Preparing Alicyclic Ring Containing Compound Directly By Hydrogenating Benzene Ring Patents (Class 564/450)
  • Patent number: 10336668
    Abstract: A process for preparing trans-enriched MDACH, including: distilling an MDACH starting mixture in the presence of an auxiliary, which is an organic compound having a molar mass of 62 to 500 g/mol, a boiling point at least 5° C. above the boiling point of cis,cis-2,6-diamino-1-methylcyclohexane, and 2 to 4 functional groups, each of which is independently an alcohol group or a primary, secondary or tertiary amino group. The MDACH starting mixture includes 0 to 100% by weight of 2,4-MDACH and 0 to 100% by weight of 2,6-MDACH, based on the total amount of MDACH present in the MDACH starting mixture. The MDACH starting mixture includes both trans and cis isomers. Trans-enriched MDACH includes 0 to 100% by weight of 2,4-MDACH and 0 to 100% by weight of 2,6-MDACH, where the proportion of trans isomers in the mixture is higher than the proportion of trans isomers in the MDACH starting mixture.
    Type: Grant
    Filed: November 18, 2015
    Date of Patent: July 2, 2019
    Assignee: BASF SE
    Inventors: Jan-Oliver Weidert, Sandra Kramp, Regina Benfer, Alexander Panchenko, Andreas Weickgenannt, Norbert Gutfrucht, Klaus Breuer, Artur Kozicki, Ralph Busch
  • 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
  • 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: 20110137083
    Abstract: The present invention relates to a continuous process for hydrogenating organic compounds in a polyphasic system in the presence of a homogeneous or heterogeneous catalyst, which comprises performing the process in two stages, the first stage being performed in a loop reactor with an external heat exchanger and the second stage in a bubble column reactor with limited backmixing.
    Type: Application
    Filed: May 20, 2009
    Publication date: June 9, 2011
    Applicant: BASF SE
    Inventor: Joachim Pfeffinger
  • Publication number: 20100204518
    Abstract: The invention relates to a novel thermostable palladium catalyst, a method for producing the same and the use thereof in hydrogenation reactions, especially hydrogenations of nitro compounds.
    Type: Application
    Filed: September 9, 2008
    Publication date: August 12, 2010
    Applicant: BAYER TECHNOLOGY SERVICES GMBH
    Inventors: Aurel Wolf, Leslaw Mleczko, Jens Assmann, Frank Rauscher
  • Patent number: 7507862
    Abstract: The invention relates to a process for hydrogenating an aromatic amine that has at least one amino group bound to an aromatic nucleus with hydrogen in the presence of a supported catalyst that contains at least ruthenium as active metal. The catalyst support has a BET surface area in the range from greater than 30 m2/g to less than 70 m2/g and more than 50% of the pore volume of the catalyst support is formed by macropores having a pore diameter of greater than 50 nm and less than 50% are mesopores having a pore diameter of 2 to 50 nm.
    Type: Grant
    Filed: November 23, 2005
    Date of Patent: March 24, 2009
    Assignee: Degussa AG
    Inventors: Guido Stochniol, Bernd Jaeger, Thomas Haas, Norbert Finke, Werner Burkhardt, Juergen Grunert
  • 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
  • Publication number: 20080139850
    Abstract: Compounds containing phenolic hydroxy groups are removed from a gas stream which contains at least one aromatic amine generated during the gas-phase hydrogenation reaction of the corresponding nitroaromatic compounds with hydrogen, by adsorption on a basic solid.
    Type: Application
    Filed: November 6, 2007
    Publication date: June 12, 2008
    Inventors: Knut Sommer, Markus Dugal, Ido Schwarz, Stefan Wershofen, Peter Lehner, Stephan Schubert, Alexandra Grosse-Bowing
  • 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: 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: 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: 20040034252
    Abstract: The invention relates to a process for hydrogenating an aromatic amine that has at least one amino group bound to an aromatic nucleus with hydrogen in the presence of a supported catalyst that contains at least ruthenium as active metal. The catalyst support has a BET surface area in the range from greater than 30 m2/g to less than 70 m2/g and more than 50% of the pore volume of the catalyst support is formed by macropores having a pore diameter of greater than 50 nm and less than 50% are mesopores having a pore diameter of 2 to 50 nm.
    Type: Application
    Filed: June 2, 2003
    Publication date: February 19, 2004
    Applicant: Degussa AG
    Inventors: Guido Stochniol, Bernd Jaeger, Thomas Haas, Norbert Finke, Werner Burkhardt, Juergen Grunert
  • 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: 6335470
    Abstract: Ru/Pd catalysts on supports are used for the preparation of mixtures of substituted or unsubstituted cyclohexylamine and substituted or unsubstituted dicyclohexylamine in variable amounts by catalytic hydrogenation of substituted or unsubstituted aniline at elevated temperature and elevated H2 pressure. These catalysts are characterized in that they contain no halogen or sulphur compounds.
