Using Organometallic Compound Catalyst Patents (Class 585/457)
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Patent number: 9079289Abstract: The purpose of the present invention is to provide: a polishing pad which has improved dressing properties, while maintaining the hardness; or a polishing pad which does not easily make a scratch on the surface of an object to be polished, while having improved dressing properties. A polishing pad of the present invention is characterized by having a polishing layer that is formed of a polyurethane resin foam or an unfoamed polyurethane resin, and is also characterized in that the polyurethane resin foam or the unfoamed polyurethane resin contains, as starting material components, (A) an isocyanate component, (B) a polyol component and (C) an aromatic compound that has one hydroxyl group and/or an aromatic compound that has one amino group.Type: GrantFiled: August 24, 2012Date of Patent: July 14, 2015Assignee: TOYO TIRE & RUBBER CO., LTD.Inventors: Akinori Sato, Masato Doura
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Patent number: 8841500Abstract: Provided is a process for preparing alkyl aromatic compounds. The process comprises contacting an alkane under dehydrogenation conditions in the presence of a dehydrogenation catalyst, e.g., a pincer iridium catalyst, to form olefins, and then contacting the olefins generated with an aromatic compound under alkylation conditions. Both reactions are conducted in a single reactor, and occur simultaneously.Type: GrantFiled: September 12, 2012Date of Patent: September 23, 2014Assignees: Chevron U.S.A. Inc., Rutgers, The State University of New JerseyInventors: Alan Stuart Goldman, Long Van Dinh, William L. Schinski
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Publication number: 20140249343Abstract: Disclosed is a process for the direct alkylation of aromatic compounds with alkanes. To this end a judicious catalyst combination is provided. The composition comprises palladium as a catalytically active metal, and zinc as a promoter, or a metal such as tin having a comparable promoting action. The metals are contained in a zeolite support, or a similar support of a metal organic framework type or a silico alumino phosphate type.Type: ApplicationFiled: June 28, 2012Publication date: September 4, 2014Applicant: UNIVERSITÄT STUTTGARTInventors: Yvonne Traa, Daniel Geiss
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Publication number: 20140194661Abstract: A new family of coherently grown composites of TUN and IMF zeotypes has been synthesized and shown to be effective catalysts for aromatic transformation reactions. These zeolites are represented by the empirical formula: NanMmk+TtAl1-xExSiyOz where “n” is the mole ratio of Na to (Al+E), M represents at least one meta, “m” is the mole ratio of M to (Al+E), “k” is the average charge of the metal or metals M, T is the organic structure directing agent or agents, “t” is the mole ratio of N from the organic structure directing agent or agents to (Al+E), and E is a framework element such as gallium. The process involves contacting at least a first aromatic with the coherently grown composites of TUN and IMF zeotypes to produce at least a second aromatic.Type: ApplicationFiled: December 9, 2013Publication date: July 10, 2014Applicant: UOP LLCInventors: Christopher P. Nicholas, Mark A. Miller, Antoine Negiz
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Publication number: 20140004024Abstract: A new family of crystalline microporous metallophosphates designated AlPO-57 has been synthesized. These metallophosphates are represented by the empirical formula R+rMmn+EPxSiyOz where R is an organoammonium cation such as the DEDMA+, M is a divalent framework metal such as an alkaline earth or transition metal, and E is a framework element such as aluminum or gallium. The microporous AlPO-57 compositions are characterized by a new unique ABC-6 net structure and have catalytic properties for carrying out various hydrocarbon conversion processes and separation properties for separating at least one component.Type: ApplicationFiled: June 29, 2012Publication date: January 2, 2014Applicant: UOP LLCInventors: Gregory J. Lewis, Lisa M. Knight, Paulina Jakubczak, Justin E. Stanczyk
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Patent number: 8536394Abstract: According to a process of the invention, a ketone, an aromatic compound and hydrogen as starting materials are reacted together in a single reaction step to produce an alkylaromatic compound in high yield. A process for producing phenols in the invention includes a step of performing the above alkylation process and does not increase the number of steps compared to the conventional cumene process. The process for producing alkylated aromatic compounds includes reacting an aromatic compound such as benzene, a ketone such as acetone and hydrogen in the presence of a solid acid substance, preferably a zeolite, and a silver-containing catalyst.Type: GrantFiled: March 12, 2010Date of Patent: September 17, 2013Assignee: Mitsui Chemicals, Inc.Inventors: Tsuneyuki Ohkubo, Shinobu Aoki, Masayasu Ishibashi, Masao Imai, Terunori Fujita, Kenji Fujiwara
