Having Alkenyl Moiety, E.g., Styrene, Etc. Patents (Class 585/435)
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Patent number: 5698755Abstract: The invention relates to a process for preparing monofunctional, bifunctional or polyfunctional aromatic olefins of the formula (I) ##STR1## by reaction of haloaromatics of the formula (II) ##STR2## with olefins of the formula (III) ##STR3## , wherein a palladium compound of the formula (IV) ##STR4## is used as the catalyst.Type: GrantFiled: June 21, 1995Date of Patent: December 16, 1997Assignee: Hoechst AGInventors: Matthias Beller, Hartmut Fischer, Wolfgang Anton Herrmann, Christoph Brossmer
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Patent number: 5679878Abstract: This invention relates to a vapor phase process for the production of an alkyl styrene by the catalytic dehydrogenation of tertiary butylethylbenzene in the presence of catalysts containing iron oxides under conditions which minimize the undesirable thermal degradation of the raw material and the product while maintaining good yield and selectivity with low production of by-products. Specifically, it has been discovered that these desired results may be obtained by conducting the subject reaction at relatively low temperatures of between about 1000.degree. F. and about 1100.degree. F. and by maintaining a low partial pressure (i.e., not greater than about 0.5 psi) of the alkyl ethylbenzene in the reaction mixture. The desired partial pressure of the alkyl ethylbenzene is obtained by carrying out the catalytic reaction at a pressure of between about 1 psia and about 30 psia with steam as a diluent, the weight ratio of steam to alkyl ethylbenzene being between about 3 and about 30.Type: GrantFiled: October 28, 1992Date of Patent: October 21, 1997Assignee: Deltech CorporationInventors: Shiou-Shan Chen, Joseph C. Peters, Lionel C. Allmand
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Patent number: 5659097Abstract: A process for producing a monoalkenyl aromatic hydrocarbon which comprises alkenylating a side chain of an aromatic hydrocarbon compound having at least one hydrogen atom at the .alpha.-position of a side chain (such as o-xylene) with a conjugated diene having 4 or 5 carbon atoms in the presence of a catalyst slurry prepared by adding an aromatic hydrocarbon compound to a catalyst comprising a alkali metal and an alkali metal compound. In the aforementioned process, it is particularly effective that the catalyst slurry is prepared by adding the aromatic hydrocarbon compound after the aromatic hydrocarbon compound has been deoxygenated and dehydrated by distillation, and the catalyst slurry thus prepared is supplied to the reaction system. According to the aforementioned process, an industrially useful monoalkenyl aromatic hydrocarbon compound, such as a monoalkenylbenzene, can be produced at a high selectivity, in a high yield, and with enhanced safety and stability for a long time.Type: GrantFiled: January 11, 1995Date of Patent: August 19, 1997Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Norio Fushimi, Makoto Takagawa
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Patent number: 5639928Abstract: The present invention relates to the improved liquid phase dehydration of 1-phenyl ethanol to styrene monomer, the improvement comprising the use of a residue formation inhibiting agent during the liquid phase dehydration.Type: GrantFiled: August 26, 1994Date of Patent: June 17, 1997Assignee: ARCO Chemical Technology, L.P.Inventors: Walter S. Dubner, Lawrence M. Candela
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Patent number: 5545786Abstract: Nitroxyl inhibitors in combination with some oxygen reduce the premature polymerization of vinyl aromatic monomers during the manufacturing processes for such monomers. Even small quantities of air used in combination with the nitroxyl inhibitors result in vastly prolonged inhibition times for said monomers.Type: GrantFiled: February 3, 1995Date of Patent: August 13, 1996Assignee: Ciba-Geigy CorporationInventors: Roland A. E. Winter, Volker H. von Ahn
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Patent number: 5545782Abstract: Nitroxyl inhibitors in combination with some oxygen reduce the premature polymerization of vinyl aromatic monomers during the manufacturing processes for such monomers. Even small quantities of air used in combination with the nitroxyl inhibitors result in vastly prolonged inhibition times for said monomers.Type: GrantFiled: May 17, 1995Date of Patent: August 13, 1996Assignee: Ciba-Geigy CorporationInventors: Roland A. E. Winter, Volker H. von Ahn
