Forming Amine Group Directly By Reduction, Other Than By Reductive Amination Patents (Class 564/385)
  • Patent number: 10875824
    Abstract: A nickel diatomaceous earth catalyst having a weight loss rate measured by hydrogen-TG at 400 to 600° C. of 0.05 to 2.0%.
    Type: Grant
    Filed: September 18, 2019
    Date of Patent: December 29, 2020
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Kouji Suzuki, Hajime Yamada
  • Patent number: 9878314
    Abstract: A catalyst for producing isoparaffins-rich synthetic oil is a granulated porous composite material comprising a three-dimensional heat-conducting structure of metal aluminum and Raney cobalt, and a binding component comprising an H-form zeolite. The particles of Raney cobalt and zeolite are in mutual direct contact. Fractions of macropores in an open porosity of the catalyst granules and of mesopores of the size of 70-500 ? in an open porosity of the catalyst granules are respectively 55-79% and 7-20%, a fraction of micropores being the rest. A method for preparing the catalyst comprises mixing binding component powders, peptizing the mixture with a nitric acid solution, mixing obtained homogeneous gel with powders of Raney cobalt and metal aluminum and a liquid phase to form a paste, extruding same into granules and calcinating the granules. The catalyst improves reagents mass transfer inside the granules and increases isoparaffine content in the produced oil.
    Type: Grant
    Filed: November 26, 2013
    Date of Patent: January 30, 2018
    Assignee: Infra XTL Technology Ltd.
    Inventors: Vladimir Z. Mordkovich, Lilia V. Sineva, Ekaterina Yu Khatkova, Ilia S. Ermolaev
  • Patent number: 9365494
    Abstract: Methods for producing a compound of formula k1 or k2 by reducing a dihydronapthalene amide compound of formula i with hydrogen gas in the presence of a ruthenium catalyst of formula j1 or j2 Ru(Z)2(L)??j1; Ru(E)(E?)(L)(D)??j2; wherein m, n, Ar, Y, R1E, E?, D, Z and L are as defined herein.
    Type: Grant
    Filed: January 26, 2012
    Date of Patent: June 14, 2016
    Assignee: Roche Palo Alto LLC
    Inventors: Kieran Durkin, Lawrence Emerson Fisher, Arthur Meili, Michaelangelo Scalone, Xianqing Shi, Justin Vitale
  • Patent number: 9196839
    Abstract: There is provided an organic compound of excellent characteristics that exhibits excellent hole-injecting/transporting performance and has an electron blocking ability and a highly stable thin-film state with excellent heat resistance. The compound of the present invention is an arylamine compound having a triphenylamine structure. The arylamine compound is used as a constituent material of at least one organic layer in an organic electroluminescent device that includes a pair of electrodes, and one or more organic layers sandwiched between the pair of electrodes.
    Type: Grant
    Filed: January 25, 2011
    Date of Patent: November 24, 2015
    Assignee: Hodogaya Chemical Co., Ltd.
    Inventors: Norimasa Yokoyama, Makoto Nagaoka, Kouki Kase, Shingo Ozawa, Shigeru Kusano
  • Patent number: 9181156
    Abstract: The present invention relates to an apparatus for producing alcohols from olefins, comprising: a hydroformylation reactor wherein aldehydes are produced from olefins; a catalyst/aldehydes separator; a hydrogenation reactor wherein the aldehydes are hydrogenated to produce alcohols; and a distillation column. The hydroformylation reactor is equipped with a distributor plate, which has a broad contact surface for providing sufficient reaction area for reactants such as olefins and synthesis gas, and allows the reaction mixture to circulate and mix sufficiently, which contribute to excellent efficiency in terms of production of aldehydes. In addition, the hydrogenation reactor suppresses sub-reactions to improve the production yield of alcohols.
    Type: Grant
    Filed: October 23, 2013
    Date of Patent: November 10, 2015
    Assignee: LG Chem, Ltd.
    Inventors: Dong-Hyun Ko, Sung-Shik Eom, Yong-Jin Choe, Chan-Hong Lee, Moo-Ho Hong, O-Hak Kwon, Dae-Chul Kim, Jae-Hui Choi
  • Patent number: 9061969
    Abstract: A compound of formula (I) is disclosed: wherein definitions of R1, R2, and R3 are the same as those defined in the specification. The compound of formula (I) can emit light via an intramolecular interaction of an imino group and an electron-donatable moiety contained in the compound. A photoluminescent organic composition is also disclosed, which includes a compound represented by formula (II) in the presence of an electron-donatable compound, wherein definitions of R4, R5, and R6 are the same as those defined in the specification. The photoluminescent organic composition can emit light via an intermolecular interaction of an imino group contained in the compound of formula (II) and an electron-donatable moiety contained in the electron-donatable compound.
