Using Group Viii Metal-containing Catalyst With Additional Nonhydrocarbon Agent Patents (Class 585/269)
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Patent number: 4605490Abstract: A noble metal-containing zeolitic catalyst having cracking activity and hydrogenation activity is pretreated by contacting the catalyst with a nitrogen-containing compound to decrease the cracking activity of the catalyst followed by treatment with hydrogen to recover the hydrogenation activity of the catalyst. The pretreated catalyst is used in a process for the hydrogenation of aromatic hydrocarbons.Type: GrantFiled: October 5, 1984Date of Patent: August 12, 1986Assignee: Exxon Research and Engineering Co.Inventors: George J. Balinsky, Omer Biceroglu, Joe S. Lin
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Patent number: 4604492Abstract: The invention provides a novel class of compounds dicyclohexylcyclopentanes or, in particular, 1,3-dicyclohexyl-1-methyl cyclopentane which is synthesized by the hydrogenation of 1-methyl-1,3-diphenyl cyclopentane which in turn is obtained by the dimerization reaction of .alpha.-methylstyrene in the presence of metallic sodium as the catalyst. The compound is useful as a fluid for traction drive.Type: GrantFiled: October 8, 1985Date of Patent: August 5, 1986Assignee: Idemitsu Kosan Company LimitedInventors: Nobuaki Shimizu, Toshiyuki Tsubouchi, Hitoshi Hata
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Patent number: 4604493Abstract: The invention provides a novel compound 1-cyclohexyl-1,4-dimethyl decahydronaphthalene which is useful as fluids for traction drive. The compound can be synthesized by the hydrogenation of 1,4-dimethyl-4-phenyl-1,2,3,4-tetrahydronaphthalene and analytical results for the identification of the compound are given.Type: GrantFiled: October 8, 1985Date of Patent: August 5, 1986Assignee: Idemitsu Kosan Company LimitedInventors: Nobuaki Shimizu, Toshiyuki Tsubouchi, Hitoshi Hata
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Patent number: 4532351Abstract: Supported catalysts comprised of one or more metals of Group VIII, optionally one or more metals from Group IB and IIA, aluminum and silicate are used for hydrogenating hydrogenatable organic compounds. The catalysts can be produced by coprecipitating metal ions from Group VIII, optionally metal ions from Groups IB and IIA, aluminum ions, and silicate ions, in the presence of solid porous particles.Type: GrantFiled: June 16, 1982Date of Patent: July 30, 1985Assignee: Exxon Research and Engineering Co.Inventors: Allan E. Barnett, Albert P. Halluin
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Patent number: 4532227Abstract: Low ash pelleted carbon is prepared by contacting pelleted carbon first with hydrochloric acid followed by leaching with hydrofluoric acid.Type: GrantFiled: December 22, 1980Date of Patent: July 30, 1985Assignee: Texaco Development CorporationInventor: Robert M. Suggitt
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Patent number: 4517390Abstract: A catalytic process for hydrogenation of unsaturated organic compounds is carried out in a two-phase aqueous/organic medium, in which the catalytic complex is dissolved in the aqueous phase and to which is added an amphiphilic reagent to facilitate phase boundary crossing of dissolved species. Catalyst separation from reaction products is thereby rendered more efficient.The catalytic complex is preferably formed in situ and contains a water-soluble phosphine ligand, preferably a hydroxy- or carboxy-aryl phosphine.Type: GrantFiled: February 21, 1984Date of Patent: May 14, 1985Assignee: Johnson Matthey Public Limited CompanyInventors: Michael J. H. Russell, Barry A. Murrer
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Patent number: 4508918Abstract: Cyclohexane derivatives such as cyclohexanol and cyclohexyl carboxylates are produced directly from aromatic hydrocarbons. The reaction may be carried out, under hydrogenation conditions, by reacting an aromatic hydrocarbon with hydrogen and a reagent selected from the group consisting of water, and carboxylic acids in the presence of a strong acid and a hydrogenation catalyst.Type: GrantFiled: November 20, 1979Date of Patent: April 2, 1985Assignee: Toray Industries, Inc.Inventors: Yutaka Yasuhara, Masaki Nishino, Seikichi Matsuhisa
