Group Vi Metal Containing Catalyst Utilized Patents (Class 564/421)
  • Patent number: 10584093
    Abstract: The present invention provides a method for preparing aniline compounds, and also provides a kind of catalyst and use thereof. This method for synthesizing an aniline compound in the invention includes following steps: use molybdenum oxide and activated carbon as catalyst, hydrazine hydrate as reducing agent, then reduce aromatic nitro compounds to aniline compounds. This method is green and high efficiency, and easy to be applied in industry.
    Type: Grant
    Filed: September 26, 2018
    Date of Patent: March 10, 2020
    Assignee: Seasons Biotechnology (Taizhou) Co., Ltd.
    Inventors: Qiang Jia, Chi Ma, Tianhua Ma, Zhengwei Yang
  • Patent number: 9029603
    Abstract: A process for preparing alkylated p-phenylenediamine having the steps of reacting aniline and nitrobenzene in presence of a complex base catalyst to obtain 4-aminodiphenylamine intermediates, hydrogenating the 4-aminodiphenylamine intermediates to 4-aminodiphenylamine in presence of a hydrogenation catalyst, and reductively alkylating the 4-aminodiphenylamine to alkylated p-phenylenediamine.
    Type: Grant
    Filed: September 14, 2012
    Date of Patent: May 12, 2015
    Assignee: Jiangsu Sinorgchem Technology Co., Ltd.
    Inventors: Xiaogen Feng, Nongyue Wang, Xiaohui Mao, Ruibiao Yu, Qianwen Cheng
  • Patent number: 9012691
    Abstract: A process has been developed for preparing 2-methoxymethyl-1,4-benzenediamine (IV-a), other compounds of formula (IV), and the salts thereof, all of which may be used as primary intermediates in compositions for dyeing keratin fibers.
    Type: Grant
    Filed: October 25, 2013
    Date of Patent: April 21, 2015
    Assignee: The Procter & Gamble Company
    Inventors: John Michael Gardlik, Monica Jo Patten, Garry Steven Garrett, Bryan Patrick Murphy
  • Patent number: 9012700
    Abstract: The invention relates to a method for producing nitrobenzene, in which crude nitrobenzene is first produced by nitrating benzene and said crude nitrobenzene is then washed in succession in at least one acid wash, in at least one alkaline wash and in at least one neutral wash, at least one additional wash with an aqueous solution of a potassium salt being interposed between the last alkaline wash and the first neutral wash.
    Type: Grant
    Filed: August 29, 2012
    Date of Patent: April 21, 2015
    Assignee: Bayer Intellectual Property GmbH
    Inventors: Thomas Knauf, Michael Merkel
  • Publication number: 20150087862
    Abstract: The present invention relates to A method for producing aromatic amines by the hydrogenation of aromatic nitro compounds. This method comprises: A) supplying aromatic nitro compounds and hydrogen to a reactor and contacting them with a hydrogenation catalyst; and B) stopping the supply of aromatic nitro compounds and hydrogen to the reactor. In addition, B) is carried out by: B1) stopping the supply of aromatic nitro compounds to the reactor such that any remaining aromatic nitro compounds present in the reactor and/or in parts of the installation that are fluidically connected to the reactor upstream react with the hydrogen that is still being supplied to the reactor, and B2) stopping the supply of hydrogen after a predetermined time interval and/or after the concentration of aromatic nitro compounds in the gas flow entering the reactor falls below a predetermined value.
    Type: Application
    Filed: April 12, 2013
    Publication date: March 26, 2015
    Inventors: Michael Merkel, Thomas Knauf, Cliff Andre Peters, Thorsten Schmidt, Karl-Heinz Wilke
  • Patent number: 8889911
    Abstract: Nitro-compounds are hydrogenated with an activated Ni catalyst that is doped during and/or after activation with one or more elements from the list of Mg, Ca, Ba, Ti, Zr, Ce, Nb, Cr, Mo, W, Mn, Re, Fe, Co, Ir, Ni, Cu, Ag, Au, Rh, Ru and Bi whereas the Ni/Al alloy may not, but preferentially can contain prior to activation one or more doping elements from the list of Ti, Ce, V, Cr, Mo, W, Mn, Re, Fe, Ru, Co, Rh, Ir, Pd, Pt and Bi. If the Ni/Al alloy contained one or more of the above mentioned suitable alloy doping elements prior to activation, the resulting catalyst can then be doped with one or more of the elements from the list of Mg, Ca, Ba, Ti, Zr, Ce, V, Nb, Cr, Mo, W, Mn, Re, Fe, Ru, Co, Rh, Ir, Ni, Pd, Pt, Cu, Ag, Au and Bi by their adsorption onto the surface of the catalyst.
