Having Acyclic Carbon To Carbon Unsaturation Patents (Class 570/193)
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Patent number: 8829255Abstract: Provided are (Z,Z,E)-1-chloro-6,10,12-pentadecatriene that can be synthesized without an oxidation reaction and a method for preparing (Z,Z,E)-7,11,13-hexadecatrienal by using (Z,Z,E)-1-chloro-6,10,12-pentadecatriene while not using an oxidation reaction. More specifically, provided is a method for preparing (Z,Z,E)-7,11,13-hexadecatrienal including a step of reacting a Grignard reagent into which (Z,Z,E)-1-chloro-6,10,12-pentadecatriene is converted with ethyl orthoformate to obtain (Z,Z,E)-1,1-diethoxy-7,11,13-hexadecatriene, and a step of treating the (Z,Z,E)-1,1-diethoxy-7,11,13-hexadecatriene with an acid to obtain (Z,Z,E)-7,11,13-hexadecatrienal.Type: GrantFiled: February 25, 2014Date of Patent: September 9, 2014Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Yuki Miyake, Miyoshi Yamashita, Takehiko Fukumoto, Naoki Ishibashi
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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: 20120142935Abstract: This invention provides a method for preparing a 1,2,3-triazole compound comprising contacting an organic azide with a 2-substituted-1-haloalkyne, in the presence of a copper catalyst and a copper-coordinating ligand (preferably a tertiary amine) in a liquid reaction medium, thereby forming a 1,4,5-substituted-1,2,3-triazole compound including a halo substituent at the 5-position of the triazole, the organic portion of the organic azide at the 1-position of the triazole, and the substituent of the 1-iodoalkyne at the 4-position of the triazole. A method for preparing 1-iodoalkynes is also provided.Type: ApplicationFiled: August 11, 2010Publication date: June 7, 2012Inventors: Jason E. Hein, Jonathan C. Tripp, Larissa Krasnova, K.Barry Sharpless, Valery V. Fokin
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Patent number: 7074434Abstract: Process for the separation of a mixture comprising at least one hydrofluoroalkane and hydrogen fluoride, according to which a hydrofluoroalkane/hydrogen fluoride mixture is reacted with at least one chlorinated or chlorofluorinated precursor of the hydrofluoroalkane. Process for the preparation of a hydrofluoroalkane comprising such a separation, in combination with a catalytic reaction stage. Azeotropic compositions.Type: GrantFiled: October 29, 2002Date of Patent: July 11, 2006Assignee: Solvay (Societe Anonyme)Inventors: Alain Lambert, Vincent Wilmet
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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: 5981818Abstract: A novel process is provided which integrates the cracking of hydrocarbon containing feedstocks with the olefins purification and olefins derivative process utilizing dilute olefin feedstocks.Type: GrantFiled: October 18, 1996Date of Patent: November 9, 1999Assignee: Stone & Webster Engineering Corp.Inventors: David Purvis, Richard H. Mc Cue
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Patent number: 5977419Abstract: The invention relates to novel processes for the preparation of phenyl acetic acid derivatives of the formula (I) some of which are known ##STR1## in which R.sup.1, R.sup.2 and R.sup.3 independently of each other each represent hydrogen, alkyl or alkoxy by ozonolysis of compounds of the formula (II) ##STR2## in which R.sup.4 represents hydrogen or methyl and oxidation of the reaction products obtained therefrom. The invention further relates to novel intermediates and a process for the preparation thereof.Type: GrantFiled: December 22, 1997Date of Patent: November 2, 1999Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Rainer Fuchs
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Patent number: 5917098Abstract: 1,1,1,3,3-Pentachlorobutane, whose fluorination leads to 1,1,1,3,3-pentafluorobutane, is prepared with high yield and selectivity by addition of carbon tetrachloride to 2-chloropropene in the presence of a copper salt and an amine.Type: GrantFiled: January 27, 1997Date of Patent: June 29, 1999Assignee: Elf Atochem S.A.Inventors: Rene Bertocchio, Andre Lantz, Laurent Wendlinger
