Exactly Three Carbons Bonded Directly To The Phosphorus (e.g., Triphenylphosphines, Etc.) Patents (Class 556/21)
  • Patent number: 6750345
    Abstract: New ligands, compositions, metal-ligand complexes and arrays with pyridyl-amine ligands are disclosed that catalyze the polymerization of monomers into polymers. Certain of these catalysts with hafnium metal centers have high performance characteristics, including higher comonomer incorporation into ethylene/olefin copolymers, where such olefins are for example, 1-octene, isobutylene or styrene. Certain of the catalysts are particularly effective at polymerizing propylene to high molecular weight isotactic polypropylene in a solution process at a variety of polymerization conditions.
    Type: Grant
    Filed: November 6, 2001
    Date of Patent: June 15, 2004
    Assignee: Symyx Technologies, Inc.
    Inventors: Thomas R. Boussie, Gary M. Diamond, Christopher Goh, Keith A. Hall, Anne M. LaPointe, Margarete K. Leclerc, Cheryl Lund, Vince Murphy
  • Patent number: 6730629
    Abstract: 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: Grant
    Filed: December 10, 2002
    Date of Patent: May 4, 2004
    Assignee: Takasago International Corporation
    Inventors: Kazuhiko Matsumura, Takao Saito
  • Patent number: 6727390
    Abstract: A method of increasing the fluorous nature of a compound includes the step of reacting the compound with or tagging the compound with at least one of a second compound having the formula: wherein R is an alkyl group or an aryl group, n is 1, 2 or 3 and Rs is a spacer group and Rf is a branched fluorous group. A chemical compound having the general formula: wherein n, Rs and Rf are defined above.
    Type: Grant
    Filed: September 14, 2001
    Date of Patent: April 27, 2004
    Assignee: University of Pittsburgh
    Inventors: Dennis P. Curran, Qisheng Zhang
  • Publication number: 20040072680
    Abstract: Chiral phospholanes having biaryl chirality for applications in asymmetric catalysis are provided. A series of new chiral mono- or bidentate phosphorus ligands were efficiently prepared through a key intermediate (S)-4-chloro-4,5-dihydro-3H-4-phospha-cyclohepta[2,1-a;3,4-a′]binaphthalene and its derivatives. These ligands were complexed with transition metals to prepare catalysts, which were used in asymmetric catalytic reactions, such as, asymmetric 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 or [m+n] cycloaddition wherein m=3 to 6 and n=2.
    Type: Application
    Filed: April 25, 2003
    Publication date: April 15, 2004
    Applicant: THE PENN STATE RESEARCH FOUNDATION
    Inventor: Xumu Zhang
  • Patent number: 6720439
    Abstract: trans-RuH(&eegr;1-BH4)[(S)-xylbinap][(S,S)-dpen] (0.00125 mmol), acetophenone (5.0 mmol), and 2-propanol (2.5 mL) were placed in an autoclave, and the resulting solution was repeatedly subject 5 times to a procedure of performing pressure reduction and argon introduction while stirring the solution for deaeration. A hydrogen tank was then connected to the autoclave, and after replacing the air inside an introduction tube with hydrogen, the pressure inside the autoclave was adjusted to 5 atmospheres and then hydrogen was released until the pressure dropped to 1 atmosphere. After repeating this procedure 10 times, the hydrogen pressure was adjusted to 8 atmospheres and stirring at 25° C. was performed for 12 hours. By concentrating the solution obtained by depressurization and subjecting the crude product to simple distillation, (R)-1-phenylethanol (yield: 95%) in the form of a colorless oily substance was obtained at an ee of 99%.
    Type: Grant
    Filed: November 12, 2002
    Date of Patent: April 13, 2004
    Assignee: Nagoya Industrial Science Research Institute
    Inventors: Takeshi Ohkuma, Masatoshi Koizumi, Kilian Muñiz, Ryoji Noyori
  • Patent number: 6716787
    Abstract: A subject of the present invention is new compounds having a lanthanide and having a tridentate ligand, a process for their preparation and their use in particular as polymerization catalysts.
    Type: Grant
    Filed: December 18, 2001
    Date of Patent: April 6, 2004
    Assignees: Societe de Conseils de Recherches et d'Applications Scientifiques (S.C.R.A.S.), Centre National de la Recherche Scientifique (C.N.R.S.)
    Inventors: Anca Dumitrescu, Heinz Gornitzka, Blanca Martin-Vaca, Didier Bourissou, Guy Bertrand, Jean-Bernard Cazaux
  • Publication number: 20040054207
    Abstract: The object of the present invention is to provide a method for producing a dinuclear transition metal complex of formula (1) by reacting cyclopentadienyl ligand compound of formula (2) and substituted transition metal of formula (3).
