Forming Amine Group Directly By Reduction Patents (Class 564/415)
  • Patent number: 10315982
    Abstract: The present invention relates to a composition comprising: a) at least one primary, secondary or tertiary amine and b) at least one agent which masks the odor of said at least one amine, said at least one odor-masking agent comprising at least one ether (b1), optionally, but preferably, at least one terpene and/or one terpenoid (b2) and optionally, but preferably, at least one oxime (b3). The invention also relates to the use of an odor-masking agent in order to mask the odor of at least one amine.
    Type: Grant
    Filed: February 3, 2015
    Date of Patent: June 11, 2019
    Assignee: ARKEMA FRANCE
    Inventors: Christophe Ruppin, Christian Forquy
  • Publication number: 20140328748
    Abstract: The present application discloses complexes useful as catalysts for organic chemical synthesis including hydrogenation and dehydrogenation of unsaturated compounds or dehydrogenation of substrates. The range of hydrogenation substrate compounds includes esters, lactones, oils and fats, resulting in alcohols, diols, and triols as reaction products. The catalysts of current application can be used to catalyze a hydrogenation reaction under solvent free conditions. The present catalysts also allow the hydrogenation to proceed without added base, and it can be used in place of the conventional reduction methods employing hydrides of the main-group elements. Furthermore, the catalysts of the present application can catalyze a dehydrogenation reaction under homogenous and/or acceptorless conditions. As such, the catalysts provided herein can be useful in substantially reducing cost and improving the environmental profile of manufacturing processes for variety of chemicals.
    Type: Application
    Filed: August 20, 2012
    Publication date: November 6, 2014
    Inventors: Dmitri Goussev, Denis Spasyuk
  • Patent number: 8835687
    Abstract: Provided is a method for preparing 4,4?-dinitrodiphenylamine (4,4?-DNDPA) in high yield via the NASH reaction using a mixture of a bis-quaternary ammonium base and a base catalyst for the reaction of urea with nitrobenzene, and a method of preparing 4,4?-bis(alkylamino)diphenylamine (4,4?BAADA) in high yield and purity by hydrogenating the resulting 4,4?-DNDPA with a ketone in the presence of hydrogen and hydrogenation catalyst. The catalyst complex used in the present invention allows easy recovery, provides superior alkaline stability and is capable of reducing production cost.
    Type: Grant
    Filed: June 17, 2011
    Date of Patent: September 16, 2014
    Assignee: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Jin-Eok Kim, Seoung-IL Kim, Han Jin Kwag, Sang hee Park
  • Patent number: 8759588
    Abstract: The invention provides a process for producing xylylenediamine, including supplying a solution of phthalonitrile dissolved in a solvent to a reactor filled with a catalyst and hydrogenating the phthalonitrile to produce xylylenediamine, characterized in that the process includes halting supply of the solution; (2) bringing a washing liquid into contact with the catalyst, the washing liquid having a phthalonitrile content of 3 mass % or less and a xylylenediamine content of 1 mass % or more; and after completion of the contact, resuming supply of the solution, and employing the catalyst continuously in hydrogenation. Through the production process of the invention, the catalyst can be employed continuously for a long period of time, and the catalyst-related cost can be considerably reduced.
    Type: Grant
    Filed: August 27, 2009
    Date of Patent: June 24, 2014
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Shinichi Nagao, Tatsuyuki Kumano, Kenji Nakaya, Ryusuke Shigematsu, Kinji Kato
  • Patent number: 8759587
    Abstract: Provided is a method of preparing 4,4?-dinitrodiphenylamine (4,4?-DNDPA) in high yield by reacting 4-nitroaniline with excess nitrobenzene via the NASH reaction, and a method of preparing 4,4?-bis(alkylamino)diphenylamine (4,4?BAADA) in high yield and purity by hydrogenating the resulting 4,4?-DNDPA with a ketone compound in the presence of hydrogen and hydrogenation catalyst. The disclosed process is simple, allows selective preparation of 4,4?-DNDPA without byproducts, and thus allows preparation of 4,4?-BAADA in high yield without a complicated purification procedure.
    Type: Grant
    Filed: June 17, 2011
    Date of Patent: June 24, 2014
    Assignee: Korea Kumho Petrochemical Co., Ltd.
    Inventors: Jin-Eok Kim, Seoung-Il Kim, Han Jin Kwag, Sang hee Park
  • Patent number: 8614355
    Abstract: The invention relates to a catalyst and to a process for hydrogenating organic compounds. In particular, the invention is directed to a process and catalyst for hydrogenating organic compounds with hydrogen. The organic compounds are subjected to hydrogenation in the presence of a catalyst comprising nitrogen-doped carbon nanotubes as a catalytically active component, wherein the proportion of nitrogen in the nanotubes is in the range of from about 0.05 to 20 wt. %.