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Patent number: 5268517Abstract: The preparation of Z-1,2-diarylallyl chlorides of the general formula I ##STR1## in which R.sup.1 and R.sup.2, independently of one another, are hydrogen, halogen, alkyl, haloalkyl, alkoxy, haloalkoxy or a substituted aromatic radical, and n and m are 1, 2 or 3, by dehydrating chlorohydrins of the formula II ##STR2## in which the radicals are as defined above, at up to 50.degree. C. in an inert ether or carboxylic acid ester as solvent and in the presence of a carboxylic anhydride and an organic or inorganic acid, the conversion thereof into azolylmethyloxiranes, and novel intermediates are described.Type: GrantFiled: December 7, 1992Date of Patent: December 7, 1993Assignee: BASF AktiengesellschaftInventors: Reiner Kober, Rainer Seele, Heinz Isak, Eckhard Hichmann, Norbert Goetz, Thomas Zierke
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Patent number: 5262575Abstract: This invention, in one respect, is a process for producing allylic chlorides which comprises contacting a feedstream containing an olefin in the gas phase with a chlorination composition under conditions effective to produce an allylic chlorine and wherein the mole ratio of oxygen to olefin is from 0 to about 1:20 in the feedstream. The chlorination composition contains supported palladium chloride, platinum chloride, or palladium chloride and a chloride of a Group 1 alkali metal selected from the group consisting of lithium, sodium, and potassium; a Group 2 alkaline earth metal; a Group 9 metal; nickel; and a Group 12 metal. The chlorination composition can be regenerated by contacting the chlorination composition with chlorine in a cyclic reaction scheme.Type: GrantFiled: August 4, 1992Date of Patent: November 16, 1993Assignee: The Dow Chemical CompanyInventor: William P. Dianis
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Patent number: 5243109Abstract: Tribromostyrene (TBS) is produced by the preparation of a TBS precursor, which is .beta.-bromoethyl-tribromobenzene (.beta.-BrBr.sub.3), and the successive elimination of hydrogen bromide from said precursor. The precursor is prepared by selective bromination of phenethyl bromide (.beta.-Br), wherein the molar ratio of bromine to phenethyl bromide is comprised between 2.5 and 3.5, and preferably between 3.1 and 3.3 included; and by adding bromine, after an initial addition, at a controlled molar rate.Type: GrantFiled: August 6, 1992Date of Patent: September 7, 1993Assignee: Bromine Compounds Ltd.Inventors: Nurit Kornberg, David Beneish, Michael Peled
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Patent number: 5100986Abstract: Halogenated styrene-based coatings having surprisingly good physical properties in combination with flame retardancy are prepared from copolymers of ring-halogenated, ethylenically unsaturated aromatic monomers and aliphatic conjugated dienes having from 4 to 10 carbon atoms, and from terpolymers of ring-halogenated, ethylenically unsaturated aromatic monomers, halogen-free aromatic monomers, and aliphatic conjugated dienes having from 4 to 10 carbon atoms.Type: GrantFiled: October 31, 1990Date of Patent: March 31, 1992Assignee: Great Lakes Chemical CorporationInventors: Nicolai A. Favstritsky, Jin-liang Wang, Richard S. Rose
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Patent number: 5066752Abstract: Halogenated styrene-based polymers having surprisingly good physical properties in combination with flame retardancy include copolymers of ring-halogenated, ethylenically unsaturated aromatic monomers and aliphatic conjugated dienes having from 4 to 10 carbon atoms, and terpolymers of ring-halogenated, ethylenically unsaturated aromatic monomers, halogen-free aromatic monomers, and aliphatic conjugated dienes having from 4 to 10 carbon atoms.Type: GrantFiled: June 20, 1990Date of Patent: November 19, 1991Assignee: Great Lakes Chemical CorporationInventors: Nicolai A. Favstritsky, Jin-Liang Nang
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Patent number: 4898998Abstract: A process for producing brominated acenaphthylene condensates of the formula: ##STR1## wherein x is 1 or 2, y is an integer from 1 to 6 and n is 1 or more, from elementary units of the following formulas: ##STR2## wherein y is as defined above, comprising, (A) brominating the side chain of the acenaphthene with 0.2 to 2.0 times as many moles of bromine as acenaphthene, said bromination initiated by ultraviolet radiation or by a radical initiator in a halogenated hydrocarbon solvent, (B) adding a Lewis acid catalyst to the reaction solution of step (A) to promote the condensation of the brominated acenaphthene product of step (A), (C) adding to the reaction solution of step (B) an equimolar or more amount of bromine relative to the amount of acenaphthene starting material, to further brominate and condense the brominated acenaphthene and/or brominated acenaphthene condensates; and (D) dehydrobrominating the brominated acenaphthene condensates.Type: GrantFiled: May 31, 1984Date of Patent: February 6, 1990Assignee: Toyo Soda Manufacturing Co., Ltd.Inventors: Masashige Kubo, Hideo Sakka, Yukihiro Tsutsumi