    Type: Application
    Filed: December 11, 2002
    Publication date: March 18, 2004
    Applicant: KOREA KUMHO PETRO-CHEMICAL CO., LTD.
    Inventors: Eun-Il Kim, Seung Dai Choi
  • Patent number: 6693210
    Abstract: Provided are a novel triphenyl phosphine derivative synthesized from a triphenylphosphine and a hydroxy-containing lactone; a palladium and a nickel complexes comprising the derivative as a ligand; and a process for preparing a biaryl derivative using the complex as a catalyst. A product can be easily separated from a catalyst or a phosphorus compound, and biaryl derivative can be synthesized in a higher yield, by using the complex of the present invention as a catalyst.
    Type: Grant
    Filed: September 13, 2002
    Date of Patent: February 17, 2004
    Assignee: Mitsubishi Rayon Co., Ltd.
    Inventor: Norio Miyaura
  • Patent number: 6683198
    Abstract: A compound of formula (I) wherein X is aluminium, gallium or indium; each Y, which may be the same or different, is nitrogen or phosphorus; R1 and R2, which may be the same or different, are hydrogen, halogen or alkyl; and R3 to R7, which may be the same or different, are hydrogen or a saturated group, or R3 and R4, or R5 and R6 together represent a saturated divalent link thus completing a ring.
    Type: Grant
    Filed: February 21, 2002
    Date of Patent: January 27, 2004
    Assignee: Isis Innovation Limited
    Inventors: Anthony John Downs, Hans-Jörg Himmel
  • Patent number: 6683206
    Abstract: Compounds of formula (I), wherein R1 and R2 are, independently of one another, H, C1-C6alkyl, C1-C6halogenalkyl, C1-C6alkoxy, C1-C6alkoxy-C1-C6alkyl, or C1-C6alkoxy-C1l-C6alkyloxy, and R3 is C1-C6alkyl, are obtainable in high yields by stereoselective addition of R3-substituted propionic acid esters to R1- and R2-substituted benzaldehydes of formula R—CHO to form corresponding 3-R-3-hydroxy-2-R3-propionic acid esters, conversion of the OH group to a leavaing group, subsequent regioselective elimination to form 3-R-2-R3-propenic acid esters, and their hydrolysis to form corresponding propenic carboxylic acids and their enantioselective hydrogenation, wherein R is (a).
    Type: Grant
    Filed: January 2, 2003
    Date of Patent: January 27, 2004
    Assignee: Speedel Pharma AG
    Inventors: Stefan Stutz, Peter Herold, Felix Spindler, Walter Weissensteiner, Thomas Sturm
  • Publication number: 20030236433
    Abstract: P-chiral bisphospholane ligands and methods for their preparation are described. Use of metal/P-chiral bisphospholane complexes to catalyze asymmetric transformation reactions to provide high enantiomeric excesses of formed compounds is also described.
    Type: Application
    Filed: April 18, 2003
    Publication date: December 25, 2003
    Inventors: Garrett Stewart Hoge, Om Prakash Goel
  • Publication number: 20030225226
    Abstract: Novel reactions used to prepare phosphole and bisphosphole compounds are detailed. Novel phosphole compounds and metal coordination compounds of phosphole and bisphosphole compounds are also provided. These metal coordination compounds are useful as catalysts for the polymerization or olefins with carbon monoxide and for the polymerization of acrylic monomers.
    Type: Application
    Filed: April 11, 2003
    Publication date: December 4, 2003
    Inventors: Paul J. Fagan, George Yanwu Li, Zhibin Guan, Lin Wang
  • Patent number: 6639091
    Abstract: Bidentate ligand of formula II, R1R2M1—R—M2R3R4  (II) wherein M1 and M2 are independently P, As or Sb; R1, R2, R3 and R4 independently represent tertiary alkyl groups, or R1 and R2 together and/or R3 and R4 together represent an optionally substituted bivalent cycloaliphatic group whereby the two free valencies are linked to M1 or M2, and R represents a bivalent aliphatic bridging group containing from 2 to 6 atoms in the bridge, which is substituted with two or more substituents. A catalyst system comprising: a) a source of group VIII metal cations; b) a source of such a bidentate ligand; and c) a source of anions, and use of such a catalyst system in a process for the carbonylation of optionally substituted ethylenically or acetylenically unsaturated compounds by reaction with carbon monoxide and a coreactant is provided.
