Forming The Carbonyl To Halide Bond Patents (Class 562/861)
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Patent number: 10730819Abstract: A naphthalenedicarboxylic acid dichloride production method includes causing a reaction between naphthalenedicarboxylic acid and a chlorinating agent at a reaction temperature of 20° C. or higher and 75° C. or lower in presence of a solvent including tetrahydrofuran. The causing a reaction in the naphthalenedicarboxylic acid dichloride production method is preferably performed in presence of N,N-disubstituted formamide.Type: GrantFiled: September 18, 2019Date of Patent: August 4, 2020Assignee: KYOCERA Document Solutions Inc.Inventor: Jun Azuma
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Patent number: 8993819Abstract: The present invention provides a process for preparing cycloheptene and derivatives thereof by ring-closing metathesis of unsymmetric 1,8-dienes whose C—C double bond at the 8 position is nonterminal. Cycloheptene and the cycloheptanone, cycloheptylamine, cycloheptanecarbaldehyde, cycloheptanecarboxylic acid and cycloheptanecarbonyl chloride conversion products thereof, and the derivatives thereof, are important synthesis units for active ingredient compounds. The ring-closing metathesis is preferably performed as a reactive distillation. The unsymmetric 1,8-dienes for the ring-closing metathesis can be obtained by catalytic decarbonylation or oxidative decarboxylation from the corresponding unsaturated carboxylic acids or carboxylic acid derivatives.Type: GrantFiled: July 10, 2012Date of Patent: March 31, 2015Assignee: BASF SEInventors: Joaquim Henrique Teles, Michael Limbach, Richard Dehn, Stephan Deuerlein, Manuel Danz
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Publication number: 20140336403Abstract: A process for the preparation of a compound of formula (I): which is useful as an intermediate in the preparation of pharmaceutically active compounds.Type: ApplicationFiled: July 25, 2014Publication date: November 13, 2014Inventors: Gerard John Harnett, John Hayes, Reinhard Reents, Dennis A. Smith, Andrew Walsh
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Patent number: 8785689Abstract: A method for purifying difluoroacetic acid chloride, including the step of bringing a difluoroacetic acid chloride composition that contains at least difluoroacetic acid fluoride into contact with calcium chloride at a temperature enabling reaction thereof thereby converting difluoroacetic acid fluoride into difluoroacetic acid chloride.Type: GrantFiled: March 28, 2012Date of Patent: July 22, 2014Assignee: Central Glass Company, LimitedInventors: Naoto Takada, Masamune Okamoto, Hideaki Imura
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Patent number: 8642805Abstract: A method of producing a phthaloyl dichloride compound, the method including: providing a compound represented by the following formula (1) and a compound represented by the following formula (2); and bringing the compound represented by the following formula (1) and the compound represented by the following formula (2) into reaction, so as to form a compound represented by the following formula (3), in the presence of at least one compound selected from a zirconium compound, a hafnium compound, and zinc oxide; wherein, in formulae, X represents a hydrogen atom, a halogen atom, a nitro group, a methyl group, or a methoxy group; when the X is plural, Xs may be the same or different from each other; n represents an integer of from 0 to 2; R represents a halogen atom, a chlorocarbonyl group, a low carbon number alkyl group, or a halogen-substituted low carbon number alkyl group; when the R is plural, Rs may be the same or different from each other; and m represents an integer of from 0 to 2.Type: GrantFiled: July 27, 2009Date of Patent: February 4, 2014Assignees: Iharanikkei Chemical Industry Co., Ltd., Nippon Light Metal Company, Ltd.Inventors: Yoshikazu Kimura, Yoshihiro Takao, Toshimitsu Sugiyama, Takeshi Hanawa, Hiromichi Ito
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Publication number: 20140031588Abstract: A method for purifying difluoroacetic acid chloride, including the step of bringing a difluoroacetic acid chloride composition that contains at least difluoroacetic acid fluoride into contact with calcium chloride at a temperature enabling reaction thereof thereby converting difluoroacetic acid fluoride into difluoroacetic acid chloride.Type: ApplicationFiled: March 28, 2012Publication date: January 30, 2014Applicant: Central Glass Campany, LimitedInventors: Naoto Takada, Masamune Okamoto, Hideaki Imura
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Publication number: 20130197257Abstract: A process for the preparation of a compound of formula (I): which is useful as an intermediate in the preparation of pharmaceutically active compounds.Type: ApplicationFiled: March 14, 2013Publication date: August 1, 2013Applicant: Hoffmann-La Roche Inc.Inventor: Hoffmann-La Roche Inc.
