Rhodium Containing Patents (Class 502/166)
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Patent number: 7144839Abstract: A transition metal complex having the following Formula (A): wherein the monovalent groups R1 and R2 are —Ra, —ORb, —NRcRd, and —NHRe; the monovalent groups Ra, Rb, Rc, Rd and Re, and the divalent group R3 are (i) aliphatic hydrocarbon, (ii) alicyclic hydrocarbon, (iii) aromatic hydrocarbon, (iv) alkyl substituted aromatic hydrocarbon (v) heterocyclic groups and (vi) heterosubstituted derivatives of said groups (i) to (v); M is a Group (3) to (11) or lanthanide metal; E is phosphorus or arsenic; X is an anionic group, L is a neutral donor group; n is (1) or (2), y and z are independently zero or integers, such that the number of X and L groups satisfy the valency and oxidation state of the metal M. n is preferably (2) and the two resulting R1 groups are preferably linked.Type: GrantFiled: March 18, 2004Date of Patent: December 5, 2006Assignee: Innovene Europe LimitedInventors: Vernon Charles Gibson, Grant Berent Jacobsen, David John Jones, Richard James Long
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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: 7109343Abstract: Compounds having the formula: are disclosed. M1 and M2 are the same or different and are transition metal atoms or ions; Z2 and Z3, independently, are the atoms necessary to complete a 3–12 membered heterocyclic ring; Z1 is an alkylene or arylene group; Q1 and Q2 are the same or different and are electron withdrawing groups; L1 and L3, taken together, represent —O—CR13—O—; L2 and L4, taken together, represent —O—CR14—O—; and R13 and R14 are the same or different and are selected from the group consisting of alkyl groups and aryl groups or R13 and R14 represent alkylene or arylene groups that are directly or indirectly bonded to one another. Methods for making such compounds are also disclosed, as are intermediates which can be used in their preparation. Also disclosed are methods for carrying out C—H insertion reactions using bis-transition metal catalysts, such as the above compounds. Procedures for preparing d-threo methylphenidate, tolterodine, CDP-840, nominfensine, and sertraline, are described.Type: GrantFiled: April 5, 2004Date of Patent: September 19, 2006Assignee: The Research Foundation of State University of New YorkInventor: Huw M. L. Davies
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Patent number: 7049473Abstract: The present invention relates to a process for hydroformylating in the presence of a catalyst comprising at least one complex of a metal of transition group VIII with mono-phosphorus compounds which are capable of dimerizing via noncovalent bonds as ligands, to such catalysts and to their use.Type: GrantFiled: March 23, 2004Date of Patent: May 23, 2006Assignee: BASF AktiengesellschaftInventors: Thomas Mackewitz, Martin Volland, Rocco Paciello, Ansgar Schäfer, Bernhard Breit, Wolfgang Seiche
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Patent number: 7030051Abstract: Disclosed is method for increasing the efficiency of a dirhodium catalyst. The method includes providing a dirhodium catalyst, providing an organic ester, and contacting the dirhodium catalyst and the organic ester under conditions effective to increase the efficiency of the dirhodium catalyst. The organic ester is selected such that it is not a substrate for catalysis by the dirhodium catalyst. Dirhodium catalyst compositions which include a dirhodium catalyst and an organic ester are also disclosed. In these compositions, the organic ester is not a substrate for catalysis by the dirhodium catalyst. The method and compositions can be used in a number of reactions, including insertion reactions (e.g., C—H insertions, Si—H insertions, O—H insertions, and N—H insertions) cyclopropanation reactions, annulations (e.g., [3+2] annulations and [3+4] annulations), and ?,?-diarylalkanoate syntheses.Type: GrantFiled: August 27, 2002Date of Patent: April 18, 2006Assignee: The Research Foundation of State University of New YorkInventor: Huw M. L. Davies
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Patent number: 7026266Abstract: A hetergeneous catalyst includes a solid support having deposited thereon a catalyticaly active material, which is substantially insoluble in organic and aqueous liquid media. The insoluble material is constructed from secondary building blocks derived from suitable organometallic active components, and the organometallic active component may be molecularly modified so as to introduce two or more anionic functional groups. These molecularly modified organometallic components, upon interaction with salts of Ca2+, Sr2+ and Ba2+, provde the practically insoluble solid material. Methods of formuatling the organometallic active materials on a solid support as a solid catalyst are also provided. The catalysts are capable of catalyzing diverse reactions in polar and nonpolar reaction media, and the overall integrity of the formulation as a solid material in a liquid phase provides easy catalyst and product separation.Type: GrantFiled: April 30, 2001Date of Patent: April 11, 2006Assignee: Council of Scientific & Industrial ResearchInventors: Raghunath Vitthal Chaudhari, Avinash Narendra Mahajan