    Type: Grant
    Filed: June 2, 2000
    Date of Patent: January 1, 2002
    Inventors: Gerhard Darsow, Reinhard Langer
  • Patent number: 6255530
    Abstract: Six-membered ring carbocycles of the formula (II) can be prepared by ring hydrogenation of aromatic compounds of the formula (I) the definitions for which are given in the description, in a reaction system consisting of two liquid, immiscible phases in which elemental hydrogen is dispersed. The first phase consists of the aromatic compound (I) and, if necessary, a water-immiscible solvent. The second phase is essentially aqueous and comprises, colloidally dispersed therein, a hydrogenation-active metal as hydrogenation catalyst, and auxiliaries for stabilizing the colloidal catalyst. The process is carried out at from 50 to 180° C. and from 1 bar to 400 bar.
    Type: Grant
    Filed: February 22, 1999
    Date of Patent: July 3, 2001
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rolf William Albach, Manfred Jautelat
  • 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: 6166234
    Abstract: Novel tripodal cyclopentadiene derivatives have the formula (I) ##STR1## where E are identical or different and are --N(R)(R), --P(R)(R), --As(R)(R), --Sb(R)(R), --OR, --SR, --SeR, --TeR, where R are identical or different and are each hydrogen, a C.sub.1 -C.sub.20 -carboorganic radical or a C.sub.1 -C.sub.30 -organosilicon radical, or E is a leaving group X andR.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 are identical or different and are each hydrogen, a C.sub.1 -C.sub.20 -carboorganic radical or a C.sub.1 -C.sub.30 -organosilicon radical,Z is a cyclopentadienyl radical or a substituted cyclopentadienyl structural unit andT is hydrogen, a C.sub.1 -C.sub.20 -carboorganic radical or a C.sub.1 -C.sub.30 -organosilicon radical or a group E--Y--, where E is --N(R)(R), --P(R)(R), --As(R)(R), --Sb(R)(R), --OR, --SR, --SeR, --TeR or a leaving group X, where R are identical or different and are each hydrogen, a C.sub.1 -C.sub.20 -carboorganic radical or a C.sub.1 -C.sub.
    Type: Grant
    Filed: January 13, 1998
    Date of Patent: December 26, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Gottfried Huttner, Joachim Vogelgesang, Ute Winterhalter, Bjorn Antelmann
  • 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: 6111140
    Abstract: Catalysts containing ruthenium and palladium for the hydrogenation of aromatic amines to cycloaliphatic amines. Methods for making and using the catalysts.
    Type: Grant
    Filed: April 5, 1999
    Date of Patent: August 29, 2000
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Josef Buysch, Gerhard Darsow, Otto Immel, Reinhard Langer
  • 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: 6043395
    Abstract: A high-pressure process for hydrogenating aromatic amines to give mixtures of the corresponding cycloaliphatic amines and dicycloaliphatic amines in variable ratios in the presence of rhodium catalysts.
    Type: Grant
    Filed: June 1, 1999
    Date of Patent: March 28, 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: 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: 5728883
    Abstract: In the preparation of a mixture of cyclohexylamine and dicyclohexylamine by catalytic hydrogenation of aniline at elevated temperature and elevated H.sub.2 pressure, use is made of reduced, support-free catalysts which comprise pressed element (hydr)oxide powders of Co, Mn, alkaline earth metals and element (hydr)oxide powders of elements of transition groups V and/or VI of the Periodic Table.
    Type: Grant
    Filed: February 5, 1997
    Date of Patent: March 17, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Darsow, Wilfried Niemeier, Gerd-Michael Petruck
  • Patent number: 5714635
    Abstract: The present invention is related to a method for preparation of cyclohexylamine by hydrogenating aniline at a temperature of 150.degree. to 250.degree. C. under a hydrogen pressure of 1 to 20 atm in the presence of a catalyst selected from a chromium- or thorium- modified cobalt boride, wherein the amount of said modified cobalt boride is at least 0.6 wt % based on the weight of aniline.Compared with the prior art which used a conventional hydrogenation catalyst such as ruthenium, palladium, Raney cobalt or Raney nickel, the method adopted by the present invention has the advantages in that it can be performed under a relatively lower hydrogen pressure without necessity of adding any coupling inhibitors and a much higher aniline conversion and a higher or comparable selectivity to cyclohexylamine can be obtained, thus resulting in greatly increased yield of cyclohexylamine.
    Type: Grant
    Filed: November 25, 1996
    Date of Patent: February 3, 1998
    Assignee: San Fu Chemical Co., Ltd.