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Patent number: 8507396Abstract: A process for regenerating a used acidic catalyst which has been deactivated by conjunct polymers by removing the conjunct polymers so as to increase the activity of the catalyst is disclosed. Methods for removing the conjunct polymers include addition of a basic reagent and alkylation. The methods are applicable to all acidic catalysts and are described with reference to certain ionic liquid catalysts.Type: GrantFiled: April 20, 2010Date of Patent: August 13, 2013Assignee: Chevron U.S.A. Inc.Inventors: Saleh Elomari, Thomas V. Harris
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Publication number: 20130165726Abstract: A new family of coherently grown composites of TUN and IMF zeotypes has been synthesized and shown to be effective catalysts for aromatic transformation reactions. These zeolites are represented by the empirical formula. NanMmk+TtAl1-xExSiyOz where “n” is the mole ratio of Na to (Al+E), M represents at least one meta, “m” is the mole ratio of M to (Al+E), “k” is the average charge of the metal or metals M, T is the organic structure directing agent or agents, “t” is the mole ratio of N from the organic structure directing agent or agents to (Al+E), and E is a framework element such as gallium. The process involves contacting at least a first aromatic with the coherently grown composites of TUN and IMF zeotypes to produce at least a second aromatic.Type: ApplicationFiled: December 14, 2012Publication date: June 27, 2013Applicant: UOP LLCInventor: UOP LLC
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Publication number: 20130165720Abstract: A new family of coherently grown composites of TUN and IMF zeotypes have been synthesized. These zeolites are represented by the empirical formula. NanMmk+TtAl1-xExSiyOz where “n” is the mole ratio of Na to (Al+E), M represents a metal or metals from zinc, Group 1, Group 2, Group 3 and or the lanthanide series of the periodic table, “m” is the mole ratio of M to (Al+E), “k” is the average charge of the metal or metals M, T is the organic structure directing agent or agents, and E is a framework element such as gallium. These zeolites are similar to TNU-9 and IM-5 but are characterized by unique compositions and synthesis procedures and have catalytic properties for carrying out various hydrocarbon conversion processes and separation properties for carrying out various separations.Type: ApplicationFiled: December 14, 2012Publication date: June 27, 2013Applicant: UOP LLCInventor: UOP LLC
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Patent number: 8288604Abstract: A method of rapid methylation of an aromatic compound or an alkenyl compound, which is capable of obtaining an aromatic compound or an alkenyl compound labeled with a methyl group or a fluoromethyl group under a mild condition rapidly in high yield using an organic boron compound whose toxicity is not so high as a substrate. A kit for preparing a PET tracer and a method of producing a PET tracer can be practiced using the rapid methylation method. In an aprotic polar solvent, methyl iodide or X—CH2F (wherein X is a functional group which can be easily released as an anion), and an organic boron compound in which an aromatic ring or an alkenyl group is attached to boron are subjected to cross-coupling in the presence of a palladium(0) complex, a phosphine ligand, and a base.Type: GrantFiled: August 24, 2007Date of Patent: October 16, 2012Assignees: Gifu University, Riken, Hamamatsu Photonics K.K.Inventors: Masaaki Suzuki, Hisashi Doi, Hideo Tsukada
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Patent number: 8237002Abstract: A method for producing an unsaturated organic compound represented by the formula (3): (Y1)m-1—R1—R2—(Y2)n-1??(3) wherein Y1 represents R2 or X1, and Y2 represents R1 or B(X2)2, which comprises reacting a compound represented by the formula (1): R1(X1)m??(1) wherein R1 represents an aromatic group or the like, X1 represents a leaving group and m represents 1 or 2, with a compound represented by the formula (2): R2{B(X2)2}n??(2) wherein R2 represents an aromatic group or the like, X2 represents a hydroxyl group or the like, and n represents 1 or 2, in the presence of (a) a nickel compound selected from a nickel carboxylate, nickel nitrate and a nickel halide, (b) a phosphine compound such as 1,4-bis(dicyclohexylphosphino) butane, (c) an amine selected from a primary amine and a diamine such as N,N,N?,N?-tetramethyl-1,2-ethanediamine, and (d) an inorganic base.Type: GrantFiled: April 28, 2009Date of Patent: August 7, 2012Assignee: Sumitomo Chemical Company, LimitedInventors: Taku Asaumi, Takashi Kamikawa
