Plural Amino Nitrogens Containing Patents (Class 564/451)
  • Patent number: 9403754
    Abstract: A catalytic process for hydrogenating aromatic di- and polyamines with the aid of a selected catalyst system is provided, which comprises a mixture of a first heterogeneous catalyst and a second heterogeneous catalyst and a nitro compound (nitrate and/or nitrite salt). The first and second heterogeneous catalyst each independently comprise a metal selected from the group consisting of Cr, Mo, W, Mn, Re, Fe, Ru, Os, Co, Rh, Ir, Ni, Pd and/or Pt and the metal selected for the second heterogeneous catalyst is different from the metal selected for the first heterogeneous catalyst. Hydrogenation of aromatic rings having two or more amino groups bound to the aromatic ring produces cycloaliphatic di- and polyamines, which are useful chemical intermediates, e.g., for further reaction with epoxides or isocyanates. The amino groups may also be converted to isocyanates via reaction with phosgene. The resulting cycloaliphatic di- and polyisocyanates may also be used as monomers for making polymers.
    Type: Grant
    Filed: February 4, 2015
    Date of Patent: August 2, 2016
    Assignee: Bayer MaterialScience AG
    Inventors: Thomas E. Müller, Christoph Gürtler, Reinhard Halpaap, Christoph Thiebes, Ewa Gebauer-Henke, Isabel U. Castro Cevallos, Walter Leitner
  • Patent number: 9278906
    Abstract: A process for hydrogenating aromatic di- and polyamines is provided comprising the steps of reacting the aromatic amine with hydrogen in the presence of a catalytic system, wherein the catalytic system comprises a heterogeneous catalyst comprising a metal selected from the group consisting of Cr, Mo, W, Mn, Re, Fe, Ru, Os, Co, Rh, Ir, Ni, Pd and/or Pt and a support, and wherein the catalyst system further comprises an organic nitro compound. Hydrogenation of aromatic di- and polyamines having two or more amino groups bound to the aromatic ring produces cycloaliphatic di- and polyamines, which are useful chemical intermediates, e.g., for further reaction with epoxides or isocyanates. The amino groups may also be converted to isocyanates via reaction with phosgene. The resulting cycloaliphatic di- and polyisocyanates may also be used as monomers for making polymers.
    Type: Grant
    Filed: February 4, 2015
    Date of Patent: March 8, 2016
    Assignee: Bayer MaterialScience AG
    Inventors: Thomas E. Müller, Christoph Gürtler, Reinhard Halpaap, Ewa Gebauer-Henke, Walter Leitner, Patrick Tomkins, Christoph Thiebes
  • Patent number: 8987517
    Abstract: A process for preparing cycloaliphatic amines by hydrogenating the corresponding aromatic compounds with hydrogen-comprising gas at a temperature of from 30 to 280° C. and a pressure of 50-350 bar, in the presence of ruthenium catalysts. The hydrogenation is performed in the presence of from 1% by weight to 500% by weight, based on the catalyst calculated as elemental ruthenium (Ru), of suspended inorganic additives, and to the use of the cycloaliphatic amines as a synthesis unit.
    Type: Grant
    Filed: January 14, 2009
    Date of Patent: March 24, 2015
    Assignee: BASF SE
    Inventors: Joachim Pfeffinger, Willi Doell
  • 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: 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: 8772546
    Abstract: Disclosed is a process for the preparation of 1,2-cycloaliphatic diamines from 1,2-aromatic diamines. In one embodiment, the process provides a method for making 1,2-diaminocyclohexane by the reaction of 1,2-phenylenediamine contained in a polar, protic solvent with hydrogen in the presence of a supported rhodium catalyst, ammonia, and an inorganic borohydride, and having enhanced overall conversion and selectivity.
    Type: Grant
    Filed: November 4, 2009
    Date of Patent: July 8, 2014
    Assignee: Invista North America S.àr.l.
