O-containing Feed Patents (Class 585/437)
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Patent number: 6462246Abstract: A method of preparing an alkenyl-substituted aromatic hydrocarbon, which comprises alkenylating an aromatic hydrocarbon with an olefin using &bgr;-diketone together with a rhodium complex catalyst in the presence of oxygen.Type: GrantFiled: March 29, 2001Date of Patent: October 8, 2002Assignee: Nippon Mitsubishi Oil CorporationInventors: Takaya Matsumoto, Shinji Nishikawa, Hajime Yoshida
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Patent number: 6437207Abstract: Process for the preparation of styrene comprising the gas phase dehydration of 1-phenyl-ethanol at elevated temperature in the presence of a dehydration catalyst, wherein the dehydration catalyst consists of shaped alumina catalyst particles having a surface area (BET) in the range of from 80 to 140 m2/g and a pore volume (Hg) in the range of from 0.35 to 0.65 ml/g, of which 0.03 to 0.15 ml/g is in pores having a diameter of at least 1000 nm.Type: GrantFiled: November 9, 2000Date of Patent: August 20, 2002Assignee: Shell Oil CompanyInventors: Hendrik Dirkzwager, Marinus Van Zwienen
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Patent number: 6420620Abstract: A process for the preparation of styrene or substituted styrenes that includes the steps of: subjecting a feed containing 1-phenyl ethanol or substituted 1-phenyl ethanol to a dehydration treatment in the presence of a dehydration catalyst; subjecting the resulting product stream to a separation treatment, thus obtaining a stream containing styrene or substituted styrene and a residual fraction containing heavy ends; and converting at least part of these heavy ends to styrene or substituted styrenes by subjecting a stream containing these heavy ends to a cracking treatment in the presence of an acidic cracking catalyst.Type: GrantFiled: August 14, 2000Date of Patent: July 16, 2002Assignee: Shell Oil CompanyInventors: Johan Hendrik De Bie, Hendrik Dirkzwager, Robertus Raymundus Maria Overtoom, Marinus Van Zwienen
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Patent number: 6395946Abstract: Styrene or substituted styrenes are produced by a process comprising the gas phase dehydration of 1-phenyl ethanol or substituted 1-phenyl ethanol in the presence of a solid acidic catalyst comprising a zeolite and a binder material, wherein the weight ratio of zeolite to binder is in the range of from 1:99 to 90:10 and wherein the following relation applies: 0<K<5 with K=V/S×[(Pz×fz)+(Pb×fb)]½, wherein: V/S is the volume/surface ratio of the catalyst used in mm; fz is the weight fraction of zeolite present in the catalyst in grams zeolite per gram catalyst; fb is the weight fraction of binder present in the catalyst in grams binder per gram catalyst; pz is the intrinsic productivity of zeolite expressed as grams styrene produced per gram of the zeolite per hour, as measured for pure zeolite samples of small particle size (i.e., <0.Type: GrantFiled: August 14, 2000Date of Patent: May 28, 2002Assignee: Shell Oil CompanyInventors: Joseph Cornelis Van Giezen, Jean-Paul Lange, Carolus Matthias Anna Maria Mesters
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Patent number: 6156948Abstract: This invention relates to a method for the selective preparation of a styrene of formula (1) ##STR1## by reacting an acetophenone of formula (1) ##STR2## with hydrogen in the presence of a catalyst containing one of several oxides, in particular metal oxides, wherein the oxide contains an element form the groups Ia, IIa, IIIa, IVa, VIa, Ib, IIb, IVb, Vb, VIb, and/or VIII or an element from the lanthanide group. The catalyst contains preferably on or several oxides of the formula ZnM.sup.1.sub.b M.sup.2.sub.c O.sub.x, where M.sup.1 stands for at least one element from the Al, Zr, Ti and Si group, M.sup.2 stands for at least one element from the Cd, Cu, Ag, Ni, Co, Fe, Mn, Cr, Mo, Ta, Sc, W, V, Nb, Hf, Yt, B, In, Zn, Pb, Bi Se, Ga, Ge, Sb, As, Te group, or an element from the lanthanides, b=0-20, c=0-3, x corresponds to the number of oxygen atoms required for stoechiometric compensation, which results in accordance with the oxidation states of Zn, M.sup.1 and M.sup.2 or oxides of formula M.sup.3.sub.2 M.sup.Type: GrantFiled: July 27, 1999Date of Patent: December 5, 2000Assignee: Aventis Research & Technologies GmbH & Co. KGInventors: Rainer Roesky, Holger Borchert, Uwe Dingerdissen