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Patent number: 6984604Abstract: Supported bis(phosphorus) ligands are disclosed for use in a variety of catalytic processes, including the isomerization, hydrogenation, hydroformylation, and hydrocyanation of unsaturated organic compounds. Catalysts are formed when the ligands are combined with a catalytically active metal, such as nickel.Type: GrantFiled: November 26, 2002Date of Patent: January 10, 2006Assignee: Invista North America S.A.R.L.Inventors: Michael W. Cobb, Weiming Qiu
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Patent number: 6962891Abstract: Disclosed are dirhodium catalyst compositions. One such dirhodium catalyst composition includes a dirhodium catalyst and a solid support. The dirhodium catalyst includes a Rh—Rh moiety and four bridging ligand moieties. The dirhodium catalyst and the solid support are bound together, but they are not covalently bound together via one or more of the bridging ligand moieties. Another such dirhodium catalyst composition includes a dirhodium tetracarboxylate catalyst and a solid support, and the dirhodium tetracarboxylate catalyst and the solid support are bound together. Yet another such dirhodium catalyst composition includes a dirhodium catalyst and a solid support, where the dirhodium catalyst includes a Rh—Rh moiety and where the dirhodium catalyst and the solid support are bound together via at least one of the rhodiums' axial positions. The compositions can be used in a number of reactions, including insertion reactions (e.g.Type: GrantFiled: August 27, 2002Date of Patent: November 8, 2005Assignee: The Research Foundation of State University of New YorkInventors: Huw M. L. Davies, Tadamichi Nagashima
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Patent number: 6878838Abstract: Chiral porous zirconium phosphonates containing metal complex moieties are provided, synthesized via a molecular building block approach, and characterized by a variety of techniques including TGA, adsorption isotherms, XRD, SEM, IR, and microanalysis. These hybrid solids may be used for enantioselective heterogeneous asymmetric hydrogenation of aromatic ketones with remarkably high e.e. values of up to 99.2%. Similarly prepared chiral porous solids may be used for asymmetric hydrogenation of ?-keto esters with e.e.'s of up to 95%. The solid catalysts can also be easily recycled and reused multiple times without the loss of activity and enantioselectivity. Ready tunability of such a molecular building block approach allows the optimization of these hybrid materials to provide practically useful heterogeneous asymmetric catalysts.Type: GrantFiled: March 24, 2003Date of Patent: April 12, 2005Assignee: The University of North Carolina at Chapel HillInventors: Wenbin Lin, Aiguo Hu, Helen L. Ngo
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Patent number: 6878665Abstract: The invention relates to novel diphosphines, in optically pure or racemic form, of formula (I): in which: R1 and R2 are a (C5-C7)cycloalkyl group, an optionally substituted phenyl group or a 5-membered heteroaryl group; and A is (CH2—CH2) or CF2. The invention further relates to the use of a compound of formula (I) as a ligand for the preparation of a metal complex useful as a chiral catalyst in asymmetric catalysis, and to the chiral metal catalysts comprising at least one ligand of formula (I).Type: GrantFiled: September 16, 2002Date of Patent: April 12, 2005Assignee: SynkemInventors: Sébastien Duprat de Paule, Nicolas Champion, Virginie Vidal, Jean-Pierre Genet, Philippe Dellis
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Ortho substituted chiral phosphines and phosphinites and their use in asymmetric catalytic reactions
Patent number: 6855657Abstract: 3,3?-Substituted chiral biaryl phosphine and phosphinite ligands and metal complexes based on such chiral ligands useful in asymmetric catalysis are disclosed. The metal complexes are useful as catalysts in asymmetric reactions, such as, hydrogenation, hydride transfer, allylic alkylation, hydrosilylation, hydroboration, hydrovinylation, hydroformylation, olefin metathesis, hydrocarboxylation, isomerization, cyclopropanation, Diels-Alder reaction, Heck reaction, isomerization, Aldol reaction, Michael addition, epoxidation, kinetic resolution and [m+n] cycloaddition. The metal complexes are particularly effective in Ru-catalyzed asymmetric hydrogenation of beta-ketoesters to beta-hydroxyesters and Ru-catalyzed asymmetric hydrogenation of enamides to beta amino acids.Type: GrantFiled: September 11, 2003Date of Patent: February 15, 2005Assignee: The Penn State Research FoundationInventor: Xumu Zhang -
Patent number: 6841499Abstract: A supported catalyst comprises a cationic rhodium(I) complex of the formula wherein R1 and R2 are the same or different hydrocarbon groups of up to 30 C atoms, or R1 and R2 are linked to form a ring, and a heterogeneous support medium that provides anionic binding sites. Such a complex is particularly useful as a catalyst in a process of hydrogenating an aldehyde to produce the corresponding primary alcohol.Type: GrantFiled: October 6, 2000Date of Patent: January 11, 2005Assignee: Chirotech Technology LimitedInventors: Mark Joseph Burk, Arne Gerlach
