Including Hydrogenating Benzene Ring Patents (Class 564/449)
  • Patent number: 8865939
    Abstract: A method for producing trans-1,4-bis(aminomethyl)cyclohexane includes a nuclear hydrogenation step of producing a hydrogenated terephthalic acid or terephthalic acid derivative by nuclear hydrogenation of a terephthalic acid or terephthalic acid derivative, the terephthalic acid or terephthalic acid derivative being at least one selected from the group consisting of terephthalic acid, terephthalic acid ester, and terephthalic acid amide; a cyanation step of treating the hydrogenated terephthalic acid or terephthalic acid derivative with ammonia, thereby producing 1,4-dicyanocyclohexane, and producing trans-1,4-dicyanocyclohexane from the obtained 1,4-dicyanocyclohexane; and an aminomethylation step of treating the trans-1,4-dicyanocyclohexane with hydrogen, thereby producing trans-1,4-bis(aminomethyl)cyclohexane. Metal oxide is used as a catalyst in the cyanation step, and the obtained trans-1,4-dicyanocyclohexane has a metal content of 3000 ppm or less.
    Type: Grant
    Filed: October 5, 2011
    Date of Patent: October 21, 2014
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Naritoshi Yoshimura, Shinji Kiyono, Tetsuya Hamada, Eiji Watanabe, Saiko Sawada
  • Patent number: 8865938
    Abstract: A method for producing bis(aminomethyl)cyclohexanes includes a nuclear hydrogenation step of producing hydrogenated phthalic acids or phthalic acid derivatives by nuclear hydrogenation of phthalic acids or phthalic acid derivatives of at least one selected from the group consisting of phthalic acids, phthalic acid esters, and phthalic acid amides; a cyanation step of treating the hydrogenated phthalic acids or phthalic acid derivatives obtained in the nuclear hydrogenation step with ammonia, thereby producing dicyanocyclohexanes; and an aminomethylation step of treating the dicyanocyclohexanes obtained in the cyanation step with hydrogen, thereby producing bis(aminomethyl)cyclohexanes. In the cyanation step, metal oxide is used as a catalyst, and the obtained dicyanocyclohexanes have a metal content of 3000 ppm or less.
    Type: Grant
    Filed: October 5, 2011
    Date of Patent: October 21, 2014
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Naritoshi Yoshimura, Shinji Kiyono, Tetsuya Hamada, Eiji Watanabe, Saiko Sawada
  • Patent number: 8759591
    Abstract: The present invention discloses a method for intermittently producing 4,4?-diaminodicyclohexyl methane (H12MDA) with a low amount of the trans-trans isomer thereof, which comprises: controlling the reaction process by stopping the reaction when, except for a solvent, the reaction solution comprises MDA of 0-5 wt % and H6MDA of 1-20 wt %; and b) separating the reaction solution obtained from step a) by conventional means to obtain H12MDA product with desired purity, and allowing the un-reacted material and intermediate product to be recycled to the reactor after being accumulated. The method of the present invention decreases the amount of the trans-trans isomer in H12MDA, increases the yield of the reaction, and reduces the production cost. The present invention also provides a post treatment process of the reaction mixture.
    Type: Grant
    Filed: June 3, 2011
    Date of Patent: June 24, 2014
    Assignees: Wanhua Chemical Group Co., Ltd., Wanhua Chemical (Ningbo) Co., Ltd.
    Inventors: Shuang Hu, Hao Chen, Zilin Ni, Wangshun Qi, Zhongying Chen, Zhiyuan Liu, Xudong Wang, Zhanyu Zhao, Weiqi Hua
  • Patent number: 8586794
    Abstract: The present invention relates to 5-isopropyl-3-aminomethyl-2-methyl-1-aminocyclohexane (carvonediamine) and to a process for preparation thereof by a) reacting carvone with hydrogen cyanide, b) then reacting the carvonenitrile obtained in stage a) with ammonia in the presence of an imine formation catalyst and c) then reacting the carvonenitrile imine-containing reaction mixture obtained in stage b) with hydrogen and ammonia over hydrogenation catalysts. The present invention further relates to the use of carvonediamine as a hardener for epoxy resins, as an intermediate in the preparation of diisocyanates, as a starter in the preparation of polyetherols and/or as a monomer for polyamide preparation.
