Using Group Viii Metal-containing Catalyst With Additional Nonhydrocarbon Agent Patents (Class 585/269)
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Patent number: 5817900Abstract: The color of hydrocarbon resins having carbon-carbon double bonds and containing color bodies is lightened by a hydrotreating process consisting essentially of contacting the resin with hydrogen at a hydrogen pressure of 1 to about 20 bar (14.5 to about 290 psi) in the presence of a catalyst that promotes the hydrogenation of the color bodies without substantially changing the softening point or the content of carbon-carbon double bonds in the resin. The preferred catalyst is nickel/zinc oxide on SiO.sub.2.Type: GrantFiled: February 1, 1996Date of Patent: October 6, 1998Assignee: Hercules IncorporatedInventors: Erik Berrevoets, Jan van Drongelen
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Patent number: 5789637Abstract: The invention concerns a process for the hydrogenation of aromatic compounds contained in feeds with an initial boiling point of more than 100.degree. C. and which contain at least 10% by weight of aromatic compounds. It consists of introducing chlorine in a concentration of 0.5-500 ppm by weight with respect to the feed at a temperature of between 200.degree. C. and 450.degree. C., a pressure in the range 1 MPa to 25 MPa, an HSV of between 0.1 h.sup.-1 and 10 h.sup.-1 and a volume ratio of hydrogen to feed of 100-2000. The catalyst used is a noble metal type and contains less than 1% of at least one halogen. Preferably, the catalyst is fluorinated or chlorinated.Type: GrantFiled: June 27, 1996Date of Patent: August 4, 1998Assignee: Institut Francais du PetroleInventors: Samuel Mignard, Virginie France Harle, Slavik Kasztelan, Nathalie Marchal-George
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Patent number: 5777186Abstract: A process for selectively hydrogenating benzene in a hydrocarbon oil is disclosed. The process comprises reacting the hydrocarbon oil with hydrogen gas in the presence of a hydrogenation catalyst comprising at least one metal in Group VIII of the Periodic Table and an alkaline aqueous layer which contains zinc or a zinc compound. Benzene in hydrocarbon oils can be selectively converted into cyclohexane by the process, while suppressing the hydrogenation reaction of alkyl aromatic compounds which are important high octane materials for gasoline.Type: GrantFiled: October 6, 1997Date of Patent: July 7, 1998Assignees: Cosmo Research Institute, Cosmo Oil Co., Ltd.Inventor: Toshio Shimizu
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Patent number: 5689021Abstract: Halonitroaromatic compounds, e.g., 3-chloro-4-fluoronitrobenzene, are selectively hydrogenated into the corresponding haloaromatic amines, in the essential absence of hydrodehalogenation, by reacting same with hydrogen in the presence of a catalytically effective amount of a novel Raney-type catalyst composition consisting essentially of an alloy of nickel, aluminum and molybdenum, Ni/Al/Mo, the Al/Mo ratio by weight thereof being equal to or greater than 1.Type: GrantFiled: March 26, 1996Date of Patent: November 18, 1997Assignee: Rhone-Poulenc ChimieInventors: Georges Cordier, Jean-Pierre Damon, Pierre Fouilloux, Philippe Marion
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Patent number: 5668293Abstract: The invention concerns a process and catalyst for the production of cyclohexane by hydrogenation of benzene, comprising at least the two following steps: a) gradually introducing the feed of benzene for hydrogenation and a hydrogen-rich gas into a reaction zone containing a cyclohexane-rich liquid and a nickel-based catalyst in colloidal suspension and recovering a gaseous phase containing cyclohexane, hydrogen and benzene; b) introducing the gaseous phase into a reactor operating under hydrogenation conditions and containing at least one fixed bed of a solid nickel-based hydrogenation catalyst, wherein the nickel-based catalyst used in step a) is a product which results from the reduction, by at least one trialkylaluminium compound, of a solution of at least one nickel carboxylate and at least one sodium carboxylate in solution, the Ni:Na molar ratio being between 2:1 and 1000:1 in a hydrocarbon or a hydrocarbon mixture.Type: GrantFiled: February 16, 1995Date of Patent: September 16, 1997Assignee: Institut Francais du PetroleInventors: Alain Forestiere, Pierre Yout, Henri Delhomme
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Patent number: 5656761Abstract: A method for pretreating a slurry containing a ruthenium catalyst for use in the continuous partial hydrogenation of monocyclic aromatic hydrocarbons is disclosed. In this method, the above-mentioned slurry is heat-treated at a temperature of from 60.degree. to 180.degree. C. for at least 10 minutes while agitating. By using the pretreated catalyst slurry in the above-mentioned continuous partial hydrogenation, partial hydrogenation reaction products can be efficiently obtained without suffering from the excess mixing of the components of the catalyst slurry into an oil phase containing the partial hydrogenation reaction products, thereby enabling operations and facilities required for separation to be simplified.Type: GrantFiled: May 16, 1994Date of Patent: August 12, 1997Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Hajime Nagahara, Koji Nakagawa
