Opening Of Hydrocarbon Ring Patents (Class 585/940)
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Patent number: 7854834Abstract: The invention relates to a catalyst consisting of at least: one matrix comprising at least one oxide which is selected from an amorphous oxide, an oxide with low crystallinity and a mixture of both; at least one solid microporous crystalline material which, in the calcined and anhydrous state, has the molar compositions X2O3:nYO2:mZO2, in which X is a trivalent element such as, for example, Al, B, Fe, In, Ga, Cr, Y is at least one trivalent element that is different from Ge and Z is Ge, the value (n+m) is at least equal to 5 and can be between 5 and ?, and the value of n/m is at least equal to 1; and at least one hydrogenating compound, preferably Pt, Pd, Ir, Ru, Rh, and Re or a combination of same. The invention also relates to the use of said catalyst in a process in order to improve the quality of diesel fractions.Type: GrantFiled: August 25, 2009Date of Patent: December 21, 2010Assignees: Consejo Superior de Invetigaciones Cientificas, Universidad Politenica de ValenciaInventors: Avelino Corma Canos, Agustin Martinez Feliu, Fernando Rey García, María José Díaz Cabañas, Maria de los Desamparados Arribas Viana
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Patent number: 7608747Abstract: A process for the selective ring opening of ring-containing hydrocarbons in a feed stream having at least 10% ring-containing hydrocarbons includes contacting the feed stream with a ring opening catalyst containing a metal or a mixture of metals active for the selective ring opening of the ring-containing hydrocarbons on a support material, wherein the support material is a non-crystalline, porous inorganic oxide or mixture of inorganic oxides having at least 97 volume percent interconnected mesopores based on micropores and mesopores, and wherein the ring-containing hydrocarbons have at least one C6 ring and at least one substituent selected from the group consisting of fused 5- or 6-membered rings, alkyl, cycloalkyl and aryl groups.Type: GrantFiled: September 23, 2005Date of Patent: October 27, 2009Assignee: Lummus Technology Inc.Inventors: Bala Ramachandran, Lawrence L. Murrell, Martin Kraus, Zhiping Shan, Philip J. Angevine
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Patent number: 7513988Abstract: Less conventional sources of hydrocarbon feedstocks such as oil sands, tar sands and shale oils are being exploited. These feedstocks generate a larger amount of heavy oil, gas oil, asphaltene products and the like containing multiple fused aromatic ring compounds. These multiple fused aromatic ring compounds can be converted into feed for a hydrocarbon cracker by first hydrogenating at least one ring in the compounds and subjecting the resulting compound to a ring opening and cleavage reaction. The resulting product comprises lower paraffins suitable for feed to a cracker, higher paraffins suitable for example as a gasoline fraction and mono aromatic ring compounds (e.g. BTX) that may be further treated.Type: GrantFiled: September 1, 2006Date of Patent: April 7, 2009Assignees: Nova Chemicals (International) S.A., Universitat StuttgartInventors: Michael C. Oballa, Vasily Simanzhenkov, Jens Weitkamp, Roger Gläser, Yvonne Traa, Fehime Demir
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Patent number: 7094898Abstract: A new class of compounds is disclosed that in preferred embodiments relate to Ru-based catalysts suitable for use in olefin metathesis reactions. Such compounds demonstrate high rates of catalytic turnover in comparison with other Ru catalysts known in the art. Moreover, the catalysts are highly stable, and readily suited to attachment to a solid support via the anionic ligands. The invention also pertains to methods of producing the catalysts, and their use in catalyzing olefin metathesis reactions.Type: GrantFiled: May 28, 2004Date of Patent: August 22, 2006Assignee: University of OttawaInventors: Deryn Elizabeth Fogg, Jay Christopher Conrad
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Patent number: 6679986Abstract: A catalytic support includes a substantial quantity of at least one SVI group Periodic Table metal oxide in which is incorporated silica. The mass ratio between the quantity of SVI group metal oxide and the quantity of silica it contains ranges between 5 and 70, the SVI group metal oxide is in crystalline form, and the specific surface of the support is greater than or equal to 160 m2/g.Type: GrantFiled: May 16, 2000Date of Patent: January 20, 2004Assignee: Total Raffinage Distribution S.A.Inventors: Pedro Da Silva, Marc Bisson, Alain Milan, Sebastien Decker, Joeri Denayer