    Type: Grant
    Filed: July 13, 2009
    Date of Patent: November 19, 2013
    Assignee: BASF SE
    Inventors: Martin Ernst, Alfred Oftring, Kathrin Wissel-Stoll, Oemer Uensal, Stephan Freyer, Ansgar Gereon Altenhoff, Wolfgang Staffel
  • Publication number: 20120116099
    Abstract: The present invention relates to a method of continuously conveying a liquid which is used as starting material in a chemical reaction by means of a displacement pump having physically separate forward-transport valves and a liquid-filled bidirectional flow line between displacement pump and forward-transport valves, wherein an auxiliary liquid which is a product or a starting material of the chemical reaction and has a melting point which is below the melting point or below the saturation temperature of the liquid to be conveyed is present in the bidirectional flow line. The present invention additionally provides for the use of a product formed by hydrogenation of an aromatic compound as auxiliary liquid for conveying an aromatic compound and also the use of an alcohol or an ester derived from alcohol and carboxylic acid as auxiliary liquid for conveying carboxylic acids or carboxylic acid derivatives.
    Type: Application
    Filed: July 6, 2010
    Publication date: May 10, 2012
    Applicant: BASF SE
    Inventors: Joachim Pfeffinger, Willi Gilcher, Juergen Morell
  • Patent number: 6984758
    Abstract: A crude liquid containing 1,3-bis(aminomethyl)cyclohexane and a high-boiling component having a boiling point higher than that of 1,3-bis(aminomethyl)cyclohexane is distilled. By controlling the distillation conditions, the high-boiling component is prevented from entering into a distilled 1,3-bis(aminomethyl)cyclohexane and the content of a low-boiling component in the distilled 1,3-bis(aminomethyl)cyclohexane is minimized.
    Type: Grant
    Filed: March 16, 2005
    Date of Patent: January 10, 2006
    Assignee: Mitsubishi Gas Chemical Co., Inc.
    Inventors: Kazuhiko Amakawa, Kuniaki Muneyasu, Hiroshi Watanabe
  • Patent number: 6340772
    Abstract: Three processes are described for preparing (hetero)aromatic substituted benzene derivatives which comprise aromatization of cyclohexenone derivatives via (chloro)cyclohexadiene derivatives.
    Type: Grant
    Filed: April 24, 2001
    Date of Patent: January 22, 2002
    Assignee: Nippon Kayaku Co., Ltd.
    Inventors: Tetsuya Toya, Hidetoshi Shirakura, Junichi Kon
  • Patent number: 6271418
    Abstract: Three processes are described for preparing (hetero)aromatic substituted benzene derivatives which comprise aromatization of cyclohexenone derivatives via (chloro)cyclohexadiene derivatives.
    Type: Grant
    Filed: February 22, 2000
    Date of Patent: August 7, 2001
    Assignee: Nippon Kayaku Co., Ltd.
    Inventors: Tetsuya Toya, Hidetoshi Shirakura, Junichi Kon
  • Patent number: 6156933
    Abstract: Process for the selective hydrogenation of alphatic or aromatic substrates under supercritical or near critical conditions. Hydrogenation is effected using a heterogeneous catalyst in a continuous flow reactor containing a supercritical or near critical reaction medium and selectively of product formation is achieved by varying one or more of the temperature, pressure, catalyst and flow rate.
    Type: Grant
    Filed: February 18, 1999
    Date of Patent: December 5, 2000
    Assignees: Degussa-Huls AG, Thomas Swan & Co. Ltd.
    Inventors: Martyn Poliakoff, Thomas M. Swan, Thomas Tacke, Martin G. Hitzler, Stephen K. Ross, Stefan Wieland
  • Patent number: 5741928
    Abstract: Disclosed is a process for producing bis(aminomethyl)cyclohexane, which comprises hydrogenating a xylylenediamine in the presence of a catalyst and at least one solvent selected from the group consisting alkylamines and alkylenediamines.
    Type: Grant
    Filed: September 19, 1995
    Date of Patent: April 21, 1998
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Shoichi Kobayashi, Susumu Naito
  • Patent number: 5514358
    Abstract: Methods for synthesis of chemical compounds by catalytic transfer hydrogenation comprise forming a mixture of a starting material, a hydrogen donor material and a catalyst. The catalyst is selected from a catalytic form of carbon, a polyethylene glycol phase transfer agent, and mixtures thereof. The mixture is heated at a temperature of from 30.degree. to 400.degree. C. in the presence of at least one alkali or alkaline earth metal compound to cause reduction of the starting material by catalytic transfer hydrogenation and form the desired chemical compound product.