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Patent number: 5650546Abstract: A process for the hydrogenation of organic compounds using water soluble catalyst in a biphasic media by: (A) forming an organo-water dispersion of (i) an organic phase having (a) an organic compound and (b) an organic solvent, and (ii) an aqueous phase having a water soluble group VIII metal catalyst composition and a water soluble ligand; and (B) contacting said dispersion with hydrogen to provide an interfacial reaction between said organic compound and said hydrogen, giving significant enhancement in the rate of reaction to produce saturated organic compound as compared to a reaction carried out in the absence of said water immiscible ligand.Type: GrantFiled: December 16, 1994Date of Patent: July 22, 1997Assignee: Council of Scientific Industrial Resear.Inventors: Raghunath Vitthal Chaudhari, Bhalchandra Mahadeo Bhanage, Sunil Sadashiv Divekar, Raj Madhukar Deshpande
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Patent number: 5648577Abstract: The present invention is directed toward a catalyst composition prepared by a process comprising: (a) impregnating an oxide precursor selected from the group consisting of rare earth oxide precursors, yttria precursors and mixtures thereof, onto an inorganic refractory oxide support; (b) drying said support at a temperature of about 100.degree. to about 120.degree. C. followed by calcining said support at a temperature of about 400.degree. to about 600.degree. C.; and (c) compositing or depositing on said support of step (b), a catalyst precursor salt represented by (ML)(Mo.sub.y W.sub.1-y O.sub.4).sub.a wherein M comprises Cr and/or one or more divalent promoter metals selected from the group consisting of Mn, Fe, Co, Ni, Cu, Zn and mixtures thereof, wherein y is any value ranging from 0 to 1, and wherein L is one or more neutral, nitrogen-containing ligands at least one of which is a chelating polydentate ligand; a=1 when chromium is not one of the promoter metals and 0.5.ltoreq.a.ltoreq.Type: GrantFiled: June 2, 1995Date of Patent: July 15, 1997Assignee: Exxon Research and Engineering CompanyInventors: Teh Chung Ho, Stuart Leon Soled, Sabato Miseo, Gary Brice McVicker, Michel Daage, Viktor Buchholz
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Patent number: 5639927Abstract: A process of producing cycloolefin, comprises the step of subjecting a monocyclic aromatic hydrocarbon to partial hydrogenation reaction in the presence of water and a ternary catalyst containing (a) ruthenium, (b) zinc and (c) at least one selected from the group consisting of gold, silver and copper.Type: GrantFiled: December 18, 1995Date of Patent: June 17, 1997Assignee: Mitsubishi Chemical CorporationInventors: Toshiyuki Suzuki, Tatsuya Ezaki
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Patent number: 5609752Abstract: There is provided a process for increasing the Cetane Index of a distillate fraction by reacting the fraction with hydrogen over a catalyst comprising a hydrogenation component, such as platinum, and zeolite Beta. The process results in the selective ring opening of cyclic compounds, such as aromatics, with a minimum of cracking of paraffinic hydrocarbons.Type: GrantFiled: December 12, 1995Date of Patent: March 11, 1997Assignee: Mobil Oil CorporationInventors: Kenneth J. Del Rossi, Gregory A. Jablonski, David O. Marler
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Patent number: 5589600Abstract: A process for the preparation of cyclohexene by partial hydrogenation of benzene with hydrogen in the presence of water and ruthenium catalysts modified with nickel, at elevated temperature in the liquid phase, wherein alloys of ruthenium with nickel are used as catalysts.Type: GrantFiled: May 25, 1995Date of Patent: December 31, 1996Assignee: BASF AktiengesellschaftInventors: Rolf Fischer, Roman Dostalek, Laszlo Marosi
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Patent number: 5569803Abstract: A method for producing a cycloolefin, which comprises partially hydrogenating a monocyclic aromatic hydrocarbon in the presence of water and a ruthenium catalyst supported on silica modified by zirconium oxide.Type: GrantFiled: December 23, 1994Date of Patent: October 29, 1996Assignee: Mitsubishi Chemical CorporationInventors: Takahiko Takewaki, Naoko Fujita, Toshiharu Yokoyama, Takao Maki