    Inventor: Ronald L. Amey
  • 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: 8697914
    Abstract: Process for preparing bis(para-amino-cyclohexyl)methane by multiphase reaction of methylenedianiline with hydrogen, in which the reaction is performed in 5 to 50 series-connected reaction zones under adiabatic conditions.
    Type: Grant
    Filed: December 4, 2009
    Date of Patent: April 15, 2014
    Assignee: Bayer Intellectual Property GmbH
    Inventors: Evin Hizaler Hoffmann, Leslaw Mleczko, Ralph Schellen, Stephan Schubert
  • Publication number: 20120323041
    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: Application
    Filed: June 3, 2011
    Publication date: December 20, 2012
    Applicants: NINGBO WANHUA POLYURETHANES CO., LTD., YANTAI WANHUA POLYURETHANES CO., LTD.
    Inventors: Shuang Hu, Hao Chen, Zilin Ni, Wangshun Qi, Zhongying Chen, Zhiyuan Liu, Xudong Wang, Zhanyu Zhao, Weiqi Hua
  • Publication number: 20120296111
    Abstract: The present invention relates to an eggshell catalyst comprising an active metal selected from the group consisting of ruthenium, rhodium, palladium, platinum and mixtures thereof, applied to a support material comprising silicon dioxide, wherein the pore volume of the support material is 0.6 to 1.0 ml/g, determined by Hg porosimetry, the BET surface area is 280 to 500 m2/g, and at least 90% of the pores present have a diameter of 6 to 12 nm, to a process for preparing this eggshell catalyst, to a process for hydrogenating an organic compound which comprises at least one hydrogenatable group using the eggshell catalyst, and to the use of the eggshell catalyst for hydrogenating an organic compound.
    Type: Application
    Filed: December 14, 2010
    Publication date: November 22, 2012
    Applicant: BASF SE
    Inventors: Lucia Königsmann, Daniela Mirk, Thomas Heidemann, Michael Hesse, Martin Bock, Mario Emmeluth, Jutta Bickelhaupt
  • Publication number: 20120289747
    Abstract: The present invention relates to a catalyst comprising 4% by weight of ruthenium (Ru) or more and a support material comprising silicon dioxide, wherein the nitrogen content of the catalyst after the last drying or calcination is in the range from 1 to 3% by weight, and also catalyst precursors thereof. The present patent application further relates to a process for producing an Ru-comprising catalyst, which comprises the steps impregnation, drying, calcination and reduction. In addition, the present patent application relates to a process for hydrogenating organic substances in the presence of catalysts of the invention or catalysts produced according to the invention, and also a process for producing downstream products from cycloaliphatic amines prepared according to the invention.
    Type: Application
    Filed: May 10, 2012
    Publication date: November 15, 2012
    Applicant: Carl-Bosch-Strasse 38
    Inventors: Lucia Königsmann, Thomas Heidemann, Martin Bock, Joachim Pfeffinger, Benjamin Koch
  • 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
  • Publication number: 20110251431
    Abstract: Process for preparing bis(para-amino-cyclohexyl)methane by multiphase reaction of methylenedianiline with hydrogen, in which the reaction is performed in 5 to 50 series-connected reaction zones under adiabatic conditions.
    Type: Application
    Filed: December 4, 2009
    Publication date: October 13, 2011
    Applicant: Bayer Technology Services GMBH
    Inventors: Evin Hizaler Hoffmann, Leslaw Mleczko, Ralph Schellen, Stephan Schubert
  • Publication number: 20100125151
    Abstract: Disclosed is a process for the preparation of 1,2-cycloaliphatic diamines from 1,2-aromatic diamines. In one embodiment, the process provides a method for making 1,2-diaminocyclohexane by the reaction of 1,2-phenylenediamine contained in a polar, protic solvent with hydrogen in the presence of a supported rhodium catalyst, ammonia, and an inorganic borohydride, and having enhanced overall conversion and selectivity.
    Type: Application
    Filed: November 4, 2009
    Publication date: May 20, 2010
    Applicant: INVISTA NORTH AMERICA S.A.R.L.
