Copper Containing Patents (Class 502/165)
  • Patent number: 6664350
    Abstract: 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: Grant
    Filed: August 14, 2000
    Date of Patent: December 16, 2003
    Assignee: University of Warwick
    Inventors: David M. Haddleton, Arnaud Radigue, Dax Kukulj, David Duncalf
  • Patent number: 6642327
    Abstract: The invention provides a novel metal complex which, when used with an activating cocatalyst, provides a novel catalyst composition. The invention also provides a polymerization method which utilizes the catalyst composition to produce polymers and copolymers containing polar monomer groups. More specifically, the invention comprises a composition comprising the formula LMXZn wherein X is selected from the group consisting of halides, hydride, triflate, acetates, borates, C1 through C12 alkyl, C1 through C12 alkoxy, C3 through C12 cycloalkyl, C3 through C12 cycloalkoxy, aryl, thiolates, carbon monoxide, cyanate, olefins, and any other moiety into which a monomer can insert. M is selected from the group consisting of Cu, Ag, and Au. L is a nitrogen-containing bidentate ligand having more than two nitrogen atoms. Z is a neutral coordinating ligand and n equals 0, 1, or 2.
    Type: Grant
    Filed: September 17, 2002
    Date of Patent: November 4, 2003
    Assignee: ExxonMobil Research and Engineering Company
    Inventors: Robert T. Stibrany, Smita Kacker
  • Patent number: 6608231
    Abstract: 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: Grant
    Filed: March 13, 2001
    Date of Patent: August 19, 2003
    Assignee: Bayer Aktiengesellschaft
    Inventors: Pieter Ooms, Jörg Hofmann, Pramod Gupta
  • Patent number: 6569354
    Abstract: The invention relates to catalytically bleaching substrates, especially laundry fabrics, with atmospheric oxygen or air. A method of bleaching a substrate is provided that comprises applying to the substrate, in an aqueous medium, a specified organic substance which forms a complex with a transition metal, the complex catalysing bleaching of the substrate by atmospheric oxygen. Also provided is a bleaching composition comprising, in an aqueous medium, atmospheric oxygen and an organic substance which forms a complex with a transition metal, the complex catalysing bleaching of the substrate by the atmospheric oxygen, wherein the aqueous medium is substantially devoid of peroxygen bleach or a peroxy-based or -generating bleach system.
    Type: Grant
    Filed: December 19, 2000
    Date of Patent: May 27, 2003
    Assignee: Unilever Home & Personal Care USA, division of Conopco, Inc.
    Inventor: Ronald Hage
  • Patent number: 6566295
    Abstract: A method and catalyst system for economically producing aromatic carbonates from aromatic hydroxy compounds is disclosed. In one embodiment, the present invention provides a method of carbonylating aromatic hydroxy compounds by contacting at least one aromatic hydroxy compound with oxygen and carbon monoxide in the presence of a carbonylation catalyst system that includes an effective amount of at least one Group 8, 9, or 10 metal source; an effective amount of at least one bromide composition; an effective amount of at least one activating organic solvent; an effective amount of a combination of inorganic co-catalysts comprising at least one titanium source and at least one copper source; and an effective amount of at least one base.
    Type: Grant
    Filed: November 30, 2000
    Date of Patent: May 20, 2003
    Assignee: General Electric Company
    Inventors: Kirill Vladimirovich Shalyaev, Grigorii Lev Soloveichik, Bruce Fletcher Johnson
  • Patent number: 6534657
    Abstract: 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: Grant
    Filed: February 9, 2001
    Date of Patent: March 18, 2003
    Assignee: The Penn State Research Foundation
    Inventor: Xumu Zhang
  • Publication number: 20030050515
    Abstract: A method for producing biphenols by oxidative coupling of dialkylphenols which proceeds in two stages using a copper amine complex which is catalytically effective in each stage is disclosed. A novel copper amine complex is also disclosed wherein the complex exhibits high catalytic activity for the oxidative coupling of substituted phenols under mild conditions, has dual (two stage) activity and can be readily recycled and reused.
    Type: Application
    Filed: August 26, 2002
    Publication date: March 13, 2003
    Inventor: Gregory Kaplan
  • Patent number: 6521735
    Abstract: A process for producing a polyphenylene ether by oxidative polymerization of a phenol compound using a catalyst and an oxygen-containing gas, wherein said catalyst comprises a copper compound, a bromine compound, a diamine compound of formula (1) as recited in the specification, a tertiary monoamine compound and a secondary monoamine compound, and wherein said process comprises the steps of: preparing a catalyst component (P1) in a container which is under a substantially oxygen-free inert atmosphere by mixing the copper compound and the bromine compound to obtain a mixture and then mixing the mixture with the secondary monoamine compound in an amount of at least 2 times the molar amount of the copper atom; separately preparing a catalyst component (P2) by mixing the diamine compound of formula (1) and the tertiary monoamine compound together with a solvent in an oxidative polymerization vessel; adding a predetermined amount of the catalyst component (P1) to the polymerization vessel containing the catalyst c
    Type: Grant
    Filed: June 19, 2001
    Date of Patent: February 18, 2003
    Assignees: Asahi Kasei Kabushiki Kaisha, Mitsubishi Gas Chemical Company, Inc.
