Exactly Three Carbons Bonded Directly To The Phosphorus (e.g., Triphenylphosphines, Etc.) Patents (Class 556/21)
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Patent number: 5965756Abstract: 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: GrantFiled: October 14, 1997Date of Patent: October 12, 1999Assignee: The Dow Chemical CompanyInventors: Mark H. McAdon, Jasson T. Patton, Peter N. Nickias, Ravi B. Shankar, Francis J. Timmers, Brian W. Kolthammer, Daniel D. VanderLende, Steven M. Ueligger
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Patent number: 5929265Abstract: Binuclear iridium (I) phosphine complexes of the general formula: ##STR1## in which X is fluorine, chlorine, bromine or iodine, and ##STR2## is in each case a chiral bidentate diphosphine ligand. The complexes are particularly suitable as catalysts for the inter- or intramolecular asymmetric hydroamination of prochiral olefins.Type: GrantFiled: October 13, 1998Date of Patent: July 27, 1999Assignee: Lonza AGInventors: Romano Dorta, Patrick Egli, Nikolaus H Bieler, Antonio Togni, Martin Eyer
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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: 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: 5912375Abstract: 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: June 9, 1997Date of Patent: June 15, 1999Assignee: Novartis CorporationInventors: Felix Spindler, Ulrich Pittelkow
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Patent number: 5892081Abstract: The present invention relates to a process for preparing racemic ansa-metallocene complexes I ##STR1## tin compounds II ##STR2## and a process for preparing tin compounds II. R.sup.1 to R.sup.9, M, and X are defined herein.Type: GrantFiled: July 13, 1998Date of Patent: April 6, 1999Assignee: BASF AktiengesellschaftInventors: Carsten Suling, Mario Huettenhofer, Hans-Herbert Brintzinger, Frank Schaper
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Patent number: 5883275Abstract: The present invention relates to a process for the hydrogenation of metallocenes, which comprises treating at least one metallocene containing at least one double bond and/or at least one aromatic substituent in at least one nonhalogenated solvent with hydrogen in the presence of at least one hydrogenation catalyst.Type: GrantFiled: October 31, 1997Date of Patent: March 16, 1999Assignee: Targor GmbHInventors: Carsten Bingel, Erich Hubscher, Claus-Peter Niesert, Roland Zenk
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Patent number: 5883277Abstract: Metallocene complexes having a cationic bridge of the formula ##STR1## where the substituents have the following meanings: M is a metal of transition group III, IV, V or VI of the Periodic Table of the Elements or a metal of the lanthanide group,X is fluorine, chlorine, bromine, iodine, hydrogen, C.sub.1 -C.sub.10 -alkyl, C.sub.6 -C.sub.15 -aryl or --OR.sup.5,R.sup.1 to R.sup.12, Y, Z and n having the meanings set out in the specification, said complexes can be prepared via ligand systems of the formula II ##STR2## as intermediates.Type: GrantFiled: August 14, 1997Date of Patent: March 16, 1999Assignee: BASF AktiengesellschaftInventors: David Fischer, Franz Langhauser, Gunther Schweier, Hans-Herbert Brintzinger, Nadine Leyser
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Patent number: 5880301Abstract: The present invention provides a novel optically active bidentate phosphine ligand palladium complex of formula (I) or (II) which can be used for the preparation of optically active .beta.-hydroxyketones: ##STR1## ?wherein Y.sup.- represents an anion pair which may form salt; X represents ##STR2## {wherein R.sup.1 represents hydrogen atom, C.sub.1-6 alkyl group, C.sub.1-6 alkoxyl group, cyano group, nitro group, halogen atom or phenyl group, etc.; m represents 1 or 2; when m is 2, two R.sup.1 s may be same or different}; andA and B each independently represents phenyl group or cyclohexyl group {said phenyl group and cyclohexyl group each is unsubstituted or substituted by R.sup.2 (R.sup.2 has the same meaning as defined in R.sup.1)}).Type: GrantFiled: September 16, 1997Date of Patent: March 9, 1999Assignee: Nissan Chemical Industries, Ltd.Inventors: Masakatsu Shibasaki, Mikiko Sodeoka, Kazuhiko Ohrai
