Preparing Acyclic Haloalkyl Group Containing Compound Patents (Class 570/191)
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Publication number: 20140235905Abstract: A method for the synthesis of 1,3-di(chloropropyl)-5-tert-butyl benzene includes the steps of conducting Friedl-Crafts alkylation of 1,3-diisopropyl benzene by tert-butyl chloride in the presence of an alkylation catalyst to obtain 1-tert-butyl-3,5-diisopropylbenzene; peroxidizing the 1-tert-butyl-3,5-diisopropyl benzene by gaseous oxygen in the presence of a peroxidation catalyst in a basic solution to obtain 1,3-di(peroxypropyl)-5-tert-butylbenzene; reducing the 1,3-di(peroxypropyl)-5-tert-butylbenzene with a reducing agent to 1,3-di(hydroxyl propyl)-5-tert-butylbenzene; and chlorinating the 1,3-di(hydroxypropyl)-5-tert-butylbenzene to obtain 1,3-di(chloropropyl)-5-tert-butyl benzene.Type: ApplicationFiled: July 2, 2012Publication date: August 21, 2014Applicant: The University of AkronInventors: Joseph P. Kennedy, Gabor Erdodi
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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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Patent number: 8030529Abstract: The present invention provides a process for the production of intermediate compounds of formula (I), wherein the substituents are as defined herein. The process comprises reacting a substituted aniline with aqueous HX, followed by removal of water by azeotropic distillation and diazotization and pyrolysis with an organic nitrite at elevated temperatures in the absence of a copper catalyst. Alternatively, gaseous HX can be used to substitute aqueous HX in the process. Consequently, a step of water removal by azeotropic distillation can be eliminated. The intermediate compounds of formula I are suitable as intermediates in the preparation of herbicidally active 3-hydroxy-4-aryl-5-oxopyrazoline derivatives.Type: GrantFiled: February 7, 2006Date of Patent: October 4, 2011Assignee: Syngenta Crop Protection, Inc.Inventors: Linhua Wang, Kristine Anderson Dolbeare, Frankie Lee Odom
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Patent number: 7875753Abstract: 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: GrantFiled: March 16, 2010Date of Patent: January 25, 2011Assignee: Bayer CropScience AGInventor: Thomas Himmler
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Publication number: 20090023964Abstract: The present invention provides a process for the production of intermediate compounds of formula (I), wherein the substituents are as defined herein. The process comprises reacting a substituted aniline with aqueous HX, followed by removal of water by azeotropic distillation and diazotization and pyrolysis with an organic nitrite at elevated temperatures in the absence of a copper catalyst. Alternatively, gaseous HX can be used to substitute aqueous HX in the process. Consequently, a step of water removal by azeotropic distillation can be eliminated. The intermediate compounds of formula I are suitable as intermediates in the preparation of herbicidally active 3-hydroxy-4-aryl-5-oxopyrazoline derivatives.Type: ApplicationFiled: February 7, 2006Publication date: January 22, 2009Applicants: SYNGENTA CROP PROTECTION, INC., SYNGENTA LIMITEDInventors: Linhua Wang, Kristine Anderson Dolbeare, Frankie Lee Odom
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Patent number: 7378449Abstract: An additive mixture useful as a flame retardant is described. The mixture is comprised of (i) a poly(bromophenyl)alkane having in the molecule in the range of 13 to 60 carbon atoms and in the range of two to four aryl groups and (ii) a poly(bromophenyl)bromoalkane having in the molecule in the range of 13 to 60 carbon atoms and in the range of two to four aryl groups, said poly(bromophenyl)bromoalkane being in an amount which is greater than 25 wt %, based on the total weight of the additive mixture. A facile process for making the poly(bromophenyl)bromoalkane is also described.Type: GrantFiled: October 23, 2006Date of Patent: May 27, 2008Assignee: Albemarle CorporationInventors: Raymond B. Dawson, Saadat Hussain