    Inventor: RONALD L. AMEY
  • Patent number: 7682408
    Abstract: The present invention relates to a dyestuff of the formula (I) wherein each of G1 and G2, independently is hydrogen, (C1-C4)-alkyl, trifluoromethyl, halogen, nitro, cyano or —SO2—T, wherein T is halogen, (C1-C4)-alkyl, (C1-C4)-alkoxy, aryl or aryloxy; K is a coupling component; and n is 1 or 2. The invention also relates to a process for its preparation and their use and for ink jet printing containing the ink.
    Type: Grant
    Filed: March 2, 2007
    Date of Patent: March 23, 2010
    Assignee: Dy Star Textilfarben GmbH & Co.
    Inventors: Andreas Endres, Rainer Hamprecht, Hartwig Jordan, Anthony Lawrence, Nigel Hall
  • Publication number: 20090253938
    Abstract: A process for preparing 1,2-diamino-3-methylcyclohexane and/or 1,2-diamino-4-methylcyclohexane by reacting 2,3- and/or 3,4-diaminotoluene with hydrogen at elevated pressure and elevated temperature in the presence of a heterogeneous rhodium catalyst, wherein a mixture comprising 2,3- and/or 3,4-diaminotoluene, a dialkyl ether and/or alicyclic ether as a solvent and ammonia is initially charged in an autoclave in the presence of the catalyst and subsequently hydrogenated while supplying hydrogen.
    Type: Application
    Filed: December 14, 2005
    Publication date: October 8, 2009
    Applicant: BASF AKTIENGESELLSCHAFT
    Inventors: Friederike Osswald, Karl Heinz Brauch, Arnd Bottcher, Jochem Henkelmann, Frederik Van Laar, Till Gerlach
  • Patent number: 7465833
    Abstract: The present invention relates to processes for the catalytic hydrogenation of aromatic amines to their acyclic counterparts using a ruthenium catalyst on a lithium aluminate support. The hydrogenation process comprises contacting an aromatic amine with hydrogen in the presence of a ruthenium catalyst under temperature and pressure conditions suitable to effect ring hydrogenation. The process is especially useful for hydrogenating aniline to cyclohexylamine.
    Type: Grant
    Filed: September 22, 2005
    Date of Patent: December 16, 2008
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Gamini Ananda Vedage, Hao Ding, Matthew J. Engel, Eugene George Lutz, Lenore Ann Emig
  • Patent number: 7390869
    Abstract: A process for removing metal species from a composition comprising contacting: a. an oligomer mixture stream comprising the monomers of a partially aromatic polyester polymer and at least one metal species, or b. a molten polyester polymer stream comprising partially aromatic polyester polymers and at least one metal species, with a non-catalytic porous material in the presence of hydrogen to produce a treated stream containing a reduced amount of at least one metal species. There is also provided a composition comprising a partially aromatic polyester polymer having an It.V. of at least 0.50 produced in a direct esterification melt phase process, from greater than 0 to less than 50 ppm antimony, and less than 40 ppm cobalt. There is also provided a composition comprising partially aromatic polyester polymers having an It.V. of at least 0.50 produced in an ester exchange melt phase process, from greater than zero to less than 5 ppm titanium, and less than 10 ppm manganese.
    Type: Grant
    Filed: June 13, 2005
    Date of Patent: June 24, 2008
    Assignee: Eastman Chemical Company
    Inventors: Zhufang Liu, Jeff Scott Howell
  • Patent number: 7355084
    Abstract: In a process for hydrogenating at least one organic compound, the organic compound or compounds is/are brought into contact with a hydrogen-containing gas in the presence of a catalyst which comprises, as active metal, ruthenium either alone or together with at least one further metal of transition group I, VII or VIII of the Periodic Table applied to a support material based on amorphons silicon dioxide and is obtainable by: i) a single or multiple treatment of a support material based on amorphous silicon dioxide with a halogen-free aqueous solution of a low molecular weight ruthenium compound and subsequent drying of the treated support material at below 200° C., ii) reduction of the solid obtained in i) by means of hydrogen at from 100 to 350° C., with step ii) being carried out directly after step i).
