Exactly Three Carbons Bonded Directly To The Phosphorus (e.g., Triphenylphosphines, Etc.) Patents (Class 556/21)
-
Patent number: 5530150Abstract: A phosphine compound represented by one of the formulas: ##STR1## wherein R.sup.1 and R.sup.2, which may be the same or different, each represent a phenyl group or a phenyl group substituted with a halogen atom or a lower alkyl group or taken together form a divalent hydrocarbon group; and R.sup.3 and R.sup.4, which may be the same or different, each represent a lower alkyl group, a phenyl group or a phenyl group substituted with a halogen atom, a lower alkyl group or a lower alkoxy group or taken together form a divalent hydrocarbon group, and wherein R.sup.6 and R.sup.6' which may be the same or different, each represent a hydrogen atom, a lower alkyl group or a lower alkoxy group; R.sup.5, R.sup.5', R.sup.11 and R.sup.11' which may be the same or different, each represent a hydrogen atom, a lower alkyl group, a lower alkoxy group or a halogen atom; or a pair of R.sup.5 and R.sup.6 or a pair of R.sup.5' and R.sup.6' may form a ring; R.sup.7 and R.sup.Type: GrantFiled: October 12, 1994Date of Patent: June 25, 1996Assignee: Takasago International CorporationInventors: Hidemasa Takaya, Nozomu Sakai, Kyoko Tamao, Satoshi Mano, Hidenori Kumobayashi, Tetsuo Tomita, Takao Saito, Kazuhiko Matsumura, Yasushi Kato, Noboru Sayo
-
Patent number: 5523437Abstract: A tertiary phosphine compound of the formula (1): ##STR1## wherein R.sup.1 and R.sup.2 represent independently from each other a hydrogen atom or a methyl group, or together form --CH.dbd.CH--CH.dbd.CH--; R.sup.3 is a hydrogen atom or a cycloalkyl group having 5 to 7 carbon atoms or a lower alkyl group which may be substituted with a halogen atom, a lower alkoxy group, a lower alkoxyalkoxy group or a phenyl group; X.sup.1 is a halogen atom when both R.sup.1 and R.sup.2 are hydrogen atoms, or a hydrogen atom, a halogen atom, a lower alkyl group or a lower alkoxy group when at least one of R.sup.1 and R.sup.2 is not a hydrogen atoms; and m is an integer of 1 to 5, which is useful as a ligand of a transition metal complex that can catalyze various reactions.Type: GrantFiled: July 26, 1994Date of Patent: June 4, 1996Assignee: Sumitomo Chemical Co., Ltd.Inventors: Tamio Hayashi, Yasuhiro Uozumi, Kazunori Iwakura, Isao Kurimoto, Masayoshi Minai
-
Patent number: 5510503Abstract: The invention relates to novel enantiomerically pure bisphosphines of the general formula (I) ##STR1## in which R, R.sup.1 and R.sup.2 have the meanings given in the description, a process for the preparation thereof and the use thereof in metal complexes as catalysts for asymmetric hydrogenations.Type: GrantFiled: September 2, 1994Date of Patent: April 23, 1996Assignee: Bayer AktiengesellschaftInventors: Christian Laue, Georg Schroder, Dieter Arlt, Rolf Grosser
-
Patent number: 5504232Abstract: A highly effective catalyst system for the polymerization of olefins comprises a cocatalyst, preferably an aluminoxane, and a metallocene of the formula I ##STR1## where M.sup.1 =Zr or Hf, R.sup.1 and R.sup.2 =(C.sub.1 -C.sub.4)-alkyl or chlorine, R.sup.3, with the proviso that at least one of the radicals R.sup.3 is not hydrogen, =hydrogen, F, Cl, --OR.sup.7, --NR.sup.7 R.sup.8, --P(O)R.sup.7 R.sup.8, --P(OR.sup.7).sub.2 or SR.sup.7, R.sup.4 is a ##STR2## radical, and m plus n are zero or 1.Type: GrantFiled: August 3, 1993Date of Patent: April 2, 1996Assignee: Hoechst AktiengesellschaftInventors: Andreas Winter, Juergen Rohrmann, Martin Antberg, Walter Spaleck, Wolfgang A. Herrmann, Herbert Riepl
-
Patent number: 5474716Abstract: Disclosed are processes for the preparation of new bridged cyclopentadienylmagnesium compounds of the general formula Q(CpR.sub.a)(Cp'R'.sub.a ')Mg, and the use thereof for preparing bridged metallocenes.Type: GrantFiled: February 22, 1995Date of Patent: December 12, 1995Assignee: Witco GmbHInventor: Richard Lisowsky
-
Patent number: 5455365Abstract: Process for the preparation of an olefin polymer using metallocenes containing specifically substituted indenyl ligandsA highly effective catalyst system for the polymerization of olefins comprises a cocatalyst, preferably an aluminoxane, and a metallocene of the formula I ##STR1## in which, preferably M.sup.1 is Zr or Hf, R.sup.1 and R.sup.2 are alkyl or halogen, R.sup.5 is hydrogen or alkyl, R.sup.3 and R.sup.4 are alkyl, where R.sup.3, R.sup.4 and R.sup.5 may be halogenated, --(CR.sup.7 R.sup.8).sub.m --R.sup.6 --(CR.sup.7 R.sup.8).sub.n -- is a single- or multi-membered chain in which R.sup.6 may also be a (substituted) heteroatom, and m+n is zero or 1.Type: GrantFiled: August 3, 1993Date of Patent: October 3, 1995Assignee: Hoechst AGInventors: Andreas Winter, Frank Kueber, Walter Spaleck, Herbert Riepl, Wolfgang A. Herrmann, Volker Dolle, Juergen Rohrmann