    Type: Grant
    Filed: November 4, 2011
    Date of Patent: June 23, 2015
    Assignee: I SHOU UNIVERSITY
    Inventors: Jau-Yann Wu, Pei-Ying Tsai, I-Hsiang Wang, Shi-Xuan Chou, Guan-Ru Pan, Shih-Han Wang, Ting-Fan Chou, Ming-Yao Huang, Yu-Cheng Wang
  • Publication number: 20140316163
    Abstract: Disclosed are compounds represented by structural formula (I): methods of producing compounds represented by structural formula (I). and their use in inhibiting oxidation in an oxidizable material.
    Type: Application
    Filed: April 17, 2014
    Publication date: October 23, 2014
    Applicant: Polnox Corporation
    Inventors: Rajesh Kumar, Suizhou Yang, Vijayendra Kumar, Ashok L. Cholli
  • Publication number: 20140275446
    Abstract: The present invention relates to hardeners for epoxy resins, which contain secondary aliphatic and primary aromatic amino groups. They harden surprisingly quickly together with epoxy resins even under cold and humid conditions and without blushing effects to give films with a high degree of hardness. They are especially suitable for coatings with high resistance requirements.
    Type: Application
    Filed: November 8, 2012
    Publication date: September 18, 2014
    Applicant: Sika Technology AG
    Inventors: Andreas Kramer, Edis Kasem
  • Patent number: 8642812
    Abstract: A compound having the formula (I) where each of R1, R2, R3 and R4 is independently C6-C18 aryl-, C5-C8 cycloalkyl-, C6-C18 aryl having at least one C1-C20 alkyl substituent, C5-C8 cycloalkyl having at least one C1-C20 alkyl substituent, C4-C20 branched alkyl-, C16-C20 linear alkyl-, RO—, —NRR?, —PRR?, —SR, fluoro substituted forms thereof, and perfluoro forms thereof: and R5 is C6-C18 aryl-, C3-C8 cycloalkyl-, C6-C18 aryl having at least one C1-C20 alkyl substituent, C5-C8 cycloalkyl having at least one C1-C20 alkyl substituent, C3-C20 branched alkyl-, C2-C30 linear alkyl-, fluoro substituted forms thereof, and perfluoro forms thereof; where R and R? are each independently C6-C18 aryl-, C5-C8 cycloalkyl-, C6-C18 aryl having at least one C1-C20 alkyl substituent, C5-C8 cycloalkyl having at least one C1-C20 alkyl substituent, C4-C20 branched alkyl-, C2-C30 linear alkyl-, fluoro substituted forms thereof, and perfluoro forms thereof; A is N, P, S, or O with the proviso that when A is S, R2 is a nullity; and M is
    Type: Grant
    Filed: September 14, 2012
    Date of Patent: February 4, 2014
    Assignee: Stephan Consulting Corporation
    Inventors: Douglas W. Stephan, Gregory C. Welch, Jenny S. J. McCahill
  • Publication number: 20130281664
    Abstract: The present invention relates to novel Ruthenium catalysts and related borohydride complexes, and the use of such catalysts, inter alia, for (1) hydrogenation of amides (including polyamides) to alcohols and amines; (2) preparing amides from alcohols with amines (including the preparation of polyamides (e.g., polypeptides) by reacting dialcohols and diamines and/or by polymerization of amino alcohols); (3) hydrogenation of esters to alcohols (including hydrogenation of cyclic esters (lactones) or cyclic di-esters (di-lactones) or polyesters); (4) hydrogenation of organic carbonates (including polycarbonates) to alcohols and hydrogenation of carbamates (including polycarbamates) or urea derivatives to alcohols and amines; (5) dehydrogenative coupling of alcohols to esters; (6) hydrogenation of secondary alcohols to ketones; (7) amidation of esters (i.e.
    Type: Application
    Filed: October 11, 2011
    Publication date: October 24, 2013
    Inventors: David Milstein, Ekambaram Balaraman, Chidambaram Gunanathan, Boopathy Gnanaprakasam, Jing Zhang
  • Patent number: 8563753
    Abstract: The present invention relates to a catalyst system. In particular the invention relates to a catalyst in the form of metal or an alloy that is encapsulated within a polymer shell or matrix. More specifically the invention is directed towards reactive catalytic metals that may be pyrophoric or otherwise reactive in air and/or susceptible to oxidation. In particular, the invention is concerned with catalysts based on nickel.