    Type: Grant
    Filed: June 3, 2009
    Date of Patent: December 24, 2013
    Assignee: Bayer Technology Services GmbH
    Inventors: Aurel Wolf, Volker Michele, Jens Aβmann, Leslaw Mleczko
  • Patent number: 8614356
    Abstract: A process for preparing tolylenediamine by hydrogenating dinitrotoluene with hydrogen in the presence of a suspended catalyst in a vertically upright reactor (1), at the upper end of which is arranged a motive jet nozzle (2) through which the reaction mixture drawn off from the reactor bottom, via an external loop, is sprayed into the upper region of the reactor (1) and then flows into a central inserted tube (4) which is arranged in the longitudinal direction of the reactor, flows through the latter from the top downward and flows upward again outside the inserted tube (4) in an internal loop motion, with a heat exchanger (6) in the interior of the reactor (1), through which cooling water flows, and absorbs some of the heat of reaction as it does so, with a feed for the dinitrotoluene at the upper end of the reactor (1) and a feed for the hydrogen at the lower end of the reactor (1), and wherein, in addition to the heat exchanger (6) arranged in the interior of the reactor (1), a further heat exchanger (W
    Type: Grant
    Filed: December 21, 2009
    Date of Patent: December 24, 2013
    Assignee: BASF SE
    Inventors: Joana Coelho Tsou, Steffen Oehlenschlaeger, Ekkehard Schwab, Wolfgang Mackenroth, Hartwig Voss, Stefan Maixner, Samuel Neto, Sven Boehmeke, Frederik Van Laar
  • Patent number: 8609899
    Abstract: The invention relates to a process for the continuous preparation of toluenediamine by liquid-phase hydrogenation of dinitrotoluene by means of hydrogen in the presence of a suspended, nickel-comprising catalyst in a reactor with a product isolation unit downstream of the reactor to give a product output from the reactor comprising a liquid phase comprising toluenediamine and dinitrotoluene, in which the nickel-comprising catalyst is suspended, wherein the concentration of dinitrotoluene in the liquid phase of the product output from the reactor in the region between the reactor and the downstream product isolation unit is set to a value in the range from 1 to 200 ppm by weight, based on the total weight of the liquid phase of the product output from the reactor.
    Type: Grant
    Filed: May 17, 2011
    Date of Patent: December 17, 2013
    Assignee: BASF SE
    Inventors: Andreas Raichle, Joana Coelho Tsou, Samuel Neto, Ulrich Penzel, Steffen Oehlenschlaeger, Michael Zoellinger, Holgar Braunsberg, Stefanie Haase, Johannes Buettner
  • Publication number: 20130204032
    Abstract: Process for the optical resolution of the compound of formula (I): by chiral chromatography. Application in the synthesis of ivabradine, of its addition salts with a pharmaceutically acceptable acid and of their hydrates.
    Type: Application
    Filed: March 26, 2013
    Publication date: August 8, 2013
    Applicant: Les Laboratoires Servier
    Inventor: Les Laboratoires Servier
  • Publication number: 20130197234
    Abstract: The present invention relates to methods for producing an optically active amine compound via a highly enantioselective hydrogenation reaction of an imine compound, wherein the imine compound is hydrogenated using a ruthenium metal complex having high catalytic activity and represented by Formula (1) RuXYAB??(1) such as RuBr2[(S,S)-xylskewphos][(S,S)-dpen].
    Type: Application
    Filed: February 1, 2013
    Publication date: August 1, 2013
    Applicants: National University Corporation Hokkaido University, Kanto Kagaku Kabushiki Kaisha
    Inventors: Kanto Kagaku Kabushiki Kaisha, National University Corporation Hokkaido University
  • Publication number: 20130158276
    Abstract: Provided is a catalyst for asymmetric reduction, which can be produced by a convenient and safe production method, has a strong catalytic activity, and has excellent stereoselectivity. The present invention relates to a ruthenium complex represented by the following formula (1): wherein R1 represents an alkyl group or the like; Y represents a hydrogen atom; X represents a halogen atom or the like; j and k each represent 0 or 1; R2 and R3 each represent an alkyl group or the like; R11 to R19 each represent a hydrogen atom, an alkyl group or the like; Z represents oxygen or sulfur; n1 represents 1 or 2; and n2 represents an integer from 1 to 3, a method for producing the ruthenium complex, a catalyst for asymmetric reduction formed from the ruthenium complex, and methods for selectively producing an optically active alcohol and an optically active amine using the catalyst for asymmetric reduction.