-
Patent number: 5426216Abstract: The present invention relates to a process for the hydrogenation of ethylenically unsaturated organic compounds. This process is carried out in a homogeneous medium containing a hydrogenation catalyst formed by a complex of ruthenium with a phosphine, which comprises two allylic groups as ligands on the Ru.Type: GrantFiled: August 12, 1993Date of Patent: June 20, 1995Assignee: Society Nationale Elf AquitaineInventors: Jean-Pierre Genet, Sylvain Juge, Jean A. Laffitte, Catherine Pinel, Sergio Mallart
-
Patent number: 5412128Abstract: The catalyst for olefin polymerization of the present invention contains R.sub.k.sup.1 R.sub.l.sup.2 R.sub.m.sup.3 M(SO.sub.3 R.sup.4) (M=Zr, Ti or Hf; R.sup.1-3 =a group having a cyclopentadienyl skeleton) as a catalyst component of a transition metal compound. According to the catalyst of the invention, an olefin polymer having excellent particle properties can be prepared with high polymerization activities, and further a copolymer having a narrow composition distribution can be prepared when two or more monomers are copolymerized. Of the above-mentioned transition metal compounds, a compound represented by the following formula is a novel compound unknown so far and shows excellent catalytic properties. ##STR1## (Cp=a group having a cyclopentadienyl skeleton, X=SO.sub.3 R, a halogen atom, R, OR, NR.sub.n, S(O).sub.q R, SiR.sub.3 or P (O).sub.q R.sub.Type: GrantFiled: July 9, 1993Date of Patent: May 2, 1995Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Junichi Imuta, Junji Saito, Takashi Ueda, Teruaki Mukaiyama
-
Patent number: 5374752Abstract: A very active catalyst system for olefin polymerization comprises a cocatalyst, preferably an aluminoxane, and a metallocene of the formula I ##STR1## in which, preferably, M.sup.1 is Zr or Hf, R.sup.1 and R.sup.2 are alkyl or halogen, R.sup.3 is hydrogen, R.sup.4 to R.sup.6 and alkyl or aryl, --(CR.sup.8 R.sup.9).sub.m --R.sup.7 --(CR.sup.8 R.sup.9).sub.n is a single- or multi-membered chain, in which R' can also be a (substituted) hetero atom, and m+n is zero or 1.Type: GrantFiled: April 25, 1994Date of Patent: December 20, 1994Assignee: Hoechst AktiengesellschaftInventors: Andreas Winter, Jurgen Rohrmann, Volker Dolle, Frank Kuber
-
Patent number: 5360939Abstract: Novel homogeneous bimetallic hydroformylation catalysts, and processes utilizing these catalysts to convert alkenes, particularly alpha olefins, under mild conditions to a product rich in aldehydes, particularly a product containing a high ratio of linear:branched chain aldehydes. The catalysts can be produced from a binucleating tetratertiaryphosphine ligand capable of strongly coordinating two metal centers and holding them in general proximity to one another. Bimetallic catalyst precursors are produced which, on reaction with carbon monoxide and hydrogen, form the active bimetallic hydroformylation catalyst system.Type: GrantFiled: January 12, 1994Date of Patent: November 1, 1994Assignee: Board of Supervisors of Louisiana State University and Agricultural and Mechanical CollegeInventors: George G. Stanley, Scott A. Laneman
-
Patent number: 5352813Abstract: An improved process is provided for the carbonylation of methanol to acetic acid and/or its derivatives, especially methyl acetate, under mild reaction conditions using a novel catalyst precursor. The precursor is a transition metal complex having a heterodifunctional bidentate phosphorus--nitrogen ligand attached to the metal. The carbonylation reaction can now typically be carried out at 80.degree. C. and CO pressure of 40 p.s.i.g.Type: GrantFiled: September 3, 1991Date of Patent: October 4, 1994Assignee: University of AlbertaInventors: Ronald G. Cavell, Kattesh V. Katti
-
