Halogen Containing Patents (Class 568/16)
  • Patent number: 6841304
    Abstract: The invention concerns novel ionic compounds with low melting point whereof the onium type cation having at least a heteroatom such as N, O, S or P bearing the positive charge and whereof the anion includes, wholly or partially, at least an ion imidide such as (FX1O)N?(OX2F) wherein X1 and X2 are identical or different and comprise SO or PF, and their use as solvent in electrochemical devices. Said composition comprises a salt wherein the anionic charge is delocalised, and can be used, inter alia, as electrolyte.
    Type: Grant
    Filed: November 9, 2001
    Date of Patent: January 11, 2005
    Assignees: ACEP, Inc., Centre National de la Recherche Scientifique, Universite de Montreal
    Inventors: Christophe Michot, Michel Armand, Michel Gauthier, Nathalie Ravet
  • Patent number: 6841301
    Abstract: The present invention relates to fluoroalkyl phosphates, to a process for the preparation, and to their use as conductive salts in batteries, capacitors, supercapacitors and galvanic cells.
    Type: Grant
    Filed: August 1, 2001
    Date of Patent: January 11, 2005
    Assignee: Merck Patent GmbH
    Inventors: Udo Heider, Michael Schmidt, Andreas Kühner, Peter Sartori, Nikolai Ignatyev
  • Publication number: 20040191635
    Abstract: A non-aqueous electrolyte cell comprises a positive electrode, a negative electrode and a non-aqueous electrolyte containing a support salt. The non-aqueous electrolyte further comprises a phosphazene derivative. The phosphazene derivative having a specified structure functions as an electrode stabilizing agent or a non-combustion agent.
    Type: Application
    Filed: January 5, 2004
    Publication date: September 30, 2004
    Inventors: Masashi Otsuki, Shigeki Endo, Takao Ogino, Yasuo Horikawa
  • Publication number: 20040110631
    Abstract: Zwitterionic compositions of matter comprising cations [Ct]+ and anions connected together with substantially rigid fluorinated linking groups are described. These zwitterionic compositions serve as cocatalysts. They activate olefin polymerization catalysts, and can dissolve in aliphatic solvents. Synthesis and polymerization are illustrated.
    Type: Application
    Filed: April 24, 2003
    Publication date: June 10, 2004
    Inventor: George Rodriguez
  • Patent number: 6727390
    Abstract: A method of increasing the fluorous nature of a compound includes the step of reacting the compound with or tagging the compound with at least one of a second compound having the formula: wherein R is an alkyl group or an aryl group, n is 1, 2 or 3 and Rs is a spacer group and Rf is a branched fluorous group. A chemical compound having the general formula: wherein n, Rs and Rf are defined above.
    Type: Grant
    Filed: September 14, 2001
    Date of Patent: April 27, 2004
    Assignee: University of Pittsburgh
    Inventors: Dennis P. Curran, Qisheng Zhang
  • Publication number: 20030199704
    Abstract: Disclosed are methods of preparing monoalkyl Group VA metal dihalide compounds in high yield and high purity by the reaction of a Group VA metal trihalide with an organo lithium reagent or a compound of the formula RnM1X3-n where R is an alkyl, M1 is a Group IIIA metal, X is a halogen and n is an integer fro 1 to 3. Such monoalkyl Group VA metal dihalide compounds are substantially free of oxygenated impurities, ethereal solvents and metallic impurities.
    Type: Application
    Filed: November 23, 2002
    Publication date: October 23, 2003
    Applicant: Shipley Company, L.L.C.
    Inventors: Deodatta Vinayak Shenai-Khatkhate, Michael Brendan Power, Artashes Amamchyan
  • Publication number: 20030170548
    Abstract: The present invention provides an additive for a non-aqueous electrolyte comprising a phosphazene derivative represented by the following formula (1):
    Type: Application
    Filed: May 5, 2003
    Publication date: September 11, 2003
    Inventors: Masashi Otsuki, Shigeki Endo, Takao Ogino
  • Patent number: 6605736
    Abstract: A condensed phosphoric ester having a very low content of volatile components is provided by a process including a first step of reacting a phosphorus oxytrihalide with a bisphenol-based compound to prepare a phosphorohalidate; a second step of removing unreacted phosphorus oxytrihalide; and a third step of reacting the phosphorohalidate with a monophenol-based compound at a specific ratio.
