Benzene Ring Containing Patents (Class 568/17)
  • Patent number: 5723678
    Abstract: Acetylenic compounds of the general formula IR.sup.1 --C.tbd.C--CHR.sup.2 --CH.sub.2 --X Iwhere the substituents have the following meanings:R.sup.1 hydrogen, unsubstituted or substituted alkyl or aryl;R.sup.2 hydrogen or C.sub.1 -C.sub.4 -alkyl;X CN; COOR.sup.3 where R.sup.3 is C.sub.1 -C.sub.6 -alkyl or benzyl; C(O)R.sup.4 where R.sup.4 is hydrogen or C.sub.1 -C.sub.4 -alkyl,are prepared by reacting an alkyne of the formula IIR.sup.1 --C.tbd.C--H IIwith an .alpha.,.beta.-unsaturated compound of the formula IIIR.sup.2 HC.dbd.CH--X IIIin the presence of a homogeneous rhodium-phosphine catalyst, in a process wherein a catalyst with a bidentate or tridentate phosphine compound is used.
    Type: Grant
    Filed: April 12, 1996
    Date of Patent: March 3, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Thomas Ruhl, Jochem Henkelmann, Marc Heider, Peter Hofmann
  • Patent number: 5723642
    Abstract: Optically active phosphines of the general formula I or II ##STR1## where the variables have the following meanings: X is an optically active terpene radical,R is an unsubstituted or substituted phenyl radical,Y is a bridge member having 1-10 C atoms in the formula In is 1,2 or 3 andm is 0,1 or 2 with the proviso that n+m=3 in the formula IIn is 1 or 2 andm is 0 or 1 with the proviso that n+m=2, their preparation and use are described.
    Type: Grant
    Filed: May 6, 1996
    Date of Patent: March 3, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Rainer Sturmer, Lothar Laupichler, Paul Knochel, Falk Langer
  • Patent number: 5721292
    Abstract: Compounds of formula (I), in which X is oxygen or sulfur, R.sub.1, R.sub.2 and R.sub.3 independently of one another are a group (a), C.sub.2 -C.sub.8 alkenyl, phenyl which is unsubstituted or is substituted from one to four times with C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.12 alkoxy, C.sub.1 -C.sub.6 alkylthio and/or halogen, or are naphthyl which is unsubstituted or is substituted from one to four times with C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.12 alkoxy, C.sub.1 -C.sub.6 alkylthio and/or halogen, or are biphenyl which is unsubstituted or is substituted from one to four times with C.sub.1 -C.sub.12 alkyl, C.sub.1 -C.sub.12 alkoxy, C.sub.1 -C.sub.6 -alkylthio and/or halogen, or R.sub.1, R.sub.2 and R.sub.3 independently of one another are an O-, S- or N-containing 5- or 6-membered heterocyclic ring, R.sub.1 is in addition a group of formula (II), or R.sub.1 and R.sub.2 are linked to form a ring containing 4 to 10 carbon atoms which is unsubstituted or substituted by 1 to 6 C.sub.1 -C.sub.
    Type: Grant
    Filed: March 5, 1997
    Date of Patent: February 24, 1998
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: David George Leppard, Manfred Kohler, Gebhard Hug
  • Patent number: 5712403
    Abstract: A method for producing an unsaturated alcohol having a chain structure formed by oligomerization of a conjugated alkadiene, which comprises reacting a conjugated alkadiene and water in the presence of carbon dioxide by means of a palladium compound and a phosphorus compound having at least one trivalent phosphorus-oxygen single bond, as catalyst.
    Type: Grant
    Filed: October 8, 1996
    Date of Patent: January 27, 1998
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Keiichi Sato, Yoko Seto, Iwao Nakajima
  • Patent number: 5710338
    Abstract: Hydroformylation of alkenes to aldehydes in the presence of a rhodium complex catalyst is improved by the addition of a novel bidentate ligand of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.1 ' and R.sub.2 ' are organic radicals selected from alicyclic, aliphatic and aromatic groups of which at least one is preferably substituted with at least one electronegative moiety and the methylene groups are present at the trans-2,3 positions on the norbornane moiety. The invention also provides a novel method for producing the bidentate ligand and novel intermediate phosphine oxide and phosphinous acid compounds.