    Type: Grant
    Filed: May 29, 2007
    Date of Patent: November 18, 2014
    Assignee: Evonik Degussa GmbH
    Inventors: Daniel Ostgard, Monika Berweiler, Markus Göttlinger, Steffen Laporte, Matthias Schwarz
  • Patent number: 8889910
    Abstract: Nitro-compounds are hydrogenated with an activated Ni catalyst that has an average particle size (APS) less than 25 ?m and is doped with one or more elements from the list of Mg, Ce, Ti, V, Nb, Cr, W, Mn, Re, Fe, Ru, Co, Rh, Ir, Pt, Cu, Ag, Au and Bi via its/their addition to the alloy before activation and/or doped with one or more elements from the list of Mg, Ce, Ti, V, Nb, Cr, W, Mn, Re, Fe, Ru, Co, Rh, Ir, Ni, Cu, Ag, Au and Bi by their adsorption onto the surface of the activated catalyst.
    Type: Grant
    Filed: May 29, 2007
    Date of Patent: November 18, 2014
    Assignee: Evonik Degussa GmbH
    Inventors: Daniel Ostgard, Monika Berweiler, Markus Göttlinger, Steffen Laporte, Matthias Schwarz
  • Patent number: 8871980
    Abstract: An object is to provide a process for providing hydrogen or heavy hydrogens conveniently without the necessity of large-scale equipment and a process capable of performing hydrogenation (protiation, deuteration or tritiation) reaction conveniently without the use of an expensive reagent and a special catalyst. The production process includes a process for producing hydrogen or heavy hydrogens, containing subjecting water or heavy water to mechanochemical reaction in the presence of a catalyst metal, and a process for producing a hydrogenated (protiated, deuterated or tritiated) organic compound, containing subjecting an organic compound and water or heavy water to mechanochemical reaction in the presence of a catalyst metal.
    Type: Grant
    Filed: August 16, 2011
    Date of Patent: October 28, 2014
    Assignee: Shiono Chemical Co., Ltd.
    Inventors: Hironao Sajiki, Yasunari Monguchi, Yoshinari Sawama, Shinichi Kondo
  • Publication number: 20130150623
    Abstract: An object is to provide a process for providing hydrogen or heavy hydrogens conveniently without the necessity of large-scale equipment and a process capable of performing hydrogenation (protiation, deuteration or tritiation) reaction conveniently without the use of an expensive reagent and a special catalyst. The production process includes a process for producing hydrogen or heavy hydrogens, containing subjecting water or heavy water to mechanochemical reaction in the presence of a catalyst metal, and a process for producing a hydrogenated (protiated, deuterated or tritiated) organic compound, containing subjecting an organic compound and water or heavy water to mechanochemical reaction in the presence of a catalyst metal.
    Type: Application
    Filed: August 16, 2011
    Publication date: June 13, 2013
    Applicant: Shiono Chemical Co., Ltd.
    Inventors: Hironao Sajiki, Yasunari Monguchi, Yoshinari Sawama, Shinichi Kondo
  • Publication number: 20120065431
    Abstract: The invention relates to a process for preparing aromatic amines by catalytically hydrogenating the corresponding aromatic nitro compound, which comprises using a copper catalyst with a support comprising SiO2, the SiO2 having been prepared by wet grinding and subsequent spray drying.
    Type: Application
    Filed: May 5, 2010
    Publication date: March 15, 2012
    Applicant: BASF SE
    Inventors: Lucia Koenigsmann, Ekkehard Schwab, Michael Hesse, Christian Schneider, Thomas Heidemann, Celine Liekens, Jutta Bickelhaupt, Dirk Theis
  • Publication number: 20110295039
    Abstract: The invention relates to a process for the continuous preparation of toluenediamine by liquid-phase hydrogenation of dinitrotoluene by means of hydrogen in the presence of a suspended, nickel-comprising catalyst in a reactor with a product isolation unit downstream of the reactor to give a product output from the reactor comprising a liquid phase comprising toluenediamine and dinitrotoluene, in which the nickel-comprising catalyst is suspended, wherein the concentration of dinitrotoluene in the liquid phase of the product output from the reactor in the region between the reactor and the downstream product isolation unit is set to a value in the range from 1 to 200 ppm by weight, based on the total weight of the liquid phase of the product output from the reactor.
    Type: Application
    Filed: May 17, 2011
    Publication date: December 1, 2011
    Applicant: BASF SE
    Inventors: Andreas Raichle, Joana Coelho Tsou, Samuel Neto, Ulrich Penzel, Steffen Oehlenschläger, Michael Zöllinger, Holgar Braunsberg, Stefanie Haase, Johannes Büttner
  • Patent number: 8044244
    Abstract: A process for preparing aromatic amines by catalytic hydrogenation of the corresponding nitro compound in a fluidized-bed reactor, in which a gaseous reaction mixture comprising the nitro compound and hydrogen flows from the bottom upward through a heterogeneous particulate catalyst forming a fluidized bed, wherein the fluidized bed is provided with internals which divide the fluidized bed into a plurality of cells arranged horizontally in the fluidized-bed reactor and a plurality of cells arranged vertically in the fluidized-bed reactor, with the cells having cell walls which are permeable to gas and have openings which ensure an exchange number of the heterogeneous, particulate catalyst in the vertical direction in the range from 1 to 100 liters/hour per liter of reactor volume, is proposed.