    Type: Grant
    Filed: April 15, 2002
    Date of Patent: August 12, 2003
    Assignee: Daihachi Chemical Industry Co., Inc.
    Inventors: Shin Nakamura, Kazuo Noguchi, Taku Fujisawa, Takafumi Ohkawa
  • Patent number: 6590100
    Abstract: The present invention provides a process for preparing a polyaromatic compound comprising at least one sequence of two aromatic rings. The process of the invention, which consists in reacting an aromatic compound bearing a leaving group and an arylboronic acid and/or its derivatives in the presence of a base and an effective amount of a nickel catalyst, is characterized in that the reaction is conducted in a reaction solvent which is water optionally in a mixture with an organic solvent and in the presence of an effective amount of a catalyst based on nickel with at least one water-soluble phosphine ligand.
    Type: Grant
    Filed: May 15, 2002
    Date of Patent: July 8, 2003
    Assignee: Rhodia Chimie
    Inventors: Jean-Christophe Galland, Monique Savignac, Jean-Pierre Genet
  • Patent number: 6590125
    Abstract: A light-emitting polymer and its preparation method, the polymer being excellent in electron injection and transport ability as well as hole injection and transport ability in an EL device, the EL device manufactured from the polymer being also emittable in the blue emission region, in which the EL device from an inorganic material is not mostly emittable. The light-emitting polymer of the invention is an alternated copolymer having repeated units (arylenevinylene units) excellent in hole injection and transport ability and repeated units (fluorinated tetraphenyl units) excellent in electron injection and transport ability with alternated order, as shown in formula (II). An EL device manufactured from the light-emitting polymer, a fluorinated tetraphenyl derivative of formula (I), which is used as a monomer to prepare the light-emitting polymer, and their preparation methods.
    Type: Grant
    Filed: April 3, 2001
    Date of Patent: July 8, 2003
    Assignee: Electronics and Telecommunications Research Institute
    Inventors: Do Hoon Hwang, Tae Hyoung Zyung, Lee Mi Do, Hye Yong Chu
  • Patent number: 6548708
    Abstract: This invention relates to processes for making phosphorus compounds R2P—X—PR2, R2P—M, R2P—L and R3P, and the novel cation R2P+(L)—X—P+(L)R2, where R represents an optionally substituted hydrocarbyl group, X represents a bridging group, L represents a leaving group and M represents an alkali metal atom. The invention relates further to a process for making a compound R2P—L from a compound R—H via a new process for making the compound R—Li followed by its reaction with a compound Hal2P—L. The compound R2P—X—PR2 is a ligand suitable for making catalysts for copolymerizing carbon monoxide and a olefinically unsaturated compound.
    Type: Grant
    Filed: February 2, 2001
    Date of Patent: April 15, 2003
    Assignee: SRI International
    Inventors: Roelof Van Ginkel, Alexander Van Der Made, Jan De With, Wolf Eilenberg
  • Patent number: 6538115
    Abstract: The present invention relates to novel complexes of (transition) metals containing ligands having phosphorus centers supporting a carbene atom or heteroalkane radical bonded to the (transition) metal.