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Patent number: 6831035Abstract: Disclosed are novel catalyst systems comprising (1) a diorgano fluorophosphite ligand; (2) rhodium, wherein the ratio of gram moles fluorophosphite ligand (1) to gram atoms of rhodium is at least 1:1; and (3) a Group VIII metal, other than rhodium, or Group VIII metal-containing compound, in an amount effective to reduce the formation of HF during the use of the catalyst system. The presence of the other Group VIII metal decreases the amount of hydrogen fluoride produced during the use of the catalyst system. The hydrogen fluoride originates from very low level degradation of the ligand. Also disclosed are novel catalyst solutions of the aforesaid catalyst system and the use of the catalyst system in the hydroformylation of olefins to produce aldehydes.Type: GrantFiled: January 22, 2002Date of Patent: December 14, 2004Assignee: Eastman Kodak CompanyInventors: Thomas Allen Puckette, Ginette Struck Tolleson
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Patent number: 6828271Abstract: Chiral ligands and transition metal complexes based on such chiral ligands useful in asymmetric catalysis are disclosed. The chiral ligands include phospholanes, P,N ligands, N,N ligands, biphenols, and chelating phosphines. The ferrocene-based irridium (R,R)-f-binaphane complex reduces imines to the corresponding amines with 95-99.6% enantioselectivity and reduces &bgr;-substituted-&agr;-arylenamides with 95% enantioselectivity. The transition metal complexes of the chiral ligands are useful in asymmetric reactions such as asymmetric hydrogenation of imines, asymmetric hydride transfer reactions, hydrosilylation, hydroboration, hydrovinylation, hydroformylation, allylic alkylation, cyclopropanation, Diels-Alder reaction, Heck reaction, isomerization, Aldol reaction, Michael addition and epoxidation reactions.Type: GrantFiled: December 13, 2002Date of Patent: December 7, 2004Assignee: The Penn State Research FoundationInventors: Xumu Zhang, Dengming Xiao
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Publication number: 20040220049Abstract: A solid catalyst for asymmetric hydrogenation reactions is disclosed comprising a chiral cationic metal-ligand complex immobilised on a mesoporous alumino-silicate support. The catalyst is formed by ion exchange with the acid sites of the support. The catalyst is reusable, and maintains its activity after use.Type: ApplicationFiled: September 22, 2003Publication date: November 4, 2004Inventors: William Patrick Hems, Graham John Hutchings
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Patent number: 6794328Abstract: The present invention provides a novel phosphine compound, specifically to provide a novel phosphine compound useful as a ligand for the above catalysts, in particular, a novel catalyst having an excellent performance (chemical selectivity, enantio-selectivity, catalytic activity) as a catalyst for asymmetric synthetic reactions, particularly asymmetric hydrogenation. A diphosphine compound represented by the general formula (1): wherein R1 and R2 each independently represents a lower alkyl group, a cycloalkyl group, an unsubstituted or substituted phenyl group, or a five-membered heteroaromatic ring residue.Type: GrantFiled: June 3, 2003Date of Patent: September 21, 2004Assignee: Takasago International CorporationInventors: Tohru Yokozawa, Takao Saito
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Publication number: 20040138056Abstract: A series of novel late transition metal catalysts for olefin oligomerization have been invented. The catalysts demonstrate high activity and selectivity for linear &agr;-olefins.Type: ApplicationFiled: October 24, 2003Publication date: July 15, 2004Inventors: Baiyi Zhao, Smita Kacker, Jo Ann Marie Canich
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Patent number: 6730629Abstract: A phosphine compound having excellent properties (chemical selectivity, enantioselectivity, catalytic activity) as a catalyst for asymmetric syntheses, especially asymmetric hydrogenations. A phosphine-phospholane compound represented by the following formula (1): a phosphine-primary phosphine intermediate; a transition metal complex including the phosphine-phospholane compound of formula (1) and a transition metal, and a catalyst including the transition metal complex.Type: GrantFiled: December 10, 2002Date of Patent: May 4, 2004Assignee: Takasago International CorporationInventors: Kazuhiko Matsumura, Takao Saito
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Patent number: 6677268Abstract: An improved catalyst based on cobalt and/or rhodium dissolved in a non-aqueous ionic solvent which is liquid at a temperature of less than 90° C. More particularly, the catalyst comprises at least one complex of cobalt and/or rhodium co-ordinated with at least one nitrogen-containing ligand and the non-aqueous ionic solvent comprises at least one quaternary ammonium and/or phosphonium cation and at least one inorganic anion.Type: GrantFiled: July 12, 2002Date of Patent: January 13, 2004Assignee: Institut Francais du PetroleInventors: Gerhard Hillebrand, Andre Hirschauer, Dominique Commereuc, Helene Olivier-Bourbigou, Lucien Saussine