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Publication number: 20120004485Abstract: A method for preparing a family of zeolites, examples of which have been designated UZM-5, UZM-5P and UZM-6, and are represented by the empirical formula Mmn+Cgh+Rrp+Al(1-x)ExSiyOz The method includes forming a Charge Density Mismatch (CDM) reaction mixture comprising reactive sources of Al, Si, optionally a framework element, E, and at least one organic nitrogen containing cation template, C, in the hydroxide form. After the CDM mixture is mixed while aging, an organic cation crystallization template, R, and at least one alkali metal or alkaline earth metal, M, is added. The combined final reaction mixture is reacted with mixing to produce the zeolite, which may be used in various hydrocarbon conversion processes.Type: ApplicationFiled: June 29, 2011Publication date: January 5, 2012Applicant: UOP LLCInventors: Deng-Yang Jan, Jaime G, Moscoso, Raelynn M. Miller, Susan C. Koster, Julio C. Marte
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Patent number: 8030508Abstract: The present invention relates to an organosilicon porous zeolite, preparation of the same, and use of the same. The organosilicon porous zeolite of the invention has the following composition on molar basis: (1/n)Al2O3:SiO(2-m/2):mR:xM, wherein n=5 to 1000, m=0.001 to 1, x=0.005 to 2, R is at least one selected from the group consisting of alkyl, alkenyl and phenyl and connected to a silicon atom in the framework of the zeolite, and M is an organic amine templating agent, wherein a solid Si29NMR spectrum of the zeolite has at least one Si29 nuclear magnetic resonance peak in the range of from ?80 to +50 ppm, and wherein a X-ray diffraction pattern of the zeolite exhibits diffraction peaks corresponding to d-spacing of 12.4±0.2, 11.0±0.3, 9.3±0.3, 6.8±0.2, 6.1±0.2, 5.5±0.2, 4.4±0.2, 4.0±0.2 and 3.4±0.1 ?. The porous zeolite can be used as an adsorbent or as a component of a catalyst for the conversion of an organic compound.Type: GrantFiled: July 17, 2007Date of Patent: October 4, 2011Assignees: China Petroleum & Chemical Corporation, Shanghai Research Institute Of Petrochemical Technology SinopecInventors: Huanxin Gao, Bin Zhou, Yilun Wei, Hua Fang, Ruifang Gu, Shufang Ji
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Patent number: 7910783Abstract: A process for preparing a chelating ligand of the formula (II) from a chelating ligand of the formula (I) via an sp2-sp2 or sp2-sp3 coupling reaction with an organometallic compound of the formula (III).Type: GrantFiled: December 14, 2005Date of Patent: March 22, 2011Assignee: ExxonMobil Chemical Patents Inc.Inventors: Alexander Z. Voskoboynikov, Mikhail V. Nikulin, Alexey N. Ryabov, Alexander V. Lygin, Catalina L. Coker, Jo Ann M. Canich
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Publication number: 20100331594Abstract: Alkylation processes such as the alkylation of aromatics, are catalyzed by the UZM-35 family of crystalline aluminosilicate zeolites represented by the empirical formula: Mmn+Rr+Al(1?x)ExSiyOz where M represents a combination of potassium and sodium exchangeable cations, R is a singly charged organoammonium cation such as the dimethyldipropylammonium cation and E is a framework element such as gallium. These UZM-35 zeolites are active and selective in alkylation processes.Type: ApplicationFiled: June 29, 2009Publication date: December 30, 2010Inventors: CHRISTOPHER P. NICHOLAS, Deng-Yang Jan, Jaime G. Moscoso
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Publication number: 20100184941Abstract: This invention provides adducts, mixtures of adducts and oligomers, and/or mixtures of adducts, oligomers, and low molecular weight polymers formed from monovinylaromatic hydrocarbons.Type: ApplicationFiled: June 6, 2008Publication date: July 22, 2010Applicant: ALBEMARLE CORPORATIONInventors: William J. Layman, JR., Arthur G. Mack, Charles H. Kolich
