloroacetic acid and dichloroacetic acid from one another via extractive distillation using (a) an extractive agent that is chemically stable and has a BF3 affinity of between 65 kJ/mole and 110 kJ/mole and (b) an organic solvent that is either an acid with a lowest pKa of between 3.0 and 6.
    Type: Grant
    Filed: April 3, 2013
    Date of Patent: November 17, 2015
    Assignee: AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
    Inventors: Johannes Jozef Pragt, Mark Theodorus Gerardus Jongmans, Gerrald Bargeman, Boelo Schuur, Jacobus Theodorus Josef Aaldering, Melle Rinze Nieuwhof, Anton Alexandru Kiss, André Banier De Haan, Alex Londoño Rodriguez, Cornelis Johannes Govardus Van Strien
  • Patent number: 9073848
    Abstract: The present invention pertains to a process for separating monochloroacetic acid and dichloroacetic acid from one another via extractive distillation, comprising the steps of (i) contacting a mixture comprising monochloroacetic acid and dichloroacetic acid with an extractive agent which is chemically stable and which has a BF3 affinity of between 65 kJ/mole and 110 kJ/mole, (ii) distilling the mixture to obtain a monochloroacetic acid stream and a stream comprising dichloroacetic acid and the extractive agent, and (iii) regenerating the extractive agent.
    Type: Grant
    Filed: March 13, 2012
    Date of Patent: July 7, 2015
    Assignee: AKZO NOBEL CHEMICALS INTERNATIONAL B.V.
    Inventors: Mark Theodorus Gerardus Jongmans, Johannes Josef Pragt, Gerrald Bargeman, Boelo Schuur, Jacobus Theodorus Josef Aaldering, André Banier De Haan, Melle Rinze Nieuwhof, Paul Verwer, Anton Alexandru Kiss, Antoon Jacob Berend Ten Kate, Cornelis Johannes Govardus Van Strien
  • Publication number: 20140148603
    Abstract: A method for preparing a fluorinated organic compound (II) from an organic compound (I) comprising at least one nucleofugal group Nu, and also a preparation of different specific organic compounds, in particular a fluoro-methylpyrazole compound. The method comprises: a reaction, in the presence of water, of the organic compound (I) and at least one salt providing at least one fluoride anion; and a replacement of at least one nucleofugal group Nu of the compound (I) with a fluorine atom, in order to obtain the fluorinated organic compound (II).
    Type: Application
    Filed: May 29, 2012
    Publication date: May 29, 2014
    Applicant: RHODIA OPERATIONS
    Inventors: Olivier Buisine, Michael Dejoux
  • Publication number: 20130184469
    Abstract: The invention relates to a novel, industrially viable, cost effective process for the preparation of 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide commonly known as Rufinamide and intermediates thereof.
    Type: Application
    Filed: August 23, 2011
    Publication date: July 18, 2013
    Inventors: Ramamohan Rao Davuluri, Ravi Ponnaiah, Sanjay Kumar Dehury, Selvaraju K., Deepthi VPSS, Dhanunjaya Naidu
  • Publication number: 20130131375
    Abstract: A process for preparing difluoroacetic acid, salts thereof or esters thereof is described. The process can further include preparation of difluoroacetic acid, salts thereof or esters thereof, wherein the reaction occurs in the presence of water of a salt providing a fluoride anion and of monohalogenated or dihalogenated acetic acid, in acid, salified or esterified form, at least one halogen atom being other than the fluorine atom.
    Type: Application
    Filed: July 26, 2011
    Publication date: May 23, 2013
    Applicant: RHODIA OPERATIONS
    Inventor: Olivier Buisine
  • Publication number: 20120245384
    Abstract: A method for preparing highly fluorinated carboxylic acids and theirs salts and the precursors thereof.
    Type: Application
    Filed: November 18, 2010
    Publication date: September 27, 2012
    Inventors: Klaus Hintzer, Tilman C. Zipplies, Oleg Shyshkov
  • Publication number: 20100160670
    Abstract: The present invention comprises a novel process for the preparation of a chiral compound of formula (I) wherein R1 is hydroxyl or a group which activates the carboxyl and R2 is alkyl optionally substituted by halogen or benzyl, its preparation, its application in the synthesis of chiral 2-bromomethyl-2-ethylhexanoic acid and novel intermediates.
    Type: Application
    Filed: March 4, 2010
    Publication date: June 24, 2010
    Applicant: AVENTIS PHARMA S.A.
