A Nitrile Reactant Contains No Acyclic Or Alicyclic Carbon To Carbon Unsaturation Patents (Class 558/378)
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Publication number: 20140155632Abstract: 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: ApplicationFiled: February 27, 2012Publication date: June 5, 2014Inventors: Thomas Himmler, Lukas J. Goossen, Felix Rudolphi, Bingrui Song
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Patent number: 8669392Abstract: 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: GrantFiled: February 12, 2010Date of Patent: March 11, 2014Assignees: China Petroleum & Chemical Corporation, Beijing Research Institute of Chemical Industry, China Petroleum & Chemical CorporationInventors: Lunjia Xie, Yu Tian, Zaixing Feng, Siyuan Zhao, Yu Kang, Zhufang Sun
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Publication number: 20140058101Abstract: 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: ApplicationFiled: October 29, 2013Publication date: February 27, 2014Applicant: Evonik Degussa GmbHInventors: Herbert Plenio, Christoph Fleckenstein, Renat Kadyrov, Juan Almena, Axel Monsees, Thomas Riermeier
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Publication number: 20140031545Abstract: 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: ApplicationFiled: December 21, 2011Publication date: January 30, 2014Applicant: LUDWIG-MAXIMILIAN-UNIVERSITAT MUNCHENInventors: Paul Knochel, Sebastian Bernhardt, Georg Manolikakes
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Publication number: 20130245257Abstract: 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: ApplicationFiled: March 14, 2013Publication date: September 19, 2013Applicants: Sumitomo Chemical Company, Limited, Kyoto UniversityInventors: Yoshiji TAKEMOTO, Kazuo MURAKAMI
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Publication number: 20130225815Abstract: 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: ApplicationFiled: February 19, 2013Publication date: August 29, 2013Applicant: The Board of Trustees of the University of IllinoisInventors: John F. Hartwig, Hiroyuki Morimoto, Patrick Fier
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Publication number: 20130211106Abstract: 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: ApplicationFiled: March 25, 2011Publication date: August 15, 2013Inventors: 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
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Publication number: 20130204001Abstract: 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: ApplicationFiled: May 17, 2011Publication date: August 8, 2013Applicant: RHODIA OPERATIONSInventors: Roland Jacquot, Philippe Marion
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Publication number: 20130197257Abstract: 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: ApplicationFiled: March 14, 2013Publication date: August 1, 2013Applicant: Hoffmann-La Roche Inc.Inventor: Hoffmann-La Roche Inc.
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Publication number: 20130165660Abstract: 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: ApplicationFiled: June 22, 2011Publication date: June 27, 2013Applicant: JOHNSON MATTHEY PUBLIC LIMITED COMPANYInventors: Thomas John Colacot, Carin Johansson Seechurn, Sebastien Laurent Parisel
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Publication number: 20120309931Abstract: 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: ApplicationFiled: August 14, 2012Publication date: December 6, 2012Applicant: E. I. DU PONT DE NEMOURS AND COMPANYInventor: JELENA CIRAKOVIC
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Publication number: 20120130114Abstract: 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: ApplicationFiled: November 23, 2010Publication date: May 24, 2012Inventors: Chien-Chung Han, Hong-Pin Shih
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Patent number: 8143442Abstract: 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: GrantFiled: March 31, 2009Date of Patent: March 27, 2012Assignee: Hoffmann-LA Roche Inc.Inventors: Gerard John Harnett, Ursula Hoffmann, Michael Jansen, Reinhard Reents, Tim Sattelkau, Dennis A. Smith, Helmut Stahr
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Publication number: 20120046490Abstract: 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: ApplicationFiled: February 12, 2010Publication date: February 23, 2012Inventors: Lunjia Xie, Yu Tian, Zaixing Feng, Siyuan Zhao, Yu Kang, Zhufang Sun
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Patent number: 7858823Abstract: 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: GrantFiled: March 31, 2009Date of Patent: December 28, 2010Assignee: Hoffmann-La Roche Inc.Inventors: Ursula Hoffmann, Michael Jansen, Reinhard Reents, Helmut Stahr
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Publication number: 20090253928Abstract: 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: ApplicationFiled: March 31, 2009Publication date: October 8, 2009Inventors: Gerard John Harnett, Ursula Hoffmann, Michael Jansen, Reinhard Reents, Tim Sattelkau, Dennis A. Smith, Helmut Stahr
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Publication number: 20090253927Abstract: 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: ApplicationFiled: March 31, 2009Publication date: October 8, 2009Inventors: Ursula Hoffmann, Michael Jansen, Reinhard Reents, Helmut Stahr
