Hydrogen Or Halogen Bonded Directly To The Heavy Metal Patents (Class 556/23)
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Patent number: 6794525Abstract: An (R) or (S) chiral diphosphine of formula (I): wherein R and R1, which can be identical or different, represent an optionally saturated C1-10 alkyl group, an optionally saturated C3-9 cycloalkyl group, a C5-10 aryl group, the groups being optionally substituted by a halogen, a hydroxy, a C1-5 alkoxy, an amino, a sulfino, a sulonfyl, with R4 representing an alkyl, an alkoxy or an alkylcarbonyl, the alkyl, cycloalkyl, aryl groups optionally including one or more heteroatoms, or R and R1 together represent an optionally saturated C2-6 substituted alkyl group, an optionally saturated C3-9 cycloalkyl group, a C5-10 aryl group, the cycloalkyl or aryl groups being optionally substituted by a C1-5 alkyl, a halogen, a hydroxy, a C1-5 alkoxy, an amino, a sulfino, a sulonfyl, with R4 representing an alkyl, an alkoxy or an alkylcarbonyl, the alkyl, cycloalkyl, aryl groups optionally including one or more heteroatoms, R2 and R3, which can be identical or different, represent an optionally saturated C3-Type: GrantFiled: January 31, 2003Date of Patent: September 21, 2004Assignee: PPG-SIPSYInventors: Michel Bulliard, Blandine Laboue, Sonia Roussiasse
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Patent number: 6774254Abstract: Novel phosphino-gold (I) compounds, a process for their preparation, pharmaceutical compositions containing such phosphino-gold (I) compounds and their use in the treatment of cancer disease are disclosed.Type: GrantFiled: September 26, 2002Date of Patent: August 10, 2004Assignee: National University of SingaporeInventors: Pak Hing Leung, Soh Ha Chan, Yongcheng Song
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Patent number: 6716787Abstract: 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: GrantFiled: December 18, 2001Date of Patent: April 6, 2004Assignees: 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
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Patent number: 6683198Abstract: 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: GrantFiled: February 21, 2002Date of Patent: January 27, 2004Assignee: Isis Innovation LimitedInventors: Anthony John Downs, Hans-Jörg Himmel
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Patent number: 6613923Abstract: The present invention is a process for the catalytic hydrogenation of ketones and aldehydes to alcohols at low temperatures and pressures using organometallic molybdenum and tungsten complexes and the catalyst used in the process. The reactants include a functional group which is selected from groups represented by the formulas R*(C═O)R′ and R*(C═O)H, wherein R* and R′ are selected from hydrogen or any alkyl or aryl group. The process includes reacting the organic compound in the presence of hydrogen and a catalyst to form a reaction mixture. The catalyst is prepared by reacting Ph3C+A− with a metal hydride. A− represents an anion and can be BF4−, PF6−, CF3SO3− or Bar′4−, wherein Ar′=3,5-bis(trifluoromethyl)phenyl.Type: GrantFiled: April 19, 2000Date of Patent: September 2, 2003Assignee: Brookhaven Science Associates, LLCInventors: R. Morris Bullock, Barbara F. M. Kimmich, Paul J. Fagan, Elisabeth Hauptman
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Patent number: 6613921Abstract: Compounds and metal complexes comprising a polycyclic, fused ring ligand or inertly substituted derivative thereof having up to 60 atoms other than hydrogen, said ligand comprising at least: (1) a cyclopentadienyl ring, (2) a 6, 7, or 8 membered ring other than a 6-carbon aromatic ring, and (3) an aromatic ring, with the proviso that said 6, 7, or 8 membered ring (2), is fused to both the cyclopentadienyl ring (1), and the aromatic ring (3), polymerization catalysts, a process to prepare the novel compounds and complexes, and olefin polymerization processes using the same are disclosed.Type: GrantFiled: June 12, 2001Date of Patent: September 2, 2003Assignee: Dow Global Technologies Inc.Inventors: Richard E. Campbell, Jr., Jerzy Klosin, Ravi B. Shankar, Francis J. Timmers, Robert K. Rosen
