Exactly Three Carbons Bonded Directly To The Phosphorus (e.g., Triphenylphosphines, Etc.) Patents (Class 556/21)
  • Patent number: 6323353
    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: December 23, 1999
    Date of Patent: November 27, 2001
    Assignee: Takasago International Corporation
    Inventors: Kenzo Sumi, Ryoji Noyori, Takao Ikariya
  • Patent number: 6313332
    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-C5 alkoxy, and aryl. When the substitute aryl group is phenyl, it may be further substituted witn one or more groups selected from a halogen, a C1-C5 alkyl, or a C1-C5 alkoxy.
    Type: Grant
    Filed: September 28, 2000
    Date of Patent: November 6, 2001
    Assignee: California Institute of Technology
    Inventors: Robert H. Grubbs, Tomas R. Belderrain, Seth N. Brown, Thomas E. Wilhelm
  • Patent number: 6306988
    Abstract: A method for the cross-metathesis of terminal olefins is disclosed. The method describes making disubstituted internal olefin products by contacting a first terminal olefin with another first terminal olefin to form a dimer and then contacting the dimer with a second terminal olefin in the presence of a catalyst having the formula where M may be Os or Ru, R and R1 may be the same or different and may be hydrogen or a substitutent group selected from C1-C20 alkyl, C2-C20 alkenyl,C2-C20 alkynyl, 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. X and X1 may be the same or different and may be any anionic ligand. L and L1 may be the same or different and may be any neutral electron donor.
    Type: Grant
    Filed: January 26, 2000
    Date of Patent: October 23, 2001
    Assignee: California Institute of Technology
    Inventors: Robert H. Grubbs, Daniel J. O'Leary, Helen E. Blackwell
  • Patent number: 6288253
    Abstract: Dendrimers were directly and covalently attached to solid supports via siloxy bonds. After complexation with transition metals, the dendrimers were used as catalysts. The supported dendrimers were stable and easily separated from the reaction mixture.
    Type: Grant
    Filed: July 9, 1999
    Date of Patent: September 11, 2001
    Assignees: DuPont Canada Inc., National Research Council, The University of Ottawa
    Inventors: Leo E. Manzer, Prabhat Arya, Howard Alper, Sheila Christine Bourque, Gary Jefferson
  • Patent number: 6277934
    Abstract: An organic aluminoxy compound which shows 27Al nuclear magnetic resonance spectrum (27Al-NMR spectrum) having an A1/A2 ratio of at most 0.1, wherein A1 is area of a region encompassed by a segment of a line which connects a local minimum point existing between a continuous curve “a” containing a peak appearing at around 150 ppm and a continuous curve “b” containing a peak appearing at around 60 ppm to the point where the above curve “b” comes into contact with the base line and also by the above curve “b” and A2 is area of a region encompassed by the above curves “a” and “b” and also by the base line; an organic aluminoxy compound containing at least 5%, expressed in terms of aluminum atom, of a portion insoluble in a mixed solvent of toluene and hexane in a ratio by volume of 2:5 at 30° C. or lower; and a catalyst for producing a polymer comprising any of the above organic aluminoxy compounds and a transition metal compound.
    Type: Grant
    Filed: October 13, 1999
    Date of Patent: August 21, 2001
    Assignee: Idemitsu Petrochemical Co., Ltd.
    Inventors: Tsuyoshi Kondoh, Shoji Naganuma, Norio Tomotsu
  • Patent number: 6268513
    Abstract: The present invention discloses new efficient processes for various bond forming reactions, including Suzuki reactions and aryl aminations. Organic compounds (e.g., ligands), their metal complexes and compositions using those compounds, provide useful catalysts. The invention also relates to performing Suzuki cross coupling reactions with unreactive aryl-chlorides.
    Type: Grant
    Filed: August 20, 1999
    Date of Patent: July 31, 2001
    Assignee: Symyx Technologies, Inc.
    Inventors: Anil Guram, Xiaohong Bei
  • Patent number: 6265601
    Abstract: The present invention discloses new efficient processes for various bond forming reactions, including Suzuki reactions. Organic compounds (e.g., ligands), their metal complexes and compositions using those compounds, provide useful catalysts. The invention also relates to performing Suzuki cross coupling reactions with unreactive aryl-chlorides.
    Type: Grant
    Filed: April 22, 1999
    Date of Patent: July 24, 2001
    Assignee: Symyx Technologies, Inc.
    Inventors: Anil Guram, Xiaohong Bei
  • Patent number: 6232482
    Abstract: Ruthenium complexes of the formula I or IV RuX2(═CH—CH2R)L1L2  (I) RuXY(═CH═CH2R)L1L2  (IV) where X, Y are anionic ligands, R is hydrogen or a substituted or unsubstituted C1-C20-alkyl radical or C6-C20-aryl radical and L1 and L2 are, independently of one another, uncharged electron donor ligands, are prepared by (a) reaction of RuX3 with L1 and L2 in an inert solvent in the presence of a reducing agent and hydrogen and (b) reaction with compounds of the formula II R—C≡CH  (II) where R is as defined above, in the presence or absence of water, and, if desired after isolation of the intermediate, with HY, [HL1]Y or [HL2]Y.