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Patent number: 4506030Abstract: A novel transition metal catalyst which has a phosphido-type linkage is much less subject to metal loss during operations because of its greater bond strength. This catalyst will hydrogenate unsaturated hydrocarbons under milder conditions than most prior art catalysts.Type: GrantFiled: February 17, 1984Date of Patent: March 19, 1985Assignee: The Board of Regents, University of Texas SystemInventor: Richard A. Jones
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Patent number: 4495089Abstract: A continuous process for the production of a solvent for use in the liquefaction of coal is described. The process comprises hydrogenating a mixture of 100 parts by weight of a hydrocarbon mixture and from 0.2 to 10 parts by weight of phenol and/or alkylphenol. The hydrocarbon mixture contains at least 50% by weight of a polycyclic (from tricyclic to pentacyclic) aromatic hydrocarbon or its alkyl derivative. The hydrocarbon mixture is distilled away in a proportion of at least 80% when heated at a temperature of from 320.degree. to 550.degree. C. The hydrogenation of the hydrocarbon mixture and phenol and/or alkylphenol may be carried out with or without the addition of from 0.05 to 0.Type: GrantFiled: September 10, 1982Date of Patent: January 22, 1985Assignee: Mitsubishi Oil Company, LimitedInventors: Hiroyuki Ihara, Kazuo Takahashi, Michiro Matsubara, Fumio Kumata, Yoshitomo Sanami
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Patent number: 4495373Abstract: The invention provides an improvement in the partial nuclear hydrogenation of an aromatic hydrocarbon compound in the liquid phase with admixture of water catalyzed by a ruthenium-containing solid catalyst. The scope of the invention is in the use of a novel ruthenium-containing catalyst supported on a silica gel and the like carrier and the catalyst is prepared by the hydrolysis and gelation of an alkoxide of silicon or aluminum in a solution containing a ruthenium compound, e.g. ruthenium alkoxide, followed by drying of the gelled material so that the resultant catalyst is very uniformly impregnated with the ruthenium ingredient to be imparted with greatly improved catalytis activity and selectivity for the intended reaction over conventional ruthenium-containing catalysts prepared by post-impregnation of a preformed silica gel carrier.Type: GrantFiled: February 22, 1984Date of Patent: January 22, 1985Assignee: Director-General of the Agency of Industrial Science and TechnologyInventors: Shuichi Niwa, Juichi Imamura, Fujio Mizukami, Kazuo Shimizu, Yoshio Orito
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Patent number: 4482641Abstract: A high surface area, porous active carbon matrix containing a substantially uniform dispersion of a metal or metal-containing material and a method for making the same are disclosed.Type: GrantFiled: February 28, 1983Date of Patent: November 13, 1984Assignee: Standard Oil Company (Indiana)Inventor: Arnold N. Wennerberg
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Patent number: 4469590Abstract: A process for the hydrogenation of aromatic hydrocarbons contained in a hydrocarbonaceous oil feed 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, deposited on a steamed support such as steamed tungsten oxide composited with alumina.Type: GrantFiled: June 17, 1983Date of Patent: September 4, 1984Assignee: Exxon Research and Engineering Co.Inventors: Robert C. Schucker, Kenneth S. Wheelock
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Patent number: 4431836Abstract: Group VIII metals immobilized on an aminated polysaccharide in a highly dispersed state are active catalysts in the hydrogenation of unsaturated organic materials. Chitin and chitosan are preferred supports, with platinum and palladium among the more active Group VIII metals in hydrogenation.Type: GrantFiled: September 28, 1982Date of Patent: February 14, 1984Assignee: UOP Inc.Inventor: Blaise J. Arena