    Inventors: Veronique Crocq-Stuerga, Patrick Roussel
  • Patent number: 7473803
    Abstract: The invention provides processes for producing efficiently optically active 2-halogenocarboxylic acids useful in the preparation of drugs or the like and salts thereof with amines. Specifically, an optically active 2-halogenocarboxylic acid is produced by halogenating an optically active amino acid in water in the presence of a hydrophobic organic solvent and nitrous acid with the configuration retained and with the racemization inhibited through the removal of 2-hydroxy-bromocarboxylic acid formed as a by-product; the obtained optically active 2-halogenocarboxylic acid is transferred to an aqueous phase by converting it into a salt thereof with a base, followed by the removal of the organic phase; and the optically active 2-halogenocarboxylic acid is transferred again to an organic solvent phase, followed by the removal of the aqueous phase, whereby an optically active 2-halogenocarboxylic acid is obtained through the removal of a halogen component.
    Type: Grant
    Filed: February 4, 2003
    Date of Patent: January 6, 2009
    Assignee: Kaneka Corporation
    Inventors: Koki Yamashita, Toshihiro Takeda, Yasuyoshi Ueda
  • Patent number: 7247736
    Abstract: The present invention provides a compound capable of binding to the ubiquinone binding site of DHODH which contains a non-aromatic ring system as a core structure, a group capable of interacting with structural elements of subsite 2 or 3 of the ubiquinone binding site of DHODH and a group capable of interacting hydrophobically with structural elements of subsite 1 of the ubiquinone binding site of DHODH. Furthermore, the present invention provides a compound capable of binding to the ubiquinone binding site of DHODH which contains an aromatic ring system as a core structure, a group capable of interacting with residues His 56 and/or Tyr 356 of subsite 3 of the ubiquinone binding site of DHODH and a group capable of interacting hydrophobically with structural elements of subsite 1 of the ubiquinone binding site of DHODH.
    Type: Grant
    Filed: November 10, 2004
    Date of Patent: July 24, 2007
    Assignee: 4SC AG
    Inventors: Johann Leban, Bernd Kramer, Roland Baumgartner, Katharina Aulinger-Fuchs, Stefan Tasler
  • Patent number: 7135597
    Abstract: The invention pertains to a process for the production of monochloroacetic acid from chlorine and acetic acid in the presence of a catalyst by reactive distillation. The process and the required reactive distillation apparatus is much less complex than conventional reactors and yields a monochloroacetic acid product having a low content of over-chlorinated products.
    Type: Grant
    Filed: October 2, 2003
    Date of Patent: November 14, 2006
    Assignee: Akzo Nobel N.V.
    Inventors: Jeroen Crouzen, Johannes Joseph Gorissen, Cornelis Johannes Govardus Van Strien
  • Patent number: 7030270
    Abstract: The invention relates to a process for preparing monochloroacetic acid (MCA) comprising a chlorination step and a hydrogenation step and is characterized in that said process comprises the removal of aldehydes from a process stream by oxidation using a peroxycarboxylic acid. A preferred peroxycarboxylic acid comprises peracetic acid. Preferably, the process is carried out at a temperature of 60–100° C., most preferably at atmospheric pressure. Preferably, an about equimolar amount of peroxycarboxylic acid is used relative to the molar amount of aldehydes present in the process stream. A practical choice for the process stream is the acetic acid recycle stream. The invention process provides a clear and colourless MCA end product.
    Type: Grant
    Filed: November 19, 2002
    Date of Patent: April 18, 2006
    Assignee: Akzo Nobel N.V.
    Inventors: Cornelis Kooijman, Jacobus Theodorus Jozef Aaldering
  • Patent number: 6846952
    Abstract: A process for producing 4-bromo-2-oxyimino butyric acid, predominantly as the (Z)-isomer of formula (I), wherein R is hydrogen; a linear or branched C1-4 alkyl group; a linear or branched C1-4 alkyl group substituted by a carboxylic acid or an aryl group; a substituted or unsubstituted cyclic alkyl group of 3-6 carbon atoms or a substituted or unsubstituted aryl group. The product is produced by reacting bromine with a 2-(oxyimino)-3-oxo butyric acid derivative of formula (II) wherein R is as defined above and R1 is a tert-butyl group in presence of an organic solvent and in presence of a C1-4 alcohol and acetyl bromide at a temperature ranging from about ?15° C. to about +15° C. Bromine is used in a proportion of about 0.90 to about 1.35 moles per mole of compound (II), preferably 0.90 to 1.10 moles. The acetyl bromide is used in molar proportions of 0.9 to 2 moles per mole of compound (II), preferably 0.9 to 1.5 moles.