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Patent number: 5874600Abstract: A catalyst of ruthenium (II) which includes bidentate phosphine ligands. The catalyst is obtainable by a process which includes the steps of treating equimolar amounts of an appropriate Ru(II) complex and a bidentate diphosphine ligand with an acid of formula HX, wherein X is a non-coordinating anion. The acid is used in a ratio which does not exceed 2 molar equivalents per mole of Ru(II) complex and the treatment is carried out in a non-coordinating or weakly coordinating solvent and under an inert atmosphere. This catalyst is useful for the preparation of the preferred isomer of HEDIONE, having the (+)-(1R)-cis-configuration.Type: GrantFiled: July 10, 1997Date of Patent: February 23, 1999Assignee: Firmenich SAInventors: Valentin Rautenstrauch, Koenraad P. M. Vanhessche, Jean-Pierre Genet, Jean-Yves Lenoir
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Patent number: 5872273Abstract: A novel diphosphine compound of the formula (I): ##STR1## where R.sup.1 and R.sup.2 represent independently cycloalkyl, unsubstituted or substituted phenyl, or a five-membered heteroaromatic ring. The compound is useful as a ligand for an asymmetric reaction, in particular, as an asymmetric hydrogenation catalyst.Type: GrantFiled: December 22, 1997Date of Patent: February 16, 1999Assignee: Takasago International CorporationInventors: Takao Saito, Tohru Yokozawa, Xiaoyaong Zhang, Noburo Sayo
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Patent number: 5856540Abstract: The present invention relates to optically active and racemic C.sub.2 -symmetric 2,2'-disubstituted 1,1'-diphosphino-ferrocenes of the formula Ia, to optically active and racemic asymmetric 1',2-disubstituted 1-phosphino-ferrocenes of the formula Ib and to achiral 2,2'-disubstituted 1,1'-diphosphino-ferrocenes of the formula II, to processes for preparing them, especially in accordance with the principle of asymmetric ortho-lithiation, to their use as ligands for transition metal complexes, to transition metal complexes comprising them, and to the use of the transition metal complexes as catalysts, especially in asymmetric syntheses.Type: GrantFiled: April 24, 1997Date of Patent: January 5, 1999Assignee: Hoechst AktiengesellschaftInventor: Joachim-Heiner Jendralla
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Patent number: 5843993Abstract: A complex and method for making same for use as a diagnostic or therapeutic pharmaceutical includes a ligand comprising at least one hydroxyalkyl phosphine donor group bound to a gold atom to form a gold-ligand complex that is stable in aqueous solutions containing oxygen, serum and other body fluids.Type: GrantFiled: March 14, 1997Date of Patent: December 1, 1998Assignee: The Curators of the University of MissouriInventors: Kattesh V. Katti, Douglas E. Berning, Wynn A. Volkert, Alan R. Ketring
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Patent number: 5840950Abstract: In a process for converting the achiral meso form or the racemate of an ansa-metallocene complex or a mixture thereof into one of its enantiomers, the conversion is carried out photochemically in the presence of an enantiomerically pure auxiliary reagent.Type: GrantFiled: January 8, 1998Date of Patent: November 24, 1998Assignee: BASF AktiengesellschaftInventors: David Fischer, Franz Langhauser, Rainer Sturmer, Jurgen Kerth, Gunther Schweier, Hans-Herbert Brintzinger, Katrin Schmidt
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Patent number: 5840949Abstract: Metallocene complexes of the formula I ##STR1## where M is titanium, zirconium, hafnium, vanadium, niobium or tantalum,R.sup.1 and R.sup.4 are as defined in the specificationY is nitrogen, phosphorus, arsenic, antimony or bismuth,Z is oxygen, sulfur, selenium or tellurium,n is an integer from 0 to 10,R.sup.5 is ##STR2## R.sup.11 to R.sup.14 and m are as defined in the specification, and 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## and R.sup.15 to R.sup.21 are as defined in the specification. The complexes are used as catalyst components for polymerizing olefins.Type: GrantFiled: April 25, 1997Date of Patent: November 24, 1998Assignee: BASF AktiengesellschaftInventors: Marc Oliver Kristen, Peter Jutzi, Thomas Redeker
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Patent number: 5834611Abstract: 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: GrantFiled: June 19, 1997Date of Patent: November 10, 1998Assignee: Bayer AktiengesellschaftInventors: Birgit Driessen-Holscher, Wilhelm Keim, Thomas Prinz, Hans-Joachim Traenckner, Jorg-Dietrich Jentsch
