Using S-containing Catalyst Patents (Class 585/458)
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Patent number: 9783462Abstract: A method of producing a purified mixed xylene comprising: introducing toluene and methanol to an alkylation reactor (32); reacting the toluene and the methanol in the alkylation reactor (32) to form a hydrocarbon stream (22) comprising a first mixed xylene, wherein the alkylation reactor (32) comprises an alkylation catalyst; separating the hydrocarbon stream (22) into a toluene stream (24) and a separated C8+ stream (14); introducing the toluene stream (24) to a transalkylation reactor (38) with a transalkylation catalyst to produce a transalkylated stream (17) comprising a second mixed xylene; adding the transalkylated stream (17) to the hydrocarbon stream (22); and separating a C8 product stream (19) comprising the purified mixed xylene from the separated C8+ stream (14).Type: GrantFiled: September 10, 2013Date of Patent: October 10, 2017Assignee: SAUDI BASIC INDUSTRIES CORPORATIONInventors: Ashim Kumar Ghosh, Mohamed Elbaccouch, Mohammad Shafiei, Murali Gopalakrishnan
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Publication number: 20100160703Abstract: A process for alkylating an aromatic compound containing no hydroxyl groups comprising reacting at least one non-hydroxyl containing aromatic compound with at least one olefinic oligomer in the presence of an acidic ionic liquid catalyst, wherein the olefinic oligomer has a carbon range of from about C12 to about C70 and is synthesized by oligomerizing at least one monoolefin monomer in the presence of an acidic ionic liquid catalyst.Type: ApplicationFiled: February 19, 2010Publication date: June 24, 2010Applicant: Chevron Oronite Company LLCInventors: Michael Driver, Curt B. Campbell, Thomas V. Harris
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Patent number: 7737312Abstract: This invention relates to a process for producing linear alkyl benzene, the process including the steps of obtaining a hydrocarbon condensate containing olefins, paraffins and oxygenates from a low temperature Fischer-Tropsch reaction; a) fractionating a desired carbon number distribution from the hydrocarbon condensate to form a fractionated hydrocarbon condensate stream; b) extracting oxygenates from the fractionated hydrocarbon condensate stream from step (a) to form a stream containing olefins and paraffins; c) combining the stream containing olefins and paraffins from step (b) with the feed stream from step (g) to form a combined stream; d) alkylating olefins in the combined stream from step (c) with benzene in the presence of a suitable alkylation catalyst in an alkylation reactor; e) recovering linear alkyl benzene from the alkylation reactor; f) recovering unreacted paraffins from the alkylation reactor; g) dehydrogenating the unreacted paraffins in the presence of a suitable dehydrogenation catalystType: GrantFiled: March 10, 2004Date of Patent: June 15, 2010Assignee: Sasol Technology (Proprietary) LimitedInventors: Ivan Greager, Jan Hendrik Scholtz, Johan Pieter de Wet, Mieke Ann Desmet, Wilhelmina Jansen, Paul Jacobson, Luis Pablo Fidel Dancuart
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Patent number: 7495140Abstract: A process for alkylating an aromatic compound comprising reacting (a) a first amount of at least one aromatic compound with a first amount of a mixture of olefins having from about 8 to about 100 carbon atoms, in the presence of a strong acid catalyst; and reacting the product of (a) with an additional amount of at least one aromatic compound and an additional amount of a strong acid catalyst, and optionally, with an additional amount of a mixture of olefins selected from olefins having from about 8 to about 100 carbon atoms, wherein the resulting product comprises at least about 80 weight percent of a 1,2,4 tri-alkylsubstituted aromatic compound.Type: GrantFiled: June 1, 2006Date of Patent: February 24, 2009Assignee: Chevron Cronite Company LLCInventors: Curt B. Campbell, Gilles Sinquin
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Patent number: 7297827Abstract: Disclosed is an alkylation reactor for preparing ethylbenzene. The reactor comprises a monolith catalyst system that includes a monolith support impregnated or co-formed with a catalyst suitable to catalyze the alkylation of benzene with ethylene. The catalyst may be selected from, for example, zeolites such as beta zeolite and MCM-22 zeolite, and fixed super acids. Also disclosed is a method of preparing ethylbenzene by alkylating a mixture of benzene and ethylene in an alkylation reactor comprising a monolith catalyst system, including a monolith support impregnated or co-formed with a suitable catalyst. In one embodiment the invention provides a convenient means of upgrading an existing reactor that has previously been used for conventional liquid phase alkylations such as those catalyzed by aluminum trichloride. The inventive alkylation method may be effectively and advantageously carried out under critical or near critical conditions, if desired.Type: GrantFiled: November 29, 2004Date of Patent: November 20, 2007Assignee: Fina Technology, Inc.Inventor: Kevin Kelly