    Type: Grant
    Filed: June 7, 2002
    Date of Patent: January 25, 2005
    Assignee: Lupin Limited
    Inventors: Vinod Kumar Kansal, Dnyandeo Ragho Rane, Sanjay Deshmukh, Santosh Kumar Singh, Santosh Richaria, Susan Ajay Abraham
  • Patent number: 6743929
    Abstract: Sulfonamide-containing hydroxyethylamine compounds are effecive as retroviral protease inhibitors, and in particular as inhibitors of HIV protease.
    Type: Grant
    Filed: September 6, 2000
    Date of Patent: June 1, 2004
    Assignee: G. D. Searle & Co.
    Inventors: Michael L. Vazquez, Richard A. Mueller, John J. Talley, Daniel Getman, Gary A. DeCrescenzo, John N. Freskos
  • Patent number: 6049001
    Abstract: Novel fluorine-containing carboxylic acid compounds of formula (II) are provided that can be reacted together with a base to produce industrially useful 3-(2-chloro-2-fluorovinyl)-2,2-dimethyl cyclopropanecarboxylic acid compounds of formula (I). The fluorine-containing containing carboxylic acid compounds of formula (II), if so desired, can be produced by reacting together a carboxylic acid compound of formula (III) and trichlorofluoromethane. In each of the formulas (I), (II), and (III), R is a lower alkyl group or a hydrogen atom.
    Type: Grant
    Filed: July 28, 1999
    Date of Patent: April 11, 2000
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Ken Otaka, Noritada Matsuo
  • Patent number: 5753776
    Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: May 19, 1998
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu Kawa, Richard J. Lagow
  • Patent number: 5750769
    Abstract: The invention provides novel compounds of formula:CF.sub.3 --CXCl--CH(OH)CH.sub.2 --C(CH.sub.3).sub.2 --CH.sub.2 --CO.sub.2 R(I)where X represents chloro or bromo and R represents hydrogen or alkyl of up to 4 carbon atoms, processes for preparing them and their use as intermediates in the preparation of insecticidal cyclopropane derivatives. Also provided are novel compounds of formula:BrCH.sub.2 --CH.sub.2 --C(CH.sub.3).sub.2 --CH.sub.2 --CO.sub.2 R(IV)wherein R represents alkyl of up to 4 carbon atoms, useful as intermediates in the preparation of the compounds of formula I.
    Type: Grant
    Filed: November 8, 1995
    Date of Patent: May 12, 1998
    Assignee: Zeneca Limited
    Inventor: Martin Charles Bowden
  • Patent number: 5731469
    Abstract: A process for the preparation of 3-chloropropionic acid consists especially in simultaneously introducing hydrochloric acid gas and acrylic acid at a molar ratio of 0.7:1 to 1.3:1 into a sediment consisting of 3-chloropropionic acid optionally diluted with water or with an aqueous hydrochloric acid solution.
    Type: Grant
    Filed: March 4, 1996
    Date of Patent: March 24, 1998
    Assignee: Elf Atochem S.A.
    Inventors: Gilles Drivon, Christophe Ruppin
  • Patent number: 5674949
    Abstract: This invention pertains to a method for liquid-phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: October 7, 1997
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
  • Patent number: 5539059
    Abstract: This invention pertains to perfluoropolyethers and perhalogenated chlorofluoropolyethers that can be prepared by fluorinating addition polymers made by polymerizing epoxides.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: July 23, 1996
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
  • Patent number: 5527954
    Abstract: Provided is a process for the production of 2-fluoroisobutyric acid or its ester, which comprises reacting 2-hydroxyisobutyric acid or its ester with thionyl chloride and a hydrogen fluoride source.
    Type: Grant
    Filed: January 26, 1995
    Date of Patent: June 18, 1996
    Assignee: Idemitsu Kosan Co., Ltd.
    Inventors: Ryoichi Adachi, Masahiro Nishii, Tadashi Kikukawa, Yasuhito Kotsuji
  • Patent number: 5461117
    Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.
    Type: Grant
    Filed: June 13, 1994
    Date of Patent: October 24, 1995
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu Kawa, Richard J. Lagow
  • Patent number: 5442084
    Abstract: The present invention is a method for selectively fluorinating various methylenephosphonate and methylenephosphorane derivatives using an electrophilic fluorinating agent, such as N-fluoro 1,4-diazabicyclo[ 2.2.2]octane by fluorinating the monohalogenated methylenephosphonate or methylenephosphorane derivative to produce fluoromethylenephosphonate or fluoro-methylenephosphorane derivatives useful as fluorinated Horner-Emmons or Wittig reagents in producing selectively fluorinated vinylic compounds.