    Type: Grant
    Filed: June 7, 2002
    Date of Patent: April 8, 2008
    Assignee: BASF Aktiengesellschaft
    Inventors: Arnd Böttcher, Dominic Vanoppen, Jan-Dirk Arndt, Jochem Henkelmann, Konrad Knoll
  • Patent number: 7304183
    Abstract: Embodiments of the present invention disclose a process for the co-production of bis(para-aminocyclohexyl) methane (PACM). Also disclosed are articles of manufacture made using PACM produced by methods of this invention. The methods of the present invention generally include a first mixture having methylene di-aniline (MDA) and a second aromatic amine. The first mixture has less than 15% polymeric MDA by weight and the second aromatic amine is present in an amount to render the first mixture a liquid. The first mixture is hydrogenated to produce a product mixture comprising PACM and at least one second non-aromatic amine.
    Type: Grant
    Filed: December 15, 2005
    Date of Patent: December 4, 2007
    Assignee: Huntsman Petrochemical Corporation
    Inventors: Wei-Yang Su, Ralph M. DiGuilio, Pete S. Morford
  • Patent number: 7091384
    Abstract: The invention relates to a process for increasing the selectivity of the hydrogenation of 4,4?-diaminodiphenylmethane (4,4?-MDA) to diaminodicyclohexylmethane (4,4?-HMDA) by catalytic hydrogenation of a mixture containing 4,4?-MDA as the main component and its mono-N-methyl derivative as a secondary component. According to the invention, the hydrogenation is terminated before a conversion of 4,4?-MDA to 4,4?-HMDA of 99% is achieved. Under these conditions, a substantially smaller proportion of the N-methyl-4,4?-MDA is hydrogenated to N-methyl-4,4-HMDA.
    Type: Grant
    Filed: June 25, 2003
    Date of Patent: August 15, 2006
    Assignee: Degussa AG
    Inventors: Bernd Jaeger, Thomas Haas, Guido Stochniol, Christian Lettmann, Willi Hofen, Klaus Stadtmueller, Joerg Lotz
  • Patent number: 7067615
    Abstract: A process comprising contacting a liquid polyester stream with hydrogen in the presence of a hydrogenation catalyst comprising a metal supported on the surface of silicon carbide at a metal dispersion of at least 0.5% or graphite at a metal dispersion of at least 10% to produce a treated liquid polyester stream. The treated stream may be polycondensed in the presence of a polycondensation catalyst to produce a polyester polymer having an It.V. of at least 0.55 dL/g. The liquid polyester stream desirably has a composition comprising: a) terephthalic acid residues, isophthalic acid residues, and/or naphthalenedicarboxylic acid residues and b) an average degree of polymerization of 0.5 to 20 and c) an acid number ranging from 5 to 600.
    Type: Grant
    Filed: June 13, 2005
    Date of Patent: June 27, 2006
    Assignee: Eastman Chemical Company
    Inventors: Zhufang Liu, Jeff Scott Howell, Charles Edwan Sumner, Jr.
  • Patent number: 7038088
    Abstract: This invention relates to a process for the catalytic hydrogenation of impurity laden methylenedianiline feedstocks commonly referred to a MDA-50 and MDA-60. The process for hydrogenating methylenedianiline containing at least 40% oligomer function by weight comprises: contacting the feedstock with hydrogen in the presence of a rhodium/ruthenium containing catalyst system carried on a lithium aluminate support under conditions for effecting ring hydrogenation.
    Type: Grant
    Filed: May 19, 2004
    Date of Patent: May 2, 2006
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Hao Ding, Gamini Ananda Vedage, William R. Martine, Vipul P. Dholakia
  • Patent number: 6998507
    Abstract: The invention is directed to an improvement in a catalytic process for the ring hydrogenation of a methylenedianiline feedstock, including crude methylenedianiline. One component of the improvement is a pretreatment process which resides in passing the crude methylenedianiline feedstock over a ruthenium catalyst carried on a fixed bed support, cooling without venting, and then hydrogenation of the pretreated crude methylenedianiline feedstock over a rhodium catalyst or a mixed Rh/Ru catalyst carried on a monolith support and carrying out the ring hydrogenation in a batch reaction. Another component in the improvement is the employment of a catalyst comprised of rhodium and ruthenium carried on a monolith support.