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Patent number: 4886922Abstract: A method for preparing an .alpha.-substituted styrene such as 2-(3,5-dichlorophenyl)-4,4,4-trichloro-1-butene comprising contacting, an .alpha.-haloalkylbenzene such as 3-(3,5-dichlorophenyl)-1,1,1,3-tetrachlorobutane with a catalyst consisting essentially of .gamma.-alumina dried to a moisture content between about zero to about 12% by weight, the .gamma.-alumina serving to catalyze the dehydrohalogenation of the .alpha.-haloalkylbenzene to produce the .alpha.-substituted styrene.Type: GrantFiled: September 14, 1984Date of Patent: December 12, 1989Assignee: The Dow Chemical CompanyInventors: Dennis K. Klipa, James R. Dewald
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Patent number: 4886891Abstract: The present invention provides a process for preparing a 1,1-disubstituted ethylene derivative of the formula ##STR1## which comprises reacting lead with a carbinol derivative of the formula ##STR2## wherein R.sup.1, R.sup.2, R.sup.3, X, Y, m and n are defined in the specification. The reaction is conducted more advantageously in the presence of a metal having higher ionization tendency than lead.Type: GrantFiled: December 18, 1987Date of Patent: December 12, 1989Assignee: Otsuka Kagaku Kabushiki KaishaInventors: Shigeru Torii, Masatoshi Taniguchi, Michio Sasaoka, Yoshihisa Tomotaki, Mitsuo Akada, Hideo Tanaka, Akira Suzuki, Shiro Yamashita
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Patent number: 4814522Abstract: Catalyzed halogen exchange between perhaloolefins to form products of the formulas:R.sup.1 R.sup.2 C=CR.sup.3 R.sup.8andR.sup.5 R.sup.6 C=CR.sup.7 R.sup.4wherein R.sup.1, R.sup.2, R.sup.3, R.sup.5, Rhu 6l , and R.sup.7 are individually selected from the group F, Cl, Br, C.sub.1 to C.sub.4 perfluoroalkyl, and pentafluorophenyl; or R.sup.1 and R.sup.3, R.sup.2 and R.sup.3, R.sup.5 and R.sup.7, R.sup.6 and R.sup.7 together, with the proviso that both groups are in the cis configuration, are selected from the group perfluoroalkylene of 2 to 4 carbons ando--C.sub.6 F.sub.4 (--)CF.sub.2 --,R.sup.8 =F, R.sup.4 =Cl or Br; and wherein none of the fluoroolefins simultaneously contains both Cl and Br.Type: GrantFiled: January 11, 1988Date of Patent: March 21, 1989Assignee: E. I. DuPont DeNemours and CompanyInventor: Frank J. Weigert
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Patent number: 4734534Abstract: Novel alumina-supported nickel boride catalysts prepared by the borohydride promoted reduction of nickel arsenate are described. Method of catalyst preparation and process for hydrogenation of acetylenic and diolefinic compounds employing the invention catalysts are also described.Type: GrantFiled: February 5, 1986Date of Patent: March 29, 1988Assignee: Phillips Petroleum CompanyInventor: Ted H. Cymbaluk
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Patent number: 4686311Abstract: A process for the preparation of bromostyrenes which comprises aqueous alcoholic alkali dehydrohalogenation of a 1-haloethyl bromobenzene, a 2-haloethyl bromobenzene, or a 1-methyl-2-haloethyl brominated benzene in the presence of a phase transfer catalyst at a temperature of between about 0.degree. C. and about 150.degree. C. The bromostyrenes have the particular utility as a comonomer for the preparation of a co-polymer exhibiting a flame retardancy. Both bromostyrenes and brominated alpha-methyl styrenes are formed.Type: GrantFiled: September 27, 1983Date of Patent: August 11, 1987Assignee: Ethyl CorporationInventor: Philip F. Jackisch
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Patent number: 4668832Abstract: Halogenated, unsaturated alcohols are dehydrated by contacting the alcohol and a carrier gas with a silica alumina catalyst to form dienes of the formula: ##STR1## wherein each X is independently hydrogen, fluorine chlorine, or bromine with the proviso that no more than one of them is hydrogen, and each R is independently hydrogen, alkyl, aralkyl, alkaryl, or aryl.Type: GrantFiled: October 8, 1985Date of Patent: May 26, 1987Assignee: The Dow Chemical CompanyInventor: William J. Kruper, Jr.