    Type: Grant
    Filed: May 8, 2000
    Date of Patent: May 15, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Schwab, Michael Schulz, Justin Wolf, Wolfram Stuer, Helmut Werner
  • Patent number: 6232483
    Abstract: Certain nickel [II] complexes of selected ortho-phosphine substituted arylsulfonamides or selected phosphine containing alkylsulfonamides catalyze the polymerization of ethylene. The polymers produced may be used as lubricants or in waxes. Some of these nickel [II] complexes and the phosphine containing ligands are also novel compounds.
    Type: Grant
    Filed: November 18, 1999
    Date of Patent: May 15, 2001
    Assignee: E. I. du Pont Nemours and Company
    Inventors: Jordan Lawrence Bennett, Maurice S. Brookhart, III, Lynda Kaye Johnson, Christopher Moore Killian
  • Patent number: 6225487
    Abstract: A new ligand having a backbone comprised of PCCC, where the last carbon atom is sp3 hybridized 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 C—N bond formation.
    Type: Grant
    Filed: April 17, 1998
    Date of Patent: May 1, 2001
    Assignee: Symyx Technologies, Inc.
    Inventor: Anil Guram
  • Patent number: 6218559
    Abstract: Reaction products of an iridium(III) salt or a hydrate thereof, a diphosphine having secondary phosphine groups and a metal or ammonium chloride, bromide or iodide are excellent hydrogenation catalysts for ketimine. Using chiral diphosphines and prochiral ketimines, diastereoisomeric secondary amines are obtained in high optical yields.
    Type: Grant
    Filed: March 11, 1999
    Date of Patent: April 17, 2001
    Assignee: Novaritis Corporation
    Inventors: Felix Spindler, Ulrich Pittelkow
  • Patent number: 6211391
    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: September 20, 1999
    Date of Patent: April 3, 2001
    Assignee: California Institute of Technology
    Inventors: Robert H. Grubbs, Peter Schwab, Sonbinh T. Nguyen
  • Patent number: 6191063
    Abstract: 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 re
    Type: Grant
    Filed: July 1, 1999
    Date of Patent: February 20, 2001
    Assignee: Celanese GmbH
    Inventors: Sandra Bogdanovic, Carl-Dieter Frohning, Helmut Bahrmann, Matthias Beller, Steffen Haber, Hans-Jerg Kleiner
  • Patent number: 6177528
    Abstract: Novel aminomethylphosphine ligands have particular substituents on the central carbon atom. Such ligands form coordination complexes that may be catalysts for the polymerization of monomers or other catalytic induced reactions.
    Type: Grant
    Filed: December 14, 1999
    Date of Patent: January 23, 2001
    Assignee: Symyx Technologies, Inc.
    Inventors: Anne Marie LaPointe, Anil Guram, Timothy S. Powers, Bernd Jandeleit, Thomas Boussie, Cheryl Lund
  • Patent number: 6153776
    Abstract: Group 3-6 or Lanthanide metal complexes possessing two metal centers, catalysts derived therefrom by combining the same with strong Lewis acids, Bronsted acid salts, salts containing a cationic oxidizing agent or subjected to bulk electrolysis in the presence of compatible, inert non-coordinating anions and the use of such catalysts for polymerizing olefins, diolefins and/or acetylenically unsaturated monomers are disclosed.
    Type: Grant
    Filed: August 28, 1998
    Date of Patent: November 28, 2000
    Assignee: The Dow Chemical
    Inventors: Jasson T. Patton, Tobin J. Marks, Liting Li
  • Patent number: 6153778
    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 ##STR1## wherein: M is ruthenium or osmium;X and X.sup.1 are independently any anionic ligand;L and L.sup.1 are any neutral electron donor ligand; and,R and R.sup.1 are each hydrogen or one of the following substituent groups: C.sub.2 -C.sub.20 alkenyl, C.sub.2 -C.sub.20 alkynyl, C.sub.1 -C.sub.20 alkyl, aryl, C.sub.1 -C.sub.20 carboxylate, C.sub.1 -C.sub.20 alkoxy, C.sub.2 -C.sub.20 alkenyloxy, C.sub.2 -C.sub.20 alkynyloxy, aryloxy, C.sub.2 -C.sub.20 alkoxycarbonyl, C.sub.1 -C.sub.20 alkylthio, C.sub.1 -C.sub.20 alkylsulfonyl and C.sub.1 -C.sub.20 alkylsulfinyl. Optionally, the substituent group may be substituted with one or more groups selected from C.sub.1 -C.sub.5 alkyl, halogen, C.sub.1 -C.sub.5 alkoxy, and aryl.
    Type: Grant
    Filed: March 10, 2000
    Date of Patent: November 28, 2000
    Assignee: California Institute of Technology
    Inventors: Robert H. Grubbs, Tomas R. Belderrain, Seth N. Brown, Thomas E. Wilhelm
  • Patent number: 6147238
    Abstract: Process for the preparation of octa-2,7-dienyl-1-amine by telomerization of butadiene with ammonia in a two-phase system in the presence of hydrophilic palladium complexes, characterized in that octa-2,7-dienyl-1-amine and octa-1,7-dienyl-3-amine are isolated separately from one another from the reaction mixture present after telomerization, and the octa-1,7-dienyl-3-amine isolated in this way is subjected to an isomerization reaction to form octa-2,7-dienyl-1-amine, and also novel triphenylphosphine mono- and dimethoxytri(sodium sulphonates) and the use of triphenylphosphine trimethoxytri(sodium sulphonates), triphenylphosphine trimethyltri(sodium sulphonates) and triphenylphosphine trifluorodi- and tri(sodium sulphonates) as ligands for the preparation of palladium complexes.