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Patent number: 6660813Abstract: An in-situ method for performing organic metathesis polymer chemistry in the solid state includes the step of providing an organic monomer and a catalyst, the catalyst for driving a metathesis polymerization reaction of the monomer. The organic monomer can be provided as a liquid monomer. The reaction produces reaction products including a polymeric end product and at least one volatile reaction product. At least a portion of the volatile reaction product is removed during the reaction to favor formation of the reaction product. Significantly, the reaction is performed at a temperature being below an average melting point of the polymeric end product such that at least a portion of the reaction is performed in the solid phase.Type: GrantFiled: August 1, 2002Date of Patent: December 9, 2003Assignee: University of FloridaInventors: Kenneth B. Wagener, Stephen E. Lehman, Jr., Garrett W. Oakley, Jason A. Smith
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Patent number: 6652737Abstract: Disclosed is a method for treating naphtha. The method comprises providing naphtha feed, and the naphtha feed comprises naphthene ring-containing compounds. The naphtha feed is contacted with a ring opening catalyst containing a Group VIII metal under conditions effective to ring open the naphthene rings to form a ring opened product. The ring open product can then be contacted with a catalytic cracking catalyst under effective cracking conditions to form an olefin product. The olefin product will be particularly high in ethylene and propylene content.Type: GrantFiled: July 2, 2001Date of Patent: November 25, 2003Assignee: ExxonMobil Research and Engineering CompanyInventors: Michele S. Touvelle, Darryl P. Klein, Tan-Jen Chen, Luc R. Martens, Edward S. Ellis
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Patent number: 6623625Abstract: Disclosed is a process for opening naphthenic rings of naphthenic ring-containing compounds, along with catalysts which can be used in that process. The naphthene ring opening catalyst is a catalyst which comprises at least one of a Group VIII metal selected from Ir, Pt, Pd, Rh, and Ru in an amount effective to ring open naphthene rings on naphthene ring-containing compounds, the metal being supported on a substrate comprising at least one Group IB, IIB, and IVA metal in an amount effective to moderate cracking of a naphthene ring-containing feed to form methane.Type: GrantFiled: July 2, 2001Date of Patent: September 23, 2003Assignee: ExxonMobil Research and Engineering CompanyInventors: William C. Baird, Jr., Jingguang G. Chen, Gary B. McVicker
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Patent number: 6589416Abstract: Disclosed is a process for opening naphthenic rings of naphthenic ring-containing compounds, and catalysts which can be used in that process. The naphthene ring opening catalyst is a polymetallic catalyst comprising Group VIII metals. In a preferred embodiment the naphthene ring opening catalyst comprises Ir in combination with a Group VIII metal selected from at least one of Pt, Rh, and Ru, in an amount effective for opening a naphthene ring-containing compound at a tertiary carbon site.Type: GrantFiled: July 2, 2001Date of Patent: July 8, 2003Assignee: ExxonMobil Research and Engineering CompanyInventors: William C. Baird, Jr., Darryl P. Klein, Michele S. Touvelle, Jingguang G. Chen
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Patent number: 6586650Abstract: A process for opening naphthenic rings of naphthenic ring-containing compounds, along with catalysts which can be used in that process. The naphthene ring opening catalyst is a catalyst comprising at least one Group VIII metal selected from Ir, Pt, Rh, and Ru, wherein these metals are supported on an alkali metal or alkaline-earth metal modified support in an amount effective for opening a naphthene ring-containing compound at a tertiary carbon site.Type: GrantFiled: July 2, 2001Date of Patent: July 1, 2003Assignee: ExxonMobil Research and Engineering CompanyInventors: William C. Baird, Jr., Darryl P. Klein, Michele S. Touvelle, Jingguang G. Chen, Gary B. McVicker