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Patent number: 6127590Abstract: This invention relates generally to the field of chemical synthesis, and more specifically, to the field of oxidative coupling of olefinic compounds and aromatic compounds, to produce olefinically substituted aromatic compounds. More particularly, this invention relates to methods for oxidative coupling of olefinic compounds and aromatic compounds which employ a rhodium(III) acetylacetonate catalyst and a copper(II) redox agent in a reaction medium which does not comprise a carboxylic acid component. In one embodiment, this invention pertains to methods for the preparation of styrene by the oxidative coupling of ethylene (an olefinic compound) and benzene (an aromatic compound), in the presence of Rh(acac).sub.2 Cl(H.sub.2 O), as catalyst, and Cu(II)(CH.sub.3 COO).sub.2, as copper(II) redox agent, in which benzene is both a reactant and the reaction medium.Type: GrantFiled: March 26, 1999Date of Patent: October 3, 2000Assignee: Nippon Mitsubishi Oil CorporationInventors: Douglas Taube, Roy Periana, Takaya Matsumoto
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Patent number: 6080894Abstract: The propylene oxide and styrene co-production process generates a heavy residue byproduct containing metals, mainly sodium, which previously was adequate for use only as low quality fuel. According to the invention, the heavy residue is dehydrated in the presence of a strong inorganic acid at temperatures of 150-250.degree. C. and pressures below the atmospheric pressure to yield styrene and recover 2-phenylethanol, a compound used in the perfume industry, and a heavy residue substantially free of metals that may be used as fuel.Type: GrantFiled: March 17, 1998Date of Patent: June 27, 2000Assignee: Repsol Quimica S.A.Inventors: Juan Antonio Delgado Oyague, Pilar De Frutos Escrig, Ignacio Vic Fernandez
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Patent number: 6025530Abstract: The present invention relates generally to a method for treating phenol tar, and, more particularly to a method for separating valuable products from phenol tar by treating the tar with steam.Type: GrantFiled: February 4, 1998Date of Patent: February 15, 2000Assignee: General Electric CompanyInventors: Arkady Samuilovich Dyckman, Andrey Zinenkov, Boris Issakovich Gorovits, John W. Fulmer
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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: 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: 5446227Abstract: A process for co-production of an alkenyl aromatic compound such as, for example, styrene and t-butylstyrene, and an oxygenated sulfur-containing compound such as, for example, a sulfoxide or a sulfone is disclosed which comprises: (1) contacting, in the presence or absence of a catalyst, an .alpha.-methyl benzylic hydroperoxide with an organic sulfide compound to produce a mixture of an .alpha.-methyl benzylic hydroxide and an oxygenated sulfur-containing compound; (2) separating the .alpha.-methyl benzylic hydroxide from the sulfur-containing compound; (3) contacting the .alpha.-methyl benzylic hydroxide with a base to convert the .alpha.-methyl benzylic hydroxide to the alkenyl aromatic compound; and optionally, (4) recovering the alkenyl aromatic compound from the oxygenated sulfur-containing compound. The sulfoxide produced can be oxidized to a sulfone. The contacting of the .alpha.-methyl benzylic hydroxide with a base can also be carried out before the .alpha.Type: GrantFiled: September 7, 1993Date of Patent: August 29, 1995Assignee: Phillips Petroleum CompanyInventors: Paul J. DesLauriers, Michael S. Matson
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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: 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: 5191133Abstract: The selective formation of 2-acetonaphthalene is achieved by acetylating naphthalene in the presence of liquid hydrogen fluoride. The 2-acetonaphthalene can be separated from the formed 1-acetonaphthalene isomer by successive hydrogenation of the isomer mixture and dehydration. The hydrogenation is selective to the 2-isomer while the 1-acetonaphthalene remains unreacted. Upon completion, 2-vinylnaphthalene can be distilled off from the unreacted 1-acetonaphthalene.Type: GrantFiled: May 22, 1991Date of Patent: March 2, 1993Assignee: Hoescht Celanese CorporationInventor: Henry C. Linstid, III