    Type: Grant
    Filed: January 26, 2001
    Date of Patent: March 25, 2003
    Assignee: The Governors of the University of Alberta
    Inventors: Ronald G. Cavell, Ruppa P. Kamalesh Babu, Aparna Kasani
  • Patent number: 6534684
    Abstract: A method for preparing tris[(1H,1H,2H,2H-perfluoroalkyl)aryl]phosphites consists in preparing a grignard reagent from an alkoxyhalogenobenzene, then reacting it with a iodo-1H,1H,2H,2H-perfluoroalkane; transforming the alkoxy function of (1H,1H,2H,2H,2H-perfluoroalkyl)alkoxybenzene obtained into a hydroxy function, then reacting (1H,1H,2H,2H-perfluoroalkyl)hydroxybenzene with PCl3. The invention also concerns fluorinated arylphosphites and their use as transition metal ligand for making catalysts to be used in two-phase catalysis with fluorinated phase.
    Type: Grant
    Filed: December 7, 2001
    Date of Patent: March 18, 2003
    Assignee: Centre National de la Recherche Scientifique (C.N.R.S.)
    Inventors: Jean-Luc Couturier, Thomas Mathivet, Eric Monflier, Yves Castanet, André Mortreux
  • Patent number: 6509100
    Abstract: The present invention discloses hydrogen bond stabilized surface modifying agents having a fluorinated or semi-fluorinated carbon-containing tail group, an internal moiety capable of intermolecular hydrogen bonding or related acid-base interactions and a head group capable of reacting or interacting with surfaces such as metal, non-metallic, ceramic, other inorganic oxide or organic surfaces. The present invention also discloses cost effective method for making the agents, methods for treating surfaces therewith, the treated surfaces and devices made therefrom.
    Type: Grant
    Filed: August 18, 1999
    Date of Patent: January 21, 2003
    Assignee: The University of Houston System
    Inventors: T. Randall Lee, Michael Graupe
  • Publication number: 20020193619
    Abstract: Diaryliodonium salts are disclosed, as well as a method for preparing them, in which one of the aryl groups bonded to the positively-charged iodine ion contains a methyl substituent, and the other one contains a hydroxyl-substituted alkoxy group. The salts are synthesized from (o, m, or p)- iodotoluene, as opposed to iodobenzene, and therefore do not pose a carcinogenic risk. In addition, the present salts are unexpectedly more soluble in most organic solvents, as well as in nonpolar monomers, than the corresponding benzene catalysts. The salts are useful as cationic photoinitiators, cationic thermal initiators (often combined with a cocatalyst, e.g. copper), and as starting materials in the synthesis of urethane-containing iodonium salts.
    Type: Application
    Filed: June 21, 2002
    Publication date: December 19, 2002
    Applicant: Polyset Company, Inc.
    Inventors: James V. Crivello, Georg Feldmann-Krane, Sascha Oestreich
  • Publication number: 20020122979
    Abstract: Fluoroalkylphosphate salts of Formula I, described herein, are suitable for use, alone or in mixtures with, e.g., other salts, in electrolytes, primary batteries, secondary batteries, capacitors, supercapacitors or galvanic cells.
    Type: Application
    Filed: February 25, 2002
    Publication date: September 5, 2002
    Applicant: Merck Patent GmbH
    Inventors: Michael Schmidt, Andreas Kuh ner, Nikolai Ignatyev, Peter Sartori
  • Patent number: 6437187
    Abstract: Novel chemical compounds have an ionic structure and in combination with an organometallic transition metal compound form a catalyst system which is advantageously used for the polymerization of olefins.
    Type: Grant
    Filed: August 16, 2000
    Date of Patent: August 20, 2002
    Assignee: Targor GmbH
    Inventors: Hans Bohnen, Cornelia Fritze, Frank Kueber
  • Patent number: 6380277
    Abstract: The present invention relates to iodonium salts containing urethane groups of reduced crystallization tendency, to a process for their preparation, and to their use for the radiation curing of cationically curing compositions.
    Type: Grant
    Filed: September 19, 2000
    Date of Patent: April 30, 2002
    Assignee: Goldschmidt AG
    Inventors: Sascha Oestreich, Andreas Weier, Stefanie Volkmer
  • Publication number: 20020015883
    Abstract: An ionic liquid of the formula K+A−, wherein K and A are as defined herein, can be used in such things as electrochemical cells, supercapacitors, hydraulic liquids, solvents, organic syntheses.