Patent number: 5346730Abstract: The deposition of a copper-containing layer on a substrate by decomposing, particularly by a CVD process, a compound corresponding to the formula (I)RO--Cu--L (I)in whichR represents a 1-aryl lower alkyl group, a branched, optionally substituted alkyl group with 3 to 6 carbon atoms, or an aryl group, andL represents (C1 to C6-alkyl)isonitrile, aryl isonitrile, carbon monoxide, dialkylaminodifluorophosphane, organyl difluorophosphane, triaryl phosphane, trialkyl phosphane, trifluorophosphane, or trichlorophosphane,is described, together with previously unknown compounds of formula (I) which may be used in the process.Type: GrantFiled: July 26, 1991Date of Patent: September 13, 1994Assignee: Kali-Chemie AGInventors: Thomas Kruck, Christian Terfloth
-
Patent number: 5344988Abstract: Disclosed are bis-phosphine compounds having the general formula ##STR1## wherein: each of A.sup.1, A.sup.2, A.sup.3 and A.sup.4 is an arylene radical wherein (i) each phosphorus atom P is bonded to a ring carbon atom of A.sup.1 and A.sup.2 and to a ring carbon atom of A.sup.3 and A.sup.4, (ii) A.sup.1 and A.sup.2, and A.sup.3 and A.sup.4 are bonded to each other by ring carbon atoms and (iii) each of the residues ##STR2## constitutes a 5-membered ring; each of A.sup.5 and A.sup.6 is an arylene radical wherein A.sup.5 and A.sup.6 are bonded to each other and to residues R.sup.1 --C--R.sup.2 and R.sup.3 --C--R.sup.4 by ring carbon atoms and R.sup.1 --C--R.sup.2 and R.sup.3 --C--R.sup.4 are connected to each other through a chain of 4 carbon atoms; andR.sup.1, R.sup.2, R.sup.3 and R.sup.4 each represents hydrogen or a hydrocarbyl radical containing up to about 8 carbon atoms.Type: GrantFiled: February 22, 1994Date of Patent: September 6, 1994Assignee: Eastman Chemical CompanyInventors: Thomas J. Devon, Gerald W. Phillips, Thomas A. Puckette, Jerome L. Stavinoha, Jeffrey J. Vanderbilt
-
Patent number: 5332846Abstract: Disclosed are bis-phosphine compounds having the general formula ##STR1## wherein: each of A.sup.1, A.sup.2, A.sup.3 and A.sup.4 is an arylene radical wherein (i) each phosphorus atom P is bonded to a ring carbon atom of A.sup.1 and A.sup.2 and to a ring carbon atom of A.sup.3 and A.sup.4, (ii) A.sup.1 and A.sup.2, and A.sup.3 and A.sup.4 are bonded to each other by ring carbon atoms and (iii) each of the residues ##STR2## constitutes a 5-membered ring; each of A.sup.5 and A.sup.6 is an arylene radical wherein A.sup.5 and A.sup.6 are bonded to each other and to residues R.sup.1 --C--R.sup.2 and R.sup.3 --C--R.sup.4 by ring carbon atoms and R.sup.1 --C--R.sup.2 and R.sup.3 --C--R.sup.4 are connected to each other through a chain of 4 carbon atoms; andR.sup.1, R.sup.2, R.sup.3 and R.sup.4 each represents hydrogen or a hydrocarbyl radical containing up to about 8 carbon atoms.Type: GrantFiled: June 1, 1993Date of Patent: July 26, 1994Assignee: Eastman Kodak CompanyInventors: Thomas J. Devon, Gerald W. Phillips, Thomas A. Puckette, Jerome L. Stavinoha, Jeffrey J. Vanderbilt
-
Patent number: 5329033Abstract: A very effective catalyst system for olefin polymerization consists of a cocatalyst, preferably an aluminoxane, and a metallocene of the formula (I) ##STR1## in which, preferably, M.sup.1 is Zr, R.sup.1 and R.sup.2 are alkyl or halogen, R.sup.3 to R.sup.6 are alkyl, --(CR.sup.8 R.sup.9).sub.m --R.sup.7 --(CR.sup.8 R.sup.9).sub.n -- is a chain having one or more members, in which R.sup.7 can also be a (substituted) hetero atom, and m+n is zero or 1. The catalyst system leads to polymers of variable molecular weight and stereotacticity, depending on the substituents R.sup.3 to R.sup.6 chosen, at polymerization temperatures which are relevant in industry.Type: GrantFiled: October 25, 1993Date of Patent: July 12, 1994Assignee: Hoechst AktiengesellschaftInventors: Walter Spaleck, Jurgen Rohrmann, Martin Antberg
-
Patent number: 5324870Abstract: A process for producing an optically active 1-substituted-1,3-propanediol is disclosed, comprising hydrogenating a 3-substituted-3-oxopropanol or 3-substituted-3-oxopropanal in the presence of a ruthenium-phosphine complex represented by formula (I):[RuI(p-cymene)(R.sup.1 BINAP)]I.sub.3 (I)wherein R.sup.1 -BINAP represents an optically active tertiary phosphine represented by formula (II): ##STR1## wherein R.sup.1 represents a phenyl group which may be substituted with a lower alkyl group or a halogen atom at the p-position and/or m-position.Type: GrantFiled: November 23, 1993Date of Patent: June 28, 1994Assignee: Takasago International CorporationInventors: Noboru Sano, Noboru Sayo, Hidenori Kumobayashi