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Patent number: 5008482Abstract: There is provided a process for producing a styrenic compound by reacting an aromatic compound with an aldehyde over an intermediate pore size molecular sieve catalyst. Such styrenic compounds include unsubstituted styrene and substituted styrene. Examples of such aromatic compounds include unsubstituted benzene and alkylbenzenes. An example of such an aldehyde is acetaldehyde. An example of such a catalyst is a ZSM-5 catalyst.Type: GrantFiled: December 26, 1989Date of Patent: April 16, 1991Assignee: Mobil Oil Corp.Inventors: Werner O. Haag, Rudolph M. Lago
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Patent number: 4751307Abstract: Disclosed are improved Wittig reaction processes wherein the Wittig reaction is conducted in an anisole containing solvent.Type: GrantFiled: February 27, 1987Date of Patent: June 14, 1988Assignee: Mallinckrodt, Inc.Inventor: Carl R. White
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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: 4499318Abstract: A modified zeolite catalyst composition and process for using the catalyst composition to alkylate toluene (or derivative thereof) with methanol to form e.g. styrene and ethylbenzene (or derivatives thereof) is disclosed. The catalyst composition is exemplified by a type X- or Y-zeolite modified with (1) at least one alkali metal selected from Cs, K, and Rb; (2) at least one metal selected from Li, Ce, Cr, and Ag; and (3) boron and/or phosphorus.Type: GrantFiled: July 2, 1984Date of Patent: February 12, 1985Assignee: Exxon Research & Engineering Co.Inventor: Huei-Cheng Liu
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Patent number: 4499317Abstract: A modified zeolite catalyst composition and process for using the catalyst composition to alkylate toluene (or derivative thereof) with methanol to form e.g. styrene and ethylbenzene (or derivatives thereof) is disclosed. The catalyst composition is exemplified by a type X- or Y-zeolite modified with (1) at least one alkali metal selected from Cs, K, and Rb; (2) at least one metal selected from Mn, Fe, Cu, and Zn; and (3) boron and/or phosphorus.Type: GrantFiled: July 2, 1984Date of Patent: February 12, 1985Assignee: Exxon Research & Engineering Co.Inventors: Huei-Cheng Liu, Ralph J. Spohn
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Patent number: 4479024Abstract: Toluene and formaldehyde produce styrene in a gas phase catalytic process using a basic hydroxide of Group I or II, at formaldehyde to toluene mole ratios of from 0.001 to 0.10.Type: GrantFiled: June 1, 1983Date of Patent: October 23, 1984Assignee: Ashland Oil, Inc.Inventors: Philippe M. Bruylants, Robert L. Garten
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Patent number: 4463204Abstract: A process for alkylating toluene (or derivative thereof) with methanol to form e.g. styrene and ethylbenzene (or derivatives thereof) using a modified low sodium content zeolite catalyst composition is disclosed. The zeolite catalyst composition is exemplified by a type X- or Y-zeolite modified with potassium and cesium through a sequential exchange.Type: GrantFiled: April 22, 1983Date of Patent: July 31, 1984Assignee: Exxon Research & Engineering Co.Inventor: Huei-Cheng Liu
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Patent number: 4443643Abstract: A process for the production of styrene wherein ethylene oxide and benzene are added to a reactor at a temperature between about 600.degree. F. and about 825.degree. F. in the presence of an aluminosilicate type catalyst. The reaction proceeds directly to form styrene within the reactor.Type: GrantFiled: May 23, 1983Date of Patent: April 17, 1984Assignee: Cosden Technology, Inc.Inventors: James M. Watson, Cleve Forward
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Patent number: 4440694Abstract: The invention relates to vinylstilbene compounds of the formula ##STR1## wherein Q is the grouping --COX or ##STR2## These compounds are obtained by reacting 1 molar equivalent of a compound of the formula II ##STR3## wherein X is chlorine, bromine or iodine, in the presence of a base and with the addition of palladium metal or of palladium compounds, as catalyst, which, under the reaction conditions, form labile palladium(O) compounds which do not contain phosphorus, with 1 molar equivalent of a compound of the formula III or with 1 molar equivalent of each of the compounds of the formulae III and IV ##STR4##Type: GrantFiled: May 8, 1981Date of Patent: April 3, 1984Assignee: Ciba-Geigy CorporationInventors: Daniel Bellus, Hans-Ulrich Blaser, Guglielmo Kabas, Dieter Reinehr, Alwyn Spencer, Kurt Weber