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Publication number: 20130018205Abstract: The present invention provides a process for preparing cycloheptene and derivatives thereof by ring-closing metathesis of unsymmetric 1,8-dienes whose C—C double bond at the 8 position is nonterminal. Cycloheptene and the cycloheptanone, cycloheptylamine, cycloheptanecarbaldehyde, cycloheptanecarboxylic acid and cycloheptanecarbonyl chloride conversion products thereof, and the derivatives thereof, are important synthesis units for active ingredient compounds. The ring-closing metathesis is preferably performed as a reactive distillation. The unsymmetric 1,8-dienes for the ring-closing metathesis can be obtained by catalytic decarbonylation or oxidative decarboxylation from the corresponding unsaturated carboxylic acids or carboxylic acid derivatives.Type: ApplicationFiled: July 10, 2012Publication date: January 17, 2013Applicant: BASF SEInventors: Joaquim Henrique TELES, Michael Limbach, Richard Dehn, Stephan Deuerlein, Manuel Danz
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Publication number: 20130012740Abstract: A production method of difluoroacetyl chloride according to the present invention includes a chlorination step of bringing a raw material containing at least either a 1-alkoxy-1,1,2,2-tetrafluoroethane or difluoroacetyl chloride into contact with calcium chloride at a reaction enabling temperature. A production method of 2,2-difluoroethyl alcohol according to the present invention includes a catalytic reduction step of causing catalytic reduction of the difluoroacetyl chloride obtained by the above production method. By these methods, the difluoroacetyl fluoride can be efficiently converted to the difluoroacetyl chloride and to the 2,2-difluoroethyl alcohol.Type: ApplicationFiled: March 16, 2011Publication date: January 10, 2013Applicant: Central Glass Company ,LimitedInventors: Masamune Okamoto, Hideaki Imura, Naoto Takada
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Patent number: 8198482Abstract: 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: GrantFiled: February 27, 2008Date of Patent: June 12, 2012Assignee: Mitsui Chemicals, Inc.Inventors: Takeshi Kobayashi, Kiyomi Kido, Akinori Nagatomo
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Patent number: 8153801Abstract: The invention provides synthetic processes and synthetic intermediates that can be used to prepare 4-oxoquinolone compounds having useful integrase inhibiting properties.Type: GrantFiled: September 11, 2008Date of Patent: April 10, 2012Assignee: Gilead Sciences, Inc.Inventors: Eric Dowdy, Steven Pfeiffer
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Publication number: 20110282070Abstract: A benzoylpyrazole compound represented by the formula (I) or its salt: wherein R1 is alkyl or cycloalkyl, R2 is a hydrogen atom or alkyl, R3 is alkyl; cycloalkyl; haloalkyl; alkoxyalkyl; alkoxycarbonylalkyl; alkenyl; or arylalkyl which may be substituted by R8, R4 is alkyl; haloalkyl; alkoxy; halogen; nitro; cyano; alkylthio; alkylsulfinyl; or alkylsulfonyl, R5 is a hydrogen atom; alkyl; alkenyl; alkynyl; halogen; cyano; cyanoalkyl; cyanoalkeny; haloalkyl; alkoxyalkyl; haloalkoxyalkyl; amino(thiocarbonyl)alkyl which may be substituted by at least one substituent selected from alkyl, cyano, is cyanoalkyl, (alkylthio)carbonylalkyl, alkyl(thiocarbonyl)alkyl, —C(O)OR7 and —C(O)SR7; thiocyanatoalkyl; alkoxy; alkenyloxy; alkynyloxy; haloalkoxy; alkoxyalkoxy; haloalkoxyalkoxy; alkoxyhaloalkoxy; haloalkoxyhaloalkoxy; alkoxyalkoxyalkyl; alkylthio; alkoxyalkylthio; haloalkoxyalkylthio; alkoxyhaloalkylthio; haloalkoxyhaloalkylthio; alkylthioalkylthio; haloalkylthioalkylthio; alkylthiohaloalkylthio; haloalkylthiohaloType: ApplicationFiled: July 21, 2011Publication date: November 17, 2011Applicant: ISHIHARA SANGYO KAISHA, LTD.Inventors: Hiroshi SHIMOHARADA, Masamitsu Tsukamoto, Masahiko Ikeguchi, Hiroshi Kikugawa, Makiko Sano, Yoshinori Kitahara, Hidemasa Kominami, Tatsuya Okita
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Publication number: 20100292480Abstract: The invention provides synthetic processes and synthetic intermediates that can be used to prepare 4-oxoquinolone compounds having useful integrase inhibiting properties.Type: ApplicationFiled: September 11, 2008Publication date: November 18, 2010Applicant: Gilead Sciences, IncInventors: Eric Dowdy, Steven Pfeiffer