    Type: Grant
    Filed: September 14, 2007
    Date of Patent: October 25, 2011
    Assignee: BASF SE
    Inventors: Lothar Seidemann, Lucia Koenigsmann, Christian Schneider, Ekkehard Schwab, Dieter Stuetzer, Celine Liekens
  • Publication number: 20100204517
    Abstract: Nitro-compounds are hydrogenated with an activated Ni catalyst that has an average particle size (APS) less than 25 ?m and is doped with one or more elements from the list of Mg, Ce, Ti, V, Nb, Cr, W, Mn, Re, Fe, Ru, Co, Rh, Ir, Pt, Cu, Ag, Au and Bi via its/their addition to the alloy before activation and/or doped with one or more elements from the list of Mg, Ce, Ti, V, Nb, Cr, W, Mn, Re, Fe, Ru, Co, Rh, Ir, Ni, Cu, Ag, Au and Bi by their adsorption onto the surface of the activated catalyst.
    Type: Application
    Filed: May 29, 2007
    Publication date: August 12, 2010
    Applicant: EVONIK DEGUSSA GMBH
    Inventors: Daniel Ostgard, Monika Berweiler, Markus Gottlinger, Steffen Laporte, Matthias Schwarz
  • Publication number: 20100174116
    Abstract: Nitro-compounds are hydrogenated with an activated Ni catalyst that is doped during and/or after activation with one or more elements from the list of Mg, Ca, Ba, Ti, Zr, Ce, Nb, Cr, Mo, W, Mn, Re, Fe, Co, Ir, Ni, Cu, Ag, Au, Rh, Ru and Bi whereas the Ni/Al alloy may not, but preferentially can contain prior to activation one or more doping elements from the list of Ti, Ce, V, Cr, Mo, W, Mn, Re, Fe, Ru, Co, Rh, Ir, Pd, Pt and Bi. If the Ni/Al alloy contained one or more of the above mentioned suitable alloy doping elements prior to activation, the resulting catalyst can then be doped with one or more of the elements from the list of Mg, Ca, Ba, Ti, Zr, Ce, V, Nb, Cr, Mo, W, Mn, Re, Fe, Ru, Co, Rh, Ir, Ni, Pd, Pt, Cu, Ag, Au and Bi by their adsorption onto the surface of the catalyst.
    Type: Application
    Filed: May 29, 2007
    Publication date: July 8, 2010
    Applicant: EVONIK DEGUSSA GMBH
    Inventors: Daniel Ostgard, Monika Berweiler, Markus Gottlinger, Steffen Laporte, Matthias Schwarz
  • Patent number: 7750188
    Abstract: A method for producing aniline or toluenediamine is disclosed which comprises forming a dispersion comprising hydrogen gas bubbles dispersed in a liquid medium comprising either nitrobenzene or dinitrotoluene, wherein the hydrogen gas bubbles have a mean diameter less than 1 micron; and subjecting the dispersion to hydrogenation reaction promoting conditions comprising pressure less than about 600 kPa and temperature less than about 200° C., whereby at least a portion of the nitrobenzene or dinitrotoluene is hydrogenated to form aniline or toluenediamine, respectively. A system for carrying out the method is also disclosed.
    Type: Grant
    Filed: June 18, 2008
    Date of Patent: July 6, 2010
    Assignee: H R D Corporation
    Inventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
  • Publication number: 20100048955
    Abstract: A process for preparing aromatic amines by catalytic hydrogenation of the corresponding nitro compound in a fluidized-bed reactor, in which a gaseous reaction mixture comprising the nitro compound and hydrogen flows from the bottom upward through a heterogeneous particulate catalyst forming a fluidized bed, wherein the fluidized bed is provided with internals which divide the fluidized bed into a plurality of cells arranged horizontally in the fluidized-bed reactor and a plurality of cells arranged vertically in the fluidized-bed reactor, with the cells having cell walls which are permeable to gas and have openings which ensure an exchange number of the heterogeneous, particulate catalyst in the vertical direction in the range from 1 to 100 liters/hour per liter of reactor volume, is proposed.
    Type: Application
    Filed: September 14, 2007
    Publication date: February 25, 2010
    Applicant: BASF SE
    Inventors: Lothar Seidemann, Lucia Koenigsmann, Christian Schneider, Ekkehard Schwab, Dieter Stuetzer, Celine Liekens
  • Patent number: 7595029
    Abstract: The invention pertains to an improved apparatus comprised of a monolith catalytic reactor having an inlet and an outlet and a static mixer having an inlet and an outlet thereto with the outlet of said static mixer in communication with the inlet of said monolith catalytic reactor. The invention also pertains to an improvement in a process for effecting a reaction in the monolith catalytic reactor wherein a reactant gas and reactant liquid are introduced to the inlet to the monolith catalytic reactor, reacted and, then, the reaction product passed through the outlet of the monolith catalytic reactor.