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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: 7271302Abstract: The present invention relates to processes for the bromination of organic compounds, and to bromination microreactors for carrying out these processes.Type: GrantFiled: September 19, 2000Date of Patent: September 18, 2007Assignee: Merck Patent GesellschaftInventors: Kai Fabian, Joeran Stoldt, Hanns Wurziger, Norbert Schwesinger
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Patent number: 7129385Abstract: An additive mixture useful as a flame retardant is described. The mixture is comprised of (i) a poly(bromophenyl)alkane having in the molecule in the range of 13 to 60 carbon atoms and in the range of two to four aryl groups and (ii) a poly(bromophenyl)bromoalkane having in the molecule in the range of 13 to 60 carbon atoms and in the range of two to four aryl groups, said poly(bromophenyl)bromoalkane being in an amount which is greater than 25 wt %, based on the total weight of the additive mixture. A facile process for making the poly(bromophenyl)bromoalkane is also described.Type: GrantFiled: April 20, 2004Date of Patent: October 31, 2006Assignee: Albemarle CorporationInventors: Raymond B. Dawson, Saadat Hussain
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Patent number: 7109387Abstract: ?-Chloroisopropyl-substituted aromatics are obtained in high yield by treating isopropenyl-substituted aromatics with hydrogen chloride gas in the absence of a solvent. The ?-chloroisopropyl-substituted aromatics serve as initiators for the cationic polymerization of isobutene.Type: GrantFiled: February 24, 2003Date of Patent: September 19, 2006Assignee: BASF AktiengesellschaftInventors: Gabriele Lang, Stephan Hueffer, Arno Lange, Hans Peter Rath
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Patent number: 7094934Abstract: In a process for producing a hydrogen-containing fluorinated hydrocarbon in which a halogenated hydrocarbon reaction raw material, which includes a chlorinated alkene and/or a hydrogen-containing chlorinated alkane, is subjected to a fluorination reaction with hydrogen fluoride in a liquid phase in a reactor in the presence of a fluorination catalyst to obtain a reaction mixture which includes the hydrogen-containing fluorinated hydrocarbon, the reactor to be used has a portion which is able to contact with the reaction mixture, at least a part of this portion being made of an alloy material of 18 to 20% by weight of chromium, 18 to 20% by weight of molybdenum, 1.5 to 2.2% by weight of at least one element selected from niobium and tantalum and the balance of nickel.Type: GrantFiled: January 31, 2001Date of Patent: August 22, 2006Assignee: Daikin Industries, Ltd.Inventors: Noriaki Shibata, Tatsuo Nakada, Takashi Shibanuma
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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: 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: 6774270Abstract: A method of removing hexafluoropropylene dimers (“HFP dimers”), dimer hydrides and other oligomers from a fluid is described. The method comprises heating the fluid to isomerize the HFP dimers to the thermodynamic isomer, and contacting the fluid with a tertiary amine (or salts thereof) to form a hexafluoropropylene dimer—tertiary amine adduct. The method may further comprise the step of separating the dimer adducts from the reaction mixture.Type: GrantFiled: April 1, 2003Date of Patent: August 10, 2004Assignee: 3M Innovative Properties CompanyInventors: Zhongxing Zhang, Zai-Ming Qiu, Daniel R. Vitcak, Richard M. Flynn
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Patent number: 6756513Abstract: Monochlorinated hydrocarbons of high isomeric purity are prepared by a process, which comprises: reacting a monoalcohol having an alkyl radical having from 3 to 20 carbon atoms with cyanuric chloride; and purifying the resulting monochlorinated hydrocarbon by distillation after separation of salts and washing the monochlorinated hydrocarbon with alkali. The invention relates to a process for preparing monochlorinated hydrocarbons which contain an alkyl radical having from 3 to 20 carbon atoms and have a high isomeric purity by reacting a monoalcohol having a hydrocarbon radical containing an alkyl radical having from 3 to 20 carbon atoms to which additional cycloaliphatic radicals, aryl radicals, aralkyl radicals and alkylaryl radicals may be bound with cyanuric chloride, separating off salts, washing the reaction mixture with alkali and purifying the resulting monochlorinated hydrocarbons by distillation.Type: GrantFiled: August 16, 2002Date of Patent: June 29, 2004Assignee: Degussa AGInventors: Manfred Neumann, Clemens Osterholt