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Patent number: 4358409Abstract: Styryl-cyclopropane derivatives of the formula ##STR1## in which R.sup.9 represents independently of one another when n=2, halogen, cyano, nitro, or an optionally halogen-substituted alkyl, alkoxy, alkylthio or alkylenedioxy radical,n represents zero, 1, 2, 3, 4 or 5,R.sup.10 represents hydrogen or halogenandY represents acetyl, cyano or carbamoyl, are produced by reacting a benzylphosphonic acid ester of the formula ##STR2## in which R.sup.4 each independently represents alkyl or phenyl or together represent alkylene, with a formylcyclopropane derivative of the formula ##STR3## or by reacting an .alpha.-hydroxyphosphonic acid ester of the formula ##STR4## with an olefinating agent of the formula ##STR5## in which Z' represents a phosphorus-containing radical ##STR6## wherein R.sup.5 and R.sup.6 are identical or different and individually represent alkyl, phenyl, alkoxy or pehnoxy or R.sup.5 and R.sup.6 together represent alkanedioxy,R.sup.Type: GrantFiled: April 16, 1980Date of Patent: November 9, 1982Assignee: Bayer AktiengesellschaftInventors: Hellmut Hoffmann, Fritz Maurer, Uwe Priesnitz, Hans-Jochem Riebel
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Patent number: 4339605Abstract: Phenol pitch obtained as a bottoms fraction in the distillation of phenol deriving from the acid hydrolysis of cumene hydroperoxide is treated to recover therefrom desired products consisting of phenol, alpha-methylstyrene, cumene and acetone, by introducing steam and the phenol pitch, into a reactor in a weight ratio of from 0.01:1 to 1:1, withdrawing from the top of said reactor a vapor phase comprising said desired products, withdrawing from the bottom of said reactor a liquid phase consisting essentially of compounds of higher boiling point than said desired products, and operating at a pressure of 4-12 Kg/cm.sup.2, at a temperature of 320.degree.-400.degree. C., as measured in the liquid phase, and with a residence time of 0.5-10 hours.Type: GrantFiled: February 8, 1980Date of Patent: July 13, 1982Assignee: Euteco Impianti S.p.A.Inventors: Ferdinando Ligorati, Emanuele Sartorio
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Patent number: 4335055Abstract: Compounds of the formula I ##STR1## in which Z, Z.sub.1, R, m and p are as defined in patent claim 1, can be obtained in a simple and economical manner by a novel process wherein a halide of the formula II ##STR2## is reacted with a substituted or unsubstituted vinylbenzene or vinylnaphthalene derivative in the presence of a base and of certain palladium catalysts, such as palladium acetate. The compounds (I) or functional derivatives preparable therefrom are useful, for example, for the preparation of known dyes or fluorescent brighteners, or can be used directly as fluorescent brighteners or as scintillators.Type: GrantFiled: May 8, 1981Date of Patent: June 15, 1982Assignee: Ciba-Geigy CorporationInventors: Hans-Ulrich Blaser, Dieter Reinehr, Alwyn Spencer
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Patent number: 4319066Abstract: Cyclohexenyl and alkenyl aromatic compounds, such as cyclohexene and styrene, are prepared by a process comprising contacting a corresponding cyclohexyl or alkyl aromatic carboxylic acid, such as cyclohexyl carboxylic acid or 2-phenyl propionic acid, with a decarboxylation catalyst of the formulaM.sub.a M'.sub.b O.sub.xwhereM is copper or a combination of copper and molybdenum, andM' is at least one promoter element, such as a Group IA element.Type: GrantFiled: August 1, 1980Date of Patent: March 9, 1982Assignee: The Standard Oil CompanyInventors: Louis J. Velenyi, Serge R. Dolhyj, Andrew S. Krupa
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Patent number: 4273622Abstract: Residual products obtained in the catalytic dehydration of alpha-methylbenzyl alcohol are treated to recover monomeric styrene values by a process which comprises fractionally distilling the residual products in two stages under different temperature and time conditions.Type: GrantFiled: November 26, 1979Date of Patent: June 16, 1981Assignee: Halcon Research & Development Corp.Inventor: Mitchell Becker