    Type: Application
    Filed: June 17, 2011
    Publication date: June 20, 2013
    Applicant: TAKASAGO INTERNATIONAL CORPORATION
    Inventors: Taichiro Touge, Hideki Nara, Tomohiko Hakamada
  • Publication number: 20130150623
    Abstract: An object is to provide a process for providing hydrogen or heavy hydrogens conveniently without the necessity of large-scale equipment and a process capable of performing hydrogenation (protiation, deuteration or tritiation) reaction conveniently without the use of an expensive reagent and a special catalyst. The production process includes a process for producing hydrogen or heavy hydrogens, containing subjecting water or heavy water to mechanochemical reaction in the presence of a catalyst metal, and a process for producing a hydrogenated (protiated, deuterated or tritiated) organic compound, containing subjecting an organic compound and water or heavy water to mechanochemical reaction in the presence of a catalyst metal.
    Type: Application
    Filed: August 16, 2011
    Publication date: June 13, 2013
    Applicant: Shiono Chemical Co., Ltd.
    Inventors: Hironao Sajiki, Yasunari Monguchi, Yoshinari Sawama, Shinichi Kondo
  • Patent number: 8461386
    Abstract: The present invention relates to a process for the asymmetric hydrogenation of imines with hydrogen under elevated pressure in the presence of a catalyst system. In particular the present invention relates to the use of the said catalytic system for the enantioselective hydrogenation of prochiral ketimines to asymmetric amines leading to the formation of herbicides.
    Type: Grant
    Filed: April 16, 2009
    Date of Patent: June 11, 2013
    Assignee: United Phosphorus Limited
    Inventors: Jaidev Rajnikant Shroff, Vikram Rajnikant Shroff, Birja Shanker
  • Patent number: 8420862
    Abstract: Highly pure 2,3,5,6-tetraaminotoluene species are produced by chemically reducing undesirable oxidation byproducts. The 2,3,5,6-tetraaminotoluene species are then used in the manufacture of superior high-performance polybenzimidazole polymers.
    Type: Grant
    Filed: December 10, 2009
    Date of Patent: April 16, 2013
    Assignee: E I du Pont de Nemours and Company
    Inventors: Rajiv Dhawan, Joachim C. Ritter
  • Publication number: 20130072722
    Abstract: The present invention relates to supported metal catalysts, wherein the catalysts are modified by at least one amine, a method for the preparation thereof and hydrogenation processes utilising the supported metal catalysts.
    Type: Application
    Filed: February 17, 2011
    Publication date: March 21, 2013
    Applicant: JOHNSON MATTHEY PUBLIC LIMITED COMPANY
    Inventors: Peter Trenton Bishop, James Cookson, Frederick Earnest Hancock, Steven Hawker, Robert John McNair
  • Patent number: 8354558
    Abstract: Diastereoselective conversion of chiral imines of the formula I to amines of the formula II where the R1 to R4 radicals are each as defined in the description and R1 and R2 are different than one another, by converting the imine of the formula I in the presence of hydrogen and a heterogeneous copper-containing catalyst.
    Type: Grant
    Filed: December 10, 2008
    Date of Patent: January 15, 2013
    Assignee: BASF SE
    Inventors: Wolfgang Siegel, Thilo Hahn, Tobias Staeb
  • Patent number: 8329950
    Abstract: One aspect of the present invention relates to pharmaceutical compositions containing two or more active agents that when taken together can be used to treat, e.g., menopause, mood disorders, anxiety disorders, or cognitive disorders. The first component of the pharmaceutical composition is a sedative eszopiclone. The second component of the pharmaceutical composition is trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-napthalenamine or trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthalenamine. The present invention also relates to a method of treating menopause, perimenopause, mood disorders, anxiety disorders, and cognitive disorders.
    Type: Grant
    Filed: January 25, 2012
    Date of Patent: December 11, 2012
    Assignee: Sunovion Pharmaceuticals Inc.
    Inventors: Judy Caron, Thomas Wessel, Karim Lalji, Mark Varney, Roger P. Bakale, Surendra P. Singh, H. Scott Wilkinson, Xiping Su, Zhengxu Han, Stefan G. Koenig
  • Patent number: 8258345
    Abstract: The present invention pertains to a process for preparing a compound of Formula I that is achiral, racemic or enantiomerically enriched at the hydroxylation center indicated by * comprising contacting a compound of Formula II with an oxidant selected from oxygen, hydrogen peroxide, peracids or alkyl hydroperoxides in the presence of a zirconium complex, wherein R1, R2 and R3 are as defined in the disclosure. This invention also pertains to zirconium complexes useful in this procedure comprising zirconium and a ligand of Formula III or its enantiomer wherein J, R6 and n are as defined in the disclosure. This invention further pertains to a compound of Formula III or its enantiomer.
