Preparing Compound Which Contains Halogen Bonded Directly To Carbon Patents (Class 564/417)
  • Patent number: 11512006
    Abstract: A method for simultaneously preparing an iron oxide red pigment and an aromatic amine is provided. In the method, an aromatic nitro compound and ferrous iron are first used to prepare an iron oxide red seed crystal under the action of a catalyst, and then iron powder is used to reduce the aromatic nitro compound and generate iron oxide in situ which grows into iron oxide red with pigment performance on the seed crystal. The method provides a clean and economical way for the reduction of an aromatic nitro compound (especially those in which there are other easily-reduced substituents on an aromatic ring) to prepare an aromatic amine.
    Type: Grant
    Filed: November 20, 2020
    Date of Patent: November 29, 2022
    Assignee: HEBEI CAIKE CHEMICAL CO., LTD.
    Inventors: Weidong Duan, Guofu Zhang, Yu Wei
  • Patent number: 11309538
    Abstract: A method for fabricating porous wire-in-tube (WiT) nanostructures including forming a first porous core-shell nanostructure, forming a second porous core-shell nanostructure by increasing thickness and porosity of the porous core-shell nanostructure, and forming a porous WiT nanostructure by etching the second porous core-shell nanostructure. Forming the first porous core-shell nanostructure may include forming a porous layer on a semi-conductive core by depositing a first plurality of particles on the semi-conductive core and generating an initial porous semi-conductive core by etching the semi-conductive core simultaneously with forming the porous layer.
    Type: Grant
    Filed: October 5, 2019
    Date of Patent: April 19, 2022
    Assignee: UNIVERSITY OF TEHRAN
    Inventors: Mehrnoosh Sadeghipari, Mohammadreza Hajmirzaheydarali, Shamsoddin Mohajerzadeh, Alireza Mashayekhi, Mohammad Ala Mohajerzadeh, Ali Akhavan Farahani
  • Patent number: 9346826
    Abstract: A process for producing an intermediate for a cyclic carbodiimide compound includes a process for producing an amine compound represented by the following formula (B), comprising the step of reducing a nitro compound represented by the following formula (A) and containing a compound having a haloarene skeleton in the presence of a metal catalyst and a basic compound. The process also includes a process for producing a thiourea compound, including the step of reacting an amine compound represented by the formula (B) with carbon disulfide in the presence of imidazole. (R is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.) (R is as defined in the above formula (A).).
    Type: Grant
    Filed: June 15, 2011
    Date of Patent: May 24, 2016
    Assignee: TEIJIN LIMITED
    Inventor: Shinichiro Shoji
  • Patent number: 9266094
    Abstract: The present invention relates to a catalyst comprising a ceramic support with a BET surface area of less than 40 m2/g and (a) 1.0 to 100 g of at least one metal of groups 8 to 12 of the periodic table of the elements, (b) 1.0 g to 100 g of at least one metal of groups 4 to 6 and 12 of the periodic table of the elements and (c) 1.0 g to 100 g of at least one metal of groups 14 and 15 of the periodic table of the elements per liter of bulk volume of the ceramic support, wherein the catalyst is additionally doped with (d) potassium in a content of from 0.0050% by weight to 0.20% by weight, based on the total weight of the catalyst. The present invention also provides the use of such a catalyst in the catalytic gas phase hydrogenation of nitroaromatics.
    Type: Grant
    Filed: August 29, 2012
    Date of Patent: February 23, 2016
    Assignee: Bayer Intellectual Property GmbH
    Inventors: Michael Merkel, Karl-Heinz Wilke, Peter Lehner
  • Publication number: 20150080609
    Abstract: Pt0-nanoparticles in the size range of 0 to 10 nm were prepared in-situ by impregnation of H2PtCl66H2O into the nanopores of modified montmorillonite followed by reduction with different reducing agents like ethylene glycol, sodium citrate, hydrogen, hydrazine and sodium borohydrate. The montmorillonite was modified by activation with mineral acids under controlled condition for generating desired nanopores. XRD pattern of Pt0-nanoparticles revealed the formation of face centered cubic (fcc) lattice. These supported Pt0-nanoparticles show efficient catalytic activity for the selective reduction of chloronitrobenzenes. As a typical example, at a H2 pressure of 10 bars, temperature 45° C. for a period of 15 min, the Pt0-nanoparticles (prepared by reduction with hydrazine) exhibit conversion of o-chloronitrobenzene up to 100% and selectivity >99% to o-chloroanilines with very negligible amount of C—Cl bond cleavage.