    Type: Grant
    Filed: May 17, 2001
    Date of Patent: October 28, 2003
    Assignee: Shell Oil Company
    Inventors: Eit Drent, Michael Rolf Eberhard, Paul Gerard Pringle
  • Patent number: 6635768
    Abstract: The invention relates to a complex of ruthenium of the structural formula I, where X1 and X2 are identical or different and are each an anionic ligand, R1 and R2 are identical or different and can also contain a ring, and R1 and R2 are each hydrogen or/and a hydrocarbon group, the ligand L1 is an N-heterocyclic carbene and the ligand L2 is an uncharged electron donor, in particular an N-heterocyclic carbene or an amine, imine, phosphine, phosphite, stibine, arsine, carbonyl compound, carboxyl compound, nitrile, alcohol, ether, thiol or thioether, where R1, R2, R3 and R4 are hydrogen or/and hydrocarbon groups.
    Type: Grant
    Filed: November 27, 2000
    Date of Patent: October 21, 2003
    Assignee: Degussa AG
    Inventors: Wolfgang Anton Herrmann, Wolfgang Schattenmann, Thomas Weskamp
  • Patent number: 6635779
    Abstract: A class of metallocene compounds is disclosed having general formula (I) wherein Y is a moiety of formula (II) wherein A, B, and D, same or different from each other, are selected from an element of the groups 14 to 16 of the Periodic Table of the Elements (new IUPAC version), with the exclusion of nitrogen and oxygen; R1, R2, R3, R4 and R5 are hydrogen or hydrocarbon groups, Z is selected from a moiety of formula (II) as described above and from a moiety of formula (III) wherein R6, R7, R8 and R9, are hydrogen or hydrocarbon groups; L is a divalent bridging group; M is an atom of a transition metal selected from those belonging to group 3, 4, 5, 6 or to the lanthanide or actinide groups in the Periodic Table of the Elements (new IUPAC version), X, same or different, is hydrogen, a halogen, a R10, OR10, OSO2CF3, OCOR10, SR10, NR102 or PR102 group, wherein the substituents R10 are hydrogen or alkyl groups; p is an integer of from 1 to 3, being equal to the oxidation state of the metal M minus 2.
    Type: Grant
    Filed: November 20, 2001
    Date of Patent: October 21, 2003
    Assignee: Basell Technology Company bv
    Inventors: John A. Ewen, Michael J. Elder, Robert L. Jones
  • Patent number: 6624320
    Abstract: A novel phosphine compound having excellent properties (chemical selectivity, enantioselectivity, catalytic activity) as a catalyst for asymmetric syntheses, especially asymmetric hydrogenation. A phosphine-phosphorane compound represented by the following general formula: (wherein R1 represents hydrogen atom or a linear or branched alkyl group having 1 to 4 carbon atoms, R2, R3, R4, and R5 are the same or different, and each represents hydrogen atom, or an alkyl group having 1 to 6 carbon atoms, etc., and each of R2 and R3, R3 and R4, and R4 and R5 may be together combined to form a ring which may contain one or more (preferably 1 to 2) oxygen atoms, and R6 and R7 are the same or different, and each represents a linear or branched alkyl group having 1 to 6 carbon atoms, etc.).
    Type: Grant
    Filed: November 12, 2002
    Date of Patent: September 23, 2003
    Assignee: Takasago International Corporation
    Inventors: Kazuhiko Matsumura, Takao Saito
  • Patent number: 6624321
    Abstract: The present invention relates to a process for the preparation of polyether polyols by the reaction of alkylene oxides and compounds containing active hydrogens, in the presence of specific Lewis acid metal compounds as catalysts, novel bis(perfluoroalkylsulfonic acid) compounds of Group 13 of the Periodic Table of the Elements, and to a process for the preparation thereof and the use thereof as catalysts for ring-opening polymerization of cyclic ethers.
    Type: Grant
    Filed: October 22, 2002
    Date of Patent: September 23, 2003
    Assignee: Bayer Aktiengesellschaft
    Inventors: Uwe Denninger, Jörg Hofmann, Pramod Gupta
  • Patent number: 6620955
    Abstract: Chelating ligand precursors for the preparation of olefin metathesis catalysts are disclosed. The resulting catalysts are air stable monomeric species capable of promoting various metathesis reactions efficiently, which can be recovered from the reaction mixture and reused. Internal olefin compounds, specifically beta-substituted styrenes, are used as ligand precursors. Compared to terminal olefin compounds such as unsubstituted styrenes, the beta-substituted styrenes are easier and less costly to prepare, and more stable since they are less prone to spontaneous polymerization. Methods of preparing chelating-carbene metathesis catalysts without the use of CuCl are disclosed. This eliminates the need for CuCl by replacing it with organic acids, mineral acids, mild oxidants or even water, resulting in high yields of Hoveyda-type metathesis catalysts.