    Type: Grant
    Filed: March 16, 2011
    Date of Patent: September 4, 2012
    Assignee: E I du Pont de Nemours and Company
    Inventor: Albert Loren Casalnuovo
  • Patent number: 8188317
    Abstract: An integrated process is provided for preparing complexes of 2,3,5,6-tetraminotoluene with an aromatic diacid starting with nitration of 2,6-dihalotoluene. The process design eliminates costly intermediate drying and recrystallization steps. Handling of solid materials with possible skin sensitizing properties and toxicity is avoided, thereby eliminating human and environmental exposure.
    Type: Grant
    Filed: December 10, 2009
    Date of Patent: May 29, 2012
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Rajiv Dhawan, Joachim C. Ritter
  • Patent number: 8188316
    Abstract: Processes are provided for preparing complexes of 2,3,5,6-tetraaminotoluene with an aromatic diacid where the aromatic diacid is insoluble in water under ambient conditions. An integrated process design starting with nitration of 2,6-dihalotoluene eliminates costly intermediate drying and recrystallization steps. Handling of solid materials with possible skin sensitizing properties and toxicity is avoided, thereby eliminating human and environmental exposure.
    Type: Grant
    Filed: December 10, 2009
    Date of Patent: May 29, 2012
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Rajiv Dhawan, Joachim C. Ritter
  • Publication number: 20120123164
    Abstract: One aspect of the present invention relates to pharmaceutical compositions containing two or more active agents that when taken together can be used to treat, e.g., menopause, mood disorders, anxiety disorders, or cognitive disorders. The first component of the pharmaceutical composition is a sedative eszopiclone. The second component of the pharmaceutical composition is trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-1-napthalenamine or trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthalenamine. The present invention also relates to a method of treating menopause, perimenopause, mood disorders, anxiety disorders, and cognitive disorders.
    Type: Application
    Filed: January 25, 2012
    Publication date: May 17, 2012
    Applicant: SUNOVION PHARMACEUTICALS INC.
    Inventors: Judy CARON, Thomas Wessel, Karim Lalji, Mark A. Varney, Roger P. Bakale, Surendra P. Singh, H. Scott Wilkinson, Xiping Su, Zhengxu Steve Han, Stefan G. Koenig
  • Patent number: 8163955
    Abstract: An improved process is provided for the preparation of 2,6-diamino-3,5-dinitrotoluene by amination of 2,6-dichloro-3,5-dinitrotoluene. The presence of water unexpectedly results in a highly pure product, free of glycol ether impurities. This product can be used to make highly pure 2,3,5,6-tetraaminotoluene, which in turn can be used to make high molecular weight polybenzimidazoles for high strength fibers.
    Type: Grant
    Filed: December 10, 2009
    Date of Patent: April 24, 2012
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Rajiv Dhawan, Joachim C. Ritter
  • Patent number: 8163961
    Abstract: Complexes of 2,3,5,6-tetraaminotoluene with an aromatic diacid are prepared by reaction with a divalent salt of the aromatic diacid while maintaining the pH of the reaction solution between 3 and 10. The resulting complexes are suitable for making high molecular weight polybenzimidazole polymers for high-performance fibers.
    Type: Grant
    Filed: February 22, 2010
    Date of Patent: April 24, 2012
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Rajiv Dhawan, Joachim C. Ritter
  • Patent number: 8158830
    Abstract: An integrated process is provided for preparing 1,2,4,5-tetraminobenzene and salts thereof, starting in certain embodiments with nitration of 1,3-dihalobenzene. The process design eliminates costly intermediate drying and recrystallization steps. Handling of solid materials with possible skin sensitizing properties and toxicity is avoided, thereby eliminating human and environmental exposure.
    Type: Grant
    Filed: December 17, 2008
    Date of Patent: April 17, 2012
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Joachim C. Ritter, Ekaterini Korovessi, Rajiv Dhawan
  • Publication number: 20110313199
    Abstract: Provided herein are improved, convenient and industrially advantageous processes for the preparation of N-[2-hydroxy-5-[(1R)-1-hydroxy-2-[[(1R)-2-(4-methoxyphenyl)-1-methylethyl]amino]ethyl]phenyl]formamide (Arformoterol) or a pharmaceutically acceptable salt thereof, in high yield and purity. Provided further herein is an improved and industrially advantageous process for the preparation of a substantially enantiomerically pure arformoterol intermediate, (R)-4-methoxy-?-methyl-N-(phenylmethyl)benzeneethanamine.
    Type: Application
    Filed: December 28, 2009
    Publication date: December 22, 2011
    Applicant: ACTAVIS GROUP PTC EHF
    Inventors: Girish Dixit, Nandkumar Gaikwad, Nitin Sharadchandra Pradhan
  • Patent number: 8071812
    Abstract: A process is provided for the preparation of 1,3-diamino-4,6-dinitrobenzene by amination of 1,3-dihalo-4,6-dinitrobenzene. The presence of water advantageously results in a highly pure product, free or essentially free of glycol ether impurities.