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Patent number: 4270017Abstract: Para-xylene is selectively prepared by reacting toluene and a methylating agent in the presence of a phosphorus modified catalyst comprising a silica polymorph intermixed with an inorganic refractory oxide, said catalyst having an alkali content of less than about 1.3 milliequivalents per gram as available alkali.Type: GrantFiled: February 16, 1979Date of Patent: May 26, 1981Assignee: Union Oil Company of CaliforniaInventor: Dean A. Young
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Patent number: 4262157Abstract: Decarboxylation of carboxylic acids using diazabicycloalkenes and, if desired, also a simple copper salt, as the means for decarboxylation.Type: GrantFiled: March 27, 1980Date of Patent: April 14, 1981Assignee: Abbott LaboratoriesInventors: Yuji Hori, Yoshiaki Nagano, Hiroshi Taniguchi
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Patent number: 4250344Abstract: A process for making styrene by the cracking of beta-phenethyl acetate wherein the beta-phenethyl acetate is derived from the esterification of beta-phenethyl alcohol. The latter is derived from the homologation of benzyl alcohol-benzyl acetate mixtures. The esterification of the beta-phenethyl alcohol may be partial because it has been found that up to 20% by weight of beta-phenethyl alcohol may be fed to the cracking step and also converted to styrene. Benzyl alcohol and benzyl acetate can also be fed to the cracking step because it has been found that they are essentially inert at cracking conditions.Type: GrantFiled: October 25, 1978Date of Patent: February 10, 1981Assignee: Chem Systems Inc.Inventors: Martin B. Sherwin, Jimmy Y. Peress, Kenneth J. Gwozdz
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Patent number: 4236035Abstract: New organo-lithium initiators, their synthesis, and their use. The initiators have the formula: ##STR1## in which R" is either a hydrogen atom or a methyl radical; either n is 1, in which case R' = H and m and p are integers, the sum of which is between 0 and 10 inclusive, or n is 2, R' then being an alkyl radical of 2 to 8 carbon atoms and m =p =0; and R is an alkyl radical of 1 to 4 carbon atoms.The initiators are prepared by reacting compounds of the formula: ##STR2## with an alkyl-lithium RLi in a non-polar solvent in the absence of any polar solvent or complexing agent.The initiators are used to prepare polydienes of high stereoregularity by reacting with a diene, and the polydiene is used to prepare a three-block or star copolymer by reacting with an anionically polymerizable monomer.Type: GrantFiled: April 5, 1979Date of Patent: November 25, 1980Assignees: Societe Chimique des Charbonnages-CdF CHIMIE, Agence Nationale de Valorisation de la Recherche (ANVAR)Inventors: Pierre Sigwalt, Patrick Guyot, Michel Fontanille
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Patent number: 4233467Abstract: .alpha.-Alkylbenzyl alcohol and substituted .alpha.-alkylbenzyl alcohols are converted in high yield and purity to styrene and substituted styrenes by contacting the alcohol in vapor phase with a high efficiency silica gel catalyst.Type: GrantFiled: March 12, 1979Date of Patent: November 11, 1980Assignee: The Dow Chemical CompanyInventors: Junior J. Lamson, Richard H. Hall, Edward Stroiwas, Larry D. Yats
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Patent number: 4210606Abstract: Cumene hydroperoxide is decomposed to phenol and acetone using a halogen-substituted thiophenol as the catalyst.Type: GrantFiled: June 15, 1979Date of Patent: July 1, 1980Assignee: Gulf Research and Development CompanyInventors: Richard G. Austin, Wayne R. Pretzer, Thaddeus P. Kobylinski
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Patent number: 4207424Abstract: An improved process for the catalytic dehydration of alcohols to form unsaturated organic compounds is provided in which an alcohol is dehydrated in the presence of alumina catalysts which are pre-treated with an organic silylating agent at elevated temperature.Type: GrantFiled: August 9, 1978Date of Patent: June 10, 1980Assignee: Halcon Research & Development CorporationInventor: Charles N. Winnick