-
Patent number: 5324850Abstract: Method for the preparation of a chiral catalyst, comprised of an organic complex of ruthenium and phosphorus, consisting in heating a complex of ruthenium with a phosphine, within an organic liquid, inert in relation to substances in presence, the heated complex being based on a diene and an allylic compound; the product obtained following the heating is subjected to the action of an acid in an organic solvent.Type: GrantFiled: February 21, 1992Date of Patent: June 28, 1994Assignee: Societe Nationale Elf AquitaineInventors: Sylvain Juge, Jean-Pierre Genet, Sergio Mallart
-
Patent number: 5312939Abstract: Novel 2,2'-bis(dicyclopentylphosphino)-1,1'-binaphthyl represented by formula (I): ##STR1## and a transition metal complex using the same as a ligand, are disclosed. The transition metal complex is industrially excellent as a catalyst for various asymmetric synthesis reactions.Type: GrantFiled: July 10, 1991Date of Patent: May 17, 1994Assignee: Takasago International CorporationInventors: Yoji Hori, Hidenori Kumobayashi
-
Patent number: 5304666Abstract: A process for preparing the superconductive material MBa.sub.2 Cu.sub.3 O.sub.x, M being, inter alia, yttrium and x being from about 6.5-7 and a precursor material MBa.sub.2 Cu.sub.3 O.sub.y, y being from about 6-6.5, by controlled heating and cooling in a controlled atmosphere.Type: GrantFiled: April 7, 1992Date of Patent: April 19, 1994Assignee: E. I. Du Pont de Nemours and CompanyInventor: Stephan J. McLain
-
Patent number: 5286888Abstract: A ruthenium-phosphine complex is disclosed, represented by formula (I):[RuI(p-cymene)(R.sup.1 -BINAP)]I.sub.3 (I)where R.sup.1 -BINAP represents a tertiary phosphine represented by formula (II): ##STR1## wherein R.sup.1 represents a phenyl group which may be substituted with a lower alkyl group or a halogen atom at the p-position and/or m-position. A process for producing an optically active 1-substituted-1,3-propanediol is also disclosed, comprising hydrogenating a 3-substituted-3-oxopropanol or 3-substituted-3-oxopropanal in the presence of the ruthenium-phosphine complex of formula (I).Type: GrantFiled: October 22, 1992Date of Patent: February 15, 1994Assignee: Takasago International CorporationInventors: Noboru Sano, Noboru Sayo, Hidenori Kumobayashi
-
Patent number: 5276208Abstract: The novel metallocenes of the formula I ##STR1## in which, preferably, M.sup.1 is Zr or Hf, R.sup.1 and R.sup.2 are alkyl or halogen, R.sup.3 and R.sup.4 are hydrogen, R.sup.5 and R.sup.6 are alkyl or haloalkyl, --(CR.sup.8 R.sup.9).sub.m --R.sup.7 --(CR.sup.8 R.sup.9).sub.n -- is a single- or multi-membered chain in which R.sup.7 may also be a (substituted) hetero atom, m+n is zero or 1, and R.sup.10 is hydrogen, form, together with aluminoxanes as cocatalysts, a very effective catalyst system for the preparation of polyolefins of high stereospecificity and high melting point.Type: GrantFiled: November 8, 1991Date of Patent: January 4, 1994Assignee: Hoechst AktiengesellschaftInventors: Andreas Winter, Martin Antberg, Walter Spaleck, Jurgen Rohrmann, Volker Dolle
-
Patent number: 5268492Abstract: An optically active diphosphine having a bicyclo[2.2.1]heptane of the formula ##STR1## where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are difined in the specification and a metal complex comprising said optically active diphosphine are disclosed. A process for producing or purifying said optically active diphosphine is disclosed.Type: GrantFiled: August 27, 1992Date of Patent: December 7, 1993Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Keiji Yamamoto, Masahiro Miyazawa, Satoru Momose
-
Patent number: 5268479Abstract: A process is specified for the preparation of tertiary phosphines of the formulaR'PR.sub.2 or R.sub.2 P--[CH.sub.2 ].sub.3 --PR.sub.2in which R is an aryl, pyridyl or arylsulfonic acid group and R' is an aryl, pyridyl, arylsulfonic acid or n-butyl group, which comprises reacting phosphines of the formulaH.sub.n PR".sub.3-n or H.sub.2 P--[CH.sub.2 ].sub.3 --PH.sub.2in which R" is hydrogen or an n-butyl, aryl or pyridyl group and n is 1 or 2 with a halogen compound of the formulaX-R,in which R has the abovementioned meaning and X is fluorine, chlorine or bromine, in the presence of powdered potassium hydroxide and dimethyl sulfoxide and/or dimethoxyethane at temperatures between 0 and 100.degree. C., at least 1 mol of potassium hydroxide being used per mole of halogen compound.Type: GrantFiled: December 2, 1992Date of Patent: December 7, 1993Assignee: Hoechst AktiengesellschaftInventors: Othmar Stelzer, Klaus-Peter Langhans, Norbert Weferling