    Type: Grant
    Filed: December 16, 2008
    Date of Patent: December 6, 2011
    Assignee: E.I du Pont de Nemours & Company
    Inventors: Joachim C. Ritter, Annalisa Hargis
  • Publication number: 20110245540
    Abstract: The invention provides a process for producing xylylenediamine, including supplying a solution of phthalonitrile dissolved in a solvent to a reactor filled with a catalyst and hydrogenating the phthalonitrile to produce xylylenediamine, characterized in that the process includes halting supply of the solution; (2) bringing a washing liquid into contact with the catalyst, the washing liquid having a phthalonitrile content of 3 mass % or less and a xylylenediamine content of 1 mass % or more; and after completion of the contact, resuming supply of the solution, and employing the catalyst continuously in hydrogenation. Through the production process of the invention, the catalyst can be employed continuously for a long period of time, and the catalyst-related cost can be considerably reduced.
    Type: Application
    Filed: August 27, 2009
    Publication date: October 6, 2011
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Shinichi Nagao, Tatsuyuki Kumano, Kenji Nakaya, Ryusuke Shigematsu, Kinji Kato
  • Publication number: 20110196175
    Abstract: The present invention pertains to a process for preparing a compound of Formula I that is achiral, racemic or enantiomerically enriched at the hydroxylation center indicated by * comprising contacting a compound of Formula II with an oxidant selected from oxygen, hydrogen peroxide, peracids or alkyl hydroperoxides in the presence of a zirconium complex, wherein R1, R2 and R3 are as defined in the disclosure. This invention also pertains to zirconium complexes useful in this procedure comprising zirconium and a ligand of Formula III or its enantiomer wherein J, R6 and n are as defined in the disclosure. This invention further pertains to a compound of Formula III or its enantiomer.
    Type: Application
    Filed: March 16, 2011
    Publication date: August 11, 2011
    Inventor: Albert Loren Casalnuovo
  • Publication number: 20110077418
    Abstract: A process is provided for the hydrogenation of imines with hydrogen under elevated pressure in the presence of iridium complexes as catalysts and one or more co-catalysts selected among compounds comprising a carbon-halogen bond. Further provided are novel ligands and metal complexes thereof useful for the catalytic hydrogenation of imines with hydrogen. The novel ligands are compounds of the formula (VII) or formula (VIII) in the form of racemates, mixtures of stereoisomers or optically pure stereoisomers wherein the radicals are as defined in the specification.
    Type: Application
    Filed: September 25, 2009
    Publication date: March 31, 2011
    Applicant: CHEMINOVA A/S
    Inventors: Steen Saaby, Ib Winckelmann, Kaare Sondergaard, Xianmiao Liang, Yanxiong Ke, Xinliang Wang, Jinxing Ye
  • Patent number: 7795472
    Abstract: A process for the industrial production of 2-amino-2-[2-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]ethyl]-1,3-propanediol hydrochloride (Compound I), an effective immunosuppressant. The process for producing 2-amino-2-[2-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]ethyl]-1,3-propanediol hydrochloride or a hydrate thereof includes the steps of reacting 4-(3-benzyloxyphenylthio)-2-chlorobenzaldehyde with ethyl diethylphosphonoacetate in a solvent in the presence of a base to form ethyl 3-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]acrylate; reducing the resulting ethyl 3-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]acrylate, followed by mesylation, iodination and nitration, to form 1-benzyloxy-3-[3-chloro-4-(3-nitropropyl)phenylthio]benzene; forming 2-[2-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]ethyl]-2-nitro-1,3-propanediol using a formaldehyde solution; and reducing the resulting 2-[2-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]ethyl]-2-nitro-1,3-propanediol to form the desired product.
    Type: Grant
    Filed: October 7, 2005
    Date of Patent: September 14, 2010
    Assignee: Kyorin Pharmaceutical Co., Ltd.
    Inventors: Takeshi Tsubuki, Kenichi Kobayashi, Hidetaka Komatsu
  • Patent number: 7781615
    Abstract: The present invention relates to a novel a process for the preparation of the compound of the general formula (I), wherein R1 and R2 are independently H or C1-6 alkyl, which comprises treating with a reducing agent either a compound of the general formula (II), wherein R1 and R2 have the meanings given for the compound of the formula (I), R3 is H or C1-4alkyl and Ph is phenyl, or a compound of the general formula (III), wherein R1, R2, R3 and Ph have the meanings given for the compound of the formula (II), the reducing agent being effective to cleave the benzyl moiety Ph-CH(R3)— from the benzylamino moiety PhCH(R3)NH— in the compound of the formula (II) or in the compound of the formula (III) to leave an amino group and, in addition, in the case of the compound of the formula (III), to reduce both the 2,3-double bond and the double bond joining the R1R2C— moiety to the 9-position of the benzonorbornene ring to single bonds.
