A Nitrile Reactant Contains No Acyclic Or Alicyclic Carbon To Carbon Unsaturation Patents (Class 558/378)
  • Publication number: 20140155632
    Abstract: The invention relates to a process for preparing aryl- and heteroarylacetic acids and derivatives thereof by reaction of aryl or heteroaryl halides with malonic diesters in the presence of a palladium catalyst, of one or more bases and optionally of a phase transfer catalyst. This process enables the preparation of a multitude of functionalized aryl- and heteroarylacetic acids and derivatives thereof, especially also the preparation of arylacetic acids with sterically demanding substituents.
    Type: Application
    Filed: February 27, 2012
    Publication date: June 5, 2014
    Inventors: Thomas Himmler, Lukas J. Goossen, Felix Rudolphi, Bingrui Song
  • Patent number: 8669392
    Abstract: A process for preparing 2,3-di(non-linear-alkyl)-2-cyanosuccinate compounds, especially 2,3-diisopropyl-2-cyanosuccinate compounds, and processes for preparing 2,3-di(non-linear-alkyl)succinic acids and esters thereof by using the 2,3-di-non-linear propyl-2-cyanosuccinate compounds as intermediates are disclosed.
    Type: Grant
    Filed: February 12, 2010
    Date of Patent: March 11, 2014
    Assignees: China Petroleum & Chemical Corporation, Beijing Research Institute of Chemical Industry, China Petroleum & Chemical Corporation
    Inventors: Lunjia Xie, Yu Tian, Zaixing Feng, Siyuan Zhao, Yu Kang, Zhufang Sun
  • Publication number: 20140058101
    Abstract: The invention is directed to a phosphine compound represented by general formula (1) wherein R? and R? independently are selected from alkyl, cycloalkyl and 2-furyl radicals, or R? and R? are joined together to form with the phosphorous atom a carbon-phosphorous monocycle comprising at least 3 carbon atoms or a carbon-phosphorous bicycle; the alkyl radicals, cycloalkyl radicals, and carbon-phosphorous monocycle being unsubstituted or substituted by at least one radical selected from the group of alkyl, cycloalkyl, aryl, alkoxy, and aryloxy radicals; Cps is a partially substituted or completely substituted cyclopentadien-1-yl group, including substitutions resulting in a fused ring system, and wherein a substitution at the 1-position of the cyclopentadien-1-yl group is mandatory when the cyclopentadien-1-yl group is not part of a fused ring system or is part of an indenyl group. Also claimed is the use of these phosphines as ligands in catalytic reactions and the preparation of these phosphines.
    Type: Application
    Filed: October 29, 2013
    Publication date: February 27, 2014
    Applicant: Evonik Degussa GmbH
    Inventors: Herbert Plenio, Christoph Fleckenstein, Renat Kadyrov, Juan Almena, Axel Monsees, Thomas Riermeier
  • Publication number: 20140031545
    Abstract: Processes for making an organozinc reagents are disclosed comprising reacting (A) organomagnesium or organozinc complexes with (B) at least one coordination compound comprising one or more carboxylate groups and/or alcoholate groups and/or tertiary amine groups, optionally in combination with zinc ions and/or lithium ions and/or halide ions, wherein the halide ions are selected from chloride, bromide and iodide, the organozinc complex comprises an aryl group, a heteroaryl group or a benzyl group when the coordinating compound is a chelating polyamine, and the reaction is conducted in the presence of zinc complexed with at least one coordinating compound when reactant (A) comprises at least one organomagnesium complex. The resulting organozinc reagents may optionally be isolated from solvents to obtain a solid reagent. The reagents may be used for making organic compounds via Negishi cross-coupling reactions or via aldehyde and/or ketone oxidative addition reactions.
    Type: Application
    Filed: December 21, 2011
    Publication date: January 30, 2014
    Applicant: LUDWIG-MAXIMILIAN-UNIVERSITAT MUNCHEN
    Inventors: Paul Knochel, Sebastian Bernhardt, Georg Manolikakes
  • Publication number: 20130245257
    Abstract: The invention provides a compound having a heterocyclic skeleton of formula (I): wherein the substituents are as defined in the specification, as well as a tautomer thereof or a salt thereof. The invention also provides asymmetric synthesis methods involving the use of such a compound, tautomer thereof, or salt thereof, as a catalyst.