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Patent number: 5536870Abstract: A process for preparing olefin compounds of the formula ##STR1## where A is aryl, substituted aryl, heteroaryl, substituted heteroaryl, benzyl, substituted benzyl, vinyl or substituted vinyl and R.sub.2, R.sub.3 and R.sub.4 are hydrogen, alkyl, cycloalkyl, alkyl-substituted cycloalkyl, aryl, substituted aryl, alkoxy, alkythio, heteroaryl, substituted heteroaryl, alkanoyl, aroyl, substituted aroyl, heteroarylcarbonyl, substituted heteroarylcarbonyl, trifluoromethyl or halo, which comprises reacting an organic halide of the formula A-X where X is chloro, bromo or iodo with a vinyl or substituted vinyl compound of the formula ##STR2## where R.sub.2, R.sub.3 and R.sub.Type: GrantFiled: February 17, 1995Date of Patent: July 16, 1996Assignee: Albemarle CorporationInventor: Tse-Chong Wu
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Patent number: 5527977Abstract: Their is disclosed a process for producing a monoalkenyl aromatic hydrocarbon compound (e.g. 5-(o-tolyl)-2-pentene) which comprises the steps of alkenylating a side chain of an aromatic hydrocarbon compound having at lease one hydrogen atom bonded to .alpha.-position of the side chain (e.g. alkylbenzene) by the use of a conjugated diene having 4 to 5 carbon atoms (e.g. 1-3 butadiene) in the presence an alkali metal-based catalyst supported on a carrier; removing at least part of the catalyst from the resultant reaction product by separating the same; inactivating and optionally removing the catalyst contained in the reaction product; and thereafter distilling the reaction produce in liquid form to separate and recover the objective monoalkenyl aromatic hydrocarbon compound.Type: GrantFiled: June 27, 1994Date of Patent: June 18, 1996Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Makoto Takagawa, Kenichi Nakamura, Kinji Kato, Akio Hashimoto, Takayo Sasaki
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Patent number: 5502264Abstract: 1-pentene dimers of .alpha.-methylstyrenes are produced with high selectivity in good productivity by stirring 50 to 95 parts by weight of an .alpha.-methylstyrene in the presence of 50 to 5 parts by weight of an aqueous solution of a sulfonic acid, and a 1-pentene dimer having good preservative property is then collected by removing the sulfonic acid, adjusting the resulting reaction solution to pH 8 or higher and distilling the neutralized reaction solution.Type: GrantFiled: May 18, 1994Date of Patent: March 26, 1996Assignee: Goi Chemical Company, Ltd.Inventors: Hiroshi Nishizawa, Takayuki Saitoh, Tatsuo Itoh, Kiyotaka Mashita
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Patent number: 5491250Abstract: A crude vinylically unsaturated product formed from a palladium-complex-catalyzed reaction of a reactant halide selected from the group consisting of aryl, allyl, vinyl, and benzyl halides, and a reactant olefin having a vinylic hydrogen, wherein the reaction is carried out in the presence of a hydrogen halide acceptor, is purified by first contacting the crude product with a base that is stronger than the hydrogen halide acceptor, then heating the stronger base-contacted product. The purified product shows a marked reduction in concentration bromine and palladium impurities. The product can then be further purified by such methods as chromatography, crystallization, or distillation to achieve a product that is more suitable for applications where very low levels of inorganic impurities are required.Type: GrantFiled: March 23, 1995Date of Patent: February 13, 1996Assignee: The Dow Chemical CompanyInventors: Edmund J. Stark, John A. Schultz, Ernest L. Ecker, Robert A. DeVries
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Patent number: 5489731Abstract: Aromatic vinyl compounds of the formula IAr--CH.dbd.CHR Iwhere Ar is an aromatic radical, and R is hydrogen, C.sub.1 -C.sub.4 -alkyl or unsubstituted or substituted phenyl, are prepared by reacting an alcohol of the formula IIAr--CH.sub.2 OH IIor an ester of the formula III ##STR1## where R' is hydrogen or C.sub.1 -C.sub.4 -alkyl, in aqueous solution with a triarylphosphine and a strong acid and then, in the presence of a mineral base, with an aldehyde of the formula IVR--CHO IV.Type: GrantFiled: December 1, 1993Date of Patent: February 6, 1996Assignee: BASF AktiengesellschaftInventor: Klaus Ditrich