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Publication number: 20100185013Abstract: A process for forming an ?,?-unsaturated carbonyl halide in a microreactor is described. The reactants comprise an ?,?-unsaturated carboxylic acid, a halogenating agent, and a catalyst. A first inlet stream, a second inlet stream, and an optional third inlet stream flow into a reaction chamber of a flow-through microreactor to form a reaction product comprising an ?,?-unsaturated carbonyl halide.Type: ApplicationFiled: June 4, 2008Publication date: July 22, 2010Inventors: Matthew J. Pinnow, Eric R. Choban, Kim M. Vogel
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Publication number: 20100099911Abstract: 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: ApplicationFiled: February 27, 2008Publication date: April 22, 2010Applicant: Mitsui Chemicals, IncInventors: Takeshi Kobayashi, Kiyomi Kido, Akinori Nagatomo
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Publication number: 20090312569Abstract: The present invention relates to a process for the preparation of 1-(2-ethyl-butyl)-cyclohexanecarboxylic acid which is useful as an intermediate in the preparation of pharmaceutically active compounds.Type: ApplicationFiled: June 12, 2009Publication date: December 17, 2009Inventor: Bruno Lohri
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Publication number: 20090076304Abstract: The present invention discloses methods for producing a carboxylic acid chloride compound which comprises the step of reacting an alkyl-substituted cyclohexyl carboxylic acid with a chlorinating agent in the presence of a specific urea compound. According to this invention, it is possible to produce a carboxylic acid chloride compound which has high reaction speed, and whose product has high purity or high yield. Thus produced carboxylic acid chloride compound is useful as an intermediate for producing D-phenylalanine derivatives which are used as agents for treating diabetes.Type: ApplicationFiled: September 30, 2008Publication date: March 19, 2009Applicant: AJINOMOTO CO., INC.Inventors: Tatsuya Ishikawa, Shouichi Kondou, Satoji Takahashi
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Patent number: 7375253Abstract: A process for the synthesis of (per)fluorinated mono-functional carbonyl compounds having the following formula (I): F-A-RF—B—C(O)X1??(I) wherein: X1=F, CF3; A, B equal to or different from each other, are independently (per)fluoroalkylene or (per)fluorooxyalkylene groups; RF is —ORf1O— wherein Rf1=perfluoroalkylene or —ORf2, wherein Rf2 is a perfluorooxyalkylene chain; said process comprising the following steps: A) obtainment of the formula (II) mono-hypofluorite: FO—CFX2-A-RF—B—C(O)X1??(II) by partial fluorination with elemental fluorine of the carbonyl groups of the formula (III) compound: X2(O)C-A-RF—B—C(O)X1??(III) in the presence of a formula MeFy catalyst, Me being an alkaline or alkaline-earth metal or Ag, y=1 or 2; B) thermal decomposition of the compound (II) to give the compounds according to the following scheme: FO—CFX2-A-RF—B—C(O)X1 (II) - - - ?F-A-RF—B—C(O)X1 (I)+(O)CFX2.Type: GrantFiled: January 9, 2004Date of Patent: May 20, 2008Assignee: Solvay Solexis S.p.A.Inventors: Giovanni Fontana, Walter Navarrini
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Patent number: 7034181Abstract: The invention relates to a method for producing o-chloromethyl benzoic acid chlorides of formula (I), in which R1 to R4 can be the same or different and represent hydrogen C1–C4 alkyl, halogen or trifluoromethyl, by reaction benzo condensed lactones of formula (II), in which R1 to R4 have the above-mentioned meaning, with thionyl chloride. The inventive method is characterized in that the reaction is carried out in the presence of catalytic quantities of a Lewis acid and in the presence of catalytic quantities of a phosphine derivative.Type: GrantFiled: November 27, 2000Date of Patent: April 25, 2006Assignee: BASF AktiengesellschaftInventors: Roland Götz, Norbert Götz, Michael Keil, Bernd Wolf, Adrian Steinmetz, Armin Stamm, Jochem Henkelmann