    Type: Application
    Filed: March 14, 2013
    Publication date: September 19, 2013
    Applicants: Sumitomo Chemical Company, Limited, Kyoto University
    Inventors: Yoshiji TAKEMOTO, Kazuo MURAKAMI
  • Publication number: 20130225815
    Abstract: A method of forming a fluorinated molecular entity includes reacting in a reaction mixture an aromatic halide, copper, a fluoroalkyl group, and a ligand. The aromatic halide includes an aromatic group and a halogen substituent bonded to the aromatic group. The ligand includes at least one group-V donor selected from phosphorus and an amine. The overall molar ratio of copper to aromatic halide in the reaction mixture is from 0.2 to 3. The method further includes forming a fluoroalkylarene including the aromatic group and the fluoroalkyl group bonded to the aromatic group. A composition, which may be used in the method, consists essentially of copper, the fluoroalkyl group, and the ligand, where the molar ratio of copper to the fluoroalkyl group is approximately 1.
    Type: Application
    Filed: February 19, 2013
    Publication date: August 29, 2013
    Applicant: The Board of Trustees of the University of Illinois
    Inventors: John F. Hartwig, Hiroyuki Morimoto, Patrick Fier
  • Publication number: 20130211106
    Abstract: Microwave irradiation is used to synthesize graphene and metallic nanocatalysts supported on graphene either by solid or solution phase. In solid phase methods, no solvents or additional reducing agents are required so the methods are “environmentally friendly” and economical, and the graphene and nanocatalysts are substantially free of residual contaminants. Recyclable, high efficiency Pd nanocatylysts are prepared by these methods.
    Type: Application
    Filed: March 25, 2011
    Publication date: August 15, 2013
    Inventors: M. Samy El-Shall, Victor Abdelsayed, Hassan M.A. Hassan, Abd EI Rahman S. Khder, Khaled M. Abouzeid, Qilin Dai, Parichehr Afshani, Frank Gupton, Ali R. Siamaki, Zeid Abdullah M. Alothman, Hamad Zaid Alkhathlan
  • Publication number: 20130204001
    Abstract: The production of compounds comprising nitrile functions and of cyclic imide compounds is described. Further described, is the production of compounds comprising nitrile functions from compounds comprising carboxylic functions, optionally of natural and renewable origin, and from a mixture N of dinitriles comprising 2-methylglutaronitrile (MGN), 2-ethylsuccinonitrile (ESN) and adiponitrile (AdN).
    Type: Application
    Filed: May 17, 2011
    Publication date: August 8, 2013
    Applicant: RHODIA OPERATIONS
    Inventors: Roland Jacquot, Philippe Marion
  • Publication number: 20130197257
    Abstract: A process for the preparation of a compound of formula (I): which is useful as an intermediate in the preparation of pharmaceutically active compounds.
    Type: Application
    Filed: March 14, 2013
    Publication date: August 1, 2013
    Applicant: Hoffmann-La Roche Inc.
    Inventor: Hoffmann-La Roche Inc.
  • Publication number: 20130165660
    Abstract: A complex of formula (1), wherein, M is palladium or nickel, R1 and R2 are independently organic groups having 1-20 carbon atoms, or R1 and R2 are linked to form a ring structure with the phosphorus atom, R3 is selected from the group consisting of substituted and unsubstituted aryl, substituted and unsubstituted heteroaryl, and substituted and unsubstituted metallocenyl, R4 is an organic group having 1-20 carbon atoms, n is 0, 1, 2, 3, 4 or 5, X is an anionic ligand. A process for the preparation of the complex, and its use in carbon-carbon or carbon-nitrogen coupling reactions is also provided.
    Type: Application
    Filed: June 22, 2011
    Publication date: June 27, 2013
    Applicant: JOHNSON MATTHEY PUBLIC LIMITED COMPANY
    Inventors: Thomas John Colacot, Carin Johansson Seechurn, Sebastien Laurent Parisel
  • Publication number: 20120309931
    Abstract: A high yield and high productivity processes for preparing 3-hydroxyglutaronitrile by reacting an epihalohydrin or a 4-halo-3-hydroxy-butanenitrile, or analogous compound containing a different leaving group, with cyanide (CN—) in the presence of water and an ionic liquid. The use of an ionic liquid as a cosolvent with water results in increased productivity and selectivity.