    Type: Grant
    Filed: August 24, 2004
    Date of Patent: February 14, 2006
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Hao Ding, Anthony Rocco Cartolano, Vipul P. Dholakia, Gamini Ananda Vedage
  • 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: 6962964
    Abstract: This invention relates to improved polyepoxide resins cured with a mixture of methylene bridged poly(cycloaliphatic-aromatic)amines and a process for preparing such polyepoxide resins as well as to the methylene bridged poly(cycloaliphatic-aromatic)amine compositions and a method of making them. The improvement resides in using a curative (herein referred to as “Heavy MPCA”) comprised of the partially hydrogenated condensation product of formaldehyde and aniline or methyl substituted aniline containing a substantial amount (from 35 to 85% by weight, preferably 40 to 60% by weight) of oligomers in the form of 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 and 15 aniline or methyl substituted aniline derivatives.
    Type: Grant
    Filed: February 6, 2003
    Date of Patent: November 8, 2005
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Michael Ulman, Gamini Ananda Vedage, David Alan Dubowik, Stephen Michael Boyce
  • Patent number: 6924385
    Abstract: The invention relates to a method for synthesis of aliphatic isocyanates from aromatic isocyanates in substantially 3 stages. In particular, the invention relates to a method for synthesis of bis{4-isocyanatocyclohexyl}methane (H12MDI) from bis{4-isocyanatophenyl}methane (MDI). More especially, the invention relates to a method for synthesis of H12MDI with a trans-trans isomer content of <30%, preferably of <20%, particularly preferably of 5 to 15%.
    Type: Grant
    Filed: December 31, 2002
    Date of Patent: August 2, 2005
    Assignee: Degussa AG
    Inventors: Christian Lettmann, Stephan Kohlstruk, Guido Stochniol, Emmanouil Spyrou
  • Publication number: 20040162287
    Abstract: Substituted cyclohexane-1,4-diamine compounds, methods for production thereof, pharmaceutical compositions comprising these compounds and methods of treatment using these compounds.
    Type: Application
    Filed: November 10, 2003
    Publication date: August 19, 2004
    Applicant: GRUENENTHAL GmbH
    Inventors: Bernd Sundermann, Hagen-Heinrich Hennies, Werner Englberger, Babette-Yvonne Koegel
  • Patent number: 6504060
    Abstract: The invention relates to a process for the preparation of diaminodicyclohexylmethane (“PACM”) with a proportion of trans,trans-4,4′-diaminodicyclohexylmethane of from 17 to 24% by hydrogenation of diaminodiphenylmethane (“MDA”) in the presence of a pulverulent catalyst in a continuously operated suspension reactor at a conversion of MDA of at least 95%, based on the amount of MDA used.
    Type: Grant
    Filed: April 15, 2002
    Date of Patent: January 7, 2003
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rolf Bunnenberg, Andreas Gröschl, Michael Holzbrecher, Andreas Schulze Tilling
  • Publication number: 20020198409
    Abstract: The invention relates to a process for the preparation of diaminodicyclohexylmethane (“PACM”) with a proportion of trans,trans-4,4′-diaminodicyclohexylmethane of from 17 to 24% by hydrogenation of diaminodiphenylmethane (“MDA”) in the presence of a pulverulent catalyst in a continuously operated suspension reactor at a conversion of MDA of at least 95%, based on the amount of MDA used.
