Phosgene Reactant Patents (Class 562/857)
  • Patent number: 10689321
    Abstract: The disclosure provides a method for synthesizing paraphthaloyl chloride through terephthalic acid chlorination in a reaction mode of a microchannel continuous flow. Compared with an existing technology, this method has characteristics of accurate control of reaction conditions, high phosgene/triphosgene utilization ratio, low catalyst dosage, high TPA conversion ratio within few tens of seconds of reaction time, high TPC yield and the like.
    Type: Grant
    Filed: July 7, 2017
    Date of Patent: June 23, 2020
    Assignee: Jiangsu Yangnong Chemical Group Co., Ltd
    Inventors: Lin Xu, Yiming Wang, Bo Shao, Kehong Ding, Hui Yan, Chenchao Bian, Hui Zhao, Yushuang Wang
  • 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
  • Publication number: 20110251429
    Abstract: The present invention relates to a process for producing chlorothioformate comprising reacting an alkenyl mercaptan with phosgene in a reactor in the presence of a carboxylic acid amide in an organic solvent, characterized in that the carboxylic acid amide is preliminary charged to the reactor in an amount of 10 to 50% by weight based on the whole amount of the carboxylic acid amide, and subsequently, the compound of the formula (I), phosgene and the remaining carboxylic acid amide are charged to the reactor.
    Type: Application
    Filed: December 18, 2009
    Publication date: October 13, 2011
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Toshiaki Suzuki, Fumi Yonehara
  • 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
  • Patent number: 7405331
    Abstract: The process for producing a (fluoroalkyl)benzene derivative according to the present invention comprises a step of reducing the total content of group 3 to group 12 transition metals in an alkylbenzene derivative to 500 ppm or less in terms of metal atoms; a step of halogenating the branched alkyl group of the purified alkylbenzene derivative by a photohalogenation to obtain a (haloalkyl)benzene derivative; and a step of subjecting the (haloalkyl)benzene derivative to a halogen-fluorine exchange using HF in an amount of 10 mol or higher per one mole of the (haloalkyl)benzene derivative. The (fluoroalkyl)benzene derivative produced by the process is reduced in the content of impurities such as residual halogens and residual metals, and is useful as intermediates for functional chemical products for use in applications such as medicines and electronic materials.
    Type: Grant
    Filed: April 24, 2003
    Date of Patent: July 29, 2008
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Toshio Hidaka, Norio Fushimi, Takafumi Yoshimura, Takeshi Kawai
  • Patent number: 7045592
    Abstract: A process is disclosed for using bis-(trichloromethyl)carbonate (triphosgene), diphosgene or phosgene as efficient and effective coupling reagents during coupling of carbohydrates to peptide chains. This process is particularly useful for the coupling to sterically hindered amino acid residues, or for other difficult couplings. The reagents can be used for the derivatization of peptides by formation of a bond between a free amine on a peptide and a carbohydrate.
    Type: Grant
    Filed: December 18, 2002
    Date of Patent: May 16, 2006
    Assignee: DeveloGen Israel Ltd.
    Inventors: Eliezer Falb, Tamar Yechezkel, Yoseph Salitra
  • Patent number: 6770783
    Abstract: The invention relates to a method for producing acid chlorides by converting carboxylic acids with carbon oxychlorides or thionyl chloride in the presence of a catalyst adduct of an N,N-disubstituted formamide of general formula (I) and carbon oxychloride or thionyl chloride. In the formula, R1 and R2, independently from one another, mean C1- to C4-alkyl or R1 and R2 together mean a C4- or C5-alkylene chain. According to the inventive method, hydrogen chloride is added during and/or after the conversion.
    Type: Grant
    Filed: March 12, 2002
    Date of Patent: August 3, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Ralph Busch, Heinz-Josef Kneuper, Theodor Weber, Winfried Müller, Armin Stamm, Jochem Henkelmann
  • Patent number: 6734322
    Abstract: The invention relates to a method for producing o-choromethyl benzenecarbonyl chlorides of formula (I), wherein R1-R4 can be the same or different and stand for hydrogen, C1-C4-alkyl, halogen or trifluoromnethyl, by converting benzocondensed lactones of formula (II), wherein R1-R4 have the aforementioned meaning, with gaseous or liquid phosgene and the dimers or trimers thereof.