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Patent number: 7268247Abstract: 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: GrantFiled: December 4, 2003Date of Patent: September 11, 2007Assignee: Syngenta Crop Protection, Inc.Inventor: Martin Zeller
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Patent number: 7041856Abstract: 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: GrantFiled: October 22, 2002Date of Patent: May 9, 2006Assignee: Sumitomo Chemical Company, LimitedInventors: Tamon Itahashi, Takashi Kamikawa
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Patent number: 7005534Abstract: 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 espType: GrantFiled: August 1, 2001Date of Patent: February 28, 2006Assignee: Clariant GmbHInventors: Manfred Schreiber, Georg Borchers, Oliver Mogck, Frank Weinelt
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Patent number: 6790975Abstract: 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: GrantFiled: March 19, 2002Date of Patent: September 14, 2004Assignee: Sony CorporationInventors: Mari Ichimura, Tadashi Ishibashi, Shinichiro Tamura
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Patent number: 6506926Abstract: 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: GrantFiled: March 28, 2000Date of Patent: January 14, 2003Assignee: Rhone-Poulenc AgroInventors: Didier Bernard, Alain Truchon
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Patent number: 6433209Abstract: 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: GrantFiled: January 26, 2000Date of Patent: August 13, 2002Assignee: Aventis Pharmaceuticals Inc.Inventors: Sithamalli V. Chandramouli, Michael K. O'Brien, Tory H. Powner
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Patent number: 6433214Abstract: 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: GrantFiled: April 3, 2000Date of Patent: August 13, 2002Assignee: Dipharma S.p.A.Inventors: Graziano Castaldi, Antonio Tarquini, Renzo Rossi
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Patent number: 6407253Abstract: 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: GrantFiled: July 14, 1999Date of Patent: June 18, 2002Assignee: Sanofi-SynthelaboInventors: Mouad Alami, Gérard Cahiez, Bertrand Castro, Jean-Robert Dormoy, Eric Riguet
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Patent number: 6392111Abstract: 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: GrantFiled: March 21, 2001Date of Patent: May 21, 2002Assignee: Studiengesellschaft Kohle mbHInventors: Manfred T. Reetz, Gunther Lohmer, Renate Lohmer, Elke Westermann
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Patent number: 6392080Abstract: 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: GrantFiled: June 30, 1999Date of Patent: May 21, 2002Assignee: Sanofi-Stnth{dot over (e)}laboInventors: Mouad Alami, Gérard Cahiez, Bertrand Castro, Eric Riguet
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Patent number: 6291730Abstract: 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: GrantFiled: January 28, 1998Date of Patent: September 18, 2001Assignee: E. I. du Pont de Nemours and CompanyInventors: Ralph Thomas Baker, Viacheslav Alexandrovich Petrov, Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
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Patent number: 6218564Abstract: 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: GrantFiled: June 10, 1999Date of Patent: April 17, 2001Assignee: Zeneca LimitedInventor: Michael John Monteith
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Patent number: 5922898Abstract: 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: GrantFiled: November 7, 1997Date of Patent: July 13, 1999Assignee: Catalytica Pharmaceuticals, Inc.Inventors: Joseph Arthur Miller, Robert Patrick Farrell
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Patent number: 5892094Abstract: 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: GrantFiled: December 22, 1997Date of Patent: April 6, 1999Assignee: Sumika Fine Chemicals Co., Ltd.Inventors: Tadashi Katsura, Hiroshi Shiratani, Kiyoshi Sugi, Nobushige Itaya
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Patent number: 5856557Abstract: 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: GrantFiled: June 12, 1997Date of Patent: January 5, 1999Assignee: Ube Industries, Ltd.Inventors: Yumiki Noda, Takashi Honma
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Patent number: 5763639Abstract: 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: GrantFiled: March 3, 1997Date of Patent: June 9, 1998Assignee: BASF AktiengesellschaftInventors: Ulrich Annen, Hans-Peter Seelmann-Eggebert, Rudi Widder, Reinhard Muller
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Patent number: 5739375Abstract: Methyl compounds are prepared from carbon acids by reaction with dimethyl carbonate in the presence of a nitrogen-containing base.Type: GrantFiled: April 4, 1997Date of Patent: April 14, 1998Assignee: BASF AktiengellschaftInventor: Rolf Fischer
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Patent number: 5449808Abstract: 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: GrantFiled: March 29, 1994Date of Patent: September 12, 1995Assignee: The Standard Oil CompanyInventors: Marco Pagnotta, Mark C. Cesa, Sandra L. Denman, Robert D. Boyer, Jr.