    Type: Grant
    Filed: March 29, 1995
    Date of Patent: May 7, 1996
    Inventors: Charles J. Rogers, Alfred Kornel
  • Patent number: 5454720
    Abstract: A method for providing detection of timing anomalies and eliminating falsely detected positions in a hyperbolic positioning system for a simulated battlefield system. The method selects a large number of transmitters for calculation of position of an object or person on the battle field. In addition, transmitters are selected which have a high dilution of precision factor.
    Type: Grant
    Filed: May 31, 1994
    Date of Patent: October 3, 1995
    Assignee: Motorola, Inc.
    Inventors: Mark R. FitzGerald, Craig T. Griffin, Glen E. Sater
  • Patent number: 5371293
    Abstract: Bisaminomethylcyclohexane is produced in high yield by one-stage process from an aromatic dinitrile by hydrogenating the aromatic dinitrile in the presence of a ruthenium catalyst containing 1 to 10% by weight of ruthenium, in terms of metallic ruthenium, supported on a carrier, and in the presence of 0.5 parts by weight or more of liquid ammonia per part by weight of the aromatic nitrile at a temperature of 70.degree. to 150.degree. C. and a hydrogen partial pressure of 50 to 150 atm.
    Type: Grant
    Filed: March 28, 1994
    Date of Patent: December 6, 1994
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventor: Makoto Takagawa
  • Patent number: 5322965
    Abstract: Optionally substituted cyclohexylamine and optionally substituted dicyclohexylamine can be obtained by catalytic hydrogenation of optionally substituted aniline, a catalyst being employed which contains ruthenium, palladium or a mixture of both metals, which are applied to a support of niobic acid or tantalic acid or a mixture of both. The catalyst contains the noble metal(s) in a total amount from 0.05 to 5% by weight, relative to the total weight of the catalyst. In the case of the use of both noble metals, their weight ratio to one another is 1:9-9:1.
    Type: Grant
    Filed: August 27, 1993
    Date of Patent: June 21, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Otto Immel, Gerhard Darsow, Helmut Waldmann, Gerd-Michael Petruck
  • Patent number: 4513149
    Abstract: Hydrogenation processes utilizing improved Raney nickel alloy catalysts are disclosed. The catalyst comprises a monolithic mesh type structure of a nickel alloy having an integral Beta phase Raney Ni.sub.x M.sub.1-x coating on its outer surfaces, where M is a catalytic activator selected from the group consisting of molybdenum, ruthenium, tantalum and titanium and where x, the weight fraction of nickel in the combined alloy, is between about 0.80 and about 0.95. The catalyst is effective in processes for hydrogenation of aromatic compounds of the type ##STR1## wherein K is either benzene or naphthalene, R.sub.1 is a hydrogen atom or an aliphatic chain containing from about 1 to about 9 carbon atoms or a phenyl radical, R.sub.2 is a hydrogen atom or an aliphatic chain containing from about 1 to about 3 carbon atoms, and R.sub.3 and R.sub.4 are hydrogen atoms, hydroxy, or nitro groups.
    Type: Grant
    Filed: April 5, 1982
    Date of Patent: April 23, 1985
    Assignee: Olin Corporation
    Inventors: Thomas J. Gray, Norman G. Masse
  • Patent number: 4503251
    Abstract: Hydrogenation processes utilizing improved Raney nickel alloy catalysts are disclosed. The catalyst comprises a monolithic mesh type structure of a nickel alloy having an integral Beta phase Raney Ni.sub.x M.sub.1-x coating on its outer surfaces, where M is a catalytic activator selected from the group consisting of molybdenum, ruthenium, tantalum and titanium and where x, the weight fraction of nickel in the combined alloy, is between about 0.80 and about 0.95. The catalyst is effective in processes for hydrogenating an amine-substituted aromatic compound of the type ##STR1## wherein K is either benzene or naphthalene, R.sub.1 is a hydrogen atom or an aliphatic chain containing from about 1 to about 12 carbon atoms or a phenyl radical, R.sub.2 is a hydrogen atom, an amine group or an aliphatic chain containing from about 1 to about 3 carbon atoms, R.sub.3 is hydrogen or an amine group, and R.sub.4 is an amine group.
    Type: Grant
    Filed: April 5, 1982
    Date of Patent: March 5, 1985
    Assignee: Olin Corporation
    Inventors: Thomas J. Gray, Norman G. Masse, Richard A. Hagstrom