    Type: Application
    Filed: April 15, 2002
    Publication date: December 26, 2002
    Inventors: Rolf Bunnenberg, Andreas Groschl, Michael Holzbrecher, Andreas Schulze Tilling
  • Publication number: 20020183556
    Abstract: The invention relates to ruthenium catalysts for the hydrogenation of diaminodiphenylmethane to diaminodicyclohexylmethane, particularly with a proportion of trans,trans-4,4′-diaminodicyclohexylmethane of from 17 to 24%, in a continuously operated suspension reactor, where ruthenium is applied to a support of high-purity aluminum oxide that preferably has a sodium content of less than 0.05% by weight, a particle size of from 5 to 150 &mgr;m, and a BET specific surface area of from 30 to 300 m2/g.
    Type: Application
    Filed: April 15, 2002
    Publication date: December 5, 2002
    Inventors: Andreas Schulze Tilling, Thomas Prinz, Jurgen Kintrup
  • Patent number: 6429338
    Abstract: This invention relates to an improved process for the preparation of cyclohexylamines wherein an aromatic amine is contacted with hydrogen in the presence of a hydrogenation catalyst. The improvement resides in utilizing a hydrogenation catalyst comprised of rhodium metal, utilizing a dialkyl ether solvent, and effecting delay addition of the aromatic diamine to the reaction medium.
    Type: Grant
    Filed: January 17, 2002
    Date of Patent: August 6, 2002
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Juan Jesus Burdeniuc, Gamini Ananda Vedage, Bradley Heath Cook
  • Patent number: 6248924
    Abstract: A process for the reaction of an organic compound in the presence of a catalyst comprising, as active metal, ruthenium alone or together with at least one Group Ib, VIIb, or VIIIb metal in an amount of from 0.01 to 30 wt %, based on the total weight of the catalyst, applied to a support, wherein from 10 to 50% of the pore volume of the support comprises macropores having a pore diameter in the range of from 50 nm to 10,000 nm and from 50 to 90% of the pore volume of the support comprises mesopores having a pore diameter in the range of from 2 to 50 nm, the sum of said pore volumes being 100%, and said catalyst as such.
    Type: Grant
    Filed: June 16, 1997
    Date of Patent: June 19, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Thomas Rühl, Boris Breitscheidel, Jochem Henkelmann, Andreas Henne, Rolf Lebkücher, Konrad Knoll, Paul Naegele, Hermann Gausepohl, Sabine Weiguny, Norbert Niessner
  • Publication number: 20010000035
    Abstract: A process for the reaction of an organic compound in the presence of a catalyst comprising, as active metal, ruthenium alone or together with at least one Group Ib, VIIb, or VIIIb metal in an amount of from 0.01 to 30 wt %, based on the total weight of the catalyst, applied to a support, wherein from 10 to 50% of the pore volume of the support comprises macropores having a pore diameter in the range of from 50 nm to 10,000 nm and from 50 to 90% of the pore volume of the support comprises mesopores having a pore diameter in the range of from 2 to 50 nm, the sum of said pore volumes being 100%, and said catalyst as such.
    Type: Application
    Filed: November 30, 2000
    Publication date: March 15, 2001
    Inventors: Thomas Ruhl, Boris Breitscheidel, Jochem Henkelmann, Andreas Henne, Rolf Lebkucher, Konard Knoll, Paul Naegele, Hermann Gausepohl, Sabine Weiguny, Norbert Niessner
  • Patent number: 6184416
    Abstract: This invention relates to an improvement in a process for the catalytic hydrogenation of aromatic amines and to the resultant catalyst. The basic process for hydrogenating both mononuclear and polynuclear aromatic amines comprises contacting an aromatic amine with hydrogen in the presence of a rhodium catalyst under conditions for effecting ring hydrogenation. The improvement in the ring hydrogenation process resides in the use of a rhodium catalyst carried on a lithium aluminate support. Often ruthenium is included.