-
Patent number: 5237106Abstract: A process for improving the catalytic activity of a partially deactivated solubilized rhodium-tertiary organophosphine complex hydroformylation catalyst by treating it with propargyl alcohol and a carboxylic acid.Type: GrantFiled: January 24, 1992Date of Patent: August 17, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: James E. Babin, David R. Bryant, Arnold M. Harrison, David J. Miller
-
Patent number: 5233064Abstract: Palladium complexes having the general formula Pd(R'CO.sub.2).sub.2 X where R' is C.sub.1 to C.sub.10 alkyl or C.sub.6 to C.sub.10 aryl and X is a chelating ligand of formula (R.sup.2).sub.2 PYP(R.sup.2).sub.2 where the R.sup.2 groups are independently selected from C.sub.1 to C.sub.4 alkyl, phenyl or alkoxy substituted phenyl, and Y is --(CH.sub.2).sub.n -- where n=2 to 4 are provided. The complexes may be prepared by reacting the compounds Pd(R'CO.sub.2).sub.2 and (R.sup.2).sub.2 PYP(R.sup.2).sub.2 together in an aromatic solvent at a temperature of less than 60.degree. C. in amounts such that the molar ratio of the two compounds is in the range 1.2:1 to 1:1.2.Type: GrantFiled: April 9, 1992Date of Patent: August 3, 1993Assignee: The British Petroleum Company, p.l.c.Inventor: Neil A. Cooley
-
Patent number: 5231202Abstract: A phosphine compound represented by formula (I): ##STR1## wherein Ph represents a phenyl group; and R represents a lower alkyl group or --OR.sup.1, wherein R.sup.1 represents a hydrogen atom, a cycloalkyl group having from 5 to 7 carbon atoms, or an alkyl group having from 1 to 6 carbon atoms which may be substituted with a halogen atom, a lower alkoxy group, a lower alkoxy group-substituted lower alkoxy group, or a phenyl group, and a transition metal complex using the phosphine compound (I) as a ligand are disclosed. The transition metal complex, when used as a catalyst for various enantioselective synthesis reactions, e.g., enantioselective silylation reaction, provides a desired product in high yield at high optical purity. The absolute configuration of the product can be arbitrarily selected by selecting the optical isomer of the ligand in the transition metal complex catalyst.Type: GrantFiled: March 12, 1992Date of Patent: July 27, 1993Assignee: Takasago International CorporationInventors: Tamio Hayashi, Yasuhiro Uozumi, Akiko Yamazaki, Hidenori Kumobayashi
-
Patent number: 5223632Abstract: A 2,2'-bis[di-(3,5-dialkylphenyl)phosphino]-1,1'-binaphthyl represented by formula (I): ##STR1## wherein R represents a lower alkyl group, is disclosed. A transition metal complex comprising a transition metal and a 2,2'-bis[di(3,5-dialkylphenyl)phosphino]-1,1'-binaphthyl represented by formula (I) as a ligand is also disclosed.Type: GrantFiled: March 1, 1991Date of Patent: June 29, 1993Assignee: Takasago International CorporationInventors: Takerou Ishizaki, Yoji Hori, Hidenori Kumobayashi
-
Patent number: 5223648Abstract: The hydroformylation of olefins and olefinically unsaturated compounds in the presence of a water-soluble rhodium complex compound Which contains, as a ligand, at least one sulfonated diphosphine, and a catalyst therefor.Type: GrantFiled: August 25, 1992Date of Patent: June 29, 1993Assignee: Hoechst AktiengesellschaftInventors: Wolfgang Herrmann, Christian Kohlpaintner, Helmut Bahrmann
-
Patent number: 5216186Abstract: Crystalline palladium tetrakis (triphenylphosphine) which exhibits a specific powder X-ray pattern and is excellent in storage stability is obtained by allowing palladium chloride to react with triphenylphosphine in aprotic polar solvents, treating the reaction mixture with an aqueous hydrazine solution, collecting the resulting crystals by filtration, washing with alcohols and further washing with hydrocarbon solvents.Type: GrantFiled: December 19, 1991Date of Patent: June 1, 1993Assignee: Sumitomo Pharmaceuticals Co., Ltd.Inventors: Makoto Sunagawa, Haruki Matsumura, Yutaka Kitamura
-