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Patent number: 6407298Abstract: A process for the preparation of an alcohol compound (1), characterized by subjecting p-iodochlorobenzene to Pd coupling with allyl alcohol in the presence of tetramethylammonium chloride, followed by reduction, and a process for the preparation of a compound (2), characterized by brominating the alcohol compound (1) obtainable by said process:Type: GrantFiled: May 4, 2001Date of Patent: June 18, 2002Assignee: Nissan Chemical Industries, Ltd.Inventors: Hiroo Matsumoto, Minako Kamikawaji, Takashi Horiuchi
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Patent number: 6300532Abstract: A process for catalytic addition of haloalkanes to alkenes involving the step of reacting the haloalkane with the alkene in the presence of a catalyst. The catalyst is an organophosphite compound represented by the following formula: P(ORa)(ORb)(ORc), where Ra, Rb, and Rc are each an alkyl group or an aralkyl group.Type: GrantFiled: December 15, 1998Date of Patent: October 9, 2001Assignee: AlliedSignal Inc.Inventors: Michael Van Der Puy, Timothy Rech Demmin
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Patent number: 6255545Abstract: The present invention is concerned with a novel process for the preparation of 3,5-bis(trifluoromethyl)bromobenzene (CAS 328-70-1). This compound is useful as an intermediate in the synthesis of compounds which possess pharmacological activity.Type: GrantFiled: June 8, 2000Date of Patent: July 3, 2001Assignee: Merck & Co., Inc.Inventors: Raymond Cvetovich, Fuh-Rong Tsay
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Patent number: 6013841Abstract: The 3- and 4-methylcatechols are converted to the corresponding benzaldehyde by first alkylating the hydroxyl groups to form an alkylated methylcatechol. The methyl group is then converted to a methyl dibromide group using 1,3-dibromo-5,5-dimethylhydantoin in the presence of a non-polar, non-reactive solvent such as carbon tetrachloride and heptane and a radical initiator having a ten hour half-life temperature in the range of 47.degree. to 55.degree. C. The dibromide is then hydrolyzed to form the aldehyde.Type: GrantFiled: July 30, 1998Date of Patent: January 11, 2000Assignee: Dakota Gasification CompanyInventor: Paul D. Pansegrau
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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: 5672791Abstract: Nuclear-halogenated benzotrichlorides are prepared in a particularly advantageous manner from the corresponding nuclear-halogenated benzotrifluorides by reacting nuclear-halogenated benzotrifluorides with silicon tetrachloride in the presence of catalytic amounts of aluminium trichloride.Type: GrantFiled: January 24, 1996Date of Patent: September 30, 1997Assignee: Bayer AktiengesellschaftInventors: Fritz Doring, Reinhold Gehring, Josef Heinrich
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Patent number: 5583272Abstract: Described are methyl, substituted propyl-substituted pentamethyl indane derivatives defined according to the structure: ##STR1## wherein R.sub.1 represents hydroxyl or methyl; and R.sub.2 represents hydrogen, chloro or OR.sub.6 ; and R.sub.3 represents hydrogen or methyl with the provisos:(i) when R.sub.1 is hydroxyl, R.sub.2 is hydrogen and R.sub.3 is methyl; and(ii) when R.sub.1 is methyl, one of R.sub.2 is chloro or OR.sub.6 and R.sub.3 is hydrogenand wherein the structure represents a mixture wherein in the mixture in one of the compounds R.sub.4 and R.sub.4 ' are both methyl and R.sub.7 is methyl (about 90% by weight); and in the other compounds one of R.sub.4 or R.sub.4 ' is methyl and the other is ethyl and R.sub.7 is hydrogen (about 10% by weight of the compounds); and wherein R.sub.Type: GrantFiled: April 25, 1995Date of Patent: December 10, 1996Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Olivier J. Gillotin
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Patent number: 5502261Abstract: The present invention relates to a process for preparing 2,2'-bis(halomethyl)-1,1'-binaphthyl, by reacting 2,2'-dimethyl-1,1'-binaphthyl in the presence of a solvent with a halogenating agent under the action of light having a wavelength of from 10.sup.-5 to 10.sup.-8 m in the presence or absence of a free-radical former at from -10.degree. to 120.degree. C.Type: GrantFiled: March 21, 1995Date of Patent: March 26, 1996Assignee: Hoechst AktiengesellschaftInventors: Hans-Jerg Kleiner, Dieter Regnat, Horst Ro/ schert