    Type: Grant
    Filed: April 28, 2000
    Date of Patent: February 6, 2001
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Hao Ding, John Nelson Armor, Lenore Ann Emig, Dorai Ramprasad, Gamini Ananda Vedage, Frederick Carl Wilhelm
  • Patent number: 6140540
    Abstract: This invention relates to an improved hydrogenation and isomerization process wherein aromatic amines are hydrogenated to their ring hydrogenated counterparts and substantially isomerized to their thermodynamic form. These aromatic amines are presented by the formulas: ##STR1## wherein R is hydrogen or C.sub.1-6 alkyl, R1 and R2 are hydrogen or C.sub.1-6 aliphatic, A is C.sub.1-4 or NH; n is 0-2, x is 1-3 and y is 0 to 2 except the sum of the y groups must be at least 1.
    Type: Grant
    Filed: April 6, 1993
    Date of Patent: October 31, 2000
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Gamini Ananda Vedage, Richard Scott Myers, John Nelson Armor
  • Patent number: 6077975
    Abstract: A low-pressure process for the hydrogenation of aromatic amines to give the corresponding symmetrical dicycloaliphatic amines in the presence of rhodium catalysts which are unmodified or modified by Ir, Ru, Os, Pd and/or Pt or mixtures of these metals, on supports modified by oxides of Cr, Mo, W, Mn and/or Re or mixtures of these oxides.
    Type: Grant
    Filed: September 28, 1999
    Date of Patent: June 20, 2000
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reinhard Langer, Gerd-Michael Petruck
  • Patent number: 6075167
    Abstract: This invention relates to a method for preparing cycloaliphatic diamines by hydrogenating aromatic diamines in the presence of a supported ruthenium catalyst and a metal nitrite as a catalyst promoter to increase the rate of the hydrogenation reaction and decrease the amount of higher boiler by-products.
    Type: Grant
    Filed: September 25, 1998
    Date of Patent: June 13, 2000
    Assignee: Korea Institute of Science and Technology
    Inventors: Hoon Sik Kim, Kun Yu Park, Young Soo Kwon, Moon Jo Chung, Byung Gwon Lee
  • Patent number: 6054619
    Abstract: The present invention relates to a low-pressure process for hydrogenating aromatic amines to give the corresponding cycloaliphatic amines in the presence of rhodium catalysts.
    Type: Grant
    Filed: June 14, 1999
    Date of Patent: April 25, 2000
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reinhard Langer, Gerd-Michael Petruck
  • Patent number: 5981801
    Abstract: This invention relates to a method for preparing cycloaliphatic diamines by hydrogenating an aromatic diamines in the presence of a supported ruthenium catalyst. The catalyst is pre-treated with oxygen or air to increase the rate of the reaction and decrease the amount of higher boiler by-products.
    Type: Grant
    Filed: September 25, 1998
    Date of Patent: November 9, 1999
    Assignee: Korea Institute of Science and Technology
    Inventors: Hoon Sik Kim, Hyunjoo Lee, Sang Hyun Seo, Honggon Kim, Dong Ju Moon
  • Patent number: 5973207
    Abstract: This invention relates to an improved process for the preparation of methylcyclohexane diamine wherein meta-toluenediamine is contacted with hydrogen in the presence of a hydrogenation catalyst. The improvement resides in utilizing a hydrogenation catalyst comprising rhodium carried on a support and carrying out the hydrogenation in the presence of a C.sub.3 -C.sub.10 secondary alcohol as a solvent. With the use of rhodium carried on a support as a catalyst, coupled with the use of the secondary alcohol solvent, one obtains high yields with excellent catalyst life.
    Type: Grant
    Filed: September 27, 1993
    Date of Patent: October 26, 1999
    Assignee: Air Products and Chemicals, Inc.
    Inventor: Gamini Ananda Vedage
  • Patent number: 5936126
    Abstract: A process for the hydrogenation of an aromatic compound, in which at least one hydroxyl group is attached to an aromatic core, or an aromatic compound, in which at least one amino group is attached to an aromatic core, in the presence of a catalyst containing, as active metal, ruthenium and optionally one or more other Group IB, VIIB, or VIIIB metals, applied to a macroporous support.