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Patent number: 7294420Abstract: A method of producing hydrogen for a fuel cell from a hydrocarbon fuel composition, by providing a hydrocarbon fuel composition, which is obtained by contacting a liquid hydrocarbon feed comprising an alkylating agent with an acidic catalyst, under conditions effective to alkylate at least a portion of the hydrocarbon feed; converting the hydrocarbon fuel composition into hydrogen; and optionally, introducing the hydrogen produced into a fuel cell. In a preferred embodiment the liquid hydrocarbon feed further comprises sulphur-containing impurities, at least a portion of which are alkylated during the alkylation step.Type: GrantFiled: August 28, 2002Date of Patent: November 13, 2007Assignee: BP P.L.C.Inventor: Michael Graham Hodges
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Patent number: 7161052Abstract: A process is described for the valorization of a charge of hydrocarbons and for reducing the vapour pressure of said charge, comprising three steps: a step a) consisting of separating said charge of hydrocarbons into a fraction (O1) comprising essentially compounds containing 5 carbon atoms, including at least 2% by weight of pentenes, a step b) consisting of placing said fraction (O1) in contact with a cut of hydrocarbons (O2) at least partly comprising hydrocarbons having a number of carbon atoms between 6 and 10, including at least 2% by weight of olefins, and a step c) consisting of separating the effluents originating from step b) into a gasoline cut (?) the upper distillation point of which is less than 100° C. and a kerosene cut (?) having a distillation range between 100° C. and 300° C.Type: GrantFiled: September 3, 2003Date of Patent: January 9, 2007Assignee: Institut Francais de PetroleInventors: Patrick Briot, Vincent Coupard, Alain Forestiere, Eric Llido, Thierry Poussereau
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Patent number: 6605566Abstract: A novel supported bimetallic catalyst comprises a group VIII metal such as platinum, and tin, at least a portion of which interacts strongly with the group VIII metal in the catalyst in the reduced state. In the partially oxidized state, the catalyst of the invention contains at least 10% of tin in the form of a reduced tin species with oxidation state 0, said species having an isomer shift in the range 0.80 to 2.60 mm/s and a quadrupolar splitting in the range 0.65 to 2.00 mm/s. The invention also concerns the preparation of said catalyst, and processes using said catalyst for transforming hydrocarbons into aromatic compounds, such as gasoline reforming processes and aromatic production processes.Type: GrantFiled: August 23, 2001Date of Patent: August 12, 2003Assignee: Institut Francais du PetroleInventors: Fabienne Le Peltier, Blaise Didillon, Jean-Claude Jumas, Josette Olivier-Fourcade
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Patent number: 6573415Abstract: Process for the mono alkylation of a hydrocarbon substrate containing aromatic hydrocarbon compounds comprising contacting the aromatic substrate with an alkylating agent consisting of a mixture of olefinic compounds and poly-alkylated aromatic compounds in presence of a fluorinated sulphonic acid.Type: GrantFiled: August 20, 2001Date of Patent: June 3, 2003Assignee: Haldor Topsoe A/SInventors: Sven Ivar Hommeltoft, Karsten Laurents
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Patent number: 6436866Abstract: Disclosed is a Lewis acid catalyst composition comprising a specific mixed medium and a Lewis acid catalyst (II), wherein the specific mixed medium is mixed medium (I) comprising a perfluorinated aliphatic hydrocarbon (A) and at least one non-fluorinated hydrocarbon or a mixed medium (I′) comprising a perfluorinated aliphatic hydrocarbon (A), a perfluorinated aromatic hydrocarbon (C) and water (D), and wherein the Lewis acid catalyst (II) is at least one compound selected from the group consisting of compounds respectively represented by the following formulae (1), (2) and (3): (RfSO3)nM (1), [(RfSO2)2N]nM (2), and [(RfSO2)3C]nM (3). Also disclosed is a Lewis acid catalyst represented by the above-mentioned formula (3).Type: GrantFiled: May 26, 2000Date of Patent: August 20, 2002Assignee: Asahi Kasei Kabushiki KaishaInventors: Joji Nishikido, Hitoshi Nakajima
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Patent number: 6420305Abstract: A method for producting a solid acid catalyst is provided which produces a shaped material of a solid acid catalyst containing a sulfureous component but have a high activity and having a practically sufficient handleability and mechanical strength involves the steps of (a) fabricating a support containing a portion of zirconia and/or hydrated zirconia and a portion of alumina and/or hydrated alumina and having a peak diameter in the range of 0.05 to 1 &mgr;m in a pore diameter distribution of 0.05 to 10 &mgr;m; and having a sulfuerous component supported on the support or (b) fabricating a support containing a portion of zirconia and/or hydrated zirconia and a portion of alumina and/or hydrated alumina and including pores having a pore diameter of not less than 0.05 &mgr;m and not more than 1 &mgr;m occupying a pore volume of 0.05 to 0.5 ml/g and pores having a pore diameter of about 1 &mgr;m and not more than 10 &mgr;m occupying a pore volume of below 0.Type: GrantFiled: August 11, 2000Date of Patent: July 16, 2002Assignee: Japan Energy CorporationInventors: Kenji Matsuzawa, Kohjiroh Aimoto, Kazuhiro Seki