    Type: Application
    Filed: August 14, 2012
    Publication date: December 6, 2012
    Applicant: E. I. DU PONT DE NEMOURS AND COMPANY
    Inventor: JELENA CIRAKOVIC
  • Publication number: 20120130114
    Abstract: A method for direct functionalization of polyaniline and other molecules with at least one diiminoquinoid ring through C—C bond formation is described. Fluoride ion, or a weak base whose conjugated acid form has a pKa value of 1-10, is used as a catalyst to react the molecule with an organic compound that has an abstractable proton directly bonded to the target carbon atom thereof to be bonded to the diiminoquinoid ring and has a pKa value less than 30 for the abstractable proton.
    Type: Application
    Filed: November 23, 2010
    Publication date: May 24, 2012
    Inventors: Chien-Chung Han, Hong-Pin Shih
  • Patent number: 8143442
    Abstract: A process for the preparation of a compound of formula (Ia): which are useful as intermediates in the preparation of i.a. pharmaceutically active compounds.
    Type: Grant
    Filed: March 31, 2009
    Date of Patent: March 27, 2012
    Assignee: Hoffmann-LA Roche Inc.
    Inventors: Gerard John Harnett, Ursula Hoffmann, Michael Jansen, Reinhard Reents, Tim Sattelkau, Dennis A. Smith, Helmut Stahr
  • Publication number: 20120046490
    Abstract: A process for preparing 2,3-di(non-linear-alkyl)-2-cyanosuccinate compounds, especially 2,3-diisopropyl-2-cyanosuccinate compounds, and processes for preparing 2,3-di(non-linear-alkyl)succinic acids and esters thereof by using the 2,3-di-non-linear propyl-2-cyanosuccinate compounds as intermediates are disclosed.
    Type: Application
    Filed: February 12, 2010
    Publication date: February 23, 2012
    Inventors: Lunjia Xie, Yu Tian, Zaixing Feng, Siyuan Zhao, Yu Kang, Zhufang Sun
  • Patent number: 7858823
    Abstract: A process for the preparation of a compound of formula (I): which are useful as intermediates in the preparation of i.a. pharmaceutically active compounds.
    Type: Grant
    Filed: March 31, 2009
    Date of Patent: December 28, 2010
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Ursula Hoffmann, Michael Jansen, Reinhard Reents, Helmut Stahr
  • Publication number: 20090253928
    Abstract: A process for the preparation of a compound of formula (Ia): which are useful as intermediates in the preparation of i.a. pharmaceutically active compounds.
    Type: Application
    Filed: March 31, 2009
    Publication date: October 8, 2009
    Inventors: Gerard John Harnett, Ursula Hoffmann, Michael Jansen, Reinhard Reents, Tim Sattelkau, Dennis A. Smith, Helmut Stahr
  • Publication number: 20090253927
    Abstract: A process for the preparation of a compound of formula (I): which are useful as intermediates in the preparation of i.a. pharmaceutically active compounds.
    Type: Application
    Filed: March 31, 2009
    Publication date: October 8, 2009
    Inventors: Ursula Hoffmann, Michael Jansen, Reinhard Reents, Helmut Stahr
  • Patent number: 7268247
    Abstract: Phenylmalonic acid dinitriles are prepared by reaction of, for example, phenyl Kalides with malonic acid dinitrile in the presence of palladium catalysts and bases.
    Type: Grant
    Filed: December 4, 2003
    Date of Patent: September 11, 2007
    Assignee: Syngenta Crop Protection, Inc.
    Inventor: Martin Zeller
  • Patent number: 7041856
    Abstract: There are disclosed a process for producing a coupling compound of formula (1): (Y—)(n?1)R1—R2—(R1)(n??1),??(1) wherein R1 and R2 independently represent a substituted or unsubstituted aryl group, which process is characterized by reacting an unsaturated organic compound of formula (2): n?(R1X1n)??(2) wherein n, n?, and R1 are the same as defined above, and X1 is the same or different and independently represents a leaving group and bonded with a sp2 carbon atom of R1 group, with a boron compound of formula (3): m{R2(BX22)n?}??(3) wherein R2 and n? are the same as defined above, X2 represents a hydroxy group, an alkoxy group, in the presence of a catalyst containing (A) a nickel compound, and (B) a nitrogen-containing cyclic compound, and the catalyst.
