Bonding Haloalkyl Group Directly To Benzene Ring Patents (Class 570/194)
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Patent number: 9067857Abstract: A method of manufacturing a fluorine-containing aromatic compound represented by the following formula (2-1) or formula (2-2): [R is a hydrogen atom, an alkyl group having a carbon number of 1 to 12 which may have a substituent other than a fluorine atom, or a monovalent aromatic group which may have a substituent; Rf1 and Rf2 are a fluorine-containing alkyl group having a carbon number of 1 to 12 and Rf1 and Rf2 may be the same or different; and m is an integer of 1 or more, n is an integer of 0 or more and m+n is an integer of 1 or more and 5 or less].Type: GrantFiled: August 13, 2014Date of Patent: June 30, 2015Assignee: ASAHI GLASS COMPANY, LIMITEDInventors: Tomoko Yajima, Kyoko Yamamoto
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Patent number: 8664424Abstract: Provided is a method for preparing 2,5-dimethylphenylacetic acid, wherein p-xylene is mixed with paraformaldehyde and concentrated hydrochloric acid in a solvent of ion liquid to obtain 2,5-dimethyl benzyl chloride by the chloromethylation reaction. Then, 2,5-dimethyl benzyl chloride is introduced into a reactor with an acid binding agent and a solvent, the carbonylation and hydrolysis reaction is conducted in the presence of a catalyst to obtain 2,5-dimethylphenylacetic acid. The present process has new route, less synthesis steps, simple operation, lower cost, increased yield, and is friendly to the environment. Therefore, the method is suitable for industrial production.Type: GrantFiled: June 7, 2011Date of Patent: March 4, 2014Assignees: Lianhe Chemical Technology Co., Ltd, Jiangsu Lianhe Chemical Technology Co., Ltd.Inventors: Ping Wang, Xiaobin Fan, Xingjun Lin, Zhaohui He
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Publication number: 20100234651Abstract: The present invention relates to novel 2-bromo-2,2-dichloroethyl aromatics of the formula (V) in which Ar is as defined above and to processes for preparation thereof.Type: ApplicationFiled: March 16, 2010Publication date: September 16, 2010Applicant: Bayer CropScience AGInventor: Thomas HIMMLER
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Patent number: 7304192Abstract: The present invention relates to a simple method for efficiently producing aromatic-substituted chlorinated hydrocarbons, for example, high-purity cumyl chloride (1,4-bis(1-chloro-1-methylethyl)benzene, p-DCC) that can be used as an initiator for cationic polymerization. A corresponding tertiary alcohol such as 1,4-bis(1-hydroxy-1-methylethyl)benzene is mixed with aqueous hydrochloric acid and subjected to stirring, and then the resulting organic layer is brought into contact with a hydrogen chloride gas to produce high-quality aromatic-substituted chlorinated hydrocarbon in high yield. Furthermore, in order to purify a mixture containing a chlorinated hydrocarbon compound, the mixture being produced by reaction between an aqueous solution of a metal hypochiorite and a protonic acid, the mixture is allowed to react with an aqueous alkaline solution to form an alcohol compound. Then, a solid is isolated by solid-liquid separation and chlorinated again with the aqueous hydrochloric acid.Type: GrantFiled: July 2, 2003Date of Patent: December 4, 2007Assignee: Kaneka CorporationInventors: Takeshi Kawamura, Chiho Yoshimi, Hidetoshi Odaka
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Patent number: 7060862Abstract: A method of synthesizing a high purity product of ?,?,??,??-tetrachloro-p-xylene is disclosed. The method includes carrying out a first stage reaction of terephthaldicarboxaldehyde with a mixture of SOCl2 and dimethylformamide (DMF) to obtain a product mixture containing ?,?,??,??-tetrachloro-p-xylene as a major product and 4-dichloromethyl benzaldehyde as a side product; adding SOCl2 and DMF to the product mixture of the first stage reaction to undergo a second stage reaction; and to a cool water adding the resulting product mixture from the second stage reaction to obtain a solid product of ?,?,??,??-tetrachloro-p-xylene with a purity of 90-99 mol %.Type: GrantFiled: December 30, 2003Date of Patent: June 13, 2006Assignee: Chung-Shan Institute of Science & TechnologyInventors: Shean-Jeng Jong, Chun-Hsu Lin, Chao-chou Tu, Chung-Chien Chang