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Patent number: 4420648Abstract: Supported coprecipitated cobalt-silica hydrogenation catalysts are disclosed. The catalysts are prepared by: preparing an aqueous reaction mixture containing cobalt cations, silicate anions and solid porous carrier particles under agitation to form a coprecipitate of the cobalt and silicate ions onto said solid porous support particles; heating the aqueous reaction mixture; and adding an alkaline precipitating agent to further precipitate the cobalt and silicate ions onto said solid porous carrier particles. The aqueous reaction mixture may additionally include copper cations.Type: GrantFiled: September 19, 1979Date of Patent: December 13, 1983Assignee: Exxon Research and Engineering Co.Inventors: James L. Carter, Allan E. Barnett
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Patent number: 4413118Abstract: Organic sulfur compounds containing a carbon-sulfur double bond are used to remove homogeneous catalyst group VIII metals from chemical process streams.Type: GrantFiled: March 2, 1981Date of Patent: November 1, 1983Assignee: Merck & Co., Inc.Inventors: F. Edward Roberts, Victor J. Grenda
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Patent number: 4396540Abstract: Dehydrogenatable hydrocarbons are dehydrogenated by contacting them at hydrocarbon dehydrogenation conditions with a multimetallic catalytic composite comprising a combination of a catalytically effective amount of a pyrolyzed ruthenium carbonyl component with a porous carrier material containing a uniform dispersion of catalytically effective amounts of a platinum group component maintained in the elemental metallic state, and of a rhenium component. An optional non-acidic multimetallic catalytic composite disclosed herein is a combination of a catalytically effective amount of a pyrolyzed ruthenium carbonyl component with a porous carrier material containing a uniform dispersion of catalytically effective amounts of a platinum group component which is maintained in the elemental metallic state during the incorporation of the ruthenium carbonyl component, a rhenium component, and an alkali or alkaline earth component.Type: GrantFiled: September 11, 1983Date of Patent: August 2, 1983Assignee: UOP Inc.Inventor: George J. Antos
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Patent number: 4392001Abstract: The invention relates to a process for the preparation of a cycloalkene through partial hydrogenation of the corresponding aromatic hydrocarbon in the gas phase in the presence of a ruthenium catalyst. This hydrogenation process is carried out in the presence of water vapor.Type: GrantFiled: December 30, 1981Date of Patent: July 5, 1983Assignee: Stamicarbon, B.V.Inventors: Johannes A. Don, Joseph J. F. Scholten
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Patent number: 4379027Abstract: This invention provides a process for obtaining m-methylstyrene from a mixture with p-methylstyrene that comprises hydrogenating a mixture of p-methylstyrene and m-methylstyrene in the presence of a zeolite having a Constraint Index of about 1 to about 12, a silica to alumina mole ratio of at least about 12, and a dried crystal density of not less than about 1.6 grams per cubic centimeter, modified with at least one element of Group IA, IIA, IVB, or VB of the Periodic Chart of the Elements and a metal of Group VIII of the Periodic Chart of the Elements; thereby obtaining a mixture of m-methylstyrene and p-ethyltoluene, and removing p-ethyltoluene by distillation.Type: GrantFiled: December 24, 1981Date of Patent: April 5, 1983Assignee: Mobil Oil CorporationInventors: John M. Klosek, Margaret M. Wu
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Patent number: 4367137Abstract: Hydrocarbons are converted by contacting them at hydrocarbon conversion conditions with an acidic multimetallic catalytic composite comprising a combination of catalytically effective amounts of a platinum group component, a cobalt component, a tin component, a phosphorus component and a halogen component with a porous carrier material. The platinum group, cobalt, tin, phosphorus and halogen components are present in the multimetallic catalyst in amounts respectively, calculated on an elemental basis, corresponding to about 0.01 to about 2 wt. % platinum group metal, about 0.05 to about 5 wt. % cobalt, about 0.01 to about 5 wt. % tin, about 0.01 to about 5 wt. % phosphorus and about 0.1 to about 3.5 wt. % halogen. A specific example of the type of hydrocarbon conversion process disclosed is a process for the catalytic reforming of a low-octane gasoline fraction wherein the gasoline fraction and a hydrogen stream are contacted with the acidic multimetallic catalyst disclosed herein at reforming conditions.Type: GrantFiled: November 23, 1981Date of Patent: January 4, 1983Assignee: UOP Inc.Inventors: George J. Antos, Tai-Hsiang Chao