    Type: Grant
    Filed: May 23, 2002
    Date of Patent: May 11, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Armin Stamm, Roland Götz, Norbert Götz, Jochem Henkelmann, Heinz-Josef Kneuper, Bernd Wolf
  • Publication number: 20030028045
    Abstract: A process for preparing chlorocarbonyl chlorides of the formula (I) 1
    Type: Application
    Filed: August 27, 2002
    Publication date: February 6, 2003
    Inventors: Armin Stamm, Heinz-Josef Kneuper, Jochem Henkelmann, Theodor Weber, Ralph Busch
  • Publication number: 20030028046
    Abstract: A process for the preparation of chlorocarboxylic chlorides of formula (I) 1
    Type: Application
    Filed: August 27, 2002
    Publication date: February 6, 2003
    Inventors: Armin Stamm, Roland Gotz, Jochem Henkelmann, Friedrich Closs, Heinz-Josef Kneuper
  • Patent number: 6433224
    Abstract: The invention relates to a process for the preparation of acid chlorides by reaction of carboxylic acids, carboxylic anhydrides, cyclic carboxylic esters or sulfonic acids with phosgene in the presence of a catalytic amount of a compound from the group consisting of N,N,N′,N′-tetrasubstituted amidinium halides (I), N,N,N′-trisubstituted amidinium hydrohalides (II) and N,N,N′-trisubstituted amidines (III).
    Type: Grant
    Filed: April 25, 2001
    Date of Patent: August 13, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Armin Stamm, Jochem Henkelmann
  • Patent number: 6429334
    Abstract: A process that can be used to produce an acid anhydride or acid chloride is provided. The process comprises contacting a reaction medium with a catalyst. The reaction medium comprises at least one organic acid, combination of the organic acid and phosgene, combination of at least one organic anhydride and phosgene, or combinations of the organic acid, the organic anhydride, and phosgene. The reaction medium can further comprise a solvent. The catalyst is a Group IVB transition metal halide.
    Type: Grant
    Filed: June 7, 2000
    Date of Patent: August 6, 2002
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Gordon L. Thayer, Jr.
  • Publication number: 20010014759
    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: Application
    Filed: January 25, 2001
    Publication date: August 16, 2001
    Inventors: Albrecht Marhold, Jorn Stolting
  • Patent number: 6262300
    Abstract: The present invention provides process for the preparation of chlorocarbonyl chlorides of the formula I R1—CHCl—Y—COCl  (I), where R1 is for example hydrogen or C1- to C20-alkyl and Y is for example a saturated or mono- or polyolefinically unsaturated C2-C8-alkylene chain, by reacting lactones with a chlorinating agent in the presence of a urea compound.
    Type: Grant
    Filed: April 20, 2000
    Date of Patent: July 17, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Jürgen Weyer, Armin Stamm, Theodor Weber, Jochem Henkelmann
  • Patent number: 6124500
    Abstract: A nucleophilic substitution reaction on optionally substituted dihalobenzenes is carried out in the presence of an optional catalyst followed by formation of and subsequent carboxylation of a Grignard reaction intermediate. In particular the present invention provides a process leading to optionally substituted hydroxybenzoic, alkanoyloxybenzoic, formyloxybenzoic and alkoxybenzoic acids from 1-substituted 2,6-dihalobenzenes. The invention also provides a process for the direct formation of an acyl chloride from a Grignard reagent by quenching with phosgene.
    Type: Grant
    Filed: December 22, 1998
    Date of Patent: September 26, 2000
    Assignee: Rohm and Haas Company
    Inventors: Joshua Anthony Chong, Fereydon Abdesaken, Lori Ann Spangler, Sudhir Ramtirth Joshi, Charles Chao Wu
  • Patent number: 6002043
    Abstract: Process for the phosgenation of monocarboxylic acids and/or anhydrides, characterized in that the acid and/or the anhydride is treated, in the presence or absence of solvent, with a molar excess of phosgene, preferably 2 to 15 times as much phosgene as acid, at temperatures between 80 and 200.degree. C. and at pressures between 2 and 60 bar, with or without catalyst, preferably in the absence of any catalyst.Process furthermore characterized in that pressure is used to facilitate the separation of the hydrochloric acid, the carbon dioxide and the phosgene, in a column which is external to the reactor.