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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: 7605294Abstract: Methods for the preparation of fluorenyl-type ligand structures and substituted fluorenyl groups which may be employed in metallocene-type olefin polymerization catalysts. There is provided a 2,2?-dihalogen-diphenylmethylene having a methylene bridge connecting a pair of phenyl groups. Each phenyl group has a halogen on a proximal carbon atom relative to the methylene bridge. The halogenated diphenylmethylene is reacted with a coupling agent comprising a Group 2 or 12 transition metal in the presence of a nickel or palladium-based catalyst to remove the halogen atoms from the phenyl groups and couple the phenyl groups at the proximal carbon atoms to produce a fluorene ligand structure. The coupling agent may be zinc, cadmium or magnesium and the catalyst may be a monophosphene nickel complex. The halogenated diphenylmethylene may be an unsubstituted ligand structure or a monosubstituted or disubstituted ligand structure.Type: GrantFiled: November 25, 2008Date of Patent: October 20, 2009Assignee: Fina Technology, Inc.Inventors: Vladimir Marin, Abbas Razavi
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Publication number: 20090247776Abstract: The present invention relates to an organosilicon porous zeolite, preparation of the same, and use of the same. The organosilicon porous zeolite of the invention has the following composition on molar basis: (1/n)Al2O3:SiO(2-m/2):mR:xM, wherein n=5 to 1000, m=0.001 to 1, x=0.005 to 2, R is at least one selected from the group consisting of alkyl, alkenyl and phenyl and connected to a silicon atom in the framework of the zeolite, and M is an organic amine templating agent, wherein a solid Si29NMR spectrum of the zeolite has at least one Si29 nuclear magnetic resonance peak in the range of from ?80 to +50 ppm, and wherein a X-ray diffraction pattern of the zeolite exhibits diffraction peaks corresponding to d-spacing of 12.4±0.2, 11.0±0.3, 9.3±0.3, 6.8±0.2, 6.1±0.2, 5.5±0.2, 4.4±0.2, 4.0±0.2 and 3.4±0.1 ?. The porous zeolite can be used as an adsorbent or as a component of a catalyst for the conversion of an organic compound.Type: ApplicationFiled: July 17, 2007Publication date: October 1, 2009Applicants: China Petroleum & Chemical Corporation, Shanghai Research Institute Of Petrochemical Technology SinopecInventors: Huanxin Gao, Bin Zhou, Yilun Wei, Hua Fang, Ruifang Gu, Shufang Ji
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Patent number: 7473813Abstract: Methods for the preparation of fluorenyl-type ligand structures and substituted fluorenyl groups which may be employed in metallocene-type olefin polymerization catalysts. There is provided a 2,2?-dihalogen-diphenylmethylene having a methylene bridge connecting a pair of phenyl groups. Each phenyl group has a halogen on a proximal carbon atom relative to the methylene bridge. The halogenated diphenylmethylene is reacted with a coupling agent comprising a Group 2 or 12 transition metal in the presence of a nickel or palladium-based catalyst to remove the halogen atoms from the phenyl groups and couple the phenyl groups at the proximal carbon atoms to produce a fluorene ligand structure. The coupling agent may be zinc, cadmium or magnesium and the catalyst may be a monophosphene nickel complex. The halogenated diphenylmethylene may be an unsubstituted ligand structure or a monosubstituted or disubstituted ligand structure.Type: GrantFiled: June 29, 2006Date of Patent: January 6, 2009Assignee: Fina Technology, Inc.Inventors: Vladimir Marin, Abbas Razavi
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Patent number: 7282617Abstract: A process for making medium and long chain alkylaromatics and alkylphenols having a high level of anti-Markovnikov addition of the alkyl group. The alkylaromatics and alkylphenols made by the process of the present invention have enhanced stability and are particularly well suited to make highly stable oil additives and enhanced oil recovery surfactants.Type: GrantFiled: March 31, 2006Date of Patent: October 16, 2007Assignee: Chevron U.S.A. Inc.Inventors: William L. Schinski, Curt B. Campbell
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Patent number: 7141687Abstract: The invention relates to N?-substituted N-acylamidine transition metal complexes of the general formula (I), wherein M represents a transition metal, selected from the group of metals including Ni, Cu, Ru, Rh, Pd, Os, Ir and Pt, X represents Cl, Br, triflate, methane sulfonate or p-toluol sulfonate, m is 0, 1 or 2, n is 1, 2 or 3 and the radicals have the following meanings: R1, R2 is a straight-chain or branched, cyclic hydrocarbon group with 1 to 20 carbon atoms which can be mono or poly-unsaturated, an aromatic group with 3 to 6 chain members, which is linked directly or via a C1 to C6 alkyl or C2 to C6 alkylene group, whereby the mentioned groups can carry one or more substituents. Ar represents C6 to C10 aryl or hetaryl with 5 to 10 ring members, whereby the mentioned groups can be substituted by C1 to C6 alkyl, C1 to C4 halogenalkyl, NR10R11, COOR6, Si(R7)3Si(R7)2R8, OR3 and/or halogen.Type: GrantFiled: November 28, 2003Date of Patent: November 28, 2006Assignee: BASF AktiengesellschaftInventors: Jan Kurt Eberhardt, Ernst-Ulrich Würthwein