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Patent number: 5831107Abstract: A palladacycle of the formula (I) ##STR1## where: R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are, independently of one another, hydrogen, (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-alkoxy, fluorine, NH.sub.2, NH-alkyl(C.sub.1 -C.sub.4), N(alkyl).sub.2 -(C.sub.1 -C.sub.4), CO.sub.2 -(C.sub.1 -C.sub.4)alkyl, OCO-alkyl-(C.sub.1 -C.sub.4), or phenyl,R.sup.7 and R.sup.8 are, independently of one another, (C.sub.1 -C.sub.8)-alkyl, (C.sub.3 -C.sub.12)-cyloalkyl, substituted or unsubstituted arylor where R.sup.1, and R.sup.2, R.sup.2 and R.sup.3, R.sup.3 and R.sup.4, R.sup.5 and R.sup.6 together form an aliphatic or aromatic ring, andY is an anion of an inorganic or organic acid.Type: GrantFiled: December 10, 1996Date of Patent: November 3, 1998Assignee: Aventis Research & Technology DeutschlandInventors: Matthias Beller, Hartmut Fischer, Wolfgang Anton Herrmann, Christoph Brossmer
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Patent number: 5831108Abstract: 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: GrantFiled: July 31, 1996Date of Patent: November 3, 1998Assignee: California Institute of TechnologyInventors: Robert H. Grubbs, Peter Schwab, Sonbinh T. Nguyen
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Patent number: 5831106Abstract: A process for preparing metallocene complexes of the general ##STR1## in which the substituents have the following meanings:M is titanium, zirconium, hafnium, vanadium, niobium or tantalum,X is fluorine, chlorine, bromine, iodine, hydrogen, C.sub.1 -C.sub.10 -alkyl, C.sub.6 -C.sub.15 -aryl or --OR.sup.5,where R.sup.5 is C.sub.1 -C.sub.10 -alkyl, C.sub.6 -C.sub.15 -aryl, alkylaryl, aryl-alkyl, fluoroalkyl or fluoroaryl with, in each case, 1 to 10 carbon atoms in the alkyl radical and 6 to 20 carbon atoms in the aryl radical,R.sup.1 to R.sup.4 and R.sup.6 to R.sup.9 are hydrogen, C.sub.1 -C.sub.10 -alkyl, 5- to 7-membered cycloalkyl which can in turn carry C.sub.1 -C.sub.10 -alkyls as substituents, or C.sub.6 -C.sub.15 -aryl or aryl-alkyl, it also being possible where appropriate for two adjacent radicals together to be cyclic groups having 4 to 15 carbon atoms, or Si(R.sup.10).sub.3 withR.sup.10 being C.sub.1 -C.sub.10 -alkyl, C.sub.6 -C.sub.15 -aryl or C.sub.3 -C.sub.Type: GrantFiled: May 16, 1996Date of Patent: November 3, 1998Assignee: BASF AktiengesellschaftInventors: Franz Langhauser, David Fischer, Gunther Schweier, Hans-Herbert Brintzinger, Hans-Robert-Hellmuth Damrau
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Patent number: 5817848Abstract: The invention relates to a bidentate phosphine ligand, the phosphorus atoms of the phosphine being connected via a bridge group, the bridge group of the bidentate phosphine ligand consisting of an ortho-anellated annular system, comprising two aryl groups, which aryl groups are connected by two bridges, the first bridge consisting of an --O-- or an --S-- atom and the second bridge being a group that contains an oxygen, sulphur, nitrogen, silicon or carbon atom or a combination of these atoms, the two phosphorus atoms being connected to the two aryl groups of the bridge group at the ortho-position relative to the --O-- or --S-- atom of the first bridge.The invention also relates to the use of this bidentate phosphium ligand in a catalyst system comprising also a transition metal compound which is used in the following type of reactions: hydroformylation hydrogenation, hydrocyanation, polymerization, isomerisation, carboxylation, cross coupling and metathesis.Type: GrantFiled: November 6, 1996Date of Patent: October 6, 1998Assignee: DSM N.V.Inventors: Paulus C. J. Kamer, Mirko Kranenburg, Petrus W. N. M. van Leeuwen, Johannes G. de Vries
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Patent number: 5804161Abstract: Compounds of formula (I)?M.sub.6 Q.sub.8 B.sub.n L.sub.6-n !.sup.xwhere M is Re or Rh;each Q is a bridging atom selected from O, S, Se and Te;B is a monovalent non-bridging atom or moiety;L is a PR.sub.3 group in which R is C.sub.1-6 alkyl or aryl, optionally substituted on the alkyl or aryl group by one or more water-solubilizing groups such as an amine or hydroxidy group, or the three R groups together form a C.sub.6-10 trivalent group which may also contain up to three nitrogen or oxygen atoms;n is an integer from 0 to 6;and x is an integer from -2 to +4, representing the overall charge of the cluster, which when non-zero is accompanied by one or more counter ions of equal and balancing charge, and contrast media, particularly X-ray contrast media, containing them.Type: GrantFiled: August 26, 1996Date of Patent: September 8, 1998Assignee: Nycomed Salutar Inc.Inventors: Jeffrey R. Long, Xhiping Xheng, Richard H. Holm, Shi-Bao Yu, Michael Droege, William A. Sanderson