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Publication number: 20020063082Abstract: Disclosed is a method for treating naphtha. The method comprises providing naphtha feed, and the naphtha feed comprises naphthene ring-containing compounds. The naphtha feed is contacted with a ring opening catalyst containing a Group VIII metal under conditions effective to ring open the naphthene rings to form a ring opened product. The ring open product can then be contacted with a catalytic cracking catalyst under effective cracking conditions to form an olefin product. The olefin product will be particularly high in ethylene and propylene content.Type: ApplicationFiled: July 2, 2001Publication date: May 30, 2002Inventors: Michele S. Touvelle, Darryl P. Klein, Tan-Jen Chen, Luc R. Martens, Edward S. Ellis
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Publication number: 20020045791Abstract: After 1,5,9-cyclododecatriene is epoxidized with hydrogen peroxide in the presence of a catalyst containing a tungsten compound, a quaternary onium salt and a mineral acid, to obtain a liquid reaction mixture containing the resultant 1,2-epoxy-5,9-cyclododecadiene, the catalyst, non-reacted hydrogen peroxide and non-reacted 1,5,9-cyclododecatriene and being phase-separated into an oil phase fraction and an aqueous phase fraction, at least the oil phase fraction of the liquid reaction mixture is treated with an aqueous alkali solution to deactivate and remove the non-reacted hydrogen peroxide and the catalyst contained in at least the oil phase fraction.Type: ApplicationFiled: July 2, 2001Publication date: April 18, 2002Applicant: Ube Industries, Ltd.Inventors: Kouhei Ninomiya, Tsunemi Sugimoto, Junichi Kugimoto, Mitsuo Yamanaka, Kohji Kaiso
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Publication number: 20020040175Abstract: Disclosed is a process for opening naphthenic rings of naphthenic ring-containing compounds, along with catalysts which can be used in that process. The naphthene ring opening catalyst is a catalyst which comprises at least one of a Group VIII metal selected from Ir, Pt, Pd, Rh, and Ru in an amount effective to ring open naphthene rings on naphthene ring-containing compounds, the metal being supported on a substrate comprising at least one Group IB, IIB, and IVA metal in an amount effective to moderate cracking of a naphthene ring-containing feed to form methane.Type: ApplicationFiled: July 2, 2001Publication date: April 4, 2002Inventors: William C. Baird, Jingguang G. Chen, Gary B. McVicker
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Publication number: 20020040176Abstract: Disclosed is a process for opening naphthenic rings of naphthenic ring-containing compounds, along with catalysts which can be used in that process. The ring opening is accomplished using a ring opening catalyst comprises Ir on a composite support of alumina and acidic silica-alumina molecular sieve. The ring opening activity is not significantly deactivated by exposure to oxygen at greater than about 250° C.Type: ApplicationFiled: July 2, 2001Publication date: April 4, 2002Inventors: William C. Baird, Darryl P. Klein, Jingguang G. Chen, Gary B. McVicker
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Publication number: 20020038068Abstract: Disclosed is a process for opening naphthenic rings of naphthenic ring-containing compounds, along with catalysts which can be used in that process. The ring opening is accomplished using a ring opening catalyst system which combines an Ir ring opening catalyst with a Pt and Pd catalyst. The combination of the Pt and Pd-containing catalyst with an Ir-containing catalyst incorporates desirable isomerization activity and also results in substantial ring opening activity that enables Ir to be loaded at a level that is substantially below that of Ir-only ring opening processes.Type: ApplicationFiled: July 2, 2001Publication date: March 28, 2002Inventors: William C. Baird, Jingguang G. Chen, Gary B. McVicker
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Patent number: 6346652Abstract: A composition and method for the catalytic conversion of a racemic mixture of dienes to a cyclic olefin by a ring-closing metathesis (RCM) reaction are disclosed. The composition, a transition metal complex with an M═C reaction site, contains a bidentate dialkoxide of at least 80% optical purity. Because the M═C reaction site is of a sufficient shape specificity, conferred in part by the dialkoxide of sufficient rigidity and a M═N—R1 site, reacting the composition with a mixture of two enantiomeric dienes results in an olefin metathesis product that has at least a 50% enantiomeric excess of one enantiomer in the mixture. A method is also provided for reacting a composition with a racemic diene mixture to generate a metathesis product that has an enantiomeric excess of at least 50%. Methods are also provided for catalytic enantioselective desymmetrization.Type: GrantFiled: July 13, 1998Date of Patent: February 12, 2002Assignee: Massachusetts Institute of TechnologyInventors: Richard R. Schrock, Amir H. Hoveyda