    Type: Application
    Filed: November 21, 2014
    Publication date: March 19, 2015
    Inventors: Dipak Kumar Dutta, Dipanka Dutta
  • Publication number: 20150045481
    Abstract: The present invention relates to a novel diamine compound, wherein two substituents R and R? are introduced asymmetrically, and a polymer thereof. The polymer may have excellent solubility in the organic solvent and allows for easy processibility after imidization, thus giving proper film maintaining superior properties, such as thermal, mechanical, and optical properties for applications in electrical, electronic, or optical materials.
    Type: Application
    Filed: December 5, 2012
    Publication date: February 12, 2015
    Inventors: Sang Youl Kim, Sun Dal Kim, Im Sik Chung
  • Publication number: 20140066658
    Abstract: A method is described for the catalytic hydrogenation of aromatic nitro compounds with hydrogen to the corresponding amines in the presence of a supported catalyst comprising platinum. The method is characterized in that the catalyst comprising platinum has been modified with a tungsten compound and with a phosphorus compound in an oxidation state of <5. High yields and high selectivities are possible with the method.
    Type: Application
    Filed: September 3, 2013
    Publication date: March 6, 2014
    Inventors: Doris Neumann, Joachim Ritzer
  • Patent number: 8563753
    Abstract: The present invention relates to a catalyst system. In particular the invention relates to a catalyst in the form of metal or an alloy that is encapsulated within a polymer shell or matrix. More specifically the invention is directed towards reactive catalytic metals that may be pyrophoric or otherwise reactive in air and/or susceptible to oxidation. In particular, the invention is concerned with catalysts based on nickel.
    Type: Grant
    Filed: February 12, 2010
    Date of Patent: October 22, 2013
    Inventors: Thomas Eric Oliver Screen, Mohammed Nisar
  • Publication number: 20130190500
    Abstract: This invention relates to a process for the preparation of 6-chloro-3-amino-2-(2-hydroxypropyl)-1-azanapthalene. It comprises treating 6-chloro-3-pyridylium-2-ethoxycarbonyl-1-azanaphthanlene bromide with morpholine at about 80° C., followed by treating the product thereof with methylmagnesium chloride.
    Type: Application
    Filed: December 10, 2012
    Publication date: July 25, 2013
    Applicant: NEURON SYSTEMS, INC.
    Inventor: Neuron Systems, Inc.
  • Publication number: 20130072722
    Abstract: The present invention relates to supported metal catalysts, wherein the catalysts are modified by at least one amine, a method for the preparation thereof and hydrogenation processes utilising the supported metal catalysts.
    Type: Application
    Filed: February 17, 2011
    Publication date: March 21, 2013
    Applicant: JOHNSON MATTHEY PUBLIC LIMITED COMPANY
    Inventors: Peter Trenton Bishop, James Cookson, Frederick Earnest Hancock, Steven Hawker, Robert John McNair
  • Publication number: 20130035511
    Abstract: Process for hydrogenating organic compounds in the gas phase in the presence of a catalyst comprising a nanoparticulate palladium cluster and a gas- and liquid-permeable shell comprising zirconium oxide.
    Type: Application
    Filed: September 25, 2012
    Publication date: February 7, 2013
    Applicant: BAYER TECHNOLOGY SERVICES GMBH
    Inventor: BAYER TECHNOLOGY SERVICES GMBH
  • Publication number: 20120296124
    Abstract: Efficient and recyclable heterogeneous nanocatalysts and methods of synthesizing and using the same are provided.