    Type: Grant
    Filed: February 12, 2010
    Date of Patent: October 22, 2013
    Inventors: Thomas Eric Oliver Screen, Mohammed Nisar
  • Publication number: 20130217910
    Abstract: The present invention relates to a process for the preparation of substituted N-(benzyl)cyclopropanamines of the general formula (II) starting from N-[(aryl)methylene]cyclopropanamine derivatives. The present invention further provides the N-[(arypmethylene]cyclopropanamine derivatives used as starting compounds in this process according to the invention, and their use for the preparation of substituted N (benzyl)cyclopropanamines.
    Type: Application
    Filed: November 4, 2011
    Publication date: August 22, 2013
    Inventors: Norbert Lui, Wahed Ahmed Moradi, Thomas Norbert Muller
  • 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: 20130149244
    Abstract: The present invention generally relates to novel synthetic methods, systems, kits, salts, and precursors useful in medical imaging. In some embodiments, the present invention provides compositions comprising an imaging agent precursor, which may be formed using the synthetic methods described herein. An imaging agent may be converted to an imaging agent using the methods described herein. In some cases, the imaging agent is enriched in 18F. In some cases, an imaging agent including salt forms (e.g., ascorbate salt) may be used to image an area of interest in a subject, including, but not limited to, the heart, cardiovascular system, cardiac vessels, brain, and other organs.
    Type: Application
    Filed: May 11, 2011
    Publication date: June 13, 2013
    Applicant: Lantheus Medical Imaging, Inc.
    Inventors: Ajay Purohit, Pedro Benites, Edward H. Cheesman, Joel Lazewatsky, L. Veronica Lee, Richard R. Cesati, Richard J. Looby, Heike S. Radeke
  • Publication number: 20130018207
    Abstract: A compound having the formula (I) where each of R1, R2, R3 and R4 is independently C6-C18 aryl-, C5-C8 cycloalkyl-, C6-C18 aryl having at least one C1-C20 alkyl substituent, C5-C8 cycloalkyl having at least one C1-C20 alkyl s?bstituent, C4-C20 branched alkyl-, C16-C20 linear alkyl-, RO—, —NRR?, —PRR?, —SR, fluoro substituted forms thereof, and perfluoro forms thereof: and R5 is C6-C18 aryl-, C5-C8cycloalkyl-, C6-C18 aryl having at least one C1-C20 alkyl substituent, C5-C8 cycloalkyl having at least one C1-C20 alkyl substituent, C3-C20 branched alkyl-, C2-C30 linear alkyl-, fluoro substituted forms thereof, and perfluoro forms thereof; where R and R? are each independently C6-C18 aryl-, C5 -C8 cycloalkyl-, C6-C18 aryl having at least one C1-C20 alkyl substituent, C5-C8 cycloalkyl having at least one C1-C20 alkyl substituent, C4-C20 branched alkyl-, C2-C30 linear alkyl-, fluoro substituted forms thereof, and perfluoro forms thereof; A is N, P, S, or O with the proviso that when A is S, R2 is a nullity; and M is
    Type: Application
    Filed: September 14, 2012
    Publication date: January 17, 2013
    Applicant: STEPHAN CONSULTING CORPORATION
    Inventors: Douglas W. Stephan, Preston A. Chase, Gregory C. Welch
  • Publication number: 20120253042
    Abstract: A process for preparing amides by reacting a primary amine and a primary alcohol in the presence of a Ruthenium complex to generate the amide and molecular hydrogen. Primary amines are directly acylated by equimolar amounts of alcohols to produce amides and molecular hydrogen (the only byproduct) in high yields and high turnover numbers. Also disclosed are processes for hydrogenation of amides to alcohols and amines; hydrogenation of organic carbonates to alcohols; hydrogenation of carbamates or urea derivatives to alcohols and amines; amidation of esters; acylation of alcohols using esters; coupling of alcohols with water and a base to form carboxylic acids; dehydrogenation of beta-amino alcohols to form pyrazines and cyclic dipeptides; and dehydrogenation of secondary alcohols to ketones. These reactions are catalyzed by a Ruthenium complex which is based on a dearomatized PNN-type ligand of formula A1 or precursors thereof of formulae A2 or A3.
    Type: Application
    Filed: May 14, 2012
    Publication date: October 4, 2012
    Applicant: YEDA RESEARCH AND DEVELOPMENT CO. LTD.