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Acid activation of ruthenium metathesis catalysts and living ROMP metathesis polymerization in water
Patent number: 6284852Abstract: Activation of ruthenium based catalyst compounds with acid to improve reaction rates and yields of olefin metathesis reactions, including ROMP, RCM, ADMET and cross-metathesis reactions is disclosed. The ruthenium catalyst compounds are ruthenium carbene complexes of the general formula AxLyXzRu═CHR′ where x=0, 1 or 2, y=0, 1 or 2, and z=1 or 2 and where R′ is hydrogen or a substituted or unsubstituted alkyl or aryl, L is any neutral electron donor, X is any anionic ligand, and A is a ligand having a covalent structure connecting a neutral electron donor and an anionic ligand. The use of acid with these catalysts allows for reactions with a wide range of olefins in a variety of solvents, including acid-initiated RIM processes and living ROMP reactions of water-soluble monomers in water.Type: GrantFiled: October 29, 1998Date of Patent: September 4, 2001Assignee: California Institute of TechnologyInventors: David M. Lynn, Eric L. Dias, Robert H. Grubbs, Bernard Mohr -
Patent number: 6235962Abstract: A catalyst for ring opening of cyclic organic compounds comprising, on a carrier of alumina, silica, zirconia and mixtures thereof, from 0.1 to 10% by weight based on the total weight of the catalyst of a catalytic active metal selected from platinum, palladium, rhodium, rhenium, iridium, ruthenium, nickel, cobalt and mixtures or combinations thereof and from 0.01 to 20% by weight based on the total weight of the catalyst of a metal modifier selected from tungsten, molybdenum lanthanum and rare earth metals and mixtures and combinations thereof.Type: GrantFiled: April 27, 1998Date of Patent: May 22, 2001Assignee: Haldor Topsoe A/SInventor: Per Zeuthen
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Patent number: 5831139Abstract: A process combination is disclosed to selectively upgrade naphtha in accordance with expected trends leading to more-aliphatic gasolines. Such gasolines contain lower concentrations of aromatics and have lower end points with concomitant reduced harmful automotive emissions. The present process combination converts the higher-boiling portion of the naphtha, yields isobutane and other isoparaffins which are particularly suitable for upgrading or blending, and reduces cyclics in intermediate processing steps.Type: GrantFiled: March 26, 1997Date of Patent: November 3, 1998Assignee: UOP LLCInventors: Robert J. Schmidt, Paula L. Bogdan, Leonid B. Galperin, Jennifer S. Holmgren
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Patent number: 5770042Abstract: A process combination is disclosed to selectively upgrade naphtha to obtain an isoparaffin-rich product for blending into gasoline. A naphtha feedstock is subjected to ring cleavage to convert naphthenes to paraffins using a nonacidic catalyst followed by isomerization of paraffins to obtain an increased proportion of isoparaffins. Ring cleavage also may be effected on the product of isomerization and separation by fractionation or adsorption.Type: GrantFiled: October 31, 1995Date of Patent: June 23, 1998Assignee: UOPInventors: Leonid B. Galperin, Jeffery C. Bricker, Jennifer S. Holmgren
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Patent number: 5763731Abstract: Naphthenic rings in naphthenic ring-containing compounds in a feedstream are selectively opened wherein at least about 50 wt. % of the ring compounds in the feedstream are characterized as containing at least one C.sub.6 ring having at least one substituent containing 3 or more carbon atoms. The naphthenic rings are opened without significant dealkylation of any pendant substituents on the ring. The feedstream, containing such compounds, is contacted with a supported catalyst containing a metal selected from Ir, Ru, or a mixture thereof, which catalyst when reacted with a feed comprised of 20 wt. % n-butylcyclohexane in heptane diluent will result in: a) at least a 10% yield of C.sub.10 paraffin yield/%C.sub.10 ring disappearance.Type: GrantFiled: April 12, 1996Date of Patent: June 9, 1998Assignee: Exxon Research and Engineering CompanyInventors: Gary B. McVicker, Michele S. Touvelle, Carl W. Hudson, David E. W. Vaughan, Michel Daage, Sylvain Hantzer, Darryl P. Klein, Edward S. Ellis, Bruce R. Cook, Owen C. Feeley, Joseph E. Baumgartner