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Patent number: 5569802Abstract: The present invention relates to a catalyst for the selective hydrogenation of an unsaturated compound, based on a noble metal and/or a noble-metal oxide on an aluminum oxide support, and to a process for the preparation of the catalyst. The present invention further relates to a process for the selective hydrogenation of unsaturated compounds.Type: GrantFiled: September 28, 1994Date of Patent: October 29, 1996Assignee: Huels AktiengesellschaftInventors: Hans-Gerd L uken, Lothar Fischer, Wilhelm Droste, Bernd Nowitzki
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Patent number: 5504268Abstract: A process for the selective hydrogenation of aromatic acetylene compounds present as impurities in vinyl-aromatic compounds without substantial loss of vinyl-aromatic compound comprises adding hydrogen and an inert gas to a liquid phase vinyl-aromatic compound containing aromatic acetylene compounds and contacting the aromatic acetylene compound with hydrogen in the presence of a selective hydrogenation catalyst, wherein the partial hydrogen pressure is from about 0.001 to about 0.05 bar.Type: GrantFiled: April 8, 1994Date of Patent: April 2, 1996Assignee: The Dow Chemical CompanyInventors: Matheus J. M. van der Aalst, Fernando A. de Benito
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Patent number: 5482616Abstract: This invention relates to a catalyst for hydrogenation and/or dehydrogenation having an improved resistance against deactivation by sulfur compounds, comprising at least one hydrogenation component, at least one metal-oxide containing component and at least one component acting as a support material, in which at least a part of the hydrogenation component and a part of the metal-oxide containing component are present on said support material as separate particles, the particles of the hydrogenation component and the particles of the metal-oxide containing component being homogeneously distributed in the catalyst.Type: GrantFiled: May 26, 1992Date of Patent: January 9, 1996Assignee: Engelhard De Meern B. V.Inventors: Nilanjan Brahma, John W. Geus, Eugene G. M. Kuijpers
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Patent number: 5457251Abstract: Disclosed is a method for partially hydrogenating a monocyclic aromatic hydrocarbon to produce a cycloolefin, comprising reacting a monocyclic aromatic hydrocarbon with hydrogen in the presence of a particulate hydrogenation catalyst comprised mainly of metallic ruthenium, in a reaction system comprising a continuous aqueous phase having the particulate hydrogenation catalyst suspended therein, an oil phase containing the monocyclic aromatic hydrocarbon, and a gaseous phase comprising hydrogen gas, while applying a shearing force to the reaction system at a specific maximum shear rate. By the method of the present invention, not only can a cycloolefin be produced at high selectivity and in high yield, but also the catalytic activity can be stably maintained at a high level for a prolonged period of time.Type: GrantFiled: January 21, 1993Date of Patent: October 10, 1995Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Kunihiko Yamashita, Hideaki Obana, Issei Katsuta
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Patent number: 5457252Abstract: A novel catalyst has been provided for the selective hydrogenation of benzene in gasoline. The catalyst mixture comprises a water-soluble, organo-metallic, selective benzene hydrogenation catalyst comprising catalytically-active mixture of (A) M[L].sub.x [X].sub.y wherein M is a metal selected from the group consisting of Cr, Fe, Co, Ni, Mo, Ru, Rh, Pd, Ta, W, Re, Os, Ir, Pt, La and Ce; L is an aromatic hydrocarbon, e.g., benzene, diphenyl, etc., or a diaromatic hydrocarbon, e.g., naphthalene; X is a halogen; x is an integer from 1 to 10 inclusive; and y is an integer from 1 to 10 inclusive; and (B) tris(triphenylphosphine)rhodium(I)halide or tris(triphenylphosphine)ruthenium(I)halide. In use the process comprises admixing the gasoline with water. The above-identified water-soluble, organo-metallic selective benzene hydrogenation catalyst mixture is then added. A catalytic hydrogenation is then carried out in a hydrogenation zone at a temperature of about 150.degree. to about 245.degree. C.Type: GrantFiled: September 2, 1993Date of Patent: October 10, 1995Assignee: Her Majesty the Queen in right of Canada, as represented by the Minister of Energy, Mines & ResourcesInventors: Udai S. Gill, Craig W. Fairbridge, Brian A. Farnand, Esteban C. Castellanos
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Patent number: 5451312Abstract: This invention provides a process for producing a distillate boiling-range hydrocarbon product which comprises hydrotreating a hydrodesulfurized aromatic, substantially dealkylated hydrocarbon feed produced by the catalytic cracking of a hydrocarbon fraction, the feed having an initial boiling point of at least 300.degree. F., an aromatic content of at least about 30 weight percent, a hydrogen content not more than about 12 weight percent and a sulfur content of not more than 5000 ppmw, in the presence of a catalyst comprising an inorganic, non-layered, porous, crystalline phase material having pores with diameters of at least about 13 .ANG. and exhibiting, after calcination, an X-ray diffraction pattern with at least one peak with a relative intensity of 100 at a d-spacing greater than about 18 .ANG.Type: GrantFiled: October 26, 1993Date of Patent: September 19, 1995Assignee: Mobil Oil CorporationInventors: Minas R. Apelian, Thomas F. Degnan, Stuart S. Shih