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Patent number: 6951957Abstract: The invention provides a process for producing a fluorine-containing compound from an inexpensive material. Namely, Compound I such as RACH2OH is reacted with Compound II such as XCORB to form Compound III such as RACH2OCORB, followed by fluorination in a liquid phase to form Compound IV such as RAFCF2OCORBF, which is converted to Compound V such as RAFCOF and/or Compound VI such as RBFCOF. RA is an alkyl group or the like, RB is a perhalogenoalkyl group or the like, RAF and RBF are fluorinated RA and RB, and X is halogen.Type: GrantFiled: April 24, 2003Date of Patent: October 4, 2005Assignee: Asahi Glass Company, LimitedInventors: Takashi Okazoe, Kunio Watanabe, Shin Tatematsu, Hidenobu Murofushi
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Patent number: 6844468Abstract: The present invention relates to a process for preparing substituted benzoyl chlorides of the formula (1) where R, x and y have the meaning given below, which comprises reacting a benzaldehyde of the formula (2) where R, independently of each other, is identical or different and is an unsubstituted phenyl radical or a phenyl radical that is substituted by halogen, NO2, CN, (C1-C4)alkyl or (C1-C4)alkoxy, or is halogen, NO2, CN, NR?2, OR?, SO2R?, SO2OR?, COR? or CO2R?, where R? is an unbranched or branched C1-C10 alkyl radical, an unsubstituted phenyl radical or a phenyl radical which is substituted by halogen, NO2, CN, (C1-C4)alkyl or (C1-C4)alkoxy, x is 1 or 2 and y is 1, 2 or 3, with a chlorinating agent in the presence of a free-radical initiator and a solvent at from ?20 to +200° C.Type: GrantFiled: October 3, 2002Date of Patent: January 18, 2005Assignee: Clariant GmbHInventors: Lars Bierer, Joachim Ritzer, Berthold Schiemenz, Thomas Wessel
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Publication number: 20040171849Abstract: The present invention provides an efficient, simple, and commercially advantageous process for producing optically active azetidine-2-carboxylic acid, which is an important material for medicines.Type: ApplicationFiled: January 14, 2004Publication date: September 2, 2004Inventors: Takeshi Kondo, Noboru Ueyama
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Publication number: 20040024250Abstract: A perfluoropolyether and a composition comprising the perfluoropolyether are provided in which the perfluoropolyether comprises at least one bromine or iodine atom at the primary position of the perfluoropolyether. Also provided is a process for producing the composition in which the process comprises contacting a perfluoropolyether acid fluoride moiety with a metal bromide or metal iodide or a suitable polyether secondary iodide under a condition sufficient to effect the production of a perfluoropolyether comprising at least one bromine or iodine at the primary position.Type: ApplicationFiled: July 25, 2003Publication date: February 5, 2004Inventors: Jon L. Howell, Erik W. Perez, Alfred Waterfeld, Chadron Mark Friesen, Joseph Stuart Thrasher, Ireneusz Nowak
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Patent number: 6677479Abstract: Compounds of the formula (I) and also process for preparing them where substituents X1, X2, Y and Z are defined as follows: X1 is H or F X2 is H or F Y is CI, Br, or I Z is CHO or COOH or CN n is 0 or 1 and also their use as starting material for preparing agrochemicals, electronics materials and pharmaceuticals.Type: GrantFiled: November 12, 2002Date of Patent: January 13, 2004Assignee: Clariant Finance LBVI LimitedInventors: Wolfgang Schmidt, Rainer Wingen
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Patent number: 6605743Abstract: The invention relates to a continuous process for the preparation of pivaloyl chloride and of aroyl chloride, in particular of benzoyl chloride, which consists in reacting pivalic acid with a trichloromethylated aromatic compound in the presence of a catalyst at a temperature of between 60° C. and 180° C. under reduced pressure. The products formed are continuously removed from the reaction region, the hydrogen chloride formed being treated in a washing region in which a trichloromethylated compound moves countercurrentwise.Type: GrantFiled: December 23, 1998Date of Patent: August 12, 2003Assignee: Elf Atochem S.A.Inventors: Christophe Ruppin, Philippe Corbiere