    Type: Grant
    Filed: October 22, 2002
    Date of Patent: May 9, 2006
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tamon Itahashi, Takashi Kamikawa
  • Patent number: 7005534
    Abstract: The invention relates to a method for producing hydrolysis-stable ammonium nitriles by reacting a compound of formula (1), wherein R1, R2, and R3 are identical or different and represent linear or branched C1–C24-alkyl groups, C2–C24-alkenyl groups, substituted or non-substituted benzyl or C1–C4-alkoxy-C1–C4-alkyl groups, or wherein R1 and R2, together with the nitrogen atom to which they are bonded, form a ring with 4 to 6 C-atoms which can be substituted with C1–C5 alkyl, C1–C5 alkoxy, C1–C5 alkanoyl, phenyl, amino, ammonium, cyano, cyanamino, chlorine or bromine and which can contain in addition to the nitrogen atom, instead of the carbon atoms, one or two oxygen or nitrogen atoms, a group N—R6 or a group R3—N—R6, wherein R6 is hydrogen, C1–C5-alkyl, C2–C5-alkenyl, C2–C5-alkinyl, phenyl, C7–C9-aralkyl, C5–C7-cycloalkyl, C1–C6-alkanoyl, cyanomethyl or cyan, R4 and R5 are hydrogen, C1–C4-alkyl, C1–C4-alkenyl, C1–C4-alkoxy-C1–C4-alkyl, phenyl or C1–C3-alkylphenyl, preferably hydrogen, methyl or phenyl, R4 esp
    Type: Grant
    Filed: August 1, 2001
    Date of Patent: February 28, 2006
    Assignee: Clariant GmbH
    Inventors: Manfred Schreiber, Georg Borchers, Oliver Mogck, Frank Weinelt
  • Patent number: 6790975
    Abstract: This invention is an aminostyrylanthracene compound represented by, for example, the following general formula [I]. This compound is produced by condensation from a corresponding aminobenzaldehyde and a phosphonic ester or phosphonium salt. [where, in the general formula [I] above, R2 represents an unsubstituted aryl group, R1 represents an aryl group which may have a variety of substituents, and R3 to R5 each represent a hydrogen atom, a cyano group, or a hydrocarbon group.
    Type: Grant
    Filed: March 19, 2002
    Date of Patent: September 14, 2004
    Assignee: Sony Corporation
    Inventors: Mari Ichimura, Tadashi Ishibashi, Shinichiro Tamura
  • Patent number: 6506926
    Abstract: A process for preparing a compound of the formula: which comprises reacting a compound of the formula: wherein R3 is nitro or halo, with a compound of formula R1S—X wherein X is hydrogen or alkali metal.
    Type: Grant
    Filed: March 28, 2000
    Date of Patent: January 14, 2003
    Assignee: Rhone-Poulenc Agro
    Inventors: Didier Bernard, Alain Truchon
  • Patent number: 6433209
    Abstract: Methods for stereoselective substitution in which a (mono or un)-&agr;-substituted unprotected &bgr;-amino ester compound or salt thereof is reacted with an aliphatic electrophile in the presence of a base selected from alkyl lithium compounds, lithium hydride, lithium amide, lithium dialkyl amides and alkali hexamethyldisilylamines.
    Type: Grant
    Filed: January 26, 2000
    Date of Patent: August 13, 2002
    Assignee: Aventis Pharmaceuticals Inc.
    Inventors: Sithamalli V. Chandramouli, Michael K. O'Brien, Tory H. Powner
  • Patent number: 6433214
    Abstract: A process for the preparation of 2-(4-methylphenyl)benzoic acid C1-6alkyl esters by reaction of a sulfonic derivative of formula wherein R is C1-6alkyl and R1 is optionally perfluorinated C1-6alkyl or optionally substituted C1-6aryl, with a 4-methylphenylzinc halide.
    Type: Grant
    Filed: April 3, 2000
    Date of Patent: August 13, 2002
    Assignee: Dipharma S.p.A.
