Elemental Halogen Or Hydrogen Halide Utilized Patents (Class 562/863)
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Patent number: 8455684Abstract: A method for converting an aromatic aldehyde or a mixture of aromatic aldehydes to a reaction product in a reaction medium that is free from xylene. The reaction product may be an aromatic acyl halide or a mixture of aromatic acyl halides. The method includes bringing the aromatic aldehyde or mixture of aromatic aldehydes in contact with a halogen to obtain the reaction product.Type: GrantFiled: March 10, 2010Date of Patent: June 4, 2013Assignee: Teijin Aramid B.V.Inventors: Hendrikus Bekx, Henk Knoester
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Patent number: 8350082Abstract: This process for producing fluorine-containing compounds includes liquid-phase fluorination by introducing a raw material compound and fluorine gas into a solvent to replace hydrogen atoms in the raw material compound with fluorine atoms. More specifically, the process for producing fluorine-containing compounds includes (1) promoting fluorination by dissolving the raw material compound in anhydrous hydrofluoric acid and introducing into a liquid-phase fluorination solvent, or (2) promoting fluorination by dissolving the raw material compound in a perfluoro compound having a plurality of polar groups in a molecule thereof and introducing into a liquid-phase fluorination solvent. According to these processes, a fluorination reaction can be carried out at high yield and without containing hardly any isomers while using a hydrocarbon compound as is for the raw material.Type: GrantFiled: November 28, 2008Date of Patent: January 8, 2013Assignees: Mitsubishi Materials Corporation, Mitsubishi Materials Electronic Chemicals Co., Ltd.Inventors: Mitsuo Kurumaya, Tsunetoshi Honda, Kota Omori
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Patent number: 8232416Abstract: A method of manufacturing a compound represented by formula (2) is provided, the method including thermally decomposing a compound represented by formula (1) under a reduced pressure: wherein Rf1 and Rf2 each independently represents a fluorine atom or a perfluorinated monovalent substituent, Rf3 and Rf4 each independently represents a fluorine atom, a perfluorinated monovalent substituent or a perfluorinated divalent substituent, Rf3 and Rf4 may combine with each other to form a ring, each of Rf3 and Rf4 may combine with Rf5 to form a ring, and Rf5 represents a perfluorinated (n+1)-valent to (2n+2)-valent linkage group, provided that n represents an integer of 1 to 5.Type: GrantFiled: February 25, 2009Date of Patent: July 31, 2012Assignee: FUJIFILM CorporationInventors: Hiroki Sugiura, Masayuki Harada
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Patent number: 6956138Abstract: The present invention provides a method for obtaining a compound useful as a raw material for various fluororesins in high yield by a short process by using a starting material which is inexpensive and readily available.Type: GrantFiled: April 28, 2004Date of Patent: October 18, 2005Assignee: Asahi Glass Company, LimitedInventors: Takashi Okazoe, Kunio Watanabe, Shin Tatematsu, Masahiro Ito, Daisuke Shirakawa, Masao Iwaya, Hidekazu Okamoto
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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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Patent number: 6833477Abstract: The process for producing a vic-dichloro acid fluoride compound in a short process and in good yield from the starting material which is inexpensive and readily available is provided. (RH1—EH1—)CRH2RH3CH2—OCORHB (I) is fluorinated in a liquid phase to form (CF2ClCFCl—EFF1—) CRF2RF3CF2—OCORFB (II), and then, an ester bond of the compound (II) is decomposed to form (CF2ClCFCl—EF1—)CRF2RF3COF(III) or the compound (III) and FCORFB (IV).Type: GrantFiled: February 28, 2002Date of Patent: December 21, 2004Assignee: Asahi Glass Company, LimitedInventors: Takashi Okazoe, Kunio Watanabe, Masahiro Ito, Daisuke Shirakawa, Shin Tatematsu