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Patent number: 6613910Abstract: 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: GrantFiled: April 2, 2002Date of Patent: September 2, 2003Assignee: California Institute of TechnologyInventors: Robert H. Grubbs, John P. Morgan, Diego Benitez, Janis Louie
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Publication number: 20030148877Abstract: A class of metallocenes of formula (I): (ZR1m)n(Cp)(A)rMLpL′q (I) wherein ZR1m) is a divalent group bridging Cp and A, Cp is a heterocyclic cyclopentadienyl group of formula (II) or (II′), wherein one of X or Y is a single bond, the other being an heteroatom; R2 and R3 are hydrogen, halogen or a hydrocarbon radical, optionally containing heteroatoms; R4 is a halogen or an hydrocarbon radical, optionally containing heteroatoms; the group A is a cyclopentadienyl derivative or is equal to Cp; M is Ti, Zr or Hf; m is 1 or 2; n ranges from 0 to 4; r is 0 or 1; p and q range from 0 to 3; and a ranges from 0 to 4. Moreover, are disclosed catalyst systems containing these metallocenes, useful in the polymerization of olefins.Type: ApplicationFiled: May 2, 2002Publication date: August 7, 2003Inventors: Ilya E. Nifant'ev, Vladimir V. Bagrov
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Patent number: 6596887Abstract: 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: GrantFiled: March 14, 2001Date of Patent: July 22, 2003Assignee: Takasago International CorporationInventors: Koichi Mikami, Toshinobu Korenaga, Noboru Sayo
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Patent number: 6559326Abstract: 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: GrantFiled: November 15, 2000Date of Patent: May 6, 2003Assignee: BASF AktiengesellschaftInventors: Marc Oliver Kristen, Joachim Heinicke, Wilhelm Keim, Martin Koehler, Mengzhen He
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Patent number: 6544918Abstract: A catalyst system useful for polymerizing olefins is disclosed. The catalyst system comprises an activator and a complex that incorporates a Group 3 to 10 transition metal and at least one chelating dianionic bis(allyl) or bis(benzyl) ligand. The ligands are often easy to make, and they are readily incorporated into transition metal complexes. By modifying the structure of the dianionic ligand, polyolefin makers can control comonomer incorporation, catalyst activity, and polymer properties.Type: GrantFiled: July 17, 2001Date of Patent: April 8, 2003Assignee: Equistar Chemicals, LPInventors: Sandor Nagy, Karen L. Neal-Hawkins, Jonathan L. Schuchardt
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Patent number: 6515157Abstract: 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: GrantFiled: June 6, 2001Date of Patent: February 4, 2003Inventors: Hong-Sun Uh, Jeong-Ho Song, Myung-Jin Lee
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Patent number: 6515156Abstract: 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: GrantFiled: June 7, 2001Date of Patent: February 4, 2003Assignee: Takasago International CorporationInventors: Sumi Kenzo, Noyori Ryoji, Ikariya Takao
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Patent number: 6508753Abstract: A novel phosphine ligand is an enantiomerically enriched compound of formula 5 or the opposite enantiomer thereof, wherein Ar1 and Ar2 represent the same or different aromatic groups of up to 20 C atoms. A transition metal complex of this ligand is useful as a catalyst in stereoselective hydrogenation.Type: GrantFiled: June 4, 2001Date of Patent: January 21, 2003Assignee: Chirotech Technology LimitedInventors: Mark Joseph Burk, Christophe Guillaume Malan
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Patent number: 6504041Abstract: 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: GrantFiled: September 28, 2001Date of Patent: January 7, 2003Assignee: California Institute of TechnologyInventors: Robert H. Grubbs, Tomas R. Belderrain, Seth N. Brown, Thomas E. Wilhelm