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Patent number: 5488192Abstract: In the production of styrene, spontaneous polymerization of styrene monomer causes reduced efficiency and as such it is desirable to prevent the formation of polymer by the addition of inhibitors. A known inhibiting composition is 3,5-di-tert-butyl-4-hydroxy-N,N-dimethylbenzyl amine and carboxylic acid, or an anhydride of said carboxylic acid which is added to a styrene-containing mixture. However large quantities are required and often portions of the inhibiting composition are not utilized resulting in nonproductive loss. The efficiency of the specific inhibitor can be improved by supplying air simultaneously with the inhibiting composition in a weight ratio of 3,5-di-tert-butyl-4-hydroxy-N,N-dimethylbenzyl amine to carboxylic acid to air, said ratio being 1:1-0.05:0.05-15.Type: GrantFiled: May 5, 1994Date of Patent: January 30, 1996Assignee: KourbatovInventors: Vladimir A. Kourbatov, Nataljya P. Boreyko, Valerii P. Zouev, Alexandr G. Liakumovich
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Patent number: 5481053Abstract: A process for preparing unsaturated dimers of .alpha.-methylstyrene comprising dimerizing .alpha.-methylstyrene using activated clay or acid clay as a catalyst, in which the dimerization is carried out in the presence of a carbonic acid ester, preferably ethylene carbonate, which process achieves high selectivity to unsaturated dimers with ease in controlling the reaction temperature.Type: GrantFiled: September 22, 1994Date of Patent: January 2, 1996Assignee: Mitsubishi Chemical CorporationInventors: Masashi Inaba, Shiroh Inui, Hideki Kurokawa, Fujio Mizutani
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Patent number: 5475176Abstract: The present invention relates to a process for preparing vinyl-substituted aromatic compounds of the formula (I) Ar--CH.dbd.CH.sub.2, where Ar is a phenyl group that may bear 1 to 5 substituents, naphthyl or anthryl or a naphthyl radical bearing 1 to 7 substituents or an anthryl radical bearing 1 to 8 substituents, or a mononuclear five-, six- or seven-membered heterocyclic aromatic group which contains an oxygen atom and/or one or two nitrogen atoms in the ring and may bear 1 to 5 substituents, wherein an arylamine of the formula (II) Ar--NH.sub.2, where Ar has the aforementioned meaning, is reacted in an organic acid with an organic nitrite of the formula (III) R--ONO, where R is an alkyl group having 1 to 18 carbon atoms, a phenyl radical which may bear 1 to 3 alkyl groups each having 1 to 4 carbon atoms, or is an alkylcarbonyl group having 2 to 5 carbon atoms, and ethylene in an organic solvent in the presence of a palladium(0) of palladium(II) compound at temperatures of 0.degree. to 35.degree. C.Type: GrantFiled: April 4, 1994Date of Patent: December 12, 1995Assignee: Hoechst AktiengesellschaftInventors: Matthias Beller, Heinz Strutz
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Patent number: 5430200Abstract: The present invention provides in a particular embodiment an improvement in the process for producing phenol by the acid-catalyzed cleavage of cumene hydroperoxide (CHP). The reactant stream fed to the cleavage reactor also includes the contaminant by-product dimethyl benzyl alcohol (DMBA) formed during the direct oxidation of cumene to CHP. This contaminant DMBA further reacts in the cleavage reactor to reduce the yield of phenol and produce undesirable and unreclaimable by-products. The improvement provided herein comprises performing the cleavage reaction at a reduced residence time of generally from one-half to five minutes, whereby the formation of .alpha.-methyl styrene from DMBA is promoted and the formation of the undesirable and unreclaimable by-products is reduced; .alpha.-methyl styrene is not only a useful by-product, but can be recycled and hydrogenated to the cumene starting material.Type: GrantFiled: September 16, 1994Date of Patent: July 4, 1995Assignee: Hercules IncorporatedInventor: Horace E. Hood
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Patent number: 5386058Abstract: A method for producing polymethine dyes comprising the steps of:(a) reacting a 1,1-diaryl-2-metallo-ethene with an .omega., .omega.,-diaryl-polyalkene-aldehyde in an anhydrous solvent under an inert atmosphere; and(b) neutralizing the reaction mixture from step (a) with an acid, thereby producing a polymethine dye.Type: GrantFiled: October 29, 1993Date of Patent: January 31, 1995Assignee: Minnesota Mining and Manufacturing CompanyInventor: Roger A. Mader