    Type: Grant
    Filed: April 10, 1996
    Date of Patent: January 20, 1998
    Assignee: Hoechst Celanese Corporation
    Inventors: Jerry D. Unruh, Brigitte E. Segmuller, Gabriel R. Chapa, Kent E. Pryor
  • Patent number: 5710339
    Abstract: 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: Grant
    Filed: June 13, 1996
    Date of Patent: January 20, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Christian Laue, Georg Schroder, Dieter Arlt
  • Patent number: 5710340
    Abstract: Phosphines having two aryl groups and one alkyl-substituted cycloalkyl group bonded to a phosphorus atom are formed by reacting an alkali metal diarylphosphide with a monoalkyl- or polyalkyl-substituted cycloalkyl mesylate or tosylate in which an alkyl group is in the 2-position, in a liquid reaction medium in which these reactants are soluble. This process avoids complications associated with prior known process technology for producing such phosphines. The phosphines are useful as ligands for making noble metal catalysts.
    Type: Grant
    Filed: April 29, 1996
    Date of Patent: January 20, 1998
    Assignee: Albemarle Corporation
    Inventor: K. Pushpananda A. Senaratne
  • Patent number: 5710337
    Abstract: Hydroformylation of alkenes to aldehydes in the presence of a rhodium complex catalyst is improved by the addition of a novel bidentate ligand of the formula ##STR1## wherein R.sub.1, R.sub.2, R.sub.1 ' and R.sub.2 ' are organic radicals selected from alicyclic, aliphatic and aromatic groups of which at least one is preferably substituted with at least one electronegative moiety and the methylene groups are present at the trans-2,3 positions on the norbornane moiety. The invention also provides a novel method for producing the bidentate ligand and novel intermediate phosphine oxide and phosphinous acid compounds.
    Type: Grant
    Filed: April 10, 1996
    Date of Patent: January 20, 1998
    Assignee: Hoechst Celanese Corporation
    Inventors: Jerry D. Unruh, Brigitte E. Segmuller, Gabriel R. Chapa, Kent E. Pryor
  • Patent number: 5698743
    Abstract: Preparation of methylene-bridged compounds of the formula I ##STR1## where R.sup.1 to R.sup.4 are identical or different and are each saturated C.sub.1 -C.sub.30 -hydrocarbyl, unsubstituted phenyl, phenyl substituted by substituents inert under the reaction conditions, or hydrogen, E.sup.1 and E.sup.2 are identical or different and are each phosphorus, arsenic or antimony, and X is a chemical bond or oxygen by reacting a tin compound of the general formula IIR.sub.3.sup.5 Sn--CH.sub.2 M, IIwhere R.sup.5 is C.sub.1 --C.sub.20 -hydrocarbyl and M is an alkali metal, with a compound of the general formula III ##STR2## where Y is halogen, metallating the thus-obtained tin compound of the general formula IV ##STR3## with an alkali organometallic, and reacting the product with a compound of the general formula V ##STR4## to give a methylene-bridged compound of the formula I. And novel bis(diorganophosphino)methanes.
    Type: Grant
    Filed: November 26, 1996
    Date of Patent: December 16, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Arthur Hohn, Justin Wolf
  • Patent number: 5696296
    Abstract: A diphosphine of the formula (I) ##STR1## in which Ar--Ar is a biphenyl radical, a 1-phenyl-naphthyl radical or a 1,1'-binaphthyl radical, the CH.sub.2 groups am each located in the ortho-position relative to the Ar--Ar bond, R is F or an alkyl radical or alkoxy radical having in each case 1 to 8 carbon atoms, n is an integer from 0 to 4, the radicals PR.sup.1 R.sup.2 and PR.sup.3 R.sup.4 differ from one another, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 independently of one another are each an alkyl radical having 1 to 10 carbon atoms, a cycloaliphatic radical having 5 to 10 carbon atoms, or a radical Ar.sup.1 --(R.sup.5).sub.m, in which AR.sup.1 is a phenyl radical, R.sup.5 is F, CF.sub.3, or an alkyl radical having 1 to 4 carbon atoms and m is 0 to 1, or R.sup.1, R.sup.2, R.sup.3 and R.sup.
    Type: Grant
    Filed: September 27, 1995
    Date of Patent: December 9, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Christoph Naumann, Dieter Regnat
  • Patent number: 5693868
    Abstract: The present invention provides a method for producing novel optically active diphosphine compounds ?2,2'-bis(di-substituted phosphino)-1,1'-binaphthyl compounds! having a selectivity (chemoselectivity or enantioselectivity) and catalytic activity different from those of conventional BINAP compounds. In a method of the present invention for producing an optically active diphosphine compound (i.e., 2,2-bis(di-substituted phosphino)-1,1'-binaphthyl), 2,2'-bis(trifluoromethanesulfonyloxy)-1,1'-binaphthyl is reacted, in the presence of a transition metal-phosphine complex, with a phosphineoxide compound represented by the following general formula:A.sub.