    Type: Application
    Filed: May 30, 2001
    Publication date: February 7, 2002
    Applicant: Merck Patent GmbH
    Inventors: Volker Hilarius, Udo Heider, Michael Schmidt
  • Publication number: 20020015884
    Abstract: An ionic liquid of the formula K+A− wherein K+ and A− are as defined herein, are suitable for use in electrochemical cells and capacitors. These ionic liquids can also be used in catalysis, as inert solvents, and as hydraulic liquids.
    Type: Application
    Filed: June 11, 2001
    Publication date: February 7, 2002
    Applicant: Merck Patent GmbH
    Inventors: Michael Schmidt, Udo Heider, Winfried Geissler, Nikolai Ignatyev, Volker Hilarius
  • Patent number: 6331532
    Abstract: The invention provides mitochondrially targeted antioxidant compounds. A compound of the invention comprises a lipophilic cation covalently coupled to an antioxidant moiety. In preferred embodiments, the lipophilic cation is the triphenyl phosphonium cation, and the compound is of the formula P(Ph3)+XR•Z− where X is a linking group, Z is an anion and R is an antioxidant moiety. Also provided are pharmaceutical compositions containing the mitochondrially targeted antioxidant compounds, and methods of therapy or prophylaxis of patients who would benefit from reduced oxidative stress, which comprise the step of administering the compounds of the invention.
    Type: Grant
    Filed: May 25, 2000
    Date of Patent: December 18, 2001
    Assignee: University of Otago
    Inventors: Michael P. Murphy, Robin A. J. Smith
  • Publication number: 20010047114
    Abstract: An efficient process for the production of substituted 10-chloro-phenoxaphosphines or 10 bromo-phenoxaphosphines by reaction of substituted diphenyl ethers with phosphorus trihalogenide in the presence of at least one Lewis acid and subsequent treatment with an amine.
    Type: Application
    Filed: April 30, 2001
    Publication date: November 29, 2001
    Inventors: Jurgen Herwig, Peter Skutta, Stefanie Sturm
  • Patent number: 6306555
    Abstract: Radiation-sensitive compositions comprising (a1) a cationically or acid-catalytically polymerisable or crosslinkable compound or (a2) a compound that increases its solubility in a developer under the action of acid; and (b) at least one diaryliodonium salt of formula I X is branched C3-C20alkyl or C3-C8cycloalkyl; X1 is hydrogen, linear C1-C20alkyl, branched C3-C20alkyl or C3-C8cycloalkyl; with the proviso that the sum of the carbon atoms in X and X1 is at least 4; Y is linear C1-C10alkyl, branched C3-C10alkyl or C3-C8cycloalkyl; A− is a non-nucleophilic anion, selected from the group (BF4)−, (SbF6)−, (PF6)−, (B(C6F5))4−, C1-C20alkylsulfonate, C2-C20haloalkylsulfonate, unsubstituted C6-C10arylsulfonate, camphorsulfonate, and C6-C10arylsulfonate substituted by halogen, NO2, C1-C12alkyl, C1-C12halo-alkyl, C1-C12alkoxy or by COOR1; and R1 is C1-C20alkyl, phenyl, benzyl; or phenyl mono- or poly-substituted by C1-C12alkyl, C1-C12alkoxy or by halogen; with the
    Type: Grant
    Filed: December 18, 2000
    Date of Patent: October 23, 2001
    Assignee: CIBA Specialty Chemicals Corp.
    Inventors: Reinhard Schulz, Jean-Luc Birbaum, Jean-Pierre Wolf, Stephan Ilg, Hitoshi Yamato, Toshikage Asakura
  • Patent number: 6235727
    Abstract: Compounds of the formula I are suitable for the production of pharmaceuticals for the prophylaxis and therapy of disorders in the course of which an increased activity of matrix-degrading enzymes is involved.