    Type: Grant
    Filed: February 24, 2000
    Date of Patent: November 14, 2000
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Joachim Traenckner, Jorg-Dietrich Jentsch, Thomas Prinz, Birgit Driessen-Holscher, Wilhelm Keim
  • Patent number: 6136222
    Abstract: Nitrogen-absorbing and -desorbing compositions, novel ligands and transition metal complexes, and methods of using the same, which are useful for the selective separation of nitrogen from other gases, especially natural gas.
    Type: Grant
    Filed: April 11, 1996
    Date of Patent: October 24, 2000
    Assignee: Bend Research, Inc.
    Inventors: Dwayne T. Friesen, Walter C. Babcock, David J. Edlund, David K. Lyon, Warren K. Miller
  • Patent number: 6127563
    Abstract: Disclosed is a process for preparing bridged Group 4 metal complexes containing a neutral diene ligand starting from the corresponding novel, metal diene containing complexes by reaction thereof with the divalent derivative of a bridged bidentate ligand compound. The novel, intermediate metal diene complexes, their formation from tetravalent metal salts and an integrated process combining both process steps are claimed.
    Type: Grant
    Filed: October 20, 1999
    Date of Patent: October 3, 2000
    Assignee: The Dow Chemical Company
    Inventors: Eugene Y. Chen, David D. Devore, Richard E. Campbell, Jr., D. Patrick Green, Jasson T. Patton, Jorge Soto, David R. Wilson
  • Patent number: 6124476
    Abstract: The present invention discloses new organic compounds (e.g., ligands), their metal complexes and compositions using those compounds. The invention also relates to the field of catalysis. In particular, this invention relates to new compounds which when combined with suitable metals or metal precursor compounds provide useful catalysts for various bond-forming reactions, including Suzuki cross-coupling reactions. The invention also relates to performing Suzuki cross coupling reactions with unreactive aryl-chlorides.
    Type: Grant
    Filed: February 18, 1999
    Date of Patent: September 26, 2000
    Assignee: Symyx Technologies, Inc.
    Inventors: Anil Guram, Xiaohong Bei, Timothy S. Powers, Bernd Jandeleit, Thomas Crevier
  • Patent number: 6118013
    Abstract: Metal complexes useful as components of addition polymerization catalysts are prepared by oxidizing Group 4 or Lanthanide metal containing complexes using an organic halide oxidizing agent in a unique one electron oxidation.
    Type: Grant
    Filed: April 29, 1999
    Date of Patent: September 12, 2000
    Assignee: The Dow Chemical Company
    Inventor: David D. Devore
  • Patent number: 6114557
    Abstract: The present invention provides methods for the preparation of compounds of the formula (Formula I):L.sub.y M(CO).sub.zwherein 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 Ru.sub.3 (CO).sub.12 or Os.sub.3 (CO).sub.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 11, 1999
    Date of Patent: September 5, 2000
    Assignee: Micron Technology, Inc.
    Inventors: Stefan Uhlenbrock, Brian A. Vaartstra
  • Patent number: 6111121
    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 ##STR1## where M is Os or Ru; R.sup.1 is hydrogen; R is selected from the group consisting of hydrogen, substituted or unsubstituted alkyl, and substituted or unsubstituted aryl; X and X.sup.1 are independently selected from any anionic ligand; and L and L.sup.1 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: January 15, 1998
    Date of Patent: August 29, 2000
    Assignee: California Institute of Technology
    Inventors: Robert H. Grubbs, Peter Schwab, Sonbinh T. Nguyen
  • Patent number: 6107502
    Abstract: A method for purifying a transition metal compound, which comprises conducting crystallization of a transition metal compound from a solution containing the transition metal compound while stirring.According to the present invention, it is possible to purify and produce efficiently a transition metal compound at high purity under industrially and economically advantageous conditions.
    Type: Grant
    Filed: October 9, 1998
    Date of Patent: August 22, 2000
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masaaki Nabika, Kotohiro Nomura
  • Patent number: 6107420
    Abstract: The present invention generally relates to the use of certain ruthenium and osmium complexes that are substantially inactive at a first temperature (preferably about room temperature) but become progressively more active at a higher second temperature. This difference in reactivities allows the reaction mixture to be formed and manipulated at the first temperature until polymerization is desired. When appropriate, the reaction mixture is heated to a suitable temperature (preferably greater than 50.degree. C.) to activate the catalyst and to initiate polymerization. Because both the initiation and the rate of polymerization may be controlled with temperature, the inventive methods are especially suitable for ring opening metathesis polymerization ("ROMP") reactions and for molding polymer articles that require extended pot-lives.