    Inventors: Yin-Zu Chen, Zhang-Feng Yang, I-Hui Chen
  • Patent number: 5705700
    Abstract: To prepare a mixture of cyclohexylamine and dicyclohexylamine by catalytic hydrogenation of aniline at elevated temperature and elevated H.sub.2 pressure, the catalyst system used comprises two reduced, unsupported catalysts A and B which are prepared from pressed element (hydr)oxide powders. Catalyst A comprises one or more of Fe, Co, Ni, also Mn, Cu and one or more of Ca, Sr, Ba. Catalyst B comprises one or more of Fe, Co, Ni, also Mn, Si and Mg.
    Type: Grant
    Filed: November 22, 1996
    Date of Patent: January 6, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Darsow, Gerd-Michael Petruck, Wilfried Niemeier
  • 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
  • Patent number: 5675035
    Abstract: The invention relates to a process for the fractionation and purification of aromatic polyamine mixtures and to their use.
    Type: Grant
    Filed: March 28, 1996
    Date of Patent: October 7, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hartmut Knofel, Michael Brockelt
  • Patent number: 5672737
    Abstract: The invention relates to a process for the fractionation and purification of mixtures of aromatic polyamines and to the use thereof.
    Type: Grant
    Filed: March 28, 1996
    Date of Patent: September 30, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hartmut Knofel, Michael Brockelt
  • Patent number: 5665756
    Abstract: Novel aminoalkyloximes of the formula ##STR1## wherein: a. X is hydrogen, loweralkyl, loweralkoxy, halogen, trifluoromethyl, or a group of the formula ##STR2## wherein Y is hydrogen or loweralkyl, and p is 1 or 2; b. A is a group of the formula ##STR3## c. R.sup.1 and R.sup.2 are independently hydrogen or lowerakyl; and d. m is 2 to 6 and n is 0, or 2 to 6, inclusive, serotonin reuptake inhibitors, useful for treating depression and obsessive compulsive disorders are described. Also described are precursors of and processes for the preparation of such aminoakyloximes.
    Type: Grant
    Filed: August 3, 1994
    Date of Patent: September 9, 1997
    Assignee: Hoechst Marion Roussel, Inc.
    Inventors: Gregory M. Shutske, Brian S. Freed, John D. Tomer, IV, R. Richard L. Hamer
  • Patent number: 5663424
    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: September 2, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hartmut Knofel, Michael Brockelt
  • Patent number: 5648520
    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: July 15, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hartmut Knofel, Michael Brockelt
  • Patent number: 5648519
    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: July 15, 1997
    Assignee: Bayer Aktiengesesellschaft
    Inventors: Hartmut Knofel, Michael Brockelt
  • Patent number: 5599997
    Abstract: A process for the hydrogenation of aniline to produce cyclohexyl amine is disclosed wherein the reaction is carried out in a distillation column reactor at a hydrogen partial pressure in the range of 0.1 psia to less than 100 psia. The catalyst is prepared in the form of a catalytic distillation structure. Within the distillation reaction zone there is an internal reflux and liquid from an external reflux which cool the rising vaporous aniline condensing a portion within the bed.
    Type: Grant
    Filed: March 14, 1995
    Date of Patent: February 4, 1997
    Assignee: Chemical Research & Licensing Company
    Inventors: Dennis Hearn, Speros P. Nemphos
  • Patent number: 5550294
    Abstract: A process for increasing the rate of catalytic hydrogenation of aromatic amines by reacting aromatic amines with hydrogen in the presence of a noble metal catalyst, a water miscible organic solvent, lithium hydroxide catalyst promoter, and water in an effective amount to increase the rate of the hydrogenation reaction without an appreciable increase in total amounts of by-products.
    Type: Grant
    Filed: September 16, 1994
    Date of Patent: August 27, 1996
    Assignee: Olin Corporation
    Inventor: Peter J. Whitman
  • Patent number: 5545756
    Abstract: This invention relates to an improved hydrogenation process wherein aromatic amines are hydrogenated to their ring hydrogenated counterparts using an improved rhodium catalyst. The aromatic amines are represented by the formulas: ##STR1## wherein R is hydrogen or C.sub.1-6 aliphatic, R.sub.1 and R.sub.2 are hydrogen or C.sub.1-6 aliphatic, A is C.sub.1-4 alkyl, n is 0 or 1, x is 1-3 and y is 1 to 2 except the sum of the y groups in Formula I excluding A may be 1.The rhodium catalyst is carried on a support selected from the group consisting of TiAl.sub.2 O.sub.5, TiSrO.sub.3 and TiSiO.sub.4.
    Type: Grant
    Filed: September 14, 1994
    Date of Patent: August 13, 1996
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Gamini A. Vedage, John N. Armor