Patent number: 5206399Abstract: 2,2'-Bis(diphenylphosphino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl represented by formula (I). ##STR1## is disclosed. A transition metal complex containing the same, a process for producing 2,2'-Bis(diphenylphosphino)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl, and a process for producing 2,2'-bis(diphenylphosphinyl)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl are also disclosed.Type: GrantFiled: October 1, 1991Date of Patent: April 27, 1993Assignee: Takasago International CorporationInventors: Noboru Sayo, Hidenori Kumobayashi
-
Patent number: 5206396Abstract: Octyl ethers and octadienyl ethers of glucose, sucrose, bisphenol A, 4-substituted-2,2,6,6-tetramethylpiperidines are disclosed. Compositions comprised of a mixture of octyl ethers of glucose and sucrose and those containing octadienyl ethers of sugar acids and ring-opened epoxidized octadienyl ethers are also disclosed as are telomerization processes.Type: GrantFiled: July 25, 1990Date of Patent: April 27, 1993Assignee: Henkel Research CorporationInventors: Bert Gruber, Kenneth J. Weese, Steven M. Hoagland, Hans-Peter Mueller, Karlheinz Hill, Arno Behr, James R. Tucker
-
Patent number: 5202472Abstract: A process for the asymmetric reduction of carboxylic acids of the formula ##STR1## or the amine salts thereof, where R and R.sub.1 are the same or different and are hydrogen, alkyl, cycloalkyl or haloalkyl and Ar is aryl or substituted aryl is disclosed.Type: GrantFiled: June 17, 1991Date of Patent: April 13, 1993Assignee: Ethyl CorporationInventors: Thanikavelu Manimaran, W. Dirk Klobucar, Charles H. Kolich
-
Patent number: 5200380Abstract: The hydroformylation of olefins and olefinically unsaturated compounds in the presence of a water-soluble rhodium complex compound which contains, as a ligand, at least one sulfonated diphosphine, and a catalyst therefor.Type: GrantFiled: December 6, 1991Date of Patent: April 6, 1993Assignee: Hoechst AktiengesellschaftInventors: Wolfgang Herrmann, Christian Kohlpaintner, Helmut Bahrmann
-
Patent number: 5200539Abstract: Novel homogeneous bimetallic hydroformylation catalysts, and processes utilizing these catalysts to convert alkenes, particularly alpha olefins, under mild conditions to a product rich in aldehydes, particularly a product containing a high ratio of linear:branched chain aldehydes. The catalysts can be produced from a binucleating tetratertiaryphosphine ligand capable of strongly coordinating two metal centers and holding them in general proximity to one another. Bimetallic catalyst precursors are produced which, on reaction with carbon monoxide and hydrogen forms the active bimetallic hydroformylation catalyst system.Type: GrantFiled: August 27, 1990Date of Patent: April 6, 1993Assignee: Louisiana State University Board of Supervisors, a governing body of Louisiana State University Agricultural and Mechanical CollegeInventors: George G. Stanley, Scott A. Laneman
-
Patent number: 5198576Abstract: Bicyclooctyl phosphines are disclosed having the formula: ##STR1## where R is C.sub.1 to C.sub.6 linear or branched alkyl, phenyl, substituted phenyl, halo, or C.sub.1 or C.sub.6 alkoxy; Ar is phenyl, substituted phenyl, naphthyl or substituted naphthyl; and x is 0 or 1.These phosphines are treated with ruthenium compounds to form a complex of the formula Ru.sub.x H.sub.y Cl.sub.z (anthraphos-m).sub.2 (S).sub.p, where S is a tertiary amine; and when y is 0, then x is 2, z is 4 and p is 1; and when y is 1, then x is 1, z is 1 and p is 0; where anthraphos-m is: ##STR2## where R is C.sub.1 to C.sub.6 linear or branched alkyl, phenyl, substituted phenyl, C.sub.1 to C.sub.6 linear or branched alkoxy or halo; Ar is phenyl or substituted phenyl or naphthyl or substituted naphthyl; and m is 0 or 1.The complex is useful in a process for the asymmetric reduction of olefinic carboxylic acids of the formula: ##STR3## where R.sub.1 and R.sub.Type: GrantFiled: August 26, 1991Date of Patent: March 30, 1993Assignee: Ethyl CorporationInventor: Ralph T. Scannell
-