    Inventors: David Milstein, Chidambaram Gunanathan, Yehoshua Ben-David, Ekambaram Balaraman, Boopathy Gnanaprakasam, Jing Zhang
  • Patent number: 8242264
    Abstract: The present invention relates to a process for preparing 4-acetyl-2,3,4,5-tetrahydro-benzo[1,4]diazepine and the intermediates thereof. The present invention provides a compound represented by formula I and a compound represented by formula II, and processes for preparing 4-acetyl-2,3,4,5-tetrahydro-benzo[1,4]diazepine by using the compound represented by formula I, the compound represented by formula II and o-nitrobenzaldehyde. The invention has the advantages of the shorter synthesis steps, easily available raw materials and simple operation. Moreover, the process is economic and safe by avoiding the use of expensive and dangerous lithium aluminum hydride.
    Type: Grant
    Filed: May 22, 2008
    Date of Patent: August 14, 2012
    Assignees: Topharman Shanghai Co., Ltd., Weifang Tehua Chemical Co., Ltd.
    Inventors: Fuqiang Zhu, Haihong Li, Wenzhong Wang, Hui Zhang, Jingshan Shen
  • Patent number: 8242318
    Abstract: Catalytic hydrogenation of a double bond, notably a C?C or C?N double bond, is carried out using a homogenous catalyst which is a complex of rhodium or other transition metal containing at least one ligand which is a nitrogenous organic base. Preferably the complex is phosphorus-free and the ligand is a bicyclic base having formula where R1 and R4 are hydrocarbon chains. R1 preferably is a saturated chain of two carbon atoms and R4 preferably is a saturated chain of three to five carbon atoms.
    Type: Grant
    Filed: December 3, 2009
    Date of Patent: August 14, 2012
    Assignee: Schlumberger Technology Corporation
    Inventors: Li Jiang, Timothy Jones, Fenglou Zou
  • Publication number: 20120142968
    Abstract: Disclosed are compounds represented by structural formula (I): methods of producing compounds represented by structural formula (I). and their use in inhibiting oxidation in an oxidizable material.
    Type: Application
    Filed: November 17, 2011
    Publication date: June 7, 2012
    Applicant: Polnox Corporation
    Inventors: Rajesh Kumar, Suizhou Yang, Vijayendra Kumar, Ashok L. Cholli
  • Patent number: 8119842
    Abstract: Methods for producing a compound of formula k1 or k2 by reducing a dihydronapthalene amide compound of formula i with hydrogen gas in the presence of a ruthenium catalyst of formula j1 or j2 Ru(Z)2(L)??j1; Ru(E)(E?)(L)(D)??j2; wherein m, n, Ar, Y, R1 E, E?, D, Z and L are as defined herein.
    Type: Grant
    Filed: December 14, 2009
    Date of Patent: February 21, 2012
    Assignee: Roche Palo Alto LLP
    Inventors: Kieran Durkin, Lawrence Emerson Fisher, Arthur Meili, Michaelangelo Scalone, Xianqing Shi, Justin Vitale
  • Publication number: 20120016139
    Abstract: The present invention relates to a catalyst system. In particular the invention relates to a catalyst in the form of metal or an alloy that is encapsulated within a polymer shell or matrix. More specifically the invention is directed towards reactive catalytic metals that may be pyrophoric or otherwise reactive in air and/or susceptible to oxidation. In particular, the invention is concerned with catalysts based on nickel. Raney or sponge nickel is highly hazardous: a self-igniting solid; produces hazardous fumes when burning; causes irritation of the respiratory tract, nasal cavities; causes pulmonary fibrosis if inhaled; ingestion may lead to convulsions and intestinal disorders; causes eye and skin irritation; and chronic exposure may lead to pneumonitis and sensitization (“nickel itch”). The invention provides metal catalysts that avoid such problems and have a good shelf life and working life.
    Type: Application
    Filed: February 12, 2010
    Publication date: January 19, 2012
    Applicant: REAXA LIMITED
    Inventors: Thomas Eric Oliver Screen, Mohammed Nisar
  • Patent number: 7985880
    Abstract: There is provided a method for producing an optically active 1-(fluoro-, trifluoromethyl- or trifluoromethoxy-substituted phenyl)alkylamine N-monoalkyl derivative, which includes the steps of conducting reductive alkylation of an optically active secondary amine and a formaldehyde (including an equivalent thereof) or lower aldehyde in the presence of a transition metal catalyst under a hydrogen gas atmosphere, thereby converting the secondary amine to an optically active tertiary amine of the formula, and subjecting the tertiary amine to hydrogenolysis. The target optically active compound can be produced efficiently by this production method.