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Patent number: 7094941Abstract: A repeated “soak and dry” selectivation process for preparing a modified metallosilicate catalyst composite is disclosed comprising of a mixture of amorphous silica, alumina and a pore size controlled metallosilicate useful for alkylaromatic conversion. The process comprises (a) contacting an intermediate pore metallosilicate with an organosilicon compound in a solvent for a specific duration and then recovering the solvent, (b) combining the organosilicon compound treated metallosilicate with water and then drying the catalyst, (c), repeating the steps a) and b) above and (d) calcining the catalyst in an oxygen containing atmosphere sufficient to remove the organic material and deposit siliceous matter on the metallosilicate. In a another embodiment, when the organosilicon compound is water soluble, step (b) may be avoided.Type: GrantFiled: December 14, 2002Date of Patent: August 22, 2006Assignee: Indian Petrochemicals Corp., Ltd.Inventors: Jagannath Das, Anand Bhimrao Halgeri
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Patent number: 6723870Abstract: Disclosed is a method for producing anthracene of formula (II) below by mixing a reaction mixture with a primary alcohol, wherein the reaction mixture is a reaction mixture obtained by reacting a metal hydride with an anthraquinone of formula (I):Type: GrantFiled: September 24, 2002Date of Patent: April 20, 2004Assignee: Sumitomo Chemical Company, LimitedInventors: Takashi Kamikawa, Junji Morimoto
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Patent number: 6686495Abstract: A process for the preparation of mono-, bi- or poly-functional biaryls in the presence of a metal complex of the general formula IV as catalyst.Type: GrantFiled: October 16, 2001Date of Patent: February 3, 2004Assignee: OMG AG & Co KGInventors: Matthias Beller, Mario Gómez-Andreu, Alexander Zapf, Ralf Karch, Ingo Kleinwächter, Oliver Briel
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Patent number: 6566571Abstract: Process for preparing monofunctional, bifunctional and/or polyfunctional biaryls of the formula (I) Ar—Ar′ (I) by reacting haloaromatics of the formula (II) Ar—X (II) with boron compounds of the formula (IIIa), (IIIb) and/or (IIIc) in the presence of at least one palladium complex of the formula (IVa) or (IVb)Type: GrantFiled: February 4, 2002Date of Patent: May 20, 2003Assignee: Degussa AGInventors: Thomas Riermeier, Matthias Beller, Alexander Zapf
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Patent number: 6504070Abstract: A method of preparing an alkyl-substituted aromatic hydrocarbon, which comprises alkylating an aromatic hydrocarbon with an olefin in the presence of a catalyst comprising an iridium compound having at least one iridium atom and at least one &bgr;-diketonato ligand to produce the alkyl-substituted aromatic hydrocarbon.Type: GrantFiled: February 2, 2001Date of Patent: January 7, 2003Assignee: Nippon Mitsubishi Oil CorporationInventors: Takaya Matsumoto, Douglas Taube, Roy Anthony Periana
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Patent number: 6462246Abstract: A method of preparing an alkenyl-substituted aromatic hydrocarbon, which comprises alkenylating an aromatic hydrocarbon with an olefin using &bgr;-diketone together with a rhodium complex catalyst in the presence of oxygen.Type: GrantFiled: March 29, 2001Date of Patent: October 8, 2002Assignee: Nippon Mitsubishi Oil CorporationInventors: Takaya Matsumoto, Shinji Nishikawa, Hajime Yoshida
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Publication number: 20020107426Abstract: A process for the preparation of mono-, bi- or poly-functional biaryls in the presence of a metal complex of the general formula IV 1Type: ApplicationFiled: October 16, 2001Publication date: August 8, 2002Inventors: Matthias Beller, Mario Gomez-Andreo, Alexander Zapf, Ralf Karch, Ingo Kleinwachter, Oliver Briel
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Publication number: 20020052535Abstract: A method of preparing an alkyl-substituted aromatic hydrocarbon, which comprises alkylating an aromatic hydrocarbon with an olefin in the presence of a catalyst comprising an iridium compound having at least one iridium atom and at least one &bgr;-diketonato ligand to produce the alkyl-substituted aromatic hydrocarbon.Type: ApplicationFiled: February 2, 2001Publication date: May 2, 2002Inventors: Takaya Matsumoto, Douglas Taube, Roy Anthony Periana