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Patent number: 4367355Abstract: Group VIII metals immobilized on an aminated polysaccharide in a highly dispersed state are active catalysts in the hydrogenation of unsaturated organic materials. Chitin and chitosan are preferred supports, with platinum and palladium among the more active Group VIII metals in hydrogenation.Type: GrantFiled: February 23, 1981Date of Patent: January 4, 1983Assignee: UOP Inc.Inventor: Blaise J. Arena
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Patent number: 4313018Abstract: Anthranilic acid has been anchored to polystyrene, and rhodium, palladium, platinum and ruthenium complexes of this modified polystyrene have been prepared. These catalysts will reduce a variety of olefinic and aromatic hydrocarbons, and also nitrile, nitro and carbonyl functional groups, said carbonyl groups being present in either ketones or aldehydes.Type: GrantFiled: April 7, 1978Date of Patent: January 26, 1982Assignee: Western Kentucky UniversityInventors: Norman L. Holy, William A. Logan, Karl D. Stein
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Patent number: 4307248Abstract: Supported coprecipitated catalysts comprised of one or more metals of Group VIII, one or more metals of Group IIA, and aluminum are used for hydrogenating hydrogenatable organic compounds. The catalysts are produced by preparing, under agitation; an aqueous mixture containing ions of Group VIII, Group IIA, and aluminum, as well as solid porous particles to form a coprecipitate of the metal ions and aluminum ions with the solid porous support particles; heating the aqueous reaction mixture; and adding precipitating agent to precipitate the metal ions and aluminum ions onto the solid support.Type: GrantFiled: November 28, 1980Date of Patent: December 22, 1981Assignee: Exxon Research & Engineering Co.Inventors: Allan E. Barnett, Albert P. Halluin
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Patent number: 4273939Abstract: Supported coprecipitated non-ferrous Group VIII metal aluminum catalysts are used for hydrogenating hydrogenatable organic compounds. The catalysts are produced by preparing an aqueous mixture containing the metal ions, aluminum ions and solid porous support particles under agitation to form a coprecipitate of the metal ions and aluminum ions with the solid porous support particles; heating the aqueous reaction mixture; and adding precipitating agent to further precipitate the metal ions and aluminum ions onto the solid support.Type: GrantFiled: November 6, 1979Date of Patent: June 16, 1981Assignee: Exxon Research & Engineering Co.Inventors: Allan E. Barnett, Albert P. Halluin
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Patent number: 4268377Abstract: Hydrocarbons are converted by contacting them at hydrocarbon conversion conditions with a novel activated multimetallic catalytic composite comprising a combination of a catalytically effective amount of a pyrolyzed ruthenium carbonyl component with a porous carrier material containing a uniform dispersion of a catalytically effective amount of a platinum group component, which is maintained in the elemental metallic state during the incorporation and pyrolysis of the ruthenium carbonyl component, and of a rhenium component. In a highly preferred embodiment, this novel catalytic composite also contains a catalytically effective amount of a halogen component. The platinum group component, pyrolyzed ruthenium carbonyl component, rhenium component and optional halogen component are preferably present in the multimetallic catalytic composite in amounts, calculated on an elemental basis, corresponding to about 0.01 to about 2 wt. % of the uniformly dispersed platinum group metal, about 0.01 to about 2 wt.Type: GrantFiled: October 5, 1979Date of Patent: May 19, 1981Assignee: UOP Inc.Inventor: George J. Antos