    Type: Grant
    Filed: February 1, 2005
    Date of Patent: September 29, 2009
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Keith Allen Welp, Anthony Rocco Cartolano, David Joseph Parrillo, Richard Peter Boehme, Reinaldo Mario Machado, Sylvia Caram
  • Patent number: 7504539
    Abstract: The invention is directed to a method of producing one or more 4-aminodiphenylamine intermediates comprising the steps: a. bringing an aniline or aniline derivative and nitrobenzene into reactive contact; and b. reacting the aniline and nitrobenzene in a confined zone at a suitable time and temperature, in the presence of a mixture comprising a strong organic base, or equivalent thereof, and an oxidant comprising hydrogen peroxide in an amount of from about 0.01 to about 0.60 moles of hydrogen peroxide to moles of nitrobenzene.
    Type: Grant
    Filed: December 15, 2006
    Date of Patent: March 17, 2009
    Assignee: Flexsys America LLP
    Inventors: Ralph D. Triplett, Roger Keranen Rains
  • Patent number: 7488850
    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: Grant
    Filed: November 6, 2007
    Date of Patent: February 10, 2009
    Assignee: Bayer MaterialScience LLC
    Inventors: Knut Sommer, Markus Dugal, Ido Schwarz, Stefan Wershofen, Peter Lehner, Stephan Schubert, Alexandra Groβe Böwing
  • Publication number: 20080234518
    Abstract: Aromatic amines are produced by adiabatic hydrogenation of nitroaromatic compounds in the gas phase on one or more fixed catalysts. The nitroaromatic reactant is passed over the catalyst under pressure and at elevated temperature with hydrogen, water, optionally nitrogen and substantially in the absence of the aromatic amine produced from the nitroaromatic.
    Type: Application
    Filed: July 25, 2007
    Publication date: September 25, 2008
    Inventors: Knut Sommer, Ido Schwarz, Susanne Buchholz, Franz-Ulrich Von Gehlen, Andre Lago, Karl-Heinz Wilke, Holger Orzesek, Hans-Georg Pirkl, Peter Lehner, Stephan Schubert
  • Patent number: 7235694
    Abstract: A process for preparing 4-aminodiphenylamine having the steps of reacting nitrobenzene and aniline in the presence of a complex base catalyst, hydrogenating the reaction mixture with hydrogen, a powdery composite catalyst, and a hydrogenation solvent; separating, recovering, and reusing the complex base catalyst and the powdery composite catalyst from the reaction mixture; separating, recovering, and reusing aniline, and optionally water, from the the reaction mixture; refining the reaction mixture to obtain 4-aminodiphenylamine. The complex base catalyst comprises tetraalkyl ammonium hydroxide, and tetraalkyl ammonium salt.
    Type: Grant
    Filed: June 30, 2006
    Date of Patent: June 26, 2007
    Assignee: Sinorgchem Co., Shandong
    Inventors: Xiaogen Feng, Nongyue Wang, Xiaohui Mao, Ruibiao Yu, Qianwen Cheng
  • Patent number: 7193112
    Abstract: The invention describes a process for the production of aromatic amines by the catalytic hydrogenation of aromatic nitro compounds, with the process being characterized by at least one catalytic hydrogenation step and the catalyst consists at least of a monolithic support and a catalytically active coating.
    Type: Grant
    Filed: October 7, 2004
    Date of Patent: March 20, 2007
    Assignee: Bayer MaterialScience AG
    Inventors: Peter Lehner, Thomas Turek, Matthias Brandt, Susanne Buchholz
  • Patent number: 7183439
    Abstract: The invention is directed to a method of producing one or more 4-aminodiphenylamine intermediates comprising the steps: a. bringing an aniline or aniline derivative and nitrobenzene into reactive contact; and b. reacting the aniline and nitrobenzene in a confined zone at a suitable time and temperature, in the presence of a mixture comprising a strong organic base, or equivalent thereof, and an oxidant comprising hydrogen peroxide in an amount of from about 0.01 to about 0.60 moles of hydrogen peroxide to moles of nitrobenzene.
    Type: Grant
    Filed: May 23, 2003
    Date of Patent: February 27, 2007
    Assignee: Flexsys America L.P.
    Inventors: Ralph Dale Triplett, II, Roger Keranen Rains
  • Patent number: 7176333
    Abstract: The present invention discloses a process for preparing 4-aminodiphenylamine, which process uses nitrobenzene and aniline as raw materials, a complex base catalyst as condensation catalyst and a powdery composite catalyst as hydrogenation catalyst, and comprises five process stages: condensation; separation I; hydrogenation; separation II; and refining. The process can be continuously carried out. By selecting a complex base catalyst to catalyze the condensation reaction and separating it prior to the hydrogenation, the problem that the complex base catalysts thermally decompose in the hydrogenation reaction is avoided, the selectable range of hydrogenation catalysts is largely enlarged so that it is possible to select cheaper hydrogenation catalyst, and the selection of production process and equipment is easier and further industrialization is easier. The complex base catalysts used in the present invention are inexpensive and have higher catalytic activity.