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Patent number: 6369265Abstract: This invention provides a process for conducting Kumada coupling reactions. The processes of the present invention make use of N-heterocyclic carbenes as ancillary ligands in Kumada couplings of aryl halides. A Kumada coupling can be carried out by mixing, in a liquid medium, at least one aryl halide, wherein the aryl halide has, directly bonded to the aromatic ring(s), at least one halogen atom selected from the group consisting of a chlorine atom, a bromine atom, and an iodine atom; at least one Grignard reagent; at least one metal compound comprising at least one metal atom selected from nickel, palladium, and platinum, wherein the formal oxidation state of the metal is zero or two; and at least one N-heterocyclic carbene.Type: GrantFiled: February 22, 2000Date of Patent: April 9, 2002Assignee: University of New Orleans Research & Technology FoundationInventors: Steven P. Nolan, Jinkun Huang, Mark L. Trudell, Chunming Zhang
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Patent number: 6316675Abstract: A process for the synthesis of olefins having aromatic substituents is described in which olefins are reacted with aryl halides in the presence of catalysts consisting of palladium compounds and tetraaryl phosphonium salts.Type: GrantFiled: September 23, 1999Date of Patent: November 13, 2001Assignee: Studiengesellschaft Kohle mbHInventors: Manfred T. Reetz, Gunther Lohmer, Renate Lohmer
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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: 6137020Abstract: A process for reducing the amount of undesirable byproducts, for example multi-ring compounds known as heavy residue in a process for the alkylation of an aromatic hydrocarbon with an olefin using a silicalite catalyst is disclosed. The process comprises supplying a feedstock containing benzene to a reaction zone with an alkylating agent in a molar ratio of benzene to alkylating agent of from about 2:1 to about 20:1 and into contact with an aluminosilicate alkylation catalyst having an average crystallite size of less than about 0.50 .mu.m and wherein the size of about 90% of the crystallites is less than 0.70 .mu.m. The catalyst is characterized by an Si/Al atomic ratio in the range from between 50 and 150 and a maximum pore size in the range from about 1000 to 1800 .ANG.. The catalyst has a sodium content of less than about 50 ppm and the reaction is carried out under conversion conditions including a temperature of from about 250.degree. C. to about 550.degree. C.Type: GrantFiled: July 31, 1998Date of Patent: October 24, 2000Assignee: Fina Technology, Inc.Inventors: James R. Butler, Mark E. Kuchenmeister
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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: 6124462Abstract: Phosphine oxide compounds were used with transition metals, preferably palladium, to produce biaryls and arylamines via cross-coupling reactions with aryl halides and arylboronic acids or amines.Type: GrantFiled: November 30, 1999Date of Patent: September 26, 2000Assignee: E. I. du Pont de Nemours and CompanyInventor: George Y. Li
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Patent number: 6100437Abstract: An alkylbenzene is alkylated with an alkene, in the presence of a sodium/potassium alloy catalyst, on a saturated carbon atom which is alpha to the ring at temperatures which are lower than the temperatures used in a current commercial process. In a pre-alkylation reaction, the catalyst is reacted with a compound which has a saturated carbon atom alpha to a double bond in order to form a catalytic species. Higher amounts of catalyst are used in the pre-alkylation reaction than in the analogous reaction of the current commercial process. Following alkylation, the phase which contains the alkylation product is separated from the phase which contains the catalytic species. The process produces less isomeric and other soluble byproducts, and enables the efficacious production of longer chain alkylbenzenes without the formation of insoluble tars characteristic of the current commercial process.Type: GrantFiled: July 10, 1998Date of Patent: August 8, 2000Assignee: Albemarle CorporationInventors: David J. Koehl, Edward A. Burt, Patrick T. Ward
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Patent number: 6040490Abstract: Aromatic hydrocarbons are efficiently converted by bringing feedstock containing from 5 to 50% by weight of an aromatic hydrocarbon having an ethyl group and a C.sub.9 alkyl aromatic hydrocarbon into contact with a catalyst capable of disproportionation, trans-alkylation and dealkylation, a secondary particle diameter of a zeolite in the catalyst being 10 .mu.m or less.Type: GrantFiled: August 12, 1998Date of Patent: March 21, 2000Assignee: Toray Industries, Inc.Inventors: Ryoji Ichioka, Shinobu Yamakawa, Hirohito Okino, Hajime Kato, Kazuyoshi Iwayama, Hiroshi Konta, Akira Kitamura
