Including Hydrogenating Benzene Ring Patents (Class 564/449)
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Patent number: 8865939Abstract: 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: GrantFiled: October 5, 2011Date of Patent: October 21, 2014Assignee: Mitsui Chemicals, Inc.Inventors: Naritoshi Yoshimura, Shinji Kiyono, Tetsuya Hamada, Eiji Watanabe, Saiko Sawada
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Patent number: 8865938Abstract: 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: GrantFiled: October 5, 2011Date of Patent: October 21, 2014Assignee: Mitsui Chemicals, Inc.Inventors: Naritoshi Yoshimura, Shinji Kiyono, Tetsuya Hamada, Eiji Watanabe, Saiko Sawada
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Patent number: 8759591Abstract: 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: GrantFiled: June 3, 2011Date of Patent: June 24, 2014Assignees: 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
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Patent number: 8586794Abstract: 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: GrantFiled: July 13, 2009Date of Patent: November 19, 2013Assignee: BASF SEInventors: Martin Ernst, Alfred Oftring, Kathrin Wissel-Stoll, Oemer Uensal, Stephan Freyer, Ansgar Gereon Altenhoff, Wolfgang Staffel
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Publication number: 20120116099Abstract: 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: ApplicationFiled: July 6, 2010Publication date: May 10, 2012Applicant: BASF SEInventors: Joachim Pfeffinger, Willi Gilcher, Juergen Morell
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Patent number: 6984758Abstract: 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: GrantFiled: March 16, 2005Date of Patent: January 10, 2006Assignee: Mitsubishi Gas Chemical Co., Inc.Inventors: Kazuhiko Amakawa, Kuniaki Muneyasu, Hiroshi Watanabe
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Patent number: 6340772Abstract: Three processes are described for preparing (hetero)aromatic substituted benzene derivatives which comprise aromatization of cyclohexenone derivatives via (chloro)cyclohexadiene derivatives.Type: GrantFiled: April 24, 2001Date of Patent: January 22, 2002Assignee: Nippon Kayaku Co., Ltd.Inventors: Tetsuya Toya, Hidetoshi Shirakura, Junichi Kon
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Patent number: 6271418Abstract: Three processes are described for preparing (hetero)aromatic substituted benzene derivatives which comprise aromatization of cyclohexenone derivatives via (chloro)cyclohexadiene derivatives.Type: GrantFiled: February 22, 2000Date of Patent: August 7, 2001Assignee: Nippon Kayaku Co., Ltd.Inventors: Tetsuya Toya, Hidetoshi Shirakura, Junichi Kon
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Patent number: 6156933Abstract: 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: GrantFiled: February 18, 1999Date of Patent: December 5, 2000Assignees: Degussa-Huls AG, Thomas Swan & Co. Ltd.Inventors: Martyn Poliakoff, Thomas M. Swan, Thomas Tacke, Martin G. Hitzler, Stephen K. Ross, Stefan Wieland
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Patent number: 5741928Abstract: 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: GrantFiled: September 19, 1995Date of Patent: April 21, 1998Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Shoichi Kobayashi, Susumu Naito
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Patent number: 5514358Abstract: 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: GrantFiled: March 29, 1995Date of Patent: May 7, 1996Inventors: Charles J. Rogers, Alfred Kornel
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Patent number: 5454720Abstract: 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: GrantFiled: May 31, 1994Date of Patent: October 3, 1995Assignee: Motorola, Inc.Inventors: Mark R. FitzGerald, Craig T. Griffin, Glen E. Sater
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Patent number: 5371293Abstract: 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: GrantFiled: March 28, 1994Date of Patent: December 6, 1994Assignee: Mitsubishi Gas Chemical Company, Inc.Inventor: Makoto Takagawa
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Patent number: 5322965Abstract: 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: GrantFiled: August 27, 1993Date of Patent: June 21, 1994Assignee: Bayer AktiengesellschaftInventors: Otto Immel, Gerhard Darsow, Helmut Waldmann, Gerd-Michael Petruck
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Patent number: 4513149Abstract: 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: GrantFiled: April 5, 1982Date of Patent: April 23, 1985Assignee: Olin CorporationInventors: Thomas J. Gray, Norman G. Masse
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Patent number: 4503251Abstract: 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: GrantFiled: April 5, 1982Date of Patent: March 5, 1985Assignee: Olin CorporationInventors: Thomas J. Gray, Norman G. Masse, Richard A. Hagstrom