Replacing Hydrogen With Cyano (e.g., Malononitrile From Acetonitrile, Etc.) Patents (Class 558/348)
  • Patent number: 10087201
    Abstract: A process of hydrolyzing a monodentate, bidentate or tridentate phosphorus-based phosphite ester ligand or ligand blend for a transition metal catalyst comprising contacting the ligand or ligand blend with a hydrolysis catalyst of the formula (R11X11)nP(OH)3-n where n is 0, 1 or 2 wherein the ligand or ligand blend comprises one or more of (i) a bidentate biphosphite ligand of formula (III), (R12—X12)(R13—X13)P—X14—Y—X24—P(X22—R22)(X23—R23), (ii) a tridentate triphosphite ligand of formula (IIIA) (R12—X12)(R13—X13)P—X14—Y—X32—P(X34—R34)—(X33—Y2—K24—P(X23—R23)—(X22—R22) or (iii) a monodentate phosphite ligand of formula (IV) P(X1—R1)(X2—R2)(X3—R3) where each X is oxygen or a bond and each Y is an optionally substituted C6-C20 arylene, followed by separation of the ligand hydrolysis products.
    Type: Grant
    Filed: May 24, 2013
    Date of Patent: October 2, 2018
    Assignee: INVISTA NORTH AMERICA S.A R.L.
    Inventors: Sudhir Aki, Thomas E. Vos
  • Patent number: 9932298
    Abstract: The invention provides methods useful in the industrial scale process for hydrocyanation of butadiene to adiponitrile for recycle of unwanted byproduct 2-methyl-3-butenenitrile (2M3BN) by conversion to process intermediate pentenenitrile. The invention provides a process for generating catalysts useful for carrying out the hydrocyanation of butadiene to adiponitrile, the process comprising contacting the 2M3BN and a solution of a nickel-ligand catalyst in cis-2-pentenenitrile (cis-2PN), trans-2-pentenenitrile (trans-2PN), or a mixture thereof. The improved methods of the invention can provide improved catalyst solubility for bidentate ligands without a requirement for a Lewis acid catalyst promoter such as zinc chloride to be present.
    Type: Grant
    Filed: December 5, 2013
    Date of Patent: April 3, 2018
    Assignee: INVISTA NORTH AMERICA S.A R.L.
    Inventor: Thomas E. Vos
  • Patent number: 8563279
    Abstract: Described is a method for the preparation of renin inhibitors such as aliskiren, and intermediates useful therein. The method introduces a nitrogen-containing intermediate such as a lactone of formula (8). with R4 being a branched C3—6 alkyl. In the preparation of the lactone, or related intermediates, a desired stereochemical configuration can be controlled by starting from a chiral aldehyde satisfying formula (10).
    Type: Grant
    Filed: December 19, 2008
    Date of Patent: October 22, 2013
    Assignee: DSM IP Assets B.V.
    Inventors: Ben De Lange, Anna Maria Cornelia Francisca Castelijns, Johannes Gerardus De Vries, Andreas Hendrikus Maria De Vries, Jeroen Antonius Franciscus Boogers, Quirinus Bernardus Broxterman
  • Patent number: 8183404
    Abstract: The present invention is to provide a process for producing dicyanonorbornane characterized by causing hydrogen cyanide to undergo addition reaction with cyanonorbornene (bicyclo[2.2.1]-5-heptene-2-carbonitrile) in the presence of a zerovalent nickel complex catalyst which is produced by using a phosphite represented by P(x)(y)(z) (wherein P is a phosphorus atom, and x, y and z are each OR, where R represents an aryl group having not more than 18 carbon atoms) as a ligand to reduce a nickel halide with at least one metal selected among zinc, cadmium, beryllium, aluminum, iron and cobalt, wherein the phosphite is one which has a phosphate content of 1.0 weight % or lower based on the whole phosphite.
    Type: Grant
    Filed: June 22, 2007
    Date of Patent: May 22, 2012
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Norihiko Fukatsu, Hiroyuki Morijiri, Chitoshi Shimakawa, Koichi Tokunaga, Seiichi Kobayashi
  • Publication number: 20110008852
    Abstract: Described is a method for the preparation of renin inhibitors such as aliskiren, and intermediates useful therein. The method introduces a nitrogen-containing intermediate such as a lactone of formula (8). with R4 being a branched C3—6 alkyl. In the preparation of the lactone, or related intermediates, a desired stereochemical configuration can be controlled by starting from a chiral aldehyde satisfying formula (10).