    Inventors: Graziano Castaldi, Antonio Tarquini, Renzo Rossi
  • Patent number: 6407253
    Abstract: The subject-matter of the invention is a process for the preparation of substituted 4-methylbiphenyls of general formula: in which R is a cyano group or a protected tetrazolyl group of formula: in which R1, situated at the 1 or 2 position of the tetrazolyl group, is a protective group, characterized in that a halobenzene of formula: in which Hal is a halogen atom and R has the same meaning as above, is reacted with a p-tolylmagnesium halide in the presence of a linear or branched polyether and of a catalyst comprising a transition metal.
    Type: Grant
    Filed: July 14, 1999
    Date of Patent: June 18, 2002
    Assignee: Sanofi-Synthelabo
    Inventors: Mouad Alami, Gérard Cahiez, Bertrand Castro, Jean-Robert Dormoy, Eric Riguet
  • Patent number: 6392080
    Abstract: The subject-matter of the invention is a process for the preparation of o-(p-tolyl)benzonitrile, characterized in that an o-halobenzonitrile is treated with a p-tolylmagnesium halide in the presence of a manganous salt and of a cocatalyst comprising a transition metal.
    Type: Grant
    Filed: June 30, 1999
    Date of Patent: May 21, 2002
    Assignee: Sanofi-Stnth{dot over (e)}labo
    Inventors: Mouad Alami, Gérard Cahiez, Bertrand Castro, Eric Riguet
  • Patent number: 6392111
    Abstract: Olefins containing aromatic substituents are synthesized without the addition of phosphonium salts or phosphanes with the aid of a PdII compound as a catalyst in the presence of nitrogen-containing additives such as N,N-dimethylglycine and a base.
    Type: Grant
    Filed: March 21, 2001
    Date of Patent: May 21, 2002
    Assignee: Studiengesellschaft Kohle mbH
    Inventors: Manfred T. Reetz, Gunther Lohmer, Renate Lohmer, Elke Westermann
  • Patent number: 6291730
    Abstract: A liquid phase process is disclosed for producing halogenated alkane adducts of the formula: CAR1R2CBR3R4 (where A, B, R1, R2, R3, and R4 are as defined in the specification) which involves contacting a corresponding halogenated alkane, AB, with a corresponding olefin, CR1R2═C3R4 in a dinitrile or cyclic carbonate ester solvent which divides the reaction mixture into two liquid phases and in the presence of a catalyst system containing: (i) at least one catalyst selected from monovalent and divalent copper; and optionally (ii) a promoter selected from aromatic or aliphatic heterocyclic compounds which contain at least one carbon-nitrogen double bond in the heterocyclic ring. When hydrochlorofluorocarbons are formed, the chlorine content may be reduced by reacting the hydrochlorofluorocarbons with HF. New compounds disclosed include CF3CF2CCl2CH2CCl3, CF3CCl2CH2CH2Cl and CF3CCl2CH2CHClF. These compounds are useful as intermediates for producing hydrofluorocarbons.
    Type: Grant
    Filed: January 28, 1998
    Date of Patent: September 18, 2001
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Ralph Thomas Baker, Viacheslav Alexandrovich Petrov, Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
  • Patent number: 6218564
    Abstract: A process for the preparation of a substituted aromatic compound in which a chloroaromatic compound and an alkyl-, alkenyl- or aryl-boronic acid ester or anhydride are coupled in the presence of palladium and a lipophilic aliphatic phosphine comprising at least one branched aliphatic group or a lipophilic aliphatic Dis(phosphine). Preferred phosphines include triisopropyl, triisobutyl and tricyclohexylphosphine.
    Type: Grant
    Filed: June 10, 1999
    Date of Patent: April 17, 2001
    Assignee: Zeneca Limited
    Inventor: Michael John Monteith
  • Patent number: 5922898
    Abstract: The present invention provides a process for preparing biaryl compounds comprising reacting an arylmetal reagent selected from arylmagnesium reagents and aryllithium reagents with an arylhalide in the presence of a catalyst system comprising a catalyst selected from nickel catalysts and palladium catalysts and a cocatalyst selected from zinc cocatalysts and cadmium cocatalysts. The present invention specifically provides a process for the preparation of 2-(4'-methylphenyl)benzonitrile comprising reacting a 4-methylphenylmagnesium reagent with a 2-halobenzonitrile in the presence of a catalyst system comprising a catalyst selected from nickel catalysts and palladium catalysts and a zinc cocatalyst.
