Bonding Haloalkyl Group Directly To Benzene Ring Patents (Class 570/194)
  • Patent number: 9067857
    Abstract: 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: Grant
    Filed: August 13, 2014
    Date of Patent: June 30, 2015
    Assignee: ASAHI GLASS COMPANY, LIMITED
    Inventors: Tomoko Yajima, Kyoko Yamamoto
  • Patent number: 8664424
    Abstract: 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: Grant
    Filed: June 7, 2011
    Date of Patent: March 4, 2014
    Assignees: Lianhe Chemical Technology Co., Ltd, Jiangsu Lianhe Chemical Technology Co., Ltd.
    Inventors: Ping Wang, Xiaobin Fan, Xingjun Lin, Zhaohui He
  • Publication number: 20100234651
    Abstract: 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: Application
    Filed: March 16, 2010
    Publication date: September 16, 2010
    Applicant: Bayer CropScience AG
    Inventor: Thomas HIMMLER
  • Patent number: 7304192
    Abstract: 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: Grant
    Filed: July 2, 2003
    Date of Patent: December 4, 2007
    Assignee: Kaneka Corporation
    Inventors: Takeshi Kawamura, Chiho Yoshimi, Hidetoshi Odaka
  • Patent number: 7060862
    Abstract: 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: Grant
    Filed: December 30, 2003
    Date of Patent: June 13, 2006
    Assignee: Chung-Shan Institute of Science & Technology
    Inventors: Shean-Jeng Jong, Chun-Hsu Lin, Chao-chou Tu, Chung-Chien Chang
  • Patent number: 7026522
    Abstract: Disclosed is a process for the production of 2-amino-2-[2-(4-C2-20-alkyl-phenyl)ethyl]propane-1,3-diols.
    Type: Grant
    Filed: June 18, 2003
    Date of Patent: April 11, 2006
    Assignee: Novartis AG
    Inventors: Stephan Abel, Tetsuro Fujita, Ryoji Hirose, Guido Jordine, Tadashi Mishina
  • Patent number: 6992231
    Abstract: 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: Grant
    Filed: December 30, 2003
    Date of Patent: January 31, 2006
    Assignee: Chung-Shan Institute of Science & Technology
    Inventors: Shean-Jeng Jong, Chun-Hsu Lin, Ming-Te Shih, Chung-Chien Chang
  • Patent number: 6861566
    Abstract: 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: Grant
    Filed: March 11, 2002
    Date of Patent: March 1, 2005
    Assignees: Sumitomo Chemical Company, Limited, Ono Pharmaceutical Co., Ltd.
    Inventors: Hiroaki Hibino, Susumu Ohtsuka, Yasunobu Miyamoto, Itsuo Okumoto
  • Patent number: 6265628
    Abstract: 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: Grant
    Filed: April 9, 1999
    Date of Patent: July 24, 2001
    Assignee: Elf Atochem, S.A.
    Inventors: Raymond Commandeur, RĂ©gis Loze
  • Patent number: 5710355
    Abstract: 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: Grant
    Filed: June 10, 1996
    Date of Patent: January 20, 1998
    Assignee: Occidental Chemical Corporation
    Inventor: Ramesh Krishnamurti
  • Patent number: 5136114
    Abstract: 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: Grant
    Filed: April 30, 1990
    Date of Patent: August 4, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventor: Dieter Arlt
  • Patent number: 5099083
    Abstract: 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: Grant
    Filed: February 14, 1991
    Date of Patent: March 24, 1992
    Assignee: The Dow Chemical Company
    Inventors: P. J. Thomas, R. Garth Pews
  • Patent number: 5030777
    Abstract: 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: Grant
    Filed: October 31, 1989
    Date of Patent: July 9, 1991
    Assignee: Standard Chlorine of Delaware, Inc.
    Inventors: Jacob George, Kanti B. Desai, Jimmy Peress
  • Patent number: 5003116
    Abstract: 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: Grant
    Filed: October 10, 1989
    Date of Patent: March 26, 1991
    Assignee: Ethyl Corporation
    Inventor: Barbara C. Stahly
  • Patent number: 4990704
    Abstract: 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: Grant
    Filed: October 10, 1989
    Date of Patent: February 5, 1991
    Assignee: Ethyl Corporation
    Inventor: Barbara C. Stahly
  • Patent number: 4967026
    Abstract: 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: Grant
    Filed: May 11, 1989
    Date of Patent: October 30, 1990
    Assignee: Bromine Compounds Ltd.
    Inventor: Stephen Daren
  • Patent number: 4876404
    Abstract: 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: Grant
    Filed: August 11, 1987
    Date of Patent: October 24, 1989
    Assignee: Central Glass Company, Limited
    Inventors: Takeshi Kondo, Toshikazu Kawai, Hideki Oshio
  • Patent number: 4604243
    Abstract: 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: Grant
    Filed: July 25, 1985
    Date of Patent: August 5, 1986
    Assignee: Ethyl Corporation
    Inventor: Robert I. Davidson
  • Patent number: 4575565
    Abstract: The invention herein pertains to a novel process for making substituted benzotrifluorides.
    Type: Grant
    Filed: April 15, 1985
    Date of Patent: March 11, 1986
    Assignee: Monsanto Company
    Inventor: William F. Goure
  • Patent number: 4563529
    Abstract: 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: Grant
    Filed: June 4, 1981
    Date of Patent: January 7, 1986
    Assignee: Ishihara Sangyo Kaisha Ltd.
    Inventors: Ryuzo Nishiyama, Kanichi Fujikawa, Isao Yokomichi, Yasuhiro Tsujii, Shigeyuki Nishimura
  • Patent number: 4562280
    Abstract: 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: Grant
    Filed: October 18, 1984
    Date of Patent: December 31, 1985
    Assignee: The Dow Chemical Company
    Inventors: Jo Ann Gilpin, Lowell B. Lindy
  • Patent number: 4490532
    Abstract: 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: Grant
    Filed: July 28, 1980
    Date of Patent: December 25, 1984
    Assignee: Uniroyal Ltd.
    Inventor: John W. Harris
  • Patent number: 4419514
    Abstract: 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: Grant
    Filed: May 18, 1981
    Date of Patent: December 6, 1983
    Assignee: The Dow Chemical Company
    Inventors: Lennon H. McKendry, Michael J. Ricks, Richard B. Rogers