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Patent number: 6500975Abstract: Cationic ruthenium complexes of the formula A or B or mixtures containing them, where B may be stabilized by a further ligand L4 and X is an anion which does not coordinate or coordinates weakly to the metal center, Y is a monodentate or multidentate anionic ligand, R and R′ are each, independently of one another, hydrogen or a substituted or unsubstituted C1-C20-alkyl, C6-C20-aryl or C7-C20-alkylaryl radical and L1, L2, L3 and L4 are, independently of one another, uncharged electron donor ligands, are described.Type: GrantFiled: November 2, 2000Date of Patent: December 31, 2002Assignee: BASF AktiengesellschaftInventors: Peter Schwab, Michael Schulz, Justin Wolf, Wolfram Stuer, Helmut Werner
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Patent number: 6486337Abstract: The present invention concerns novel complexes, suitable in particular for use as catalysts in the asymmetric hydrogenation of ketones, of formula 1 or a diastereoisomer thereof, wherein each Ar is an aromatic or heteroaromatic group of up to 20 atoms; X is halide or carboxylate; and R1, R2, R3, and R4 are independently hydrogen, aryl or alkyl, optionally linked or part of a ring.Type: GrantFiled: March 29, 2001Date of Patent: November 26, 2002Assignee: Chirotech Technology LimitedInventors: Mark Joseph Burk, William Hems, Antonio Zanotti-Gerosa
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Patent number: 6469169Abstract: The invention provides a water soluble palladium complex of the general formula I wherein R1, R2, R3 are substituents on phosphine ligands selected from the group consisting of hydrogen, alkyl, arylalkyl, and cycloaliphatic at least one of which carries a sulfonic acid, and salts thereof, X is aryl or alkyl sulphonato or aryl or alkyl carboxylato or formato or halides such as Cl−, Br−, I− is an anionic chelating ligand consisting of an N donor and a O− group, 1<n<10 and a process for the preparation thereof.Type: GrantFiled: March 20, 2001Date of Patent: October 22, 2002Assignee: Council of Scientific and Industrial ResearchInventors: Jayasree Seayad, Abdul Majeed Seayad, Bibhas Ranjan Sarkar, Raghunath Vitthal Chaudhari
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Patent number: 6451724Abstract: A class of metallocenes of formula (I): (ZR1m)n(Cp)(A)rMLpL′q(I) wherein (ZR1m)n, is a divalent group bridging Cp and A, Cp is a heterocyclic cyclopentadienyl group of formula (II) or (II′), wherein one of X or Y is a single bond, the other being an heteroatom; R2 and R3 are hydrogen, halogen or a hydrocarbon radical, optionally containing heteroatoms; R4 is halogen or an hydrocarbon radical, optionally containing heteroatoms; the group A is a cyclopentadienyl derivative or is equal to Cp; M is Ti, Zr or Hf; m is 1 or 2; n ranges from 0 to 4; r is 0 or 1; p and q range from 0 to 3; and a ranges from 0 to 4. Moreover, are disclosed catalyst systems containing these metallocenes, useful in the polymerization of olefins.Type: GrantFiled: July 8, 1999Date of Patent: September 17, 2002Assignee: Basell Technology Company BVInventors: Ilya E. Nifant'ev, Vladimir V. Bagrov
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Patent number: 6403772Abstract: New metallocene compounds are described where the ligand contains at least one open-pentadienyl containing radical characterized by a cyclic or acyclic, six &pgr; electron, delocalized, five atomic center structure. These metallocenes can advantageously be used in catalyst systems for the polymerization of olefins to generate a wide variety of different polymers including HDPE, LLDPE, ethylenelpropylene/(diene) elastomers, tactiospecific C3+&agr;-olefin polymers, intimate mixture thereof and the like.Type: GrantFiled: March 6, 1998Date of Patent: June 11, 2002Assignee: Montell Technology Company, BVInventors: John A. Ewen, Robert W. Strozier, Robert L. Jones, Jr., Michael J. Elder
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Patent number: 6380412Abstract: 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: GrantFiled: February 4, 2000Date of Patent: April 30, 2002Assignee: Rhone-Poulenc ChimieInventors: Francois Mathey, Frédéric Robin, Francois Mercier, Michel Spagnol
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Patent number: 6359165Abstract: 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: GrantFiled: September 29, 1999Date of Patent: March 19, 2002Assignee: BASF AktienegesellschaftInventors: Rainer Stürmer, Martin Jochen Klatt, Armin Börmer, Jens Holz, Gudrun Voss