    Type: Application
    Filed: December 19, 2008
    Publication date: January 13, 2011
    Inventors: Ben De Lange, Anna Maria Cornelia Francisca Castelijns, Johannes Gerardus De Vries, Andreas Hendrikus Maria De Vries, Jeroen Antonius Boogers, Quirinus Bernardus Broxterman
  • Publication number: 20100249443
    Abstract: The present invention relates to titanium catalysts for asymmetric synthesis reactions produced by bringing a reaction mixture obtained by contacting water and a titanium alkoxide into contact with an optically active ligand represented by the general formula (a), wherein R1, R2, R3, and R4 are independently a hydrogen atom, an alkyl group, or the like, and A* represents a group with two or more carbon atoms having an asymmetric carbon atom or axial asymmetry. The invention further relates to a process for asymmetric cyanation of imines, wherein the process comprises reacting an imine with a cyanating agent in the presence of the titanium catalyst.
    Type: Application
    Filed: September 26, 2008
    Publication date: September 30, 2010
    Applicant: Agency for Science, Technology and Research
    Inventors: Abdul Majeed Seayad, Balamurugan Ramalingam, Christina Chai, Takushi Nagata, Kazuhiko Yoshinaga
  • Patent number: 7470805
    Abstract: A process of hydrocyanation of diolefins such as butadiene is carried out in the presence of a catalytic system comprising a transition metal and mono- and pluri-dentate organophosphorus ligands. The reaction medium containing branched nitrites subsequently is isomerized in the absence of hydrogen cyanide.
    Type: Grant
    Filed: June 27, 2006
    Date of Patent: December 30, 2008
    Assignee: Rhodia Operations
    Inventors: Cécile Rosier, Philippe Marion, Damien Bourgeois
  • Patent number: 7265237
    Abstract: Certain chiral monophosphites and their monothio derivatives are suitable as ligands in the asymmetrical transition-metal-catalyzed hydrogenation, hydroborination and hydrocyanation of prochiral olefins, ketones and imines.
    Type: Grant
    Filed: June 5, 2001
    Date of Patent: September 4, 2007
    Assignee: Studiengesellschaft Kohle mbH
    Inventors: Manfred T. Reetz, Gerlinde Mehler, Andreas Meiswinkel
  • Publication number: 20040260112
    Abstract: The present invention relates to the manufacture of nitrile compounds from unsaturated organic compounds by reaction with hydrogen cyanide. It relates more particularly to the manufacture of nitrile compounds of use in the synthesis of adiponitrile, an important chemical intermediate in the manufacture of major chemical compounds, such as hexamethylenediamine and &egr;-caprolactam. The invention provides a process for the manufacture of organic compounds comprising at least one nitrile functional group by carrying out a hydrocyanation reaction between hydrogen cyanide and an organic compound comprising at least one ethylenic unsaturation. This reaction is carried out in the presence of a catalytic system comprising a metal element chosen from the group consisting of nickel, platinum and palladium and an organophosphorus ligand, the reaction medium additionally comprising an ionic liquid in the liquid state at least at the temperature at which the hydrocyanation reaction is carried out.
    Type: Application
    Filed: August 18, 2004
    Publication date: December 23, 2004
    Inventors: Jean-Marie Basset, Yves Chauvin, Jean-Christophe Galland, Gerald Niccolai, Christine Valerio, Christophe Vallee
  • Publication number: 20040198985
    Abstract: The present invention relates to processes for the preparation of a compound of the formula 1
    Type: Application
    Filed: November 10, 2003
    Publication date: October 7, 2004
    Applicant: Aventis Agriculture Ltd.
    Inventor: Jean-Erick Ancel
  • Publication number: 20040122251
    Abstract: The present invention relates to a process of hydrocyanation of ethylenically unsaturated organic compounds to compounds having at least one nitrile function, particularly the hydrocyanation of diolefins such as butadiene, or of substituted olefins such as alkene nitrites such as pentenenitriles; the subject hydrocyanation is carried out in the presence of a catalytic system comprising a metallic element and mono- and pluri-dentate organophosphorus ligands.
    Type: Application
    Filed: January 30, 2003
    Publication date: June 24, 2004
    Applicant: RHODIA POLYAMIDE INTERMEDIATES
    Inventors: Cecile Rosier, Philippe Marion, Damien Bourgeois
  • Publication number: 20030171608
    Abstract: Certain chiral monophosphites and their monothio derivatives are suitable as ligands in the asymmetrical transition-metal-catalyzed hydrogenation, hydroborination and hydrocyanation of prochiral olefins, ketones and imines.