    Type: Grant
    Filed: July 15, 1999
    Date of Patent: May 22, 2001
    Assignee: Aventis Pharma Deutschland GmbH
    Inventors: Manfred Schudok, Wilfried Schwab, Gerhard Zoller, Eckart Bartnik, Frank Büttner, Klaus-Ulrich Weithmann
  • Patent number: 6225504
    Abstract: A process for the preparation of the formula Ar13−xP[(Ar2(OZ)y]x  I wherein Ar1 and Ar2 are individually aromatic of 6 to 20 carbon atoms or heteroaromatic of 4 to 9 carbon atoms, each unsubstituted or substituted with at least one member of the group consisting of halogen, carboxyl, —OH, alkyl of 1 to 6 carbon atoms, phenyl and naphthyl, Ar1 has one valence and R2 has y+1 valences, x is an integer of 1, 2 or 3, y is 1 or 2, Z is carbohydrate with a glycosidic bond comprising reacting a hydrocarbon halide of the formula Z′—X  II when Z′ has the definition of Z with —OH protected and X is chlorine, bromine or fluorine with a phosphane of the formula Ar13−xP[(Ar2 (OH)y]x  III in a multi-phase reaction medium in the presence of a base and a phase transfer catalyst to form a phosphane of the formula Ar13−xP[(Ar2(OZ1)y]x  IV and removal of the protective groups to form a compound of Fo
    Type: Grant
    Filed: June 23, 1999
    Date of Patent: May 1, 2001
    Assignee: Celanese GmbH
    Inventors: Sandra Bogdanovic, Matthias Beller, Alexander Zapf, Jurgen Krauter
  • Patent number: 6210830
    Abstract: The invention relates to novel lithium fluorophosphates of the general formula Li+[PFa(CHbFc(CF3)d)e]−,  (I) wherein a is 1, 2, 3, 4 or 5, b is 0 or 1, c is 0, 1, 2 or 3, d is 0, 1, 2 or 3 and e is 1, 2, 3 or 4, with the condition that the sum of a+e is equal to 6, the sum of b+c+d is equal to 3 and b and c are not simultaneously 0, with the proviso that the ligands (CHbFc(CF3)d) may be different, a process for producing said compounds, their use in electrolytes, and also lithium batteries produced using said electrolytes.
    Type: Grant
    Filed: March 8, 2000
    Date of Patent: April 3, 2001
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Peter Sartori, Nikolai Ignatyev
  • Patent number: 6211397
    Abstract: A process for the preparation of &agr;-chloromethylene-triorganylphosphorane derivatives I (radicals R are C-organic substituents and A stands for CN or CO-B where B is a C-organic or O-organic radical which is inert under chlorination conditions) by chlorination of phosphoranes II with chlorine, wherein the chlorination is carried out in the presence of a mineral base as hydrogen chloride acceptor and the chlorine and base are fed to the reaction mixture concurrently but separately at the rates at which they are consumed. The reaction products I are important intermediates for plant protectants.
    Type: Grant
    Filed: March 2, 1994
    Date of Patent: April 3, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Schaefer, Ernst Buschmann, Gernot Reissenweber
  • Patent number: 6169179
    Abstract: A method for manufacturing (3S,4R)-4-[(R)-1′-formylethyl]azetidin-2-one derivatives represented by formula (3) wherein R1 represents a hydrogen atom or a protective group, through asymmetric hydroformylation of 4-vinylazetidin-2-one represented by formula (1) wherein R1 has the same meaning as described above; in the presence of a rhodium complex and a (2S,4S)-diphosphine compound represented by formula (2) wherein R2 represents a phenyl group which may be substituted with 1-5 substituent(s) selected from a lower alkyl group, a lower alkoxy group, and a halogen atom. By use of both an inexpensive optically active diphosphine compound and a rhodium complex as catalysts, intermediate compounds important for carbapenem antibiotics can be manufactured with high selectivity and efficiency.