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Patent number: 6323353Abstract: 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: GrantFiled: December 23, 1999Date of Patent: November 27, 2001Assignee: Takasago International CorporationInventors: Kenzo Sumi, Ryoji Noyori, Takao Ikariya
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Patent number: 6313332Abstract: 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: GrantFiled: September 28, 2000Date of Patent: November 6, 2001Assignee: California Institute of TechnologyInventors: Robert H. Grubbs, Tomas R. Belderrain, Seth N. Brown, Thomas E. Wilhelm
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Patent number: 6232483Abstract: 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: GrantFiled: November 18, 1999Date of Patent: May 15, 2001Assignee: E. I. du Pont Nemours and CompanyInventors: Jordan Lawrence Bennett, Maurice S. Brookhart, III, Lynda Kaye Johnson, Christopher Moore Killian
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Patent number: 6225488Abstract: Penta-coordinated ruthenium or osmium catalysts for metathesis reactions of olefins, which are cationic complexes represented by formulas I, II or III: wherein M is ruthenium or osmium; 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 central metal atom M, or X1 and X2 together form a group, optionally substituted, which results from dimerization of an alkene and has at each end an allyl moiety bonded to the central metal atom M, L1 is a neutral electron donor ligand; L2 is a carbene group; L3 is a neutral electron donor ligand which may be the same as or different from L1, or L3 is a halide group; L11 is a neutral electron donor ligand; L12 is a solvent molecule capable of coordination to the central metal atom M; L13 is an alkyl group; L14 is an alkyl, a carbene, a solvent molecule capable of coordination to the central metal atom M, or a halide; L{circumflex over ( )}L is a bidType: GrantFiled: April 2, 1999Date of Patent: May 1, 2001Assignee: Nippon Zeon Co., Ltd.Inventors: Shakti L. Mukerjee, Vernon L. Kyllingstad
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Patent number: 6218559Abstract: 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: GrantFiled: March 11, 1999Date of Patent: April 17, 2001Assignee: Novaritis CorporationInventors: Felix Spindler, Ulrich Pittelkow
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Patent number: 6171994Abstract: A novel multiply crosslinked transition metal compound represented by the formula (I): wherein M is a metallic element of the Groups 3 to 10 or the lanthanide series of the Periodic Table; E1 and E2 are each a &sgr;-bonding or &pgr;-bonding ligand; X is a &sgr;-bonding ligand; Y is a Lewis base; A1, A2, . . . An and D are each a crosslinking group, and at least one of A1, A2, . . . An comprises a crosslink consisting of carbon alone; n is 2 to 4; p is 1 to 4; q is 1 to 5 and equal to the valence of M minus 2; r is 0 to 3; and s is 0 to 4, and a production process thereof. The transition metal compound is useful as a component of a polymerization catalyst for catalyzing the production of an olefin polymer having a uniform composition and a narrow molecular weight distribution in a high yield.Type: GrantFiled: November 2, 1998Date of Patent: January 9, 2001Assignee: Idemitsu Kosan Co., Ltd.Inventors: Nobuhiro Yabunouchi, Kiyohiko Yokota, Masami Watanabe, Takuji Okamoto, Noriyuki Tani
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Patent number: 6153778Abstract: 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: GrantFiled: March 10, 2000Date of Patent: November 28, 2000Assignee: California Institute of TechnologyInventors: Robert H. Grubbs, Tomas R. Belderrain, Seth N. Brown, Thomas E. Wilhelm
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Patent number: 6133478Abstract: A platinum complex useful as a catalyst for converting nitrites into amides comprises a platinum complex of dialkyl phosphine of stoichiometric formula: PtX(R.sub.2 POHOPR.sub.2)(PR.sub.2 OH) where R is an alkyl, alicyclic, chiral, alkylaryl group or substituted alkyl, alicyclic, chiral, alkaryl group or the two R groups attached to one phosphorous atom can form a heterocyclic ring with the phosphorous atom and X is H or a halide. The conversion takes place under reflux conditions to give a high yield of the amide.Type: GrantFiled: June 7, 1999Date of Patent: October 17, 2000Inventors: Adrian W Parkins, Talit Ghaffar