    Type: Grant
    Filed: November 15, 2002
    Date of Patent: September 16, 2003
    Inventors: Richard L. Pederson, Jason K. Woertink, Christopher M. Haar, David E. Gindelberger, Yann Schrodi
  • Patent number: 6617466
    Abstract: The invention is a catalyst system including a Group IV B transition metal component and an alumoxane component which may be employed to polymerize olefins to produce a high molecular weight polymer.
    Type: Grant
    Filed: March 2, 1992
    Date of Patent: September 9, 2003
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventor: Jo Ann Marie Canich
  • Patent number: 6613910
    Abstract: The invention provides a novel method for synthesizing transition metal carbene complexes useful as olefin metathesis catalysts. The method is a convenient one-pot synthesis in which transition metal carbenes are prepared in high yield from readily available starting materials via a dihydrogen complex containing two different anionic ligands, preferably a phosphine and a heteroatom-stabilized carbene. The invention additionally provides a method for synthesizing precursors to carbene ligands useful, inter alia, in the aforementioned one-pot synthesis. The precursors are in the form of trichloromethyl adducts of the formula L1-CCl3, where L1 is a heteroatom-stabilized carbene ligand, and are prepared by contacting an unsaturated, ionized analog of L-CCl3 with a non-nucleophilic base in the presence of chloroform.
    Type: Grant
    Filed: April 2, 2002
    Date of Patent: September 2, 2003
    Assignee: California Institute of Technology
    Inventors: Robert H. Grubbs, John P. Morgan, Diego Benitez, Janis Louie
  • Publication number: 20030144137
    Abstract: 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. Processes for the preparation of the ligands are also described.
    Type: Application
    Filed: November 8, 2002
    Publication date: July 31, 2003
    Applicant: The Penn State Research Foundation
    Inventors: Xumu Zhang, Wenjun Tang
  • Patent number: 6596887
    Abstract: Provided is a process for preparing an optically active ruthenium-phosphine complex represented by the following formula (1): wherein L represents a bidentate ligand compound of a tertiary phosphine; X represents a halogen atom; and * means chiral center (L* is an optically active substance), which comprises reacting a ruthenium-phosphine complex represented by: RumXnLpAq or [RuX(D)(L)]X wherein, X and L have the same meanings as described above (L is a racemic modification); A represents triethylamine (Et3N), etc.; and m, n, p and q each stands for an integer and D represents benzene, etc. with ½ equivalent of a specific optically active chiral diamine, thereby inactivating one of the enantiomers; and then with a specific optically active diamine derivative, thereby activating the other enantiomer.
    Type: Grant
    Filed: March 14, 2001
    Date of Patent: July 22, 2003
    Assignee: Takasago International Corporation
    Inventors: Koichi Mikami, Toshinobu Korenaga, Noboru Sayo
  • Patent number: 6579997
    Abstract: 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: Grant
    Filed: July 3, 2002
    Date of Patent: June 17, 2003
    Assignee: UAB Research Foundation
    Inventors: Gary M. Gray, Maheswaran Harihara Sarma, Dale C. Smith
  • Patent number: 6576778
    Abstract: The present invention provides methods for the preparation of compounds of the formula (Formula I): LyM(CO)z wherein M is Ru or Os, each L is independently a neutral ligand, y=1-4, and z=1-5. These methods involve the reaction of Ru3(CO)12 or Os3(CO)12 with a neutral ligand in a solvent system having a boiling point higher than that of benzene at atmospheric pressure.
    Type: Grant
    Filed: August 29, 2000
    Date of Patent: June 10, 2003
    Assignee: Micron Technology, Inc.
    Inventors: Stefan Uhlenbrock, Brian A. Vaartstra
  • Patent number: 6566521
    Abstract: Bidentate phosphine ligands of the formula wherein the substituents are as defined in the specification and a process for preparing linear aldehydes by hydroformylating internal olefins using such phosphine ligands.
    Type: Grant
    Filed: November 13, 2001
    Date of Patent: May 20, 2003
    Assignee: Celanese GmbH
    Inventors: Holger Geissler, Petrus W. N. M. van Leeuwen, Paul C. J. Kamer, Lars A. van der Veen
  • Patent number: 6562989
    Abstract: The present invention is directed to a transition metal catalyst, comprising a Group 8 metal and a ligand having the structure wherein R, R′ and R″ are organic groups having 1-15 carbon atoms, n=1-5, and m=0-4. The present invention is also directed to a method of forming a compound having an aromatic or vinylic carbon-oxygen, carbon-nitrogen, or carbon-carbon bond using the above catalyst. The catalyst and the method of using the catalyst are advantageous in preparation of compounds under mild conditions of approximately room temperature and pressure.