    Type: Grant
    Filed: November 7, 1997
    Date of Patent: July 13, 1999
    Assignee: Catalytica Pharmaceuticals, Inc.
    Inventors: Joseph Arthur Miller, Robert Patrick Farrell
  • Patent number: 5892094
    Abstract: Process for preparing 4'-methyl-2-cyanobiphenyl, comprising, catalytically hydrogenating at least one brominated cyanobiphenyl compound selected from 4'-dibromomethyl-2-cyanobiphenyl and 4'-bromomethyl-2-cyanobiphenyl; and process for regenerating 4'-methyl-2-cyanobiphenyl, comprising, catalytically hydrogenating at least one brominated cyanobiphenyl compound selected from 4'-dibromomethyl-2-cyanobiphenyl and 4'-bromomethyl-2-cyanobiphenyl, contained in a filtrate prepared by brominating 4'-methyl-2-cyanobiphenyl in a solvent; crystallizing 4'-bromomethyl-2-cyanobiphenyl from the resulting reaction mixture; and removing the resulting crystals from the reaction mixture by filtration. 4'-Methyl-2-cyanobiphenyl can be used as starting materials for 4'-bromomethyl-2-cyanobiphenyl.
    Type: Grant
    Filed: December 22, 1997
    Date of Patent: April 6, 1999
    Assignee: Sumika Fine Chemicals Co., Ltd.
    Inventors: Tadashi Katsura, Hiroshi Shiratani, Kiyoshi Sugi, Nobushige Itaya
  • Patent number: 5856557
    Abstract: A 2,2',5,5',6,6'-hexafluorobiphenyl-3,3',4,4'-tetracarboxylic acid precursor as an intermediate material for a highly functional fluororesin may be produced at a high yield by reacting tetrafluorophthalonitrile with an alkali metal iodide.
    Type: Grant
    Filed: June 12, 1997
    Date of Patent: January 5, 1999
    Assignee: Ube Industries, Ltd.
    Inventors: Yumiki Noda, Takashi Honma
  • Patent number: 5763639
    Abstract: A process for preparing quaternized glycine nitriles of formula I ##STR1## comprising reaction of the corresponding precursor amine, aldehyde, hydrocyanic acid or alkali metal cyanide, and subsequent quaternization with an alkylating agent, wherein the reaction and quaternization are carried out successively in aqueous medium without isolation of an intermediate.
    Type: Grant
    Filed: March 3, 1997
    Date of Patent: June 9, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Ulrich Annen, Hans-Peter Seelmann-Eggebert, Rudi Widder, Reinhard Muller
  • Patent number: 5739375
    Abstract: Methyl compounds are prepared from carbon acids by reaction with dimethyl carbonate in the presence of a nitrogen-containing base.
    Type: Grant
    Filed: April 4, 1997
    Date of Patent: April 14, 1998
    Assignee: BASF Aktiengellschaft
    Inventor: Rolf Fischer
  • Patent number: 5449808
    Abstract: A process which comprises contacting and catalytically reacting under essentially anhydrous conditions in the liquid phase an amide with a nitrile according to the equation:RCONH.sub.2 +R.sup.1 CN.revreaction.RCN+R.sup.1 CONH.sub.2where R and R.sup.
    Type: Grant
    Filed: March 29, 1994
    Date of Patent: September 12, 1995
    Assignee: The Standard Oil Company
    Inventors: Marco Pagnotta, Mark C. Cesa, Sandra L. Denman, Robert D. Boyer, Jr.
  • Patent number: 5288895
    Abstract: The subject of the invention is a process for the preparation of 4-methyl-2'-cyanobiphenyl of formula: ##STR1## wherein a benzonitrile halide of general formula: ##STR2## in which Hal represents a halogen atom, is reacted, in the presence of a manganese salt, with an organometallic derivative of general formula: ##STR3## in which X represents a halogen atom, and the complex obtained is then hydrolysed, which provides the desired compound.