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Patent number: 5435907Abstract: A naphtha or a middle distillate hydrocarbon is dehydroaromatized by hydrotreating in the presence of a catalyst containing non-noble Group VIII metal and Group VI-B metal on carbon.Type: GrantFiled: January 31, 1994Date of Patent: July 25, 1995Assignee: Texaco Inc.Inventors: Chakka Sudhakar, Frank Dolfinger, Jr., Dennis J. Pao, John Hazen
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Patent number: 5414171Abstract: This is a catalyst and a process for partially hydrogenating polycyclic and monocyclic aromatic hydrocarbons such as benzene, naphthalenes, biphenyls, and alkylbenzenes to produce the corresponding cycloolefins. The catalyst is a hydrogenation catalyst comprising ruthenium and a promoter metal, such as cobalt, on a composite support. It is a process in which the product cycloolefin is produced in high yield and with high selectivity.Type: GrantFiled: February 26, 1992Date of Patent: May 9, 1995Assignee: Catalytica, Inc.Inventors: Michael A. Richard, Jacques C. De Deken, David K. Yee
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Patent number: 5350504Abstract: Non-acidic tin-, lead-, or indium-modified Pt/ZSM-5 catalysts are effective catalysts for the shape selective preferential hydrogenation of certain aromatic hydrocarbons in admixture with others. These catalysts can be used to reduce the aromatic content of gasoline and distillates.Type: GrantFiled: December 18, 1992Date of Patent: September 27, 1994Assignee: Mobil Oil CorporationInventor: Ralph M. Dessau
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Patent number: 5321139Abstract: Two processes are described for the preparation of the optically pure compounds of formula 1: ##STR1## in which R.sup.1 and R.sup.2 are e.g. alkyl, R.sup.3 and R.sup.4 are e.g. hydrogen and R.sup.5 is e.g. hydrogen. Both processes include, as key steps, the enantioselective hydrogenation of a C.dbd.C double bond and the regioselective formation of a dicarboxylic acid monoamide derivative. In one process a phenylitaconic acid derivative is asymmetrically hydrogenated to give an optically active (R)-benzylsuccinic acid which is then converted to a diester, said diester being converted to the monoamide compound of formula 1. In the second process, a phenylitaconic acid derivative is converted to its anhydride, and the anhydride is then converted to a monoamide which is then asymmetrically hydrogenated to give the compound of formula 1.Type: GrantFiled: February 16, 1993Date of Patent: June 14, 1994Assignee: Hoechst AktiengesellschaftInventors: Ulrich Lerch, Heiner Jendralla, Bernhard Seuring, Rainer Henning
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Patent number: 5306853Abstract: Compounds of formula II ##STR1## wherein the groups (R.sub.1).sub.2 P(CH.sub.2).sub.m bzw.n are in o- or m-position to each other and the substituents R.sub.1 are identical or different radicals, m and n are each independently of the other 0 or 1, R.sub.1 is linear or branched C.sub.1 -C.sub.12 alkyl, unsubstituted C.sub.5 -C.sub.6 cycloalkyl or C.sub.5 -C.sub.6 cycloalkyl which is substituted by C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy, or is phenyl or benzyl, or both substituents R.sub.1 in a group (R.sub.1).sub.2 P together are o,o'-diphenylene, --R.sub.2 --X-- is a bond or --(C.sub.x H.sub.2x --O).sub.y --, or X-- is O-- and R.sub.2 is C.sub.1 -C.sub.6 alkylene, x is an integer from 2 to 6 and y is an integer from 2 to 6, R.sub.3 is C.sub.2 -C.sub.18 alkylene, phenylene or benzylene, and R.sub.4 is C.sub.1 -C.sub.6 alkyl or phenyl, can be applied to solid carriers, such as silica gel or aerosils, and complexed with rhodium or iridium compounds.Type: GrantFiled: June 17, 1993Date of Patent: April 26, 1994Assignee: Ciba-Geigy CorporationInventors: Benoit Pugin, Manfred Muller, Felix Spindler
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Patent number: 5264641Abstract: There is provided a method for hydrogenating aromatics with a catalyst comprising a crystalline ultra-large pore oxide material. The catalyst also comprises a hydrogenation metal, such as palladium. The process may be used to saturate benzene to form cyclohexane.Type: GrantFiled: December 14, 1992Date of Patent: November 23, 1993Assignee: Mobil Oil Corp.Inventors: William S. Borghard, Cynthia T. Chu, Thomas F. Degnan, Stuart S. Shih