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Patent number: 5288912Abstract: 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: GrantFiled: February 12, 1993Date of Patent: February 22, 1994Assignee: Eastman Kodak CompanyInventor: Thomas J. Devon
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Patent number: 5288895Abstract: 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: GrantFiled: April 6, 1993Date of Patent: February 22, 1994Assignee: Elf SanofiInventors: Michel Bouisset, Alain Boudin
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Process for preparing phenyl butyronitriles and perfumery use of 2,2-dimethyl-4-phenyl valeronitrile
Patent number: 5179222Abstract: 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: GrantFiled: March 27, 1992Date of Patent: January 12, 1993Assignee: International Flavors & Fragrances Inc.Inventors: Anubhav P. S. Narula, John J. De Virgilio, William L. Schreiber -
Patent number: 5099054Abstract: 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: GrantFiled: February 14, 1991Date of Patent: March 24, 1992Assignee: Michigan State UniversityInventors: Thomas J. Pinnavaia, Chi-Li Lin
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Patent number: 5089651Abstract: 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: GrantFiled: January 2, 1991Date of Patent: February 18, 1992Assignee: Fuji Photo Film Co., Ltd.Inventors: Masato Taniguchi, Tadahisa Sato, Yuki Mizukawa
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Patent number: 4942221Abstract: The present invention relates to the synthesis of nitriles having an amine function on the adjacent carbon.Type: GrantFiled: August 4, 1987Date of Patent: July 17, 1990Assignee: Albert Rolland S.A.Inventors: Gerard Moinet, Thierry Imbert
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Patent number: 4933470Abstract: 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: GrantFiled: October 5, 1987Date of Patent: June 12, 1990Assignee: NeoRx CorporationInventor: David S. Jones
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Patent number: 4910326Abstract: 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: GrantFiled: March 10, 1988Date of Patent: March 20, 1990Assignee: Shionogi & Co., Ltd.Inventors: Sumimoto Shinzaburo, Ichiro Ishizuka, Hiroyuki Kai, Shiro Ueda, Akira Takase
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Patent number: 4894471Abstract: 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: GrantFiled: March 30, 1987Date of Patent: January 16, 1990Assignee: Consiglio Nazionale Delle RichercheInventors: Enrico Angeletti, Franco Trotta, Pietro Tundo, Paolo Venturello
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Patent number: 4889951Abstract: 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: GrantFiled: April 25, 1988Date of Patent: December 26, 1989Assignee: Ethyl CorporationInventor: Robert I. Davidson
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Patent number: 4847401Abstract: 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: GrantFiled: January 15, 1988Date of Patent: July 11, 1989Assignee: Merrell Dow Pharmaceuticals Inc.Inventors: Fritz Gerhart, Michael Kolb
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Patent number: 4822904Abstract: 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: GrantFiled: December 12, 1985Date of Patent: April 18, 1989Assignee: Ethyl CorporationInventor: Robert I. Davidson
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Patent number: 4814480Abstract: 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: GrantFiled: April 21, 1986Date of Patent: March 21, 1989Assignee: Ethyl CorporationInventor: Robert I. Davidson
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Patent number: 4814482Abstract: 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: GrantFiled: April 21, 1986Date of Patent: March 21, 1989Assignee: Ethyl CorporationInventor: Robert I. Davidson
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Patent number: 4808748Abstract: 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: GrantFiled: December 12, 1985Date of Patent: February 28, 1989Assignee: Ethyl CorporationInventors: Ronny W. Lin, Robert I. Davidson