    Type: Grant
    Filed: July 26, 1999
    Date of Patent: August 22, 2000
    Assignee: California Institute of Technology
    Inventors: Robert H. Grubbs, Thomas E. Wilhelm
  • Patent number: 6103920
    Abstract: Disclosed herein is a process for the polymerization of ethylene, norbornenes and styrenes, by contacting in solution a selected nickel compound and a selected compound which is or can coordinated to the nickel with the olefin(s). The polymers produced are useful for films and molding resins.
    Type: Grant
    Filed: July 23, 1997
    Date of Patent: August 15, 2000
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Lynda Kaye Johnson, Jerald Feldman, Kristina Ann Kreutzer, Stephan James Mclain, Alison Margaret Anne Bennett, Edward Bryan Coughlin, Dennis Scott Donald, Lissa Taka Jennings Nelson, Anju Parthasarathy, Xing Shen, Wilson Tam, Yueli Wang
  • Patent number: 6100414
    Abstract: Disclosed are novel cyclopentadienyl transition metal compounds that are stable under a wide variety of conditions, particularly under conditions that include exposure to water and oxygen containing media. These novel compounds can be utilized in preparing novel catalyst systems useful in polymerizing olefins. The cyclopentadienyl compound can specifically be [(C5H4CH2CH2N[H]Me2)TiCl3]+B[C6F5]4-. Also disclosed are processes for preparing the novel cyclopentadienyl transition metal compounds.
    Type: Grant
    Filed: April 2, 1998
    Date of Patent: August 8, 2000
    Assignee: Eastman Chemical Company
    Inventors: Robert Tan Li, Laughlin Gerard McCullough
  • Patent number: 6096913
    Abstract: In a process for the synthesis of a first metal-ligand complex, M.sup.+n (L.sup.-).sub.n, where n.gtoreq.1, from a metal compound precursor and a ligand precursor, where the metal of the metal compound precursor may during the synthesis change to a valence in excess of n; the improvement, to suppress formation of a second metal-ligand complex of the metal with a valence in excess of n, of adding the elemental form of the metal to the synthesis of the first metal-ligand complex.
    Type: Grant
    Filed: June 10, 1999
    Date of Patent: August 1, 2000
    Assignee: Air Products and Chemicals, Inc.
    Inventors: John Anthony Thomas Norman, Yoshihide Senzaki, David Allen Roberts
  • Patent number: 6090739
    Abstract: The present invention relates to a transition metal compound of the formula I ##STR1## where M.sup.1 is a metal of group IIIb, IVb or Vb of the Periodic Table of the Elements,R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are identical or different and are each a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.40 -hydrocarbon-containing group, an --SiR.sup.5.sub.3, --NR.sup.5.sub.2, --Si(OR.sup.5).sub.3, --Si(SR.sup.5).sub.3 or --PR.sup.5.sub.2 radical, where R.sup.5 are identical or different and are each a halogen atom, a C.sub.1 -C.sub.10 -alkyl group or a C.sub.6 -C.sub.10 -aryl group, or two or more radicals R.sup.1, R.sup.2, R.sup.3 or R.sup.4 together with the atoms connecting them form a ring system,Y are identical or different and are each a hydrogen atom, a C.sub.1 -C.sub.40 -hydrocarbon-containing group, an OH group, a halogen atom or an NR.sup.5.sub.2 group,k is an integer which corresponds to the valence of the transition metal atom M.sup.1 minus two and if Y is a butadiene unit, k is 1,A is a bridge,R.
    Type: Grant
    Filed: June 18, 1997
    Date of Patent: July 18, 2000
    Assignee: Targor GmbH
    Inventors: Michael Riedel, Gerhard Erker, Lothar Duda
  • Patent number: 6084114
    Abstract: The invention relates to palladaphosphacyclobutanes of the formula (I) ##STR1## where R.sup.1, R.sup.2 are, independently of one another, hydrogen, (C.sub.1 -C.sub.4)-alkyl, (C.sub.3 -C.sub.12)-cycloalkyl, (C.sub.1 -C.sub.4)-alkoxy, fluorine, N[(C.sub.1 -C.sub.4)-alkyl].sub.2, CO.sub.2 -(C.sub.1 -C.sub.4)-alkyl, OCO-(C.sub.1 -C.sub.4)-alkyl or aryl;R.sup.3, R.sup.4, R.sup.5, R.sup.6 are, independently of one another, (C.sub.1 -C.sub.8)-alkyl, (C.sub.3 -C.sub.12)-cycloalkyl or aryl;or where R.sup.1 and R.sup.2, R.sup.1 or R.sup.2 and R.sup.3 or R.sup.4, R.sup.3 and R.sup.4, R.sup.3 or R.sup.4 and R.sup.5 or R.sup.6, or R.sup.5 and R.sup.6 together form an aliphatic ring; or where R.sup.5 and R.sup.6, R.sup.3 or R.sup.4 and R.sup.5 or R.sup.6 together form an aromatic ring; andY is an anion of an inorganic or organic acid, with the exception of the compoundsdi-.mu.-chloro-bis[2-[bis(1,1-dimethylethyl)phosphino]-2-methylpropyl-C,P]d ipalladium(II)di-.mu.