    Type: Grant
    Filed: October 30, 1996
    Date of Patent: December 2, 1997
    Assignee: Takasago International Corporation
    Inventors: Noboru Sayo, Xiaoyong Zhang, Tatsuya Ohmoto, Akifumi Yoshida, Tohru Yokozawa
  • Patent number: 5693627
    Abstract: A method of inhibiting the proliferation of B cells by using inhibitors of phosphotyrosine phosphatase can be used to regulate the immune response and to treat diseases such as leukemias or lymphomas marked by malignant proliferation of B cells. The use of such inhibitors can be combined with radiation, which produces a synergistic effect. Several types of inhibitors can be used, including: (1) compounds comprising a metal coordinate-covalently bound to an organic moiety that can form a five- or six-membered ring; (2) compounds in which vanadium (IV) is coordinate-covalently bound to an organic moiety such as a hydroxamate, .alpha.-hydroxypyridinone, .alpha.-hydroxypyrone, .alpha.-amino acid, hydroxycarbonyl, or thiohydroxamate; (3) coordinate-covalent complexes of vanadyl and cysteine or a derivative thereof; (4) nonhydrolyzable phosphotyrosine phosphatase analogues; (5) phostatin; and (6) 4-(fluoromethyl)phenyl phosphate and esterified derivatives.
    Type: Grant
    Filed: May 25, 1995
    Date of Patent: December 2, 1997
    Assignee: Bristol-Myers Squibb Company
    Inventor: Gary L. Schieven
  • Patent number: 5693807
    Abstract: The invention relates to substituted hydroquinone derivatives of the general formula I ##STR1## wherein R.sub.4 is lower alkyl and either R.sub.1 is hydroxy, halogen, a group of the formula --P(=O)(R.sub.5)R.sub.6 (Ia), a group of the formula --P.sup.+ (R.sub.7)(R.sub.8)R.sub.9 X.sup.- (Ib) or a group of the formula --Si(R.sub.7)(R.sub.8)R.sub.9 (Ic), M is methylene, R.sub.2 is hydrogen or a group of the formula ##STR2## and R.sub.3 is hydrogen or halogen, or .sub.1 is hydroxy or lower alkoxy, M is carbonyl, R.sub.2 is hydrogen and R.sub.3 is halogen, each of R.sub.5 and R.sub.6, independently of the other, is lower alkyl, lower alkoxy Or N,N-di-lower alkylamino, or is benzyl, benzyloxy, phenyl or phenoxy, each of which is unsubstituted or mono- or di-substituted at the phenyl ring, to a process for the preparation of those compounds and to the use of those compounds, and to a process in which those compounds are used.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: December 2, 1997
    Assignee: Ciba-Geigy Corporation
    Inventors: Gottfried Sedelmeier, Gerhard Fischer
  • Patent number: 5689005
    Abstract: A process for the deoxygenation of organic oxo compounds, in particular phosphine oxides to phosphines and nitrobenzene to aniline, with reduced redox catalysts in a non-steady-state reaction with decoupled reductive regeneration of the redox catalyst entails the redox catalyst being reduced to a lower oxidation state and being reused for the deoxygenation.
    Type: Grant
    Filed: November 28, 1995
    Date of Patent: November 18, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Alfred Hagemeyer, Christopher William Rieker, Thomas Lautensack, Dieter Hermeling
  • Patent number: 5679863
    Abstract: The preparation of .alpha.-carbonylphosphine oxides by oxidizing an .alpha.-hydroxyalkyl phosphine oxide with an organic hydroperoxide or of an organic peroxy acid in the presence of a compound of a Group IV to Group VIII metal in the periodic table, and novel .alpha.-hydroxybenzyl phosphine oxides. .alpha.-Carbonylphosphine oxides are used as photoinitiators for polymerizable compositions.
    Type: Grant
    Filed: October 16, 1995
    Date of Patent: October 21, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Martin Fischer, Eckhard Hickmann, Rudolf Kropp, Jochen Schroeder, Beate Trentmann
  • Patent number: 5654485
    Abstract: By reacting certain partially sterically-hindered chloro-substituted cycloalkanes with sodium and/or potassium diarylphosphides in an ether reaction medium, not only are useful cycloalkyldiarylphosphines produced, but in addition the chloro-substituted cycloalkane does not undergo any appreciable reaction with the coproduced aryl sodium and/or aryl potassium as it is formed. Moreover, the process makes it possible to avoid or at least to greatly reduce interaction with or cleavage of cyclic ether reaction media such as tetrahydrofuran. Thus the process makes possible improvements both in yield and quality of the cycloalkyldiarylphosphite product. A two-stage process conducted in an ether reaction medium is also described. In the first stage the sodium and/or potassium diarylphosphine reactant is produced by reaction between sodium and/or potassium and triarylphosphine.