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Publication number: 20020045788Abstract: Process for the mono alkylation of a hydrocarbon substrate containing aromatic hydrocarbon compounds comprising contacting the aromatic substrate with an alkylating agent consisting of a mixture of olefinic compounds and poly-alkylated aromatic compounds in presence of a fluorinated sulphonic acid.Type: ApplicationFiled: August 20, 2001Publication date: April 18, 2002Applicant: Haldor Topsoe A/SInventors: Sven I. Hommeltoft, Karsten Laurents
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Patent number: 6340414Abstract: Process for the recovery of fluorinated sulphonic acid including the step of subjecting the spent acid to heat treatment with stepwise or continuously increasing temperature, withdrawing at least two fractions during the heat treatment; and recovering the fluorinated sulphonic acid from each fraction.Type: GrantFiled: July 7, 1999Date of Patent: January 22, 2002Assignee: Haldor Topsoe A/SInventor: Sven Ivar Hommeltoft
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Patent number: 6281400Abstract: The present invention relates to a process for preparing a microcomposite comprising a highly fluorinated ion-exchange polymer containing pendant sulfonate functional groups, said polymer existing as aggregated particles entrapped within and dispersed throughout a network of silica. Due to their high surface area and acid functionality, these microcomposites possess wide utility as improved solid acid catalysts, particularly in the substitution of aromatic compounds, in the decomposition of hydroperoxides, and in the isomerization of olefins.Type: GrantFiled: January 14, 2000Date of Patent: August 28, 2001Assignee: E. I. du Pont de Nemours and CompanyInventors: Mark Andrew Harmer, Qun Sun
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Patent number: 6160190Abstract: Porous microcomposites have been prepared from perfluorinated ion-exchange polymer and metal oxides such as silica using the sol-gel process. Such microcomposites possess high surface area and exhibit extremely high catalytic activity. The microcomposites catalyze, among others, the reaction between organic aromatic compounds and olefins.Type: GrantFiled: June 3, 1999Date of Patent: December 12, 2000Assignee: E. I. du Pont de Nemours and CompanyInventors: Mark Andrew Harmer, Qun Sun
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Patent number: 6133493Abstract: This invention concerns a modified porous microcomposite comprising a perfluorinated ion-exchange polymer entrapped within and highly dispersed throughout a network of inorganic oxide wherein the network and optionally the pendant groups of the polymer have been modified with a Lewis acid. These modified microcomposites can be used in catalyst compositions for various chemical processes, such as in the alkylation or acylation of aromatics.Type: GrantFiled: May 6, 1999Date of Patent: October 17, 2000Assignee: E. I. du Pont de Nemours and CompanyInventors: Mark Andrew Harmer, Qun Sun
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Patent number: 6123836Abstract: Process for the removal of acid compounds contained in a hydrocarbon process stream by passing the process stream through a fixed bed of an adsorption material at conditions where the acid compounds adsorb on the material and withdrawing a purified hydrocarbon process stream, wherein water has been adsorbed on the material prior to contact with the hydrocarbon process stream.Type: GrantFiled: July 2, 1998Date of Patent: September 26, 2000Assignee: Haldor Topsoe A/SInventors: Sven Ivar Hommeltoft, Karsten Laurents
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Patent number: 5986155Abstract: Treating low reactivity alkylating agents in the vapor phase with catalysts converts the low reactivity alkylating agents to high reactivity alkylating agents. The alkylating agents are useful in synthesis of alkyl aromatics with Lewis acid catalysts.Type: GrantFiled: July 10, 1996Date of Patent: November 16, 1999Assignee: The Lubrizol CorporationInventors: James D. Burrington, Stuart L. Bartley, Douglas C. Rhubright, Paul A. Lewis, Marvin B. DeTar, Alicia L. Kliever, Frank A. Del Greco, Lawrence T. Novak
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Patent number: 5959169Abstract: Process for the selective removal of aromatic compounds from a hydrocarbon mixture by contacting the mixture in presence of an olefinic alkylating agent with an alkylation catalyst selected from the group of fluorinated alkyl sulphonic acids movably adsorbed on a silica comprising carrier material.Type: GrantFiled: April 2, 1998Date of Patent: September 28, 1999Assignee: Haldor Topsoe A/SInventor: Sven Ivar Hommeltoft