    Type: Grant
    Filed: July 19, 1999
    Date of Patent: July 4, 2000
    Assignee: Aventis Research & Technologies GmbH & Co. KG
    Inventors: Holger Geissler, Peter Gross, Bianca Guckes
  • Patent number: 6084113
    Abstract: In a process for the telomerization of dienes with nucleophiles in a liquid two-phase system, use is made as catalysts of complexes comprising a transition metal as central atom and at least one tris-(hydroxyalkyl)-phosphine or -phosphine oxide as ligand. The use as catalysts of compounds comprising a transition metal as central atom and at least one tris-(hydroxy-C.sub.2 -C.sub.5 -alkyl)-phosphine or -phosphine oxide as ligand, new compounds of this type and aqueous solutions of such compounds are likewise described.
    Type: Grant
    Filed: July 22, 1998
    Date of Patent: July 4, 2000
    Assignee: Bayer Aktiengesellschaft
    Inventors: Birgit Driessen-Holscher, Wilhelm Keim, Thomas Prinz, Hans-Joachim Traenckner, Jorg-Dietrich Jentsch
  • Patent number: 6069264
    Abstract: The present invention relates to a transition metal compound of the formula I ##STR1## where M.sup.1 is a transition metal of group IIIb, IVb, Vb or VIb of the Periodic Table of the Elements,Y are identical or different and are each a hydrogen atom, an OH group, a halogen atom, a C.sub.1 -C.sub.40 -hydrocarbon-containing group or an NR.sup.15.sub.2 group, where R.sup.15 is a halogen atom, a C.sub.1 -C.sub.10 -alkyl group or a C.sub.6 -C.sub.10 -aryl group, k is an integer which corresponds to the valence of the transition metal atom M.sup.1 minus two and, if Y is a butadiene unit, k is 1,R.sup.1, R.sup.2, R.sup.3, R.sup.7, R.sup.8 and R.sup.9 are identical or different and are each a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.40 -hydrocarbon-containing group, an --SiR.sup.15.sub.3, --NR.sup.15.sub.2, --SiOR.sup.15.sub.3, --SiSR.sup.15.sub.3 or --PR.sup.15.sub.2 radical, where R.sup.15 is a halogen atom, a C.sub.1 -C.sub.10 -alkyl group or a C.sub.6 -C.sub.
    Type: Grant
    Filed: June 12, 1997
    Date of Patent: May 30, 2000
    Assignee: Targor GmbH
    Inventors: Michael Riedel, Gerhard Erker, Martin Konnemann
  • Patent number: 6057466
    Abstract: Compounds, for initiating the polymerization of ethylenically unsaturated compounds, having the formula ##STR1## where E is nitrogen, phosphorus, arsenic or antimony,X is oxygen, NR.sup.1 or sulphur,L is R.sup.8 R.sup.9 R.sup.10 E.sup.1 (Y).sub.n, alkyl ether, ester, alkyl and aryl nitrites, pyridine, piperidine, sulphoxides, sulphones, sulphimides, sulphodiimides or sulphur ylides, and R.sup.1 -R.sup.5 are as defined in the specification.
    Type: Grant
    Filed: September 29, 1997
    Date of Patent: May 2, 2000
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Heinz Aleksander Ostoja Starzewski, Uwe Denninger
  • Patent number: 6051727
    Abstract: A very effective catalyst system for the polymerization or copolymerization of olefins comprises a cocatalyst, preferably an aluminoxane or a supported aluminoxane, and a metallocene of the formula I ##STR1## in which, in the preferred form, M.sup.1 in Zr or Hf, R.sup.1 and R.sup.2 are halogen or alkyl, R.sup.3 is alkyl, R.sup.4 to R.sup.12 are alkyl or hydrogen and R.sup.13 is a (substituted) alkylene or heteroatom bridge. The metallocenes, in particular the zirconocenes, produce polymers of very high molecular weight, in the case of prochiral monomers polymers of very high molecular weight, very high stereotacticity and very high melting point, at high catalyst activities in the industrially particularly interesting temperature range between 50 and 80.degree. C. In addition, reactor deposits are avoided by means of supported catalyst systems.
    Type: Grant
    Filed: December 31, 1997
    Date of Patent: April 18, 2000
    Assignee: Targor GmbH
    Inventors: Frank Kuber, Bernd Bachmann, Walter Spaleck, Andreas Winter, Jurgen Rohrmann
  • Patent number: 6048993
    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 ##STR1## wherein: M is ruthenium or osmium;X and X.sup.1 are independently any anionic ligand;L and L.sup.1 are any neutral electron donor ligand; and,R and R.sup.1 are each hydrogen or one of the following substituent groups: C.sub.2 -C.sub.20 alkenyl, C.sub.2 -C.sub.20 alkynyl, C.sub.1 -C.sub.20 alkyl, aryl, C.sub.1 -C.sub.20 carboxylate, C.sub.1 -C.sub.20 alkoxy, C.sub.2 -C.sub.20 alkenyloxy, C.sub.2 -C.sub.20 alkynyloxy, aryloxy, C.sub.2 -C.sub.20 alkoxycarbonyl, C.sub.1 -C.sub.20 alkylthio, C.sub.1 -C.sub.20 alkylsulfonyl and C.sub.1 -C.sub.20 alkylsulfinyl. Specific synthetic protocols for vinyl alkylidene catalysts wherein R is hydrogen and R.sup.1 is --CHCR.sup.12 R.sup.13 and non-vinyl alkylidene catalysts are also disclosed.