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Patent number: 5254714Abstract: A process is disclosed for the enantioselective hydrogenation of olefins of the formula: ##STR1## where R is hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, Z is ##STR2## where R' is hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl, --CN, C(NH)OR" where R" is C.sub.1 to C.sub.6 linear or branched alkyl, or --C(O)NH.sub.2 ; and Ar is phenyl or naphthyl unsubstituted or substituted with benzoyl or substituted benzoyl, C.sub.1 to C.sub.6 linear or branched alkyl, C.sub.1 to C.sub.6 linear or branched alkoxy, halo, or carboxylic acid or C.sub.1 to C.sub.6 linear or branched alkyl ester thereof, which comprises contacting said aromatic-substituted olefin with a catalytically effective amount of a ruthenium phosphite complex.Type: GrantFiled: October 10, 1991Date of Patent: October 19, 1993Assignee: Ethyl CorporationInventor: Merrikh Ramezanian
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Patent number: 5254763Abstract: A novel process is provided for the selective hydrogenation of benzene in a solution of gasoline and other aromatic organic compounds. The process includes the steps of carrying out the catalytic hydrogenation in a hydrogenation zone at a temperature of about 45.degree. to about 250.degree. C. at a pressure of about 200 psi to about 500 psi in a biphasic system of aqueous and organic liquids the hydrogenation catalyst being water-soluble. The organic liquid is removed from the hydrogenation zone. At least a catalytic amount of the catalyst is retained in the hydrogenation zone. The catalyst above described is also a facet of this invention.Type: GrantFiled: December 2, 1991Date of Patent: October 19, 1993Inventors: Udai S. Gill, Craig W. Fairbridge, Brian A. Farnand
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Patent number: 5210333Abstract: A method for the separation of benzene from a hydrocarbon stream, such as a gasoline boiling range stream, which comprises contacting the hydrocarbon stream with an adsorbent capable of selectively adsorbing the benzene from the stream, hydrogenating the adsorbed benzene to cyclohexane, and desorbing the cyclohexane from the adsorbent. The hydrogenation of the benzene to cyclohexane facilitates the removal of the benzene from the adsorbent.Type: GrantFiled: September 30, 1992Date of Patent: May 11, 1993Assignee: Exxon Research and Engineering CompanyInventors: Richard J. Bellows, Gary B. McVicker, Joseph E. Baumgartner, James P. Dennis
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Patent number: 5210348Abstract: A substantially benzene-free product suitable for gasoline blending is formed from a benzene-containing refinery stream. At least about 30% of the benzene initially present in the stream is catalytically alkylated with C.sub.2 -C.sub.4 olefins to form alkylated products. Most preferably, the alkylation zone is present in the distillation column and the alkylated products drop to the lower portion of the column and are recovered with the heavy fraction. Alternatively, the alkylation zone is downstream of the distillation column and a secondary distillation column removes the heavier alkylated products. The remaining light fraction is hydrogenated to convert substantially all of the remaining non-alkylated benzene to cyclohexane and is isomerized to boost the octane of C.sub.5 -C.sub.7 paraffins, preferably in a single reactor.Type: GrantFiled: May 23, 1991Date of Patent: May 11, 1993Assignee: Chevron Research and Technology CompanyInventors: C. Richard Hsieh, Richard C. Robinson
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Patent number: 5189233Abstract: Disclosed is an improvement in a process for production of cyclohexane by liquid phase hydrogenation of benzene wherein no diluent is necessary, which comprises contacting benzene and hydrogen in the presence of a mixed catalyst bed comprising a first catalyst which is a less active hydrogenation catalyst selected from elements of Group VIII of the Periodic Table and a second, more active catalyst, comprising a Group VIII metal supported on an oxide, such as, for example, alumina, silica or titania at a temperature of about 40.degree. C. to about 300.degree. C. and pressure sufficient to keep the benzene liquid at the chosen reaction temperature.Type: GrantFiled: August 23, 1991Date of Patent: February 23, 1993Assignee: Texaco Chemical CompanyInventors: John M. Larkin, James H. Templeton, Donald H. Champion
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Patent number: 5183926Abstract: Aromatic dicarboxylic acids of the formula ##STR1## in which R.sup.1, R.sup.2, m, n, and X have the meaning mentioned in the description,can be prepared from the bisphenols, on which they are based, of the formula ##STR2## if the bisphenols are first reacted to give the bissulphonates, the sulphonate groups are removed catalytically with H.sub.2 and the hydrocarbons obtained in this way are doubly acylated in a known manner and the acyl groups are oxidized to the carboxyl groups.Many of the aromatic dicarboxylic acids which can be prepared in this way are new.Type: GrantFiled: September 13, 1991Date of Patent: February 2, 1993Assignee: Bayer AktiengesellschaftInventors: Richard Weider, Thomas Scholl