    Type: Grant
    Filed: June 25, 2007
    Date of Patent: July 26, 2011
    Assignee: Central Glass Company, Limited
    Inventors: Akihiro Ishii, Kaori Mogi, Hideyuki Tsuruta, Kenjin Inomiya
  • Patent number: 7915452
    Abstract: A method of producing xylylenediamine from xylene. In the method, xylene is converted into dicyanobenzene by ammoxidation. The produced dicyanobenzene is extracted into an organic solvent. The extract is then distilled to separate dicyanobenzene from the organic solvent. After added with a solvent, the separated dicyanobenzene is hydrogenated in a liquid phase. Finally, the hydrogenation product is purified by distillation to obtain a highly pure xylylenediamine. The method is conducted in a simple and low energy-consuming process.
    Type: Grant
    Filed: June 22, 2005
    Date of Patent: March 29, 2011
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventor: Kazuhiko Amakawa
  • Publication number: 20110009646
    Abstract: There are provided a novel ruthenium-diamine complex, and methods for selectively producing an optically active alcohol and an optically active amine, which are important as precursors for the synthesis of medicinal drugs and functional materials, using the ruthenium-diamine complex as a catalyst. A novel ruthenium-diamine complex prepared by introducing a trisubstituted silyl group into an aromatic compound (arene) moiety that is coordinated with a ruthenium complex having an optically active diamine as a ligand, a catalyst for asymmetric reduction formed from the ruthenium-diamine complex, and a method for producing an optically active alcohol or an optically active amine using the catalyst.
    Type: Application
    Filed: July 13, 2010
    Publication date: January 13, 2011
    Applicant: TAKASAGO INTERNATIONAL CORPORATION
    Inventors: Taichiro Touge, Hideki Nara
  • Publication number: 20100256358
    Abstract: The present invention relates to a process for preparing 4-acetyl-2,3,4,5-tetrahydro-benzo[1,4]diazepine and the intermediates thereof. The present invention provides a compound represented by formula I and a compound represented by formula II, and processes for preparing 4-acetyl-2,3,4,5-tetrahydro-benzo[1,4]diazepine by using the compound represented by formula I, the compound represented by formula II and o-nitrobenzaldehyde. The invention has the advantages of the shorter synthesis steps, easily available raw materials and simple operation. Moreover, the process is economic and safe by avoiding the use of expensive and dangerous lithium aluminum hydride.
    Type: Application
    Filed: May 22, 2008
    Publication date: October 7, 2010
    Applicants: TOPHARMAN SHANGHAI CO., LTD., WEIFANG TEHUA CHEMICAL CO., LTD.
    Inventors: Fuqiang Zhu, Haihong Li, Wenzhong Wang, Hui Zhang, Jingshan Shen
  • Publication number: 20100168454
    Abstract: Catalytic hydrogenation of a double bond, notably a C?C or C?N double bond, is carried out using a homogenous catalyst which is a complex of rhodium or other transition metal containing at least one ligand which is a nitrogenous organic base. Preferably the complex is phosphorus-free and the ligand is a bicyclic base having formula where R1 and R4 are hydrocarbon chains. R1 preferably is a saturated chain of two carbon atoms and R4 preferably is a saturated chain of three to five carbon atoms.
    Type: Application
    Filed: December 3, 2009
    Publication date: July 1, 2010
    Applicant: Schlumberger Technology Corporation
    Inventors: Li Jiang, Timothy Jones, Fenglou Zou
  • Patent number: 7728174
    Abstract: Processes for preparing a xylylenediamine by continuous hydrogenation, wherein the processes comprise: introducing a liquid circulation stream comprising a phthalonitrile and ammonia into a reactor to continuously hydrogenate the phthalonitrile in the presence of a heterogenous catalyst and the ammonia such that a reactor effluent comprising the xylylenediamine is formed; drawing off a portion of the reactor effluent to provide a first recycle stream; mixing at least a portion of the first recycle stream in a mixing unit with liquid ammonia and fresh phthalonitrile in solid or molten form to provide a second recycle stream; and recycling the second recycle stream to the liquid circulation stream, or wherein the second recycle stream and any remaining unmixed portion of the first recycle stream are both recycled to the liquid circulation stream.