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Patent number: 5801261Abstract: The invention relates to enantiomerically pure bisphosphines of the general formula (I) ##STR1## where R is as defined in the description,a process for their preparation and their use in metal complexes as catalysts for asymmetric reactions, in particular asymmetric hydrogenations.Type: GrantFiled: October 17, 1997Date of Patent: September 1, 1998Assignee: Bayer AktiengesellschaftInventors: Christian Laue, Georg Schroder, Dieter Arlt
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Patent number: 5789609Abstract: Disclosed are an optically active diphosphine represented by formula: ##STR1## wherein R represents a lower alkyl group having 1 to 4 carbon atoms; Ar represents a phenyl group which may be substituted with a lower alkyl group having 1 to 4 carbon atoms and/or a lower alkoxy group having 1 to 4 carbon atoms, a transition metal complex containing the diphosphine as a ligand, and a process for producing an optically active .delta.-oxo-.alpha.-cyano ester using the transition metal complex as a catalyst.Type: GrantFiled: October 22, 1997Date of Patent: August 4, 1998Assignee: Takasago International CorporationInventors: Kyoko Tamao, Koji Inagaki, Noboru Sayo
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Patent number: 5783738Abstract: 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 .alpha.,.beta.-unsaturated carboxylic acids and/or derivatives.Type: GrantFiled: October 4, 1996Date of Patent: July 21, 1998Assignee: Rhone-Poulenc ChimieInventors: Francois Mathey, Frederic Robin, Francois Mercier, Michel Spagnol
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Patent number: 5780701Abstract: An improved process is described for the catalytic dehydrogenation of organic molecules having a ##STR1## group to produce a ##STR2## group. The organic molecules are: ##STR3## wherein: A.sup.1, A.sup.2, A.sup.3, and A.sup.4 are each independently P, As or N: E.sup.2 is independently C or N; E.sup.3 is independently C, Si or Ge; E.sup.4 is independently C, Si, or Ge; and E.sup.5 is independently C, Si or Ge; M.sup.1, M.sup.2, M.sup.3, and M.sup.4 each is a metal atom independently selected from the group consisting of ruthenium, rhodium, palladium, osmium, iridium and platinum; Q.sup.1, Q.sup.2, Q.sup.3, and Q.sup.4 are each independently a direct bond, --CH.sub.2 --, --CH.sub.2 CH.sub.2 --, or CH.dbd.CH--;in structure I, structure II or structure IV, R.sup.1, R.sup.2, R.sup.3, and R.sup.4 are each independently selected from alkyl, alkenyl, cycloalkyl, and aryl, or R.sup.1 and R.sup.2 together and R.sup.3 and R.sup.4 together form a ring structure having from 4 to 10 carbon atoms, orin structure III, R.sup.Type: GrantFiled: July 26, 1996Date of Patent: July 14, 1998Assignees: The Regents of the University of California, University of HawaiiInventors: William C. Kaska, Craig M. Jensen
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Patent number: 5756760Abstract: A 1-substituted-2-diphenylphosphinonaphthalene represented by formula (I): ##STR1## wherein at least one of R.sup.1, R.sup.2, R.sup.3, and R.sup.4, which may be the same or different, represents a lower alkyl group having 1 to 4 carbon atoms which may be substituted with an alkoxy group, a phenyl group or --OR.sup.6 (wherein R.sup.6 represents a hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms or an alcohol-protective group), and the rest of them represent a hydrogen atom; A represents a single bond or a methylene group; and R.sup.5 represents a substituted or unsubstituted phenyl group; and a transition metal complex comprising the 1-substituted-2-diphenylphosphinonaphthalene as a ligand. The transition metal complex is useful as a catalyst in asymmetric synthesis.Type: GrantFiled: March 7, 1997Date of Patent: May 26, 1998Assignee: Takasago International CorporationInventors: Sotaro Miyano, Tetsutaro Hattori, Yasuko Komuro, Hidenori Kumobayashi
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Patent number: 5750752Abstract: The present invention relates to a stereorigid transition metal compound having as ligands a cyclopentadienyl group and a substituted or unsubstituted heteroatom which are connected to one another via a monocyclic or polycyclic ring system, with the cyclopentadienyl group being fused onto the monocyclic or polycyclic ring system. The transition metal compound of the invention is suitable as a catalyst component for olefin polymerization.Type: GrantFiled: June 21, 1996Date of Patent: May 12, 1998Assignee: Hoechst AktiengesellschaftInventors: Michael Riedel, Frank Kuber, Michael Aulbach, Gerhard Erker, Martin Konemann