    Type: Grant
    Filed: August 3, 2001
    Date of Patent: May 13, 2003
    Assignee: Yale University
    Inventors: John F. Hartwig, Quinetta Shelby, Noriyasu Kataoka
  • Patent number: 6559326
    Abstract: Metal complexes obtainable from a metal precursor of a metal of the 6th-10th groups of the Periodic Table in the oxidation state 0 or +2 and a ligand of the formula I, where the radicals are defined as follows: R1, R2 and R4 are hydrogen, C1-C12-alkyl groups, C3-C12-cycloalkyl groups, C6-C14-aryl groups, C2-C12-alkenyl groups, arylalkyl groups, halogens, silyl groups, C1-C12-alkoxy groups, C1-C12-thioether groups or amino groups; R3 is an &agr;-branched C3-C12-alkyl group or a substituted or unsubstituted C3-C12-cycloalkyl group, a C2-C12-alkenyl group, an arylalkyl group, a halogen, a silyl group, a C1-C12-alkoxy group, a C1-C12-thioether group or an amino group; X is oxygen, sulfur, Y is hydrogen or a silyl group, R5 to R6 are &agr;-branched C3-C12-alkyl groups or substituted or unsubstituted C3-C12-cycloalkyl groups; can be used in free form or immobilized on a solid support for the polymerization of 1-olefins.
    Type: Grant
    Filed: November 15, 2000
    Date of Patent: May 6, 2003
    Assignee: BASF Aktiengesellschaft
    Inventors: Marc Oliver Kristen, Joachim Heinicke, Wilhelm Keim, Martin Koehler, Mengzhen He
  • Patent number: 6534664
    Abstract: New ligands having a backbone comprised of NCCX can be combined with a metal or metal precursor compound or formed into a metal-ligand complex to catalyze a number of different chemical transformations, including polymerization.
    Type: Grant
    Filed: October 5, 2000
    Date of Patent: March 18, 2003
    Assignee: Symyx Technologies, Inc.
    Inventors: Anil S. Guram, Anne Marie LaPointe, Howard W. Turner, Tetsuo Uno
  • Patent number: 6525210
    Abstract: 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: Grant
    Filed: August 22, 2000
    Date of Patent: February 25, 2003
    Assignee: The Penn State Research Foundation
    Inventors: Xumu Zhang, Dengming Xiao
  • Patent number: 6518444
    Abstract: A method to synthesize a Group 15 containing metal polymerization catalyst is disclosed. The method includes an efficient high temperature synthesis of Group 15 containing ligands, especially arylamine ligands, for use in preparing polymerization catalysts and catalyst systems.
    Type: Grant
    Filed: December 18, 2000
    Date of Patent: February 11, 2003
    Assignee: Univation Technologies, LLC
    Inventors: David H. McConville, Jaimes Sher
  • Patent number: 6515084
    Abstract: Ruthenium and osmium carbene compounds that are stable in the presence of a variety of functional groups and can be used to catalyze olefin metathesis reactions on unstrained cyclic and acyclic olefins are disclosed. Also disclosed are methods of making the carbene compounds. The carbene compounds are of the formula where M is Os or Ru; R1 is hydrogen; R is selected from the group consisting of hydrogen, substituted or unsubstituted alkyl, and substituted or unsubstituted aryl; X and X1 are independently selected from any anionic ligand; and L and L1 are independently selected from any neutral electron donor. The ruthenium and osmium carbene compounds of the present invention may be synthesized using diazo compounds, by neutral electron donor ligand exchange, by cross metathesis, using acetylene, using cumulated olefins, and in a one-pot method using diazo compounds and neutral electron donors.
    Type: Grant
    Filed: December 21, 2000
    Date of Patent: February 4, 2003
    Assignee: California Institute of Technology
    Inventors: Robert H. Grubbs, Peter Schwab, Sonbinh T. Nguyen
  • Patent number: 6515156
    Abstract: The invention provides a metal complex comprising a ligand and a metal. The ligand is an aminophosphine compound represented by the following formula (1) [Each Ar represents an aryl group optionally substituted with a halogen atom, a lower alkyl group having 1 to 4 carbon atom or an alkoxy group, both Ar's being same or different with each other. R1 and R2 represent hydrogen atom, a cycloalkyl group having 5 to 7 carbon atoms, or an alkyl group having 1 to 6 carbon atom optionally substituted with a halogen atom, a lower alkoxy group or phenyl group, with R1 and R2 being same or different with each other.
    Type: Grant
    Filed: June 7, 2001
    Date of Patent: February 4, 2003
    Assignee: Takasago International Corporation
    Inventors: Sumi Kenzo, Noyori Ryoji, Ikariya Takao
  • Patent number: 6515157
    Abstract: Ferrocenyldiphosphin-ruthenium complexes are new and good catalysts for the hydrogenation of exocyclic double bond of d-Thiophene 3 to d-Thiophane 4, both of which are intermediates of D-Biotin 1 synthesis. in which R signifies —OCH3(3a), —OCH2CH3(3b), —CH2COOH(3c), CH2COOCH3(3d) or —CH2COOEt(3e) and Bz signifies benzyl group.