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Patent number: 7026522Abstract: Disclosed is a process for the production of 2-amino-2-[2-(4-C2-20-alkyl-phenyl)ethyl]propane-1,3-diols.Type: GrantFiled: June 18, 2003Date of Patent: April 11, 2006Assignee: Novartis AGInventors: Stephan Abel, Tetsuro Fujita, Ryoji Hirose, Guido Jordine, Tadashi Mishina
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Patent number: 6992231Abstract: A synthesis method of ?,?,??,??-tetrachloro-p-xylene is disclosed. The method includes reacting terephthaldicarboxaldehyde with a mixture of SOCl2 and dimethylformamide (DMF) to obtain a product mixture containing ?,?,??,??-tetrachloro-p-xylene as a major product and 4-dichloromethyl benzaldehyde as a side product, which can be separated by silica column chromatography.Type: GrantFiled: December 30, 2003Date of Patent: January 31, 2006Assignee: Chung-Shan Institute of Science & TechnologyInventors: Shean-Jeng Jong, Chun-Hsu Lin, Ming-Te Shih, Chung-Chien Chang
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Patent number: 6861566Abstract: There is provided an industrially advantageous process for producing a 1-chloro-4-arylbutane represented by the general formula (2): wherein R represents hydrogen, lower alkyl, or lower alkoxy, characterized by reacting 1-bromo-3-chloropropane with a compound represented by the general formula (1): wherein R is as defined above; and X represents chlorine, bromine, or iodine, in a solvent.Type: GrantFiled: March 11, 2002Date of Patent: March 1, 2005Assignees: Sumitomo Chemical Company, Limited, Ono Pharmaceutical Co., Ltd.Inventors: Hiroaki Hibino, Susumu Ohtsuka, Yasunobu Miyamoto, Itsuo Okumoto
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Patent number: 6265628Abstract: In a process for the continuous preparation of mono- and/or bis(mono- and/or di- and/or trichloromethyl) benzenes by gradual chlorination of the corresponding mono-or dimethylbenzenes in several reactors in cascade, the first reactor has a greater volume than each of the other reactors.Type: GrantFiled: April 9, 1999Date of Patent: July 24, 2001Assignee: Elf Atochem, S.A.Inventors: Raymond Commandeur, RĂ©gis Loze
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Patent number: 5710355Abstract: Disclosed is a method of making a chlorobenzene having the general formulas ##STR1## where X is Cl or F, and X' is X or CF.sub.3. A compound having the formula ##STR2## is sulfonated using at least 2 moles per mole of said compound of a sulfonating agent selected from the group consisting of sulfuric acid, chlorosulfonic acid, and mixtures thereof, to produce a sulfonated compound. The sulfonated compound is chlorodesulfonated to produce a chlorobenzene, such as 1,2,4-trichlorobenzene. Preferably, the starting material is ortho-dichlorobenzene.Type: GrantFiled: June 10, 1996Date of Patent: January 20, 1998Assignee: Occidental Chemical CorporationInventor: Ramesh Krishnamurti
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Patent number: 5136114Abstract: The invention relates to a new process for the preparation of geminal diarylalkanes of the formula ##STR1## by Friedel-Crafts alkylation of aromatic compounds with specific aliphatic halogen compounds (addition compounds of CCl.sub.4 , to .alpha.-olefins), to new geminal diarylalkanes and the aralkyl compounds resulting as intermediates.Type: GrantFiled: April 30, 1990Date of Patent: August 4, 1992Assignee: Bayer AktiengesellschaftInventor: Dieter Arlt