    Type: Application
    Filed: February 14, 2012
    Publication date: November 22, 2012
    Inventors: Tewodros Asefa, Ankush V. Biradar, Yanfei Wang
  • Publication number: 20120296122
    Abstract: Disclosed are fluoroether-functionalized aminoaromatic compounds and derivatives thereof. The compounds disclosed have utility as functionalized monomers and co-monomers in polyamides, polyoxadiazoles. Incorporation of the monomers into polymers can provide improved soil resistance to articles produced from the polymers.
    Type: Application
    Filed: May 17, 2011
    Publication date: November 22, 2012
    Applicant: E. I. DU PONT DE NEMOURS AND COMPANY
    Inventors: Neville Everton Drysdale, Fredrik Nederberg
  • Publication number: 20120296123
    Abstract: Disclosed are functionalized fluoroether-functionalized nitroaromatic compounds and derivatives thereof. The compounds disclosed have utility as precursors of functionalized monomers and co-monomers in polyamides, polyoxadiazoles and the like. Incorporation of the monomers into polymers can provide improved soil resistance to articles produced from the polymers.
    Type: Application
    Filed: May 17, 2011
    Publication date: November 22, 2012
    Applicant: E.I. DU PONT DE NEMOURS AND COMPANY
    Inventors: Neville Everton Drysdale, Fredrik Nederberg
  • Publication number: 20120016139
    Abstract: The present invention relates to a catalyst system. In particular the invention relates to a catalyst in the form of metal or an alloy that is encapsulated within a polymer shell or matrix. More specifically the invention is directed towards reactive catalytic metals that may be pyrophoric or otherwise reactive in air and/or susceptible to oxidation. In particular, the invention is concerned with catalysts based on nickel. Raney or sponge nickel is highly hazardous: a self-igniting solid; produces hazardous fumes when burning; causes irritation of the respiratory tract, nasal cavities; causes pulmonary fibrosis if inhaled; ingestion may lead to convulsions and intestinal disorders; causes eye and skin irritation; and chronic exposure may lead to pneumonitis and sensitization (“nickel itch”). The invention provides metal catalysts that avoid such problems and have a good shelf life and working life.
    Type: Application
    Filed: February 12, 2010
    Publication date: January 19, 2012
    Applicant: REAXA LIMITED
    Inventors: Thomas Eric Oliver Screen, Mohammed Nisar
  • Publication number: 20120004404
    Abstract: The present invention relates to the field of [18F] radiofluorination chemistry for the preparation of Positron Emission Tomography (PET) radioligands and [18F] radiofluorinating reagents. The invention further provides kits for preparation of the same.
    Type: Application
    Filed: March 15, 2010
    Publication date: January 5, 2012
    Inventors: Edward George Robins, Erik Arstad
  • Publication number: 20110207958
    Abstract: The present invention relates to a novel a process for the preparation of 9-dichloromethylene-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-ylamine which process comprises a) reacting cyclopentadiene in the presence of a radical initiator and CXCI3, wherein X is chloro or bromo, to a compound of formula I1, or aa) reacting cyclopentadiene with CXCI3, wherein X is chloro, in the presence of a metal catalyst to a compound of formula I1, wherein X is chloro, b) reacting the compound of formula I1 with a base in the presence of an appropriate solvent to the compound of formula III, c) and converting the compound of formula III in the presence of 1,2-dehydro-6-nitrobenzene to the compound of formula IV, and d) hydrogenating the compound of formula IV in the presence of a metal catalyst.
    Type: Application
    Filed: September 28, 2009
    Publication date: August 25, 2011
    Applicant: SYNGENTA CROP PROTECTION LLC
    Inventors: Denis Gribkov, Bjorn Antelmann, Fanny Giordano, Harald Walter, Alain De Mesmaeker
  • Publication number: 20110144382
    Abstract: A catalyst comprising a plurality of support nanoparticles and a plurality of catalytic nanoparticles. At least one catalytic nanoparticle is bonded to each support nanoparticle. The catalytic particles have a size and a concentration, wherein a first configuration of the size and the concentration of the catalytic nanoparticles enables a first catalysis result and a second configuration of the size and the concentration of the catalytic nanoparticles enables a second catalysis result, with the first and second configurations having a different size or concentration, and the first and second catalysis results being different. In some embodiments, the first catalysis result is a selective reduction of a first selected functional group without reducing one or more other functional groups, and the second catalysis result is a selective reduction of a second selected functional group without reducing one or more other functional groups.