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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: 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: 6255524Abstract: An acid chloride can be produced at a high yield from a primary alcohol having a polyfluoroalkyl group and one methylene group by (1) a method in which RfCH2OH (wherein Rf is a polyfluoroalkyl group) is reacted with chlorine to produce RfCOCl, (2) a method in which RfCHO is reacted with chlorine to produce RfCOCl, and (3) a method for producing an acid chloride comprising (a) a step in which an aldehyde (RfCHO) is formed from an alcohol (RfCH2OH), (b) a step in which a monochloroester (RfCOOCHClRf) is formed from the aldehyde and an acid chloride (RfCOCl), and (c) a step in which the acid chloride (RfCOCl) is formed from the monochloroester.Type: GrantFiled: June 25, 1999Date of Patent: July 3, 2001Assignee: Daikin Industries Ltd.Inventors: Hirokazu Aoyama, Shoji Takagi, Shinichi Matsumura, Yoshinori Tanaka
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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: 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: 5872290Abstract: Disclosed is a method of making an acid chloride having the general formula ##STR1## where each R contains no unsaturated groups and is preferably independently selected from aliphatic from C.sub.1 to C.sub.7 and aryl from C.sub.6 to C.sub.15. A solution is formed in an inert solvent of an aldehyde having the general formula ##STR2## and chlorine gas is sparged into said solution. The reaction between the aldehyde and the chlorine gas to produce the acid chloride is performed in the absence of a catalyst, an initiator, and ultraviolet light. A chlorinated acid chloride can be prepared from the acid chloride by reacting it with additional chlorine in the presence of a chlorine free radical generator.Type: GrantFiled: November 7, 1997Date of Patent: February 16, 1999Assignee: Occidental Chemical CorporationInventors: James G. Colson, Ramesh Krishnamurti, Rose Adinolfe
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Patent number: 5872291Abstract: Provided is a process for producing benzoyl chlorides which comprises reacting an aromatic aldehyde with chlorine in liquid phase in the presence of inert gas, whereby the generation of benzal chlorides by products whose separation is difficult can be suppressed.Type: GrantFiled: December 18, 1997Date of Patent: February 16, 1999Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Takeshi Koshikawa, Toshihiro Hashimoto, Makoto Takagawa
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Patent number: 5672749Abstract: The yield of acetyl chloride from the reaction between acetic anhydride and hydrogen chloride is increased by withdrawing acetyl chloride, optionally together with at least some of the acetic acid by-product, from the reaction mixture as the reaction proceeds and recycling the remainder of the reaction mixture to the reactor for reaction with additional hydrogen chloride.Type: GrantFiled: April 9, 1996Date of Patent: September 30, 1997Assignee: Albemarle CorporationInventors: W. Bryan Waites, Robert E. Young, Phillip R. DeVrou
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Patent number: 5599981Abstract: Provided is a process for producing alkylbenzoyl chloride which comprises reacting alkylbenzaldehyde with chlorine at a temperature of -10.degree. to 80.degree. C. under a pressure of 5 kg/cm.sup.2 or below in a liquid phase, whereby alkylbenzoyl chloride can be produced in a high yield and at a low price.Type: GrantFiled: January 24, 1996Date of Patent: February 4, 1997Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Norio Fushimi, Kenichi Nakamura, Makoto Takagawa
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Patent number: 5569782Abstract: A process for preparing polyfluorochloro- and perfluorocarbonyl chlorides, for example for preparing perfluoropropionyl chloride, chlorodifluoroacetyl chloride or trifluoroacetyl chloride, in which starting materials are employed which have a CHCl.sub.2 group which is converted to a C(O)Cl group by photochemical oxidation with oxygen in the presence of added elemental chlorine and under exposure to activating irradiation by light having a wavelength .lambda..gtoreq.290 nm. The procedure is preferably unpressurized. Outstanding conversions with high selectivity are achieved using doped Hg light sources.Type: GrantFiled: December 20, 1994Date of Patent: October 29, 1996Assignee: Solvay Fluor und Derivate GmbHInventors: Max Braun, Werner Rudolph, 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: 5504250Abstract: The invention relates to a process for the preparation of D-(-)-phenylglycine chloride hydrochloride by chlorinating D-(-)-phenylglycine hydrochloride, which as such is prepared in situ from D-(-)-phenylglycine and hydrochloric acid gas, in a solvent. According to the invention chlorination of the hydrochloride is carried out in a non-chlorinated solvent or a mixture of non-chlorinated solvents in the presence of a reaction promoting medium.Chlorination is carried out through the addition of PCl.sub.5, but preferably the PCl.sub.5 is prepared in situ from PCl.sub.3 and Cl.sub.2 gas.Type: GrantFiled: February 28, 1994Date of Patent: April 2, 1996Assignee: Westpur Investments LimitedInventor: Raoul Kessels