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Patent number: 5371305Abstract: The present invention provides in a particular embodiment an improvement in the process for producing phenol by the acid-catalyzed cleavage of cumene hydroperoxide (CHP). The reactant stream fed to the cleavage reactor also includes the contaminant by-product dimethyl benzyl alcohol (DMBA) formed during the direct oxidation of cumene to CHP. This contaminant DMBA further reacts in the cleavage reactor to reduce the yield of phenol and produce undesirable and unreclaimable by-products. The improvement provided herein comprises performing the cleavage reaction at a reduced residence time of generally from one-half to five minutes, whereby the formation of .alpha.-methyl styrene from DMBA is promoted and the formation of the undesirable and unreclaimable by-products is reduced; .alpha.-methyl styrene is not only a useful by-product, but can be recycled and hydrogenated to the cumene starting material.Type: GrantFiled: December 31, 1992Date of Patent: December 6, 1994Assignee: Hercules IncorporatedInventor: Horace E. Hood
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Patent number: 5367098Abstract: A process for producing a monoalkenyl aromatic hydrocarbon compound which comprises alkenylating a side chain of an aromatic hydrocarbon compound having at least one hydrogen atom bonded at an .alpha.-position of the side chain (such as xylene) with a conjugated diene having 4 or 5 carbon atoms (such as butadiene) in the presence of a catalyst comprising a mixture obtained by heat treating metallic sodium together with a mixture of an aluminum oxide and a potassium compound in an inert gas atmosphere. The process produces a commercially useful monoalkenyl aromatic hydrocarbon compounds in a high yields and at a low cost with enhanced safety.Type: GrantFiled: April 15, 1993Date of Patent: November 22, 1994Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Norio Fushimi, Ko Kedo, Kenji Inamasa, Makoto Takagawa
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Patent number: 5336821Abstract: A process for the alkylation of aromatic hydrocarbons such as cumene and ethylbenzene is disclosed. A portion of the effluent stream from an alkylation reactor passes through an indirect heat exchanger to transfer heat to a flashed stream containing the product aromatic hydrocarbons. The heat exchanger recovers the exothermic heat of reaction from the effluent stream for use elsewhere in the process. This method of heat exchange is especially useful in alkylation processes where the temperature of the effluent stream is relatively low, such as where the alkylation reactor contains a zeolite catalyst.Type: GrantFiled: May 6, 1993Date of Patent: August 9, 1994Assignee: UOPInventors: Richard R. DeGraff, Peter J. Van Opdorp, Russell C. Schulz
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Patent number: 5336822Abstract: 4-Vinylcyclohexene is converted to styrene in the presence of a catalyst comprising tin, antimony, and oxygen. The feed stream to be contacted with the catalyst comprises water, 4-vinylcyclohexene, and oxygen. A ratio of water to 4-vinylcyclohexene above about 12:1, preferably above about 14:1, significantly increases the half-life of the catalyst. The catalyst is prepared by coprecipitating a tin chloride and an antimony chloride followed by calcination of the precipitate at a temperature in the range from 850.degree. C. to 1000.degree. C.Type: GrantFiled: June 14, 1993Date of Patent: August 9, 1994Assignee: The Dow Chemical CompanyInventor: Dennis A. Hucul
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Patent number: 5334794Abstract: A process for producing a monoalkenyl aromatic hydrocarbon compound which comprises alkenylating a side chain of an aromatic hydrocarbon compound having at least one hydrogen atom bonded at an .alpha.-position of the side chain (such as xylene) with a conjugated diene having 4 or 5 carbon atoms (such as butadiene) in the presence of a catalyst comprising a mixture obtained by heat treating metallic sodium together with a mixture of a zirconium oxide and a potassium compound in an inert gas atmosphere. An industrially useful monoalkenyl aromatic hydrocarbon compound is produced in a high yield at a low cost with enhanced safety from a specific aromatic hydrocarbon compound and a specific conjugated diene compound.Type: GrantFiled: April 15, 1993Date of Patent: August 2, 1994Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Norio Fushimi, Ko Kedo, Kenji Inamasa, Makoto Takagawa