    Type: Grant
    Filed: December 11, 2006
    Date of Patent: August 24, 2010
    Assignee: Syngenta Crop Protection, Inc.
    Inventors: Hans Tobler, Harald Walter, Camilla Corsi, Josef Ehrenfreund, Fanny Giordano, Martin Zeller
  • Patent number: 7737301
    Abstract: The present invention relates to a process for the preparation of compounds of formula wherein R1, R2 and R3 are each independently of the others hydrogen or C1-C4alkyl, by a) reacting compounds of formula (II) wherein R1, R2 and R3 are as defined for formula (I) and X is bromine or chlorine, with a compound of formula (III) wherein R4 is hydrogen or C1-C4alkyl, in the presence of a base and catalytic amounts of at least one palladium complex compound, to form compounds of formula (IV) wherein R1, R2, R3 and R4 are as defined for formula (I), and b) converting those compounds, using a reducing agent, into compounds of formula (I).
    Type: Grant
    Filed: August 28, 2006
    Date of Patent: June 15, 2010
    Assignee: Syngenta Crop Protection, Inc.
    Inventors: Harald Walter, Camilla Corsi, Josef Ehrenfreund, Hans Tobler
  • Patent number: 7626057
    Abstract: A method of producing xylylenediamine by a two-stage hydrogenation of a starting phthalonitrile in a solvent. The main steps of the method are a hydrogenation step 1 and a hydrogenation step 2. In the hydrogenation step 1, a solution of the starting phthalonitrile in the solvent containing liquid ammonia is fed to an inlet of a first reaction zone and the hydrogenation is carried out in the first reaction zone in the presence of a heterogeneous catalyst, to hydrogenate nitrile groups in the starting phthalonitrile to aminomethyl groups. A part of the hydrogenation product solution from the first reaction zone is circulated to the inlet of the first reaction zone and the rest is introduced into the hydrogenation step 2 where further undergoes the hydrogenation.
    Type: Grant
    Filed: June 27, 2007
    Date of Patent: December 1, 2009
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Tatsuyuki Kumano, Ryusuke Shigematsu, Kinji Kato, Kenji Nakaya
  • Patent number: 7592488
    Abstract: The present invention relates to a method of preparing optically active amines and chiral amines prepared thereby. The method includes reacting an amine compound, a metal catalyst, a biocatalyst including a lipase, and an acyl donor compound in an organic solvent to obtain a chiral amide compound, and then hydrolyzing the chiral amide compound to obtain a chiral amine.
    Type: Grant
    Filed: August 18, 2007
    Date of Patent: September 22, 2009
    Assignee: Postech Academy-Industry Foundation
    Inventors: Mahn-Joo Kim, Jaiwook Park, Won-Hee Kim, Kiwon Han, Yoon Kyung Choi
  • Patent number: 7588721
    Abstract: A solid xylylenediamine solidified in a container is extremely excellent in storage stability as compared with a liquid xylylenediamine, and is less degraded by discoloration even when stored in an atmosphere containing oxygen. By charging a liquid xylylenediamine into a container, solidifying the liquid xylylenediamine into a solid xylylenediamine in the container under cooling without delay after the charging, and storing the solid xylylenediamine in the container while maintaining the xylylenediamine in a solid state, the xylylenediamine is stored for a long period of time without causing deterioration of quality such as discoloration.
    Type: Grant
    Filed: August 29, 2007
    Date of Patent: September 15, 2009
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Kazumi Tanaka, Kazuhiko Amakawa
  • Patent number: 7528284
    Abstract: A process for preparing xylylenediamine, comprising the steps of ammoxidizing xylene to phthalonitrile and hydrogenating the phthalonitrile, which comprises contacting the vaporus product of the ammoxidation stage directly with a liquid organic solvent or with molten phthalonitrile (quench), partly or fully removing components having a boiling point lower than phthalonitrile (low boilers) from the resulting quench solution or suspention or phthalonitrile melt and, before the hydrogenation, of the phthalonitrile, not removing any products having a boiling point higher than phthalonitrile (high boilers).
    Type: Grant
    Filed: September 4, 2004
    Date of Patent: May 5, 2009
    Assignee: BASF Aktiengesellschaft
    Inventors: Randolf Hugo, Sabine Jourdan, Kirsten Wenz, Thomas Preiss, Alexander Weck
  • Publication number: 20080293972
    Abstract: Disclosed is a process for preparing substituted anisidines of formula I starting from substituted cyclic hydroxy-ketones II via aromatization through a substituted oxime intermediate IV in which R is C1-C6 alkyl or halogen, and Alk is C1-C6 alkyl. The substituted anisidines of formula I have been found to be useful as intermediates in the preparation of agents for the treatment of hepatitis C viral (HCV) infections.