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Patent number: 5171910Abstract: The present invention provides a catalyst for hydrogenation of aromatic compounds, which comprises a hydrophilic support material; and a stationary aqueous acid phase supported by the hydrophilic support material, the aqueous acid having a transition metal catalyst dissolved therein, Preferably, the solid hydrophilic support material is an acidic material, such as an acid-treated clay.The foregoing catalyst is particularly useful in hydrogenating aromatic hydrocarbons.Type: GrantFiled: October 11, 1991Date of Patent: December 15, 1992Assignee: Exxon Research and Engineering CompanyInventors: Istvan T. Horvath, Raymond A. Cook
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Patent number: 5171911Abstract: The present invention relates to ceramic materials containing a homogeneous dispersion of metal particles, particularly sol-gel ceramic materials, a method of preparing the same, and processes for hydrogenating and oxidizing organic compounds using the same.Type: GrantFiled: May 15, 1991Date of Patent: December 15, 1992Assignee: University of South CarolinaInventors: James M. Tour, Shekar L. Pendalwar, Joel P. Cooper
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Patent number: 5157179Abstract: A method for producing a cycloolefin which comprises partially hydrogenating an aromatic hydrocarbon with hydrogen in a liquid phase in the presence of water and a catalyst having as main component ruthenium supported on a carrier, to form the corresponding cycloolefin, wherein an oxide with the total pore volume of pores having radii of from 20 to 100,000 .ANG. being from 0.3 to 10 cc/g and with the volume of pores having radii of from 20 to 200 .ANG. constituting at most 15% of the total pore volume, is used as the carrier for the catalyst.Type: GrantFiled: July 5, 1991Date of Patent: October 20, 1992Assignee: Mitsubishi Kasei CorporationInventors: Tohru Setoyama, Takahiko Takewaki, Takao Maki
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Patent number: 5146024Abstract: A process for converting aromatic hydrocarbons (in particular benzene) to cycloalkyl-substituted aromatic hydrocarbons (in particular cyclohexylbenzene) in the presence of free hydrogen and a palladium-promoted zeolite catalyst is carried out in the presence of carbon monoxide as process modifier (so as to enhance the selectivity to the cycloalkyl-substituted aromatic hydrocarbon).Type: GrantFiled: May 20, 1991Date of Patent: September 8, 1992Assignee: Phillips Petroleum CompanyInventor: Larry E. Reed
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Patent number: 5057206Abstract: A white oil product is produced by hydrogenating a hydrocarbon stream produced from an aromatic alkylation process. The hydrogenation occurs at hydrogenation conditions in the presence of a catalyst comprising a platinum group metal component surface impregnated on a refractory oxide catalyst support. The platinum group metal component is surface impregnated such that the platinum group metal is essentially all located with a 100 micron layer of the surface of the catalyst support.Type: GrantFiled: August 25, 1988Date of Patent: October 15, 1991Assignee: UOPInventors: Dusan J. Engel, Bipin V. Vora
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Patent number: 5030780Abstract: A catalyst typically containing nickel and tungsten on a support containing (a) a dispersion of silica-alumina in an alumina matrix and (b) an ultra-hydrophobic zeolite is utilized for converting relatively low boiling hydrocarbon-containing feedstocks. The catalyst is particularly effective for promoting aromatic saturation reactions, particularly in diesel fuel feedstocks.Type: GrantFiled: July 26, 1990Date of Patent: July 9, 1991Assignee: Union Oil Company of CaliforniaInventors: John W. Ward, Dennis D. Delaney
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Patent number: 5030779Abstract: A hydrogenation catalyst prepared by combining one or more Group VIII metal compounds with one or more alkylalumoxanes and one or more alkyls or hydrides of a metal selected from the group consisting of the Group Ia, IIa, and IIa metals and a hyrogenation process wherein said catalyst is used to hydrogenate compounds containing ethylenic and/or aromatic unsaturation. Preferably, the one or more Group VIII metal compounds will be contacted sequentially with the one or more alkylalumoxanes and the one or more alkyls or hydrides, first with the one or more alkylalumoxanes and then with one or more alkyls and/or hydrides. The one or more Group VIII metal compounds is selected from the group of compounds consisting of carboxylates, chelates, alkoxides, salts of acids containing sulfur, salts of partial esters of acids containing sulfur and salts of aliphatic and aromatic sulfonic acids. Nickel and cobalt compounds are preferred for use in the hydrogenation catalysts.Type: GrantFiled: August 29, 1990Date of Patent: July 9, 1991Assignee: Shell Oil CompanyInventors: Ronald J. Hoxmeier, Lynn H. Slaugh