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Patent number: 5475170Abstract: An improvement in a process for the haloalkylation of a first aromatic compound having at least one free ring position with a haloalkylating reagent and in the presence of a haloalkylation catalyst, said process producing a haloalkylated first aromatic compound and a dimeric reaction by-product of said first aromatic compound having at least one free ring position, the improvement comprising treating said by-product with a second aromatic compound having at least one free ring position the same or different than said first aromatic compound in the presence of a catalytically effective amount of an acid for a time and at a temperature sufficient to cleave said diarylalkane by-product and produce thereby said first aromatic compound having at least one free ring position.Type: GrantFiled: June 27, 1994Date of Patent: December 12, 1995Assignee: Albermarle CorporationInventor: Tse-Chong Wu
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Patent number: 5426255Abstract: Described are processes for preparing methyl, substituted propyl-substituted pentamethyl indane derivatives using as a starting material the mixture of compounds defined according to the structure: ##STR1## also known as GALAXOLIDE.RTM. (trademark of International Flavors & Fragrances Inc.). Also described are mixtures of methyl, substituted propyl-substituted pentamethyl indane derivatives with other musk chemicals including but not limited to GALAXOLIDE.RTM.Type: GrantFiled: July 22, 1994Date of Patent: June 20, 1995Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Olivier J. Gillotin
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Patent number: 5420369Abstract: The co-formation of diarylalkane by-product in the chloroalkylation of an aromatic compound with an aldehyde is minimized by conducting the reaction in a continuous manner in a concentration with agitation and in the presence of both hydrogen sulfate and hydrogen chloride.Type: GrantFiled: July 18, 1994Date of Patent: May 30, 1995Assignee: Albemarle CorporationInventors: R. Carl Herndon, Jr., Gary D. Focht, Karl R. Jones
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Patent number: 5162577Abstract: A novel process for the lithiation of 1,3-bis(trifluoro-methyl)benzene in a solvent is described, said process comprising carrying out the lithiation with the lithium salt of an amine of the general formulaR.sup.1 R.sup.2 NH Iwherein R.sup.1 and R.sup.2 are secondary or tertiary lower alkyl or secondary or tertiary lower alkyl substituted by a lower alkyl or lower cycloalkyl or lower cycloaklyl substituted by a lower alkyl, or R.sup.1 and R.sup.2 taken together form a C.sub.6-14 -alkylene group in which the two carbon atoms linked with the nitrogen atom are secondary or tertiary and are separated from each other by 2 to 4 carbon atoms.The solution of the lithiated 1,3-bis(trifluoromethyl)-benzene obtained can be reacted with an electrophile which is suitable for the substitution of lethiated benzene derivatives, whereby a compound of the formula ##STR1## wherein R.sup.3 signifies the residue of an electrophile which is suitable for the substitution of lithiated benzene derivatives, is obtained.Type: GrantFiled: February 1, 1991Date of Patent: November 10, 1992Assignee: Hoffmann-La Roche Inc.Inventor: Raffaello Masciadri
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Patent number: 5157173Abstract: 4-chlorobenzotrichloride was prepared by the chlorination of p-xylene in the vapor phase at a temperature above about 200.degree. C. in the presence of an activated carbon catalyst and water. An approximately 75 percent calculated yield was obtained at 250.degree. C. using a wide-pore activated carbon catalyst.Type: GrantFiled: September 24, 1991Date of Patent: October 20, 1992Assignee: DowElancoInventors: Michael A. DesJardin, Clark P. Allphin