    Type: Application
    Filed: November 1, 2006
    Publication date: November 27, 2008
    Inventors: Fabrice Gallou, Heewon Lee, Chris Hugh Senanayake, Jinhua J. Song, Zhulin Tan, Jinghua Xu, Nathan K. Yee
  • Patent number: 7442794
    Abstract: The invention relates to the compounds of formula I, a process for their production and their use as anti-inflammatory agents.
    Type: Grant
    Filed: October 8, 2004
    Date of Patent: October 28, 2008
    Assignee: Schering AG
    Inventors: Hartmut Rehwinkel, Stefan Baeurle, Markus Berger, Norbert Schmees, Heike Schaecke, Konrad Krolikiewicz, Anne Mengel, Duy Nguyen, Stefan Jaroch, Werner Skuballa
  • Publication number: 20080262266
    Abstract: Process for preparing o-, m- or p-xylylenediamine by hydrogenation of o-, m- or p-phthalonitrile in the presence of a heterogenous catalyst, which comprises feeding a solution of the phthalonitrile in the corresponding isomer of crude xylylenediamine into the hydrogenation reactor, with the crude xylylenediamine having a purity in the range from 85 to 99.7% by weight and a content of higher boilers in the range from 0.3 to 15% by weight.
    Type: Application
    Filed: September 14, 2006
    Publication date: October 23, 2008
    Applicant: BASF SE
    Inventors: Kirsten Dahmen, Sabine Huber, Randolf Hugo, Johann-Peter Melder, Thomas Preiss
  • Patent number: 7381845
    Abstract: A process for hydrogenating nitrile functions present in organic compounds over at least one heterogeneous catalyst, in which the hydrogenation is carried out in the presence of an ionic liquid, is described.
    Type: Grant
    Filed: December 20, 2004
    Date of Patent: June 3, 2008
    Assignee: BASF Aktiengesellschaft
    Inventors: Verena Weiskopf, Till Gerlach, Kirsten Wenz
  • Patent number: 7368610
    Abstract: A process for preparing xylylenediamine, comprising the steps of ammoxidizing xylene to phthalonitrile and hydrogenating the phthalonitrile, which comprises contacting the vaporous product of the ammoxidation stage directly with a liquid organic solvent or with molten phthalonitrile (quench), partly or fully removing components having a boiling point lower than phthalonitrile (low boilers) from the resulting quench solution or suspension or phthalonitrile melt and, after the low boiler removal and before the hydrogenation, removing products having a boiling point higher than phthalonitrile (high boilers).
    Type: Grant
    Filed: September 4, 2004
    Date of Patent: May 6, 2008
    Assignee: BASF Aktiengesellschaft
    Inventors: Randolf Hugo, Sabine Jourdan, Kirsten Wenz, Thomas Preiss, Alexander Weck
  • Patent number: 7339080
    Abstract: A process for preparing xylylenediamine by continuously hydrogenating liquid phthalonitrile over a heterogeneous catalyst in the presence of liquid ammonia in a reactor, which comprises mixing a stream of a phthalonitrile melt in liquid form by means of a mixer unit with a stream of liquid ammonia and conducting the liquid mixture into the hydrogenation reactor.
    Type: Grant
    Filed: September 9, 2004
    Date of Patent: March 4, 2008
    Assignee: BASF Aktiengesellschaft
    Inventors: Randolf Hugo, Kirsten Wenz, Rolf Wambsganβ, Sabine Jourdan, Thomas Preiss
  • Patent number: 7323598
    Abstract: A process for preparing xylylenediamine, comprising the steps of ammoxidizing xylene to phthalonitrile by contacting the vaporous product of this ammoxidation stage directly with a liquid organic solvent (quench), removing products having a boiling point higher than phthalonitrile (high boilers) from the resulting quench solution or suspension and hydrogenating the phthalonitrile, wherein the organic solvent used for the quench is N-methyl-2-pyrrolidone (NMP), after the removal of the high boilers and before the hydrogenation, there is a partial or complete removal of the NMP and/or of products having a boiling point lower than phthalonitrile (low boilers) and the phthalonitrile for the hydrogenation step is dissolved or suspended in an organic solvent or in liquid ammon.