    Type: Application
    Filed: December 15, 2010
    Publication date: June 16, 2011
    Applicant: SDCMATERIALS, INC.
    Inventors: Qinghua Yin, Xiwang Qi
  • Patent number: 7795472
    Abstract: A process for the industrial production of 2-amino-2-[2-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]ethyl]-1,3-propanediol hydrochloride (Compound I), an effective immunosuppressant. The process for producing 2-amino-2-[2-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]ethyl]-1,3-propanediol hydrochloride or a hydrate thereof includes the steps of reacting 4-(3-benzyloxyphenylthio)-2-chlorobenzaldehyde with ethyl diethylphosphonoacetate in a solvent in the presence of a base to form ethyl 3-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]acrylate; reducing the resulting ethyl 3-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]acrylate, followed by mesylation, iodination and nitration, to form 1-benzyloxy-3-[3-chloro-4-(3-nitropropyl)phenylthio]benzene; forming 2-[2-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]ethyl]-2-nitro-1,3-propanediol using a formaldehyde solution; and reducing the resulting 2-[2-[4-(3-benzyloxyphenylthio)-2-chlorophenyl]ethyl]-2-nitro-1,3-propanediol to form the desired product.
    Type: Grant
    Filed: October 7, 2005
    Date of Patent: September 14, 2010
    Assignee: Kyorin Pharmaceutical Co., Ltd.
    Inventors: Takeshi Tsubuki, Kenichi Kobayashi, Hidetaka Komatsu
  • 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: 7381844
    Abstract: A hydrogenation process of chloronitrobenzene. The hydrogenation process comprises the steps of producing a nanosized boron-containing nickel catalyst, wherein a ratio of the amount of the boron atom to the amount of the nickel atom in the nanosized boron-containing nickel catalyst is of about 0.1-0.9. Then, the nanosized boron-containing nickel catalyst is placed into a reactor with a chloronitrobenzene an alcohol solvent having carbon number less than four per molecule and a hydrogenation process is performed to hydrogenating the chloronitrobenzene in hydrogen with a reaction pressure of about 5-40 atm and a reaction temperature of about 40-150° C.
    Type: Grant
    Filed: August 4, 2006
    Date of Patent: June 3, 2008
    Assignee: National Central University
    Inventors: Yu-Chang Liu, Chung-Yin Huang, Yu-Wen Chen
  • Patent number: 7282610
    Abstract: A method of producing an aromatic amine compound, that includes reducing an aromatic nitro compound that has an aromatic ring having an alkylthio group as a substituent, to obtain a corresponding aromatic amine compound, wherein the aromatic nitro compound is reduced using a hydrazine compound in the presence of an iron compound and an activated carbon.
    Type: Grant
    Filed: November 24, 2004
    Date of Patent: October 16, 2007
    Assignee: Fujifilm Corporation
    Inventors: Hiroshi Yasuoka, Hideto Mori
  • 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: 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: 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: 7015176
    Abstract: A process is described for the synthesis of an aryl sulfur pentafluoride compound. In one embodiment of the present invention, there is provided a process for preparing an aryl sulfurpentafluoride compound comprising: combining an at least one aryl sulfur compound with a fluorinating agent to at least partially react and form an intermediate aryl sulfurtrifluoride product; and exposing the intermediate aryl sulfurtrifluoride product to the fluorinating agent and optionally a fluoride source to at least partially react and form the aryl sulfurpentafluoride compound.