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Patent number: 5877383Abstract: A process for the manufacture of a hydrocarbon mixture being rich in middle distillate products with the boiling part range of 175.degree.-360.degree. C. by alkylation of a hydrocarbon feed stock with an olefinic alkylating agent, comprises the steps of contacting a hydrocarbon feedstock and an olefinic alkylating agent with a catalyst composition containing an acid selected from the group of fluorinated alkane sulphonic acids having the general formula: ##STR1## wherein R'=F, Cl, Br, I, H, an alkyl or perfluoro alkyl group,R"=H, alkyl, aryl or a perfluoro alkoxy group, andrecovering a product stream of alkylated hydrocarbons and optionally recycling to the reactor lower isoalkanes being formed during the alkylation.Type: GrantFiled: November 5, 1997Date of Patent: March 2, 1999Assignee: Haldor Topsoe A/SInventors: Sven Ivar Hommeltoft, Annemarie Bauer
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Patent number: 5849965Abstract: In a multistage process, a relatively unreactive paraffinic substrate is alkylated in a primary stage while a more reactive aromatic substrate is alkylated in a secondary stage wherein at least a portion of the effluent from the primary stage is used as a diluent in the secondary stage. The alkylation reaction in each stage is catalyzed by an acid catalyst which is adsorbed on a particulate solid support.Type: GrantFiled: May 22, 1997Date of Patent: December 15, 1998Assignee: Amoco CorporationInventors: Robert L. Mehlberg, George A. Huff, Jr.
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Patent number: 5750818Abstract: A process for cooling unreacted hydrocarbon substrate that is recycled to an alkylation reactor and for minimizing the concentration of lower boiling hydrocarbons in such recycle.Type: GrantFiled: June 20, 1996Date of Patent: May 12, 1998Assignee: Amoco CorporationInventors: Robert L. Mehlberg, James B. Young
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Patent number: 5663474Abstract: This invention relates to catalysts for alkylation reactions and their preparation. More particularly, the invention relates to an alkylation process using a hydrogen fluoride-containing alkylation catalyst, which catalyst may be safely and easily handled, transported, and stored.Type: GrantFiled: March 7, 1996Date of Patent: September 2, 1997Assignee: AlliedSignal Inc.Inventors: Hang Thanh Pham, Robert Pratt, Charles Lewis Redmon, John James Thompson, Michael Van Der Puy, Rajiv Ratna Singh, William James Hague, Harold John Kieta, Matthew Hermes Luly, Jeffrey Warren McKown
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Patent number: 5475162Abstract: A process of effecting an acid catalyzed reaction wherein a reactant capable of undergoing an acid catalyzed reaction is contacted with an acid functionalized organically-bridged polysilsesquioxane catalyst where all of the acid functionality is covalently bonded to the organic portion of an organically-bridged polysilsesquioxane framework has been developed. The acid functionalized organically-bridged polysilsesquioxane is formed by polymerizing a monomer through sol-gel processing to form an organically-bridged polysilsesquioxane, reacting an acid group onto the organic portion of the organically-bridged polysilsesquioxane, and recovering the acid functionalized product. An embodiment of the invention is where the acid catalyzed reaction is the hydration of olefins, alkylation, acylation, isomerization, or aldol condensation/elimination.Type: GrantFiled: July 19, 1994Date of Patent: December 12, 1995Assignee: UOPInventors: Timothy A. Brandvold, Jennifer S. Holmgren, Thomas P. Malloy
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Patent number: 5472921Abstract: Process for the recovery of fluorinated sulphonic acid catalyst from tar being formed during alkylation of hydrocarbons in the presence of the fluorinated sulphonic acid catalyst and containing spent fluorinated sulphonic acid catalyst in form of salts with basic components in the tar, which process comprises,treating the tar with an alkyl ester of sulphuric acid to form a fluorinated sulphonic acid alkyl ester;separating the obtained ester from the tar by stripping the ester off the tar with an inert stripping agent; and finallyrecovering the separated sulphonic acid alkyl ester from the stripping agent.Type: GrantFiled: April 19, 1994Date of Patent: December 5, 1995Assignee: Haldor Topsoe A/SInventor: Sven I. Hommeltoft
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Patent number: 5434326Abstract: This invention presents a novel MgAPSO molecular sieve, containing a critical range of magnesium in the sieve framework and having a small crystallite size, which is particularly active for hydrocarbon conversion. The sieve advantageously is incorporated, along with a refractory inorganic oxide, into a catalyst formulation which is useful for alkylation. When utilized in a process for alkylating an aromatic with an olefin, for example in the production of cumene or ethylbenzene, the sieve catalyst shows favorable selectivity.Type: GrantFiled: December 30, 1993Date of Patent: July 18, 1995Assignee: UOPInventors: Gregory J. Gajda, Robert L. Patton, Stephen T. Wilson