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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: 5113020Abstract: The present invention provides a process for producing a p-halogenobenzophenone derivative of a high purity in a high yield at a low cost in the presence of a repeatedly usable catalyst having a long life and free from the problem of waste water treatment without using any chemical of a strong toxicity. According to the present invention, the p-halogenobenzophenone derivative is produced by reacting an (un)substituted benzotrichloride of the following formula (I) with a halogenobezene of the following formula (II) in the presence of a catalyst selected from the group consisting of alumina, nickel sulfate, zirconium oxide, amorphous silica/alumina and a mixture of two or more of them or a catalyst obtained by treating these compounds with an acid and hydrolyzing the resulting bisphenyldichloromethane of the following formula (III): ##STR1## wherein X represents a halogen atom or a hydrogen atom and Y represents a halogen atom.Type: GrantFiled: August 28, 1991Date of Patent: May 12, 1992Assignee: Kureha Kagaku Kogyo K.K.Inventors: Kazuhiko Sunagawa, Nobuyuki Kusano
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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: 4956055Abstract: A process is disclosed for preparing bidentate ligands of the formula: ##STR1## wherein: each Ar is independently selected from aromatic ring compounds having 6 up to 14 carbon atoms, e.g., phenyl, naphthyl, phenanthryl and anthracenyl;the x bonds and the y bonds are attached to adjacent carbon atoms on the ring structures;each R, when present as a substituent, is independently selected from alkyl, alkoxy, aryloxy, aryl, aralyky, alkaryl, alkoxyalky, cycloaliphatic, halogen, alkanoyl, alkanoyloxy, alkoxycarbonyl, carboxyl, cyano or formyl radicals;n is a whole number in the range of 0-4 where Ar is phenyl; 0-6 where Ar is naphthyl; and 0-8 where Ar is phenanthryl or anthracenyl;each R.sub.1 and R.sub.2 is independently selected from alkyl, aryl, aralkyl, alkaryl or cycloaliphatic radicals, or substituted derivatieves thereof;each R.sub.3 and R.sub.4 is independently selected from hydrogen and the R.sub.Type: GrantFiled: July 24, 1989Date of Patent: September 11, 1990Assignee: Eastman Kodak CompanyInventor: Thomas A. Puckette
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Patent number: 4954227Abstract: A process is disclosed for preparing bidentate ligands of the formula: ##STR1## wherein: each AR is independently selected from aromatic ring compounds having 6 up to 14 carbon atoms, e.g., phenyl, naphthyl, phenanthryl and anthracenyl;the x bonds and the y bonds are attached to adjacent carbon atoms on the ring structures;each R, when present as a substituent, is independently selected from alkyl, alkoxy, aryloxy, aryl, aralkyl, alkaryl, alkoxyalkyl, cycloaliphatic, halogen, alkanoyl, alkanoyloxy, alkoxycarbonyl, carboxyl, cyano or formyl radicals;n is a whole number in the range of 0-4 were Ar is phenyl; 0-6 where Ar is naphthyl; and 0-8 where Ar is phenanthryl or anthracenyl;each R.sub.1 and R.sub.2 is independently selected from alkyl, aryl, aralkyl, alkaryl or cycloaliphatic radicals, or substituted derivatives thereof;each R.sub.3 and R.sub.4 is independently selected from hydrogen and the R.sub.Type: GrantFiled: July 24, 1989Date of Patent: September 4, 1990Assignee: Eastman Kodak CompanyInventor: Thomas A. Puckette
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Patent number: 4879008Abstract: A process is disclosed for preparing bidentate ligands of the formula: ##STR1## wherein: each Ar is independently selected from aromatic ring compounds having 6 up to 14 carbon atoms, e.g., phenyl, naphthyl, phenanthryl and anthracenyl;the x bonds and y bonds are attached to adjacent carbon atoms on the ring structure;each R, when present as a substituent, is independently selected from alkyl, alkoxy, aryloxy, aryl, aralkyl, alkaryl, alkoxyalkyl, cycloaliphatic, halogen, alkanoyl, alkanoyloxy, alkoxycarbonyl, carboxyl, cyano or formyl radicals;n is a whole number in the range of 0-4 were Ar is phenyl; 0-6 where Ar is naphthyl; and 0-8 where Ar is phenanthryl or anthracenyl;each R.sub.1 and R.sub.2 is independently selected from alkyl, aryl, aralkyl, alkaryl or cycloaliphatic radicals, or substituted derivatives thereof;each R.sub.3 and R.sub.4 is independently selected from hydrogen and the R.sub.Type: GrantFiled: November 9, 1987Date of Patent: November 7, 1989Assignee: Eastman Kodak CompanyInventor: Thomas A. Puckette