    Type: Grant
    Filed: June 3, 2003
    Date of Patent: March 21, 2006
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Wade H. Bailey, III, William J. Casteel, Jr., Reno J. Pesaresi, Frank M. Prozonic
  • 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: 6891067
    Abstract: The present invention provides an optical polyimide precursor for use in making a polyimide. The precursor is defined by the following formula: wherein X is Cl, Br, oxo-halide, or fully halogenated alkyl, and A is a divalent aromatic or halogenated aromatic moiety. The present invention provides a method of preparing a diamine compound for use as an optical polyimide precursor. The method includes the steps of dissolving 2-chloro-5-nitrobenzotrifluoride and a diol in N,N-dimethylacetamide to form a solution, adding potassium carbonate, tert-butylammonium chloride and copper powder to said solution and heating the resulting mixture, removing the copper, precipitating and recrystallizing a dinitro-compound resulting from heating the mixture, and dissolving the dinitro-compound and reducing the dinitro-compound to yield a diamine compound.
    Type: Grant
    Filed: October 8, 2002
    Date of Patent: May 10, 2005
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Kyung-Hee You, Kwan-Soo Han, Tae-Hyung Rhee, Eun-Ji Kim, Jung-Hee Kim, Woo-Hyeuk Jang
  • Patent number: 6657085
    Abstract: A process for the preparation of aniline compounds of formula: wherein n and R are as defined in claim 1, by reacting nitro compounds of formula: wherein n and R are as defined, with hydrazine at elevated temperature in the presence of an aqueous base. The compounds of formula I are suitable as intermediates in the preparation of herbicides of the isobenzofuranone type.
    Type: Grant
    Filed: November 15, 2002
    Date of Patent: December 2, 2003
    Assignee: Syngenta Crop Protection, Inc.
    Inventors: Gottfried Seifert, Thomas Rapold
  • Patent number: 6479704
    Abstract: The present invention relates to an improved for the hydrogenation of an immiscible mixture of an organic reactant in water. The immiscible mixture can result from the generation of water by the hydrogenation reaction itself or, by the addition of, water to the reactant prior to contact with the catalyst. The improvement resides in effecting the hydrogenation reaction in a monolith catalytic reactor from 100 to 800 cpi, at a superficial velocity of from 0.1 to 2 m/second in the absence of a cosolvent for the immiscible mixture. In a preferred embodiment, the hydrogenation is carried out using a monolith support which has a polymer network/carbon coating onto which a transition metal is deposited.
    Type: Grant
    Filed: April 20, 2001
    Date of Patent: November 12, 2002
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Andrew Francis Nordquist, Frederick Carl Wilhelm, Francis Joseph Waller, Reinaldo Mario Machado
  • Patent number: 6333434
    Abstract: The invention relates to a process for the preparation of trifluoromethylanilines of formula (I) wherein R1 is hydrogen, fluorine, chlorine, bromine, methyl, monochloromethyl, dichloromethyl, or formyl, and R2 is hydrogen, fluorine or chlorine, with the proviso that when R1 and R2 are both hydrogen, the amino group is para to the trifluoromethyl group, comprising (a) nitrating a benzotrichloride of formula (II)  wherein R1 and R2 are each as defined for formula (I), thereby forming a nitrobenzotrichloride, (b) converting the trichloromethyl group of the nitrobenzotrichloride into a trifluoromethyl group by reaction with anhydrous hydrofluoric acid, thereby forming a nitrobenzotrifluoride, and (c) reducing the nitro groups of the nitrobenzotrifluoride to form a trifluoromethylaniline of formula (I).