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Patent number: 5243115Abstract: Aromatic compounds are alkylated in a catalytic distillation, wherein the catalyst structure also serves as a distillation component by contacting the aromatic compound with a C.sub.2 to C.sub.10 olefin in the catalyst bed under 0.25 to 50 atmospheres of pressure and at temperatures in the range of 80.degree. C. to 500.degree. C., using as the catalyst a mole sieve characterized as acidic or an acidic cation exchange resin. For example, ethyl benzene is produced by feeding ethylene to about the mid point of the catalyst bed while benzene is conveniently added through the reflux in molar excess to that required to react with ethylene, thereby reacting substantially all of the ethylene and recovering benzene as the principal overhead and ethyl benzene in the bottoms.Type: GrantFiled: April 22, 1991Date of Patent: September 7, 1993Assignee: Chemical Research & Licensing CompanyInventors: Lawrence A. Smith, Jr., Robert P. Arganbright, Dennis Hearn
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Patent number: 5110778Abstract: Boron, aluminum and gallium C.sub.1 -C.sub.18 perfluoroalkane-sulfonates (CF.sub.3 (CF.sub.2).sub.n SO.sub.3).sub.3 M (M=B, A1, Ga; n=0-17) as well as perfluororesin sulfonates such as Nafionates are new, highly effective Friedel-Crafts catalysts. In contrast to volatile aluminum and boron trihalides, the Group III-B perfluoroalkanesulfonates are generally of low or no volatility and, except for boron triflate and some of its homologs, only sparingly soluble incommon organic solvents. This allows their use as solid or supported Friedel-Crafts catalysts of wide utility and scope in continuous heterogenous catalytic processes. At the same time, boron triflate and related lower perfluoroalkanesulfonates are particularly efficient soluble catalysts in solution reactions.Type: GrantFiled: October 23, 1987Date of Patent: May 5, 1992Inventor: George A. Olah
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Patent number: 5105047Abstract: Improved processes for acid-catalyzed oligomerization of olefins and alkylation of toluene are disclosed using a catalyst blend of at least one perfluorinated ion-exchange polymer containing sulfonic acid groups and at least one polymer diluent in a nonpolar reaction mixture.Type: GrantFiled: August 2, 1989Date of Patent: April 14, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventor: Francis J. Waller
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Patent number: 5105042Abstract: There is provided a sulfated layered titanium oxide catalyst. Relatively long chain alkyl aromatic compounds are prepared by alkylating an alkylatable aromatic compound with a relatively long chain alkylating agent under alkylation reaction conditions in the presence of this sulfated layered material as alkylation catalyst. The layered material contains titanium oxide in the layers and oxide pillars separating the layers. The alkylation activity of the catalyst is increased by including sulfate ions in the layered material. This increased alkylation activity may be obtained by contacting the layered material with an aqueous solution of a sulfate compound such as sulfuric acid.Type: GrantFiled: November 21, 1990Date of Patent: April 14, 1992Assignee: Mobil Oil Corp.Inventors: Brent A. Aufdembrink, Charles T. Kresge, Quang N. Le, Joosup Shim, Stephen S. Wong
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Patent number: 5097061Abstract: A method for preparing .alpha.-(4-isobutylphenyl)propionic acid or its precursor is here disclosed which comprises a step A of forming p-isobutylstyrene from p-isobutylethylbenzene and a step B of forming .alpha.-(4-isobutylphenyl)propionaldehyde from p-isobutylstyrene or a step C of forming .alpha.-(4-isobutylphenyl)propionic acid or its alkyl ester from p-isobutylstyrene.Furthermore, a method for preparing said p-isobutylethylbenzene is also disclosed which comprises alkylating isobutylbenzene or 4-ethyltoluene with ethylene or propylene.Type: GrantFiled: June 19, 1989Date of Patent: March 17, 1992Assignee: Nippon Petrochemicals Co., Ltd.Inventors: Isoo Shimizu, Yasuo Matsumura, Yuuichi Tokumoto, Kazumichi Uchida
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Patent number: 5043510Abstract: This invention relates to a process for alkylation at carbon and phosphorus sites in an aqueous medium using precious metal catalysts containing sulfonated triarylphosphines (STP) of the generic formula P(C.sub.6 H.sub.4 SO.sub.3 --)X(C.sub.6 H.sub.5)Y (X+Y=3).Type: GrantFiled: March 27, 1989Date of Patent: August 27, 1991Assignee: E. I. Du Pont de Nemours and CompanyInventors: Albert L. Casalnuovo, William A. Nugent, Jr.