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Patent number: 4879416Abstract: The process for preparing a bidentate ligand comprising the steps,(1) contacting with ozone under ozonolysis conditions a suspension in a hydroxylic reaction medium of phenanthrene or a phenanthrene derivative to form an ozonated intermediate,(2) contacting said ozonated intermediate with a reducing agent under conditions appropriate to form the corresponding diol,(3) contacting said diol with a latent displaceable functional group under conditions appropriate to convert the diol to the corresponding difunctional biaryl compound, and(4) contacting said difunctional biaryl compound, with an anion of N, P, As, Sb or Bi under conditions appropriate to form the desired bidentate ligand.Type: GrantFiled: November 23, 1987Date of Patent: November 7, 1989Assignee: Eastman Kodak CompanyInventors: Thomas A. Puckette, Thomas J. Devon, Gerald W. Phillips, Jerome L. Stavinoha
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Patent number: 4855517Abstract: Aromatic bromine compounds are prepared by reacting aromatic nitro compounds with elemental bromine in the gas phase at temperatures between about 310.degree. to 550.degree. C. In this reaction, the nitro groups are selectively replaced by bromine; further bromination of the aromatic system beyond that does not take place.Type: GrantFiled: September 21, 1987Date of Patent: August 8, 1989Assignee: Hoechst AktiengesellschaftInventors: Hans J. Metz, Klaus Warning
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Patent number: 4769503Abstract: A process for the preparation of 3,4-dichlorobenzotrihalides of the formula I ##STR1## where X is fluorine or chlorine, by reacting the corresponding 4-monochlorobenzotrihalides with chlorine gas in the presence of a catalytic amount of a Lewis acid, wherein the reaction mixture is recycled by means of a pump in a circulatory apparatus with static mixers and the amount of chlorine equivalent to the conversion of the corresponding 4-monochlorobenzotrihalide is introduced at 20.degree.-120.degree. C.Type: GrantFiled: August 30, 1984Date of Patent: September 6, 1988Assignee: BASF AktiengesellschaftInventors: Adolf Parg, Gerd Husslein, Gerhard Hamprecht
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Patent number: 4767885Abstract: Sterically hindered binifers are made as well as utilized to produce telechelic polyisobutylenes. The telechelic polymers can be produced at high temperatures, for example minus 30.degree. C.Type: GrantFiled: August 6, 1984Date of Patent: August 30, 1988Assignee: University of AkronInventor: Joseph P. Kennedy
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Patent number: 4622431Abstract: Organic chloroformate compounds are decomposed to their corresponding chlorides by heating the chloroformate, e.g., between 100.degree. and 175.degree. C., in the presence of a catalytic amount of solid poly(vinylpyridine), e.g., poly(4-vinylpyridine), for a time sufficient to convert the chloroformate to the corresponding chloride.Type: GrantFiled: April 4, 1985Date of Patent: November 11, 1986Assignee: PPG Industries, Inc.Inventors: Robert G. Briody, Henry C. Stevens
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Patent number: 4607116Abstract: Provided is a process for preparing a diaryl or a mixture of diaryls represented by any or a combination of the following formulae (II), (III) and (V), characterized in that a diaryliodonium salt represented by the following formula (I) is reacted in a solvent in the presence of a transition metal catalyst and a reducing metal at a temperature in the range of room temperature to 100.degree. C.:[Ar.sub.1 -I.sup..sym. -Ar.sub.2 ]X.sup..crclbar. (I)Ar.sub.1 -Ar.sub.1 (II)Ar.sub.1 -Ar.sub.2 (III)Ar.sub.2 -Ar.sub.2 (IV)wherein Ar.sub.1 and Ar.sub.2, which may be alike or different, are each an aryl group which may have a substituent group or groups and X.sup..crclbar. is a counter ion which is inert to said reaction.Type: GrantFiled: March 8, 1984Date of Patent: August 19, 1986Assignee: Nippon Petrochemicals Company LimitedInventors: Yasuo Yamazaki, Takehiko Suzuki, Masaharu Uchiyama