    Inventors: Akira Mitsui, Yuji Takeda
  • Publication number: 20030027714
    Abstract: The invention provides a novel metal complex which, when used with an activating cocatalyst, provides a novel catalyst composition. The invention also provides a polymerization method which utilizes the catalyst composition to produce polymers and copolymers containing polar monomer groups. More specifically, the invention comprises a composition comprising the formula LMXZn wherein X is selected from the group consisting of halides, hydride, triflate, acetates, borates, C1 through C12 alkyl, C1 through C12 alkoxy, C3 through C12 cycloalkyl, C3 through C12 cycloalkoxy, aryl, thiolates, carbon monoxide, cyanate, olefins, and any other moiety into which a monomer can insert. M is selected from the group consisting of Cu, Ag, and Au. L is a nitrogen-containing bidentate ligand having more than two nitrogen atoms. Z is a neutral coordinating ligand and n equals 0, 1, or 2.
    Type: Application
    Filed: September 17, 2002
    Publication date: February 6, 2003
    Inventors: Robert T. Stibrany, Smita Kacker
  • Publication number: 20030017941
    Abstract: Catalytic systems and methods for oxidizing materials in the presence of metal catalysts (preferably manganese-containing catalysts) complexed with selected macropolycyclic rigid ligands, preferably cross-bridged macropolycyclic ligands. Included are using these metal catalysts in such processes as: synthetic organic -oxidation reactions such as oxidation of organic functional groups, hydrocarbons, and heteroatoms, including enantiomeric epoxidation of alkenes, enynes, sulfides to sulfones and the like; oxidation of oxidizable compounds (e.g., stains) on surfaces such as fabrics, dishes, countertops, dentures and the like; oxidation of oxidizable compounds in solution, dye transfer inhibition in the laundering of fabrics; and further in the bleaching of pulp and paper products.
    Type: Application
    Filed: May 24, 2002
    Publication date: January 23, 2003
    Applicant: The Procter & Gamble Company
    Inventors: Daryle Hadley Busch, Simon Robert Collinson, Timothy Jay Hubin
  • Patent number: 6506859
    Abstract: The invention is directed towards the formation of polymers and copolymers using late transition metal polymerization catalyst complexes which are formed in situ. In the first process step of the instant invention, a composition having the formula MXZn is simultaneously contacted with a ligand and an activating cocatalyst.
    Type: Grant
    Filed: August 18, 2000
    Date of Patent: January 14, 2003
    Assignee: ExxonMobil Research and Engineering Company
    Inventors: Abhimanyu O. Patil, Robert T. Stibrany, Stephen Zushma, Enock Berluche, Donald N. Schulz
  • Patent number: 6489439
    Abstract: A process for producing a polyphenylene ether by oxidative polymerization of a phenol compound using a catalyst and an oxygen-containing gas, wherein the catalyst comprises a copper compound, a bromine compound, a diamine compound represented by the following formula (1): (wherein, R1, R2, R3 and R4 each independently represents hydrogen or a C1-6 linear or branched alkyl group with the proviso that all of them do not represent hydrogen simultaneously, and R5 represents a linear or methyl-branched C2-5 alkylene group), a tertiary monoamine compound and a secondary monoamine compound, wherein the process comprises the steps of: controlling an absolute pressure at a gaseous phase of a reaction vessel to a range of from 0.098 MPa to less than 0.392 MPa; and feeding the oxygen-containing gas to the reaction vessel, the oxygen-containing gas having an oxygen partial pressure, in terms of an absolute pressure, of from 0.0147 MPa to 0.0883 MPa.
    Type: Grant
    Filed: June 19, 2001
    Date of Patent: December 3, 2002
    Assignees: Asahi Kasei Kabushiki Kaisha, Mitsubishi Gas Chemical Company, Inc.
    Inventors: Akira Mitsui, Yuji Takeda
  • Patent number: 6479425
    Abstract: The invention provides a novel metal complex which, when used with an activating cocatalyst, provides a novel catalyst composition. The invention also provides a polymerization method which utilizes the catalyst composition to produce polymers and copolymers containing polar monomer groups. More specifically, the invention comprises a composition comprising the formula LMXZn wherein X is selected from the group consisting of halides, hydride, triflate, acetates, borates, C1 through C12 alkyl, C1 through C12 alkoxy, C3 through C12 cycloalkyl, C3 through C12 cycloalkoxy, aryl, thiolates, carbon monoxide, cyanate, olefins, and any other moiety into which a monomer can insert. M is selected from the group consisting of Cu, Ag, and Au. L is a nitrogen-containing bidentate ligand having more than two nitrogen atoms. Z is a neutral coordinating ligand and n equals 0, 1, or 2.