    Type: Grant
    Filed: March 25, 1996
    Date of Patent: August 5, 1997
    Assignee: Albemarle Corporation
    Inventors: K. Pushpananda A. Senaratne, Arcelio J. Malcolm, Felix M. Orihuela, Hassan Y. Elnagar
  • Patent number: 5654486
    Abstract: Partially sterically-hindered cycloalkyl chlorides are reacted with lithium diarylphosphides in inert liquid hydrocarbon reaction media to form cycloalkyldiarylphosphines. Aryl lithium is coproduced. The process makes it possible to avoid, or at least substantially eliminate, the interaction with or cleavage of cyclic ether reaction media such as tetrahydrofuran, previously the solvent of choice for conducting this type of reaction. Also during the conduct of the present process the chloro-substituted cycloalkane does not undergo any appreciable reaction with the coproduced aryl lithium as it is formed. Thus improvements both in yield and quality of the cycloalkyldiarylphosphine product are made possible. A comprehensive three-step process for converting triarylphosphine to cycloalkyldiarylphosphine is also described.
    Type: Grant
    Filed: March 25, 1996
    Date of Patent: August 5, 1997
    Assignee: Albemarle Corporation
    Inventors: K. Pushpananda A. Senaratne, Arcelio J. Malcolm, Felix M. Orihuela, Hassan Y. Elnagar
  • Patent number: 5650099
    Abstract: A dicationic surfactant for enhancing the chemiluminescence of chemiluminescent compounds particularly dioxetanes which are triggerable is described. The surfactant has the formulaX.sup.- (R.sub.1).sub.3 A.sup.+ CH.sub.2 -Link-CH.sub.2 A.sup.+ (R.sub.2).sub.3 X.sup.-wherein A is selected from the group consisting of phosphorus and nitrogen atoms separately or together, wherein X is an anionic counterion and R.sub.1 and R.sub.2 are selected from the group consisting of unsubstituted and substituted alkyl and aralkyl groups containing 1 to 20 carbon atoms and R.sub.1 and R.sub.2 can be the same or different, and wherein Link is a carbon chain group selected from the group consisting of dialkylenearyl, aryl, alkylene, alkenylene and alkynylene groups containing 4 to 20 carbon atoms. The surfactants are particularly useful in Western and Southern blot assays.
    Type: Grant
    Filed: May 16, 1995
    Date of Patent: July 22, 1997
    Assignee: Lumigen, Inc.
    Inventors: M. Hashem Akhavan-Tafti, Zahra Arghavani
  • Patent number: 5648548
    Abstract: An optically active 2-diphenylphosphinomethyl-2'-diphenylphosphinyl-1,1'-binaphthalene derivative represented by the following general formula (I) ##STR1## wherein R represents a phenyl group, a tolyl group, an anisyl group or a chlorophenyl group, and a process for the production of optically active substances in which the above compound and a transition metal compound are used. The asymmetric diphosphine of the present invention is related to the creation of novel compounds, which is excellent as a ligand for asymmetric synthesis use. When the above compound is used together with a transition metal compound such as of ruthenium, rhodium or the like, it shows markedly excellent properties as the catalyst of asymmetric hydrogenation and the like reactions, in terms of selectivity, conversion ratio, catalytic activity and the like.
    Type: Grant
    Filed: March 13, 1996
    Date of Patent: July 15, 1997
    Assignee: Takasago International Corporation
    Inventors: Hidemasa Takaya, deceased, Tetsuo Ota, Koji Inagaki
  • Patent number: 5648549
    Abstract: The invention relates to a process for the preparation of secondary phosphines of the formula (I) ##STR1## in which R.sup.1 to R.sup.6 independently of one another are hydrogen, halogen, (C.sub.1 -C.sub.6)-alkyl or (C.sub.1 -C.sub.6)-alkoxy, wherein secondary phosphine oxides of the formula (II) ##STR2## are reacted with Lewis acids as catalysts, at elevated temperature, and the secondary phosphines of the formula (I) formed are distilled off under reduced pressure.
    Type: Grant
    Filed: July 15, 1996
    Date of Patent: July 15, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Hans-Jerg Kleiner
  • Patent number: 5635158
    Abstract: The peptides described are modified with the phosphine group and are useful for marking with .sup.99m Tc and .sup.186-188 Re or paramagnetic agents for use in diagnosis and radiotherapy; in particular chelating compounds having the co-ordinating sets PN.sub.2 X, where X is --S, --O, COO--, PN.sub.3, P.sub.2 N.sub.3 and P.sub.2 N.sub.2 are described.
    Type: Grant
    Filed: June 23, 1995
    Date of Patent: June 3, 1997
    Assignee: Sorin Radiofarmaci SRL
    Inventors: Ulderico Mazzi, Fabio Lunghi
  • Patent number: 5627174
    Abstract: Fluorinated alkene compounds useful for and methods of controlling nematodes, insects, and acarids that prey on agricultural crops, these compounds having the general structure: ##STR1## These Polar compounds are particularly useful for systemic control of pests.