    Type: Grant
    Filed: November 17, 1997
    Date of Patent: December 14, 1999
    Assignee: Rhone-Poulenc Agrochimie Department Propriete Industrielle
    Inventors: Jean-Claude Descorps, Francois Metz
  • 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: 5792888
    Abstract: Phosgenation of carboxylic acids to the corresponding carboxylic acid chlorides in conducted in the presence of a solvent comprising acetonitrile.
    Type: Grant
    Filed: December 22, 1995
    Date of Patent: August 11, 1998
    Assignee: Zeneca Limited
    Inventor: N. Subramanian
  • 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: 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: 5430186
    Abstract: A process for the continuous manufacture of carboxylic chlorides (I) of the general formula R-COCl, in which R stands for a C-organic radical containing from 1 to 30 C atoms, by the reaction of a carboxylic acid (II) with a reaction product (III) of phosgene (IV) and an N,N-substituted formamide (V), in which compounds II and III are passed in parallel flow upwardly into a zone, filled with compound III, in a reactor (1), the reaction mixture is allowed to rise in predominantly laminar flow, such that phase separation occurs to give a top I-phase and a bottom phase III' mainly comprising compound III and formamide formed and compound I is removed from the top phase and also portions of the bottom phase III' are removed at the rate at which they are formed.
    Type: Grant
    Filed: July 14, 1994
    Date of Patent: July 4, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Ksoll, Wolfgang Reuther, Roland Ettl
  • Patent number: 5278328
    Abstract: Disclosed is a process for producing a carboxylic acid chloride by reacting phosgene with a carboxylic acid or an anhydride thereof, which comprises effecting the reaction in the presence of a homopolymer or copolymer of a monomer represented by formula (I) or (II) below, a copolymer of the monomers represented by formulae (I) and (II) below, or a copolymer of at least one monomer selected from the group sensisting of the monomers represented by formulae (I) and (II) below with another monomer copolymerizable therewith:CH.sub.2 .dbd.CHNR.sup.1 COR.sup.2 (I)CH.sub.2 .dbd.CR.sup.3 CONR.sup.4 R.sup.5 (II).In these formulae R.sup.1, R.sup.2, and R.sup.4 each represents an alkyl group containing from 1 to 3 carbon atoms, or an alkylene group containing from 3 to 5 carbon atoms provided that R.sup.1 with R.sup.2, and R.sup.4 with R.sup.5 may each combine to form a ring structure through >N--CO-- or >N-- in the molecule; R.sup.3 and R.sup.
    Type: Grant
    Filed: March 11, 1992
    Date of Patent: January 11, 1994
    Assignee: Nippon Oil & Fats Co., Ltd.
    Inventors: Takeshi Endo, Toshikazu Takata, Shinichi Ohno, Fujio Takahashi
  • Patent number: 5200560
    Abstract: A process for the preparation of a carboxylic chloride of the general formula I ##STR1## in which R denotes C.sub.1 -C.sub.30 -alkyl, C.sub.2 -C.sub.30 -alkenyl or C.sub.2 -C.sub.30 -alkynyl, from a carboxylic acid of the general formula II ##STR2## in which R has the meanings stated, and phosgene COCl.sub.2 (III), in the presence of a catalyst adduct comprising phosgene and N,N-disubstituted formamide of the general formula IV ##STR3## in which R.sup.1 and R.sup.2 are independently C.sub.1 -C.sub.3 -alkyl or R.sup.1 and R.sup.2 together form a C.sub.4 - or C.sub.5 -alkylene chain which may or may not be interrupted by an oxygen atom or by a nitrogen atom carrying a C.sub.1 -C.sub.3 -alkyl group or CHO, the product being isolated by phase separation, wherein the amount of phosgene added to the formamide (IV) is from 20 to 70% molar, based on the formamide.