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Patent number: 6664350Abstract: The invention relates to supported ligands and catalysts for use in the polymerization of olefinically unsaturated monomers such as vinylic monomers, comprising the use of a compound attached to support, the compound being capable of complexing with a transitional metal. Preferably the compound capable of complexing with a transition metal is a diimine such as a 1,4-diaza-1,3-butadiene, a 2-pyridinecarbaldehyde imine, an oxazolidone or a quinoline carbaldeyde. Preferably the catalysts are used in conjunction with an initiator comprising a homolytically cleavable bond with a halogen atom. The application also discloses processes for attaching ligands to supports, and processes for using the catalysts disclosed in the application.Type: GrantFiled: August 14, 2000Date of Patent: December 16, 2003Assignee: University of WarwickInventors: David M. Haddleton, Arnaud Radigue, Dax Kukulj, David Duncalf
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Patent number: 6617279Abstract: Hydroxyaromatic compounds such as phenol are carbonylated with oxygen and carbon monoxide in the presence of a catalyst system comprising a Group VIIIB metal, preferably palladium; an iodide salt, preferably sodium iodide; and at least one organic bisphosphine such as 1,3-bis(diphenylphosphino)propane or 1,4-bis(diphenylphosphino)butane. The catalyst system also preferably contains a compound of cerium or lead.Type: GrantFiled: February 12, 2001Date of Patent: September 9, 2003Assignee: General Electric CompanyInventors: Ben Purushotam Patel, Grigorii Lev Soloveichik, John Yaw Ofori
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Patent number: 6608231Abstract: The invention relates to novel double metal cyanide (DMC) catalysts for the preparation of polyether polyols by polyaddition of alkylene oxides to starter compounds containing active hydrogen atoms, wherein the catalyst contains a) double metal cyanide compounds, b) organic complex ligands other than c), and c) carboxylic acid ester of polyhydric alcohols. The catalysts according to the invention have greatly increased activity in the preparation of polyether polyols.Type: GrantFiled: March 13, 2001Date of Patent: August 19, 2003Assignee: Bayer AktiengesellschaftInventors: Pieter Ooms, Jörg Hofmann, Pramod Gupta
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Publication number: 20030130112Abstract: Disclosed are dirhodium catalyst compositions. One such dirhodium catalyst composition includes a dirhodium catalyst and a solid support. The dirhodium catalyst includes a Rh—Rh moiety and four bridging ligand moieties. The dirhodium catalyst and the solid support are bound together, but they are not covalently bound together via one or more of the bridging ligand moieties. Another such dirhodium catalyst composition includes a dirhodium tetracarboxylate catalyst and a solid support, and the dirhodium tetracarboxylate catalyst and the solid support are bound together. Yet another such dirhodium catalyst composition includes a dirhodium catalyst and a solid support, where the dirhodium catalyst includes a Rh—Rh moiety and where the dirhodium catalyst and the solid support are bound together via at least one of the rhodiums' axial positions. The compositions can be used in a number of reactions, including insertion reactions (e.g.Type: ApplicationFiled: August 27, 2002Publication date: July 10, 2003Inventors: Huw M. L. Davies, Tadamichi Nagashima
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Publication number: 20030130536Abstract: Disclosed is method for increasing the efficiency of a dirhodium catalyst. The method includes providing a dirhodium catalyst, providing an organic ester, and contacting the dirhodium catalyst and the organic ester under conditions effective to increase the efficiency of the dirhodium catalyst. The organic ester is selected such that it is not a substrate for catalysis by the dirhodium catalyst. Dirhodium catalyst compositions which include a dirhodium catalyst and an organic ester are also disclosed. In these compositions, the organic ester is not a substrate for catalysis by the dirhodium catalyst. The method and compositions can be used in a number of reactions, including insertion reactions (e.g., C—H insertions, Si—H insertions, O—H insertions, and N—H insertions) cyclopropanation reactions, annulations (e.g., [3+2] annulations and [3+4] annulations), and &ohgr;,&ohgr;-diarylalkanoate syntheses.Type: ApplicationFiled: August 27, 2002Publication date: July 10, 2003Inventor: Huw M. L. Davies
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Patent number: 6579997Abstract: A metallacrown ether ligand chelates a transition metal atom to form a catalyst well suited to perform hydroformylation in the presence of carbon monoxide, hydrogen and an unsaturated substrate compound.Type: GrantFiled: July 3, 2002Date of Patent: June 17, 2003Assignee: UAB Research FoundationInventors: Gary M. Gray, Maheswaran Harihara Sarma, Dale C. Smith