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Patent number: 5099083Abstract: 3-chloromethylbenzocyclobutene is prepared by reacting benzocyclobutene with chloromethyl methyl ether in the presence of stannic chloride at a temperature of about -120.degree. C. to about -40.degree. C. and neutralizing the resulting reaction mixture comprising 3-chloromethylbenzocyclobutene at a temperature of about -80.degree. C. to about -70.degree. C.Type: GrantFiled: February 14, 1991Date of Patent: March 24, 1992Assignee: The Dow Chemical CompanyInventors: P. J. Thomas, R. Garth Pews
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Patent number: 5030777Abstract: A process for synthesizing 3,5-dichloroalkylbenzene and recovering 1,3-dichlorobenzene from a starting mixture of 1,3- and 1,4-dichlorobenzenes. The process includes the sequential steps of selectively alkylating the 1,3-dichlorobenzene in the starting mixture; isomerizing a portion of the 2,4-dichloroalkylbenzene produced to 3,5-dichloroalkylbenzene; separating the 1,4-dichlorobenzene from the isomeric mixture of dichlorocumenes; and selectively transalkylating the dichlorocumenes to yield alkylbenzene, 3,5-dichloroalkylbenzene and 1,3-dichlorobenzene. By selectively alkylating only a portion of the 1,3-dichlorobenzene, the reaction products are obtained in good yield and substantially free of undesirable by-products.Type: GrantFiled: October 31, 1989Date of Patent: July 9, 1991Assignee: Standard Chlorine of Delaware, Inc.Inventors: Jacob George, Kanti B. Desai, Jimmy Peress
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Patent number: 5003116Abstract: A monoalkylaromatic hydrocarbon is haloethylated to a 1-halo-1-arylethane with minimal co-formation of diarylalkane by-product by reacting it with hydrogen chloride or bromide and acetaldehyde in the presence of sulfuric acid only until not more than about 60% of the monoalkylaromatic hydrocarbon has been converted.Type: GrantFiled: October 10, 1989Date of Patent: March 26, 1991Assignee: Ethyl CorporationInventor: Barbara C. Stahly
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Patent number: 4990704Abstract: A monoalkylaromatic hydrocarbon is haloethylated to a 1-halo-1-arylethane with minimal co-formation of diarylalkane and acetaldehyde by-products by reacting it with hydrogen chloride or bromide and a stoichiometric deficit of acetaldehyde in the presence of sulfuric acid in an amount such as to provide at least two mols of hydrogen sulfate per mol of acetaldehyde and less than 1.5 mols of hydrogen sulfate per mol of the monoalkylaromatic hydrocarbon.Type: GrantFiled: October 10, 1989Date of Patent: February 5, 1991Assignee: Ethyl CorporationInventor: Barbara C. Stahly
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Patent number: 4967026Abstract: A process is described for preparing chloromethyl phenethyl bromide, in which phenethyl bromide is reacted with HCl and formaldehyde in the presence of zinc chloride as the catalyst, and in a chlorinated hydrocarbon as the solvent. The product is produced in yields in excess of 70%, the para isomer constituting more than 75% of the product which contains a mixture of ortho, meta and para isomers.Type: GrantFiled: May 11, 1989Date of Patent: October 30, 1990Assignee: Bromine Compounds Ltd.Inventor: Stephen Daren
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Patent number: 4876404Abstract: Dichlorotrifluoromethyltoluenes useful in producing some medicines and agricultural chemicals are formed with good yields by reacting dichlorotrichloromethyltoluenes with hydrogen fluoride usually at 0.degree.-100.degree. C. under pressure of 3-20 kg/cm.sup.2. Besides known 3,4-dichloro-6-trifluoromethyltoluene and 3,4-dichloro-5-trifluoromethyltoluene, novel isomers are also obtained by this method.Type: GrantFiled: August 11, 1987Date of Patent: October 24, 1989Assignee: Central Glass Company, LimitedInventors: Takeshi Kondo, Toshikazu Kawai, Hideki Oshio