    Type: Grant
    Filed: June 30, 1992
    Date of Patent: April 6, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Thomas M. Kahl, Jochem Henkelmann, Leopold Hupfer, Wolfgang Franzischka, Wolfgang Schwarz
  • Patent number: 5166427
    Abstract: Acyl chlorides of the general formula ##STR1## where R is C.sub.8 -C.sub.30 -alkyl, C.sub.8 -C.sub.30 -alkenyl or C.sub.8 -C.sub.30 -alkynyl, are prepared from a carboxylic acid of the general formula II ##STR2## where R has the abovementioned meanings, and phosgene, COCl.sub.2 (III), in the presence of a catalyst adduct of phosgene and N,N-dialkylformamide of the general formula IV ##STR3## where R.sup.1 and R.sup.2 independently of one another are each C.sub.1 -C.sub.3 -alkyl, preferably a 1:1 adduct in excess N,N-dialkylformamide, the reaction product I being obtained by phase separation, by a process in which II and III are used in essentially equimolar amounts and the phase containing the catalyst adduct is reused.
    Type: Grant
    Filed: June 24, 1991
    Date of Patent: November 24, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Andreas Hohmann, Enrique Freudenberg, Wolfgang Reuther, Kurt Mayer
  • Patent number: 5130478
    Abstract: The invention relates to a process for the preparation of chlorides of chlorinated carboxylic acids of formula ##STR1## in which R.sup.2 denotes the radical (CH.sub.2).sub.n, n being an integer from 2 to 4, or the radical --CH.sub.2 --C(C.sub.6 H.sub.5).sub.2 -- and R.sup.1 denotes a hydrogen atom or an alkyl radical containing from 1 to 4 carbon atoms, which consists in reacting the lactones of formula ##STR2## in which R.sup.1 and R.sup.2 have the above meanings, with phosgene at a temperature of 90.degree. to 180.degree. C., while employing as catalysts trisubstituted phosphine oxides or sulphides.The process according to the invention makes it possible to obtain chlorides of chlorinated carboxylic acids of high purity which exhibit an excellent stability to light and to heat and which are very useful as synthesis intermediates.
    Type: Grant
    Filed: December 6, 1990
    Date of Patent: July 14, 1992
    Assignee: Societe Nationale de Poudres et Explosifs
    Inventors: Patricia P. Gauthier, Michel M. Le Moult, Claude Rochelle, Jean-Pierre G. Senet
  • Patent number: 5126482
    Abstract: Novel fluorine-containing compounds and processes for producing the same are disclosed, the compounds being represented by the general formula (I): ##STR1## wherein R.sup.1 represents an alkyl group or an alkylvinyl group; R.sup.2 represents a fluoroalkyl group; and Y represents a carboxyl group, a chloroformyl group, an alkoxyalkoxycarbonyl group or a hydroxymethyl group.
    Type: Grant
    Filed: January 3, 1991
    Date of Patent: June 30, 1992
    Assignee: Nippon Mining Co., Ltd.
    Inventors: Takeshi Nakai, Osamu Takahashi
  • Patent number: 4938898
    Abstract: The present invention relates to improved processes for selectively chlorinating acyl compounds at the alpha or 2-position. The process of the present invention comprises a method of producing alpha-chloro acyl chlorides comprising contacting an acyl chloride with a chlorine source at a temperature of about 75.degree. C. to about 125.degree. C. in the presence of (i) an effective amount of an auxiliary acidic agent and (ii) an effective amount of a food grade antioxidant and optionally (iii) an effective amount of oxygen or air.
    Type: Grant
    Filed: June 29, 1984
    Date of Patent: July 3, 1990
    Assignee: The Procter & Gamble Company
    Inventor: James E. Thompson
  • Patent number: 4880576
    Abstract: An N-alkylated formamide of the formula ##STR1## wherein R.sup.1 denotes alkylR.sup.2 denotes alkyl with at least 9 carbon atoms or the group ##STR2## wherein A denotes straight-chain or branched alkanediyl,R.sup.1 denotes lower alkyl andn denotes an integer from 2 to 6,a process for the preparation of the same and its use in the replacement of a hydroxyl group in an organic compound by chlorine or bromine the improvement wherein the replacement is carried out in the presence of an N-alkylated formamide.
    Type: Grant
    Filed: September 17, 1986
    Date of Patent: November 14, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz U. Blank, Norbert Langenfeld, Wolfgang Heydkamp