    Type: Grant
    Filed: September 4, 2004
    Date of Patent: January 29, 2008
    Assignee: BASF Aktiengesellschaft
    Inventors: Randolf Hugo, Sabine Jourdan, Kirsten Wenz, Thomas Preiss, Alexander Weck
  • Publication number: 20070270613
    Abstract: A method of producing xylylenediamine of the present invention includes the steps of: subjecting a liquid mixture of phthalonitriles with liquid ammonia or a mixture of liquid ammonia and an organic solvent to a first catalytic hydrogenation treatment, thereby hydrogenating the phthalonitriles to obtain a reaction product (A), wherein a content of the liquid ammonia or the mixture of liquid ammonia and an organic solvent is 80 wt % or more; removing the liquid ammonia in the reaction product (A) to obtain a reaction product (B); subjecting the reaction product (B) to a second catalytic hydrogenation treatment, thereby hydrogenating cyanobenzylamine to obtain a reaction product (C); and distilling the reaction product (C) to purify xylylenediamine.
    Type: Application
    Filed: May 17, 2007
    Publication date: November 22, 2007
    Inventors: Tomohiro Sugawara, Takafumi Abe, Tatsuyuki Kumano, Kinji Kato
  • Patent number: 7291754
    Abstract: Process for the catalytic hydrogenation of a nitrite in the presence of an amine and a catalyst wherein the catalyst is a liquid-rinsed Raney-type catalyst contacted with a hydroxide prior to contacting the catalyst with the amine. The process results in higher selectivity in the formation of diamines from diniriles.
    Type: Grant
    Filed: January 21, 2004
    Date of Patent: November 6, 2007
    Assignee: DSM IP Assets B.V.
    Inventors: Franciscus H. A. M. Vandenbooren, Hubertus J. M. Bosman, Alexander V. Peters, Maria J. G. Van Den Boer
  • 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
  • Patent number: 7256312
    Abstract: The invention relates to a process for preparing 4-[aminoalkoxy]benzylamines of the general formula (I) by catalytically hydrogenating 4-[aminoalkoxy]benzonitriles of the general formula (II) where, in the compounds of the general formulae I and II, R1 is C1-C8-alkylene, R2 and R3 are each independently C1-C8-alkyl or are joined to give a ring which may additionally contain a heteroatom, which comprises carrying out the hydrogenation at elevated pressure and elevated temperatures. The invention further relates to a process for preparing the intermediate (II).
    Type: Grant
    Filed: July 18, 2003
    Date of Patent: August 14, 2007
    Assignee: BASF Aktiengesellschaft
    Inventors: Oliver Löber, Christoph Benisch, Klaus Ebel, Johann-Peter Melder
  • Patent number: 7256311
    Abstract: A process is provided for the hydrogenation or asymmetric hydrogenation of dialkyl, alkylalkenyl and dialkenyl imines of formula (II) to provide amines of formula (III), wherein, (i) R1 and R2 are optionally substituted cyclic, linear or branched alkyl or alkenyl; R3 is a hydrogen atom, a hydroxy radical, optionally substituted C1 to C8 cyclic, linear or branched alkyl or alkenyl, optionally substituted aryl; or (ii) R1 is alkyl or alkenyl, R2 is alkyl or alkenyl and the two are linked together or with R3 to form one or more rings; using a catalytic system comprising a base and a ruthenium complex containing (1) a diamine and (2) a diphosphine ligand or monodentate phosphine ligands in hydrogenation and asymmetric hydrogenation processes
    Type: Grant
    Filed: May 15, 2003
    Date of Patent: August 14, 2007
    Inventors: Kamaluddin Abdur-Rashid, Robert H. Morris
  • Patent number: 7244860
    Abstract: Compounds of the formula (I), in which R1 is C1-C4alkyl, C6-C10aryi or C7-C11, aralkyl, R2 is an open-chain or cyclic secondary amino group, and R is a radical of the formula in which R3 is C1-C4alkyl or C1-C4alkoxy, and R4 is H, C1-C4alkyl or C1-C4alkoxy, are ligands for metal complexes as homogeneous hydrogenation catalysts for prochiral organic compounds containing double bonds, by means of which a very high activity and productivity and also enantioselectivity can be achieved
    Type: Grant
    Filed: May 7, 2004
    Date of Patent: July 17, 2007
    Assignee: Umicore AG & Co. KG
    Inventors: Felix Spindler, Matthias Lotz, Marc Thommen
  • Patent number: 7196223
    Abstract: A nitrile-containing mixture, which includes a nitrile dissolved in a higher alcohol solvent, and hydrogen are fed to a reactor containing a catalyst. An amine is produced by hydrogenating the nitrile that is dissolved in the higher alcohol solvent. In a preferred embodiment, the reactor also contains a caustic solution. The preferred nitrile-containing mixture includes octadecaneditrile (ODDN) and hexanol to produce a preferred octadecanediamine (ODDA) through hydrogenation.
    Type: Grant
    Filed: May 3, 2005
    Date of Patent: March 27, 2007
    Assignee: Solutia, Inc.
    Inventors: Tom L. Flowers, Anthony K. Uriarte, Shannon Davis, Gregory J. Ward