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Patent number: 5300719Abstract: Aromatic compounds such as ethylbenzene and styrene are produced by contacting butadiene or 4-vinylcyclohexene in a flow reactor with a magnesium oxide, zinc oxide, calcium oxide, strontium oxide, or barium oxide. The products of the process contain low levels of xylene.Type: GrantFiled: July 9, 1992Date of Patent: April 5, 1994Assignee: The Dow Chemical CompanyInventor: Ronald W. Diesen
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Patent number: 5276235Abstract: In the co-production of propylene oxide and styrene monomer, there is produced a sodium-containing heavy residue stream previously suitable only as a low grade fuel. In accordance with the invention, the heavy residue stream is contacted with acid having a molar concentration with respect to water above that which corresponds to the product salt solubility limit, and the resulting mixture is phase separated into an aqueous sodium salt-containing slurry phase and an organic phase reduced in sodium.Type: GrantFiled: February 19, 1993Date of Patent: January 4, 1994Assignee: ARCO Chemical Technology, L.P.Inventor: Walter S. Dubner
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Patent number: 5264646Abstract: A process for preparing a vinylically-unsaturated product compound comprises reacting a halogenated organic compound with a hydrolytically-stable, vinylically-unsaturated precursor compound in the presence of (a) a homogeneous zerovalent palladium catalyst complex, (b) an organic hydrogen halide acceptor and (c) a diluent, wherein the diluent is water or an aqueous solution containing up to 95% by volume of an organic solvent. The halogenated organic compound is selected from aryl halides, benzyl halides or vinylic halides. The hydrolytically-stable, vinylically-unsaturated precursor compound is selected from organosilicon compounds, hydrocarbon compounds or compounds containing at least one of an oxygen atom, a nitrogen atom, a sulfur atom, a phosphorus atom or a combination thereof.Type: GrantFiled: March 28, 1991Date of Patent: November 23, 1993Assignee: The Dow Chemical CompanyInventors: Robert A. DeVries, Gregory F. Schmidt, Hughie R.* Frick, Bonnie Frick
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Patent number: 5258567Abstract: This invention relates to a process for the dehydrogenation of C.sub.2 -C.sub.10 hydrocarbons at dehydrogenation conditions with a pillared mica catalyst which contains an active metal selected from the group consisting of Pt, Cr and mixtures thereof, and a first modifier metal selected from the group consisting of Sn, Ga and mixtures thereof. The micas may also contain a second modifier metal selected from the group consisting of alkali metals, alkaline earth metals, and rare earth metals, and mixtures thereof.Type: GrantFiled: August 26, 1992Date of Patent: November 2, 1993Assignee: Exxon Research and Engineering CompanyInventors: Michael C. Kerby, Kenneth L. Riley, Fred M. Long, Jack W. Johnson, John F. Brody
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Patent number: 5238998Abstract: A toner composition comprised of multiblock or liquid glass resin particles with a glass transition temperature of between from about 20.degree. C. to about 65.degree. C., and pigment particles.Type: GrantFiled: October 5, 1992Date of Patent: August 24, 1993Assignee: Xerox CorporationInventors: Timothy J. Fuller, Samuel Kaplan, Michael J. Levy, Joseph D. Geiser, Richard B. Lewis, William M. Prest, Jr.
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Patent number: 5210354Abstract: In the co-production oxide and styrene monomer, there is produced a sodium-containing heavy residue stream previously suitable only as a low grade fuel. In accordance with the invention, the heavy residue stream is contacted with aqueous acid, and the resulting mixture is phase separated into an aqueous sodium-containing phase and an organic phase reduced in sodium, and at least a portion of the organic phase reduced in sodium is converted to styrene monomer.Type: GrantFiled: May 8, 1992Date of Patent: May 11, 1993Assignee: ARCO Chemical Technology, L.P.Inventors: Walter S. Dubner, Robert N. Cochran
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Patent number: 5180872Abstract: The title compounds can be prepared by reaction of a styrene derivative with ethylene in the presence of a nickel catalyst which carries a phosphorus-oxygen chelate ligand, at a temperature of 20.degree.to 160.degree. C. and an ethylene pressure of 1 to 200 bar. Styrene derivatives extended with ethylene, of the formula ##STR1## in which R.sup.19 denotes hydrogen, C.sub.1 -C.sub.4 -alkyl, vinyl or chlorine and R.sup.38 denotes C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl, C.sub.2 -C.sub.7 -acyl, flourine, chlorine or bromine andm assumes values of 4-104,with the exception of compounds wherein R.sup.19 denotes hydrogen and R.sup.38 denotes i-butyl or benzoyl, and m assumes the value 4, are new.Type: GrantFiled: May 23, 1991Date of Patent: January 19, 1993Assignee: Bayer AktiengesellschaftInventor: Karl-Heinz A. O. Starzewski