    Type: Grant
    Filed: August 18, 2000
    Date of Patent: November 12, 2002
    Assignee: ExxonMobile Research and Engineering Company
    Inventors: Robert T. Stibrany, Smita Kacker
  • Patent number: 6433130
    Abstract: The present inventors has its objects to provide a polymerization catalyst component, a copper compound which can easily be synthesized and is stable. The present invention is related to a method of producing a polymer which comprises using a copper compound represented by the general formula CuXn, LCuXn or L(L′)CnXn (wherein L and L′ each represents a ligand, X represents a halogen atom or an alkoxy, thioxy, allyloxy, amino, secondary amino, tertiary amino, cyano, nitro, alkyl or allyl group, and n represents an integer of 0 to 2) as a catalyst and/or polymerization initiator in polymerizing a vinyl monomer whose polarity value e, when expressed in terms of absolute value, is not more than 1.5.
    Type: Grant
    Filed: February 12, 2001
    Date of Patent: August 13, 2002
    Assignee: Sekisui Chemical Co., Ltd.
    Inventors: Koichi Shibayama, Masao Ogasa
  • Patent number: 6414099
    Abstract: 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: Grant
    Filed: October 18, 2000
    Date of Patent: July 2, 2002
    Assignee: Equistar Chemicals, LP
    Inventors: Gregory G. Hlatky, Jonathan L. Schuchardt
  • Publication number: 20020013446
    Abstract: A process for producing a polyphenylene ether by oxidative polymerization of a phenol compound using a catalyst and an oxygen-containing gas, wherein said catalyst comprises a copper compound, a bromine compound, a diamine compound of formula (1) as recited in the specification, a tertiary monoamine compound and a secondary monoamine compound, and wherein said process comprises the steps of: preparing a catalyst component (P1) in a container which is under a substantially oxygen-free inert atmosphere by mixing the copper compound and the bromine compound to obtain a mixture and then mixing the mixture with the secondary monoamine compound in an amount of at least 2 times the molar amount of the copper atom; separately preparing a catalyst component (P2) by mixing the diamine compound of formula (1) and the tertiary monoamine compound together with a solvent in an oxidative polymerization vessel; adding a predetermined amount of the catalyst component (P1) to the polymerization vessel containing the catalyst c
    Type: Application
    Filed: June 19, 2001
    Publication date: January 31, 2002
    Inventors: Akira Mitsui, Yuji Takeda
  • Publication number: 20020010314
    Abstract: A process for producing a polyphenylene ether by oxidative polymerization of a phenol compound using a catalyst and an oxygen-containing gas, wherein the catalyst comprises a copper compound, a bromine compound, a diamine compound represented by the following formula (1): 1
    Type: Application
    Filed: June 19, 2001
    Publication date: January 24, 2002
    Inventors: Akira Mitsui, Yuji Takeda
  • Patent number: 6294495
    Abstract: 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: Grant
    Filed: April 29, 1999
    Date of Patent: September 25, 2001
    Assignee: ExxonMobil Chemicals Patent Inc.
    Inventor: Phillip T. Matsunaga
  • Patent number: 6245707
    Abstract: Methanol tolerant catalyst materials and a method of making the same are provided. These novel catalyst materials are obtained by mixing together and heat-treating at least two different transition-metal-containing nitrogen chelates. In preferred embodiments, the nitrogen chelates comprise metalloporphyrins such as transition-metal-containing tetraphenylporphins. Preferred transition metals are iron, cobalt, nickel, copper, manganese, ruthenium, vanadium, and zinc, but could be any transition metal other than platinum or palladium. These materials offer improved catalytic oxygen reduction in the presence of methanol, as may occur at a fuel cell cathode after methanol crossover.
    Type: Grant
    Filed: October 28, 1999
    Date of Patent: June 12, 2001
    Assignee: The United States of America as represented by the Secretary of the Army
    Inventors: Dervn Chu, Rongzbong Jiang
  • Patent number: 6184171
    Abstract: 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: Grant
    Filed: October 5, 1998
    Date of Patent: February 6, 2001
    Assignee: W.R. Grace & Co. -Conn
    Inventor: Keng-Yu Shih
  • Patent number: 6160155
    Abstract: A method and catalyst system for economically producing aromatic carbonates from aromatic hydroxy compounds. In one embodiment, the present invention provides a method of carbonylating aromatic hydroxy compounds by contacting at least one aromatic hydroxy compound with oxygen and carbon monoxide in the presence of a carbonylation catalyst system that includes a catalytic amount of an inorganic co-catalyst containing ytterbium. In various alternative embodiments, the carbonylation catalyst system can include an effective amount of a palladium source and an effective amount of a halide composition. Further alternative embodiments can include catalytic amounts of various inorganic co-catalyst combinations.