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Patent number: 4251672Abstract: A copper promoted massive nickel catalyst is disclosed which is capable of having a reduced nickel surface area ranging from about 55 to about 100 m.sup.2 /g as determined by hydrogen chemisorption, after reduction at 400.degree. C., and a B.E.T. total surface area ranging from about 150 to about 300 m.sup.2 /g, wherein the amount of copper in the catalyst ranges from about 2 wt. % to about 10 wt. % and the amount of nickel ranges from about 25 wt. % to about 50 wt. %, said wt. % of copper and nickel metal are based on the total weight of the catalyst. The copper promoted massive catalysts are prepared by the steps comprising comingling a solution containing copper and nickel cations with another solution containing silicate anions and coprecipitating the copper, nickel and silicate ions in an aqueous solution onto solid carrier particles. The catalysts are useful in hydrogenation processes.Type: GrantFiled: August 25, 1978Date of Patent: February 17, 1981Assignee: Exxon Research & Engineering Co.Inventors: James L. Carter, Allan E. Barnett
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Patent number: 4243824Abstract: A process for the preparation of novel zero-valent rhodium catalysts. The catalysts are prepared by the reaction of a hydrocarbyl-lithium compound with a hydrocarbon-soluble complex of a rhodium halide and a ligand. The catalyst may, if desired, be deposited on a support such as alumina or silica. It is effective to catalyze the hydrogenation of organic compounds such as benzene, styrene and the like.Type: GrantFiled: October 25, 1979Date of Patent: January 6, 1981Assignee: Borg-Warner CorporationInventors: Jan G. Noltes, Gerard van Koten, Murray S. Cohen
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Patent number: 4238358Abstract: Anthranilic acid has been anchored to polystyrene, and rhodium, palladium, platinum and ruthenium complexes of this modified polystyrene have been prepared. These catalysts will reduce a variety of olefinic and aromatic hydrocarbons, and also nitrile, nitro and carbonyl functional groups, said carbonyl groups being present in either ketones or aldehydes.Type: GrantFiled: March 29, 1979Date of Patent: December 9, 1980Assignee: Western Kentucky UniversityInventors: Norman L. Holy, William A. Logan, Karl D. Stein
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Patent number: 4228312Abstract: A process for the hydrogenation of certain aromatic, olefinic and acetylenic compounds. The process is catalyzed by a zero-valent mixed metal catalyst which is in turn prepared by the reaction of an organic metal cluster compound wherein one of the metals is lithium with a complex of rhodium halide and an olefinic hydrocarbon ligand. The catalyst may, if desired, be deposited on a support such as alumina or silica. The hydrogenation process can, in many instances, be carried out under ordinary conditions, i.e., at room temperature and atmospheric pressure.Type: GrantFiled: March 7, 1979Date of Patent: October 14, 1980Assignee: Borg-Warner CorporationInventors: Jan G. Noltes, J. T. B. H. Jastrzebski, Gerard van Koten
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Patent number: 4225733Abstract: Provided is a method for hydrogenating an aromatic compound by reacting the aromatic compound with hydrogen iodide in the presence of ruthenium catalyst.Type: GrantFiled: June 28, 1978Date of Patent: September 30, 1980Assignee: Agency of Industrial Science & TechnologyInventors: Tetsuya Kameyama, Masayuki Dokiya, Kenzo Fukuda
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Patent number: 4222898Abstract: A process for the preparation of novel zero-valent mixed catalysts. The catalysts are prepared by the reaction of an organic metal cluster compound wherein one of the metals is lithium with a complex of a rhodium halide and an olefinic hydrocarbon ligand. The catalyst may, if desired, be deposited on a support such as alumina or silica. It is effective to catalyze the hydrogenation of organic compounds such as benzene, styrene and the like.Type: GrantFiled: March 7, 1979Date of Patent: September 16, 1980Assignee: Borg-Warner CorporationInventors: Jan G. Noltes, J. T. B. H. Jastrzebski, Gerard van Koten