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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: 5081251Abstract: Stilbene compounds of the general formula Ia, Ib or IcR.sup.1 R.sup.2 R.sup.3 Ar.sup.1 --CH.dbd.CH--Ar.sup.3 R.sup.4 R.sup.5 R.sup.6 (Ia)R.sup.1 R.sup.2 R.sup.3 Ar.sup.1 --CH.dbd.CH--Ar.sup.2 R.sup.4 R.sup.5 R.sup.6 --CH.dbd.CH--Ar.sup.3 R.sup.7 R.sup.8 R.sup.9 (Ib)R.sup.1 R.sup.2 R.sup.3 Ar.sup.1 --CH.dbd.CH--Ar.sup.2 (CH.sub.2).sub.n Ar.sup.3 --CH.dbd.CH--Ar.sup.4 R.sup.4 R.sup.5 R.sup.6 (Ic)where Ar.sup.1 to Ar.sup.4 are identical or different aromatic or quasi-aromatic radicals and n is from 0 to 20 and where either at least one of the radicals R.sup.1 to R.sup.6 or R.sup.9 is hydrocarbon-solubilizing alkyl, alkoxy, dialkylamino or diarylamino of 4 or more carbon atoms in the alkyl moiety or, if formula Ic contains no radicals R.sup.1 to R.sup.6, n is not less than 4, are prepared by metalating a toluene/xylene analog R.sup.1 R.sup.2 R.sup.3 ArCH.sub.3 or H.sub.3 CR.sup.4 R.sup.5 R.sup.6 ArCH.sub.Type: GrantFiled: September 7, 1989Date of Patent: January 14, 1992Assignee: BASF AktiengesellschaftInventors: Dietmar Bender, Klaus Bronstert
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Patent number: 5030784Abstract: The instant invention relates to a process for converting methyl- and/or ethyl-substituted benzene or naphthalene and butadiene to 4-aryl-1-butene or 4-aryl-1-pentene and propylene by:a) reacting a methyl- and/or ethyl-substituted benzene or naphthalene and 1,3-butadiene in the presence of an alkali metal catalyst,b) reacting the butenylated reaction product of step a) with ethylene in the presence of of a disproportionation catalyst, andc) separating from the reaction product of step b) product 4-aryl-1-butene or 4-aryl-1-pentene and propylene.Type: GrantFiled: February 26, 1990Date of Patent: July 9, 1991Assignee: Shell Oil CompanyInventor: Lynn H. Slaugh
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Patent number: 5008480Abstract: The instant invention relates to a process for converting toluene and butadiene to styrene and 1-pentene by:(a) reacting touene and 1,3-butadiene in the presence of an alkali metal catalyst,(b) contacting the butenylated reaction product of step (a) with a double bond isomerization catalyst at a temperature sufficient to cause double isomerization,(c) reacting the isomerized product of step (b) with ethylene in the presence of a disproportionation catalyst, and(d) separating from the reaction product of step (c) product styrene and 1-pentene.Type: GrantFiled: February 26, 1990Date of Patent: April 16, 1991Assignee: Shell Oil CompanyInventor: Lynn H. Slaugh
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Patent number: 4982034Abstract: A process to purify t-butylstyrene from product containing substantial amounts of t-butylethylbenzene and small amounts of alkenyl-substituted styrene impurities by a combination of vacuum fractionation and vacuum evaporation in the presence a polymerization inhibitor, and treatment with a carbonaceous adsorbent. Such a product to be purified can be prepared by catalytically, oxidatively dehydrogenating over an alkaline pyrophosphate in the vapor phase t-butylethylbenzene containing about 95 wt. % or more of the p-isomer which can be made by alkylating ethylbenzene with isobutylene in a controlled manner in the presence of cooled concentrated sulfuric acid.Type: GrantFiled: December 19, 1989Date of Patent: January 1, 1991Assignee: Amoco CorporationInventors: Eric J. Moore, Marc L. Kullberg, Lori B. Lane
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Patent number: 4962252Abstract: Alkenyl-substituted benzene derivatives are produced by oxidatively coupling at elevated temperature a benzene having at least one activated saturated hydrocarbyl substituent in vapor form with a gaseous paraffinic hydrocarbon in the presence of a gaseous oxidant and as catalyst therefor a binary metallic or multimetallic composition capable of oxidatively coupling methane.Type: GrantFiled: July 25, 1989Date of Patent: October 9, 1990Assignee: The British Petroleum Company p.l.c.Inventor: Steven R. Wade