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Patent number: 5726334Abstract: This invention relates to a process for the preparation of ruthenium complexes of the formula RuH.sub.2 L.sub.2 (PR.sub.3).sub.2, wherein each L is independently H.sub.2 or an additional equivalent of PR.sub.3, and each R is independently H, a hydrocarbyl group, or an assembly of at least two hydrocarbyl groups connected by ether or amine linkages, comprising contacting a source of ruthenium and PR.sub.3 with gaseous hydrogen in the presence of a strong base, a phase-transfer catalyst, water and an organic solvent; and the use of certain classes of ruthenium complexes as catalysts in hydrogenation, and reductive hydrolysis processes.Type: GrantFiled: September 19, 1996Date of Patent: March 10, 1998Assignee: E. I. du Pont de Nemours and CompanyInventors: Richard Paul Beatty, Rocco Angelo Paciello
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Patent number: 5714427Abstract: A catalyst system comprising an aluminoxane and a transition-metal component (metallocene) is used, the transition-metal component comprising at least one zirconocene of the formula I ##STR1## and at least one zirconocene of the formula Ia or alternatively at least 2 zirconocenes of the formula I.Type: GrantFiled: September 23, 1994Date of Patent: February 3, 1998Assignee: Hoechst AktiengesellschaftInventors: Andreas Winter, Volker Dolle, Walter Spaleck
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Patent number: 5710086Abstract: Reaction mixtures prepared from tetraalkyl titanates and mixtures of glycols, said reaction mixtures comprising titanium bisglycoxide oligomers, may be used as depolymerization catalysts for conversion of linear polyesters to macrocyclic polyester oligomers.Type: GrantFiled: March 20, 1996Date of Patent: January 20, 1998Assignee: General Electric CompanyInventors: Daniel Joseph Brunelle, Tohru Takekoshi, Judith Ann Serth-Guzzo
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Patent number: 5698022Abstract: A precursor composition useful for vapor deposition formation of lanthanide metal/phosphorus oxide films, comprising a precursor compound selected from the group consisting of: (i) adducts of the formula MA.sub.3 (L).sub.x ; (ii) phosphido complexes of the formulae M(PR.sub.3).sub.3 or M(PR.sub.3).sub.3 L.sub.x ; and (iii) disubstituted phosphate complexes of the formulae A.sub.2 M(O.sub.2 P(OR).sub.2), AM(O.sub.2 P(OR).sub.2).sub.2, and M(O.sub.2 P(OR).sub.2).sub.3, wherein: x is from 1 to 5, A=Cp or .beta.-diketonate, Cp=cyclopentadienyl, methylcyclopentadienyl, or TMS-cyclopentadienyl, R=C.sub.1 -C.sub.8 alkyl, and L=a phosphorus-containing ligand selected from the group consisting of phosphine, phosphine oxide, phosphite, phosphate, and 1,2-bis(dimethoxyphosphoryl)benzene, subject to the provisos that: when x is 2 or greater, each L may be the same as or different from the other L; and when the precursor compound is a .beta.-diketonate compound of formula (i), L is not phosphate or phosphine oxide.Type: GrantFiled: August 14, 1996Date of Patent: December 16, 1997Assignee: Advanced Technology Materials, Inc.Inventors: Timothy E. Glassman, Paul V. Chayka
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Patent number: 5689003Abstract: The invention relates to a novel ruthenium complex having the formula Ru(.eta..sup.3 --C.sub.6 H.sub.8 --PCy.sub.2)(PCy.sub.3)Cl, wherein Cy is cyclohexyl; its use in the preparation of RuHCl(H.sub.2)(PCy.sub.3).sub.2 and RuH.sub.2 (H.sub.2).sub.2 (PCy.sub.3).sub.2 ; and the use of the complexes as catalysts in hydrogenation, imination and reductive hydrolysis processes.Type: GrantFiled: May 8, 1996Date of Patent: November 18, 1997Assignee: E. I. Du Pont de Nemours and CompanyInventors: Richard Paul Beatty, Rocco Angelo Paciello
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Patent number: 5679812Abstract: A very efficient catalyst system for the polymerization of 1-olefins consists of an aluminoxane and a metallocene which is a compound of the formula I ##STR1## in which R.sup.1 and R.sup.2 denote hydrogen atoms, halogen atoms or hydrocarbon radicals and R.sup.3 and R.sup.4 are mononuclear or polynuclear hydrocarbon radicals which can form a sandwich structure with the central atom and which are linked to one another by a --R.sup.6.sub.m --R.sup.5 --R.sup.7.sub.n -- bridge containing a hetero atom and consisting of one or several members.The catalyst system produces polymers having a high molecular weight and excellent grain morphology.Type: GrantFiled: June 7, 1995Date of Patent: October 21, 1997Assignee: Hoechst AktiengesellschaftInventors: Andreas Winter, Volker Dolle, Jurgen Rohrmann, Walter Spaleck
