Using Organometallic Compound Catalyst Patents (Class 585/457)
  • Patent number: 9079289
    Abstract: 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: Grant
    Filed: August 24, 2012
    Date of Patent: July 14, 2015
    Assignee: TOYO TIRE & RUBBER CO., LTD.
    Inventors: Akinori Sato, Masato Doura
  • Patent number: 8841500
    Abstract: 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: Grant
    Filed: September 12, 2012
    Date of Patent: September 23, 2014
    Assignees: Chevron U.S.A. Inc., Rutgers, The State University of New Jersey
    Inventors: Alan Stuart Goldman, Long Van Dinh, William L. Schinski
  • Publication number: 20140249343
    Abstract: 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: Application
    Filed: June 28, 2012
    Publication date: September 4, 2014
    Applicant: UNIVERSITÄT STUTTGART
    Inventors: Yvonne Traa, Daniel Geiss
  • Publication number: 20140194661
    Abstract: 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: Application
    Filed: December 9, 2013
    Publication date: July 10, 2014
    Applicant: UOP LLC
    Inventors: Christopher P. Nicholas, Mark A. Miller, Antoine Negiz
  • Publication number: 20140004024
    Abstract: 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: Application
    Filed: June 29, 2012
    Publication date: January 2, 2014
    Applicant: UOP LLC
    Inventors: Gregory J. Lewis, Lisa M. Knight, Paulina Jakubczak, Justin E. Stanczyk
  • Patent number: 8536394
    Abstract: 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: Grant
    Filed: March 12, 2010
    Date of Patent: September 17, 2013
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Tsuneyuki Ohkubo, Shinobu Aoki, Masayasu Ishibashi, Masao Imai, Terunori Fujita, Kenji Fujiwara
  • Patent number: 8507396
    Abstract: 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: Grant
    Filed: April 20, 2010
    Date of Patent: August 13, 2013
    Assignee: Chevron U.S.A. Inc.
    Inventors: Saleh Elomari, Thomas V. Harris
  • Publication number: 20130165726
    Abstract: 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: Application
    Filed: December 14, 2012
    Publication date: June 27, 2013
    Applicant: UOP LLC
    Inventor: UOP LLC
  • Publication number: 20130165720
    Abstract: 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: Application
    Filed: December 14, 2012
    Publication date: June 27, 2013
    Applicant: UOP LLC
    Inventor: UOP LLC
  • Patent number: 8288604
    Abstract: 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: Grant
    Filed: August 24, 2007
    Date of Patent: October 16, 2012
    Assignees: Gifu University, Riken, Hamamatsu Photonics K.K.
    Inventors: Masaaki Suzuki, Hisashi Doi, Hideo Tsukada
  • Patent number: 8237002
    Abstract: 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: Grant
    Filed: April 28, 2009
    Date of Patent: August 7, 2012
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Taku Asaumi, Takashi Kamikawa
  • Publication number: 20120004485
    Abstract: 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: Application
    Filed: June 29, 2011
    Publication date: January 5, 2012
    Applicant: UOP LLC
    Inventors: Deng-Yang Jan, Jaime G, Moscoso, Raelynn M. Miller, Susan C. Koster, Julio C. Marte
  • Patent number: 8030508
    Abstract: 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: Grant
    Filed: July 17, 2007
    Date of Patent: October 4, 2011
    Assignees: China Petroleum & Chemical Corporation, Shanghai Research Institute Of Petrochemical Technology Sinopec
    Inventors: Huanxin Gao, Bin Zhou, Yilun Wei, Hua Fang, Ruifang Gu, Shufang Ji
  • Patent number: 7910783
    Abstract: 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: Grant
    Filed: December 14, 2005
    Date of Patent: March 22, 2011
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Alexander Z. Voskoboynikov, Mikhail V. Nikulin, Alexey N. Ryabov, Alexander V. Lygin, Catalina L. Coker, Jo Ann M. Canich
  • Publication number: 20100331594
    Abstract: 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: Application
    Filed: June 29, 2009
    Publication date: December 30, 2010
    Inventors: CHRISTOPHER P. NICHOLAS, Deng-Yang Jan, Jaime G. Moscoso
  • Publication number: 20100184941
    Abstract: 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: Application
    Filed: June 6, 2008
    Publication date: July 22, 2010
    Applicant: ALBEMARLE CORPORATION
    Inventors: William J. Layman, JR., Arthur G. Mack, Charles H. Kolich
  • Publication number: 20100160703
    Abstract: 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: Application
    Filed: February 19, 2010
    Publication date: June 24, 2010
    Applicant: Chevron Oronite Company LLC
    Inventors: Michael Driver, Curt B. Campbell, Thomas V. Harris
  • Patent number: 7605294
    Abstract: 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: Grant
    Filed: November 25, 2008
    Date of Patent: October 20, 2009
    Assignee: Fina Technology, Inc.