Patent number: 5198562Abstract: A ruthenium-phosphine complex represented by formula (I): ##STR1## wherein R.sup.2 -BINAP represents a teritary phosphine compound represented by formula (II): ##STR2## wherein R.sup.2 represents a hydrogen atom, a methyl group, a methoxy group, or a t-butyl group; X represents a halogen atom; and R and R.sup.1, which may be the same or different, each represent a phenyl group or a substituted phenyl group, and a ruthenium-phosphine complex represented by formula (III): ##STR3## wherein R and R.sup.1 are as defined above; and dma represents N,N-dimethylacetamide, which is an intermediate for synthesizing the ruthenium-phosphine complex of formula (I), are disclosed. The complex of formula (I) is useful as a catalyst for general syntheses with its ligand being an optically inactive compound or for asymmetric syntheses with its ligand being an optically active compound and, also, can be prepared at a low cost.Type: GrantFiled: August 1, 1991Date of Patent: March 30, 1993Assignee: Takasago International CorporationInventors: Ryoji Noyori, Masato Kitamura, Noboru Sayo, Hidenori Kumobayashi, Martin F. Giles
-
Patent number: 5190905Abstract: A process for the asymmetric reduction of carboxylic acids of the formula ##STR1## or the amine salts thereof, where R and R.sub.1 are the same or different and are hydrogen, alkyl, cycloalkyl or haloalkyl and Ar is aryl or substituted aryl is disclosed.Type: GrantFiled: June 17, 1991Date of Patent: March 2, 1993Assignee: Ethyl CorporationInventors: Charles H. Kolich, Thanikavelu Manimaran, W. Dirk Klobucar
-
Patent number: 5191095Abstract: A process for the asymmetric reduction of olefinic amides of the formula ##STR1## where R and R.sub.1 are the same or different and are hydrogen, alkyl, cycloalkyl or haloalkyl and Ar is aryl or substituted aryl is disclosed.Type: GrantFiled: June 17, 1991Date of Patent: March 2, 1993Assignee: Ethyl CorporationInventors: Thanikavelu Manimaran, W. Dirk Klobucar, Charles H. Kolich
-
Patent number: 5187281Abstract: A process for the asymmetric reduction of carboxylic acids of the formula ##STR1## or the amine salts thereof, where R and R.sub.1 are the same or different and are hydrogen, alkyl, cycloalkyl or haloalkyl and Ar is aryl or substituted aryl is disclosed.Type: GrantFiled: June 17, 1991Date of Patent: February 16, 1993Assignee: Ethyl CorporationInventors: Charles H. Kolich, Thanikavelu Manimaran, W. Dirk Klobucar
-
Patent number: 5187136Abstract: A process for the asymmetric reduction of carboxylic acids of the formula ##STR1## or the amine salts thereof, where R and R.sub.1 are the same or different and are hydrogen, alkyl, cycloalkyl or haloalkyl and Ar is aryl or substituted aryl is disclosed.Type: GrantFiled: June 17, 1991Date of Patent: February 16, 1993Assignee: Ethyl CorporationInventors: W. Dirk Klobucar, Charles H. Kolich, Thanikavelu Manimaran
-
Patent number: 5187135Abstract: A process for the asymmetric reduction of carboxylic acids of the formula ##STR1## or the amine salts thereof, where R and R.sub.1 are the same or different and are hydrogen, alkyl, cycloalkyl or haloalkyl and Ar is aryl or substituted aryl is disclosed.Type: GrantFiled: June 17, 1991Date of Patent: February 16, 1993Assignee: Ethyl CorporationInventors: Charles H. Kolich, Thanikavelu Manimaran, W. Dirk Klobucar
-
Patent number: 5177231Abstract: A process for the asymmetric reduction of carboxylic acids of the formula ##STR1## or the amine salts thereof, where R and R.sub.1 are the same or different and are hydrogen, alkyl, cycloalkyl or haloalkyl and Ar is aryl or substituted aryl is disclosed.Type: GrantFiled: June 17, 1991Date of Patent: January 5, 1993Assignee: Ethyl CorporationInventors: Thanikavelu Manimaran, W. Dirk Klobucar, Charles H. Kolich
-
Patent number: 5159093Abstract: An iridium-optically active phosphine complex represented by formula (I):[H.sub.2 Ir(L.sup.1)(L.sup.2)]Y (I)wherein L.sup.1 represents an optically active phosphine compound represented by formula (II): ##STR1## wherein Ar represents a phenyl group or a p- and/or m-lower alkyl-substituted phenyl group, or formula (III): ##STR2## L.sup.2 represents a tertiary phosphine compound represented by formula (IV): ##STR3## wherein Z represents a lower alkoxy group or a di-lower alkylamino group; and A represents an integer of from 1 to 3; Y represents BF.sub.4, PF.sub.6, ClO.sub.4, or BPh.sub.4, wherein Ph represents a phenyl group, and a process for producing an optically active alcohol using the above complex as an enantioselective catalyst are disclosed. The complex exhibits excellent catalytic activity to give high enantioselective yields in enantioselective synthesis, particularly enantioselective hydrogenation.Type: GrantFiled: October 1, 1991Date of Patent: October 27, 1992Assignee: Takasago International CorporationInventors: Takanao Taketomi, Susumu Akutagawa, Hidenori Kumobayashi, Hidemasa Takaya, Kazushi Mashima