    Type: Application
    Filed: December 4, 2002
    Publication date: September 11, 2003
    Inventors: Manfred T Reetz, Gerlinde Mehler, Andreas Meiswinkel
  • Patent number: 6486340
    Abstract: A method for producing an &agr;-aminonitrile, is disclosed, which method includes the step of oxidizing a tertiary amine with oxygen by using a transition metal catalyst in the presence of a cyanide. The &agr;-aminonitrile thus obtained can be easily converted to amino acids as well as various nitrogen-containing physiologically active materials.
    Type: Grant
    Filed: July 18, 2001
    Date of Patent: November 26, 2002
    Assignee: Osaka University
    Inventors: Shun-ichi Murahashi, Naruyoshi Komiya
  • Publication number: 20020087024
    Abstract: The invention relates to a continuous process, carried out in two steps, for the cyanoalkylation of compounds having one or more NH functions by reaction thereof with carbonyl compounds and hydrocyanic acid, in which the first step is carried out without pressure at a temperature which is below the boiling point of the reaction mixture.
    Type: Application
    Filed: October 5, 2001
    Publication date: July 4, 2002
    Applicant: BASF Aktiengesellschaft
    Inventors: Thomas Greindl, Gerold Braun, Friedrich Wirsing, Georg Krug
  • Patent number: 5292918
    Abstract: A process for preparing an (S,S) or (R,R) diastereoisomer of the formula: ##STR1## or salts, esters or amides thereof, wherein R.sup.3 and R.sup.4 independently represent hydrogen, alkyl, aryl or aryl substituted with halogen, alkyl, nitro or alkoxy, and n and m independently represent integers from one to six, comprising combining a cyanide compound of the formula:M.sup.1 C.tbd.N (III)wherein M.sup.1 is hydrogen, trimethylsilyl or a metal, with an optional proton source, a solvent and a Lewis acid of the formula:M.sup.2 X.sub.4, AlCl.sub.3 or BF.sub.3 (IV)wherein M.sup.2 is Sn or Ti and X represents chloro, bromo, fluoro or iodo, with an .alpha.-amino acid compound or salts or esters thereof, followed by addition of an acyl or acetal compound to give the diastereoisomer of formula (X).
    Type: Grant
    Filed: October 6, 1992
    Date of Patent: March 8, 1994
    Assignee: Schering Corporation
    Inventors: Jacques Gosteli, Ingrid Mergelsberg, Markus Tanner
  • Patent number: 4990630
    Abstract: The present invention relates to a 2,3-diaminoacrylonitrile derivative or salts thereof, having the formula ##STR1## wherein R represents an alkyl group (which may be substituted by unsubstituted or substituted phenyl groups, halogen atoms, C.sub.1-6 alkoxycarbonyl groups, carboxy groups, C.sub.1-6 alkoxycarbonyl C.sub.1-6 alkylthio groups, hydroxy groups, mercapto groups, cycloalkyl groups or heterocyclic groups containing oxygen atoms); an alkenyl group; a cycloalkyl group; an aryl group (which may be substituted by halogen atoms, C.sub.1-6 alkyl groups, nitro-groups, unsubstituted or substituted phenyl or phenoxy groups or heterocyclic groups containing oxygen atoms or sulfur atoms).The 2,3-diaminoacrylonitrile derivative can be used as starting materials for the production of pharmaceutical and/or agricultural intermediates such as cyanoimidazoles, cyanopyrazines or other cyano-substituted heterocycles.
    Type: Grant
    Filed: August 28, 1989
    Date of Patent: February 5, 1991
    Assignee: Nippon Soda Co., Ltd.
    Inventors: Katsunori Mikuma, Nobuhiro Umeda, Tomio Yagihara, Isami Hamamoto
  • Patent number: 4824987
    Abstract: A method of preparing m-trifluoromethylphenyl acetonitrile of the formula ##STR1## in which m-trifluoromethyl toluene is reacted with cyanogen chloride in the gas phase at 600.degree. to 750.degree. C.
    Type: Grant
    Filed: May 23, 1988
    Date of Patent: April 25, 1989
    Assignee: Degussa Aktiengesellschaft
    Inventors: Axel Kleemann, Herbert Klenk, Klaus Huthmacher, Dieter Most
  • Patent number: 4801728
    Abstract: The present invention relates to reaction mixtures and processes which employ an .omega.-phase catalyst for carrying out displacement reactions at a substantially enhanced rate.
    Type: Grant
    Filed: June 25, 1986
    Date of Patent: January 31, 1989
    Assignee: M&T Chemicals Inc.
    Inventors: Charles L. Liotta, Edward M. Burgess