    Type: Grant
    Filed: June 10, 1999
    Date of Patent: January 2, 2001
    Assignee: Takasago International Corporation
    Inventors: Howard Alper, Takao Saito, Takashi Miura
  • Patent number: 6075154
    Abstract: A novel phosphine compound usable as a catalyst in various asymmetric synthetic reactions is disclosed. The compound is a 2,2'-bis(diarylphosphino)-6,6'-bis(trifluoromethyl)-1,1'-biphenyl of (1): ##STR1## where R is a phenyl group or a phenyl group substituted by lower alkyl group, lower alkoxy group, halogen atom, or lower haloalkyl group.
    Type: Grant
    Filed: July 30, 1998
    Date of Patent: June 13, 2000
    Assignee: Takasago International Corporation
    Inventors: Yoshiharu Gonda, Yoji Hori, Akio Yamaguchi, Toshimitsu Hagiwara
  • Patent number: 6040461
    Abstract: The invention relates to a process for the preparation of vitamin D.sub.3 compounds of formula I. ##STR1## Wherein A is a single or a double bond; B is a single, cis-double, trans double or a triple bond; R.sub.1 and R.sub.2 are independently hydrogen, a lower alkyl, e.g., a C.sub.1 -C.sub.4 alkyl; R.sub.3 and R.sub.4 are independently a lower alkyl, e.g., C.sub.1 -C.sub.4 alkyl, a hydroxyalkyl, and a haloalkyl, e.g., a fluoroalkyl; and X and Y are independently hydrogen or hydroxy in the case when B is a single or a double bond.
    Type: Grant
    Filed: May 11, 1999
    Date of Patent: March 21, 2000
    Assignees: Hoffmann-La Roche Inc., Syntex (U.S.A.)
    Inventors: Andrew David Batcho, Percy Sarwood Manchand, Milan Radoje Uskokovic
  • Patent number: 6020528
    Abstract: Compounds of the formula I ##STR1## in which R.sub.1 is C.sub.1 -C.sub.4 alkyl, R.sub.2 is hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy and R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 independently of one another are hydrogen, halogen, C.sub.1 -C.sub.20 alkyl, cyclopentyl, cyclohexyl, C.sub.2 -C.sub.12 alkenyl, C.sub.2 -C.sub.18 alkyl which is interrupted by one or more oxygen atoms, or are phenyl-substituted C.sub.1 -C.sub.4 alkyl, or are phenyl which is unsubstituted or is mono- or disubstituted by C.sub.1 -C.sub.4 alkyl and/or C.sub.1 -C.sub.4 alkoxy with the provisos that at least one of the radicals R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 is other than hydrogen and that, if R.sub.1 and R.sub.2 are methyl, R.sub.3 and R.sub.6 are not methyl, and mixtures of such compounds with .alpha.-hydroxy ketones, benzophenones and .alpha.-amino ketones, are suitable as photoinitiators.
    Type: Grant
    Filed: February 26, 1997
    Date of Patent: February 1, 2000
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: David George Leppard, Manfred Kohler, Andreas Valet
  • Patent number: 5969195
    Abstract: A process for hydrolyzing alkyl monohalides comprises using activated carbon impregnated with alkali metal hydroxide or alkaline earth metal hydroxide in the presence of water and converting the alkyl monohalides virtually quantitatively into the corresponding alcohols. Apparatus for carrying out the process comprises at least one, preferably two, especially three, reactors (2), especially tubular reactors. The process is also particularly useful for preparing alcohols.
    Type: Grant
    Filed: May 12, 1998
    Date of Patent: October 19, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Uwe Stabel, Gerhard Fahrbach, Werner Neumann
  • Patent number: 5945521
    Abstract: Methods and intermediates for the preparation of oligomers containing diastereomerically enriched phosphorothioate linkages are disclosed.
    Type: Grant
    Filed: October 9, 1997
    Date of Patent: August 31, 1999
    Assignee: McGill University
    Inventors: George Just, Zhili Xin, Eric Marsault, Yi Jin
  • Patent number: 5919983
    Abstract: A catalyst activator, comprising a cation which is a Bronsted acid capable of donating a proton, and an inert, compatible, noncoordinating, anion, characterized by a solubility constant at 25.degree. C. in hexane, cyclohexane or methylcyclohexane of at least 5 weight percent.