    Type: Grant
    Filed: June 6, 2001
    Date of Patent: February 4, 2003
    Inventors: Hong-Sun Uh, Jeong-Ho Song, Myung-Jin Lee
  • Patent number: 6504041
    Abstract: The present invention relates to the synthesis of highly active ruthenium and osmium carbene metathesis catalyst in good yield from readily available starting materials. The catalysts that may be synthesized are of the general formula wherein: M is ruthenium or osmium; X and X1 are independently any anionic ligand; L and L1 are any neutral electron donor ligand; and, R and R1 are each hydrogen or one of the following substituent groups: C2-C20 alkenyl, C2-C20 alkynyl, C1-C20 alkyl, aryl, C1-C20 carboxylate, C1-C20 alkoxy, C2-C20 alkenyloxy, C2-C20 alkynyloxy, aryloxy, C2-C20 alkoxycarbonyl, C1-C20 alkylthio, C1-C20 alkylsulfonyl and C1-C20 alkylsulfinyl. Optionally, the substituent group may be substituted with one or more groups selected from C1-C5 alkyl, halogen, C1-C5alkoxy, and aryl. When the substitute aryl group is phenyl, it may be further substituted with one or more groups selected from a halogen, a C1-C5 alkyl, or a C1-C5 alkoxy.
    Type: Grant
    Filed: September 28, 2001
    Date of Patent: January 7, 2003
    Assignee: California Institute of Technology
    Inventors: Robert H. Grubbs, Tomas R. Belderrain, Seth N. Brown, Thomas E. Wilhelm
  • Patent number: 6455720
    Abstract: A novel 2,2-(diaryl)vinylphosphine compound represented by the following general formula (1): (wherein R1 is a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, an alicyclic group having 5 to 7 carbon atoms, etc.; R2, R3, R4, R5, R6, and R7 may be the same or different and each is an alkyl group having 1 to 6 carbon atoms, an alicyclic group having 5 to 7 carbon atoms, etc., provided that R4 and R5 taken together and/or R6 and R7 taken together may represent a fused benzene ring, a substituted fused benzene ring, a trimethylene group, etc.; and p, q, r, and s each is 0 to 5, provided that p+q and r+s each is in the range of from 0 to 5); a palladium-phosphine catalyst obtained by causing a palladium compound to act on the novel 2,2-(diaryl)vinylphosphine compound; and a process for obtaining an arylamine, a diaryl and an arylalkyne in the presence of the palladium-phosphine catalyst.
    Type: Grant
    Filed: June 27, 2001
    Date of Patent: September 24, 2002
    Assignee: Takasago International Corporation
    Inventors: Ken Suzuki, Tohru Kobayashi, Takenobu Nishikawa, Yoji Hori, Toshimitsu Hagiwara
  • Patent number: 6444833
    Abstract: A class of metallocene compounds is disclosed having the general formula (I): wherein Y is a moiety of formula (II) wherein A, B and D, same or different from each other, are selected from an element of the groups 14 to 16 of the Periodic Table of the Elements (new IUPAC version), with the exclusion of nitrogen and oxygen; R1, R2, R3, R4 and R5 are hydrogen or hydrocarbon groups, Z is selected from a moiety of formula (II) as described above and from a moiety of formula (III): wherein R6, R7, R8 and R9, are hydrogen or hydrocarbon groups; L is a divalent bridging group; M is an atom of a transition metal selected from those belonging to group 3, 4, 5, 6 or to the lanthanide or actinide groups in the Periodic Table of the Elements (new IUPAC version), X, same or different, is hydrogen, a halogen, a R10, OR10, OSO2CF3, OCOR10, SR10, NR102 or PR102 group, wherein the substituents R10 are hydrogen or alkyl groups; p is an integer of from 0 to 3, being equal to
    Type: Grant
    Filed: December 15, 1999
    Date of Patent: September 3, 2002
    Assignee: Basell Technology Company BV
    Inventors: John A. Ewen, Michael J. Elder, Robert L. Jones
  • Patent number: 6437161
    Abstract: Substituted monocyclopentadienyl, monoindenyl, monofluorenyl and heterocyclopentadienyl complexes of chromium, molybdenum or tungsten in which at least one of the substituents on the cyclopentadienyl ring carries a donor function which is bonded rigidly, not exclusively via sp3-hybridized carbon or silicon atoms, and a process for the polymerization of olefins.