-
Patent number: 5145819Abstract: The novel metallocenes of the formula I ##STR1## in which, preferably, M.sup.1 is Zr or Hf, R.sup.1 and R.sup.2 are alkyl or halogen, R.sup.3 and R.sup.4 are hydrogen, R.sup.5 and R.sup.6 are alkyl or haloalkyl, --(CR.sup.8 R.sup.9).sub.m --R.sup.7 --(CR.sup.8 R.sup.9).sub.n -- is a single- or multi-membered chain in which R.sup.7 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: GrantFiled: November 8, 1991Date of Patent: September 8, 1992Assignee: Hoechst AktiengesellschaftInventors: Andreas Winter, Martin Antberg, Walter Spaleck, Jurgen Rohrmann, Volker Dolle
-
Patent number: 5144050Abstract: Ru(BINAP) diketonate complexes manifest asymmetric hydrogenation catalytic activity with high reaction and conversion rates.Type: GrantFiled: October 1, 1991Date of Patent: September 1, 1992Assignee: Monsanto CompanyInventors: Albert S. C. Chan, Scott A. Laneman
-
Patent number: 5142063Abstract: The present invention describes novel chiral rhodium-diphosphine complexes having the formula[Rh(X) (Y) (Lp)]owherein X represents a residue of the formula X--COO.sup.- in which Z signifies a group ##STR1## aryl or substituted aryl, wherein R.sup.1, R.sup.2, R.sup.3 =hydrogen, halogen, lower alkyl, aryl-lower alkyl, perfluoro-C.sub.1-20 -alkyl, aryl, substituted aryl, the group --OR.sup.7, --(CH.sub.2).sub.m --COA or AOC--(CF.sub.2).sub.n, with the proviso that at least one of R.sup.1, R.sup.2, and R.sup.3 represents --OR.sup.7, aryl or substituted aryl,R.sup.4, R.sup.5, R.sup.6 =hydrogen, halogen, lower alkyl, aryl-lower alkyl, perfluoro--C.sub.1-20 -alkyl, aryl, substituted aryl, --(CH.sub.2).sub.m --COA or AOC--(CF.sub.2).sub.n,R.sup.7 =hydrogen, lower alkyl, partially or completely halogenated lower alkyl, aryl, substituted aryl or aryl-lower alkyl,A=The residue --OR or NR'.sub.Type: GrantFiled: November 20, 1990Date of Patent: August 25, 1992Assignee: Hoffmann-La Roche, Inc.Inventors: Emil A. Broger, Yvo Crameri
-
Patent number: 5118825Abstract: A ruthenium phosphine complex having catalytic, hydrogenation activity is disclosed. The catalyst as the formula ##STR1## wherein R and R' are the same or different and are C.sub.1 to C.sub.6 linear or branched alkyl; R" is hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl; R.sub.1 is C.sub.1 to C.sub.6 linear or branched alkyl; and n is an integer from 1 to 6.The phosphine complex is particularly useful in the asymmetric hydrogenation of unsaturated carboxylic acids or alkyl esters thereof.Type: GrantFiled: December 10, 1990Date of Patent: June 2, 1992Assignee: Ethyl CorporationInventor: Tse-Chong Wu
-
Patent number: 5087710Abstract: The invention pertains to rhenium (VII) compounds which are catalysts for metathesis of ordinary olefins (hydrocarbons) and functionalized olefins in a homogeneous phase and to methods of synthesizing these compounds. The rhenium compounds comprise a rhenium (VII) atom centrally linked to an alkylidene ligand, an alkylidyne ligand, and two other ligands of which at least one ligand is sufficiently electron withdrawing to render the rhenium atom significantly active for metathesis.Type: GrantFiled: January 4, 1990Date of Patent: February 11, 1992Assignee: Massachusetts Institute of TechnologyInventors: Richard R. Schrock, Robert Toreki
-
Patent number: 5057618Abstract: New complexes of the elements of Groups VIIA, VIIIA, and IB of the Periodic Table* with the trisodium salt of tris(m-sulfophenyl)phosphane as a complex ligand. The complexes are used as catalysts for hydrogenations for the water gas reactions, hydrocarbonyls, hydroformylations, oxidations, carbon-carbon cross-linking reactions (e.g. allene/alkine coupling), and additions of secondary amines to carbon-carbon double bonds.*according to the IUPAC version.Type: GrantFiled: November 30, 1989Date of Patent: October 15, 1991Assignee: Hoechst AktiengesellschaftInventors: Wolfgang A. Herrmann, Jurgen Kulpe, Jurgen Kellner, Herbert Riepl
-
Patent number: 5041574Abstract: A process for the preparation of cobalt carbonyl complexes by heating a mixture containing an inert hydrocarbon solvent, at least one cobalt compound which is soluble in the reaction mixture, a trialkylphosphine, carbon monoxide, and a heterogeneous hydrogenation catalyst.Type: GrantFiled: August 9, 1990Date of Patent: August 20, 1991Assignee: E. I. Du Pont de Nemours and CompanyInventor: Rocco A. Paciello