    Type: Grant
    Filed: April 6, 1993
    Date of Patent: February 22, 1994
    Assignee: Elf Sanofi
    Inventors: Michel Bouisset, Alain Boudin
  • Patent number: 5288912
    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: February 12, 1993
    Date of Patent: February 22, 1994
    Assignee: Eastman Kodak Company
    Inventor: Thomas J. Devon
  • Patent number: 5179222
    Abstract: Described is the use in imparting, augmenting or enhancing aromas to or in perfume compositions, colognes and perfumed articles by admixing therewith an aroma imparting, augmenting or enhancing quantity of 2,2-dimethyl-4-phenyl valeronitrile defined according to the structure: ##STR1## Also described herein is a process for preparing phenyl butyronitriles by reacting isobutyronitrile having the structure: ##STR2## with a styrene derivative defined according to the structure: ##STR3## according to the reaction: ##STR4## in the presence of a catalyst selected from the group consisting of sodium hydride and lithium diisopropyl amide having the structure: ##STR5## at a temperature in the range of from about 90.degree. C. up to about 130.degree. C. yielding more than about 65% by weight of product wherein R.sub.1 and R.sub.2 are the same or different and each represents hydrogen or methyl.
    Type: Grant
    Filed: March 27, 1992
    Date of Patent: January 12, 1993
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Anubhav P. S. Narula, John J. De Virgilio, William L. Schreiber
  • Patent number: 5099054
    Abstract: In a method of carrying out organic conversions via heterogeneous phase transfer catalysis by contacting immiscible liquid phases containing respective substances capable of interacting, with a solid catalyst to promote the transfer of reactive species from one liquid phase to another, the improvement comprises employing as catalyst a cation exchanged form of a 2:1 layered silicate clay with layer charge densities in the range of above 0.4 to 2.0 containing an onium ion containing one or more alkyl hydrocarbon chains and maintaining the materials in emulsified form by having a sufficient chain length of an alkyl group relative to the charge density of the clay.
    Type: Grant
    Filed: February 14, 1991
    Date of Patent: March 24, 1992
    Assignee: Michigan State University
    Inventors: Thomas J. Pinnavaia, Chi-Li Lin
  • Patent number: 5089651
    Abstract: A process for producing a 3-iminonitrile represented by the following general formula (I): ##STR1## wherein M represents an alkali metal, which comprises reacting acetonitrile with an alkali metal hydride in an amount of from 0.01 to 0.5 molar equivalent to acetonitrile; and a process for producing a 3-iminonitrile of the formula (II): ##STR2## which comprises mixing the compound represented by the foregoing general formula (II), which was obtained by the reaction between acetonitrile and the alkali metal hydride, with a protic solvent, are disclosed. These processes are useful for producing the desired 3-iminonitrile safely, inexpensively and in high yields.
    Type: Grant
    Filed: January 2, 1991
    Date of Patent: February 18, 1992
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Masato Taniguchi, Tadahisa Sato, Yuki Mizukawa
  • Patent number: 4942221
    Abstract: The present invention relates to the synthesis of nitriles having an amine function on the adjacent carbon.
    Type: Grant
    Filed: August 4, 1987
    Date of Patent: July 17, 1990
    Assignee: Albert Rolland S.A.
    Inventors: Gerard Moinet, Thierry Imbert
  • Patent number: 4933470
    Abstract: A method is described for producing vicinal diamines comprising the steps of converting a compound, possessing a leaving group on a carbon atom interposed between carbon atoms containing amino groups, to an aziridine-containing compound and reacting the latter compound with a nucleophile to form a vicinal diamine. The compound chosen for the rearrangement reaction may be selected from a wide range of compounds, including those with halide, heteroatom and aryl substituents. The amino groups may be blocked or unblocked. A variety of functional groups, including those which extend the carbon backbone, may be incorporated via opening of the aziridine-containing compound by addition of a selected nuclepohile. Aziridine-containing compositions and vicinal diamine compositions are disclosed. Functionalized vicinal diamines have numerous uses, including as intermediates for radionuclide-chelating ligands for use in the diagnosis and therapy of cancer.
    Type: Grant
    Filed: October 5, 1987
    Date of Patent: June 12, 1990
    Assignee: NeoRx Corporation
    Inventor: David S. Jones
  • Patent number: 4910326
    Abstract: A fluorinated .beta.-ketonitrile of the formula: ##STR1## in which: R is alkyl having plural fluorines and R.sup.1 is hydrogen or alkyl.