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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: 4560814Abstract: Disclosed is a process for alkylating halogenated and trifluoromethylated benzene compounds. In that process, an alkyl halide is reacted with a benzene compound having two or three substituents selected from the group consisting of the halogens and the trifluoromethyl group, and also having a hydrogen atom whose two ortho positions are occupied by two of the said substituents. The reaction is carried out in the presence of at least one alkali metal amide and at least one agent that complexes with the cation of the alkali metal amide.Type: GrantFiled: January 31, 1984Date of Patent: December 24, 1985Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Gerard Soula
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Patent number: 4558166Abstract: Process for the preparation of benzal chlorides from benzotrichlorides, according to which benzotrichlorides are reacted with thiols in the presence of metal salts at elevated temperatures.Type: GrantFiled: March 21, 1984Date of Patent: December 10, 1985Assignee: Bayer AktiengesellschaftInventors: Bernd Baasner, Erich Klauke
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Patent number: 4473709Abstract: A novel N,N,N-trimethyl-[1,1'-biphenyl]-2-methanaminium compound is subjected to a rearrangement reaction to give a 3-dimethylaminomethyl-2-methyl-[1,1'-biphenyl] compound which is then converted to the corresponding 3-halomethyl-2-methyl-[1,1'-biphenyl] compound. The halomethyl compound is an intermediate for pyrethroid and related insecticides having the alcohol moiety derived from a 2-methyl-[1,1'-biphenyl]-3-methanol.Type: GrantFiled: July 14, 1980Date of Patent: September 25, 1984Assignee: FMC CorporationInventors: Ronald E. Montgomery, Ernest L. Plummer, Anthony J. Martinez
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Patent number: 4447650Abstract: Methylene coupled aromatic compounds are prepared by contacting an aromatic reactant having a reactive hydrogen with chloromethyl methyl carbonate at a temperature from about 25.degree. C. to about 250.degree. C. in the presence of a catalytic amount of a Lewis acid.Type: GrantFiled: July 26, 1982Date of Patent: May 8, 1984Assignee: The Dow Chemical CompanyInventor: James M. Renga
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Patent number: 4414406Abstract: Molybdenum compounds, particularly molybdenum sulfide, molybdenum silicide, molybdenum selenide and molybdenum telluride are useful Friedel-Crafts catalysts for the aralkylation of aromatics to produce polybenzyls, the manufacture of aromatic ketones, aromatic sulfones and aromatic esters.The foregoing processes are carried out at a temperature of about 60.degree. to 250.degree. C. and at a catalyst concentration of about 0.1 to 15% by weight of reactants. The reaction products are useful as laminates, herbicides and bactericides.Type: GrantFiled: September 18, 1981Date of Patent: November 8, 1983Assignee: Standard Oil Company (Indiana)Inventor: Ellis K. Fields
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Patent number: 4362884Abstract: Organosilicon compounds referred to as silacrown ethers or "silacrowns" are of the general formula: ##STR1## where R.sup.1 and R.sup.2 are organic radicals or hydrogen and n is an integer between 4 and 10 inclusive. Silacrown ethers are prepared by reacting polyethylene glycol with substituted silanes under conditions promoting cyclization over polymerization. Silacrown ethers may be employed as phase-transfer catalysts in solution or immobilized on siliceous supports.Type: GrantFiled: November 23, 1981Date of Patent: December 7, 1982Assignee: Petrarch Systems, Inc.Inventor: Barry C. Arkles
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Patent number: 4334103Abstract: The invention relates to a process for nucleophilic substitution reactions. According to the invention the reaction is carried out in a hetergeneous system, consisting of a solid and a dissolved reactant, one or several organic solvents, one or several linear polyether derivatives, and/or amino compounds and water. The volume of the water is preferably at the most 100% of the volume of the organic solvent and more preferably 5%.Type: GrantFiled: June 27, 1980Date of Patent: June 8, 1982Assignee: Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Rt.Inventors: Laszlo Toke, Gabor T. Szabo, Gabor Szabo, Lajos Nagy, Istvan Rusznak