    Type: Grant
    Filed: March 14, 1997
    Date of Patent: July 6, 1999
    Assignee: The Dow Chemical Company
    Inventors: Robert K. Rosen, Daniel D. VanderLende
  • Patent number: 5908931
    Abstract: The present invention relates particularly to novel preorganized hexadentate ligands that are suitable for completing with a radionuclide, and are useful as general imaging agents for diagnostic purposes.
    Type: Grant
    Filed: December 14, 1990
    Date of Patent: June 1, 1999
    Assignee: Mallinckrodt Inc.
    Inventors: Raghavan Rajagopalan, William L. Neumann, Dennis L. Nosco
  • Patent number: 5874628
    Abstract: The invention is an improved method for the preparation of tertiary phosphines by way of cross-coupling of aryl, alkenyl, cycloalkenyl or aralkyl halides or aryl, alkenyl, cycloalkenyl or aralkyl sulfonate esters with chlorophosphines in the presence of a catalyst and a reductant. The general reaction scheme is shown below: ##STR1## wherein R.sup.1 is aryl, alkenyl, cycloalkenyl or aralkyl, any of which may be substituted by one or more of the following: alkyl, aryl, aralkyl, alkoxy, alkanoyl, chloro, fluoro, alkoxycarbonyl, cyano, trifluoromethyl, cycloalkyl, or CONR.sup.4 R.sup.5 wherein R.sup.4 and R.sup.5 are independently hydrogen, alkyl, aryl or aralkyl; R.sup.2 and R.sup.3 are independently aryl, alkyl, aralkyl, any of which may be substituted by one or more of the following: alkyl, aryl, aralkyl, alkoxy, alkanoyl, chloro, fluoro, alkoxycarbonyl, cyano, trifluoromethyl, cycloalkyl or CoNR.sup.4 R.sup.5 wherein R.sup.4 and R.sup.5 are independently hydrogen, alkyl, aryl or aralkyl; and n is 2 where R.
    Type: Grant
    Filed: March 26, 1997
    Date of Patent: February 23, 1999
    Assignee: Monsanto Company
    Inventors: Scott A. Laneman, David J. Ager, Amihia Eisenstadt
  • Patent number: 5861540
    Abstract: Synthetic procedures to tetraalkyls, tetraacids and dianhydrides substituted 1,1,1-triaryl-2,2,2-trifluoroethanes which comprises: (1) 1,1-bis(dialkylaryl)-1-aryl-2,2,2 -trifluoroethane, (2) 1,1-bis(dicarboxyaryl)-1-aryl-2,2,2-trifluoroethane or (3) cyclic dianhydride or diamine of 1,1-bis(dialkylaryl)-1-aryl-2,2,2-trifluoroethanes. The synthesis of (1) is accomplished by the condensation reaction of an aryltrifluoromethyl ketone with a dialkylaryl compound. The synthesis of (2) is accomplished by oxidation of (1). The synthesis dianhydride of (3) is accomplished by the conversion of (2) to its corresponding cyclic dianhydride. The synthesis of the diamine is accomplished by the similar reaction of an aryltrifluoromethyl ketone with aniline or alkyl substituted or disubstituted anilines. Also, other derivatives of the above are formed by nucleophilic displacement reactions.
    Type: Grant
    Filed: April 15, 1994
    Date of Patent: January 19, 1999
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: William B. Alston, Roy F. Gratz
  • Patent number: 5847222
    Abstract: The present invention provides a ligand for a novel catalyst superior in such characteristics as selectivity (chemoselectivity and enantioselectivity) and catalytic activity in asymmetric synthesis reactions and a ligand for a novel catalyst effective in an asymmetric hydrogenation reaction in particular. The ligand is an optically active diphosphine compound represented by the following formula: ##STR1## where Ph is a phenyl group, X is a chlorine or bromine atom, and R.sup.1 and R.sup.2 are each an alkyl group having 1 to 3 carbon atoms.
