Preparation By Halogenating Acid Or Anhydride Patents (Class 562/603)
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Patent number: 9187400Abstract: 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: GrantFiled: April 3, 2013Date of Patent: November 17, 2015Assignee: 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
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Patent number: 9073848Abstract: 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: GrantFiled: March 13, 2012Date of Patent: July 7, 2015Assignee: 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
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Publication number: 20140148603Abstract: 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: ApplicationFiled: May 29, 2012Publication date: May 29, 2014Applicant: RHODIA OPERATIONSInventors: Olivier Buisine, Michael Dejoux
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Publication number: 20130184469Abstract: 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: ApplicationFiled: August 23, 2011Publication date: July 18, 2013Inventors: Ramamohan Rao Davuluri, Ravi Ponnaiah, Sanjay Kumar Dehury, Selvaraju K., Deepthi VPSS, Dhanunjaya Naidu
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Publication number: 20130131375Abstract: 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: ApplicationFiled: July 26, 2011Publication date: May 23, 2013Applicant: RHODIA OPERATIONSInventor: Olivier Buisine
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Publication number: 20120245384Abstract: A method for preparing highly fluorinated carboxylic acids and theirs salts and the precursors thereof.Type: ApplicationFiled: November 18, 2010Publication date: September 27, 2012Inventors: Klaus Hintzer, Tilman C. Zipplies, Oleg Shyshkov
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Publication number: 20100160670Abstract: 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: ApplicationFiled: March 4, 2010Publication date: June 24, 2010Applicant: AVENTIS PHARMA S.A.Inventors: Veronique Crocq-Stuerga, Patrick Roussel
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Patent number: 7473803Abstract: 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: GrantFiled: February 4, 2003Date of Patent: January 6, 2009Assignee: Kaneka CorporationInventors: Koki Yamashita, Toshihiro Takeda, Yasuyoshi Ueda
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Patent number: 7247736Abstract: 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: GrantFiled: November 10, 2004Date of Patent: July 24, 2007Assignee: 4SC AGInventors: Johann Leban, Bernd Kramer, Roland Baumgartner, Katharina Aulinger-Fuchs, Stefan Tasler
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Patent number: 7135597Abstract: 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: GrantFiled: October 2, 2003Date of Patent: November 14, 2006Assignee: Akzo Nobel N.V.Inventors: Jeroen Crouzen, Johannes Joseph Gorissen, Cornelis Johannes Govardus Van Strien
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Patent number: 7030270Abstract: 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: GrantFiled: November 19, 2002Date of Patent: April 18, 2006Assignee: Akzo Nobel N.V.Inventors: Cornelis Kooijman, Jacobus Theodorus Jozef Aaldering
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Patent number: 6846952Abstract: 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: GrantFiled: June 7, 2002Date of Patent: January 25, 2005Assignee: Lupin LimitedInventors: Vinod Kumar Kansal, Dnyandeo Ragho Rane, Sanjay Deshmukh, Santosh Kumar Singh, Santosh Richaria, Susan Ajay Abraham
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Patent number: 6743929Abstract: Sulfonamide-containing hydroxyethylamine compounds are effecive as retroviral protease inhibitors, and in particular as inhibitors of HIV protease.Type: GrantFiled: September 6, 2000Date of Patent: June 1, 2004Assignee: G. D. Searle & Co.Inventors: Michael L. Vazquez, Richard A. Mueller, John J. Talley, Daniel Getman, Gary A. DeCrescenzo, John N. Freskos
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Patent number: 6049001Abstract: 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: GrantFiled: July 28, 1999Date of Patent: April 11, 2000Assignee: Sumitomo Chemical Company, LimitedInventors: Ken Otaka, Noritada Matsuo
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Patent number: 5753776Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.Type: GrantFiled: June 6, 1995Date of Patent: May 19, 1998Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5750769Abstract: 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: GrantFiled: November 8, 1995Date of Patent: May 12, 1998Assignee: Zeneca LimitedInventor: Martin Charles Bowden
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Patent number: 5731469Abstract: 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: GrantFiled: March 4, 1996Date of Patent: March 24, 1998Assignee: Elf Atochem S.A.Inventors: Gilles Drivon, Christophe Ruppin