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Patent number: 4980331Abstract: A hydrogenation catalyst prepared by combining one or more Group VIII metal compounds with one or more alkylalumoxanes and one or more alkyls or hydrides of a metal selected from the group consisting of the Group Ia, IIa, and IIa metals and a hydrogenation process wherein said catalyst is used to hydrogenate compounds containing ethylenic and/or aromatic unsaturation. Preferably, the one or more Group VIII metal compounds will be contacted sequentially with the one or more alkylalumoxanes and the one or more alkyls or hydrides, first with the one or more alkylalumoxanes and then with the one or more alkyls and/or hydrides. The one or more Group VIII metal compounds is selected from the group of compounds consisting of carboxylates, chelates, alkoxides, salts of acids containing sulfur, salts of partial esters of acids containing sulfur and salts of aliphatic and aromatic sulfonic acids. Nickel and cobalt compounds are preferred for use in the hydrogenation catalysts.Type: GrantFiled: June 8, 1989Date of Patent: December 25, 1990Assignee: Shell Oil CompanyInventors: Ronald J. Hoxmeier, Lynn H. Slaugh
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Patent number: 4950386Abstract: It has now been discovered that hydrocarbon feeds containing a polycyclic aromatic compound or mixtures thereof can be selectively hydrogenated by contacting the feed with a transition metal catalyst and hydrogen in the presence of an acid to provide a hydrocarbon mixture in which the aromatic content consists substantially of mono- and di-aromatic compounds. Useful acids include Lewis acids and acids having a pKa in the range of 0 to about -10.Type: GrantFiled: August 15, 1988Date of Patent: August 21, 1990Assignee: Exxon Research and Engineering CompanyInventor: Manuel A. Francisco
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Patent number: 4861930Abstract: A combination process for the conversion of C.sub.2 -C.sub.6 aliphatic hydrocarbons into easily transportable hydrocarbons of greater molecular weight. The combination process comprises converting the C.sub.2 -C.sub.6 aliphatic hydrocarbons to aromatic hydrocarbons in a dehydrocyclodimerization reaction zone after which the aromatic is directly hydrogenated in the presence of hydrogen from the dehydrocyclodimerization reaction step to produce large transportable aliphatic hydrocarbons. It is also an aspect of the invention that the hot hydrogenation reaction zone product stream is used to preheat the feed stream to the dehydrocyclodimerization reaction zone.Type: GrantFiled: September 28, 1988Date of Patent: August 29, 1989Assignee: UOPInventors: Paul R. Cottrell, Thomas R. Fritsch, Christopher D. Gosling
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Patent number: 4849093Abstract: In the catalytic processing of aromatic hydrocarbon compounds, a hydrocarbon oil is successively contacted at aromatic saturation conditions with a catalyst in a first reaction zone and contacted at a lower temperature with a second portion of the catalyst in the same reactor or in multiple reactors.Type: GrantFiled: February 2, 1987Date of Patent: July 18, 1989Assignee: Union Oil Company of CaliforniaInventors: Dennis A. Vauk, Milan Skripek
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Patent number: 4840745Abstract: A stable fluid composition is provided by this invention which contains a cis-o-tercyclohexyl compound and a trans-o-tercyclohexyl compound at a weight ratio of 25:75-65:35. This composition is useful as a fluid for traction drive.Type: GrantFiled: November 20, 1987Date of Patent: June 20, 1989Assignee: Idemitsu Kosan Company LimitedInventors: Toshiyuki Tsubouchi, Kazuaki Abe, Hitoshi Hata
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Patent number: 4804796Abstract: Improved, heterogeneous, refractory catalysts are in the form of gas-impervious, hollow, thin-walled spheres (10) suitable formed of a shell (12) of refractory such as alumina having a cavity (14) containing a gas at a pressure greater than atmospheric pressure. The wall material may be itself catalytic or a catalytically active material coated onto the sphere as a layer (16), suitably platinum or iron, which may be further coated with a layer (18) of activator or promoter. The density of the spheres (30) can be uniformly controlled to a preselected value within .+-.10 percent of the density of the fluid reactant such that the spheres either remain suspended or slowly fall or rise through the liquid reactant.Type: GrantFiled: April 8, 1987Date of Patent: February 14, 1989Assignee: California Institute of TechnologyInventors: Taylor G. Wang, Daniel D. Elleman, Mark C. Lee, James M. Kendall, Jr.