    Type: Grant
    Filed: July 2, 2004
    Date of Patent: February 13, 2007
    Assignee: Sinorgchem Company, Shandong
    Inventors: Nongyue Wang, Ruibiao Yu, Xiaohui Mao, Xiaogen Feng, Qianwen Cheng
  • Patent number: 7109378
    Abstract: The invention pertains to an improved apparatus comprised of a monolith catalytic reactor having an inlet and an outlet and a static mixer having an inlet and an outlet thereto with the outlet of said static mixer in communication with the inlet of said monolith catalytic reactor. The invention also pertains to an improvement in a process for effecting a reaction in the monolith catalytic reactor wherein a reactant gas and reactant liquid are introduced to the inlet to the monolith catalytic reactor, reacted and, then, the reaction product passed through the outlet of the monolith catalytic reactor.
    Type: Grant
    Filed: January 21, 2002
    Date of Patent: September 19, 2006
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Keith Allen Welp, Anthony Rocco Cartolano, David Joseph Parrillo, Richard Peter Boehme, Reinaldo Mario Machado, Sylvia Caram
  • Patent number: 7084302
    Abstract: A process for preparing 4-aminodiphenylamine using nitrobenzene and aniline as raw materials, a complex base catalyst as the condensation catalyst, and a powdery composite catalyst as the hydrogenation catalyst. The process has 5 process stages including condensation, hydrogenation, separation I, separation II, and refining.
    Type: Grant
    Filed: July 2, 2004
    Date of Patent: August 1, 2006
    Assignee: Sinorgchem Shandong Co., Ltd.
    Inventors: Xiaogen Feng, Nongyue Wang, Xiaohui Mao, Ruibiao Yu, Qianwen Cheng
  • Patent number: 7064237
    Abstract: Amines are prepared by hydrogenation of the corresponding nitroaromatics in a vertical reactor whose length is greater than its diameter and which has in its upper region a downward-directed jet nozzle via which the reaction mixture and, if desired, part of the starting materials are introduced, has an outlet at any point on the reactor via which the reaction mixture is conveyed in an external circuit by means of a transport device back to the jet nozzle and has a flow reversal in its lower region, wherein at least part of the hydrogen and/or nitroaromatic starting materials used is fed into the liquid phase of the reactor in such a way that they travel upward in the liquid phase.
    Type: Grant
    Filed: February 4, 2003
    Date of Patent: June 20, 2006
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Zehner, Joern Mueller
  • Patent number: 6965053
    Abstract: A process for the production of aromatic amines which comprises the reduction of an aromatic compound containing at least two nitro groups with hydrogen in the presence of a catalyst is disclosed. The reaction is carried out so as to maintain up to 10% by weight of reaction intermediates (aminonitrites) and the solution produced is treated to recover the aromatic amine with a purity of over 99% and a mixture consisting of aromatic amine and reaction intermediates is recycled to the reactor.
    Type: Grant
    Filed: June 29, 2001
    Date of Patent: November 15, 2005
    Assignee: Dow Global Technologies Inc.
    Inventors: Anna Forlin, Antonio Beccari
  • Patent number: 6894193
    Abstract: Liquid organic compounds are hydrogenated by a process in which the hydrogen present in the reactor contains proportions of at least one gas which is inert in the hydrogenation reaction.
    Type: Grant
    Filed: January 25, 2002
    Date of Patent: May 17, 2005
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Zehner, Oliver Bey, Gunter Georgi, Jörn Müller
  • Patent number: 6818720
    Abstract: Supported, hydrogenating catalyst in powder form containing, as a catalytically active component, a primary precious metal component, a secondary precious metal component and one or more non-precious metal components. It is used for the hydrogenation of nitroaromatics, in particular nitrobenzene and DNT.
    Type: Grant
    Filed: November 6, 2002
    Date of Patent: November 16, 2004
    Assignee: Degussa AG
    Inventors: Jürgen Krauter, Michael Gross, Uwe Packruhn, Markus Göttlinger
  • Patent number: 6815562
    Abstract: The present invention relates to a process for the preparation of nitrodiphenylamines by reaction of nitrohalogens with anilines, a base and a catalyst, and to a process for the preparation of aminodiphenylamine by hydrogenation of the nitrodiphenylamine intermediately prepared.
    Type: Grant
    Filed: January 2, 2004
    Date of Patent: November 9, 2004
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Kunz, Joachim Haider, Dirk Ganzer, Ulrich Scholz, Adolf Sicheneder
  • Patent number: 6583320
    Abstract: The invention is directed-to a method of producing one or more 4-aminodiphenylamine intermediates comprising the steps of bringing an aniline or aniline derivative and nitrobenzene into reactive contact and reacting the aniline and nitrobenzene in a confined zone at a suitable time and temperature, in the presence of a mixture comprising an inorganic salt or metal organic salt having a cation that would be a suitable cation of a strong inorganic base, an oxidant and an organic base, the mixture not including a reaction product of betaine and a strong inorganic base.