    Type: Grant
    Filed: May 23, 1995
    Date of Patent: May 6, 1997
    Assignee: Monsanto Company
    Inventors: Dennis P. Phillion, Peter G. Ruminski, Gopichand Yalamanchili
  • Patent number: 5621128
    Abstract: 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: Grant
    Filed: June 28, 1995
    Date of Patent: April 15, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Joachim-Heiner Jendralla
  • Patent number: 5621129
    Abstract: 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: Grant
    Filed: March 7, 1996
    Date of Patent: April 15, 1997
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Tamio Hayashi, Masayoshi Minai, Kazunori Iwakura
  • Patent number: 5600006
    Abstract: The invention relates to novel 2,2'-bis [bis(aryl)phosphinomethyl]-1,1'-binaphthyls of the formula ##STR1## in which Ar.sup.2 is a phenyl radical, R' is an alkyl radical having 1 to 4 carbon atoms, CF.sub.3, fluorine, chlorine or bromine, and n is 1 or 2.
    Type: Grant
    Filed: November 10, 1994
    Date of Patent: February 4, 1997
    Assignee: Hoechst A.G.
    Inventors: Dieter Regnat, Hans-Jerg Kleiner
  • Patent number: 5580991
    Abstract: The disclosure describes a method for separating a ruthenium complex, which comprises removing an objective hydrogenation reaction product from a hydrogenation reaction solution of an organic carbonyl compound in the presence of a ruthenium complex having a tertiary organic phosphorus compound as ligand to obtain a catalyst solution, contacting said catalyst solution with a polar solvent, and carrying out a phase-separation into a liquid phase substantially composed of the polar solvent and an another liquid phase substantially containing the ruthenium complex.
    Type: Grant
    Filed: April 4, 1995
    Date of Patent: December 3, 1996
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Hitoshi Sugiyama, Kazunari Takahashi, Haruhiko Kusaka
  • Patent number: 5569800
    Abstract: An electrophotographic photoconductor which is composed of an electroconductive support and a photoconductive layer formed thereon comprising a novel pyrene-ring-containing olefin compound having formula [I]: ##STR1## wherein R.sup.1 and R.sup.2 each represent hydrogen or an alkyl group which may have a substituent; Y is an aliphatic hydrocarbon group which may have a substituent, a cyclic hydrocarbon group which may have a substituent, or an aromatic group which may have a substituent; n is an integer of 0 or 1, and m is an integer of 1 to 3, provided that when n is 0, m is 1, R.sup.1 is hydrogen, and Y is an aromatic group with a substituent ##STR2## R.sup.2 and R.sup.3 each represent hydrogen, and Y and R.sup.1 may be bonded to form a ring, a method of synthesizing the pyrene-ring-containing olefin compound and an intermediate therefor are disclosed.
    Type: Grant
    Filed: May 2, 1995
    Date of Patent: October 29, 1996
    Assignee: Ricoh Company, Ltd.
    Inventors: Tamotsu Aruga, Masaomi Sasaki, Tomoyuki Shimada, Hiroshi Adachi
  • Patent number: 5556998
    Abstract: 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: Grant
    Filed: March 13, 1995
    Date of Patent: September 17, 1996
    Assignee: Takasago International Corporation
    Inventors: Akira Miyashita, Takeshi Chiba, Hiroyuki Nohira, Hidemasa Takaya
  • Patent number: 5554795
    Abstract: 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: Grant
    Filed: May 19, 1995
    Date of Patent: September 10, 1996
    Assignee: Phillips Petroleum Company
    Inventors: Krisztina Frey, Gabriele von Massow, Helmut G. Alt, M. Bruce Welch
  • Patent number: 5550295
    Abstract: Arylalkyl phosphines, phosphine oxides or phosphine sulfides are prepared by reacting an alkyl phosphine, phosphine oxide or phosphine sulfide with an arylhalide in the presence of a zero valence palladium catalyst.
    Type: Grant
    Filed: May 3, 1995
    Date of Patent: August 27, 1996
    Assignee: Cytec Technology Corp.