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Patent number: 5498810Abstract: A process combination is disclosed to selectively upgrade naphtha to obtain products suitable for further upgrading to reformulated fuels. A naphtha feedstock is hydrogenated to saturate aromatics, followed by selective isoparaffin synthesis to yield light and heavy naphtha and isobutane; isobutane and isopentane in the product are obtained in superequilibrium concentrations. The heavy naphtha may be processed by reforming, light naphtha may be isomerized, and isobutane may be upgraded by dehydrogenation, etherification and/or alkylation to yield gasoline components from the process combination suitable for production of reformulated gasoline.Type: GrantFiled: August 19, 1994Date of Patent: March 12, 1996Assignee: UOPInventors: Paula L. Bogdan, R. Joe Lawson, J. W. Adriaan Sachtler, Robert J. Schmidt
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Patent number: 5382730Abstract: There is provided a process for ring opening of aromatics and cycloaliphatics, as well as isomerization of aliphatics. The feedstream to this process comprises hydrocarbons having 6 carbon atoms. The process involves the use of at least two reactors connected in series. The first reactor comprises a zeolite catalyst and is operated under conditions which particularly promote ring opening. The catalyst in this first reactor may comprise zeolite Beta and platinum. A downstream reactor is operated under conditions to promote isomerization of aliphatics. The catalyst in the second reactor may comprise alumina, platinum and a chloride component. Hydrogen in the effluent of the first reactor may be removed and recycled to the first reactor. Hydrogen required for the second reactor may be satisfied by hydrogen remaining dissolved in the effluent from the first reactor after hydrogen is recycled to the first reactor.Type: GrantFiled: July 12, 1993Date of Patent: January 17, 1995Assignee: Mobil Oil Corp.Inventors: Lloyd L. Breckenridge, Kenneth J. Del Rossi, Albin Huss, Jr., Clinton R. Kennedy, Garry W. Kirker
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Patent number: 5382731Abstract: There is provided a process for ring opening of aromatics or cycloaliphatics, as well as isomerization of aliphatics. The feedstream to this process comprises hydrocarbons having 6 carbon atoms. The process involves the use of a recycle stream containing a source of chlorine, such as carbon tetrachloride, and this process involves the use of at least two reactors connected in series. The first reactor comprises a ring opening catalyst and is operated under conditions which particularly promote ring opening. The catalyst in this first reactor may comprise zirconia modified with tungstate and platinum. A second, downstream reactor is operated under conditions to promote isomerization of aliphatics. The catalyst in the second reactor may comprise alumina, platinum and a chloride component. The catalysts in both the first and second reactors are chlorine resistant.Type: GrantFiled: July 22, 1993Date of Patent: January 17, 1995Assignee: Mobil Oil Corp.Inventors: Clarence D. Chang, Roy D. Bastian, Scott Han, Jose G. Santiesteban
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Patent number: 5345026Abstract: There is provided a ring opening process using a catalyst comprising a hydrogenation/dehydrogenation component, such as a noble metal, and an acidic solid component comprising a Group IVB metal oxide modified with an oxyanion of a Group VIB metal. An example of this catalyst is zirconia, modified with tungstate and platinum. This catalyst is used to convert cyclic hydrocarbons, such as cyclohexane and benzene, to paraffins, especially branched paraffins.Type: GrantFiled: July 22, 1993Date of Patent: September 6, 1994Assignee: Mobil Oil Corp.Inventors: Clarence D. Chang, Jose G. Santiesteban, David L. Stern
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Patent number: 5334792Abstract: There is provided a process for ring opening of aromatics and cycloaliphatics, as well as isomerization of aliphatics. The feedstream to this process comprises hydrocarbons having 6 carbon atoms. The process involves the use of at least two reactors connected in series. The first reactor contains a zeolite catalyst and is operated under conditions which particularly promote ring opening. The catalyst in this first reactor may comprise zeolite Beta and platinum. A downstream reactor is operated under conditions to promote isomerization of aliphatics. The catalyst in the second reactor may comprise alumina, platinum and a chloride component.Type: GrantFiled: October 9, 1992Date of Patent: August 2, 1994Assignee: Mobil Oil CorporationInventors: Kenneth J. Del Rossi, David J. Dovedytis, David J. Esteves, Mohsen N. Harandi, Albin Huss, Jr.