    Type: Grant
    Filed: July 27, 2006
    Date of Patent: June 1, 2010
    Assignee: BASF SE
    Inventors: Randolf Hugo, Kirsten Dahmen, Sabine Huber
  • 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
  • Publication number: 20090192334
    Abstract: A method of producing xylylenediamine from xylene. In the method, xylene is converted into dicyanobenzene by ammoxidation. The produced dicyanobenzene is extracted into an organic solvent. The extract is then distilled to separate dicyanobenzene from the organic solvent. After added with a solvent, the separated dicyanobenzene is hydrogenated in a liquid phase. Finally, the hydrogenation product is purified by distillation to obtain a highly pure xylylenediamine. The method is conducted in a simple and low energy-consuming process.
    Type: Application
    Filed: June 22, 2005
    Publication date: July 30, 2009
    Inventor: Kazuhiko Amakawa
  • Patent number: 7465832
    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: Grant
    Filed: May 17, 2007
    Date of Patent: December 16, 2008
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Tomohiro Sugawara, Takafumi Abe, Tatsuyuki Kumano, Kinji Kato
  • Patent number: 7449604
    Abstract: An aromatic dinitrile compound is hydrogenated in an amide solvent in the presence of a solid catalyst and in the absence of ammonia to produce an aromatic ring-containing amino compound by reducing at least one cyano group to aminomethyl group. The solid catalyst is a supported palladium catalyst in which palladium is substantially present on the outer surface of carrier and in a surface layer within a depth of 200 ?m from the outer surface. Using such a solid catalyst, the aromatic dinitrile compound is efficiently hydrogenated to the aromatic ring-containing amino compound under mild conditions.
    Type: Grant
    Filed: September 8, 2006
    Date of Patent: November 11, 2008
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Atsushi Okamoto, Toshio Watanabe
  • 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: 7321066
    Abstract: The invention provides a method for efficiently producing an aromatic diamine derivative represented by formula (3) at high yield, the method including reacting an aromatic amide represented by formula (1) with an aromatic halide represented by formula (2): (wherein each of Ar, Ar1 and Ar2 represents a substituted or unsubstituted aryl group or heteroaryl group; Ar3 represents a substituted or unsubstituted arylene group or heteroarylene group; and X represents a halogen atom).
    Type: Grant
    Filed: January 28, 2004
    Date of Patent: January 22, 2008
    Assignee: Idemitsu Kosan Co., Ltd.
    Inventors: Hisayuki Kawamura, Hiroyuki Matsui, Koji Hirota
  • Patent number: 7119122
    Abstract: There are provided novel compounds of formula (I) wherein A, R1, R3, R4, R5, T, U, V, W, X and Y are as defined in the specification, and pharmaceutically acceptable salts thereof; together with processes for their preparation, compositions containing them and their use in therapy.
    Type: Grant
    Filed: October 2, 2002
    Date of Patent: October 10, 2006
    Assignee: Astrazeneca AB
    Inventors: Stephen Connolly, Glen Ernst
  • Patent number: 7119230
    Abstract: In the process of the present invention, xylylenediamine and/or cyanobenzylamine is produced by a catalytic liquid-phase hydrogenation of a phthalonitrile compound. The liquid-phase hydrogenation is performed by controlling the concentration of a benzamide compound to a specific level or lower. In a preferred embodiment, the concentration of a benzoic acid compound is further controlled to a specific level or lower. By the process, xylylenediamine and/or cyanobenzylamine is produced at high yields and the catalyst life is prolonged.
    Type: Grant
    Filed: June 30, 2003
    Date of Patent: October 10, 2006
    Assignee: Mitsubishi Gas Chemical Co., Inc.
    Inventors: Kazuhiko Amakawa, Takuji Shitara
  • Patent number: 7078226
    Abstract: A process for preparing optically active amines, a process for preparing racemic amines which can be resolved using optically active carboxylic acids or enzymes, and racemic and optically active amines and optically active amides are described.
    Type: Grant
    Filed: November 13, 2000
    Date of Patent: July 18, 2006
    Assignee: BASF Aktiengesellschaft
    Inventors: Klaus Ditrich, Wolfgang Siegel
  • Patent number: 6894195
    Abstract: A process for the preparation of 4-methyl-2,3,5,6-tetrafluorobenzyl alcohol comprising hydrogenating 4-methyl-2,3,5,6-tetrafluorobenzonitrile to 4-methyl-2,3,5,6-tetrafluorobenzylamine and converting 4-methyl-2,3,5,6-tetrafluorobenzylamine to 4-methyl-2,3,5,6-tetrafluorobenzyl alcohol. The process optionally also comprises the further step of reacting 4-Methyl-2,3,5,6-tetrafluobenzyl alcohol with cis-Z-3-(2-chloro-1,1,1-trifluoro-2-propenyl)-2,2-dimethylcyclopropanecarbonyl chloride to the form tefluthrin. 4-Methyl-2,3,5,6-tetrafluorobenzylamine and salts thereof are also claimed.