    Type: Grant
    Filed: November 6, 2000
    Date of Patent: December 25, 2001
    Assignee: Bayer Aktiengesellschaft
    Inventors: Albrecht Marhold, Käthe Baumann
  • Patent number: 6278022
    Abstract: Disclosed herein is an improvement in a method for making compounds having the structural formulae (I) or (II): wherein: X is a) phenyl; lower phenylalkoxy; phenoxy; or benzyl; or b) one substituent from group a) and one or more substituents selected from C1-C4 alkoxy; hydroxyl; halogen; lower alkyl; and lower alkylthio; or c) along with the phenyl to which it is attached, forms a multiple fused ring heterocycle such as dibenzofuranyl; Y is H, C1-C4 alkanoyl, C1-C4 haloalkenoyl, dialkoxyphosphoryl, alkylaminocarbonyl, haloalkylsulfonyl, or C1-C4 alkoxy carbonyl; and R is H, C1-C6 alkyl, C1-C6 alkoxy, C3-C6 cycloalkoxy, haloalkyl, alkoxyalkyl, arylalkoxy, alkenyl, alkylthio, alkoxycarbonyl, alkylamino, heteroaryl, arylalkyl, haloalkoxy, aryloxy, or C3-C6 cycloalkyl; and Z is O or S, wherein the improvement comprises the steps of: A) selecting as a starting material a compound of the structural formula B) dissolving compound III in an organic solvent selected from the group
    Type: Grant
    Filed: November 1, 1999
    Date of Patent: August 21, 2001
    Assignee: CK Witco Corporation
    Inventor: Haihong Jin
  • Patent number: 6268533
    Abstract: A method is disclosed for the preparation of optically pure isomers of formoterol by the reaction of an optically pure 4-benzyloxy-3-formamidostyrene oxide with an optically pure 4-methoxy-&agr;-methyl-N-(phenylmethyl)benzeneethanamine followed by debenzylation. Useful intermediates in the process are also disclosed, as are the novel L-tartrate salt of R,R-formoterol and pharmaceutical compositions thereof.
    Type: Grant
    Filed: January 27, 2000
    Date of Patent: July 31, 2001
    Assignee: Sepracor Inc.
    Inventors: Yun Gao, Robert Hett, Kevin Q. Fang, Stephen A. Wald, Chris Hugh Senanayake
  • Patent number: 6258982
    Abstract: The present invention relates to a hydrogenation process for the preparation of aromatic amino compounds containing directly on the aryl ring or in a side chain one or more entities that may also undergo hydrogenation, such as carbon multiple bonds, nitrile groups, imino groups or carbonyl groups. The preparation is carried out by catalytic hydrogenation of the corresponding aromatic nitro compounds in the presence of a phosphorus-modified noble metal catalyst. The invention relates also to the use of modified noble metal catalysts for the hydrogenation of aromatic nitro compounds containing carbon multiple bonds and/or substituted by nitrile, imino or carbonyl groups.
    Type: Grant
    Filed: March 10, 1999
    Date of Patent: July 10, 2001
    Assignee: Novartis AG
    Inventors: Peter Baumeister, Urs Siegrist, Martin Studer
  • Patent number: 6232501
    Abstract: This invention relates to a process for the cis-selective preparation of cyclic amines of the sertraline type by reductive alkylation of cyclic immines or of their precursors and for the catalytic hydrogenation in the presence of copper-containing catalysts.
    Type: Grant
    Filed: September 14, 2000
    Date of Patent: May 15, 2001
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Heinz Steiner, Markus Benz, Hans-Peter Jalett, Marc Thommen
  • 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: 6121492
    Abstract: This invention relates to a method for the preparation of a compound of formula I ##STR1## comprising the steps consisting in: a) optionally reacting a compound of general formula II: ##STR2## with a nitration reagent b) reducing the compound obtained in a)c) subjecting the compound obtained in b) to a dehydrochlorination in order to obtain the compound of formula I: andd) isolating the compound obtained in step c) from the reaction mixture.
    Type: Grant
    Filed: November 29, 1999
    Date of Patent: September 19, 2000
    Assignee: Rhodia Chimie
    Inventor: Michel Dury
  • 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: 6077974
    Abstract: Amino-halogenophenyl alkyl thioethers prepared in an advantageous manner by catalytic reduction of the corresponding nitro compound by the nitro compound being continuously hydrogenated with hydrogen in the presence of a supported noble-metal catalyst.
    Type: Grant
    Filed: July 21, 1999
    Date of Patent: June 20, 2000
    Assignee: Bayer Aktiengesellschaft
    Inventor: Wolfgang Kiel
  • Patent number: 6069278
    Abstract: This invention relates the novel diamines, the polyimide oligomers and the polyimides derived therefrom and to the method of preparing the diamines, oligomers and the polyimides. The thermoplastic polyimides derived from the aromatic diamines of this invention are characterized as having a high glass transition temperature, good mechanical properties and improved processability in the manufacture of adhesives, electronic and composite materials for use in the automotive and aerospace industry. The distinction of the novel aromatic diamines of this invention is the 2,2',6,6'-substituted biphenyl radicals which exhibit noncoplanar conformation that enhances the solubility of the diamine as well as the processability of the polyimides, while retaining a relatively high glass transition temperature and improved mechanical properties at useful temperature ranges.