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Patent number: 5034562Abstract: An acid-sulfolane catalyzed process of preparing cyclic alkylated compounds such as indanes by reacting a monovinyl aromatic compound with an olefinic compound, such reaction further improved by the addition of a lanthanide oxide, or Group VI A elements and/or oxides or a mixture of such oxides.Type: GrantFiled: June 8, 1990Date of Patent: July 23, 1991Assignee: Phillips Petroleum CompanyInventor: Raymond L. Cobb
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Patent number: 4990716Abstract: Diphenylmethanes such as o-benzyltoluene are prepared by contacting a benzyl halide with a benzene in the presence of a catalytic amount of a normally solid, insoluble perfluorosulfonic acid polymer under reaction conditions. The o-benzyltoluenes are useful intermediates in the production of anthraquinone and anthracene.Type: GrantFiled: June 9, 1989Date of Patent: February 5, 1991Assignee: The Dow Chemical CompanyInventors: Gregory F. Schmidt, Paul D. Williams
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Patent number: 4967034Abstract: The invention relates to a process for the vapor phase alkylation of alkanes or aromatic hydrocarbons comprising (a) adsorbing an alkene on a dry cation exchange resin in its hydrogen form and (b) reacting said adsorbed alkene with at least one alkane or at least one aromatic hydrocarbon.Type: GrantFiled: August 16, 1989Date of Patent: October 30, 1990Assignee: Energia Andina Ltd.Inventors: Jorge P. Miller, Miguel F. Kling
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Patent number: 4912278Abstract: Compositions containing sulfuric acid and one or more of certain chalcogen-containing compounds in which the chalcogen compound/H.sub.2 SO.sub.4 molar ratio is below 2 contain the mono-adduct of sulfuric acid which is catalytically active for promoting organic chemical reactions. Suitable chalcogen-containing compounds have the empirical formula ##STR1## wherein X is a chalcogen, each of R.sub.1 and R.sub.2 is independently selected from hydrogen, NR.sub.3 R.sub.4, and NR.sub.5, at least one of R.sub.1 and R.sub.2 is other than hydrogen, each of R.sub.3 and R.sub.4 is hydrogen or a monovalent organic radical, and R.sub.5 is a divalent organic radical. Such compositions are useful for catalyzing organic reactions such as oxidation, oxidative addition, reduction, reductive addition, esterification, transesterification, hydrogenation, isomerication (including racemization of optical isomers), alkylation, polymerization, demetallization of organometallics, nitration, Friedel-Crafts reactions, and hydrolysis.Type: GrantFiled: January 29, 1988Date of Patent: March 27, 1990Assignee: Union Oil Company of CaliforniaInventor: Donald C. Young
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Patent number: 4885425Abstract: Compositions containing sulfuric acid and one or more of certain chalcogen-containing compounds in which the chalcogen compound/H.sub.2 SO.sub.4 molar ratio is below 2 contain the mono-adduct of sulfuric acid which is catalytically active for promoting organic chemical reactions. Suitable chalcogen-containing compounds have the empirical formula ##STR1## wherein X is a chalcogen, each of R.sub.1 and R.sub.2 is independently selected from hydrogen, HR.sub.3 R.sub.4, and NR.sub.5, at least one of R.sub.1 and R.sub.2 is other than hydrogen, each of R.sub.3 and R.sub.4 is hydrogen or a monovalent organic radical, and R.sub.5 is a divalent organic radical. Such compositions are useful for catalyzing organic reactions such as oxidation, oxidative addition, reduction, reductive addition, esterification, transesterification, hydrogenation, isomerication (including racemization of optical isomers), alkylation, polymerization, demetallization of organometallics, nitration, Friedel-Crafts reactions, and hydrolysis.Type: GrantFiled: January 29, 1988Date of Patent: December 5, 1989Assignee: Union Oil Company of CaliforniaInventor: Donald C. Young
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Patent number: 4849569Abstract: Aromatic compounds are alkylated in a catalytic distillation, wherein the catalyst structure also serves as a distillation component by contacting the aromatic compound with a C.sub.2 to C.sub.10 olefin in the catalyst bed under 0.25 to 50 atmospheres of pressure and at temperatures in the range of 80.degree. C. to 500.degree. C., using as the catalyst a mole sieve characterized as acidic or an acidic cation exchange resin. For example, ethyl benzene is produced by feeding ethylene below the catalyst bed while benzene is conveniently added through the reflux in molar excess to that required to react with ethylene, thereby reacting substantially all of the ethylene and recovering benzene as the principal overhead and ethyl benzene in the bottoms.Type: GrantFiled: October 17, 1988Date of Patent: July 18, 1989Assignee: Chemical Research & Licensing CompanyInventor: Lawrence A. Smith, Jr.