    Type: Grant
    Filed: October 28, 1994
    Date of Patent: August 15, 1995
    Assignee: Air Products and Chemicals, Inc.
    Inventor: Gauri S. Lal
  • Patent number: 5401876
    Abstract: Chloroacetic acids and essentially pure hydrochloric acid are prepared by chlorinating acetic acid in the presence of a catalytically effective amount of acetic anhydride, acetyl chloride, or admixture thereof, whereby byproducing a gaseous stream of crude hydrochloric acid, contacting such gaseous stream with active charcoal to remove the chlorine values therefrom, separating (i) pure hydrochloric acid and (ii) remaining products from the gaseous stream thus purified, and recycling such remaining products (ii) to the medium of chlorination.
    Type: Grant
    Filed: July 23, 1993
    Date of Patent: March 28, 1995
    Assignee: Elf Atochem S.A.
    Inventors: Yves Correia, Daniel Pellegrin
  • Patent number: 5384415
    Abstract: A process for the preparation of a brominated compound which comprises the step of reacting at least one compound selected from the group consisting of a chloroformate, a chlorosulfite and a chlorophosphite with a brominating agent for a time sufficient to obtain at least one brominated compound. In particular, an alcohol is converted into a chloroformate, chlorosulfite or a chlorophosphite, which is then brominated to obtain the desired product. In another embodiment, a brominating agent is reacted with a reactant selected from the group consisting of thionyl chloride, phosgene and phosphorous oxychloride, followed by contacting the reaction product obtained with an alcohol to be brominated.
    Type: Grant
    Filed: May 28, 1993
    Date of Patent: January 24, 1995
    Assignee: Rhone-Poulenc Chimie
    Inventors: Jean-Manuel Mas, Pascal Metivier
  • Patent number: 5332790
    Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.
    Type: Grant
    Filed: March 8, 1993
    Date of Patent: July 26, 1994
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
  • Patent number: 5322903
    Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.
    Type: Grant
    Filed: January 17, 1992
    Date of Patent: June 21, 1994
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
  • Patent number: 5322904
    Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.
    Type: Grant
    Filed: March 8, 1993
    Date of Patent: June 21, 1994
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu Kawa, Richard J. Lagow
  • Patent number: 5241086
    Abstract: A process for the preparation of a brominated compound which comprises the step of reacting at least one compound selected from the group consisting of a chloroformate, a chlorosulfite and a chlorophosphite with a brominating agent for a time sufficient to obtain at least one brominated compound. In particular, an alcohol is converted into a chloroformate, chlorosulfite or a chlorophosphite, which is then brominated to obtain the desired product. In another embodiment, a brominating agent is reacted with a reactant selected from the group consisting of thionyl chloride, phosgene and phosphorous oxychloride, followed by contacting the reaction product obtained with an alcohol to be brominated.
    Type: Grant
    Filed: December 4, 1992
    Date of Patent: August 31, 1993
    Assignee: Rhone-Poulenc Chimie
    Inventors: Jean-Manuel Mas, Pascal Metivier
  • Patent number: 5215671
    Abstract: The present invention is directed to a method for recovering 2-chloropropionic acid so that this compound can be separated in a high-purity form. According to the method, crude 2-chloropropionic acid is heat-treated in the presence of a metal compound at a temperature in the range of 130.degree.-180.degree. C. where dichloro derivatives are contained as impurities or at a temperature not exceeding 160.degree. C. where no dichloro derivatives are contained. The metal compound is then removed at 160.degree. C. or lower. Final purification is thereafter conducted to obtain 2-chloropropionic acid as a high-purity product.
    Type: Grant
    Filed: June 11, 1991
    Date of Patent: June 1, 1993
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Yuzo Ono, Thutomu Kajikuri, Shoji Kitado, Kenji Senoo
  • Patent number: 5175345
    Abstract: A 2-fluoroisobutyric acid ester can be obtained at a high yield in one pot by reacting a 2-hydroxyisobutyric acid ester with fluorosulfuric acid in the absence or presence of a hydrogen fluoride source, or by reacting a 2-hydroxyisobutyric acid ester with chlorosulfuric acid in the presence of a hydrogen fluoride source.
    Type: Grant
    Filed: March 23, 1992
    Date of Patent: December 29, 1992
    Assignee: Idemitsu Kosan Company Limited
    Inventors: Izumi Terada, Masahiro Nishii, Kazufumi Nakamura
  • Patent number: 5144067
    Abstract: Disclosed is a process for the coproduction of (1) an alkyl iodide and (2) an .alpha.-iodocarboxylic acid, a mono-.alpha.-iodocarboxylic anhydride or a mixture thereof which comprises contacting a mixture of an iodine compound and a carboxylic anhydride with a peroxide at an elevated temperature.