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Patent number: 6005151Abstract: The invention relates to a process for preparing monofunctional, bifunctional or polyfunctional aromatic olefins of the formula (I) ##STR1## wherein a palladium compound of the formula (IV) ##STR2## is used as a catalyst in the preparation of the compounds of the formula (I).Type: GrantFiled: January 30, 1996Date of Patent: December 21, 1999Assignee: AventisInventors: Wolfgang Anton Herrmann, Matthias Beller, Ahmed Tafesh
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Patent number: 5994602Abstract: This invention relates to a process for the alkylation of aromatics by reacting an aromatic hydrocarbon with an olefin in the presence of an ionic liquid comprising (a) a compound of the formula R.sub.n MX.sub.3-n wherein R is a C1-C6 alkyl radical, M is aluminium or gallium, X is a halogen atom and n is 0, 1 or 2 and, (b) a hydrocarbyl substituted imidazolium halide or a hydrocarbyl substituted pyridinium halide wherein at least one of the said hydrocarbyl substituents in the imidazolium halide is an alkyl group having 1-18 carbon atoms. The process allows ready separation of reaction products from the ionic liquid and improves selectivity to alkylated products.Type: GrantFiled: July 29, 1997Date of Patent: November 30, 1999Assignee: BP Chemicals LimitedInventors: Ala'a K Abdul-Sada, Martin Philip Atkins, Brian Ellis, Philip Kenneth Gordon Hodgson, Mark Louis Michael Morgan, Kenneth Richard Seddon
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Patent number: 5705725Abstract: A process is provided comprising: (a) contacting a hydrocarbyl lithium with an alkali metal hydrocarbyloxide in the presence of an aromatic compound; and thereafter (b) recovering an aromatic alkali metal compound; and thereafter (c) contacting said aromatic alkali metal compound with an alpha-olefin. Optionally, a catalytic support is also present during steps a, b, and c.Type: GrantFiled: October 2, 1991Date of Patent: January 6, 1998Assignee: Phillips Petroleum CompanyInventors: Ted M. Pettijohn, Mark E. Lashier, Henry L. Hsieh
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Patent number: 5672797Abstract: A process for the alkylation of aromatic compounds with an olefin, alcohol, or alkyl halide having from 1 to 24 carbon atoms comprising reacting in the liquid phase the aromatic and alkylating agent under alkylation conditions in the presence of a novel catalyst comprising: a) a refractory inorganic oxide, b) the reaction product of a first metal halide and bound surface hydroxyl groups of the refractory inorganic oxide, c) a second metal cation, and d) optionally a zerovalent third metal. The refractory inorganic oxide is selected from the group consisting of alumina, titania, zirconia, chromia, silica, boria, silica-alumina, and combinations thereof and the first metal halide is a fluoride, chloride, or bromide of aluminum. The second metal cation is selected from the group consisting of: monovalent metal cations in an amount from 0.0026 up to about 0.20 gram atoms per 100 grams refractory inorganic oxide for lithium, potassium, cerium, rubidium, silver, and copper, and from 0.009 to about 0.Type: GrantFiled: September 25, 1995Date of Patent: September 30, 1997Assignee: UOPInventor: Joseph A. Kocal
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Patent number: 5559277Abstract: The invention relates to a process for preparing biphenyls of the formula (I) ##STR1## where R.sup.1a to R.sup.10a are, independently of one another, hydrogen, C.sub.1 -C.sub.12 -alkyl, C.sub.1 -C.sub.12 -alkenyl, C.sub.1 -C.sub.12 -alkynyl, alkoxy-(C.sub.1 -C.sub.12), acyloxy-(C.sub.1 -C.sub.12), O-phenyl, aryl, heteroaryl, fluorine, chlorine, OH, NO.sub.2, CN, COOH, CHO, SO.sub.3 H, SO.sub.2 R, SOR, NH.sub.2, NH-alkyl-(C.sub.1 -C.sub.12), N-alkyl.sub.2 -(C.sub.1 -C.sub.12), C-Hal.sub.3, NHCO-alkyl-(C.sub.1 -C.sub.8), CONH-alkyl-(C.sub.1 -C.sub.4), CON-(alkyl).sub.2 -(C.sub.1 -C.sub.4), COO-alkyl-(C.sub.1 -C.sub.12), CONH.sub.2, CO-alkyl-(C.sub.1 -C.sub.12), NHCOH, NHCOO-alkyl-(C.sub.1 -C.sub.8), CO-phenyl, COO-phenyl, CHCHCO.sub.2 -alkyl-(C.sub.1 -C.sub.12), CHCHCO.sub.2 H, PO-phenyl.sub.2, PO-alkyl.sub.2 -(C.sub.1 -C.sub.8), by reaction of haloaromatics or aryl sulfonates of the formula (II) ##STR2## with arylboron derivatives of the formula III ##STR3## where R.sup.1a to R.sup.Type: GrantFiled: June 29, 1995Date of Patent: September 24, 1996Assignee: Hoechst AGInventors: Matthias Beller, Wolfgang A. Herrmann, Christoph Brossmer