    Type: Grant
    Filed: February 19, 1999
    Date of Patent: April 11, 2000
    Assignee: California Institute of Technology
    Inventors: Robert H. Grubbs, Tomas R. Belderrain, Seth N. Brown, Thomas E. Wilhelm
  • Patent number: 6043363
    Abstract: Novel aminomethylphosphine ligands have particular substituents on the central carbon atom. Such ligands form coordination complexes that may be catalysts for the polymerization of monomers or other catalytic induced reactions.
    Type: Grant
    Filed: March 8, 1999
    Date of Patent: March 28, 2000
    Assignee: Symyx Technologies, Inc.
    Inventors: Anne Marie LaPointe, Anil Guram, Timothy S. Powers, Bernd Jandeleit, Thomas Boussie, Cheryl Lund
  • Patent number: 6043387
    Abstract: New chiral biphosphines, e.g., ##STR1## are useful as key components in catalysts for asymmetric reactions, providing desirably high enantiomeric excess (ee).
    Type: Grant
    Filed: February 3, 1999
    Date of Patent: March 28, 2000
    Assignee: Merck & Co., Inc.
    Inventors: Philip Pye, Ralph P. Volante, Kai Rossen
  • Patent number: 6043380
    Abstract: This invention is concerned with a ruthenium-iodo-optically active bidentate phosphine complex of the formula (I):[Ru--(I).sub.q --(T.sup.1).sub.n (SOL).sub.r (L)].sub.m (T.sup.2).sub.p (I).sub.s (I)wherein T.sup.1 represents a carboxylic acid anion, SOL represents a polar solvent, L represents an optically active bidentate phosphine ligand, T.sup.2 represents an anion different from halogen atom anions and carboxylic acid anions, n denotes 0 or 1, r denotes 0, 3 or 4, m denotes 1 or 2, q denotes 0 or 1, or where m is 2, q may represent 1 or 1.5, p denotes 0 or 1, and s denotes 0, 1 or 2 is prepared. Said phosphine complex is usefull as an efficient catalyst for asymmetrically hydrogenating 4-methylene-2-oxetanone into optically active 4-methyl-2-oxetanone.
    Type: Grant
    Filed: May 10, 1999
    Date of Patent: March 28, 2000
    Assignee: Takasago International Corporation
    Inventors: Yoshiki Okeda, Tsutomu Hashimoto, Yoji Hori, Toshimitsu Hagiwara
  • Patent number: 6034022
    Abstract: Group 4 metal constrained geometry complexes comprising a fused ring indenyl derivative ligand, catalytic derivatives thereof, processes for preparing the same and their use as components of olefin polymerization catalysts are disclosed.
    Type: Grant
    Filed: June 3, 1999
    Date of Patent: March 7, 2000
    Assignee: The Dow Chemical Company
    Inventors: Mark H. McAdon, Jasson T. Patton, Peter N. Nickias, Ravi B. Shankar, Francis J. Timmers, Brian W. S. Kolthammer, Daniel D. VanderLende, Steven M. Ueligger
  • Patent number: 6034191
    Abstract: An organic aluminoxy compound which shows .sup.27 Al nuclear magnetic resonance spectrum (.sup.27 Al-NMR spectrum) having an A.sub.1 /A.sub.2 ratio of at most 0.1, wherein A.sub.1 is area of a region encompassed by a segment of a line which connects a local minimum point existing between a continuous curve "a" containing a peak appearing at around 150 ppm and a continuous curve "b" containing a peak appearing at around 60 ppm to the point where the above curve "b" comes into contact with the base line and also by the above curve "b" and A.sub.2 is area of a region encompassed by the above curves "a" and "b" and also by the base line; an organic aluminoxy compound containing at least 5%, expressed in terms of aluminum atom, of a portion insoluble in a mixed solvent of toluene and hexane in a ratio by volume of 2:5 at 30.degree. C. or lower; and a catalyst for producing a polymer comprising any of the above organic aluminoxy compounds and a transition metal compound.
    Type: Grant
    Filed: December 21, 1998
    Date of Patent: March 7, 2000
    Assignee: Idemitsu Petrochemical Co., Ltd.
    Inventors: Tsuyoshi Kondoh, Shoji Naganuma, Norio Tomotsu
  • Patent number: 6018064
    Abstract: It is shown metallocences with functionalized bridge of formula ##STR1## wherein M represents a transition metal from groups 3, 4, 5 or 6, L represents cyclopentadienyl-type ligands, Y represents a halogen and which can own one or various bridges between unities L. At least one of these bridges is functionalized through a group constituted by the union between a halogen atom and a silicon, germanium or tin atom. It is also shown a method for the synthesis of these metallocene compounds starting from the corresponding metallic halure and a precursor of the ligand with leaving groups. The functionalization shown by these compounds give them a peculiar reactivity that can be used for the formation of new metallocene derivatives, including bi- or poly-metallocene compounds. This reactivity is shown in the present document through examples with alcohol-type substrates.
    Type: Grant
    Filed: January 30, 1998
    Date of Patent: January 25, 2000
    Assignee: Repsol Quimica S.A.