    Type: Grant
    Filed: October 18, 2001
    Date of Patent: May 17, 2005
    Assignee: Syngenta Limited
    Inventors: Raymond Vincent Heavon Jones, Stephen Martin Brown
  • Patent number: 6797842
    Abstract: An optically active 1-(fluoro- or trifluoromethyl-substituted phenyl)ethylamine is produced with high optical purity and in an industrially simple and efficient manner by asymmetrically reducing an optically active imine, obtained by dehydration and condensation of a fluoro- or trifluoromethyl-substituted phenylmethyl ketone and an optically active primary amine under acidic conditions, using a hydride reducing agent to convert to an optically active secondary amine, and subjecting the secondary amine or its salt of an inorganic acid or organic acid to hydrogenolysis.
    Type: Grant
    Filed: May 11, 2001
    Date of Patent: September 28, 2004
    Assignee: Central Glass Company, Limited
    Inventors: Akihiro Ishii, Manabu Yasumoto, Yokusu Kuriyama, Masatomi Kanai, Takashi Hayami
  • Patent number: 6649799
    Abstract: A method for producing amines by catalytic hydrogenation of nitrites or imines with hydrogen-containing gases in the presence of a molded hydrogenation catalyst of Raney type, where the Raney catalyst is in the form of hollow bodies.
    Type: Grant
    Filed: December 21, 2001
    Date of Patent: November 18, 2003
    Assignee: Degussa AG
    Inventors: Daniel Ostgard, Monika Berweiler, Stefan Röder
  • Patent number: 6528491
    Abstract: The present invention relates to new pyranoside derivatives of general formula I, processes for preparing them as well as their use as medicaments:
    Type: Grant
    Filed: October 23, 2001
    Date of Patent: March 4, 2003
    Assignee: Boehringer Ingelheim Pharma KG
    Inventors: Ralf Anderskewitz, Kurt Schromm, Franz Birke, Hans Michael Jennewein
  • Patent number: 6476267
    Abstract: A method for producing an aromatic primary amine, characterized by hydrogenating an aromatic nitrile at a low partial pressure of hydrogen in a heterogeneous system comprising a non-reductive polar solvent and a nickel-immobilized catalyst suspended therein was proposed. By such method, an aromatic primary amine which is industrially useful as a medicine, agricultural chemical, dye surfactant, chemical agent, etc. can be produced in a high yield.
    Type: Grant
    Filed: November 19, 2001
    Date of Patent: November 5, 2002
    Assignee: Sagami Chemical Research Center
    Inventors: Takamasa Fuchigami, Satoshi Takamizawa, Noriko Wakasa
  • Patent number: 6476268
    Abstract: N-Benzylamines are prepared by a process in which (i) in a first step, a benzaldehyde is reacted with a primary amine to give the imine and (ii) in a second step, the imine is hydrogenated with hydrogen in the presence of a catalyst containing one or more metals of groups 8 to 10 of the Periodic Table of the Elements to give the N-benzylamine, wherein the iminization (i) is carried out in a water-miscible solvent and the resulting water of reaction is not removed, and the hydrogenation (ii) is carried out in the imine solution obtained in the iminization (i) and containing water of reaction.
    Type: Grant
    Filed: March 27, 2002
    Date of Patent: November 5, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Harald Winsel, Wolfgang Siegel, Michael Bartsch
  • Publication number: 20020103400
    Abstract: An optically active 1-(fluoro- or trifluoromethyl-substituted phenyl)ethylamine is produced with high optical purity and in an industrially simple and efficient manner by asymmetrically reducing an optically active imine, obtained by dehydration and condensation of a fluoro- or trifluoromethyl-substituted phenylmethyl ketone and an optically active primary amine under acidic conditions, using a hydride reducing agent to convert to an optically active secondary amine, and subjecting the secondary amine or its salt of an inorganic acid or organic acid to hydrogenolysis.
    Type: Application
    Filed: May 11, 2001
    Publication date: August 1, 2002
    Inventors: Akihiro Ishii, Manabu Yasumoto, Yokusu Kuriyama, Masatomi Kanai, Takashi Hayami
  • Patent number: 6376712
    Abstract: The present invention relates to a process for producing a trifluoromethylbenzylamine represented by the general formula (1), where R1 represents hydrogen atom, a halogen atom selected from the group consisting of fluorine, chlorine, bromine and iodine, or trifluoromethyl group. This process includes the step of reducing an oxime by hydrogen in an organic solvent in the presence of a catalyst and ammonia. The oxime is represented by the general formula (2), where R1 is defined as above, and R2 represents hydrogen atom, an alkyl group or an aralkyl group. With this process, the trifluoromethylbenzylamine can be produced with high yield.