    Inventor: John H. Hillhouse
  • Patent number: 5530150
    Abstract: 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: Grant
    Filed: October 12, 1994
    Date of Patent: June 25, 1996
    Assignee: Takasago International Corporation
    Inventors: Hidemasa Takaya, Nozomu Sakai, Kyoko Tamao, Satoshi Mano, Hidenori Kumobayashi, Tetsuo Tomita, Takao Saito, Kazuhiko Matsumura, Yasushi Kato, Noboru Sayo
  • Patent number: 5527966
    Abstract: Triphenylphosphine (TPP) is prepared by reacting triphenylphosphine dichloride (TPPCl.sub.2) with magnesium, aluminum and/or iron in the presence of an inert solvent, employing a TPPCl.sub.2 solution whose content of phosgene, chlorine, diphosgene, hydrogen chloride, thionyl chloride, sulfuryl chloride, phosphorus trichloride, phosphorus oxychloride and/or aliphatic halogen compounds (active chlorine compounds) totals less than 1000 ppm Cl.
    Type: Grant
    Filed: August 3, 1994
    Date of Patent: June 18, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Dieter Hermeling, Peter Bassler, Peter Hammes, Randolf Hugo, Peter Lechtken, Hardo Siegel
  • Patent number: 5527967
    Abstract: The invention relates to a process for preparing phosphines ##STR1## where, for example R.sup.1 is (C.sub.1 -C.sub.10)alkyl, (C.sub.3 -C.sub.10)cycloalkyl, C(YZ)aryl Y, Z is (C.sub.1 -C.sub.4)alkyl, hydrogen, Aryl is phenyl, naphthyl, anthracenyl, phenanthrenyl, or biphenyl, binaphthylandR.sup.2, R.sup.3 are, independently of one another, phenyl, naphthyl or anthracenyl,by reacting a diarylphosphine ##STR2## where X is bromine, chlorine, fluorine, (C.sub.1 -C.sub.4)alkoxy, O-phenyl, with a reducing agent and a quaternary ammonium compound ##STR3## where A is an anion of an organic or inorganic acid.
    Type: Grant
    Filed: May 24, 1995
    Date of Patent: June 18, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Hans Millauer
  • Patent number: 5525580
    Abstract: Compounds represented by general formula (I), herbicides or selective herbicides for paddy field containing said compounds as active ingredients, method of controlling growth of undesirable plants by applying the herbicides on places where control is desired. ##STR1## wherein A represents a --S(O)nR.sup.1 in which n is 0 or 2 and R.sup.1 represents a (substituted) lower alkyl; a cycloalkyl; a (substituted) benzyl; a (substituted) phenyl; or a --OR.sup.2 in which R.sup.2 represents a (substituted) phenyl;B represents a halogen, a nitro, a lower alkyl, or a lower alkylsulfonyl;D represents a hydrogen, a lower alkyl, a lower alkoxy, a lower alkoxymethyl, or a lower alkoxycarbonyl;E represents a halogen, a (substituted) lower alkoxy, a lower alkylthio, a (substituted) lower alkylsulfonyl, or a lower alkylsulfonyloxy.The herbicides of the present invention can prevent a wide variety of noxious weeds and further selectively prevent weeds on paddy field with considerably reduced phytotoxicities on rice plant.
    Type: Grant
    Filed: January 14, 1994
    Date of Patent: June 11, 1996
    Assignee: SDS Biotech K.K.
    Inventors: Kenichi Komatsubara, Tadashi Sato, Kenji Mikami, Yuji Yamada
  • Patent number: 5523437
    Abstract: 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: Grant
    Filed: July 26, 1994
    Date of Patent: June 4, 1996
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Tamio Hayashi, Yasuhiro Uozumi, Kazunori Iwakura, Isao Kurimoto, Masayoshi Minai
  • Patent number: 5516944
    Abstract: The present invention is concerned with novel optically active phosphorus compounds of the general formula ##STR1## wherein R and R.sup.1 each independently signify hydroxy, a protected hydroxy group, lower alkyl or lower alkoxy andR.sup.2 to R.sup.5 each independently signify alkyl with 3 to 7 carbon atoms, cycloalkyl or aryl or R.sup.2 and R.sup.3 or R.sup.4 and R.sup.5 together with the phosphorus form a group of the formula ##STR2## wherein R2 and R3 are different when R4 and R5 are the same, and R4 and R5 are different when R2 and R3 are the same,the manufacture of such compounds, their use for enantioselective reactions, such as, e.g., asymmetric hydrogenations, enantioselective hydrogen displacements in prochiral allylic systems and the like, as well as complexes of the compounds of formula I with Group VIII metals.