    Type: Grant
    Filed: August 13, 1999
    Date of Patent: August 20, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Shahram Mihan, Dieter Lilge, Paulus de Lange, Günther Schweier, Martin Schneider, Ursula Rief, Udo Handrich, Johannes Hack, Markus Enders, Gunter Ludwig, Ralph Rudolph
  • Patent number: 6423794
    Abstract: Complexes of certain transition metals with certain phosphorous-nitrogen bidentate ligands are part of all of catalyst systems for the polymerization of ethylene. Under certain polymerization conditions novel, highly branched, homopolyethylenes may be produced.
    Type: Grant
    Filed: March 31, 2000
    Date of Patent: July 23, 2002
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Zhibin Guan
  • Patent number: 6420583
    Abstract: This invention is directed to a method for synthesizing a carbonyl based compound under neat conditions comprising refluxing a metal carbonyl compound with an excess of neutral ligand to produce a first mixture; evaporating any excess neutral ligand from the first mixture to produce a second mixture; and distilling the second mixture to produce the carbonyl based compound.
    Type: Grant
    Filed: September 27, 2001
    Date of Patent: July 16, 2002
    Assignee: Praxair Technology, INC
    Inventors: Michael Alexander Lienhard, Cynthia A. Hoover
  • Patent number: 6388130
    Abstract: The invention provides a metal complex comprising a ligand and a metal. The ligand is an aminophosphine compound represented by the following formula (1) The metal is rhodium, ruthenium, iridium or nickel.
    Type: Grant
    Filed: June 7, 2001
    Date of Patent: May 14, 2002
    Assignee: Takasago International Corporation
    Inventors: Sumi Kenzo, Noyori Ryoji, Ikariya Takao
  • Patent number: 6380412
    Abstract: The present invention relates to optically active diphosphines. It is also targeted at their preparation according to a process for the resolution of the racemic mixture of the said phosphines to optically active isomers. The subject of the invention is new optically active bis[1-phospha-2,3-diphenyl-4,5-dimethylnorbornadiene] diphosphines and a process for resolving the racemic bis[1-phospha-2,3-diphenyl-4,5-dimethylnorbornadiene] mixture which comprises reacting it with a palladium or platinum complex as chiral auxiliary in an organic solvent, thus forming diastereoisomer complexes, and then resolving the said optically pure complexes. The invention also relates to new optically active metal complexes comprising the said phosphines and to their use in a process for the preparation of optically active carboxylic acids and/or derivatives according to a process for the hydrogenation of &agr;,&bgr;-unsaturated carboxylic acids and/or derivatives.
    Type: Grant
    Filed: February 4, 2000
    Date of Patent: April 30, 2002
    Assignee: Rhone-Poulenc Chimie
    Inventors: Francois Mathey, Frédéric Robin, Francois Mercier, Michel Spagnol
  • Patent number: 6376690
    Abstract: The present invention generally relates to the discovery that the solubility of metal complexes may be readily manipulated by the addition of one or more solubility-enhancing compounds. This manipulation of the solubilities allows for the preparation of suitable samples for precise quantitative analysis and for the facile purification of the desired products from the reaction mixture containing one or more metal complexes. In one embodiment of the invention, the relative solubilities between two solutions are manipulated so as cause the metal complex found in a first solution to transfer to a second solution that is generally immiscible with the first solution. The metal complex is thus separated from the reaction mixture which comprises the first solution by the removal of the second solution.
    Type: Grant
    Filed: August 30, 1999
    Date of Patent: April 23, 2002
    Assignee: California Institute O Technology
    Inventors: Robert H. Grubbs, Heather D. Maynard, David M. Lynn
  • Patent number: 6359165
    Abstract: Enantiomerically pure &bgr;-hydroxy esters are prepared by a process in which &bgr;-keto esters are reacted with hydrogen in the presence of catalysts of the formula LRuX2 where X is halogen, acetate, allyl, methallyl, 2-phenylallyl, perchlorate, trifluoroacetate, tetrafluoroborate, hexafluoroantimonate, hexafluorophosphate, hexafluoroarsenate or trichloroacetate, L is a bidentate phospholane of the formula I  where B=a bridging link with 1-5 carbon atoms between the two phosphorus atoms, R1=H, C1-C6-alkyl, aryl, alkylaryl or SiR23, R2=alkyl or aryl, m=0 or 1, R3=H or OR4, and R4=R1, with the proviso that if m=1 then R3=H and if m=0 then R3 ≠ H.
    Type: Grant
    Filed: September 29, 1999
    Date of Patent: March 19, 2002
    Assignee: BASF Aktienegesellschaft
    Inventors: Rainer Stürmer, Martin Jochen Klatt, Armin Börmer, Jens Holz, Gudrun Voss
  • Patent number: 6348611
    Abstract: 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: Grant
    Filed: August 25, 1999
    Date of Patent: February 19, 2002
    Assignee: Samsung Electronic Co., Ktd.