    Type: Grant
    Filed: March 10, 1988
    Date of Patent: March 20, 1990
    Assignee: Shionogi & Co., Ltd.
    Inventors: Sumimoto Shinzaburo, Ichiro Ishizuka, Hiroyuki Kai, Shiro Ueda, Akira Takase
  • Patent number: 4894471
    Abstract: A continuous process for the alkylation of CH-acid compounds with dialkyl carbonates in gas-liquid phase transfer catalysis conditions is described, consisting of contacting a mixture of a CH-acid compound (arylacetonitrile or malonic diester) and of a dialkylcarbonate, optionally added with an inert carrier (constituted by a polar or aprotic polar liquid or by a gas), with a catalytic bed comprising alumina spheres carrying a base and a phase transfer catalyst.
    Type: Grant
    Filed: March 30, 1987
    Date of Patent: January 16, 1990
    Assignee: Consiglio Nazionale Delle Richerche
    Inventors: Enrico Angeletti, Franco Trotta, Pietro Tundo, Paolo Venturello
  • Patent number: 4889951
    Abstract: Perfluoroalkylaromatic compounds containing at least two carbons in the perfluoroalkyl group are prepared by reacting an aromatic bromide or iodide with a potassium perfluoroalkanoate corresponding to the formula KOOC(CF.sub.2).sub.n CF.sub.3 wherein n is an integer of at least one in the presence of cuprous iodide and a dipolar aprotic solvent.
    Type: Grant
    Filed: April 25, 1988
    Date of Patent: December 26, 1989
    Assignee: Ethyl Corporation
    Inventor: Robert I. Davidson
  • Patent number: 4847401
    Abstract: The large scale preparation of ethyl 2,2-difluoro-4- pentenoate and 2-fluorinated methyl aminoacetonitriles by reaction of 2-H-perfluoroethyl allyl ether and n-butyl lithium and fluoromethylacetonitrile and a Grignard reagent, respectively, is largly unsuccessful because of side reactions which convert intermediate products and reactants to undesired products. Applicants have overcome these problems by performing the reactions with cooling in a continuous manner in a flow reactor with short residence time.
    Type: Grant
    Filed: January 15, 1988
    Date of Patent: July 11, 1989
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Fritz Gerhart, Michael Kolb
  • Patent number: 4822904
    Abstract: Perfluoroalkylaromatic compounds containing at least two carbons in the perfluoroalkyl group are prepared by reacting an aromatic bromide or iodide with a potassium perfluoroalkanoate corresponding to the formula KOOC(CF.sub.2).sub.n CF.sub.3 wherein n is an integer of at least one in the presence of cuprous iodide and a dipolar aprotic solvent.
    Type: Grant
    Filed: December 12, 1985
    Date of Patent: April 18, 1989
    Assignee: Ethyl Corporation
    Inventor: Robert I. Davidson
  • Patent number: 4814480
    Abstract: Trifluoromethylaromatic compounds are prepared by reacting the corresponding aromatic bromide or iodide with a tetraalkylammonium trifluoroacetate in the presence of cuprous iodide and a dipolar aprotic solvent.
    Type: Grant
    Filed: April 21, 1986
    Date of Patent: March 21, 1989
    Assignee: Ethyl Corporation
    Inventor: Robert I. Davidson
  • Patent number: 4814482
    Abstract: Trifluoromethylaromatic compounds are prepared by reacting the corresponding aromatic bromide or iodide with potassium trifluoroacetate in the presence of cuprous iodide, a phase transfer agent, and a dipolar aprotic solvent.
    Type: Grant
    Filed: April 21, 1986
    Date of Patent: March 21, 1989
    Assignee: Ethyl Corporation
    Inventor: Robert I. Davidson
  • Patent number: 4808748
    Abstract: Trifluoromethylaromatic compounds are prepared by reacting the corresponding aromatic bromide or iodide with potassium trifluoroacetate in the presence of cuprous iodide and a dipolar aprotic solvent.
    Type: Grant
    Filed: December 12, 1985
    Date of Patent: February 28, 1989
    Assignee: Ethyl Corporation
    Inventors: Ronny W. Lin, Robert I. Davidson