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Publication number: 20030130537Abstract: The present invention relates to a process for preparing substituted benzoyl chlorides of the formula (1) 1Type: ApplicationFiled: October 3, 2002Publication date: July 10, 2003Applicant: Clariant GmbHInventors: Lars Bierer, Joachim Ritzer, Berthold Schiemenz, Thomas Wessel
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Patent number: 6586626Abstract: The invention provides a process for producing a fluorine-containing compound from an inexpensive material. Namely, Compound I such as RACH2OH is reacted with Compound II such as XCORB to form Compound III such as RACH2OCORB, followed by fluorination in a liquid phase to form Compound IV such as RAFCF2OCORBF, which is converted to Compound V such as RAFCOF and/or Compound VI such as RBFCOF. RA is an alkyl group or the like, RB is a perhalogenoalkyl group or the like, RAF and RBF are fluorinated RA and RB, and X is halogen.Type: GrantFiled: September 24, 2001Date of Patent: July 1, 2003Assignee: Asahi Glass Company, LimitedInventors: Takashi Okazoe, Kunio Watanabe, Shin Tatematsu, Hidenobu Murofushi
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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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Publication number: 20020040158Abstract: The present invention relates to a process for preparing substituted benzoyl chlorides of the formula (1) 1Type: ApplicationFiled: July 26, 2001Publication date: April 4, 2002Applicant: Clariant GmbHInventors: Lars Bierer, Joachim Ritzer, Berthold Schiemenz, Thomas Wessel
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Patent number: 6329529Abstract: Disclosed are a fluorinating agent represented by the general formula (1): wherein R1 to R4 are a substituted or unsubstituted, saturated or unsaturated alkyl group or a substituted or unsubstituted aryl group, and can be the same or different; R1 and R2 or R3 and R4 can bond to form a ring including a nitrogen atom or a nitrogen atom and other hetero atoms; or R1 and R3 can bond to form a ring including a nitrogen atom or a nitrogen atom and other hetero atoms, for example: a preparation process of the fluorinating agent and a process for preparing fluorine compounds by reacting various compounds with the fluorinating agent. The invention has also disclosed that the fluorinating agent is very effective for fluorinating oxygen containing functional compounds.Type: GrantFiled: July 31, 1998Date of Patent: December 11, 2001Assignee: Mitsui Chemicals, Inc.Inventors: Hiroshi Sonoda, Kazunari Okada, Akira Takahashi, Kouki Fukumura, Hidetoshi Hayashi, Teruyuki Nagata, Yasuhiro Takano
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Patent number: 6313337Abstract: A method of making a benzoyl halide is disclosed. Into a reactor is placed a reaction mixture of a benzotrihalide and a benzaldehyde having the respective general formulas where each A is independently selected from halogen, CF3, R, or OR, each B is independently selected from halogen, CF3, or R, R is alkyl from C1 to C10 or aryl from C6 to C12, each X is independently selected from Cl and Br, m is 0 to 3, and n is 0 to 2. Also added is at least about 10 ppm of a catalyst selected from the group consisting of zinc salts and copper salts, and an optional solvent. The addition of an ammonium halide to the product mixture forms the corresponding amide, which can be dehydrated to form the corresponding nitrile.Type: GrantFiled: April 17, 2000Date of Patent: November 6, 2001Assignee: Occidental Chemical CorporationInventors: Dean R. Lagerwall, Daniel R. Thielen, Pravin M. Khandare, Mark F. Lechner
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Patent number: 6201152Abstract: Disclosed is a method of making 3,5-dichloro-p-toluoyl chloride. A mixture is prepared of methyl-3,5-dichloro-4-methylbenzoate, about 1 to about 1.4 equivalents of an &agr;,&agr;,&agr;-trichloromethylbenzene, and about 0.01 to about 0.2 equivalents of a catalyst selected from the group consisting of ammonium septamolybdate, ammonium dimolybdate, and mixtures thereof. The mixture is heated to a temperature of about 150 to about 180° C.Type: GrantFiled: November 5, 1999Date of Patent: March 13, 2001Assignee: Occidental Chemical CorporationInventors: Michael J. Fifolt, Sanjay Mandal, William S. Derwin