    Type: Grant
    Filed: September 30, 1994
    Date of Patent: May 14, 1996
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Emil A. Broger, Marco Cereghetti, Alain Rageot
  • Patent number: 5510503
    Abstract: 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: Grant
    Filed: September 2, 1994
    Date of Patent: April 23, 1996
    Assignee: Bayer Aktiengesellschaft
    Inventors: Christian Laue, Georg Schroder, Dieter Arlt, Rolf Grosser
  • Patent number: 5508438
    Abstract: Novel, racemic and optically active phosphorus compounds of the formula ##STR1## wherein R signifies lower alkyl, lower alkoxy, hydroxy or a protected hydroxy group, R.sup.1 and R.sup.2 are different from each other and represent lower alkyl, cycloalkyl, aryl, a five-membered heteroaromatic or a group of the formula ##STR2## are described. The compounds of formula I are useful in the form of complexes with a metal of Group VIII as catalysts for asymmetric hydrogenations and for enantioselective hydrogen displacements in prochiral allylic systems.
    Type: Grant
    Filed: September 24, 1993
    Date of Patent: April 16, 1996
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Emil A. Broger, Marco Cereghetti
  • Patent number: 5502083
    Abstract: The composition of the present invention is excellent in compatibility, transparency and curability and give a cured coat of excellent gloss and of less smell, and cured products of excellent properties can be obtained by curing the composition.The present invention relates to an onium salt represented by the following formula (1): ##STR1## wherein Ar is a mono- to tetra-valent aromatic group, X is a bisphenylsulfonio group which may have a substituent, a is 1-4, b is 0 or 1-3, a+b is 1-4, n is 1-4, and Z is a halide represented by the following formula (3):MQ.sub.m (OH).sub.l (3)where M is a boron atom, a phosphorus atom, an arsenic atom or an antimony atom, Q is a halogen atom, m is 3-6, l is 0 or 1, and m+l is 4-6; a photopolymerization initiator containing the onium salt as an active ingredient; an energy ray-curable composition containing the initiator; and a cured product.
    Type: Grant
    Filed: June 8, 1994
    Date of Patent: March 26, 1996
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Tetsuya Abe, Kazuhiko Ishii, Minoru Yokoshima
  • Patent number: 5481041
    Abstract: A process for isolating triphenylphosphine (TPP) from a triphenylphosphine/aluminum chloride complex dissolved in chlorobenzene by decomplexation, hydrolysis and extraction using water and subsequent separation of the liquid/liquid dispersion, which is composed of a TPP-containing chlorobenzene phase and of an containing Al and Cl compounds aqueous phase, into a TPP-containing chlorobenzene phase and into a TPP-free, aqueous phase, containing Al and Cl compounds, whereinwater is dispersed in the chlorobenzene phase in a ratio of 0.6-0.95 kg of water per kg of chlorobenzene solution in a 1st mixing apparatus in such a way that the temperature resulting from the hydrolysis is in the range from 60.degree. to 90.degree. C., the dispersion being carried out with residence times of 5-30 minutes and energy densities of 2-10 kW/m.sup.3,a second dispersion is carried out in a 2nd mixing apparatus with residence times of 5-60 minutes and energy densities of 0.05-0.5 kW/m.sup.
    Type: Grant
    Filed: August 3, 1994
    Date of Patent: January 2, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Lechtken, Friedrich Sauer, Matthias Fankhaenel, Dieter Hermeling
  • Patent number: 5468890
    Abstract: The invention concerns iodonium salts of the general formula A-I.sup.+ --B X.sup.-, in which A is a group of the general formula ##STR1## in which C is a monovalent aromatic hydrocarbon group with 6 to 14 carbon atoms or a monovalent aromatic hydrocarbon group containing at least one oxygen and/or sulphur atom and with 5 to 14 atoms in the aromatic ring, D, E and F are each substituents of C, D being a group of the formula --(O).sub.x --(R).sub.y --SiR1/3, E being a group of the formula --OR.sup.2, F being a group of the formula --R.sup.3, a being 1, 2, or 3, b being 0, 1 or 2, c being 0, 1 or 2, x being 0 or 1 and y being 0 or 1, and R, R.sup.1, R.sup.2 and R.sup.3 are as defined in claim 1; B is a group of the formula ##STR2## in which E and F, which are as defined above, may each be bound to the 2, 3, 4, 5 or 6 position in the benzene ring, d is 0, 1 or 2, e is 0, 1 or 2 and X.sup.- is a tosylate anion or a weakly nucleophilic or non-nucleophilic anion Y.sup.- selected from the group comprising CF.sub.
    Type: Grant
    Filed: June 8, 1994
    Date of Patent: November 21, 1995
    Assignee: Wacker-Chemie GmbH
    Inventors: Christian Herzig, Silke Scheiding
  • Patent number: 5457219
    Abstract: Novel, racemic and optically active phosphorus compounds of the formula ##STR1## wherein R signifies lower alkyl or lower alkoxy and R.sup.1 represents lower alkyl, cycloalkyl or substituted phenyl, are described.The compounds of formula I are useful in the form of complexes with a metal of Group VIII as catalysts for asymmetric hydrogenations and for enantioselective hydrogen displacements in prochiral allylic systems.