    Type: Grant
    Filed: June 18, 1997
    Date of Patent: August 10, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Thomas Ruhl, Boris Breitscheidel, Jochem Henkelmann, Wolfgang Reif, Helmuth Menig, Sabine Weiguny
  • Patent number: 5874622
    Abstract: In a process for hydrogenating an aromatic compound in which at least one hydroxyl group is bonded to an aromatic ring or an aromatic compound in which at least one amino group is bonded to an aromatic ring, in the presence of a catalyst comprising as catalytically active component at least one metal of transition group I, VII or VIII of the Periodic Table applied to a support, the catalyst is obtainable bya) dissolving the catalytically active component or a precursor compound thereof in a solvent,b) admixing the solution thus obtained with an organic polymer which is able to bind at least ten times its own weight of water, giving a swollen polymer,c) subsequently mixing the swollen polymer with a catalyst support material andd) shaping, drying and calcining the composition obtained in this way.
    Type: Grant
    Filed: December 9, 1997
    Date of Patent: February 23, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Boris Breitscheidel, Thomas Ruhl, Klemens Flick, Jochem Henkelmann, Andreas Henne, Rolf Lebkucher
  • Patent number: 5773657
    Abstract: Aromatic compounds in which at least one amino group is bonded to an aromatic nucleus are catalytically hydrogenated in the liquid phase by a process in which the catalyst consists essentially of ruthenium and, optionally at least one metal of subgroup I, VII or VIII in an amount of from 0.01 to 30% by weight, based on the total weight of the catalyst, applied to a carrier which has a mean pore diameter of at least 0.1 .mu.m and a surface area of not more than 15 m.sup.2 /g.
    Type: Grant
    Filed: August 23, 1996
    Date of Patent: June 30, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Heinz Rutter, Thomas Ruhl, Boris Breitscheidel, Jochem Henkelmann, Andreas Henne, Thomas Wettling
  • 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: 5741929
    Abstract: For the continuous preparation of a mixture of amino-methyl-cyclohexanes and diamino-methyl-cyclohexanes by catalytic hydrogenation of diamino-toluenes with hydrogen at temperatures of from 150.degree. to 260.degree. C. and an H.sub.2 pressure of from 20 to 500 bar, use is made of a fixed-bed catalyst comprising ruthenium on an Al.sub.2 O.sub.3 support treated with compounds of rare earth metals, of manganese and alkali metal hydroxides or alkaline earth metal hydroxides.
    Type: Grant
    Filed: March 10, 1997
    Date of Patent: April 21, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Darsow, Gerd-Michael Petruck
  • Patent number: 5739404
    Abstract: For the continuous preparation of a mixture of amino-methyl-cyclohexanes and diamino-methyl-cyclohexanes by catalytic hydrogenation of diamino-toluenes with hydrogen at temperatures of from 150.degree. to 260.degree. C. and an H.sub.2 pressure of from 20 to 500 bar, use is made of reduced support-free catalysts which are produced from pressed powders of cobalt, manganese, copper and alkaline earth metal (hydr)oxides, with or without a content of at least one (hydr)oxide of metals of transition group V and/or VI of the Periodic Table of the Elements (Mendeleev).
    Type: Grant
    Filed: March 20, 1997
    Date of Patent: April 14, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Darsow, Gerd-Michael Petruck
  • Patent number: 5684180
    Abstract: The invention relates to a process for the fractionation and purification of aromatic polyamine mixtures and to the use thereof.
    Type: Grant
    Filed: March 28, 1996
    Date of Patent: November 4, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hartmut Knofel, Michael Brockelt
  • Patent number: 5679840
    Abstract: The invention relates to a process for the fractionation and purification of aromatic polyamine mixtures and their use.
    Type: Grant
    Filed: March 28, 1996
    Date of Patent: October 21, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hartmut Knofel, Michael Brockelt
  • Patent number: 5679841
    Abstract: The invention relates to a process for the fractionation and purification of aromatic polyamine mixtures and the use thereof.
    Type: Grant
    Filed: March 28, 1996
    Date of Patent: October 21, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hartmut Knofel, Michael Brockelt