    Inventors: Vladimir Marin, Abbas Razavi
  • Publication number: 20090247776
    Abstract: 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: Application
    Filed: July 17, 2007
    Publication date: October 1, 2009
    Applicants: China Petroleum & Chemical Corporation, Shanghai Research Institute Of Petrochemical Technology Sinopec
    Inventors: Huanxin Gao, Bin Zhou, Yilun Wei, Hua Fang, Ruifang Gu, Shufang Ji
  • Patent number: 7473813
    Abstract: 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: Grant
    Filed: June 29, 2006
    Date of Patent: January 6, 2009
    Assignee: Fina Technology, Inc.
    Inventors: Vladimir Marin, Abbas Razavi
  • Patent number: 7282617
    Abstract: 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: Grant
    Filed: March 31, 2006
    Date of Patent: October 16, 2007
    Assignee: Chevron U.S.A. Inc.
    Inventors: William L. Schinski, Curt B. Campbell
  • Patent number: 7141687
    Abstract: 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: Grant
    Filed: November 28, 2003
    Date of Patent: November 28, 2006
    Assignee: BASF Aktiengesellschaft
    Inventors: Jan Kurt Eberhardt, Ernst-Ulrich Würthwein
  • Patent number: 7094941
    Abstract: 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: Grant
    Filed: December 14, 2002
    Date of Patent: August 22, 2006
    Assignee: Indian Petrochemicals Corp., Ltd.
    Inventors: Jagannath Das, Anand Bhimrao Halgeri
  • Patent number: 6723870
    Abstract: 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: Grant
    Filed: September 24, 2002
    Date of Patent: April 20, 2004
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takashi Kamikawa, Junji Morimoto
  • Patent number: 6686495
    Abstract: 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: Grant
    Filed: October 16, 2001
    Date of Patent: February 3, 2004
    Assignee: OMG AG & Co KG
    Inventors: Matthias Beller, Mario Gómez-Andreu, Alexander Zapf, Ralf Karch, Ingo Kleinwächter, Oliver Briel
  • Patent number: 6566571
    Abstract: 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: Grant
    Filed: February 4, 2002
    Date of Patent: May 20, 2003
    Assignee: Degussa AG
    Inventors: Thomas Riermeier, Matthias Beller, Alexander Zapf
  • Patent number: 6504070
    Abstract: 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: Grant
    Filed: February 2, 2001
    Date of Patent: January 7, 2003
    Assignee: Nippon Mitsubishi Oil Corporation
    Inventors: Takaya Matsumoto, Douglas Taube, Roy Anthony Periana
  • Patent number: 6462246
    Abstract: 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: Grant
    Filed: March 29, 2001
    Date of Patent: October 8, 2002
    Assignee: Nippon Mitsubishi Oil Corporation
    Inventors: Takaya Matsumoto, Shinji Nishikawa, Hajime Yoshida
  • Publication number: 20020107426
    Abstract: A process for the preparation of mono-, bi- or poly-functional biaryls in the presence of a metal complex of the general formula IV 1
    Type: Application
    Filed: October 16, 2001
    Publication date: August 8, 2002
    Inventors: Matthias Beller, Mario Gomez-Andreo, Alexander Zapf, Ralf Karch, Ingo Kleinwachter, Oliver Briel
  • Publication number: 20020052535
    Abstract: 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: Application
    Filed: February 2, 2001
    Publication date: May 2, 2002
    Inventors: Takaya Matsumoto, Douglas Taube, Roy Anthony Periana
  • Patent number: 6369265
    Abstract: 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: Grant
    Filed: February 22, 2000
    Date of Patent: April 9, 2002
    Assignee: University of New Orleans Research & Technology Foundation
    Inventors: Steven P. Nolan, Jinkun Huang, Mark L. Trudell, Chunming Zhang
  • Patent number: 6316675
    Abstract: 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: Grant
    Filed: September 23, 1999
    Date of Patent: November 13, 2001
    Assignee: Studiengesellschaft Kohle mbH
    Inventors: Manfred T. Reetz, Gunther Lohmer, Renate Lohmer
  • Patent number: 6281400
    Abstract: 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: Grant
    Filed: January 14, 2000
    Date of Patent: August 28, 2001
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mark Andrew Harmer, Qun Sun
  • Patent number: 6137020
    Abstract: 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: Grant
    Filed: July 31, 1998
    Date of Patent: October 24, 2000
    Assignee: Fina Technology, Inc.