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Patent number: 4650910Abstract: Substituted styrenes are prepared by treatment on N-acyl-B-phenethylamines with bases and removal by distillation of the styrene which is formed during the reaction.Type: GrantFiled: March 4, 1986Date of Patent: March 17, 1987Assignee: Bayer AktiengesellschaftInventors: Karl-Wilhelm Henneke, Karlfried Wedemeyer
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Patent number: 4633026Abstract: A process for preparing ring-halogenated vinyl aromatic monomers comprising reacting ring-halogenated (alpha- or beta-bromoethyl)benzenes or ring-halogenated (alpha- or beta-bromoethyl)toluenes with a strong aqueous alkali base in the presence of a poly(ethylene glycol) catalyst and an amine selected from the group consisting of the structure: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, and R.sub.5 are independently selected from the group consisting of hydrogen and C.sub.1 to C.sub.10 alkyl groups. The organic phase is separated, washed and neutralized and the ring-halogenated vinyl aromatic monomer is recovered.Type: GrantFiled: October 1, 1984Date of Patent: December 30, 1986Assignee: Ethyl CorporationInventor: Charles H. Kolich
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Patent number: 4599469Abstract: Process for the hydrogenation of functionally substituted acetylenic compounds employing catalyst comprising nickel boride on an inorganic oxide support is disclosed. Functionally-substituted acetylenic compounds are selectively reduced under mild reaction conditions to give functionally-substituted cis-olefinic compounds in high yield.Type: GrantFiled: May 29, 1984Date of Patent: July 8, 1986Assignee: Phillips Petroleum CompanyInventors: Ted H. Cymbaluk, Jim D. Byers, Marvin M. Johnson
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Patent number: 4594467Abstract: 3,5-Dichloro-.alpha.-methylstyrene is prepared from .alpha.-bromo-3,5-dichlorocumene by reaction with alkali metal hydroxide solutions in the presence of phase-transfer catalysts.Type: GrantFiled: August 6, 1985Date of Patent: June 10, 1986Assignee: Bayer AktiengesellschaftInventors: Karl-Wilhelm Henneke, Herbert Diehl, Karlfried Wedemeyer
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Patent number: 4571438Abstract: A process for the preparation of olefinic aldehydes and intermediates is disclosed. The condensation of an .alpha.,.omega.-dihalide with a metal acetylide gives an acetylenic halide which can be reduced to give an olefinic halide, then oxidized to give the desired olefinic aldehyde or the acetylenic halide can be oxidized first to give an acetylenic aldehyde and then reduced to give the desired olefinic aldehyde.Type: GrantFiled: March 21, 1985Date of Patent: February 18, 1986Assignee: Phillips Petroleum CompanyInventors: Jim D. Byers, Dennis S. Banasiak
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Patent number: 4540826Abstract: A process for the preparation of olefinic aldehydes and intermediates is disclosed. The condensation of an .alpha.,.omega.-dihalide with a metal acetylide gives an acetylenic halide which can be reduced to give an olefinic halide, then oxidized to give the desired olefinic aldehyde or the acetylenic halide can be oxidized first to give an acetylenic aldehyde and then reduced to give the desired olefinic aldehyde.Type: GrantFiled: August 12, 1983Date of Patent: September 10, 1985Assignee: Phillips Petroleum CompanyInventors: Dennis S. Banasiak, Jim D. Byers
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Patent number: 4489212Abstract: Arenes are reacted with allyl chloride to produce allylarenes and 2-chloropropyl- or propenylarenes using a catalyst comprising a metal oxide substrate having tantalum (V) halide/oxide bound to the surface of the substrate.Type: GrantFiled: October 25, 1983Date of Patent: December 18, 1984Assignee: Shell Oil CompanyInventor: Thomas H. Johnson
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Patent number: 4443625Abstract: The present invention relates to crop culture and is particularly concerned with practices for conserving soil nitrogen and for supplying the soil nitrogen requirements for plant nutrition. These practices involve the employment, as active agent, of a novel butane compound having the formula ##STR1## wherein X is H or ##STR2## R is H or C.sub.1 -C.sub.8 alkyl; R' is C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy or halo and n is an integer from 0 to 2.Type: GrantFiled: May 14, 1981Date of Patent: April 17, 1984Assignee: The Dow Chemical Co.Inventors: Jeffrey D. Griffith, Thomas M. Ozretich
