Halogenation Patents (Class 562/864)
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Patent number: 11639326Abstract: 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: GrantFiled: April 6, 2018Date of Patent: May 2, 2023Assignee: SRI InternationalInventors: Nathan Collins, Jeremiah Malerich, Judy Szeto, Joseph A. Kozocas
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Patent number: 8513459Abstract: 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: GrantFiled: February 1, 2007Date of Patent: August 20, 2013Assignee: Unimatec Co., Ltd.Inventor: Sunao Ikeda
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Patent number: 7321062Abstract: 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: GrantFiled: January 9, 2004Date of Patent: January 22, 2008Assignee: Solvay Solexis S.p.A.Inventors: Giovanni Fontana, Walter Navarrini
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Patent number: 6911558Abstract: 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: GrantFiled: February 5, 2003Date of Patent: June 28, 2005Assignee: PPG Industries Ohio, Inc.Inventors: Mark P. Bowman, Charles B. Kreutzberger
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Publication number: 20030144546Abstract: 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: ApplicationFiled: September 25, 2002Publication date: July 31, 2003Inventors: Susumu Amano, Masaru Mitsuda, Kenji Inoue, Koichi Kinoshita, Koki Yamashita, Yasuyoshi Ueda
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Publication number: 20020169276Abstract: 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: ApplicationFiled: May 9, 2002Publication date: November 14, 2002Applicant: AUSIMONT S.P.A.Inventors: Ivan Wlassics, Vito Tortelli
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Patent number: 6420601Abstract: 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: GrantFiled: January 25, 2001Date of Patent: July 16, 2002Assignee: Bayer AktiengesellschaftInventors: Albrecht Marhold, Jörn Stölting
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Patent number: 6417407Abstract: 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: GrantFiled: February 10, 2000Date of Patent: July 9, 2002Assignee: Gabriel Performance Products, LLCInventors: Bao-Guo Huang, Lawrence B. Fertel
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Patent number: 6187952Abstract: 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: GrantFiled: December 10, 1998Date of Patent: February 13, 2001Assignee: Clariant GmbHInventors: Ralf Pfirmann, Thomas Wessel
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Patent number: 6066764Abstract: 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: GrantFiled: September 10, 1998Date of Patent: May 23, 2000Assignee: Miteni S.p.A.Inventors: Dino Bonini, Damiano Torrente, Filippo Maria Carlini
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Patent number: 5945565Abstract: 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: GrantFiled: October 22, 1998Date of Patent: August 31, 1999Assignee: Rohm and Haas CompanyInventors: Enrique Luis Michelotti, Heather Lynnette Rayle, Randall Wayne Stephens, William Joseph Zabrodski
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Patent number: 5939581Abstract: 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: GrantFiled: August 20, 1997Date of Patent: August 17, 1999Assignee: First Chemical CorporationInventors: August John Muller, Joseph Stanton Bowers, Jr., John Robert Ira Eubanks, Carey Cecil Geiger, John Gabriel Santobianco
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Patent number: 5859298Abstract: 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: GrantFiled: February 13, 1997Date of Patent: January 12, 1999Assignee: Bayer AktiengesellschaftInventors: Stefan Antons, Albrecht Marhold, Bernhard Beitzke
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Patent number: 5723613Abstract: 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: GrantFiled: October 2, 1992Date of Patent: March 3, 1998Assignee: Bayer AktiengesellschaftInventor: Guido Steffan
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Patent number: 5659078Abstract: 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: GrantFiled: July 31, 1995Date of Patent: August 19, 1997Assignee: Hoechst AktiengesellschaftInventors: Frank Ebmeyer, Tobias Metzenthin, Gunter Siegemund
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Patent number: 5473095Abstract: 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: GrantFiled: January 27, 1994Date of Patent: December 5, 1995Assignee: Hoechst AktiengesellschaftInventors: Ralf Pfirmann, Theodor Papenfuhs, Georg Weichselbaumer
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Patent number: 5380927Abstract: 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: GrantFiled: May 16, 1990Date of Patent: January 10, 1995Assignee: Medice Chem.-Pharm. Fabrik Putter GmbH & Co. KGInventors: Henrich H. Paradies, Samir B. Hanna, Bernd Schneider
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Patent number: 5362909Abstract: 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: GrantFiled: October 29, 1992Date of Patent: November 8, 1994Assignee: Bayer AktiengesellschaftInventors: Erich Klauke, Uwe Petersen, Klaus Grohe
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Patent number: 5344977Abstract: 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: GrantFiled: January 22, 1993Date of Patent: September 6, 1994Assignee: Ciba-Geigy CorporationInventors: Alfons Arquint, Peter Leupin
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Patent number: 5312982Abstract: 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: GrantFiled: April 2, 1992Date of Patent: May 17, 1994Assignee: Bayer AktiengesellschaftInventor: Rudiger Schubart
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Patent number: 5258547Abstract: 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: GrantFiled: January 9, 1992Date of Patent: November 2, 1993Assignee: Imperial Chemical Industries plcInventor: Gary N. Sheldrake
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Patent number: 5247105Abstract: 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: GrantFiled: February 26, 1991Date of Patent: September 21, 1993Assignee: Unilever Patent Holdings B.V.Inventors: Reginald D. O. Evans, Raymond Jennings
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Patent number: 5126482Abstract: 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: GrantFiled: January 3, 1991Date of Patent: June 30, 1992Assignee: Nippon Mining Co., Ltd.Inventors: Takeshi Nakai, Osamu Takahashi
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Patent number: 5072030Abstract: 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: GrantFiled: February 12, 1990Date of Patent: December 10, 1991Assignee: Bayer AktiengesellschaftInventors: Dietmar Bielefeldt, Karl-Rudolf Gassen, Walter Lange
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Patent number: 5003105Abstract: 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: GrantFiled: June 26, 1990Date of Patent: March 26, 1991Assignee: E. I. Du Pont de Nemours and CompanyInventor: Robert L. Seagraves
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Patent number: 4994610Abstract: 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: GrantFiled: December 5, 1989Date of Patent: February 19, 1991Assignee: Asahi Glass Company, Ltd.Inventors: Seisaku Kumai, Osamu Yokokoji, Akihiro Tamaoki
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Patent number: 4978769Abstract: 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: GrantFiled: August 7, 1989Date of Patent: December 18, 1990Assignee: Bayer AktiengesellschaftInventors: Ernst Kysela, Rudolf Braden