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Patent number: 4929786Abstract: Preparation of 1-aryl-1-alkenes by dehydration of 1-aryl-1-alkanols in the presence of a substance promoting elimination of water, the substance being a triester of phosphorous acid in which at least one of the radicals is an aryl group.The products are suitable as, inter al., initiators for anionic polymerization.Type: GrantFiled: October 28, 1988Date of Patent: May 29, 1990Assignee: BASF AktiengesellschaftInventors: Walter Himmele, Kaspar Bott, Klaus Bronstert
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Patent number: 4851599Abstract: Catalysis of the reaction to produce styrene from n-octane in the presence of catalysts comprising a dehydrogenation metal and a microporous crystalline material containing a modifier selected from the group consisting of tin, lead and thallium, is described.Type: GrantFiled: June 24, 1988Date of Patent: July 25, 1989Assignee: Mobil Oil CorporationInventor: Ralph M. Dessau
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Patent number: 4827070Abstract: An isobutylbenzene (IBB) is produced from an isobutenylcyclohexane (IBCH) by contacting at elevated temperature the IBCH in the presence of a molecular oxygen-containing gas with a catalyst comprising a supported transition metal in the form of the elemental metal and/or a compound thereof, for example palladium supported on alumina.Type: GrantFiled: March 7, 1988Date of Patent: May 2, 1989Assignee: BP Chemicals LimitedInventors: Alexander G. Kent, Derek K. MacAlpine
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Patent number: 4822942Abstract: An indium containing crystalline microporous material also containing a dehydrogenation component exhibits high selectivity for the aromatization of a normal paraffin to styrene, under dehydrocyclization conditions.Group VIII metal-containing non-acidic crystalline microporous indium containing materials are highly selective catalysts for styrene production from n-octane.Type: GrantFiled: July 1, 1988Date of Patent: April 18, 1989Assignee: Mobil Oil CorporationInventors: Ralph M. Dessau, Ernest W. Valyocsik
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Patent number: 4822937Abstract: A process for the production of isobutylbenzenes in particular, isobutylbenzene itself, is provided. The process is in two stages and comprises (1) reacting a vinylcyclohexane with an isoolefin of formula (R)(R.sup.1)C.dbd.C(CH.sub.3).sub.2 in the presence of a dismutation catalyst to produce an isobutenylcyclohexene and (2) contacting the isobutenylcyclohexene with a dehydroisomerisation catalyst to produce an isobutylbenzene. Examples of vinylcyclohexenes which can be used include 4-vinylcyclohexene and styrene.Type: GrantFiled: May 24, 1988Date of Patent: April 18, 1989Assignee: BP Chemicals LimitedInventors: Derek K. MacAlpine, Malcolm J. Lawrenson
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Patent number: 4734824Abstract: An electrical insulating oil which is suitable for use in impregnating electrical appliances such as capacitors, cables and transformers, especially those in which plastic materials are used partially or totally as dielectrics or insulating materials, and electrical appliances that are impregnated with the above electrical insulating oil. The electrical insulating oil of the invention contains at least one monoolefin and/or diolefin having three condensed or non-condensed aromatic rings.Type: GrantFiled: June 23, 1986Date of Patent: March 29, 1988Assignee: Nippon Petrochemicals Company, LimitedInventors: Atsushi Sato, Keiji Endo, Shigenobu Kawakami, Hitoshi Yanagishita, Shozo Hayashi
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Patent number: 4713458Abstract: Ketones and aldehydes are converted to ethenylidene-containing compounds by reaction thereof with dimethyl carbonate and a phosphine compound.Type: GrantFiled: August 21, 1984Date of Patent: December 15, 1987Assignee: The Dow Chemical CompanyInventors: Kevin A. Frazier, James M. Renga
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Patent number: 4703124Abstract: A process for introduction of styrenes in the side chain of substituted aromatic compounds, said side chain containing at least one hydrogen atom in the .alpha.-position thereof, is disclosed, comprising reacting the styrenes and the substituted aromatic compounds in the presence of (A) an alkali metal and (B) a compound containing a benzyloxy group or alkyl and/or aryl-substituted benzyloxy group. Use of (A) and (B) as a reaction accelerator permits to introduce the styrenes in the side chain of the substituted aromatic compounds in high yield and selectivity.Type: GrantFiled: December 19, 1985Date of Patent: October 27, 1987Assignee: Idemitsu Kosan Company LimitedInventors: Toshiyuki Tsubouchi, Tomiyasu Minokami, Nobuaki Shimizu