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Patent number: 4423262Abstract: A process for the preparation of an ar-dibromostyrene which comprises aqueous alcoholic alkali dehydrobromination of 2-bromoethyl dibromobenzene in the presence of a phase transfer catalyst at a temperature of between about 0.degree. C. and about 150.degree. C. The ar-dibromostyrenes have the particular utility as a co-monomer for the preparation of a co-polymer exhibiting a flame retardancy.Type: GrantFiled: March 13, 1980Date of Patent: December 27, 1983Assignee: Ethyl CorporationInventor: Philip F. Jackisch
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Patent number: 4342704Abstract: A process for the preparation of a 1,1-dichloroalkene of the formula ##STR1## in which R.sup.1 is hydrogen or an optionally substituted alkyl, alkenyl, alkynyl, aralkyl or aryl radical, andR.sup.2 is an optionally substituted alkyl, alkenyl, alkynyl, aralkyl, aralkenyl or aryl radical, or cycloalkyl which is optionally substituted by halogen, alkyl, alkanoyl, carbamoyl, cyano or phenyl, orR.sup.1 and R.sup.2 together form a hydrocarbon chain which is optionally branched and/or optionally contains a fused benzene ring,comprising reacting an aldehyde or ketone of the formula ##STR2## with a dichloromethane-phosphonic acid ester of the formula ##STR3## in which R.sup.3 each independently is alkyl or phenyl or the two radicals R.sup.3 together are alkanediyl,in the presence of a base at a temperature between about -50.degree. and +50.degree. C.Type: GrantFiled: July 2, 1980Date of Patent: August 3, 1982Assignee: Bayer AktiengesellschaftInventors: Hellmut Hoffmann, Fritz Maurer, Uwe Priesnitz, Hans-Jochem Riebel
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Patent number: 4334111Abstract: Benzotrihalides are prepared by pyrolyzing a substituted phenyl trihaloacetate of the formula ##STR1## wherein each X is halo, nitro, alkyloxy, aryloxy, aralkyoxy, cyano, lower alkyl, haloalkyl, haloalkyloxy, alkenyl, haloalkenyl, carbamoyl, N,N-dialkylcarbamoyl, N,N-diarylcarbamoyl, or N,N-diaralkyloxy;Y is halo; andn is an integer of from 1 to 5. As an example, 4-chlorophenyl trichloroacetate is pyrolyzed at 550.degree. C. to 4-chlorobenzotrichloride.Type: GrantFiled: February 17, 1978Date of Patent: June 8, 1982Assignee: The Dow Chemical CompanyInventors: Ralph A. Davis, R. Garth Pews
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Patent number: 4292453Abstract: The present invention relates to the production of ring-halogenated styrene monomers of high purity. These are of value in the production of polymers which possess flame retardance. The process of the invention comprises reacting heterogenously ring halogenated beta-bromoethyl benzene with a strong aqueous alkali base in the presence of a quaternary phase transfer catalyst until substantially all the bromoethyl benzene has undergone reaction, separating the phases, washing and neutralizing the organic phase and recovering the ring-halogenated styrene monomer, which is the desired product.Type: GrantFiled: May 24, 1979Date of Patent: September 29, 1981Assignee: Makhteshim Chemical Works Ltd.Inventors: Stephen L. J. Daren, David Vofsi, Meir Asscher
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Patent number: 4267388Abstract: There is disclosed a novel process for preparing anti-inflammatory ethynylbenzene derivatives represented by the general formula I: ##STR1## wherein Y is hydrogen, halogen or loweralkyl of 1 to 3 carbon atoms; R represents a ring having the structure: ##STR2## wherein x is 1 to 3, or a ring of the structure: ##STR3## wherein Y' is hydrogen, halogen, loweralkyl of 1 to 3 carbon atoms and loweralkoxy of 1 to 3 carbon atoms; Y" is hydrogen or halogen; and Y"' is hydrogen or halogen, provided Y, Y', Y" and Y"' are not all hydrogen at the same time, by reacting a benzyl alcohol of formula V: ##STR4## with a sulfonyl chloride, reducing the sulfonate VI of the formula: ##STR5## and dehydrohalogenating the formed .beta.Type: GrantFiled: July 12, 1979Date of Patent: May 12, 1981Assignee: William H. Rorer, Inc.Inventors: Paul R. Darkes, Henry F. Campbell, George H. Douglas
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Patent number: 4230642Abstract: 1-Bromo-3,5-dichlorobenzene is reacted with magnesium in a solvent and acetone is added to react it with the reaction product and a mineral acid is added to hydrolyze the resulting .alpha.-(3,5-dichlorophenyl) isopropoxymagnesium bromide and then, the product is dehydrated to obtain 3,5-dichloro-.alpha.-methylstyrene. 3,5-Dichloro-.alpha.-methylstyrene is useful intermediate for various agricultural chemicals, medicines and dyes and also useful monomer for rubbers, plastics and resins.Type: GrantFiled: February 2, 1979Date of Patent: October 28, 1980Assignee: Ishihara Sangyo Kaisha LimitedInventors: Ryuzo Nishiyama, Kanichi Fujikawa, Yasuhiro Tsujii, Itaru Shigehara