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Patent number: 6127563Abstract: 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: GrantFiled: October 20, 1999Date of Patent: October 3, 2000Assignee: The Dow Chemical CompanyInventors: Eugene Y. Chen, David D. Devore, Richard E. Campbell, Jr., D. Patrick Green, Jasson T. Patton, Jorge Soto, David R. Wilson
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Patent number: 6096912Abstract: Abstract of the Disclosure: Catalyst systems for the polymerization of C.sub.2 -C.sub.10 -alk-1-enes contain, as active components,a) a metallocene complex of the general formula I ##STR1## where M is titanium, zirconium, hafnium, vanadium, niobium or tantalum, X is halogen or C.sub.1 -C.sub.8 -alkyl, Y is carbon, phosphorus, sulfur, silicon or germanium, Z is C.sub.1 -C.sub.8 -alkyl, C.sub.3 -C.sub.10 -cycloalkyl or C.sub.6 -C.sub.10 -aryl, R.sup.1 and R.sup.2 are identical or different and are each C.sub.1 -C.sub.4 -alkyl, R.sup.3 to R.sup.6 are identical or different and are each hydrogen or C.sub.1 -C.sub.8 -alkyl, or two adjacent radicals R.sup.3 and R.sup.4 and R.sup.5 and R.sup.6 in each case together form a hydrocarbon ring system of 4 to 15 carbon atoms and n is 0, 1 or 2, andb) an open-chain or cyclic alumoxane compound of the general formula II or III ##STR2## where R.sup.7 is C.sub.1 -C.sub.4 -alkyl and n is from 5 to 30.Type: GrantFiled: May 3, 1996Date of Patent: August 1, 2000Assignee: BASF AktiengesellschaftInventors: Eberhard Karl, Werner Roell, Hans Brintzinger, Bernhard Rieger, Udo Stehling
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Patent number: 6090739Abstract: 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: GrantFiled: June 18, 1997Date of Patent: July 18, 2000Assignee: Targor GmbHInventors: Michael Riedel, Gerhard Erker, Lothar Duda
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Patent number: 6084114Abstract: 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: GrantFiled: July 19, 1999Date of Patent: July 4, 2000Assignee: Aventis Research & Technologies GmbH & Co. KGInventors: Holger Geissler, Peter Gross, Bianca Guckes
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Patent number: 6084033Abstract: The present invention relates to a new bimetallic complex catalyst system having the empirical formula of M.sup.1.sub.a M.sup.2.sub.b X.sub.m (L.sub.1).sub.n, wherein M.sup.1 is Rh or Ru, M.sup.2 is Ru or a lanthanide, when M.sup.1 is Rh, M.sup.2 is Ru or a lanthanide; when M.sup.1 is Ru, M.sup.2 is a lanthanide; X is H, Cl, Br or the combinations thereof; L.sub.1 is the ligand to the metal salt; 1.ltoreq.a.ltoreq.4; 1.ltoreq.b.ltoreq.2; 3.ltoreq.m.ltoreq.6; 6.ltoreq.n.ltoreq.15. The present invention also relates to a corresponding improved process for the hydrogenation of unsaturated copolymers, particularly NBR type rubber, wherein the above mentioned new bimetallic complex catalyst system is used.Type: GrantFiled: May 8, 1998Date of Patent: July 4, 2000Assignee: Nantex Industry Co., Ltd.Inventors: Kuei-Hsien Hsu, Guanying Wu, Ruiqing Xu, Dongmei Yue, Shuqin Zhou
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Patent number: 6069264Abstract: 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: GrantFiled: June 12, 1997Date of Patent: May 30, 2000Assignee: Targor GmbHInventors: Michael Riedel, Gerhard Erker, Martin Konnemann
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Patent number: 6069253Abstract: The present invention relates to novel group VIII transition metal complexes represented by the formula (I) as: ##STR1## wherein M is the central transition metal; represents a semilabile anionic chelating ligand; R.sub.1, R.sub.2 & R.sub.3 are substituents on the phosphine ligand, X is chosen from sulphonato, carboxylato, formato group or halides and 1<n<10. The invention also provides a process for the preparation of said transition metal complex.Type: GrantFiled: March 31, 1999Date of Patent: May 30, 2000Assignee: Council of Scientific and Industrial ResearchInventors: Raghunath V. Chaudhari, Jayasree Seayad, Seayad A. Majeed