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Patent number: 5679811Abstract: A very efficient catalyst system for the polymerization of 1-olefins consists of an aluminoxane and a metallocene which is a compound of the formula I ##STR1## in which R.sup.1 and R.sup.2 denote hydrogen atoms, halogen atoms or hydrocarbon radicals and R.sup.3 and R.sup.4 are mononuclear or polynuclear hydrocarbon radicals which can form a sandwich structure with the central atom and which are linked to one another by a --R.sup.6.sub.m --R.sup.5 --R.sup.7.sub.n -- bridge containing a hetero atom and consisting of one or several members.The catalyst system produces polymers having a high molecular weight.Type: GrantFiled: May 30, 1995Date of Patent: October 21, 1997Assignee: Hoechst AktiengesellschaftInventors: Andreas Winter, Volker Dolle, Martin Antberg, Jurgen Rohrmann, Walter Spaleck
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Patent number: 5670679Abstract: A process is disclosed for the manufacture of product compounds of the formula HC(R.sup.1).sub.2 C(R.sup.1).sub.2 C(R.sup.2).sub.2 C(R.sup.2).sub.2 H wherein each R.sup.1 is independently selected from the group consisting of H, F, Cl, CN, R, OR, CO.sub.2 R, C(O)R, OC(O)R, R.sup.f, OR.sup.f, CO.sub.2 R.sup.f C(O)R.sup.f and OC(O)R.sup.f where R is a hydrocarbyl group and R.sup.f is a C.sub.1 to C.sub.10 polyfluoroalkyl group, provided that at least one R.sup.1 is F, and wherein each R.sup.2 is independently selected from the group consisting of H, F, Cl, CN, R, OR, CO.sub.2 R, C(O)R, OC(O)R, R.sup.f, OR.sup.f, CO.sub.2 R.sup.f, C(O)R.sup.f, OC(O)R.sup.f and difunctional linkages where an R.sup.2 group on each of two adjacent carbon atoms together form a link selected from the group consisting of --CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH(CH.sub.3 --, --CH.sub.2 CH(CH.sub.3)CH.sub.2 --, --C(O)OC(O)--, and norborndiyl.Type: GrantFiled: June 2, 1995Date of Patent: September 23, 1997Assignee: E. I. Du Pont de Nemours and CompanyInventors: Ralph Thomas Baker, Richard Paul Beatty, William Brown Farnham, Robert Lewis Wallace, Jr.
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Patent number: 5658494Abstract: Novel compounds obtainable by reacting together an imido-reagent such as diphenylphosphonimido-triphenylphosphorane), or a phosphine oxide such as p-tolyldiphenylphosphine oxide, with a chelate of a transition or lanthanide or actinide metal, such as tris(dibenzoylmethide)europium III, have the property of fluorescing in UV radiation. The invention includes solid polymer bodies containing such compounds, or chelates of transition or lanthanide or actinide metals generally, the bodies having the property of emitting light or infra-red radiation when subjected to a flux of ultra-violet or ionising radiation by virtue of internally generated, e.g. by tritium ionising radiation. The body is preferably of polystyrene formed by polymerising the monomer in the presence of the compound or metal chelate.Type: GrantFiled: May 22, 1995Date of Patent: August 19, 1997Assignee: Amersham International plcInventors: Colin David Bell, John Hewer Coles Howse, Nigel Bosworth, David Martin James
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Patent number: 5646323Abstract: In accordance with the present invention there is provided a cyclopentadienyl-type ligand represented by the formula ZA, wherein Z is a cyclopentadienyl-type group, wherein A is --YPR.sub.2, --YNR.sub.2, or --NR.sub.2, wherein Y is an alkylene group containing 1 to 24 carbon atoms, wherein each R is individually selected from alkyl groups containing 1 to 20 carbon atoms. Another aspect of the invention is to provide a metallocene represented by the formula ZAMX.sub.3, wherein Z and A are as described above, M is a Group IVB or VB transition metal, and X is a halide. Other aspects of the present invention include catalyst systems comprising the metallocenes and an organoaluminoxane, processes for preparing the above defined ligands, metallocenes and catalyst systems, and polymerization processes employing the catalyst systems.Type: GrantFiled: May 19, 1995Date of Patent: July 8, 1997Assignee: Phillips Petroleum CompanyInventors: Krisztina Frey, Gabriele von Massow, Helmut G. Alt, M. Bruce Welch
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Patent number: 5631393Abstract: The invention relates to palladium compounds containing as ligands compounds of the formula (I) ##STR1## where Ar is C.sub.6 H.sub.4 SO.sub.3 M, M is hydrogen, ammonium, a monovalent metal or one equivalent of a polyvalent metal and Ph is the phenyl radical and n, m are zero, 1 or 2 and x, y, u, v are zero, 1 or 2.Type: GrantFiled: May 2, 1995Date of Patent: May 20, 1997Assignee: Hoechst AktiengesellschaftInventors: Christian Kohlpaintner, Matthias Beller