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Patent number: 5674949Abstract: This invention pertains to a method for liquid-phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.Type: GrantFiled: June 6, 1995Date of Patent: October 7, 1997Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5539059Abstract: This invention pertains to perfluoropolyethers and perhalogenated chlorofluoropolyethers that can be prepared by fluorinating addition polymers made by polymerizing epoxides.Type: GrantFiled: June 6, 1995Date of Patent: July 23, 1996Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5527954Abstract: 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: GrantFiled: January 26, 1995Date of Patent: June 18, 1996Assignee: Idemitsu Kosan Co., Ltd.Inventors: Ryoichi Adachi, Masahiro Nishii, Tadashi Kikukawa, Yasuhito Kotsuji
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Patent number: 5461117Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.Type: GrantFiled: June 13, 1994Date of Patent: October 24, 1995Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5442084Abstract: 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: GrantFiled: October 28, 1994Date of Patent: August 15, 1995Assignee: Air Products and Chemicals, Inc.Inventor: Gauri S. Lal
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Patent number: 5401876Abstract: 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: GrantFiled: July 23, 1993Date of Patent: March 28, 1995Assignee: Elf Atochem S.A.Inventors: Yves Correia, Daniel Pellegrin
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Patent number: 5384415Abstract: 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: GrantFiled: May 28, 1993Date of Patent: January 24, 1995Assignee: Rhone-Poulenc ChimieInventors: Jean-Manuel Mas, Pascal Metivier
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Patent number: 5332790Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.Type: GrantFiled: March 8, 1993Date of Patent: July 26, 1994Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5322904Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.Type: GrantFiled: March 8, 1993Date of Patent: June 21, 1994Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5322903Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.Type: GrantFiled: January 17, 1992Date of Patent: June 21, 1994Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5241086Abstract: 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: GrantFiled: December 4, 1992Date of Patent: August 31, 1993Assignee: Rhone-Poulenc ChimieInventors: Jean-Manuel Mas, Pascal Metivier
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Patent number: 5215671Abstract: 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: GrantFiled: June 11, 1991Date of Patent: June 1, 1993Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Yuzo Ono, Thutomu Kajikuri, Shoji Kitado, Kenji Senoo
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Patent number: 5175345Abstract: 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: GrantFiled: March 23, 1992Date of Patent: December 29, 1992Assignee: Idemitsu Kosan Company LimitedInventors: Izumi Terada, Masahiro Nishii, Kazufumi Nakamura
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Patent number: 5144067Abstract: 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: GrantFiled: September 29, 1989Date of Patent: September 1, 1992Assignee: Eastman Kodak CompanyInventors: Joseph R. Zoeller, Michael R. Cushman, Regina M. Moncier, Brent A. Tennant
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Patent number: 5093432Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.Type: GrantFiled: September 28, 1989Date of Patent: March 3, 1992Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 4983747Abstract: 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: GrantFiled: March 15, 1990Date of Patent: January 8, 1991Assignee: Tokuyama Soda Kabushiki KaishaInventors: Masakatsu Nishimura, Naoya Okada, Yasuo Murata, Yasuhiko Hirai
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Patent number: 4806684Abstract: 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: GrantFiled: September 3, 1986Date of Patent: February 21, 1989Assignee: AtochemInventors: Gilles Drivon, Bernard Gurtner
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Patent number: 4383121Abstract: 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: GrantFiled: January 12, 1981Date of Patent: May 10, 1983Assignee: Tsukishima Kaikai Co., Ltd.Inventors: Ryoji Sugamiya, Kazuto Nakamaru, Keizo Takegami, Koji Miwa, Minoru Morita
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Patent number: 4281184Abstract: 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: GrantFiled: March 22, 1978Date of Patent: July 28, 1981Assignee: Fondazione deNoraInventors: Placido Spaziante, Giancarlo Sioli, Luigi Giuffre
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Patent number: 4221921Abstract: 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: GrantFiled: May 10, 1978Date of Patent: September 9, 1980Assignee: Chevron Research CompanyInventor: Shigeto Suzuki
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Patent number: 4213919Abstract: 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: GrantFiled: November 13, 1978Date of Patent: July 22, 1980Assignee: BASF AktiengesellschaftInventors: Joachim Datow, Martin Decker, Karl Merkel, Franz Neumayr
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Patent number: 4161612Abstract: 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: GrantFiled: March 31, 1978Date of Patent: July 17, 1979Assignee: Chevron Research CompanyInventor: Shigeto Suzuki