    Type: Grant
    Filed: May 10, 2002
    Date of Patent: June 24, 2003
    Assignee: Flexsys America L.P.
    Inventors: Ralph Dale Triplett, II, Roger Keranen Rains
  • Patent number: 6495723
    Abstract: This invention provides a composition suitable for use in a reaction zone where aniline is reacted with nitrobenzene to obtain intermediates of 4-aminodiphenylamine comprising a solid support having interior channels with base material employed in the reaction loaded into the channels. The cross-sectional dimensions of the channels are such as to provide a restricted transition state with regard to the reaction and to improve the selectivity of the reaction in favor of the intermediates. The invention also provides a method for loading the base material in the solid support. The invention further provides a process for carrying out the above reaction using the above composition.
    Type: Grant
    Filed: June 21, 2000
    Date of Patent: December 17, 2002
    Assignee: Flexsys America
    Inventors: Antonio L. DeVera, Roger Keranan Rains
  • Patent number: 6395933
    Abstract: The invention is directed to a method of producing one or more 4-aminodiphenylamine intermediates comprising the steps of bringing an aniline or aniline derivative and nitrobenzene into reactive contact; and reacting the aniline and nitrobenzene in a confined zone at a suitable time and temperature, in the presence of a mixture comprising a strong base and a suitable phase transfer catalyst. Certain phase transfer catalysts may also function as the strong base.
    Type: Grant
    Filed: July 23, 2001
    Date of Patent: May 28, 2002
    Assignee: Flexsys America, L.P.
    Inventors: Ralph Dale Triplett, II, Roger Keranen Rains
  • Publication number: 20020006862
    Abstract: A novel precious metal doped porous metal catalyst is disclosed. The precious metal is present in from 0.01 to 1.5 weight percent and distributed throughout the particles of porous metal to provide a surface to bulk ratio distribution of not greater than 60. The present invention is further directed to a process of forming said doped catalyst and to improved processes of catalytic hydrogenation of organic compounds.
    Type: Application
    Filed: July 6, 2001
    Publication date: January 17, 2002
    Inventor: Stephen Raymond Schmidt
  • Patent number: 6268536
    Abstract: A process for the conversion of a picrate salt, preferably ammonium pricrate, to picric acid by acidifying the picrate salt in a two phase liquid system. One phase is an aqueous phase which contains an acid which is effective for acidifying ammonium picrate to picric acid and the other phase is an organic solvent phase in which the picric acid is soluble.
    Type: Grant
    Filed: December 6, 1999
    Date of Patent: July 31, 2001
    Inventors: Duane A. Goetsch, Kym B. Arcuri
  • Patent number: 6204413
    Abstract: The invention relates to a process for the preparation of specific salts of 1-substituted 2,4-diaminobenzenes by catalytic hydrogenation of 1-substituted 2,4-dinitrobenzenes and addition of the reaction product obtained after the hydrogenation and separated from the catalyst to an aqueous solution of an acid.
    Type: Grant
    Filed: April 11, 2000
    Date of Patent: March 20, 2001
    Assignee: Bayer Aktiengesellschaft
    Inventors: Lars Rodefeld, Alexander Klausener, Horst Behre
  • Patent number: 6140539
    Abstract: In a process for preparing amines, in which at least one compound containing at least one nitro group is reacted with hydrogen in the presence of a supported catalyst comprising, as catalytically active metal, nickel, if desired together with at least one metal of transition group I, V, VI and/or VIII, the reduced and stabilized supported catalyst comprises nickel crystallites having a bimodal nickel crystallite size distribution having maxima at 30-80 Angstrom and 81-150 Angstrom on a support comprising ZrO.sub.2, ZrO.sub.2 --HfO.sub.2 and/or SiO.sub.2 --ZrO.sub.2 and/or SiO.sub.2 --ZrO.sub.2 --HfO.sub.2 and in the reduced and passivated state has a nickel content of 60-80 percent by mass, an SiO.sub.2 content of 0-20 percent by mass, a ZrO.sub.2 content of 0-40 percent by mass, an HfO.sub.2 content of 0-4 percent by mass and after further reduction for one hour at 100.degree. C. has a degree of reduction of at least 70%.