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Patent number: 4800186Abstract: A method of regenerating a deactivated fluorocarbonsulfonic acid polymer catalyst by contacting the deactivated catalyst with a solvent combination wherein a first solvent swells the structure of the polymer and the other acts as a diluent to modify the swelling action of the first. The combination dissolves the deactivating components.Type: GrantFiled: October 28, 1987Date of Patent: January 24, 1989Assignee: The Dow Chemical CompanyInventor: Emmett L. Tasset
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Patent number: 4673769Abstract: This invention provides a catalyst product for hydrocarbon conversion reactions and a method for reacting hydrocarbons employing such catalyst product. The catalyst product is a composite of a perfluorinated polymersulfonic acid and an ion-stabilizing agent such as hexafluoroisopropanol or trifluoroacetic acid. The composite catalyst has a significantly higher Bronsted acidity than the perfluorinated polymersulfonic acid. When the catalyst composite is used to catalyze the alkylation of toluene with 1-hexene, for example, the rate of alkylation is from about 20 to 30 times greater than using the perfluorinated polymersulfonic acid alone.Type: GrantFiled: December 13, 1985Date of Patent: June 16, 1987Assignee: Exxon Research and Engineering CompanyInventor: Dan Farcasiu
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Patent number: 4650918Abstract: Hydrocarbon alkylation processes which are catalyzed by acids are promoted by the addition of an alkylation promoter which is a combination of a new carboxylic acid having the structural formula ##STR1## wherein R, R.sup.1 and R.sup.2 are alkyl groups and at least one aromatic hydrocarbon sulfonic acid selected from compounds having the structure ##STR2## wherein R.sup.3 is H or an alkyl group and R.sup.4 is an alkyl group.Type: GrantFiled: November 25, 1985Date of Patent: March 17, 1987Assignee: Atlantic Richfield CompanyInventors: Richard F. Miller, Marilyn W. Blaschke
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Patent number: 4613723Abstract: The present invention relates to supported superacidic catalysts comprising C.sub.4 -C.sub.18, preferentially C.sub.6 to C.sub.12, perfluorinated alkanesulfonic acid absorbed on suitable supports, such as fluoridated alumina, alumina silica and other chalcides having bonded thereto subsequently a Lewis acid compound selected from the higher valency fluorides of the elements of Groups IIA, IIIA, IVB, VA or VIB of the Periodic Table. The invention includes a process for catalytic transformation of hydrocarbons.Type: GrantFiled: January 3, 1984Date of Patent: September 23, 1986Assignee: PCUK-Produits Chimiques Ugine KuhlmannInventor: George A. Olah
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Patent number: 4547474Abstract: The present invention relates to supported superacidic catalysts comprising C.sub.4 -C.sub.18, preferentially C.sub.6 to C.sub.12, perfluorinated alkanesulfonic acid absorbed on suitable supports, such as fluorinated alumina, alumina silica and other chalcides having bonded thereto subsequently a Lewis acid compound selected from the higher valency fluorides of the elements of Groups IIA, IIIA, IVB, VA or VIB of the Periodic Table. The invention includes a process for catalytic transformation of hydrocarbons.Type: GrantFiled: January 3, 1984Date of Patent: October 15, 1985Assignee: AtochemInventor: George A. Olah
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Patent number: 4547604Abstract: Resorcinol is prepared in high yield and purity by an improved process through superacid (such as perfluorinated alkanesulfonic acids of one to eighteen carbon atoms or polymeric perfluorinated resinsulfonic acids, such as acidified Nafion-H, catalyzed cleavage rearrangement reaction of meta-bis(2-hydroperoxy-2-propyl)benzene (meta-diisopropylbenzene dihydroperoxide). Part of the process is the preparation of needed meta-diisopropylbenzene in high purity (98-100%) substantially free of other isomers by treating any mixture of diisopropylbenzenes with an excess of anhydrous hydrogen fluoride or a perfluorinated alkanesulfonic acid of one to eighteen carbon atoms and a Lewis acid fluoride, or by alkylating (transalkylating) cumene with a propyl alkylating agent in the aforementioned superacid systems.Type: GrantFiled: February 6, 1984Date of Patent: October 15, 1985Assignee: PCUK Produits Chimiques Ugine KuhlmannInventor: George A. Olah
