Halogenation Patents (Class 562/864)
  • Patent number: 11639326
    Abstract: This disclosure generally relates to methods of making ibuprofen, naproxen, and derivatives thereof. This disclosure also generally relates to compounds made by the disclosed methods. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.
    Type: Grant
    Filed: April 6, 2018
    Date of Patent: May 2, 2023
    Assignee: SRI International
    Inventors: Nathan Collins, Jeremiah Malerich, Judy Szeto, Joseph A. Kozocas
  • Patent number: 8513459
    Abstract: Perfluoropolyether carboxylic acid fluoride having the following general formula: F(CF2CF2CF2O)nCF2CF2COF (n: 2-200, preferably 35-70) can be produced by starting fluorination reaction of polyfluoropolyether carboxylic acid having the general formula as a tetrafluorooxetane polymer: F(CH2CF2CF2O)nCH2CF2COF (n: 2-200) in a dispersed state in a perfluoropolyether-based solvent with a fluorine gas at 50°-80° C., then slowly elevating the fluorination reaction temperature, and finally completing the fluorination reaction at 100°-120° C., where even in the case of fluorination reaction of the starting material with a high degree of polymerization the desired product can be produced in high yield, while suppressing the decomposition and keeping the high degree of polymerization substantially.
    Type: Grant
    Filed: February 1, 2007
    Date of Patent: August 20, 2013
    Assignee: Unimatec Co., Ltd.
    Inventor: Sunao Ikeda
  • Patent number: 7321062
    Abstract: A process for the synthesis of (per)fluorinated mono-functional carbonyl compounds having the following formula: F—A—(RF)t—B—C(O)X1??(I) wherein: X1=F, CF3; t=0, 1; A, B equal to or different from each other, are independently C1-C5 (per)fluoroalkylene groups or C1-C5 (per)fluorooxy-alkylene groups; RF is —Rf1—, C1-C20 perfluoroalkylene, —ORf1O—; or —ORf2—, wherein Rf2 is a perfluorooxyalkylene chain; wherein the carbonyl groups of a (per)fluorinated di-functional carbonyl compound of formula (III): X2(O)C—A—(RF)t—B—C(O)X1??(III) wherein: X1, RF, t, A and B have the above meanings; X2, equal to or different from X1, has the same meanings as X1; are partially fluorinated with elemental fluorine in the presence of a catalyst having formula MeFy.zHF, Me being an alkaline or alkaline-earth metal or Ag, y=1 or 2, z an integer from 0 to 4, carrying out said reaction at a temperature higher than a temperature such that it leads to the formation of C(O)FX2.
    Type: Grant
    Filed: January 9, 2004
    Date of Patent: January 22, 2008
    Assignee: Solvay Solexis S.p.A.
    Inventors: Giovanni Fontana, Walter Navarrini
  • Patent number: 6911558
    Abstract: Describes a method for obtaining substantially pure chloromethyl chloroformate from a chloroformate mixture comprising chloromethyl chloroformate and methyl chloroformate by heating the chloroformate mixture in a reaction zone at temperatures ranging from at least 50° C. to the reflux temperature of the chloroformate mixture in the reaction zone while simultaneously removing volatile gaseous decomposition products from the reaction zone. Dichloromethyl chloroformate may also be present in the chloroformate mixture.
    Type: Grant
    Filed: February 5, 2003
    Date of Patent: June 28, 2005
    Assignee: PPG Industries Ohio, Inc.
    Inventors: Mark P. Bowman, Charles B. Kreutzberger
  • Publication number: 20030144546
    Abstract: A nitrous acid salt is added at a temperature of 10 to 80° C. to an aqueous solution which contains an optically active 2-aminocarboxylic acid (4) and a protonic acid, the amount of the latter acid being 1 to 3 equivalents to the former, and which has a proton concentration of 0.5 to 2 mol/kg to conduct a reaction to thereby produce an optically active 2-hydroxycarboxylic acid (1). Thionyl chloride and a basic compound are caused to act on the compound (1) to chlorinate it and simultaneously invert the configuration in the 2-position. Thus, an optically active 2-chlorocarboxylic acid chloride (5) is induced. The compound (5) is hydrolyzed to induce an optically active 2-chlorocarboxylic acid (2). The compound (2) is reacted with a thioacetic acid salt to incorporate an acetylthio group thereinto and simultaneously invert the configuration in the 2-position to thereby produce an optically active 2-acetylthiocarboxylic acid (3).
    Type: Application
    Filed: September 25, 2002
    Publication date: July 31, 2003
    Inventors: Susumu Amano, Masaru Mitsuda, Kenji Inoue, Koichi Kinoshita, Koki Yamashita, Yasuyoshi Ueda
  • Publication number: 20020169276
    Abstract: A synthetic process of perfluoropolyether iodides, by reaction with LiI of monoacyl- or diacyl-halides of perfluoropolyethers, having number average molecular weight from 200 to 3,000, and having the following structure:
    Type: Application
    Filed: May 9, 2002
    Publication date: November 14, 2002
    Applicant: AUSIMONT S.P.A.