    Type: Grant
    Filed: March 3, 2000
    Date of Patent: October 31, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Sander, Dietmar Peisker, Klaus Werner, Holger Braunsberg, Gunter Georgi, Ulrich Penzel
  • Patent number: 6096924
    Abstract: One object of the invention is a process for the catalytic hydrogenation of aromatic nitro compounds in solution or in melt in the presence of hydrogen and at least one noble metal catalyst, nickel catalyst or cobalt catalyst, in which process a catalytic amount of at least one vanadium compound is present, wherein the vanadium has the oxidation state 0, II, IV or V. It has been found that in the catalytic hydrogenation of aromatic nitro compounds the accumulation of hydroxylamines can be almost completely prevented by the addition of catalytic amounts of vanadium compounds, which usually results in concentrations of <1% hydroxylamine. The resulting hydrogenated products are whiter (purer) than those obtained without the addition of the vanadium compound because almost no azo or azoxy compounds are obtained. The hydrogenation, in particular the final phase, proceeds faster than without said addition. Accordingly, substantial advantages with respect to quality constancy and economy are obtained.
    Type: Grant
    Filed: November 13, 1997
    Date of Patent: August 1, 2000
    Assignee: Novartis AG
    Inventors: Martin Studer, Peter Baumeister
  • Patent number: 6080890
    Abstract: Aromatic amines are produced by catalytic hydrogenation of corresponding aromatic nitro compounds in the gas phase, by carrying out the hydrogenation in the presence of catalysts which, besides palladium, vanadium and lead, contain in addition molybdenum, tungsten and/or rhenium on a ceramic support having a BET surface area of less than 40 m.sup.3 /g, at temperatures of from 180.degree. C. to 500.degree. C. in a catalyst bed and in a molar ratio of hydrogen to the nitro group or nitro groups of 3:1 to 30:1.
    Type: Grant
    Filed: October 7, 1999
    Date of Patent: June 27, 2000
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reinhard Langer, Hans-Josef Buysch, Manfred Gallus, Joerg-Dietrich Jentsch
  • Patent number: 6034276
    Abstract: Disclosed is an improved process for preparing 1-chloro-2,4-diaminobenzene by the selective hydrogenation of 1-chloro-2,4-dinitro-benzene wherein the hydrogenation is carried out in the presence of a modified Raney nickel catalyst containing about 70 to 95 weight percent nickel, about 4 to 10 weight percent aluminum, about 0.1 to 4 weight percent molybdenum, and from 0 to about 20 weight percent cobalt. The 1-chloro-2,4-diaminobenzene is useful as an intermediate for disperse dyes and for color photography.
    Type: Grant
    Filed: March 22, 1999
    Date of Patent: March 7, 2000
    Assignee: Eastman Chemical Company
    Inventors: Robert Joseph Maleski, Edward Tipton Mullins
  • Patent number: 5990354
    Abstract: Ammonium picrate, Explosive "D", is converted to picric acid, which is then converted to triaminophenol by the conversion of the aromatic nitro groups to amino groups. The triaminophenols are then converted to triaminobenzenes by the removal of the hydroxyl groups and the triaminobenzenes are converted to m-phenylenediamine, aniline, and primary aliphatic amines by the removal of amino groups.
    Type: Grant
    Filed: November 17, 1998
    Date of Patent: November 23, 1999
    Assignee: Gradient Technology
    Inventors: Duane A. Goetsch, Kym B. Arcuri
  • Patent number: 5977411
    Abstract: This invention provides a method for preparing 4-ADPA by charging nitrobenzene into a reaction zone under hydrogen pressure in the presence of a strong organic base and a catalyst for hydrogenation. The method provides the convenience and economy of a one-step process, while producing improved yields and selectivities. The invention further provides for various embodiments of the foregoing which are suitable for the production of 4-ADPA, and the hydrogenation or reductive alkylation to produce PPD. Important to the invention are the molar ratios of aniline to nitrobenzene and nitrobenzene to the strong organic base and the choice and use of hydrogenation catalyst.
    Type: Grant
    Filed: June 10, 1997
    Date of Patent: November 2, 1999
    Assignee: Flexsys America L.P.
    Inventor: Antonio L. DeVera
  • Patent number: 5877350
    Abstract: Aromatic amines are produced by hydrogenation of the appropriate aromatic nitro compounds in the vapour phase on fixed catalysts. The catalysts contain supported metals active in hydrogenation, the reaction is carried out under adiabatic conditions at a pressure of from 1 to 30 bar, an inlet temperature of from 200.degree. to 400.degree. C. and a maximum catalyst temperature of 500.degree. C.
    Type: Grant
    Filed: August 4, 1995
    Date of Patent: March 2, 1999
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reinhard Langer, Hans-Josef Buysch, Ursula Pentling, Paul Wagner
  • Patent number: 5728880
    Abstract: Amine mixtures generated during the production of diaminotoluene by hydrogenating dinitrated aromatic compounds are treated to separate high boiling materials from the desired amine products. In this process, any water of reaction and any solvent are first removed from the diaminotoluene isomer mixture (TDA mixture). The low-boiling TDA isomers are then separated using a TDA isomer distillation column. In the process of the present invention, the bottom phase remaining after the initial distillation contains a mixture of m-TDA and high-boiling materials. This bottom phase is separated and concentrated until the high-boiling material content is from approximately 25 to 60 wt. %. This concentrated bottom phase is then mixed with o-TDA in a ratio of 1:1 to 1:5 and a m-/o-TDA mixture is removed by distillation. The m-/o-TDA mixture thus recovered is then returned to the TDA isomer distillation column.