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Patent number: 4480142Abstract: The alkylation of aromatic compounds with olefins can be conducted more efficiently in the presence of certain catalysts.Type: GrantFiled: November 4, 1982Date of Patent: October 30, 1984Assignee: Phillips Petroleum CompanyInventor: Raymond L. Cobb
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Patent number: 4446329Abstract: Improved catalytic process for the alkylation of aromatic substrates, the improved process characterized in that the catalyst is a metal cation salt of a perfluorosulfonic acid polymer having an equivalent weight of about 500 to about 20,000, the metal cation having a log K.sub.11 greater than -10.Type: GrantFiled: March 24, 1983Date of Patent: May 1, 1984Assignee: E. I. Du Pont de Nemours & CompanyInventor: Francis J. Waller
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Patent number: 4317949Abstract: This invention relates to conversion processes which take place in the presence of solid acid catalysts, e.g., hydrocarbon conversion processes. More specifically, this invention relates to a process for the alkylation of organic compounds, preferably aromatic and paraffinic hydrocarbons, with alkylating agents, e.g., alkyl chlorides, alkyl sulfonates, alkyl epoxides, alkynes, etc., in the presence of a polyfluorosulfonic acid catalyst.Type: GrantFiled: February 23, 1976Date of Patent: March 2, 1982Assignee: Varen TechnologyInventor: Ronald J. Vaughan
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Patent number: 4288646Abstract: A process for the production of .beta.-isopropylnaphthalene in high regioselectivity (90-98%) by alkylation of naphthalene over solid or supported superacid catalysts, such as a perfluorinated alkanesulfonic acid of four to eighteen carbon atoms (C.sub.4 F.sub.9 SO.sub.3 H to C.sub.18 F.sub.37 SO.sub.3 H) or a polymeric perfluorinated resin-sulfonic acid, such as the acid form of the commercially available Nafion-K ion-membrane resin (DuPont). Further isomerization of mixtures of isomeric isopropylnaphthalenes to preferentially pure .beta.-isopropylnaphthalene can also be effected.Type: GrantFiled: October 5, 1979Date of Patent: September 8, 1981Assignee: PCUK Produits Chimiques Ugine KuhlmannInventor: George A. Olah
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Patent number: 4287376Abstract: A method for aralkylation of benzene or alkylbenzenes which is characterized in that an aromatic olefin having a double bond or double bonds which are conjugated with the benzene ring is added to the benzene or alkylbenzenes in the presence of at least one member of catalyst selected from the group consisting of the compounds represented by the general formula:C.sub.n F.sub.2n+1-m Cl.sub.m SO.sub.3 Hin which the symbol n is an integer from 1 to 5 and m is 0 or 1. Since the selectivity to the aromatic olefin in the reaction is excellent, the mixture of aromatic olefins and aliphatic olefins can be employed as one of the starting material.Type: GrantFiled: July 25, 1979Date of Patent: September 1, 1981Assignee: Nippon Petrochemicals Co., Ltd.Inventors: Isoo Shimizu, Okitsugu Tsuji, Eiichi Matsuzaka, Atsushi Sato
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Patent number: 4255343Abstract: Process for preparing 2-t-alkylanthracene, which process comprises contacting and reacting, with good mixing, at a temperature of at least 110.degree. C., anthracene and a branched-chain alkylating agent, the alkylating moiety of which contains at least four carbon atoms, in the presence of a catalyst selected from hydrocarbonsulfonic acids which are free of nonaromatic unsaturation, organic carboxylic acids having a K.sub.a of 0.6 to 0.001, acid zeolites, amorphous silica-aluminas, and polymeric arenesulfonic acid resins, to give a product mixture of which the major constituent is 2-t-alkylanthracene.Type: GrantFiled: August 13, 1979Date of Patent: March 10, 1981Assignee: E. I. Du Pont de Nemours and CompanyInventor: Lawrence W. Gosser