    Inventors: Luis Mendez Llatas, Antonio Munoz-Escalona Lafuente
  • Patent number: 6013833
    Abstract: The invention relates to a process for the preparation of compounds of the general formula I ##STR1## in which R.sup.1 and R.sup.2 are identical or different and are a C.sub.1 -C.sub.20 -alkyl group, C.sub.3 -C.sub.12 -cycloalkyl group, C.sub.7 -C.sub.12 -aralkyl group or a mono- or binuclear aryl group, in which a ketone of the formula III or IV ##STR2## in which R.sup.1 and R.sup.2 have the above meaning, is asymmetrically hydrogenated.
    Type: Grant
    Filed: March 6, 1998
    Date of Patent: January 11, 2000
    Assignee: Asta Medica Aktiengesellschaft
    Inventors: Rainer Gewald, Gunter Laban
  • Patent number: 6013819
    Abstract: Metal complexes having constrained geometry and a process for preparation thereof, addition polymerization catalysts formed therefrom, processes for preparation of such addition polymerization catalysts, methods of use, and novel polymers formed thereby, including ElPE resins and pseudo-random copolymers, are disclosed and claimed.
    Type: Grant
    Filed: August 26, 1996
    Date of Patent: January 11, 2000
    Assignee: The Dow Chemical Company
    Inventors: James C. Stevens, Robert K. Rosen
  • Patent number: 6008393
    Abstract: Compounds of formulae I: (DIP)IrX.sub.q Y.sub.r (Z), Ia: (DIP)IrX.sub.s Y.sub.t (Z).sub.2 and Ib: (DIP)Ir(Z).sub.3 or mixtures of at least two of those compounds, wherein DIP is a ditertiary diphosphine, the two phosphine groups of which are bonded to a C.sub.2 -, C.sub.3 - or C.sub.4 -carbon chain, with the result that the diphosphine forms a 5- to 7-membered ring together with the Ir atom, X is Cl, Br or I, Y is a hydrogen atom, q and r are 0, 1 or 2 and the sum of q+r is 2, s and t are 0 or 1 and the sum of s+t is 1, and Z is the anion of an organic oxy acid that contains a group C(.dbd.O), S(.dbd.O)O or P(.dbd.O)O in the anion. The compounds are excellent catalysts for the hydrogenation of imines, especially for the enantioselective hydrogenation of prochiral imines.
    Type: Grant
    Filed: January 22, 1998
    Date of Patent: December 28, 1999
    Assignee: Novartis AG
    Inventors: Rafael Sablong, John Anthony Osborn, Felix Spindler
  • Patent number: 5990331
    Abstract: The present invention relates to a metallocene of the formula I, ##STR1## for preparing polyolefins, where M.sup.1 is preferably Zr, Hf or Ti, R.sup.1 and R.sup.2 are each a hydrogen atom, a C.sub.1 -C.sub.3 -alkyl group, a C.sub.1 -C.sub.3 -alkoxy group, a C.sub.6 -C.sub.8 -aryl group, a C.sub.6 -C.sub.8 -aryloxy group, a C.sub.2 -C.sub.4 -alkenyl group, a C.sub.7 -C.sub.10 -arylalkyl group, a C.sub.7 -C.sub.12 -alkylaryl group, a C.sub.8 -C.sub.12 -arylalkenyl group or chlorine, R.sup.3 is a chlorine atom, a C.sub.1 -C.sub.3 -alkyl group, a C.sub.2 -C.sub.4 -alkenyl group, a C.sub.6 -C.sub.8 -aryl group, an NR.sup.16.sub.2, SR.sup.16, OSiR.sup.16.sub.3, SiR.sup.16.sub.3 or PR.sup.16.sub.2 radical where R.sup.16 is chlorine, a C.sub.1 -C.sub.4 -alkyl group or a C.sub.6 -C.sub.8 -aryl group. R.sup.4 is a hydrogen atom, R.sup.13 is --(R.sup.14 M.sup.2 R.sup.15)--, --(R.sup.14 CR.sup.15)--(R.sup.14 CR.sup.15)--, --(R.sup.14 CR.sup.15)--(R.sup.14 M.sup.2 R.sup.15)-- or --(R.sup.14 CR.sup.15)--, where R.sup.
    Type: Grant
    Filed: October 31, 1997
    Date of Patent: November 23, 1999
    Assignee: Targor GmbH
    Inventors: Andreas Winter, Roland Zenk, Volker Fraaije, Frank Kuber
  • Patent number: 5977392
    Abstract: Catalyst component for the polymerization of alpha-olefins of general formula (I) ##STR1## wherein: M is a transition metal of groups 3, 4-10, lanthanide or actinide of the periodic table of the elements; A is a ring with delocalized .pi. electrons, L is a neutral Lewis base; m is an integer whose value can be: 0 or 1; E is selected from the group comprising: BR.sup.II, CR.sup.II.sub.2, SiR.sup.II.sub.2, GeR.sup.II.sub.2 ; Hal is selected from the group comprising iodine, bromine or chlorine; R.sup.III has the same meaning of R.sup.II ; Si is a silicon atom; D is selected from the group comprising: O, S, NR.sup.IV, PR.sup.IV, OR.sup.IV, SR.sup.IV, NR.sup.IV.sub.2, PR.sup.IV.sub.2 ; each X group equal to or different from each other is selected from the group comprising hydrogen, halide, alkyl, cycloalkyl, aryl, alkenyl, arylallyl, arylalkenyl or alkylaryl with 1 to 20 carbon atoms, n is a number whose value can be: 0, 1, 2 or 3, in order to full the remaining valences of metal M.