    Inventors: Byeong-No Lee, Duck-Joo Yang, Young-Hun Byun
  • Patent number: 6342621
    Abstract: Penta-coordinated ruthenium catalysts for the metathesis reactions of olefins, in particular ring opening metathesis polymerization (ROMP) of cyclo-olefin monomers, which are cationic complexes represented by formula I, II or III: wherein each of X1 and X2, which may be the same or different, is an optionally substituted C3-C20 hydrocarbon group having an allyl moiety as an end group bonded to the ruthenium atom, or X1 and X2 together form a group, optionally substituted, which results from dimerization of an alkene and has at each end an allyl group bonded to the ruthenium atom; L1 and L2 are mono-dentate neutral electron donor ligands, preferably highly sterically encumbered neutral electron donor ligands such as alkyl phosphines or amines; L{circumflex over ( )}L is a bidentate neutral electron donor ligand, preferably phosphine, amino, imino, arsine or arphos; L3 is a solvent molecule or a neutral mono-dentate electron donor ligand; L{circumflex over ( )}L{circumflex over ( )}L is a trid
    Type: Grant
    Filed: January 27, 2000
    Date of Patent: January 29, 2002
    Assignee: Nippon Zeon Co., Ltd.
    Inventors: Shakti L. Mukerjee, Vernon L. Kyllingstad
  • Patent number: 6342605
    Abstract: Bidentate phosphine ligands of the formula wherein the substituents are as defined in the specification and a process for preparing linear aldehydes by hydroformylating internal olefins using such phosphine ligands.
    Type: Grant
    Filed: August 18, 1999
    Date of Patent: January 29, 2002
    Assignee: Celanese GmbH
    Inventors: Holger Geissler, Petrus W. N. M. van Leeuwen, Paul C. J. Kamer, Lars A. van der Veen
  • Patent number: 6339157
    Abstract: Aldehydes are catalytically combined with amines to form carboxamides in one step using an oxidant and a metal-ligand complex or metal/ligand composition.
    Type: Grant
    Filed: July 28, 2000
    Date of Patent: January 15, 2002
    Assignee: Symyx Technologies, Inc.
    Inventors: Xiaohong Bei, Anil Guram
  • Patent number: 6339174
    Abstract: A catalyst composition comprising a) more than 70% by weight of a polyethylene glycol of the formula H—(OCH2—CH2)n—OH, where n is an integer of 3 to 16 and the number average molecular weight is less than 650 b) rhodium in elemental form or bound form and c) 2 to 25% by weight of water soluble sulfonated triarylphosphine ligand having 1 to 2 phophorus atoms and not more than 25% by weight of water based on the total amount of the catalyst and its use for the hydroformylation of olefins to aldehydes is described.
    Type: Grant
    Filed: May 16, 2000
    Date of Patent: January 15, 2002
    Assignee: Celanese Chemicals Europe GmbH
    Inventor: Sandra Bogdanovic
  • Patent number: 6333291
    Abstract: This invention provides a novel diphosphine compound which is useful as a ligand of catalysts for asymmetric synthesis reactions, particularly asymmetric hydrogenation reaction. Particularly, it provides a diphosphine compound represented by a general formula (1): wherein R1 and R2 each independently represents a cycloalkyl group, an unsubstituted or substituted phenyl group or a five-membered aromatic heterocycle residue.
    Type: Grant
    Filed: October 30, 2000
    Date of Patent: December 25, 2001
    Assignee: Takasago International Corporation
    Inventors: Tohru Yokozawa, Noboru Sayo, Takao Saito, Takero Ishizaki
  • Patent number: RE37573
    Abstract: Process for the preparation of an olefin polymer using metallocenes containing specifically substituted indenyl ligands A highly effective catalyst system for the polymerization of olefins comprises a cocatalyst, preferably an aluminoxane, and a metallocene of the formula I in which, preferably M1 is Zr or Hf, R1 and R2 are alkyl or halogen, R5 is hydrogen or alkyl, R3 and R4 are alkyl, where R3, R4 and R5 may be halogenated, —(CR7R8)m—R6—(CR7R8)n— is a single- or multi-membered chain in which R6 may also be a (substituted) heteroatom, and m+n is zero or 1.
    Type: Grant
    Filed: February 19, 1999
    Date of Patent: March 5, 2002
    Assignee: Basell Polyolefin GmbH
    Inventors: Andreas Winter, Frank Kueber, Walter Spaleck, Herbert Riepl, Wolfgang A. Herrmann, Volker Dolle, Juergen Rohrmann