    Type: Grant
    Filed: September 29, 1989
    Date of Patent: September 1, 1992
    Assignee: Eastman Kodak Company
    Inventors: Joseph R. Zoeller, Michael R. Cushman, Regina M. Moncier, Brent A. Tennant
  • Patent number: 5093432
    Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.
    Type: Grant
    Filed: September 28, 1989
    Date of Patent: March 3, 1992
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
  • Patent number: 4983747
    Abstract: Disclosed is a process for the preparation of a perfluoroorganic compound, which comprises fluorinating a partially fluorinated or unfluorinated organic compound having carbon-to-fluorine bonds under mild conditions and then, contacting the resulting reaction mixture with a fluorine gas at a temperature of 110.degree. to 180.degree. C.
    Type: Grant
    Filed: March 15, 1990
    Date of Patent: January 8, 1991
    Assignee: Tokuyama Soda Kabushiki Kaisha
    Inventors: Masakatsu Nishimura, Naoya Okada, Yasuo Murata, Yasuhiko Hirai
  • Patent number: 4806684
    Abstract: The invention relates to the synthesis of bromofluoroacetic acids of formula: ##STR1## in which X is a hydrogen, fluorine, chlorine or bromine atom. These acids are prepared by reacting a compound of formula: ##STR2## dissolved in concentrated hydrobromic acid, X having the same meaning as above and R representing a hydrogen atom or an alkyl or aryl radical, with gaseous hydrogen bromide.
    Type: Grant
    Filed: September 3, 1986
    Date of Patent: February 21, 1989
    Assignee: Atochem
    Inventors: Gilles Drivon, Bernard Gurtner
  • Patent number: 4383121
    Abstract: A mixture containing monochloroacetic acid and dichloroacetic acid as the main components are admixed with 5-25% by weight of water on the basis of sum total of monochloroacetic acid, dichloroacetic acid and water, and subjected to adiabatic cooling under a pressure of 133 to 2,660 Pa, whereby monochloroacetic acid is crystallized with a high purity.
    Type: Grant
    Filed: January 12, 1981
    Date of Patent: May 10, 1983
    Assignee: Tsukishima Kaikai Co., Ltd.
    Inventors: Ryoji Sugamiya, Kazuto Nakamaru, Keizo Takegami, Koji Miwa, Minoru Morita
  • Patent number: 4281184
    Abstract: Production of monochloroacetic acid with a minimum of polychlorinated derivatives in a two stage process by reaction of acetic anhydride and hydrogen chloride at a low temperature to produce a solution of acetyl chloride in acetic acid and chlorinating the said solution at a higher temperature which may be effected in a continuous manner.
    Type: Grant
    Filed: March 22, 1978
    Date of Patent: July 28, 1981
    Assignee: Fondazione deNora
    Inventors: Placido Spaziante, Giancarlo Sioli, Luigi Giuffre
  • Patent number: 4221921
    Abstract: A process for producing monochloroacetic acid from hydroxyacetic acid which comprises feeding hydroxyacetic acid and aqueous hydrogen chloride to a reaction zone and contacting the hydroxyacetic acid with the aqueous hydrogen chloride in the presence of hydrogen iodide catalyst at a temperature between 100.degree. and 250.degree. C. and a pressure sufficient to maintain the aqueous hydrogen chloride in liquid phase. Preferably the reaction is carried out at a temperature between about 130.degree. and 200.degree. C.
    Type: Grant
    Filed: May 10, 1978
    Date of Patent: September 9, 1980
    Assignee: Chevron Research Company
    Inventor: Shigeto Suzuki
  • Patent number: 4213919
    Abstract: The manufacture of .beta.-chlorocarboxylic acid chlorides by reacting .alpha..beta.-olefinically unsaturated carboxylic acids with phosgene is advantageously carried out by first at least partially reacting the unsaturated carboxylic acid with hydrogen chloride and then carrying out the reaction with phosgene.
    Type: Grant
    Filed: November 13, 1978
    Date of Patent: July 22, 1980
    Assignee: BASF Aktiengesellschaft
    Inventors: Joachim Datow, Martin Decker, Karl Merkel, Franz Neumayr
  • Patent number: 4161612
    Abstract: A process for preparing thiodiglycolic acid comprises contacting bromoacetic acid, diglycolic acid or glycolic acid and hydrogen sulfide in the presence of aqueous hydrogen bromide.
    Type: Grant
    Filed: March 31, 1978
    Date of Patent: July 17, 1979
    Assignee: Chevron Research Company
    Inventor: Shigeto Suzuki