    Type: Grant
    Filed: April 29, 1999
    Date of Patent: December 12, 2000
    Assignee: General Electric Company
    Inventors: James Lawrence Spivack, Donald Wayne Whisenhunt, Jr., James Norman Cawse, Grigorii Lev Soloveichik
  • Patent number: 6159891
    Abstract: A catalyst for the bisalkoxycarbonylation of olefins comprising a noble metal compound and a phosphine chalcogenide of the following formula (1): ##STR1## wherein each of R.sup.1, R.sup.2 and R.sup.3 is, independently, an alkyl group or an aryl group each of which may have a substituent, and A is a Group 16 element of the Periodic Table; and R.sup.1, R.sup.2 or R.sup.3 may be combined, directly or through a bridging group, with one another where the groups to be combined may be attached either to an identical phosphorus atom or to different phosphorus atoms. Element A includes oxygen, sulfur and selenium atoms. The noble metal compound includes palladium(II) halides and other palladium compounds. The catalyst may further include a copper (I) halide or other copper compound as a co-catalyst. The use of this catalyst can provide the bisalkoxycarbonylation of olefins with efficiency.
    Type: Grant
    Filed: June 14, 1999
    Date of Patent: December 12, 2000
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Kazuhiko Saigo, Yukihiko Hashimoto, Minoru Hayashi
  • Patent number: 6160154
    Abstract: A method and catalyst system for economically producing aromatic carbonates from aromatic hydroxy compounds. In one embodiment, the present invention provides a method of carbonylating aromatic hydroxy compounds by contacting at least one aromatic hydroxy compound with oxygen and carbon monoxide in the presence of a carbonylation catalyst system that includes a catalytic amount of an inorganic co-catalyst containing copper. In various alternative embodiments, the carbonylation catalyst system can include an effective amount of a palladium source and an effective amount of a halide composition. Further alternative embodiments can include catalytic amounts of various inorganic co-catalyst combinations.
    Type: Grant
    Filed: April 29, 1999
    Date of Patent: December 12, 2000
    Assignee: General Electric Company
    Inventors: James Lawrence Spivack, Donald Wayne Whisenhunt, Jr., James Norman Cawse, Bruce Fletcher Johnson, Marsha Mottel Grade, Grigorii Lev Soloveichik, John Yaw Ofori, Eric James Pressman
  • Patent number: 6140294
    Abstract: A bleach and oxidation catalyst is provided comprising a catalytically ace iron, manganese or copper complex including a specified pentadentate nitrogen-containing ligand. The metal complex can activate hydrogen peroxide or peroxyacids and provides favourable stain removal properties. In addition, a considerably improved stability of these metal complex compounds in alkaline aqueous environment has been obtained, in particular at the peroxy compound concentrations generally present in the fabric washing liquor.
    Type: Grant
    Filed: November 3, 1999
    Date of Patent: October 31, 2000
    Assignee: Unilever Home & Personal Care USA, division of Conopco, Inc.
    Inventors: Michel Gilbert Delroisse, Bernard Lucas Feringa, Ronald Hage, Roelant Mathijs Hermant, Robertus Everardus Kalmeijer, Jean Hypolites Koek, Christiaan Lamers, Minze Theunis Rispens, Stephen William Russell, Ronaldus Theodorus Vliet, Jane Whittaker
  • Patent number: 6136746
    Abstract: A supported catalyst comprising a support, an anchoring agent such as an isopoly-oxymetal anion or oxometal salt thereof, and a metal complex which is useful in a wide variety on organic reactions, especially the hydrogenation of substituted .alpha.,.beta. unsaturated acids and esters, is provided. Various methods of preparing the supported catalyst of the present invention is also disclosed.
    Type: Grant
    Filed: June 11, 1998
    Date of Patent: October 24, 2000
    Assignee: Seton Hall University
    Inventors: Setrak K. Tanielyan, Robert L. Augustine
  • Patent number: 6077958
    Abstract: 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: Grant
    Filed: April 27, 1999
    Date of Patent: June 20, 2000
    Assignee: Italfarmaco Sud S.p.A.