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Patent number: 4654451Abstract: Vinyl aromatic compounds are stabilized against undesired polymerization by adding to the vinyl aromatic compounds small amounts of mixtures of alkyl-substituted p-nitrosophenols and p-nitrosophenol.Type: GrantFiled: December 27, 1985Date of Patent: March 31, 1987Assignee: Atlantic Richfield CompanyInventors: Richard F. Miller, Marilyn W. Blaschke
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Patent number: 4654450Abstract: Vinyl aromatic compounds are stabilized against undesired polymerization by adding to the vinyl aromatic compounds small amounts of a N,N-dialkylhydroxylamine and an alkyl benzene sulfonic acid.Type: GrantFiled: February 24, 1986Date of Patent: March 31, 1987Assignee: Atlantic Richfield CompanyInventor: Richard F. Miller
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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: 4642405Abstract: For the preparation of methallylbenzene (.alpha.-olefin) and isobutenylbenzene (.beta.-olefin), and their p-substituted alkyl derivatives of Formulae 1 and 2, respectively, thermal cracking of neophyl chloride and the corresponding p-substituted neophyl chlorides of Formula 3 is performed, in the presence of an inhibitor for radical polymerization, with the resultant cracked product olefins of Formula 2 then isomerized to the corresponding .alpha.-olefin of Formula 1 by a further distillation in the presence of a mixture containing a basic compound and a polar solvent.Type: GrantFiled: February 18, 1986Date of Patent: February 10, 1987Assignee: Huels AktiengesellschaftInventor: Manfred Kaufhold
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Patent number: 4621302Abstract: An electrical insulating oil which is suitable for use in impregnating electrical appliances such as capacitors, cables and transformers, especially those in which plastic materials are used partially or totally as dielectrics or insulating materials, and electrical appliances that are impregnated with the above electrical insulating oil. The electrical insulating oil of the invention contains at least one monoolefin and/or diolefin having three condensed or non-condensed aromatic rings.Type: GrantFiled: March 13, 1985Date of Patent: November 4, 1986Assignee: Nippon Petrochemicals Company, LimitedInventors: Atsushi Sato, Keiji Endo, Shigenobu Kawakami, Hitoshi Yanagishita, Shozo Hayashi
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Patent number: 4620055Abstract: The present invention provides a novel process for the preparation of styrene, stilbene, and/or substituted derivatives thereof. The process involves the reaction of an aryl sulfonyl chloride with an olefinic compound in the presence of a catalytic amount of a metal catalyst consisting essentially of palladium.Type: GrantFiled: October 7, 1985Date of Patent: October 28, 1986Assignee: Eastman Kodak CompanyInventors: Carl M. Lentz, James R. Overton, David D. Cornell
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Patent number: 4618914Abstract: An improved electrical insulating oil which is stable in refining treatment and good electrical properties are maintained under high temperature conditions, and oil-filled electrical appliances impregnated therewith. The electrical insulating oil comprises 1,1,-diarylalkenes which are represented by the following general formula (I): ##STR1## wherein R.sub.1 to R.sub.4 's are the same or different and each of them is a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, and m and n are integers from 0 to 3, inclusive.Type: GrantFiled: February 28, 1985Date of Patent: October 21, 1986Assignee: Nippon Petrochemicals Company, LimitedInventors: Atsushi Sato, Keiji Endo, Shigenobu Kawakami, Hitoshi Yanagishita, Shozo Hayashi
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Patent number: 4571443Abstract: Certain benzylic and allylic compounds are catalytically oxidatively dehydrodimerized wherein the molecular oxygen oxidant is separated from the substrate by a gas impervious catalyst membrane that conducts oxide ions from the surface of the catalyst membrane wall to the opposite surface thereof which is in contact with the substrate.Type: GrantFiled: July 23, 1985Date of Patent: February 18, 1986Assignee: The Standard Oil CompanyInventors: Robert DiCosimo, James D. Burrington, Robert K. Grasselli