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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: 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: 5296640Abstract: A process for preparing perhaloacyl chlorides such as trifluoroacetyl chloride by oxidizing lower perfluoroalkyl and monochloroperfluoroalkyl dichloromethane within the supercritical region and in the absence of water.Type: GrantFiled: September 15, 1992Date of Patent: March 22, 1994Assignee: E. I. Du Pont de Nemours and CompanyInventors: Stephen E. Jacobson, Wayne B. Ely
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Patent number: 5037512Abstract: A process for the purification of crude benzoic acid obtained by the catalytic oxidation of toluene in the liquid phase, which is contaminated with impurities including phthalic acid and benzylbenzoate, the process involves distilling the crude benzoic acid in a first distillation in the presence of an aliphatic amine or a mixture of aliphatic amines of the formulaHNR.sup.1 R.sup.2whereinR.sup.1 represents hydrogen or a straight-chain or branched hydroxyalkyl or aminoalkyl radical with 1 to 6 carbon atoms andR.sup.2 represents a straight-chain or branched hydroxyalkyl or aminoalkyl radical with 1 to 6 carbon atoms,and/or the salts of these amines, recovering from this distillation (a) a purified benzoic acid and (b) a benzylbenzoate containing residue, working up the residue by a second distillation and chlorinating the distillate resulting from this second distillation to give a benzoylchloride virtually free of benzonitrile.Type: GrantFiled: August 17, 1989Date of Patent: August 6, 1991Assignee: Bayer AktiengesellschaftInventor: Werner Schulte-Huermann
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Patent number: 4990661Abstract: A process for the preparation of a compound of the formula ##STR1## in which X.sup.1 and X.sup.2 each independently is chlorine or fluorine, andY is chlorine, bromine, fluorine or iodine, comprising subjecting a compound of the formula ##STR2## to a Sandmeyer or Balz-Schiemann reaction thereby to produce a carboxylic acid of the formula ##STR3## and converting the carboxylic acid (Ia) into an acyl chloride of the formula ##STR4## The compound (II) is new. The products are known intermediates for anti-bacterials.Type: GrantFiled: March 29, 1989Date of Patent: February 5, 1991Assignee: Bayer AktiengesellschaftInventors: Uwe Petersen, Michael Schriewer, Ernst Kysela, Klaus Grohe
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Patent number: 4968852Abstract: A novel compound, trifluoromethylbenzoyl bromide, is formed by bromination of trifluoromethylbenzoic acid with, e.g., phosphorus tribromide or by halogen exchange reaction of trifluoromethylbenzoyl chloride with bromine in the presence of a metal bromide. Decarbonylation of 2-, 3- or 4-trifluoromethylbenozyl bromide using a catalyst such as a phosphine-rhodium complex gives 2-, 3- or 4-bromobenzotrifluoride without forming isomers.Type: GrantFiled: December 28, 1989Date of Patent: November 6, 1990Assignee: Central Glass Company, LimitedInventors: Toshikazu Kawai, Hideki Oshio
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Patent number: 4851160Abstract: A process for the preparation of a compound of the formula ##STR1## in which X.sup.1 and X.sup.2 each independently is chlorine or fluorine, andY is chlorine, bromine, fluorine or iodine, comprising subjecting a compound of the formula ##STR2## to a Sandmeyer or Balz-Schiemann reaction thereby to produce a carboxylic acid of the formula ##STR3## and converting the carboxylic acid (Ia) into an acyl chloride of the formula ##STR4## The compound (II) is new. The products are known intermediates for anti-bacterials.Type: GrantFiled: August 28, 1987Date of Patent: July 25, 1989Assignee: Bayer AktiengesellschaftInventors: Uwe Petersen, Michael Schriewer, Ernst Kysela, Klaus Grohe