O-containing Feed Patents (Class 585/437)
  • Patent number: 6462246
    Abstract: 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: Grant
    Filed: March 29, 2001
    Date of Patent: October 8, 2002
    Assignee: Nippon Mitsubishi Oil Corporation
    Inventors: Takaya Matsumoto, Shinji Nishikawa, Hajime Yoshida
  • Patent number: 6437207
    Abstract: 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: Grant
    Filed: November 9, 2000
    Date of Patent: August 20, 2002
    Assignee: Shell Oil Company
    Inventors: Hendrik Dirkzwager, Marinus Van Zwienen
  • Patent number: 6420620
    Abstract: 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: Grant
    Filed: August 14, 2000
    Date of Patent: July 16, 2002
    Assignee: Shell Oil Company
    Inventors: Johan Hendrik De Bie, Hendrik Dirkzwager, Robertus Raymundus Maria Overtoom, Marinus Van Zwienen
  • Patent number: 6395946
    Abstract: 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: Grant
    Filed: August 14, 2000
    Date of Patent: May 28, 2002
    Assignee: Shell Oil Company
    Inventors: Joseph Cornelis Van Giezen, Jean-Paul Lange, Carolus Matthias Anna Maria Mesters
  • Patent number: 6156948
    Abstract: 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: Grant
    Filed: July 27, 1999
    Date of Patent: December 5, 2000
    Assignee: Aventis Research & Technologies GmbH & Co. KG
    Inventors: Rainer Roesky, Holger Borchert, Uwe Dingerdissen
  • Patent number: 6127590
    Abstract: 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: Grant
    Filed: March 26, 1999
    Date of Patent: October 3, 2000
    Assignee: Nippon Mitsubishi Oil Corporation
    Inventors: Douglas Taube, Roy Periana, Takaya Matsumoto
  • Patent number: 6080894
    Abstract: 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: Grant
    Filed: March 17, 1998
    Date of Patent: June 27, 2000
    Assignee: Repsol Quimica S.A.
    Inventors: Juan Antonio Delgado Oyague, Pilar De Frutos Escrig, Ignacio Vic Fernandez
  • Patent number: 6025530
    Abstract: 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: Grant
    Filed: February 4, 1998
    Date of Patent: February 15, 2000
    Assignee: General Electric Company
    Inventors: Arkady Samuilovich Dyckman, Andrey Zinenkov, Boris Issakovich Gorovits, John W. Fulmer
  • Patent number: 5639928
    Abstract: 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: Grant
    Filed: August 26, 1994
    Date of Patent: June 17, 1997
    Assignee: ARCO Chemical Technology, L.P.
    Inventors: Walter S. Dubner, Lawrence M. Candela
  • Patent number: 5489731
    Abstract: 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: Grant
    Filed: December 1, 1993
    Date of Patent: February 6, 1996
    Assignee: BASF Aktiengesellschaft
    Inventor: Klaus Ditrich
  • Patent number: 5446227
    Abstract: 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: Grant
    Filed: September 7, 1993
    Date of Patent: August 29, 1995
    Assignee: Phillips Petroleum Company
    Inventors: Paul J. DesLauriers, Michael S. Matson
  • Patent number: 5276235
    Abstract: 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: Grant
    Filed: February 19, 1993
    Date of Patent: January 4, 1994
    Assignee: ARCO Chemical Technology, L.P.
    Inventor: Walter S. Dubner
  • Patent number: 5210354
    Abstract: 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: Grant
    Filed: May 8, 1992
    Date of Patent: May 11, 1993
    Assignee: ARCO Chemical Technology, L.P.
    Inventors: Walter S. Dubner, Robert N. Cochran
  • Patent number: 5191133
    Abstract: 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: Grant
    Filed: May 22, 1991
    Date of Patent: March 2, 1993
    Assignee: Hoescht Celanese Corporation
    Inventor: Henry C. Linstid, III
  • Patent number: 5008482
    Abstract: 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: Grant
    Filed: December 26, 1989
    Date of Patent: April 16, 1991
    Assignee: Mobil Oil Corp.
    Inventors: Werner O. Haag, Rudolph M. Lago
  • Patent number: 4751307
    Abstract: Disclosed are improved Wittig reaction processes wherein the Wittig reaction is conducted in an anisole containing solvent.
    Type: Grant
    Filed: February 27, 1987
    Date of Patent: June 14, 1988
    Assignee: Mallinckrodt, Inc.
    Inventor: Carl R. White
  • Patent number: 4703124
    Abstract: 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: Grant
    Filed: December 19, 1985
    Date of Patent: October 27, 1987
    Assignee: Idemitsu Kosan Company Limited
    Inventors: Toshiyuki Tsubouchi, Tomiyasu Minokami, Nobuaki Shimizu
  • Patent number: 4499318
    Abstract: 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: Grant
    Filed: July 2, 1984
    Date of Patent: February 12, 1985
    Assignee: Exxon Research & Engineering Co.