    Inventors: Patrizia Antognazza, Tiziana Benincori, Elisabetta Brenna, Edoardo Cesarotti, Francesco Sannicolo', Licia Trimarco
  • Patent number: 6040263
    Abstract: 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: Grant
    Filed: September 15, 1998
    Date of Patent: March 21, 2000
    Assignee: Institut Francais du Petrole
    Inventors: Lothar Mussmann, Yves Chauvin, Helene Olivier
  • Patent number: 6037297
    Abstract: The invention is directed towards a metal complex having the formula LMX.sub.1 X.sub.2. L is a bidentate nitrogen-containing ligand with more than two nitrogen atoms. M is copper, silver, or gold. X.sub.1 and X.sub.2 are independently selected from the group consisting of halogens, C.sub.1 through C.sub.12 straight chain, branched, or cycloalkyl or aryl, C.sub.1 through C.sub.12 straight chain, branched, or cycloalkoxy, hydride, triflate, trifluoroacetate, trisperfluorotetraphenylborate, and tetrafluoroborate. Such metal complexes have a tetrahedral or pseudo-tetrahedral structure. The invention relates to a catalyst composition of the reaction product of the metal complex and an activating cocatalyst. The invention is also directed towards a method for forming polymers and copolymers using such catalyst compositions, especially copolymers having segments formed from olefinic monomers and monomers having at least one hydrocarbyl polar functional group.
    Type: Grant
    Filed: December 15, 1998
    Date of Patent: March 14, 2000
    Assignee: Exxon Research and Engineering Co.
    Inventors: Robert T. Stibrany, Donald N. Schulz, Smita Kacker, Abhimanyu O. Patil
  • Patent number: 5981782
    Abstract: The present invention provides a catalyst which exhibits a high catalytic activity and allows asymmetric reaction in a high asymmetric yield to obtain a reaction product having a high optical purity. The present invention also provides a process for the preparation of an optically active 4-methyl-2-oxetanone having a high optical purity useful as starting material of polymer in a high yield in a short period in the presence of the foregoing catalyst. A novel ruthenium-iodo-optically active phosphine complex is provided, represented by the following general formula (1):Ru--I.sub.2 --(R.sup.1 -BINAP) (1)wherein R.sup.1 -BINAP represents an optically active tertiary phosphine represented by the following general formula (2): ##STR1## wherein R.sup.1 represents an aryl group which may have a substituent selected from the group consisting of a C.sub.1-4 lower alkyl group, a C.sub.1-4 lower alkoxy group, a C.sub.1-4 lower alkylamino group, and a halogen atom or a C.sub.3-8 cycloalkyl group.
    Type: Grant
    Filed: November 4, 1997
    Date of Patent: November 9, 1999
    Assignee: Takasago International Corporation
    Inventors: Yoshiki Okeda, Yoji Hori, Toshimitsu Hagiwara
  • Patent number: 5981783
    Abstract: A chiral ligand system for transition or main group metal catalysts is disclosed. These ligands can be readily synthesized using inexpensive amino acids and diamines as starting materials. Several different transition or main group metals have been inserted into the ligands. The ligands have been shown to have a tetradhedral distortion that may contribute to enhanced chiral transfer from the catalyst to the substrate in chemical modifications of olefins and other reactive substrates. These catalysts have been demonstrated to be effective in catalyzing epoxidation of a variety of substrates.
    Type: Grant
    Filed: April 10, 1998
    Date of Patent: November 9, 1999
    Assignee: Polt Hill Institute
    Inventor: Robin L. Polt
  • Patent number: 5981424
    Abstract: Catalyst compositions are disclosed which are useful for the hydroxylation and the ammination of aromatic hydrocarbons using molecular oxygen as terminal oxidant. The catalysts comprise a support selected from the group consisting of metal oxides, molecular sieves, zeolites and clays; transition metal selected from the group consisting of vanadium, niobium, copper, palladium, nickel and silver, and combinations thereof; and at least one multidentate chelating, binucleating ligand. The catalysts may further comprise additional metal ions. The process is particularly suited, for example, to the one-step conversion of benzene to phenol and of benzene to aniline.
    Type: Grant
    Filed: July 31, 1997
    Date of Patent: November 9, 1999
    Assignee: Sunoco, Inc. (R&M)
    Inventors: Vincent A. Durante, Tilak P. Wijesekera, Swati Karmakar
  • Patent number: 5858905
    Abstract: Catalyst systems which comprise a transition metal and a pyrophosphite ligand are particularly effective as catalysts for hydrosilation reactions. The transition metal is from groups 7-11 of the Periodic Table, and the pyrophosphite has the following formula: ##STR1## wherein E and E' are independently a direct bond, --S--, --Se--, or --CR.sub.9 R.sub.10 -- where R.sub.9 and R.sub.10 are independently hydrogen or alkyl of 1-18 carbon atoms, and R.sub.10 can also be phenyl. R is H or methyl, R.sub.1-8 are independently H, C.sub.1-18 alkyl, C.sub.5-12 cycloalkyl, or C.sub.7-15 phenylalkyl.