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Patent number: 5621128Abstract: Compounds of the formula I ##STR1## in which the phenyl rings of the biphenyl molecule can be substituted with up to 8 fluorine and/or chlorine atoms are suitable as catalysts.Type: GrantFiled: June 28, 1995Date of Patent: April 15, 1997Assignee: Hoechst AktiengesellschaftInventor: Joachim-Heiner Jendralla
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Patent number: 5621129Abstract: A tertiary phosphine compound of the formula (1): ##STR1## in which R.sup.1 and R.sup.1' are hydrogen atoms or together form --CH.dbd.CH--CH.dbd.CH--; R.sup.2 and R.sup.3 together form a group of the formula (a): ##STR2## in which --.circle-solid. represent a bond to be bonded to the R.sup.3 group, and --.smallcircle. represents a bond to be bonded to the R.sup.2 group when R.sup.1 and R.sup.1 ' together form --CH.dbd.CH--CH.dbd.CH--, or when R.sup.1 is a hydrogen atom, R.sup.2 and R.sup.3 together form --CH.dbd.CH--CH.dbd.CH-- or R.sup.2 is a hydrogen atom and R.sup.3 is a substituted or unsubstituted alkyl group, or a substituted or unsubstituted phenyl group; A.sup.1 is a 3-trifluoromethylphenyl group or a 3,5-bis(trifluoromethyl)phenyl group when R.sup.1 is a hydrogen atom and R.sup.2 and R.sup.3 together form --CH.dbd.CH--CH.dbd.CH--, or a substituted or unsubstituted phenyl group when R.sup.1 is not a hydrogen atom or when R.sup.2 and R.sup.3 do not together form --CH.dbd.CH--CH.dbd.CH--.Type: GrantFiled: March 7, 1996Date of Patent: April 15, 1997Assignee: Sumitomo Chemical Co., Ltd.Inventors: Tamio Hayashi, Masayoshi Minai, Kazunori Iwakura
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Patent number: 5599962Abstract: This invention relates to a process for the preparation of ruthenium complexes of the formula RuH.sub.2 L.sub.2 (PR.sub.3).sub.2, wherein each L is independently H.sub.2 or an additional equivalent of PR.sub.3, and each R is independently H, a hydrocarbyl group, or an assembly of at least two hydrocarbyl groups connected by ether or amine linkages, comprising contacting a source of ruthenium and PR.sub.3 with gaseous hydrogen in the presence of a strong base, a phase transfer catalyst, water and an organic solvent; and the use of certain classes of ruthenium complexes as catalysts in hydrogenation, and reductive hydrolysis processes.Type: GrantFiled: January 31, 1995Date of Patent: February 4, 1997Assignee: E. I. Du Pont de Nemours and CompanyInventors: Richard P. Beatty, Rocco A. Paciello
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Patent number: 5565398Abstract: Sulfonated diphosphines of the formula ##STR1## in which Ar is m--C.sub.6 H.sub.4 --SO.sub.3 M, M is hydrogen, ammonium, a monovalent metal, or the chemical equivalent of a polyvalent metal; Ph is phenyl; the m's are individually 1 or 2, and the n's are individually 0, 1, or 2. A method of their preparation and the hydroformylation of olefins and olefinically unsaturated compounds using these compounds as a constituent of water-soluble catalyst systems are also disclosed.Type: GrantFiled: November 2, 1995Date of Patent: October 15, 1996Assignee: Hoechst AktiengesellschaftInventors: Wolfgang A. Herrmann, Rainer Manetsberger, Helmut Bahrmann, Christian Kohlpaintner
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Patent number: 5561231Abstract: Transition metal-containing organosiloxanes of at least three organosiloxane units, comprising at least one transition metal complex, chemically bonded via ligands selected from among amino, phosphino or sulfido groups of Pt, Pd, Rh, Ru, Os or Ir, excluding those organosiloxanes which contain exclusively Pt(O) complexes bonded via amino ligands, are used as homogeneous hydrosilylation catalysts.Type: GrantFiled: July 19, 1994Date of Patent: October 1, 1996Assignee: Wacker-Chemie GmbHInventors: Jochen Dauth, Bernward Deubzer, Hans Bindl, Udo Peetz
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Patent number: 5559262Abstract: This invention relates to a process of preparing a ruthenium complex of the formula RuH.sub.2 (PR.sub.3).sub.2 L.sub.2 wherein PR.sub.3 is an organophosphoms ligand and L is H.sub.2 or PR.sub.3 ; a catalyst comprising at least one ruthenium complex having the formula RuH.sub.2 (PR.sub.3)L.sup.1.sub.3 wherein L.sup.1 is a neutral electron pair donor ligand; a process for preparing the catalyst and its use in situ in the hydrogenation of nitriles.Type: GrantFiled: January 31, 1995Date of Patent: September 24, 1996Assignee: E. I. Du Pont de Nemours and CompanyInventors: Richard P. Beatty, Rocco A. Paciello