    Type: Grant
    Filed: August 26, 1997
    Date of Patent: December 8, 1998
    Assignee: Takasago International Corporation
    Inventors: Tohru Yokozawa, Noboru Sayo, Kazuhiko Matsumura, Hidenori Kumobayashi
  • Patent number: 5808163
    Abstract: The invention relates to chiral tertiary alkyldiarylphosphines of the formula (I), ##STR1## where: R.sup.1 is (C.sub.1 -C.sub.4)alkyl, which can also be substituted by F, CF.sub.3, OCH.sub.3,Ar.sup.1, Ar.sup.2 are phenyl, naphthyl, anthracenyl, which can also bear one or more substituents selected from the group consisting of (C.sub.1 -C.sub.4)alkyl, (C.sub.1 -C.sub.4)alkoxy, CF.sub.3, F,* designates the chiral carbon atom which can have either an (R) or an (S) configuration,and also a process for preparing these compounds.
    Type: Grant
    Filed: July 17, 1996
    Date of Patent: September 15, 1998
    Assignee: Aventis Research & Technologies GmbH & Co. KG
    Inventors: Hans Millauer, Peter Brungs
  • Patent number: 5789623
    Abstract: The present invention relates to a hydroxybiarylphosphines of the formula ##STR1## in which Ar-Ar is biphenyl, 1-phenyinaphthyl or 1,1'-binaphthyl, R.sup.1 and R.sup.2 are identical or different and are F or alkoxy having in each case 1 to 8 carbon atoms or are substituted or unsubstituted aryl, a and b are identical or different and are an integer from 0 to 4, in which R.sup.3 and R.sup.4 are identical or different and are alkyl having 1 to 8 carbon atoms, cycloalkyl having 4 to 10 carbon atoms, alkaryl having 7 to 9 carbon atoms, Ar.sup.3 --(R.sup.5).sub.n, in which A.sup.3 is an aryl radical having 6 to 10 carbon atoms, R.sup.5 is CF.sub.3, dialkylamino having a total of 2 to 8 carbon atoms or --CH.sub.2 N(alkyl).sub.2 having 1 to 3 carbon atoms per alkyl and n is an integer from 0 to 5, or --R.sup.3 --R.sup.
    Type: Grant
    Filed: June 11, 1996
    Date of Patent: August 4, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Dieter Regnat, Hans-Jerg Kleiner
  • Patent number: 5789624
    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 norbomane 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: August 4, 1998
    Assignee: Hoechst Celanese Corporation
    Inventors: Jerry D. Unruh, Brigitte E. Segmuller, Gabriel R. Chapa, Kent E. Pryor
  • Patent number: 5777087
    Abstract: The present invention provides novel aryl diphosphines having the formula ##STR1## wherein X, Y, R.sub.1-18, m, m' and n are defined herein, and which can be complexed with a transition metal to form a novel catalyst useful in such applications as hydroformylation.
    Type: Grant
    Filed: April 18, 1996
    Date of Patent: July 7, 1998
    Assignee: Celanese International Corporation
    Inventors: Christian W. Kohlpaintner, Brian E. Hanson, Hao Ding
  • Patent number: 5773661
    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: September 2, 1997
    Date of Patent: June 30, 1998
    Assignee: Celanese International Corporation
    Inventors: Jerry D. Unruh, Brigitte E. Segmuller, Gabriel R. Chapa, Kent E. Pryor
  • 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: 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: 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: 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: 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: 5623089
    Abstract: Novel triphenylbis(fluoroalkoxy)phosphoranes and a process for their preparation are disclosed. Also disclosed is a process for making fluorinated ketals by reacting phosphoranes with fluorinated ketones.
    Type: Grant
    Filed: May 22, 1995
    Date of Patent: April 22, 1997
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Zhen-Yu Yang