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Patent number: 4604243Abstract: An olefin, especially an activated olefin, is arylated by reaction with an arylamine, such as an aniline, in an inert polar organic solvent and in the presence of an alkyl nitrite, a hydrogen halide, and a catalytic amount of a copper catalyst having the copper in an oxidation state below +2.Type: GrantFiled: July 25, 1985Date of Patent: August 5, 1986Assignee: Ethyl CorporationInventor: Robert I. Davidson
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Patent number: 4575565Abstract: The invention herein pertains to a novel process for making substituted benzotrifluorides.Type: GrantFiled: April 15, 1985Date of Patent: March 11, 1986Assignee: Monsanto CompanyInventor: William F. Goure
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Patent number: 4563529Abstract: A trifluoromethylpyridine selected from the group consisting of .alpha.-trifluoromethylpyridine, .gamma.-trifluoromethylpyridine, a bis(trifluoromethyl)pyridine and chlorides thereof which have 1 to 3 chlorine atoms in its pyridine nucleus is produced by reacting a pyridine derivative selected from the group consisting of .alpha.-picoline, .gamma.-picoline and a lutidine with chlorine and anhydrous hydrogen fluoride at a temperature of 300.degree. to 600.degree. C. in a vapor phase in the presence of a diluent and a catalyst comprising a fluoride of a metallic element selected from the group consisting of aluminum, chromium, iron, nickel, manganese, cobalt and copper.Type: GrantFiled: June 4, 1981Date of Patent: January 7, 1986Assignee: Ishihara Sangyo Kaisha Ltd.Inventors: Ryuzo Nishiyama, Kanichi Fujikawa, Isao Yokomichi, Yasuhiro Tsujii, Shigeyuki Nishimura
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Patent number: 4562280Abstract: The invention is a process for the chloromethylation of an aromatic compound, substituted with an alkyl group and a deactivating moiety, which comprises contacting an aromatic compound, substituted with an alkyl group and a deactivating group, with a chloromethyl alkyl ether in the presence of a catalytic amount of ferric chloride or stannic chloride, under conditions such that an aromatic compound, substituted with an alkyl group, a chloromethyl group, and a deactivating group, wherein the alkyl and chloromethyl groups are on adjacent carbon atoms, is prepared.Type: GrantFiled: October 18, 1984Date of Patent: December 31, 1985Assignee: The Dow Chemical CompanyInventors: Jo Ann Gilpin, Lowell B. Lindy
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Patent number: 4490532Abstract: Hydrogen chloride is passed into p-xylene and acetaldehyde to form bis-1-chloroethyl ether; the latter is converted to 2-(1-chloroethyl)-1,4-dimethylbenzene by the action of sulfuric acid and hydrogen chloride. Alkali metal hydrogen sulfide in aqueous methanol or ethanol converts the 2-(1-chloroethyl)-1,4-dimethylbenzene to alpha,2,5-trimethylbenzenemethanethiol; the sodium salt of the latter reacted with 2-chloropyridine-1-oxide yields 2-[1-(2,5-dimethylphenyl)ethylthio]pyridine-1-oxide which is then oxidized with hydrogen peroxide and alkali metal tungstate or tungstic acid to form 2-[1-(2,5-dimethylphenyl)ethylsulfonyl]pyridine-1-oxide.Type: GrantFiled: July 28, 1980Date of Patent: December 25, 1984Assignee: Uniroyal Ltd.Inventor: John W. Harris
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Patent number: 4419514Abstract: Method for converting carboxylic acid groups to trichloromethyl groups which comprises contacting a compound containing a carboxylic acid group with a phenylphosphonic dichloride and phosphorus pentachloride and recovering the thus produced product.Type: GrantFiled: May 18, 1981Date of Patent: December 6, 1983Assignee: The Dow Chemical CompanyInventors: Lennon H. McKendry, Michael J. Ricks, Richard B. Rogers