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Patent number: 5436361Abstract: A process for synthesizing enediynes is provided. Specifically, the formed enediynes contain a hex-3-ene-1,5-diynyl group. Production of the enediynes involves adding a base to a propargylic halide in the presence of a chelating agent, which causes a carbenoid coupling-elimination sequence of the propargylic halides. A carbenoid destabilizing agent can also be added to the reaction mixture in order to enhance yield. Acyclic and cyclic enediynes can be synthesized according to this process. The enediynes are useful compounds that can be used in a variety of applications including use in the production of anti-tumor agents.Type: GrantFiled: April 22, 1994Date of Patent: July 25, 1995Assignee: Clemson UniversityInventors: Graham B. Jones, Robert S. Huber
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Patent number: 5227559Abstract: An alkyl-substituted hydrocarbon is prepared by alkylating an aromatic hydrocarbon having at least one hydrogen atom at an alpha-position in a side chain with an olefin in the presence of a solid base which is obtainable by heating an alumina, an alkali metal hydroxide and an alkali metal or an alumina containing at least 1.3% by weight of water and an alkali metal in an inert gas atmosphere at a specific temperature as a catalyst.Type: GrantFiled: January 7, 1992Date of Patent: July 13, 1993Assignee: Sumitomo Chemical Company, Ltd.Inventors: Masami Fukao, Takuo Hibi, Kazuo Kimura, Masahiro Usui, Gohfu Suzukamo
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Patent number: 5196622Abstract: A process is provided comprising contacting a hydrocarbyl alkali metal compound with a nitrogen-containing compound in the presence of an aromatic compound and at least one alpha-olefin. Optionally, a catalytic support is present during this contacting. In another embodiment of this invention a process is provided comprising: (a) contacting a hydrocarbyl alkali metal compound with a nitrogen-containing compound in the presence of an aromatic compound; and thereafter (b) recovering an aromatic/alkali metal/nitrogen complex; and thereafter (c) contacting said aromatic/alkali metal/nitrogen complex with an alpha-olefin. Optionally, a catalytic support is present during steps a, b, and c.Type: GrantFiled: November 22, 1991Date of Patent: March 23, 1993Assignee: Phillips Petroleum CompanyInventors: Ted M. Pettijohn, Mark E. Lashier
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Patent number: 5171915Abstract: It is disclosed that aromatic compounds can be alkylated with mono-olefinic HVI-PAO dimer in contact with an acidic catalyst to produce novel alkylated aromatic compositions. It has been found that the novel HVI-PAO dimer alkylated aromatic compositions exhibit an extraordinary combination of properties relating to low viscosity with high viscosity index and low pour point which renders them very useful as lubricant basestock. Further, it has been found that the novel alkylaromatic compositions of the present invention show improved oxidative stability. Depending upon the substituent groups on the aromatic nucleus, useful lubricant additives can be prepared for improved antiwear, antioxidant and other properties. HVI-PAO dimer is prepared as a product or by-product from 1-alkene oligomerization using reduced chromium oxide on solid support.Type: GrantFiled: February 21, 1989Date of Patent: December 15, 1992Assignee: Mobil Oil CorporationInventors: Thomas R. Forbus, Bruce P. Pelrine
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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: 5019669Abstract: Organic aromatic compounds are alkylated in a Reactive Distillation.TM. reactor, wherein the solid particulate catalyst is slurried in the aromatic feed stream and fed to a reaction zone containing inert distillation packing. Olefin is vaporized and fed to the bottom of the reaction zone and agitates the catalyst while reacting the olefin with the aromatic to form an alkylation product. The alkylation product is removed from the lower end of the reaction zone and recovered. Any unreacted aromatic is distilled overhead and recycled or recovered. Recycling the aromatic controls the molar ratio of aromatic to olefin to the extent that substantially all of the olefin is reacted.Type: GrantFiled: March 10, 1989Date of Patent: May 28, 1991Assignee: Chemical Research & Licensing CompanyInventors: John R. Adams, Lawrence A. Smith
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Patent number: 4962253Abstract: A process for the preparation of vinyl aromatic compounds comprises contacting an aromatic compound and an olefin in the presence of a catalytic amount of a cyclopentadienyl, indenyl, or fluorenyl rhodium complex under reaction conditions sufficient to form the corresponding vinyl aromatic compound. Novel alkyl- or trimethylsilyl-substituted indenyl or fluorenyl compounds are among the compounds suitable for use in the process of the invention.Type: GrantFiled: August 21, 1989Date of Patent: October 9, 1990Assignee: The Dow Chemical CompanyInventor: Robert A. Dubois