    Type: Grant
    Filed: February 25, 1997
    Date of Patent: March 17, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heiko Beckhaus, Harro Witt, Uwe-Jens Zarnack, Gerd Greger
  • Patent number: 5712414
    Abstract: The present invention relates to a process for the preparation of hydroxycarboxylic acid amides of the general formula (1): ##STR1## in which R.sup.1 and R.sup.2 are identical or different and are hydrogen, halogen, cyano, a linear or branched alkyl, alkenyl, alkynyl or alkoxy group having 1 to 12 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, a cycloalkyl group having 6 to 12 carbon atoms or an aryl group having 6 to 12 carbon atoms, R.sup.3 is hydrogen or a linear or branched alkyl group having 1 to 4 carbon atoms, R.sup.4 is hydrogen or a linear or branched alkyl group having 1 to 6 carbon atoms, or R.sup.3 and R.sup.4, together with the carbon atom to which they are attached, form a five- or six-membered cycloalkane ring, and n is an integer from 1 to 12, wherein an aniline of the general formula (2) ##STR2## in which R.sup.1, R.sup.2, R.sup.3 and R.sup.
    Type: Grant
    Filed: July 10, 1996
    Date of Patent: January 27, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Andreas Dierdorf, Theodor Papenfuhs
  • Patent number: 5693862
    Abstract: The present invention is directed to a process for transporting toluenediamine (TDA) from a first site to a second site. The process of the invention comprises the steps of (a) providing a molten mass of TDA isomers at the first site; (b) cooling the molten mass to a temperature below the melting point, the molten mass thereby forming flowable particles of solid TDA in an inert gas; (c) providing an airtight storage vessel lined with a chemically inert liner; (d) storing the flowable particles of solid TDA in the lined storage vessel; (e) charging the storage vessel with inert gas; (f) transporting the storage vessel from the first site to the second site; and (g) remelting the TDA flowable particles in inert gas with TDA liquid that is superheated above the melting point to produce a molten TDA isomer mixture in inert gas having substantially the same isomer ratio as that of the molten mass.
    Type: Grant
    Filed: December 18, 1996
    Date of Patent: December 2, 1997
    Assignee: Arco Chemical Technology, L.P.
    Inventors: Majid Keyvani, Rekha Menon, James L. Meyer, Thomas W. Offill
  • Patent number: 5646085
    Abstract: The present invention relates to a process and a catalyst for hydrogenation of aromatic nitro or nitroso (nitrosated) compounds. The process, useful in hydrogenation, especially in the liquid phase, of compounds, nitroaromatic ones in particular, is defined in that the said compound is hydrogenated in the presence of tungsten carbide, the partial pressure of hydrogen being at least equal to two atmospheres (2.times.10.sup.5 pascals). The process also has application to organic synthesis.
    Type: Grant
    Filed: July 8, 1994
    Date of Patent: July 8, 1997
    Assignee: Rhone-Poulenc Chimie
    Inventors: Roland Jacquot, Claude Mercier
  • Patent number: 5633407
    Abstract: A process for preparing substituted aromatic azo compounds is provided which comprises contacting a nucleophilic compound and an azo containing compound in the presence of a suitable solvent system, and reacting the nucleophilic compound and the azo containing compound in the presence of a suitable base and a controlled amount of protic material at a temperature of about 10.degree. C. to about 150.degree. C. in a confined reaction zone wherein the molar ratio of protic material to base is 0:1 to about 5:1. In another embodiment, the substituted aromatic azo compounds are further reacted with a nucleophilic compound in the presence of a suitable solvent system, a suitable base and a controlled amount of protic material at a temperature of about 70.degree. C. to about 200.degree. C. in a confined reaction zone wherein the molar ratio of protic material to base is 0:1 to about 5:1 to produce a substituted aromatic amine.
    Type: Grant
    Filed: May 18, 1995
    Date of Patent: May 27, 1997
    Assignee: Flexsys America L. P.
    Inventors: Michael K. Stern, Brian K-M Cheng
  • Patent number: 5618979
    Abstract: A process for preparing substituted aromatic amines which comprises contacting a nucleophilic compound and a substituted aromatic azo compound in the presence of a suitable solvent system, and reacting the nucleophilic compound and the substituted aromatic azo compound in the presence of a suitable base and a controlled amount of protic material at a temperature of about 70.degree. C. to about 200.degree. C. in a confined reaction zone wherein the molar ratio of protic material to base is 0:1 to about 5:1. In another embodiment, the substituted aromatic amines of the invention are reductively alkylated to produce alkylated diamines or substituted derivatives thereof.
    Type: Grant
    Filed: May 18, 1995
    Date of Patent: April 8, 1997
    Assignee: Flexsys America L. P.
    Inventors: Michael K. Stern, Brian K-M Cheng