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Patent number: 6566298Abstract: The invention relates to the preparation and use as catalysts of diphosphines of the formula (I) in which R is C6-C14-aryl or C4-C13-heteroaryl containing 1 to 3 heteroatoms selected from the group consisting of nitrogen, oxygen, and sulfur, wherein the aryl and heteroaryl radicals may optionally be substituted by halogen, C1-C6-alkyl, C1-C6-alkoxy, and/or trimethylsilyl, and R1 to R4, independently of one another, are each hydrogen, C1-C10-alkyl, C1-C10-alkoxy, F, Cl, or Br.Type: GrantFiled: August 15, 2002Date of Patent: May 20, 2003Assignee: Bayer AktiengesellschaftInventors: Birgit Driessen-Hölscher, Joachim Kralik, Inga Ritzkopf, Christian Steffens, Guido Giffels, Claus Dreisbach, Thomas Prinz, Walter Lange
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Patent number: 6566297Abstract: Provided is a selective hydrogenation process for producing aminonitriles by contacting the corresponding dinitriles with a hydrogen-containing fluid in the presence of a hydrogenation catalyst, a solvent and tetraalkylammonium hydroxide and/or tetraalkylphosphonium hydroxide additive.Type: GrantFiled: March 7, 2001Date of Patent: May 20, 2003Assignee: E. I. du Pont de Nemours and CompanyInventor: Alex Sergey Ionkin
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Patent number: 6555715Abstract: A process has been developed for oxygenating linear C2 to C6 alkanes to ketones or aldehydes. The process involves reacting the alkanes with oxygen in the presence of a catalyst comprising an imide promoter and a metal co-catalyst. An example of the imide is N-hydroxyphthalimide and an example of the co-catalyst is Co (acetylacetonate). The process is preferably carried out using an inert solvent, an example of which is acetic acid. Optionally, the oxygenated product can be hydrogenated to give the corresponding alcohol which can optionally in turn be dehydrated to provide the corresponding olefin.Type: GrantFiled: October 11, 2001Date of Patent: April 29, 2003Assignee: UOP LLCInventors: Joseph A. Kocal, Robert R. Frame, Jeffery C. Bricker
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Patent number: 6534657Abstract: Ferrocene anchored chiral ligands and metal complexes based on such chiral ligands useful in asymmetric catalysis are disclosed. The metal complexes according to the present invention are useful as catalysts in asymmetric reactions, such as, hydrogenation, hydride transfer, allylic alkylation, hydrosilylation, hydroboration, hydrovinylation, hydroformylation, olefin metathesis, hydrocarboxylation, isomerization, cyclopropanation, Diels-Alder reaction, Heck reaction, isomerization, Aldol reaction, Michael addition; epoxidation, kinetic resolution and [m+n] cycloaddition. The new ligands are effective for asymmetric Pd-catalyzed allylic alkylation reactions and Ag-catalyzed [3+2] cyclization of azomethine ylides.Type: GrantFiled: February 9, 2001Date of Patent: March 18, 2003Assignee: The Penn State Research FoundationInventor: Xumu Zhang
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Patent number: 6500909Abstract: A transition metal compound represented by the general formula (2) or (3) described below, a catalyst component for olefin polymerization comprising said transition metal compound, a catalyst component for olefin polymerization using said transition metal compound and (C) and/or (D) described below, and a process for producing an olefinic polymer wherein olefins are homopolymerized or olefins are copolymerized with other olefins and/or other polymerizable unsaturated compound using said catalyst for olefin polymerization. (C); A specific aluminum compound (D); A specific boron compound.Type: GrantFiled: May 18, 2001Date of Patent: December 31, 2002Assignee: Sumitomo Chemical Company, LimitedInventors: Wataru Hirahata, Makoto Itagaki, Kotohiro Nomura
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Patent number: 6455740Abstract: Process to separate a group 8-10 metal/phosphite ligand complex from an organic liquid mixture, wherein the following steps are performed (1) contacting the organic liquid with a support having bonded thereto an organophosphine ligand and separating the organic mixture which is poor in group 8-10 metal/phosphite ligand complex, (2) contacting the thus obtained loaded support with an organic solvent and carbon monoxide and separating the thus obtained organic solvent rich in group 8-10 metal/phosphite ligand complex, and (3) reusing the support obtained in step (2) in step (1).Type: GrantFiled: February 8, 2000Date of Patent: September 24, 2002Assignee: DSM N.V.Inventors: Nicolaas L. H. L. Broeders, Onko J. Gelling, Hendrik F. Martens, Klaas Timmer, Harmen A. Meinema
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Patent number: 6414099Abstract: Single-site catalysts useful for polymerizing olefins are disclosed. The organometallic catalysts incorporate a Group 3 to 10 transition, lanthanide or actinide metal and a caged diimide ligand. The diimide ligands are made by a tandem Diels-Alder and photochemical [2+2] cycloaddition sequence to give a multicyclic dione, followed by condensation with a primary amine. Because a wide variety of caged diimide ligands are easy to prepare from commercially available dienes and dienophiles, the invention enables the preparation of a new family of single-site catalysts. Based on their unique structure and geometry, the catalysts offer polyolefin producers new ways to improve activity, control comonomer incorporation, or regulate polyolefin tacticity.Type: GrantFiled: October 18, 2000Date of Patent: July 2, 2002Assignee: Equistar Chemicals, LPInventors: Gregory G. Hlatky, Jonathan L. Schuchardt