    Type: Grant
    Filed: October 30, 1997
    Date of Patent: November 2, 1999
    Assignee: Respol Quimica S.A.
    Inventors: Jose Sancho Royo, Antonio Munoz-Escalona Lafuente, Begona Pena Garcia, Carlos Martin Marcos
  • Patent number: 5977393
    Abstract: The present invention generally relates to ruthenium and osmium carbene catalysts for use in olefin metathesis reactions. More particularly, the present invention relates to Schiff base derivatives of ruthenium and osmium carbene catalysts and methods for making the same. The inventive catalysts are generally prepared by the treatment of unmodified catalysts with the salts of the desired Schiff base ligands, in which an anionic and a neutral electron donating ligands of the unmodified catalysts are simultaneously replaced. The Schiff base derivatives of the ruthenium and osmium carbene catalysts show unexpectedly improved thermal stability while maintaining high metathesis activity, even in polar protic solvents. Although the inventive catalysts may be used in all metathesis reactions, use of these catalysts for ring-closing metathesis ("RCM") reactions is particularly preferred.
    Type: Grant
    Filed: November 12, 1998
    Date of Patent: November 2, 1999
    Assignee: California Institute of Technology
    Inventors: Robert H. Grubbs, Sukbok Chang, LeRoy Jones, II, Chunming Wang
  • Patent number: 5969170
    Abstract: Disclosed are ruthenium and osmium carbene compounds which are stable in the presence of a variety of functional groups and which can be used to catalyze olefin metathesis reactions on strained and unstrained cyclic and acyclic olefins. Specifically, the present invention relates to carbene compounds of the formula ##STR1## wherein: M is Os or Ru; R and R.sup.1 are independently selected from hydrogen and substituent groups C.sub.2 -C.sub.20 alkenyl, C.sub.2 -C.sub.20 alkynyl, C.sub.1 -C.sub.20 alkyl, aryl, C.sub.1 -C.sub.20 carboxylate, C.sub.2 -C.sub.20 alkoxy, C.sub.2 -C.sub.20 alkenyloxy, C.sub.2 -C.sub.20 alkynyloxy, aryloxy, C.sub.2 -C.sub.20 alkoxycarbonyl, C.sub.1 -C.sub.20 alkylthio, C.sub.1 -C.sub.20 alkylsulfonyl or C.sub.1 -C.sub.20 alkylsulfinyl; each substituent group optionally substituted with C.sub.1 -C.sub.5 alkyl, a halogen, C.sub.1 -C.sub.5 alkoxy or with a phenyl group optionally substituted with a halogen, C.sub.1 -C.sub.5 alkyl or C.sub.1 -C.sub.5 alkoxy; X and X.sup.
    Type: Grant
    Filed: May 23, 1997
    Date of Patent: October 19, 1999
    Assignee: California Institute of Technology
    Inventors: Robert H. Grubbs, SonBinh T. Nguyen, Lynda K. Johnson
  • Patent number: RE37208
    Abstract: The novel metallocenes of the formula I in which, preferably, M1 is Zr or Hf, R1 and R2 are alkyl or halogen, R3 and R4 are hydrogen, R5 and R6 are alkyl or haloalkyl, —(CR8R9)m—R7—(CR8R9)n— is a single- or multi-membered chain in which R7 may also be a (substituted) hetero atom, m+n is zero or 1, and R10 is hydrogen, form, together with aluminoxanes as cocatalysts, a very effective catalyst system for the preparation of polyolefins or high stereospecificity and high melting point. Polyolefins with unique or improved properties are obtained by polymerizing an olefin in the presence of a metallocene combined with a cocatalyst, wherein the metallocene is preferably a zirconocene or a hafnocene, and the Zr or Hf central atom is coordinated with two ligands which are derivatives of 2-substituted indenyl nuclei and which are substituted with at least one and up to four groups (e.g. aliphatic or aromatic groups) on the six-member rings of the indenyl nuclei.
    Type: Grant
    Filed: October 17, 1994
    Date of Patent: June 5, 2001
    Assignee: Targor GmbH
    Inventors: Andreas Winter, Martin Antberg, Walter Spaleck, Jürgen Rohrmann, Volker Dolle
  • Patent number: RE37384
    Abstract: The novel metallocenes of the formula I in which, preferably, M1 is Zr or Hf, R1 and R2 are alkyl or halogen, R3 and R4 are hydrogen, R5 and R6 are alkyl or haloalkyl, —(CR8R9)m—R7—(CR8R9)n— is a single- or multi-membered chain in which R7 may also be a (substituted) hetero atom, and m+n is zero or 1, form, together with aluminoxanes as cocatalysts, a very effective catalyst system for the preparation of polyolefins of high molecular weight.
    Type: Grant
    Filed: July 13, 1999
    Date of Patent: September 18, 2001
    Assignee: Targor GmbH
    Inventors: Andreas Winter, Martin Antberg, Walter Spaleck, Jürgen Rohrmann, Volker Dolle