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Patent number: 6069237Abstract: New metallocene ligand systems and catalysts/catalyst precursors are described where the ligand system contains at least one open-pentadienyl ligand characterized by an acyclic six .pi. electron delocalized, five atomic center structure. The open pentadienyl ligand is bonded to either another pentadienyl ligand or a Cp ligand by a bridging group. The metal is from group 3-5 or the Lanthanides. These metallocene catalysts/catalyst precursors optionally in combination with co-catalysts can be used to generate a wide variety of different polymer types including HDPE, LLDPE, LHDPE, ethylene/propylene elastomers, tactiospecific C3+ .alpha.-olefins, intimate mixture thereof and the like.Type: GrantFiled: September 11, 1995Date of Patent: May 30, 2000Assignee: Montell Technology Company BVInventors: John A. Ewen, Robert W. Strozier
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Patent number: 6057466Abstract: 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: GrantFiled: September 29, 1997Date of Patent: May 2, 2000Assignee: Bayer AktiengesellschaftInventors: Karl-Heinz Aleksander Ostoja Starzewski, Uwe Denninger
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Patent number: 6051727Abstract: 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: GrantFiled: December 31, 1997Date of Patent: April 18, 2000Assignee: Targor GmbHInventors: Frank Kuber, Bernd Bachmann, Walter Spaleck, Andreas Winter, Jurgen Rohrmann
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Patent number: 6048993Abstract: 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: GrantFiled: February 19, 1999Date of Patent: April 11, 2000Assignee: California Institute of TechnologyInventors: Robert H. Grubbs, Tomas R. Belderrain, Seth N. Brown, Thomas E. Wilhelm
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Patent number: 6013833Abstract: 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: GrantFiled: March 6, 1998Date of Patent: January 11, 2000Assignee: Asta Medica AktiengesellschaftInventors: Rainer Gewald, Gunter Laban
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Patent number: 5981771Abstract: 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: GrantFiled: June 22, 1998Date of Patent: November 9, 1999Assignee: Takasago International CorporationInventors: Yoshiki Okeda, Yoji Hori, Toshimitsu Hagiwara
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Patent number: 5981782Abstract: 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: GrantFiled: November 4, 1997Date of Patent: November 9, 1999Assignee: Takasago International CorporationInventors: Yoshiki Okeda, Yoji Hori, Toshimitsu Hagiwara
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Patent number: 5932756Abstract: A platinum complex useful as a catalyst for converting nitriles into amides comprises a platinum complex of dialkyl phosphine of stoichiometric formula: PtX(R.sub.2 POHOPR.sub.2)(PR.sub.2 OH) were R is an alkyl, alicyclic, chiral, alkylaryl group or substituted alkyl, alicyclic, chiral, alkaryl group or the two R groups attached to one phosphorus atom can form a heterocyclic ring with the phosphorus atom and X is H or a halide. The conversion takes place under reflux conditions to give a high yield of the amide.Type: GrantFiled: September 10, 1997Date of Patent: August 3, 1999Inventors: Adrian W Parkins, Talit Ghaffar
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Patent number: 5922634Abstract: A water-soluble catalyst composition comprising rhodium complexes containing diphosphine ligands, wherein the diphosphine ligands present are compounds of the formula ##STR1## where R.sup.1 is selected from the group consisting of carboxylate (COO.sup.-), sulfonate (SO.sub.3.sup.-), phosphonate (PO.sub.3.sup.2-) and 2-amino ethanebisphosphonate ?NH--CH.sub.2 --CH(PO.sub.3.sup.2-).sub.2 !, R.sup.2 is selected from the group consisting of a straight-chain alkylene of 1 to 8 carbon atoms, an oxygen-containing alkylene of 2 to 6 carbon atoms, cycloalkylene of 3 to 10 carbon atoms and a member of the formulae II, III, IV or V ##STR2## a, b, c, d, e, f, g, h, k and l are individually 0 to 1, where at least one of a, b, c, d, e, f, g, h, k or l has to be equal to 1, x(s) are individually 0 or 1, y is an integer of 1 to 24, R.sup.3 and R.sup.Type: GrantFiled: April 17, 1997Date of Patent: July 13, 1999Assignee: Hoechst AktiengesellschaftInventors: Helmut Bahrmann, Peter Lappe, Thomas Muller