    Type: Grant
    Filed: April 12, 2001
    Date of Patent: April 23, 2002
    Assignee: Central Glass Company, Limited
    Inventors: Satoru Narizuka, Eri Tsukada, Takashi Kume
  • Publication number: 20020040163
    Abstract: A process for the production of 3-hydroxypropionitrile is provided. This process includes (a) reacting acrylonitrile with water at a defined molar ratio in the presence of a weak base under specific temperature and pressure conditions until a conversion in the range of about 40% to about 80% has been achieved; (b) after cooling the mixture obtained in (a), separating off its aqueous phase; (c) distilling off the acrylonitrile from the organic phase remaining after (b); (d) subjecting the mixture obtained in (c) to pyrolysis at specific temperature and pressure conditions in the presence of a basic catalyst to obtain a mixture consisting mainly of 3-hydroxypropionitrile and acrylonitrile; and (e) isolating the desired 3-hydroxypropionitrile by fractional distillation from the mixture obtained in (d). Such a process in which the basic aqueous phase and the acrylonitrile that has been distilled off are recycled represents a preferred embodiment.
    Type: Application
    Filed: January 17, 2001
    Publication date: April 4, 2002
    Inventors: Bruno Burdet, August Ruettiman, Karin Riegl, Thomas Andreas Riegl, Maximilian Lutz Riegl
  • Patent number: 6362372
    Abstract: The invention relates to a process for producing a trifluoromethylbenzylamine represented by the following general formula (1), where each R independently represents a halogen selected from the group consisting of fluorine, chlorine, bromine and iodine, an alkyl group having a carbon atom number of 1-4, an alkoxy group having a carbon atom number of 1-4, an amino group, a hydroxyl group or a trifluoromethyl group, and n represents an integer from 0 to 4. The process includes hydrogenating a trifluoromethylbenzonitrile by hydrogen in an organic solvent in the presence of ammonia and a catalyst containing a platinum group element. This trifluoromethylbenzonitrile is represented by the following general formula (2), where R and n are defined as above. With this process, it is possible to obtain the trifluoromethylbenzylamine at an extremely high yield.
    Type: Grant
    Filed: April 12, 2001
    Date of Patent: March 26, 2002
    Assignee: Central Glass Company, Limited
    Inventors: Satoru Narizuka, Takashi Kume
  • Publication number: 20020013500
    Abstract: The present invention relates to a process for producing a trifluoromethylbenzylamine represented by the general formula (1), 1
    Type: Application
    Filed: April 12, 2001
    Publication date: January 31, 2002
    Inventors: Satoru Narizuka, Eri Tsukada, Takashi Kume
  • Patent number: 6340773
    Abstract: A method of preparing a halogenated primary amine comprising hydrogenating a halogenated oxime in the presence of a catalyst comprising a non-palladium noble metal or a base metal under conditions sufficient to produce a halogenated primary amine.
    Type: Grant
    Filed: September 14, 1999
    Date of Patent: January 22, 2002
    Assignee: AlliedSignal Inc.
    Inventors: Mingbao Zhang, Michael A. Kocur, Mary Frances Martin
  • Patent number: 6331649
    Abstract: The present invention relates to a process for producing a trifluoromethylbenzylamine represented by the general formula (1). This process includes the step of reducing an oxime represented by the general formula (2), where R1 represents hydrogen atom, a halogen atom selected from the group consisting of fluorine, chlorine, bromine and iodine, or trifluoromethyl group, where R1 is defined as above, and R2 represents hydrogen atom, an alkyl group or an aralkyl group. With this process, the trifluoromethylbenzylamine can be produced with high selectivity.
    Type: Grant
    Filed: March 21, 2000
    Date of Patent: December 18, 2001
    Assignee: Central Glass Company, Limited
    Inventors: Satoru Narizuka, Yutaka Katsuhara
  • Patent number: 6288277
    Abstract: The present invention relates to new phenylamine derivatives, processes for preparing them and their use as pharmaceutical compositions.
    Type: Grant
    Filed: April 3, 2000
    Date of Patent: September 11, 2001
    Assignee: Boehringer Ingelheim Pharma KG
    Inventors: Ralf Anderskewitz, Kurt Schromm, Ernst-Otto Renth, Franz Birke, Hans Michael Jennewein, Christopher John Montague Meade