    Type: Grant
    Filed: July 23, 1997
    Date of Patent: January 12, 1999
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Andrea R. Smith, Stephen D. Pastor
  • Patent number: 5841013
    Abstract: The present invention is directed toward a hydrogenation process using a highly active aromatics hydrogenation catalyst. The catalyst is prepared by decomposing a catalyst precursor selected from the group consisting of metal amine molybdates, metal amine tungstates and mixtures thereof, wherein said metal amine catalyst precursor has the general formula ML (Mo.sub.y W.sub.1-y O.sub.4).sub.a where M is Cr and/or one or more divalent promoter metals selected from the group consisting of Mn, Fe, Co, Ni, Cu and Zn; L is one or more neutral nitrogen-containing ligands at least one of which is a chelating polydentate ligand; 0.ltoreq.y.ltoreq.1; and a=1 for non-chromium containing catalysts and wherein 0.5.ltoreq.a.ltoreq.3 for chromium containing catalysts, at a temperature of about 200.degree. C. to about 400.degree. C. in an inert atmosphere; then reducing at a temperature of about 300.degree. C. to about 450.degree. C.
    Type: Grant
    Filed: May 16, 1997
    Date of Patent: November 24, 1998
    Assignee: Exxon Research and Engineering Company
    Inventors: Teh Chung Ho, Charles Ralph Symon, Viktor Buchholz, Michel Daage
  • Patent number: 5767303
    Abstract: A process for the production of a carbonic diester, wherein an alcohol is reacted in a reaction zone with carbon monoxide and oxygen in the presence of (a) metallic copper or a copper compound, (b) a heterocyclic compound containing one or more nitrogen atoms in the cyclic skeleton and (c) a glycol ether represented by the following formula (I):R.sup.1 O--(CHR.sup.2 --CH.sub.2 O).sub.n --R.sup.3 (I)wherein R.sup.1 stands for an alkyl group having from 1 to 6 carbon atoms, R.sup.2 stands for a hydrogen atom or an alkyl group having 1 or 2 carbon atoms, R.sup.3 stands for a hydrogen atom or an alkyl group having from 1 to 6 carbon atoms and n is an integer of from 1 to 12.
    Type: Grant
    Filed: June 16, 1997
    Date of Patent: June 16, 1998
    Assignee: Chiyoda Corporation
    Inventors: Takeshi Minami, Noriyuki Yoneda, Yoshimi Shiroto, Haruto Kobayashi
  • Patent number: 5750455
    Abstract: The invention concerns a catalytic composition resulting from mixing at least one aluminum halide, at least one quaternary ammonium halide and/or at least one amine halohydrate and at least one cuprous compound, preferable a halide. The invention also concerns a process for the alkylation of isoparaffins by olefins with that composition.
    Type: Grant
    Filed: October 24, 1995
    Date of Patent: May 12, 1998
    Assignee: Institut Francais Du Petrole
    Inventors: Yves Chauvin, Andre Hirschauer, Helene Olivier
  • Patent number: 5717060
    Abstract: An improved process is described for the preparation of alternating linear copolymers based on carbon monoxide and at least one compound containing an alkenyl unsaturation which comprises reacting in a liquid solvent under the operating conditions, a mixture of carbon monoxide and one or more compounds containing an alkenyl unsaturation in the presence of:(i) a catalyst having general formula (I)?Pd(chel) (chel') !.sup.++ ?A.sup.- !.sub.2 (I)wherein chel and chel' the same or different, represent a nitrogenated or phosphorated bidentate chelating agent, and A.sup.- represents an essentially non-coordinating, non esterifiable and non labile anion of an acid with pKa less than 2; and(ii) a cocatalyst having general formula (II)?chel"H.sup.+ !?A'.sup.- ! (II)wherein A'.sup.-, the same as or different from A.sup.-, has the same meaning defined above and chel" represents a nitrogenated bidentate chelating agent the same as or different from chel and chel'.
    Type: Grant
    Filed: October 31, 1996
    Date of Patent: February 10, 1998
    Assignee: Enichem S.p.A.
    Inventors: Anna Sommazzi, Fabio Garbassi, Giovanni Mestroni, Barbara Milani, Lidia Vicentini
  • Patent number: 5693585
    Abstract: A catalyst containing a porous organic or mineral support and at least one active phase having at least one aluminum halide, at least one compound selected for quaternary ammonium halides and amine hydrohalides, and at least one cuprous compound, the support having been impregnated with the active phase, the catalyst essentially constituted by particles with an average diameter in the range 0.1 .mu.m to 150 .mu.m, and the support, before impregnation with the active phase, has a total pore volume in the range 0.1 cm.sup.3 /g and 6 cm.sup.3 /g.