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Patent number: 5919962Abstract: Disclosed is a ruthenium-phosphine complex represented by formula (I):?{RuX(L)}.sub.2 (.mu.-X).sub.3 !.sup.- ?R.sub.2 NH.sub.2 !.sup.+(I)wherein R is hydrogen, an alkyl group having 1 to 5 carbon atoms, a cycloalkyl group, a substituted or unsubstituted phenyl group or a substituted or unsubstituted benzyl group; X is halogen; and L is an optically active or inactive tertiary phosphine. A process for preparing the complex (I) is also disclosed, which comprises (A) reacting a ruthenium complex represented by formula: ?RuX(arene)(L)!X (wherein arene is a substituted or unsubstituted phenyl group) and an ammonium salt represented by formula (III): R.sub.2 NH.HX, or (B) reacting a ruthenium complex represented by formula: ?RuX.sub.2 (arene)!.sub.2, a tertiary phosphine represented by L, and an ammonium salt (III). The complex (I) useful as a catalyst for general syntheses or asymmetric syntheses can be obtained easily in good yield.Type: GrantFiled: September 19, 1997Date of Patent: July 6, 1999Assignee: Takasago International CorporationInventors: Noboru Sayo, Kazushi Mashima, Kyoko Tamao, Tetsuo Ota
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Patent number: 5917071Abstract: The present invention relates to the synthesis of highly active ruthenium and osmium vinyl alkylidene catalysts. In one embodiment, the invention may be summarized by the following reaction scheme ##STR1## wherein n is 1 or 2;X and X.sup.1 are each anionic ligands;L and L.sup.1 are each neutral electron donors andR.sup.17 which is hydrogen, aryl or C.sub.1 -C.sub.18 alkyl; and,R.sup.12 and R.sup.13 are each hydrogen or one of the following substituent groups: C.sub.1 -C.sub.18 alkyl, C.sub.2 -C.sub.18 alkenyl, C.sub.2 -C.sub.18 alkynyl, aryl, C.sub.1 -C.sub.18 carboxylate, C.sub.1 -C.sub.18 alkoxy, C.sub.2 -C.sub.18 alkenyloxy, C.sub.2 -C.sub.18 alkynyloxy, aryloxy, C.sub.2 -C.sub.18 alkoxycarbonyl, C.sub.1 -C.sub.18 alkylthio, C.sub.1 -C.sub.18 alkylsulfonyl and C.sub.1 -C.sub.18 alkylsulfinyl.Type: GrantFiled: November 7, 1997Date of Patent: June 29, 1999Assignee: California Institute of TechnologyInventors: Robert H. Grubbs, Tomas R. Belderrain, Seth N. Brown, Thomas E. Wilhelm
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Patent number: 5912376Abstract: A process for the preparation of a metal carbene, in which a metal salt is first reacted in the presence of a base and a secondary or tertiary alcohol with a tertiary phosphine or phosphite or a ditertiary diphosphine or diphosphite and then reacted in the presence of an acid with an alkyne and, if desired, an alkene.Type: GrantFiled: October 27, 1997Date of Patent: June 15, 1999Assignee: Ciba Specialty Chemicals CorporationInventors: Paul Adriaan Van Der Schaaf, Roman Kolly, Andreas Hafner, Andreas Muhlebach
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Patent number: 5912310Abstract: Metallocene complexes of the formula I ##STR1## where M is titanium, zirconium, hafnium, vanadium, niobium or tantalum,n is an integer from 0 to 10,R.sup.5 is ##STR2## R.sup.11 to R.sup.14 are as designated in the disclosure, n.sup.1 is an integer from 0 to 10,X.sup.1 to X.sup.4 are each fluorine, chlorine, bromine, iodine, hydrogen, C.sub.1 -C.sub.10 -alkyl, C.sub.6 -C.sub.15 -aryl, alkylaryl having 1 to 10 carbon atoms in the alkyl radical and 6 to 20 carbon atoms in the aryl radical, --OR.sup.15 --, --NR.sup.15 R.sup.16 or ##STR3## R.sup.15 to R.sup.21 are as designated in the disclosure, and o, p, q, r are each an integer from 0 to 4, the sum o+p+q+r+1 corresponding to the valency of M,which were used as active catalyst components in the preparation of polymers of C.sub.2 -C.sub.10 -alkenes, are recovered by a process wherein the polymerization is stopped by adding an acid and the metallocene complexes of the formula I are recovered by extraction from the reaction mixture.Type: GrantFiled: March 23, 1998Date of Patent: June 15, 1999Assignee: BASF AktiengesellschaftInventors: Marc Oliver Kristen, Peter Jutzi, Thomas Redeker