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Patent number: 6410746Abstract: Compounds having the formula: are disclosed. M1 and M2 are the same or different and are transition metal atoms or ions; Z2 and Z3, independently, are the atoms necessary to complete a 3-12 membered heterocyclic ring; Z1 is an alkylene or arylene group; Q1 and Q2 are the same or different and are electron withdrawing groups; L1 and L3, taken together, represent —O—CR13—O—; L2 and L4, taken together, represent —O—CR14—O—; and R13 and R14 are the same or different and are selected from the group consisting of alkyl groups and aryl groups or R13 and R14 represent alkylene or arylene groups that are directly or indirectly bonded to one another. Methods for making such compounds are also disclosed, as are intermediates which can be used in their preparation. Also disclosed are methods for carrying out C—H insertion reactions using bis-transition metal catalysts, such as the above compounds.Type: GrantFiled: March 8, 2000Date of Patent: June 25, 2002Assignee: Research Foundation of State University of New York, TheInventor: Huw M. L. Davies
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Patent number: 6372931Abstract: A catalytic transfer hydrogenation process is provided. The catalyst employed in the process is a metal cyclopentadienyl complex which is coordinated to defined bidentate ligands. Preferred metals include rhodium, ruthenium and iridium. Preferred bidentate ligands are diamines and aminoalcohols, particularly those comprising chiral centers. The hydrogen donor is advantageously a secondary alcohol or a mixture of triethylamine and formic acid. The process can be employed to transfer hydrogenate ketones and imines, which are preferably prochiral. Catalysts for use in such a process are also provided.Type: GrantFiled: November 9, 1999Date of Patent: April 16, 2002Assignee: Avecia LimitedInventors: Andrew John Blacker, Ben James Mellor
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Patent number: 6372682Abstract: The present invention provides catalyst systems useful in the polymerization of olefins comprising a transition metal component and a ligand component comprising a Nitrogen atom and/or functional groups comprising a Nitrogen atom, generally in the form of an imine functional group. In certain embodiments, the ligand component may further comprise a phosphorous atom. Preferred ligand components are bidentate (bind to the transition metal at two or more sites) and include a nitrogen-transition metal bond from two imine groups. The transition metal-ligand complex is generally cationic and associated with a weakly coordinating anion. In a preferred embodiment, the catalyst system of the present invention further comprises a Lewis or Bronsted acid complexed with the ligand component of the transition metal-ligand complex.Type: GrantFiled: February 9, 2001Date of Patent: April 16, 2002Assignee: Eastman Chemical CompanyInventors: James Allen Ponasik, Jr., Jason Patrick McDevitt, Christopher Moore Killian, Peter Borden Mackenzie, Leslie Shane Moody
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Patent number: 6348611Abstract: The present invention relates to a process for carbonylation of epoxide derivatives, in which the reactivity, selectivity and the yield are superior. More specifically, the present invention relates to a process for hydroformylation of an epoxide derivative in which there is utilized a transition metal catalyst having a cyclopentadienyl radical, thereby improving the reactivity and selectivity. Further, the present invention relates to a process for hydroesterification of an epoxide derivative, in which a proper catalyst is selected, and the reaction temperature and pressure are adjusted within proper ranges under the presence of a cobalt catalyst, thereby improving the product selectivity and the yield.Type: GrantFiled: August 25, 1999Date of Patent: February 19, 2002Assignee: Samsung Electronic Co., Ktd.Inventors: Byeong-No Lee, Duck-Joo Yang, Young-Hun Byun
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Publication number: 20010034417Abstract: Molecular weight-enlarged, homogeneously soluble ligands are provided that are especially useful for hydrogenation catalysts, wherein the ligands contain homochiral active centers of bis(3,4-diarylphosphinyl)pyrrolidines, and their use in producing cataylsts for enantioselective reactions, as well as the catalysts thus produced.Type: ApplicationFiled: January 24, 2001Publication date: October 25, 2001Applicant: Degussa-Huels AktiengesellschaftInventors: Olaf Burkhardt, Jens Woeltinger, Andreas Bommarius, Juan Jose Almena Perea, Hans Henniges, Karlheinz Drauz, Andreas Karau, Jean-Louis Philippe, Hans-Peter Krimmer, Gunther Oehme