    Type: Grant
    Filed: June 17, 1996
    Date of Patent: December 2, 1997
    Assignee: Institut Francais du Petrole
    Inventors: Eric Benazzi, Yves Chauvin, Andre Hirschauer, Nathalie Ferrer, Helene Olivier, Jean-Yves Bernhard
  • Patent number: 5670610
    Abstract: An active catalyst in the preparation of alternating copolymers of olefins with carbon monoxide (CO) and consisting of:a) a metal salt of the group IB of the periodic table;b) a bidentate binder containing two nitrogen or phosphorous atoms capable of binding themselves to the metal atom by means of co-ordination bonds;c) a Lewis acid;d) optionally an oxidizing agent.The preparation of the catalyst is described together with its use in the alternating copolymerization of ethylene (C2) and/or other olefins with carbon monoxide.
    Type: Grant
    Filed: June 1, 1995
    Date of Patent: September 23, 1997
    Assignee: Enichem S.p.A.
    Inventors: Anna Somazzi, Gabriele Lugli, Fabio Garbassi
  • Patent number: 5556823
    Abstract: An active catalyst in the preparation of alternating copolymers of olefins with carbon monoxide (CO) and consisting of:a) a metal salt of the group IB of the periodic table;b) a bidentate binder containing two nitrogen or phosphorous atoms capable of binding themselves to the metal atom by means of co-ordination bonds;c) a Lewis acid;d) optionally an oxidizing agent.The preparation of the catalyst is described together with its use in the alternating copolymerization of ethylene (C2) and/or other olefins with carbon monoxide.
    Type: Grant
    Filed: November 28, 1994
    Date of Patent: September 17, 1996
    Assignee: Enichem S.p.A.
    Inventors: Anna Sommazi, Gabriele Lugli, Fabio Garbassi
  • Patent number: 5512696
    Abstract: A process for hydrocyanation of an aliphatic monoethylenically unsaturated compound, in which the ethylenic double bond is not conjugated to any other unsaturated group in the molecule, or a monoethylenically unsaturated compound in which the ethylenic double bond is conjugated to an ester group, which process uses a catalyst composition comprising a zero-valent and a multidentate phosphite ligand in the presence of a Lewis acid promoter.
    Type: Grant
    Filed: July 21, 1995
    Date of Patent: April 30, 1996
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Kristina A. Kreutzer, Wilson Tam
  • Patent number: 5411995
    Abstract: Xanthate, dithiocarbamate and dithiophosphate salts of transition metals, together with a coinitiator selected from organic halogen and tertiary amine compounds provide light activated initiator systems for radically polymerizable ethylenically unsaturated compounds such as (meth)acrylate esters.
    Type: Grant
    Filed: April 8, 1993
    Date of Patent: May 2, 1995
    Assignee: Loctite Corporation
    Inventor: Darchun B. Yang
  • Patent number: 5372981
    Abstract: In a preferred method, electrodes are formed with a catalyzed carbon substrate for use in an electrochemical cell. The catalyzed carbon substrate basically comprises carbon particles having internal and external surfaces defining a plethora of pores; and a pyrolyzed metal-doped copolymer material supported on the internal and external surfaces of the carbon particles. The pyrolyzed metal-doped material is a metal/nitrogen-carbon complex where the metal is complexed with the heterocarbon/nitrogen.Substrates of catalyzed carbon particles are prepared by first reacting an amine compound with formaldehyde and/or polymerized formaldehyde in solution, in the presence of a catalyst, carbon particles and a metal salt, at a temperature and at a rate of stirring sufficient to provide a polymerized product in the form of a gel. Then the gel is heated (pyrolyzed) in an inert atmosphere for a time sufficient to provide the catalytic carbon particles in the form of a powder.
    Type: Grant
    Filed: April 12, 1993
    Date of Patent: December 13, 1994
    Assignee: General Motors Corporation
    Inventor: Romeo R. Witherspoon
  • Patent number: 5369073
    Abstract: A catalyst active in the preparation of alternating olefin/carbon monoxide (CO) copolymers is constituted by:(a) at least one salt of a metal of Group IB of the Periodic System,(b) an either mono- or bidentate ligand containing one or two nitrogen or phosphorus atoms capable of linking to the copper, silver or gold atom by means of dative bonds,(c) a mineral or organic acid.Disclosed are the preparation of the catalyst and the use of said catalyst in alternated copolymerization of ethylene (C2) and/or other olefins with carbon monoxide.
    Type: Grant
    Filed: March 11, 1993
    Date of Patent: November 29, 1994
    Assignee: Enichem S.p.A.
    Inventors: Anna Sommazzi, Gabriele Lugli, Fabio Garbassi, Fausto Calderazzo
  • Patent number: 5346873
    Abstract: A catalyst active in the preparation of alternating olefin/carbon monoxide (CO) copolymers is constituted by:(a) at least one salt of a metal of Group IB of the Periodic System,(b) a mono or bidentate ligand base containing one or two nitrogen or phosphorus atoms capable of linking to the metal atom by means of dative bonds,(c) a mineral or organic oxidizer agent.Also disclosed are the preparation of the catalyst and the use of said catalyst in alternated copolymerization of ethylene (C2) and/or other olefins with carbon monoxide (CO).