    Inventors: Ivan Wlassics, Vito Tortelli
  • 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
  • Patent number: 6417407
    Abstract: A 2-bromo-4-chloro substituted phenol is prepared from a first composition of a substituted phenol and benzotrifluoride in a weight ratio to the substituted phenol of about 2 to about 4. Into the first composition is sparged about 1 to about 1.5 equivalents of chlorine gas, whereby the substituted phenol is chlorinated to form a 4-chloro substituted phenol. The first composition is cooled to precipitate the 4-chloro substituted phenol, which can be isolated by filtration. A second composition is formed of the 4-chloro substituted phenol, acetic acid in an weight ratio to the 4-chloro substituted phenol of about 1 to about 2, about 1 to about 2 equivalents of a salt of a strong base and a weak acid, and about 1 to about 5 equivalents of a brominating agent, whereby the 4-chloro substituted phenol is brominated to form a 2-bromo-4-chloro substituted phenol.
    Type: Grant
    Filed: February 10, 2000
    Date of Patent: July 9, 2002
    Assignee: Gabriel Performance Products, LLC
    Inventors: Bao-Guo Huang, Lawrence B. Fertel
  • Patent number: 6187952
    Abstract: The present invention relates to a process for the preparation of 3-chloro-4-fluorobenzoyl chloride which comprises reacting 4-fluorobenzaldehyde with a chlorinating agent in the presence of a free-radical initiator in the presence or absence of a solvent at from −20 to 200° C. to give 4-fluorobenzoyl chloride, and reacting the 4-fluorobenzoyl chloride with a chlorinating agent in the presence of a chlorination catalyst in the presence or absence of a solvent at from −20 to 200° C. to give 3-chloro-4-fluorobenzoyl chloride.
    Type: Grant
    Filed: December 10, 1998
    Date of Patent: February 13, 2001
    Assignee: Clariant GmbH
    Inventors: Ralf Pfirmann, Thomas Wessel
  • Patent number: 6066764
    Abstract: The present invention relates to halogenated aromatic derivatives, in particular 3-chloro-4-fluoro-benzoyl chloride having the following formula: ##STR1## The aforesaid derivative is advantageously used as base product for the preparation of fluorinated compounds employed in their turn as active principles in the pharmaceutical and agricultural fields as well as in dye industry.
    Type: Grant
    Filed: September 10, 1998
    Date of Patent: May 23, 2000
    Assignee: Miteni S.p.A.
    Inventors: Dino Bonini, Damiano Torrente, Filippo Maria Carlini
  • 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: 5859298
    Abstract: 2-Halogeno-4,5-difluoro-benzoyl fluorides are obtained in high yields by reacting 2,4-dichloro-5-fluoro-benzoyl halides with potassium fluoride in an aprotic solvent. The 2-halogeno-4,5-difluoro-benzoyl fluorides prepared in this way are particularly suitable as intermediates for the preparation of antibacterial active substances.
    Type: Grant
    Filed: February 13, 1997
    Date of Patent: January 12, 1999
    Assignee: Bayer Aktiengesellschaft
    Inventors: Stefan Antons, Albrecht Marhold, Bernhard Beitzke
  • Patent number: 5723613
    Abstract: Methyl aromatic compounds of the formula (I) ##STR1## in which R.sup.1, R.sup.2 and R.sup.3 have the meaning given in the description,can be reacted in an advantageous manner using free-radicals to give the associated trichloromethyl or tribromomethyl aromatic compounds, if the reaction is carried out in the presence of one or more chlorides or bromides of the heavy alkali metals.
    Type: Grant
    Filed: October 2, 1992
    Date of Patent: March 3, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventor: Guido Steffan
  • Patent number: 5659078
    Abstract: The invention relates to a process for the preparation of trichloroacetyl chloride by reaction of acetyl chloride or acetaldehyde or chlorinated derivatives thereof with chlorine in the presence of active charcoal as the catalyst.
    Type: Grant
    Filed: July 31, 1995
    Date of Patent: August 19, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Frank Ebmeyer, Tobias Metzenthin, Gunter Siegemund
  • 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: 5380927
    Abstract: A chemical process is disclosed for the preparation of a pharmaceutically active compound in stereospecific form selected from the group of compounds having the formula: ##STR1## and their physiologically compatible salts and esters, wherein R is a lower alkyl and Ar a monocyclic, polycyclic or orthocondensed polycyclic aromatic group having up to 12 carbon atoms in the aromatic ring, and which may be substituted or unsubstituted in the aromatic ring, comprising the steps:a) reacting a carbonyl substrate of the formula: ##STR2## where R and Ar have the meanings given above, with a stereospecific reagent in the presence of a reducing agent and an organic solvent to form the enatiomeric carbinol andb) reacting the enantiomeric carbinol obtained to form the end product.