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Patent number: 4795840Abstract: The present invention provides a method for preparing a hydrocarbon mixture solvent comprising 1 to 15 wt % of alkyl tetralins and 0 to 10 wt % of aromatic hydrocarbons and having a boiling point of 160.degree. to 300.degree. C., the solvent being substantially free from naphthalene and biphenyl; the method being characterized by comprising the steps of subjecting a kerosene fraction having a boiling point of 150.degree. to 300.degree. C. to a nucleus hydrogenation treatment at a temperature of 100.degree. to 300.degree. C. at a pressure of 30 to 100 kg/cm.sup.2 in the presence of a metallic catalyst for nucleus hydrogenation of aromatic nuclei; separating and removing at least a part of n-paraffins in the kerosene therefrom by the use of a molecular sieve made from a synthesized zeolite having pores of 5 .ANG. in diameter in order to obtain a residual oil; and subjecting the latter to a rectification.Type: GrantFiled: July 2, 1987Date of Patent: January 3, 1989Assignee: Nippon Petrochemicals Co., Ltd.Inventors: Michiaki Torii, Seiji Hirooka
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Patent number: 4792625Abstract: The invention provides a process for reducing substantially water insoluble organic compounds containing reducible groups comprising contacting these compounds with an aqueous solution of a formic acid salt in the presence of a hydrogenation catalyst and in the substantial absence of a phase transfer catalyst.Type: GrantFiled: July 9, 1987Date of Patent: December 20, 1988Assignee: Yissum Research Development CompanyInventors: Harold Wiener, Shmuel Vandel, Yoel Sasson
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Patent number: 4783565Abstract: A cis-isomer of perhydroacenaphthene is selectively prepared through hydrogenation of acenaphthene by effecting hydrogenation of 80.degree. to 200.degree. C. in the presence of a Ru and/or Rh based catalyst. A cis-isomer having the highest boiling point is obtained as a major product.Type: GrantFiled: May 4, 1987Date of Patent: November 8, 1988Assignee: Kawasaki Steel CorporationInventors: Yoshihiro Naruse, Toshihide Suzuki
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Patent number: 4751335Abstract: A process for preparing a fluid for traction drive from a fraction containing compounds having at least four aromatic rings is disclosed. The fraction is a by-product produced at the time of the preparation of alpha-methyl-benzylalkylbenzenes by alkylation of at least one compound selected from C.sub.7 -C.sub.10 alkylbenzenes with styrene in the presence of an acid catalyst. The process comprises the steps of decomposing the fraction in an atmosphere of hydrogen at a predetermined temperature and pressure, collecting a decomposition product having a boiling range not higher than 450.degree. C. and then subjecting the decomposition product to nuclear hydrogenation at aromatic rings thereof in the presence of a catalyst capable of nuclear hydrogenation.Type: GrantFiled: February 2, 1987Date of Patent: June 14, 1988Assignee: Nippon Oil Co., Ltd.Inventors: Junichi Kubo, Kenji Suzuki, Kozo Kamiya, Eiji Akiyama, Masao Nambu
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Patent number: 4734536Abstract: A process for producing a cycloolefin in high selectivity and yield by partial hydrogenation of a monocyclic armoatic hydrocarbon with hydrogen is disclosed. In this process, the hydrogenation reaction is carried out under a neutral or acidic condition in the presence of:(i) a particulate hydrogenating catalyst mainly comprising metallic ruthenium having an average crystallite size of 200 .ANG. or less,(ii) at least one zinc compound as a promoter,(iii) at least one additive selected from the group consisting of oxides, hydroxides and hydrates thereof Zr, Hf, Ti, Nb, Ta, Cr, Fe, Co, Al, Ga and Si, and(iv) water.Type: GrantFiled: October 2, 1986Date of Patent: March 29, 1988Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Hajime Nagahara, Mitsuo Konishi
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Patent number: 4678861Abstract: A process for producing a cycloolefin which comprises partially hydrogenating a monocyclic aromatic hydrocarbon in the presence of a ruthenium catalyst composed of a rare earth element compound solid carrier and a ruthenium component supported thereon. The resulting cycloolefin is obtained in high yield and high selectivity and the catalyst can be repeatedly used for a prolonged period of time.Type: GrantFiled: October 23, 1985Date of Patent: July 7, 1987Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Osamu Mitsui, Yohei Fukuoka
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Patent number: 4610779Abstract: A process for the hydrogenation of aromatic hydrocarbons contained in hydrocarbonaceous oil feed comprising at least about 15 wppm organic nitrogen compounds is provided in which the feed is contacted with hydrogen in a substantially sulfur-free environment in the presence of a catalyst comprising a Group VIII noble metal component, such as palladium, a Y-type crystalline aluminosilicate zeolite and a support such as alumina. When the hydrogenation activity of the catalyst decreases, the partially deactivated catalyst is stripped with hydrogen periodically to increase the hydrogenation activity of the catalyst.Type: GrantFiled: October 5, 1984Date of Patent: September 9, 1986Assignee: Exxon Research and Engineering Co.Inventors: Gerald E. Markley, James C. Spry, Jr.