    Type: Grant
    Filed: March 11, 1993
    Date of Patent: September 13, 1994
    Assignee: Enichem S.p.A.
    Inventors: Anna Sommazzi, Gabriele Lugli, Fabio Garbassi, Fausto Calderazzo
  • Patent number: 5324700
    Abstract: Carbonic acid esters are important compounds as a gasoline extender, an octane number improver, an organic solvent and a reacting agent in place of phosgene for production of isocyanates, polycarbonates and various intermediates of agricultural chemicals and pharmaceuticals.According to the present invention, carbonic acid esters can be prepared by reacting an alcohol with carbon monoxide and oxygen in the presence of a catalyst comprising a copper halide and a tertiary organophosphorus compound having phenyl group or alkyl group.
    Type: Grant
    Filed: December 31, 1992
    Date of Patent: June 28, 1994
    Assignee: JGC Corporation
    Inventors: Kenji Mori, Masao Tonosaki, Hidekazu Nakamura, Kenzo Yamamoto, Tsutomu Toida, Miki Tojima
  • Patent number: 5316994
    Abstract: An improved olefin metathesis catalyst system is disclosed. The catalyst system comprises a transition metal halide metathesis catalyst and an organo transition metal hydride co-catalyst of the formulaR.sub.x '--Cu--HThe copper hydride co-catalyst of this invention has the general formula R.sub.x '--Cu--H wherein R' is a complexing ligand preferably an organically substituted phosphine, and x is 1 or 2. The organic substituents on the phosphine group are optionally substituted C.sub.1-20 hydrocarbons, such as C.sub.1-20 alkyls or alkenyls, C.sub.3-20 cycloalkyls or cycloalkenyls having 3 to 8 carbon atoms in the ring, or optionally substituted C.sub.6-20 aryl or fused aryl. The optional substituents on the hydrocarbons include halogens, preferably chloride and fluoride; C.sub.1-6 alkyl; C.sub.1-6 alkenyl; or C.sub.1-6 alkoxy.
    Type: Grant
    Filed: December 31, 1992
    Date of Patent: May 31, 1994
    Assignee: Shell Oil Company
    Inventor: Donald R. Kelsey
  • Patent number: 5217760
    Abstract: Xanthate, dithiocarbamate and dithiophosphate salts of transition metals, together with a coinitiator selected from organic halogen and tertiary amine compounds provide light activated initiator systems for radically polymerizable ethylenically unsaturated compounds such as (meth)acrylate esters.
    Type: Grant
    Filed: July 20, 1990
    Date of Patent: June 8, 1993
    Assignee: Loctite Corporation
    Inventor: Darchun B. Yang
  • Patent number: 5102844
    Abstract: An improved process for the production of linear alternating polymers of carbon monoxide and at least one ethylenically unsaturated hydrocarbon comprises contacting the carbon monoxide and hydrocarbon under polymerization conditions in the presence of a reaction diluent and a novel catalyst composition formed from a palladium compound, a strong non-hydrohalogenic acid and a tetradentate aromatic phosphine ligand. The polymer products are of higher molecular weight and are produced at a faster rate than the more conventional process employing a catalyst composition formed from a bidentate ligand.
    Type: Grant
    Filed: May 28, 1991
    Date of Patent: April 7, 1992
    Assignee: Shell Oil Company
    Inventor: Pui K. Wong
  • Patent number: 5068310
    Abstract: An improved process for producing a polyphenylene ether with low nitrogen content and low odor properties employs, for oxidative coupling of a 2,6-disubstituted phenol, a novel catalyst comprising a copper compound, a diamine, a tertiary amine, a quaternary compound and an unsaturated compound. The new polyphenylene ether is suitable for polymer blending, with, for example, styrenic resins, to make low odor blends.
    Type: Grant
    Filed: August 23, 1990
    Date of Patent: November 26, 1991
    Assignee: General Electric Co.
    Inventor: Timothy D. Shaffer
  • Patent number: 5063196
    Abstract: Impregnated activated carbon adsorbents for the removal of toxic materials from gas streams are used in a variety of respiration and collective filter applications. The activated carbon impregnated adsorbents in the present invention remain effective in removing toxic gases and/or vapors in military, industrial and other applications, and are free of chromium and its potential health hazards. Generally, these activated carbons are comprised of an activated carbon adsorbent impregnated so as to result in an activated carbon containing 0 to 14% copper and 2 to 16% zinc, optionally supplemented according to the desired characteristics with silver, triethylenediamine, and prepared with or without the use of organic acid. The adsorbent carbons of the present invention have been found to be effective for removing a variety of toxic gases and/or vapors.
    Type: Grant
    Filed: June 23, 1989
    Date of Patent: November 5, 1991
    Assignee: Calgon Carbon Corporation
    Inventors: David T. Doughty, James E. Groose