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Patent number: 6294495Abstract: An activated tridentate-, monoanionic-ligand-based transition metal catalyst in a reduced oxidation state for olefin polymerization is disclosed. Transition metal catalyst precursors for these catalysts have the formulae: in which M is a transition metal from Groups 4-9 in a reduced oxidation state, X is a mono anionic ligand, L is a neutral donor group, E is a neutral donor group from Groups 15 and 16, E′ is a monoanionic donor group from Group 15, T is a bridging group, n is 1-3 as needed to balance the charge on M, p is 0-3 and q is 1-2. Olefin polymerization is exemplified.Type: GrantFiled: April 29, 1999Date of Patent: September 25, 2001Assignee: ExxonMobil Chemicals Patent Inc.Inventor: Phillip T. Matsunaga
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Patent number: 6242377Abstract: A transition metal compound represented by the general formula (2) or (3) described below, a catalyst component for olefin polymerization comprising said transition metal compound, a catalyst component for olefin polymerization using said transition metal compound and (C) and/or (D) described below, and a process for producing an olefinic polymer wherein olefins are homopolymerized or olefins are copolymerized with other olefins and/or other polymerizable unsaturated compound using said catalyst for olefin polymerization. (C); A specific aluminum compound. (D); A specific boron compound.Type: GrantFiled: March 11, 1999Date of Patent: June 5, 2001Assignee: Sumitomo Chemical Company, LimitedInventors: Wataru Hirahata, Makoto Itagaki, Kotohiro Nomura
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Patent number: 6197716Abstract: The present invention relates to a hydrogenation process for the production of aromatic halogen-amino compounds by means of catalytic hydrogenation on noble metal catalysts of corresponding aromatic halonitro compounds, characterised in that a rhodium, ruthenium, iridium, platinum or palladium catalyst which is modified with an inorganic or organic phosphorus compound with a degree of oxidation of less than V, is used, in the presence of a vanadium compound.Type: GrantFiled: November 4, 1998Date of Patent: March 6, 2001Assignee: Novartis AGInventors: Peter Baumeister, Urs Siegrist, Martin Studer
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Patent number: 6194593Abstract: An optically active 1,2-bis(dialkylphosphino) benzene derivative represented by the general formula (1) which is suitable as a ligand for a transition metal catalyst in asymmetrical hydrogenation is provided. Also provided is a process for producing such a benzene derivative, and a rhodium metal complex having such a benzene derivative as a ligand which is useful as an asymmetric catalyst for use in asymmetrical hydrogenation. (where R1 denotes a straight or branched alkyl group having 2-6 carbon atoms, and each of the asterisks denotes an asymmetric phosphorus atom).Type: GrantFiled: January 28, 2000Date of Patent: February 27, 2001Assignee: Nippon Chemical Industrial Co., Ltd.Inventors: Tsuneo Imamoto, Tomoya Miura, Hironari Yamada
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Patent number: 6191063Abstract: A catalyst comprising rhodium and a compound of the formula (I) in which m is a number from 1 to 1000; x is a number from 0 to 4; W is a group of the formulae —CH2—CH2—, —CH(CH3)CH2—or —CH2CH(CH3)—; R is hydrogen, a straight-chain or branched C1-C5— alkyl radical; or a group of the formulae where a, b, c, d and e independently of one another are a number from 0 to 1000, at least one of the numbers a, b, c, d and e being greater than 0; R5, R6, R7, R8 and R9 are identical or different and are hydrogen, C1-C5-alkyl or a group of the formula R1 and R2 are identical or different and are a straight-chain, branched or cyclic C1-C30-alkyl radical or C6-10-aryl radical, which is unsubstituted or substituted by from one to five C1-C3-alkyl radicals, and L is C1-C5-alkyl, C1-C5-alkoxy, NO2, NR3R4, where R3 and R4 independently of one another are hydrogen or C1-C4-alkyl, or L is Cl or OH, for hydroformylation reType: GrantFiled: July 1, 1999Date of Patent: February 20, 2001Assignee: Celanese GmbHInventors: Sandra Bogdanovic, Carl-Dieter Frohning, Helmut Bahrmann, Matthias Beller, Steffen Haber, Hans-Jerg Kleiner
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Patent number: 6184171Abstract: A heterogeneous catalyst composition suitable for olefinic polymerization and to methods of forming polyolefinic products using said composition. The catalyst composition comprises an anionic metalloid silane modified inorganic oxide and the cationic remnant of a transition metal bidentate or tridentate compound represented by the formula: T—[—SiR′R″ODM(Q)3]a−n[Cat]b+m wherein each of the symbols above is defined within the subject application.Type: GrantFiled: October 5, 1998Date of Patent: February 6, 2001Assignee: W.R. Grace & Co. -ConnInventor: Keng-Yu Shih