    Inventor: Huei-Cheng Liu
  • Patent number: 4499317
    Abstract: 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: Grant
    Filed: July 2, 1984
    Date of Patent: February 12, 1985
    Assignee: Exxon Research & Engineering Co.
    Inventors: Huei-Cheng Liu, Ralph J. Spohn
  • Patent number: 4479024
    Abstract: 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: Grant
    Filed: June 1, 1983
    Date of Patent: October 23, 1984
    Assignee: Ashland Oil, Inc.
    Inventors: Philippe M. Bruylants, Robert L. Garten
  • Patent number: 4463204
    Abstract: 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: Grant
    Filed: April 22, 1983
    Date of Patent: July 31, 1984
    Assignee: Exxon Research & Engineering Co.
    Inventor: Huei-Cheng Liu
  • Patent number: 4443643
    Abstract: 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: Grant
    Filed: May 23, 1983
    Date of Patent: April 17, 1984
    Assignee: Cosden Technology, Inc.
    Inventors: James M. Watson, Cleve Forward
  • Patent number: 4440694
    Abstract: 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: Grant
    Filed: May 8, 1981
    Date of Patent: April 3, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: Daniel Bellus, Hans-Ulrich Blaser, Guglielmo Kabas, Dieter Reinehr, Alwyn Spencer, Kurt Weber
  • Patent number: 4358409
    Abstract: 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: Grant
    Filed: April 16, 1980
    Date of Patent: November 9, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hellmut Hoffmann, Fritz Maurer, Uwe Priesnitz, Hans-Jochem Riebel
  • Patent number: 4339605
    Abstract: 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: Grant
    Filed: February 8, 1980
    Date of Patent: July 13, 1982
    Assignee: Euteco Impianti S.p.A.
    Inventors: Ferdinando Ligorati, Emanuele Sartorio
  • Patent number: 4335055
    Abstract: 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: Grant
    Filed: May 8, 1981
    Date of Patent: June 15, 1982
    Assignee: Ciba-Geigy Corporation
    Inventors: Hans-Ulrich Blaser, Dieter Reinehr, Alwyn Spencer
  • Patent number: 4319066
    Abstract: 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: Grant
    Filed: August 1, 1980
    Date of Patent: March 9, 1982
    Assignee: The Standard Oil Company
    Inventors: Louis J. Velenyi, Serge R. Dolhyj, Andrew S. Krupa
  • Patent number: 4273622
    Abstract: 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: Grant
    Filed: November 26, 1979
    Date of Patent: June 16, 1981
    Assignee: Halcon Research & Development Corp.
    Inventor: Mitchell Becker
  • Patent number: 4270017
    Abstract: 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: Grant
    Filed: February 16, 1979
    Date of Patent: May 26, 1981
    Assignee: Union Oil Company of California
    Inventor: Dean A. Young
  • Patent number: 4262157
    Abstract: Decarboxylation of carboxylic acids using diazabicycloalkenes and, if desired, also a simple copper salt, as the means for decarboxylation.
    Type: Grant
    Filed: March 27, 1980
    Date of Patent: April 14, 1981
    Assignee: Abbott Laboratories
    Inventors: Yuji Hori, Yoshiaki Nagano, Hiroshi Taniguchi
  • Patent number: 4250344
    Abstract: 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: Grant
    Filed: October 25, 1978
    Date of Patent: February 10, 1981
    Assignee: Chem Systems Inc.
    Inventors: Martin B. Sherwin, Jimmy Y. Peress, Kenneth J. Gwozdz
  • Patent number: 4236035
    Abstract: 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: Grant
    Filed: April 5, 1979
    Date of Patent: November 25, 1980
    Assignees: Societe Chimique des Charbonnages-CdF CHIMIE, Agence Nationale de Valorisation de la Recherche (ANVAR)
    Inventors: Pierre Sigwalt, Patrick Guyot, Michel Fontanille
  • Patent number: 4233467
    Abstract: .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: Grant
    Filed: March 12, 1979
    Date of Patent: November 11, 1980
    Assignee: The Dow Chemical Company
    Inventors: Junior J. Lamson, Richard H. Hall, Edward Stroiwas, Larry D. Yats
  • Patent number: 4210606
    Abstract: Cumene hydroperoxide is decomposed to phenol and acetone using a halogen-substituted thiophenol as the catalyst.
    Type: Grant
    Filed: June 15, 1979
    Date of Patent: July 1, 1980
    Assignee: Gulf Research and Development Company
    Inventors: Richard G. Austin, Wayne R. Pretzer, Thaddeus P. Kobylinski
  • Patent number: 4207424
    Abstract: 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: Grant
    Filed: August 9, 1978
    Date of Patent: June 10, 1980
    Assignee: Halcon Research & Development Corporation
    Inventor: Charles N. Winnick