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Patent number: 5082983Abstract: A process for reducing the benzene content of a reformate stream in a conventional catalytic cracking reactor wherein a heavy hydrocarbon feed is cracked to lighter products by contact with a supply of hot regenerated cracking catalyst is disclosed. The reformate can be mixed with the heavy feed to the cracking reactor, but preferably reformate contacts hot regenerated cracking catalyst before the heavy feed is added. Benzene content is reduced by alkylation with reactive fragments created in the cracking reactor, or by transalkylation with alkyl aromatics. Benzene removal can be enhanced by adding a light reactive gas such as ethylene to the cracking reactor, by adding heavier aromatics, such as a light cycle oil, or both. The reaction is preferably conducted in an FCC riser reactor, but may be conducted in a moving bed cracking reactor.Type: GrantFiled: September 14, 1990Date of Patent: January 21, 1992Assignee: Mobil Oil CorporationInventors: Lloyd L. Breckenridge, Diane V. Jorgensen, Ajit V. Sapre
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Patent number: 4783575Abstract: A C.sub.4 -C.sub.6 feed to an isomerization zone containing substantial amounts of cyclic hydrocarbons is contacted with a high chloride, platinum alumina catalyst to simultaneously open cyclic hydrocarbon rings and isomerize paraffins to more highly branched paraffins. The process can operate at relatively low severity conditions that provide favorable equilibrium conditions for isoparaffin conversion. The ring opening is also obtained without excessive generation of light hydrocarbons. Multiple stage reaction zones may be used to operate the first stage at slightly higher severity than the second stage to maximize ring opening and obtain favorable equilibrium of iso to normal paraffins.Type: GrantFiled: December 17, 1987Date of Patent: November 8, 1988Assignee: UOP Inc.Inventors: Robert J. Schmidt, Laurence O. Stine
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Patent number: 4513163Abstract: The present invention provides a process for producing iso-paraffins from aromatic hydrocarbons comprising contacting the aromatic hydrocarbon or aromatic hydrocarbon-containing feed with a molten salt system comprising sodium tetrachloroaluminate (NaAlCl.sub.4) and up to about 25 weight percent hydrogen tetrachloroaluminate (HAlCl.sub.4) at a temperature above about 155.degree. C., i.e. that required to maintain the molten state of said mixture, whereby the ring structure is opened and the aromatic compound is rearranged to an iso-paraffin of the same or substantially the same molecular weight.Type: GrantFiled: December 30, 1983Date of Patent: April 23, 1985Assignee: Marathon Oil CompanyInventor: Mark A. Plummer
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Patent number: 4300013Abstract: A silica-containing material related to zeolites and referred to hereinafter as FU-1 has the composition 0.6 to 1.4 R.sub.2 O.Al.sub.2 O.sub.3.over 5 SiO.sub.2.O to 40 H.sub.2 O, (where R is a monovalent cation or 1/n of a cation of valency n) and is characterized inter alia by its X-ray diffraction pattern. It can be made by hydrothermal synthesis in presence of methylated quaternary onium compounds. It is useful as a catalyst for hydrocarbon conversion reactions, especially isomerization of xylenes.Type: GrantFiled: June 12, 1980Date of Patent: November 10, 1981Assignee: Imperial Chemical Industries LimitedInventor: Thomas V. Whittam
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Patent number: 4175033Abstract: A process for hydrotreating (hydroprocessing) hydrocarbons and mixtures of hydrocarbons utilizing a catalytic composite comprising a combination of a nickel component, a molybdenum component and a platinum component with a zeolitic carrier material wherein said platinum component is present in an amount sufficient to result in the composite containing, on an elemental basis, about 0.2 to about 0.5 percent by weight platinum, in which process there is effected a chemical consumption of hydrogen. Hydrocarbon hydroprocesses are hydrocracking, the hydrogenation of aromatic nuclei, the ring-opening of cyclic hydrocarbons, desulfurization, denitrification, hydrogenation, etc.Type: GrantFiled: December 18, 1978Date of Patent: November 20, 1979Assignee: UOP Inc.Inventor: Lee Hilfman