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Patent number: 6150298Abstract: Process for the telomerization of dienesThe present invention relates to a process for the telomerization of dienes, according to which the diene is reacted with a compound containing an active hydrogen atom in the presence of a palladium compound, a water-soluble phosphine ligand and a base, the water-soluble ligand being a bidentate ligand having the following formula I ##STR1## in which R is identical or different and is phenyl, C.sub.1 -C.sub.12 -alkyl or C.sub.3 -C.sub.10 -cycloalkyl, which may be unsubstituted or substituted by one or more radicals R',R' is identical or different and is SO.sub.3.sup.- M.sup.+, --NMe.sub.3.sup.+ or --COO.sup.- M.sup.+,n is an integer from 1 to 6, in each case based on a naphthyl backbone, andM is H, Na, K, Cs or R".sub.4 N.sup.+ where R" is identical or different and is H, C.sub.1 -C.sub.12 -alkyl or C.sub.1 -C.sub.10 -cycloalkyl.Type: GrantFiled: June 25, 1999Date of Patent: November 21, 2000Assignee: Celanese GmbHInventors: Ahmed Tafesh, Matthias Beller, Jochen Krause
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Patent number: 6121184Abstract: Supported bis(phosphorus) ligands are disclosed for use in a variety of catalytic processes, including the hydrocyanation of unsaturated organic compounds. Catalysts are formed when the ligands are combined with a catalytically active metal (e.g., nickel).Type: GrantFiled: July 8, 1998Date of Patent: September 19, 2000Assignee: E. I. du Pont de Nemours and CompanyInventors: Joe Douglas Druliner, Kenneth Gene Moloy, Manxue Wang
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Patent number: 6114272Abstract: A catalyst for preparing aldehydes by hydroformylation of olefins or olefinically unsaturated compounds comprising at least one rhodium compound and a non-aqueous ionic ligand liquid of the formula (Q.sup.+).sub.a A.sup.a-, where Q.sup.+ is a singly charged quaternary ammonium and/or phosphonium cation or the equivalent of a multiply charged ammonium and/or phosphonium cation and A.sup.a- is a sulfonated triarylphosphine.Type: GrantFiled: July 26, 1999Date of Patent: September 5, 2000Assignee: Celanese GmbHInventor: Helmut Bahrmann
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Patent number: 6077958Abstract: Chiral diphosphines are constituted by an aromatic pentatomic biheterocyclic system, suitable to act as chiral ligands and complexes between the diphosphines and transition metals. They may be utilized as chiral catalysts in stereocontrolled reactions, such as diastereo- and enantioselective reduction reactions. Process is for the preparation of these chiral diphosphines; and process is for the preparation of these complexes and for their utilization as chiral catalysts in stereocontrolled reactions.Type: GrantFiled: April 27, 1999Date of Patent: June 20, 2000Assignee: Italfarmaco Sud S.p.A.Inventors: Patrizia Antognazza, Tiziana Benincori, Elisabetta Brenna, Edoardo Cesarotti, Francesco Sannicolo', Licia Trimarco
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Patent number: 6040263Abstract: A novel non-aqueous catalytic composition comprises at least one quaternary ammonium and/or phosphonium salt in which the anion is selected from the group consisting of tetrafluoroborate, tetrachloroborate, hexafluorophosphate, hexafluoroantimonate, hexafluoroarsenate, trifluorosulphonate, fluorosulphonate, trifluoromethylsulphonate, trifluoroarsenate, dichlorocuprate, trichlorocuprate, tetrachlorocuprate, and trichlorozincate, and at least one complex of a transition metal from groups 8, 9 or 10, i.e., iron, ruthenium, colbalt, rhodium iridium, nickel, palladium and platinum. The catalyst can be used in a process of total or selective hydrogenation of unsaturated compounds such as monoolefins, diolefins, acetylene compounds, aromatic compounds, or polynuclear aromatic compounds. Hydrogenation may be accompanied by isomerisation.Type: GrantFiled: September 15, 1998Date of Patent: March 21, 2000Assignee: Institut Francais du PetroleInventors: Lothar Mussmann, Yves Chauvin, Helene Olivier
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Patent number: 6020532Abstract: A process for preparing aldehydes by hydroformylating olefinically unsaturated compounds in the presence of a water-insoluble catalyst composition comprising rhodium complexes containing diphosphine ligands, wherein the diphosphine ligands present are compounds of the formula (I) ##STR1## wherein R.sup.1 is selected from the group consisting of carboxylate (COO.sup.-), sulfonate (SO.sub.3.sup.-), phosphonate (PO.sub.3.sup.2-) and 2-anmino ethtanebisphosphonate, R.sup.Type: GrantFiled: July 9, 1998Date of Patent: February 1, 2000Assignee: Hoechst AktiengesellschaftInventors: Helmut Bahrmann, Peter Lappe, Thomas Muller
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Patent number: RE38947Abstract: A chiral catalyst is disclosed together with methods of using it for enantioselective syntheses. The chiral catalyst includes a nucleus with two metal atoms that has four bridging ligands oriented radially to the axis of the nucleus. Each of these ligands includes a two complexing atoms each complexed to one of the metal atoms. At least one of the bridging ligands includes a chiral center which is bonded to one of the complexing atoms. Preferably, all four of the bridging ligands include a chiral center bonded to one of the complexing atoms. The catalyst of the invention has been found to be useful in catalyzing carbenoid transformation reactions such as cyclopropanation.Type: GrantFiled: February 14, 1996Date of Patent: January 24, 2006Assignee: Research Corporation Technologies, Inc.Inventor: Michael P. Doyle