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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: 5919341Abstract: A process for preparing chlorodifluoroacetyl chloride from 1,1-difluoro-2,2-dichloroethylene and dichloroacetyl chloride from trichloroethylene or 1,1,2,2-tetrachloroethane, in which the starting compounds are continuously reacted in the gaseous phase with oxygen to obtain a photochemical oxidation reaction, chlorine being added as a sensitizer, the reaction mixture being irradiated with light having a wavelength .lambda..gtoreq.280 nm, the reaction preferably being carried out unpressurized. Particularly high yields with height selectivity are achieved by using doped high pressure mercury vapor lamps to irradiate the reaction mixture.Type: GrantFiled: December 23, 1997Date of Patent: July 6, 1999Assignee: Solvay Fluor und Derivate GmbHInventors: Max Braun, Werner Rudolph, Kerstin Eichholz
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Patent number: 5912371Abstract: 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: GrantFiled: October 27, 1997Date of Patent: June 15, 1999Assignee: Dow Corning Toray Silicone Co., Ltd.Inventors: Koji Nakanishi, Tadashi Okawa
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Patent number: 5905169Abstract: A process is disclosed for preparing polyhaloacyl fluorides such as trifluoroacetyl fluoride and difluoroacetyl fluoride by oxidizing 1-chloro-1,2,2,2-trifluoroethanes and 1,1-dichloro-2,2-difluoroethane, respectively with oxygen.Type: GrantFiled: March 20, 1995Date of Patent: May 18, 1999Assignee: E. I. Du Pont De Nemours and CompanyInventor: Stephen Ernest Jacobson
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Patent number: 5750779Abstract: 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: GrantFiled: May 31, 1996Date of Patent: May 12, 1998Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Teruyuki Nagata, Hidetoshi Hayashi, Hideki Mizuta
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Patent number: 5623082Abstract: Acyl chlorides are prepared by reacting a carboxylic acid or its anhydride with carbonyl chloride in the presence of a carboxamide of the formula I ##STR1## where R.sup.1 is a radical of the formula ##STR2## R.sup.2 and R.sup.3 are each alkyl of 1 to 9 carbon atoms, R.sup.4 and R.sup.5 are each hydrogen or alkyl of 1 to 9 carbon atoms and the two radicals R.sup.1 and R.sup.2 may furthermore be a hydrocarbon radical which completes the moiety ##STR3## to form a heterocyclic structure, and the stated alkyl and hydrocarbon radicals may furthermore contain substituents which are inert under the reaction conditions.Type: GrantFiled: July 11, 1995Date of Patent: April 22, 1997Assignee: BASF AktiengesellschaftInventors: Martin Decker, Wolfgang Franzischka, Rudolf Irnich, deceased, Manfred Sauerwald
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Patent number: 5616787Abstract: The invention relates to a process for the preparation of polyalkylated aromatic carboxylic acids of formula I ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are each independently of one another hydrogen, C.sub.1 -C.sub.20 alkyl, halogen or C.sub.5 -C.sub.8 cycloalkyl, with the proviso that at least two of the substituents R.sub.1, R.sub.2, R.sub.3, R.sub.4 or R.sub.5 are alkyl and/or cycloalkyl, by reacting corresponding aromatic hydrocarbons with carbon dioxide, which reaction is carried out observing special ratios of temperature and pressure. The invention furthermore relates to a one-pot process for the preparation of the corresponding acyl halides.Type: GrantFiled: October 11, 1995Date of Patent: April 1, 1997Assignee: Ciba-Geigy CorporationInventors: Rinaldo Husler, Ivan Orban, Martin Holer
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Patent number: 5543568Abstract: 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: GrantFiled: September 7, 1993Date of Patent: August 6, 1996Assignee: BASF AktiengesellschaftInventors: Jochem Henkelmann, Lutz Tietze