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Patent number: 4212990Abstract: Cyclohexane derivatives such as cyclohexanol, and cyclohexyl carboxylates are produced directly from aromatic hydrocarbons. The reaction may be carried out, under hydrogenation conditions, by reacting an aromatic hydrocarbon with hydrogen and a reagent selected from the group consisting of water and carboxylic acids in the presence of a strong acid and a hydrogenation catalyst.Type: GrantFiled: August 5, 1977Date of Patent: July 15, 1980Assignee: Toray Industries, Inc.Inventors: Yutaka Yasuhara, Masaki Nishino, Seikichi Matsuhira
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Patent number: 4205191Abstract: A process for the preparation of novel zero-valent metal catalysts. The catalysts are prepared by the reaction of an organic metal cluster compound wherein one of the metals is lithium with a complex of a metal halide and a ligand. The catalyst may, if desired, be deposited on a support such as alumina or silica. It is effective to catalyze the hydrogenation of organic compounds such as benzene, styrene and the like.Type: GrantFiled: November 20, 1978Date of Patent: May 27, 1980Assignee: Borg-Warner CorporationInventors: Murray S. Cohen, Jan G. Noltes, Gerard van Koten
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Patent number: 4197415Abstract: Aromatic hydrocarbons are selectively partially hydrogenated to cyclic olefins by contacting the aromatic hydrocarbon with hydrogen and a ruthenium catalyst in an aqueous dispersion containing a salt of a phosphorus acid.Type: GrantFiled: January 23, 1978Date of Patent: April 8, 1980Assignee: Toray Industries, Inc.Inventors: Aizawa Hideyuki, Kuroda Akio
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Patent number: 4187168Abstract: Hydrocarbon conversion processes wherein hydrocarbon feedstreams are contacted with heteronuclear noble metal catalysts are improved by the use of supported heteronuclear noble metal cluster catalysts prepared from novel supported heteronuclear noble metal cluster complexes. The heteronuclear noble metal cluster complexes used as catalyst precursors are selected from the group consisting of(pyridine).sub.2 Pt[Ir.sub.6 (CO).sub.15 ],(pyridine).sub.2 Pt[Ir.sub.2 (CO).sub.7 ],((C.sub.6 H.sub.5).sub.3 P).sub.2 Pt[IR(CO).sub.3 P(C.sub.6 H.sub.5).sub.3 ].sub.2,(pyridine).sub.2 Pt[Ru.sub.3 (CO).sub.12 ]((C.sub.6 H.sub.5).sub.3 P).sub.2 Rh(CO)[Ir(CO).sub.4 ],(pyridine).sub.2 Pt[Rh(CO).sub.2 (P(C.sub.6 H.sub.5).sub.3).sub.2 ].sub.2.Type: GrantFiled: July 13, 1978Date of Patent: February 5, 1980Assignee: Exxon Research & Engineering Co.Inventor: Gary B. McVicker
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Patent number: 4183804Abstract: Hydrocarbons are converted by contacting them at hydrocarbon conversion conditions with a novel activated multimetallic catalytic composite comprising a combination of a catalytically effective amount of a pyrolyzed ruthenium carbonyl component with a porous carrier material containing a uniform dispersion of a catalytically effective amount of a platinum group component which is maintained in the elemental metallic state. In a highly preferred embodiment, this novel catalytic composite also contains a catalytically effective amount of a halogen component. The platinum group component, pyrolyzed ruthenium carbonyl component and optional halogen component are preferably present in the multimetallic catalytic composite in amounts, calculated on an elemental basis, corresponding to about 0.01 to about 2 wt. % of the uniformly dispersed platinum group metal, about 0.01 to about 2 wt. % of carbonyl-derived ruthenium and about 0.1 to about 3.5 wt. % of halogen.Type: GrantFiled: November 4, 1977Date of Patent: January 15, 1980Assignee: UOP Inc.Inventor: George J. Antos
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Patent number: 4157313Abstract: Composite product, useful notably as a catalyst, comprising a coordination complex of a metal, notably of a transition metal, fixed to a support, wherein this support is formed of a solid mineral material, insoluble in organic solvets, and is covered at least partly by a polysiloxane, on which the coordinates of these complexes are grafted. This catalyst is stable in gaseous as well as in liquid media, and is useful for the hydrogenation of olefins in homogeneous and heterogeneous phases as well.Type: GrantFiled: December 2, 1977Date of Patent: June 5, 1979Assignee: Agence Nationale de Valorisation de la RechercheInventors: Jean Conan, Marie-France Llauro nee Darricades, Michel Bartholin, Alain Guyot