    Type: Grant
    Filed: September 27, 1993
    Date of Patent: October 10, 1995
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Joseph Foricher, Rudolf Schmid
  • Patent number: 5414134
    Abstract: Bisphosphine oxide monomers and homologs thereof may be incorporated into polycarbonates in order to obtain a flame retardant polymer. More particularly, bis[2,5-(diphenylphosphine oxide)]-1,4-hydroquinone and homologs thereof may be used to prepare flame retardant polycarbonates that retain high glass transition temperature and high impact resistances.
    Type: Grant
    Filed: December 20, 1993
    Date of Patent: May 9, 1995
    Assignee: General Electric Company
    Inventor: Gary C. Davis
  • Patent number: 5399771
    Abstract: A process of synthesizing a compound of the formula 1: ##STR1## is disclosed, which comprises reacting a compound of the formula 2: ##STR2## with diphenylphosphine in the presence of an amine base and a nickel catalyst to produce a compound of formula 1.
    Type: Grant
    Filed: June 1, 1994
    Date of Patent: March 21, 1995
    Assignee: Merck & Co., Inc.
    Inventors: Dongwei Cai, Joseph F. Payack, Thomas R. Verhoeven
  • Patent number: 5354894
    Abstract: Disclosed is a process for the preparation of alkali metal diarylphosphide compounds wherein at least one of the aryl radicals is substituted with an alkyl group. Also disclosed is the preparation of alkyl(diaryl)phosphine compounds which are obtained by the reaction of the alkali metal diarylphosphide compounds with alkyl halide alkylating agents.
    Type: Grant
    Filed: October 14, 1993
    Date of Patent: October 11, 1994
    Assignee: Eastman Chemical Company
    Inventor: Thomas J. Devon
  • Patent number: 5352813
    Abstract: 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: Grant
    Filed: September 3, 1991
    Date of Patent: October 4, 1994
    Assignee: University of Alberta
    Inventors: Ronald G. Cavell, Kattesh V. Katti
  • Patent number: 5352822
    Abstract: The present invention discloses pesticidally active compounds of formula (II) ##STR1## or a salt thereof, wherein Q is an monocyclic aromatic ring, or fused bicyclic ring system of which at least one ring is aromatic containing 9 or 10 atoms of which one may be nitrogen and the rest carbon each ring system being optionally substituted, or Q is a dihalovinyl group or a group R.sup.6 --C.tbd.C-- where R.sup.6 is C.sub.1-4 alkyl, tri C.sub.1-4 alkylsilyl, halogen or hydrogen; R.sup.2, R.sup.3 , R.sup.4 and R.sup.5 are the same or different with at least one being hydrogen and the others being independently selected from hydrogen, halo, C.sub.1-4 alkyl or C.sub.1-4 haloalkyl; and R.sup.1 is selected from hydrogen and C.sub.1-8 hydrocarbyl optionally substituted by dioxalanyl, halo, cyano, trifluoromethyl, trifluoromethylthio or C.sub.1-6 alkoxy and X.sup.1 is hydrogen, fluoro or chloro.
    Type: Grant
    Filed: April 7, 1993
    Date of Patent: October 4, 1994
    Assignee: Roussel Uclaf
    Inventors: Robert J. Blade, George S. Cockerill, John E. Robinson
  • Patent number: 5312939
    Abstract: 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: Grant
    Filed: July 10, 1991
    Date of Patent: May 17, 1994
    Assignee: Takasago International Corporation
    Inventors: Yoji Hori, Hidenori Kumobayashi
  • Patent number: 5306835
    Abstract: A method for producing octadienols, which comprises reacting 1,3-butadiene with water in the presence of a palladium compound, a phosphine compound and carbon dioxide, wherein a compound of the formula (I): ##STR1## wherein each of R.sup.1, R.sup.5 and R.sup.9 which may be the same or different, is a hydrocarbon group, and each of R.sup.2, R.sup.3, R.sup.4, R.sup.6, R.sup.7, R.sup.8, R.sup.10, R.sup.11 and R.sup.12 which may be the same or different, is hydrogen or a substituent, provided that at least one of them is an electron donative substituent, is used as the phosphine compound.
    Type: Grant
    Filed: September 3, 1993
    Date of Patent: April 26, 1994
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Keiichi Sato, Iwao Nakajima, Yoko Misu
  • Patent number: 5300686
    Abstract: Organophosphorus dihalides can have one of their halogen substituents substituted with an alkyl group from a trialkylaluminum by gradual addition of the latter reagent to the former.
    Type: Grant
    Filed: January 19, 1990
    Date of Patent: April 5, 1994
    Assignee: Akzo nv
    Inventor: Jeffrey E. Telschow