    Inventors: James R. Butler, Mark E. Kuchenmeister
  • Patent number: 6133493
    Abstract: 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: Grant
    Filed: May 6, 1999
    Date of Patent: October 17, 2000
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mark Andrew Harmer, Qun Sun
  • Patent number: 6124462
    Abstract: 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: Grant
    Filed: November 30, 1999
    Date of Patent: September 26, 2000
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: George Y. Li
  • Patent number: 6100437
    Abstract: 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: Grant
    Filed: July 10, 1998
    Date of Patent: August 8, 2000
    Assignee: Albemarle Corporation
    Inventors: David J. Koehl, Edward A. Burt, Patrick T. Ward
  • Patent number: 6040490
    Abstract: 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: Grant
    Filed: August 12, 1998
    Date of Patent: March 21, 2000
    Assignee: Toray Industries, Inc.
    Inventors: Ryoji Ichioka, Shinobu Yamakawa, Hirohito Okino, Hajime Kato, Kazuyoshi Iwayama, Hiroshi Konta, Akira Kitamura
  • Patent number: 6005151
    Abstract: 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: Grant
    Filed: January 30, 1996
    Date of Patent: December 21, 1999
    Assignee: Aventis
    Inventors: Wolfgang Anton Herrmann, Matthias Beller, Ahmed Tafesh
  • Patent number: 5994602
    Abstract: 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: Grant
    Filed: July 29, 1997
    Date of Patent: November 30, 1999
    Assignee: BP Chemicals Limited
    Inventors: Ala'a K Abdul-Sada, Martin Philip Atkins, Brian Ellis, Philip Kenneth Gordon Hodgson, Mark Louis Michael Morgan, Kenneth Richard Seddon
  • Patent number: 5705725
    Abstract: 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: Grant
    Filed: October 2, 1991
    Date of Patent: January 6, 1998
    Assignee: Phillips Petroleum Company
    Inventors: Ted M. Pettijohn, Mark E. Lashier, Henry L. Hsieh
  • Patent number: 5672797
    Abstract: 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: Grant
    Filed: September 25, 1995
    Date of Patent: September 30, 1997
    Assignee: UOP
    Inventor: Joseph A. Kocal
  • Patent number: 5559277
    Abstract: 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: Grant
    Filed: June 29, 1995
    Date of Patent: September 24, 1996
    Assignee: Hoechst AG
    Inventors: Matthias Beller, Wolfgang A. Herrmann, Christoph Brossmer
  • Patent number: 5436361
    Abstract: 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: Grant
    Filed: April 22, 1994
    Date of Patent: July 25, 1995
    Assignee: Clemson University
    Inventors: Graham B. Jones, Robert S. Huber
  • Patent number: 5227559
    Abstract: 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: Grant
    Filed: January 7, 1992
    Date of Patent: July 13, 1993
    Assignee: Sumitomo Chemical Company, Ltd.
    Inventors: Masami Fukao, Takuo Hibi, Kazuo Kimura, Masahiro Usui, Gohfu Suzukamo
  • Patent number: 5196622
    Abstract: 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: Grant
    Filed: November 22, 1991
    Date of Patent: March 23, 1993
    Assignee: Phillips Petroleum Company
    Inventors: Ted M. Pettijohn, Mark E. Lashier
  • Patent number: 5171915
    Abstract: 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: Grant
    Filed: February 21, 1989
    Date of Patent: December 15, 1992
    Assignee: Mobil Oil Corporation
    Inventors: Thomas R. Forbus, Bruce P. Pelrine
  • Patent number: 5043510
    Abstract: 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: Grant
    Filed: March 27, 1989
    Date of Patent: August 27, 1991
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Albert L. Casalnuovo, William A. Nugent, Jr.
  • Patent number: 5019669
    Abstract: 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: Grant
    Filed: March 10, 1989
    Date of Patent: May 28, 1991
    Assignee: Chemical Research & Licensing Company
    Inventors: John R. Adams, Lawrence A. Smith
  • Patent number: 4962253
    Abstract: 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: Grant
    Filed: August 21, 1989
    Date of Patent: October 9, 1990
    Assignee: The Dow Chemical Company
    Inventor: Robert A. Dubois