    Type: Grant
    Filed: May 16, 1990
    Date of Patent: January 10, 1995
    Assignee: Medice Chem.-Pharm. Fabrik Putter GmbH & Co. KG
    Inventors: Henrich H. Paradies, Samir B. Hanna, Bernd Schneider
  • 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
  • Patent number: 5312982
    Abstract: The invention relates to a new process for the preparation of known .beta.-halogeno-tert.-alkylcarboxylic acid chlorides of the general formula (I) ##STR1## in which X represents chlorine,Y represents hydrogen or chlorine,R.sub.1 represents in each case straight-chain or branched lower alkyl or halogeno alkyl andR.sub.2 represents in each case straight-chain or branched lower alkyl or halogeno alkyl or optionally halogen- and/or trifluoromethyl-substituted phenyl,where tert.-alkylcarboxylic acid chlorides of the general formula (II) ##STR2## in which R.sup.1 and R.sup.2 are defined as above, are reacted with elementary chlorine optionally under irradiation or in the presence of free-radical catalysts.
    Type: Grant
    Filed: April 2, 1992
    Date of Patent: May 17, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventor: Rudiger Schubart
  • Patent number: 5258547
    Abstract: A process for preparing halogenated compounds of formula RCY(Z)CH.sub.2 CH(X)C(CH.sub.3)CH.sub.2 COR.sup.1 where X, Y and Z are halo, R is alkyl, halo, haloalkyl or aryl, and R.sup.1 is hydroxy, halo, alkoxy, alkyl or haloalkyl, or the residue of a pyrethroidal alcohol, in which a compound of formula CH.sub.2 =CHC(CH.sub.3).sub.2 COR.sup.1 is reacted with a sulphonyl halide of formula RCY(Z)SO.sub.2 X. The process avoids the use of volatile halocarbons in the production of valuable intermediates for insecticides.
    Type: Grant
    Filed: January 9, 1992
    Date of Patent: November 2, 1993
    Assignee: Imperial Chemical Industries plc
    Inventor: Gary N. Sheldrake
  • Patent number: 5247105
    Abstract: The invention provides a process for preparing fatty acid halide by reacting a fatty acid with a halogenating agent optionally followed by hydrolysis of unreacted halogenating agent and separating the fatty acid halide upper layer from the inorganic lower layer characterized in that a fatty acid nitrogen derivative, preferably a fatty amide has been incorporated in the reaction mixture. Preferably the fatty acid is a saturated or unsaturated C.sub.6 to C.sub.24 fatty acid and the halogenating agent a phosphorus halide, especially phosphorus trichloride.
    Type: Grant
    Filed: February 26, 1991
    Date of Patent: September 21, 1993
    Assignee: Unilever Patent Holdings B.V.
    Inventors: Reginald D. O. Evans, Raymond Jennings
  • 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: 5072030
    Abstract: Difluoropropionic acid and derivatives thereof are prepared by bringing elemental fluorine in the presence of a solvent into an addition reaction with appropriate acrylic acids or derivatives thereof. In this way, it is also possible to obtain novel fluorinated esters of 2,3-difluoropropionic acid.
    Type: Grant
    Filed: February 12, 1990
    Date of Patent: December 10, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Dietmar Bielefeldt, Karl-Rudolf Gassen, Walter Lange
  • Patent number: 5003105
    Abstract: A process for preparing 2-chloroterephthaloyl chloride which comprises reacting terephthaloyl chloride with chlorine in the presence of an anhydrous ring chlorination catalyst. When the reaction mixture contains the desired amount of the monochloro product, the mixture is cooled to room temperature and the 2-chloroterephthaloyl chloride is isolated.
    Type: Grant
    Filed: June 26, 1990
    Date of Patent: March 26, 1991
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Robert L. Seagraves
  • Patent number: 4994610
    Abstract: Fluorinated benzoyl compounds of the formula: ##STR1## wherein Q is a lower alkyl group, a halogen atom, --CH.sub.2 CO.sub.2 R.sup.1 wherein R.sup.1 is a lower alkyl group, or ##STR2## wherein each of R.sup.2 and R.sup.3 is a lower alkyl group, are disclosed.
    Type: Grant
    Filed: December 5, 1989
    Date of Patent: February 19, 1991
    Assignee: Asahi Glass Company, Ltd.
    Inventors: Seisaku Kumai, Osamu Yokokoji, Akihiro Tamaoki
  • Patent number: 4978769
    Abstract: Aromatic, ring-fluorinated compounds are particularly advantageously prepared by nucleophilic exchange in the course of reaction wih potassium fluoride in the presence of phase transfer catalysts and, if desired, solvents by carrying out the reaction in the additional presence of metal salts.
    Type: Grant
    Filed: August 7, 1989
    Date of Patent: December 18, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Ernst Kysela, Rudolf Braden