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Patent number: 5532411Abstract: A process for preparing carboxylic acid halides and carboxylate salts by reacting metal or "onium" halides with carboxylic anhydrides, which process is very suitable for working-up anhydrous, spent catalyst preparations. The resulting carboxylic acid halide or carboxylate salt can be used as an acylating reagent or alkylating reagent, and metal halide or "onium" halide liberated during this can be reacted anew with carboxylic anhydride and regenerated, thereby making it possible to effect a hydrolysis-free alkylation or acylation without forming salt-type waste products. If the mixture of carboxylic acid halide and carboxylate salt is allowed to react with an alcohol, preferably in situ, the resulting ester can be isolated without hydrolysis.Type: GrantFiled: April 26, 1994Date of Patent: July 2, 1996Assignee: Solvay Fluor und Derivate GmbHInventors: Max Braun, Werner Rudolph, Stefan Palsherm, Kerstin Eichholz
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Patent number: 5506358Abstract: There is disclosed a process for producing an alkoxyiminoacetamide compound which is useful as agricultural fungicides. Also dislclosed are novel intermediate compounds for the above process and their production.Type: GrantFiled: March 8, 1994Date of Patent: April 9, 1996Assignee: Shionogi & Co., Ltd.Inventors: Akira Takase, Hiroyuki Kai, Moriyasu Masui, Kazuo Ueda, Tsuneo Iwakawa
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Patent number: 5504245Abstract: Disclosed is a process for the preparation of cyclopropanecarboxylic acid by the non-catalytic, oxidation of cyclopropanecarboxaldehyde using molecular oxygen as the oxidant. Also disclosed are processes for the preparation of amides, esters and acid chlorides from cyclopropanecarboxylic acid.Type: GrantFiled: September 30, 1994Date of Patent: April 2, 1996Assignee: Eastman Chemical CompanyInventors: Shaowo Liang, Timothy W. Price
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Patent number: 5504249Abstract: A process for preparing o-chloromethylbenzoyl chlorides of the formula I ##STR1## where m is 0 or an integer from 1 to 4 andX is halogen or C-organic radicals,entails reacting a corresponding lactone of the formula II ##STR2## with thionyl chloride in the presence of a catalyst.Type: GrantFiled: March 31, 1995Date of Patent: April 2, 1996Assignee: BASF AktiengesellschaftInventors: Heinz Isak, Herbert Bayer, Michael Keil, Thomas Wettling
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Patent number: 5493054Abstract: The subject of the present invention is a new catalytic system and a process for the synthesis of acid halides, especially from haloforms. This process for halogenating by means of a haloform is characterized by the use of a metal chloride, advantageously trivalent, as a catalyst, the solubility of which in the reaction mixture is at least equal to one millimole, preferably 1/100 mole per liter, and the metal chloride also being at least half, advantageously two-thirds and preferably three-quarters in the dissolved state.Type: GrantFiled: September 27, 1994Date of Patent: February 20, 1996Assignee: Rhone-Poulenc ChimieInventors: Gerard Forat, Laurent Gilbert
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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: 5395966Abstract: Acryloyl chloride is obtained by reaction of acrylic acid with phenylchloroform in the presence of at least one Lewis acid as catalyst and of at least one polymerization inhibitor. According to the invention the catalyst is chosen from zinc oxide and zirconium tetrachloride and the reaction is conducted at a temperature of at least 105.degree. C. In a preferred embodiment acrylic acid is added to the mixture consisting of phenylchloroform, the catalyst and the polymerization inhibitor and heated to a temperature of at least 105.degree. C., the acryloyl chloride formed distilling off as soon as the introduction of acrylic acid begins.Acryloyl chloride is a highly reactive synthesis intermediate.Type: GrantFiled: July 22, 1994Date of Patent: March 7, 1995Assignee: AtochemInventors: Jean-Francois Croizy, Paul Grosius
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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