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Patent number: 5556998Abstract: The present invention provides a novel transition metal complex which catalyzes asymmetric hydrogenation reaction. The present invention also provides a process for the preparation of the foregoing novel complex. The present invention further provides an asymmetric hydrogenation catalyst comprising the foregoing novel complex.Type: GrantFiled: March 13, 1995Date of Patent: September 17, 1996Assignee: Takasago International CorporationInventors: Akira Miyashita, Takeshi Chiba, Hiroyuki Nohira, Hidemasa Takaya
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Patent number: 5554778Abstract: The invention relates to a novel ruthenium complex having the formula Ru(.eta..sup.3 -C.sub.6 H.sub.8 -PCy.sub.2)(PCy.sub.3)Cl, wherein Cy is cyclohexyl; its use in the preparation of RuHCl(H.sub.2)(PCy.sub.3).sub.2 and RuH.sub.2 (H.sub.2).sub.2 (PCy.sub.3).sub.2 ; and the use of the complexes as catalysts in hydrogenation, imination and reductive hydrolysis processes.Type: GrantFiled: January 31, 1995Date of Patent: September 10, 1996Assignee: E. I. Du Pont de Nemours and CompanyInventors: Richard P. Beatty, Rocco A. Paciello
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Patent number: 5554777Abstract: Novel catalyst compositions comprising a cationic transition metal complex containing palladium, a mono-, di-, or tridendate ligand, and an anion are disclosed. The novel catalyst compositions can be used in a process for polymerizing carbon monoxide and at least one ethylenically unsaturated hydrocarbon to produce linear alternating polymers. Processes for preparing the novel catalyst compositions are also disclosed.Type: GrantFiled: July 8, 1994Date of Patent: September 10, 1996Assignee: The Dow Chemical CompamyInventors: John G. Hefner, Brian W. S. Kolthammer
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Patent number: 5545769Abstract: A process is disclosed for the manufacture of product compounds of the formula HC(R.sup.1).sub.2 C(R.sup.1).sub.2 C(R.sup.2).sub.2 H wherein each R.sup.1 is independently selected from the group consisting of H, F, Cl, CN, R, OR, CO.sub.2 R, C(O)R, OC(O)R, R.sup.f, OR.sup.f, CO.sub.2 R.sup.f, C(O)R.sup.f and OC(O)R.sup.f where R is a hydrocarbyl group and R.sup.f is a C.sub.1 to C.sub.10 polyfluoroalkyl group, provided that at least one R.sup.1 is F, and wherein each R.sup.2 is independently selected from the group consisting of H, F, Cl, CN, R, OR, CO.sub.2 R, C(O)R, OC(O)R, R.sup.f, OR.sup.f, CO.sub.2 R.sup.f, C(O)R.sup.f, OC(O)R.sup.f and difunctional linkages where an R.sup.2 group on each of two adjacent carbon atoms together form a link selected from the group consisting of --CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 --, --CH.sub.2 CH.sub.2 CH(CH.sub.3)--, --CH.sub.2 CH(CH.sub.3)CH.sub.2 --, --C(O)OC(O)--, and norborndiyl.Type: GrantFiled: September 29, 1994Date of Patent: August 13, 1996Assignee: E. I. Du Pont de Nemours and CompanyInventors: Ralph T. Baker, Richard P. Beatty, William B. Farnham, Robert L. Wallace, Jr.
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Tetrasulfonated diphosphine compounds and metal complexes thereof for asymmetric catalytic reactions
Patent number: 5536858Abstract: The invention is concerned with novel water-soluble racemic or optically active compounds of formulae ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently signify lower alkyl or lower alkoxy;m and n are 0, 1 or 2; andX signifies hydrogen, an alkali :metal, the equivalent of an earthalkali metal or an ammonium ion;with the provision that R.sup.3 is in position 4 or 5 and R.sup.4 is in position 4' or 5'. The invention is also concerned with complexes of such compounds with a metal of Group VIII. These complexes are, useful as catalysts for asymmetric hydrogenation and for enantioselective hydrogen displacement in prochiral allylic systems.Type: GrantFiled: December 2, 1994Date of Patent: July 16, 1996Assignee: Hoffmann-La Roche Inc.Inventors: Michel Lalonde, Rudolf Schmid -
Patent number: 5532395Abstract: This invention relates to novel chiral 1,4-diol cyclic sulfates and their use as precursors in the preparation of chiral phospholane ligands, and chiral complexes useful as catalysts for carrying out enantioselective reactions.Type: GrantFiled: May 24, 1995Date of Patent: July 2, 1996Assignee: E. I. Du Pont de Nemours and CompanyInventor: Mark J. Burk