    Type: Grant
    Filed: November 23, 1999
    Date of Patent: May 30, 2000
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventor: Chun-Hua K. Chuang
  • 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: 5962741
    Abstract: The present invention relates to a hydrogenation process for the production of aromatic halogen-amino compounds by means of catalytic hydrogenation on noble metal catalysts of corresponding aromatic halonitro compounds, characterised in that a rhodium, ruthenium, iridium, platinum or palladium catalyst which is modified with an inorganic or organic phosphorus compound with a degree of oxidation of less than V, is used, in the presence of a vanadium compound.
    Type: Grant
    Filed: November 14, 1997
    Date of Patent: October 5, 1999
    Assignee: Novartis AG
    Inventors: Peter Baumeister, Urs Siegrist, Martin Studer
  • Patent number: 5877340
    Abstract: The invention relates to processes for preparing substituted aromatic amino compounds which contain at least one unsaturated --CN bond or carbonyl group on the aromatic radical or in a side chain, by catalytic hydrogenation of appropriate substituted aromatic nitro compounds in the presence of a modified noble metal catalyst of platinum which is modified with a metal selected from lead, mercury, bismuth, germanium, cadmium, arsenic, antimony, silver and gold.
    Type: Grant
    Filed: October 1, 1997
    Date of Patent: March 2, 1999
    Assignee: Novartis Consumer Health S.A.
    Inventors: Peter Baumeister, Urs Siegrist
  • Patent number: 5872300
    Abstract: 2-Amino-6-chlorophenyl-alkylsulfanes are prepared in a particularly advantageous manner by hydrogenating 2-chloro-6-nitrophenyl-alkylsulfanes catalytically in the presence of a solvent without the addition of a further sulfur compound, and the novel compound 2-amino-6-chlorophenyl-isopropylsulfane is provided.
    Type: Grant
    Filed: November 14, 1996
    Date of Patent: February 16, 1999
    Assignee: Bayer Aktiengesellschaft
    Inventors: Ferdinand Hagedorn, Wolfgang Kiel, Helmut Fiege
  • Patent number: 5856577
    Abstract: The instant invention relates to a process for the preparation of fluoroanilines of formula (I) wherein a fluorinated nitrated benzene compound of formula (II) is subjected to a catalytic hydrogenation in a liquid medium containing a catalyst, under hydrogen pressure, carrying out a catalytic reduction reaction and, optionally, a hydrogenolysis reaction, wherein the compound of formula (II) is introduced gradually into the said medium so that the content of compound of formula (II) in the liquid remains less than or equal to 1000 ppm by mass, in order selectively to form the compound of formula (I).
    Type: Grant
    Filed: May 28, 1997
    Date of Patent: January 5, 1999
    Assignee: Rhone-Poulenc Chimie
    Inventors: Georges Cordier, Gilbert Guidot, Philippe Marion, Claude Mercier
  • Patent number: 5840983
    Abstract: 2-Trifluoromethoxy-aniline, which can be used as an intermediate for example for preparing pharmaceuticals and agrochemicals, is obtained in very good yields and high purity by nitrating in a first step 1,2-dichlorotrifluoromethoxy-benzene at temperatures between -20.degree. C. and +80.degree. C. and catalytically hydrogenating the resulting nitration products (exclusively 1,2-dichloro-5-nitro-4-trifluoromethoxy-benzene and 1,2-dichloro-3-nitro-4-trifluoromethoxy-benzene) in a 2nd step, it being possible to isolate the aniline intermediates corresponding to the two nitrobenzene derivatives; the nitrobenzene and aniline derivatives mentioned, being novel compounds, are also part of the subject matter of the invention.
    Type: Grant
    Filed: July 18, 1997
    Date of Patent: November 24, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reinhard Lantzsch, Albrecht Marhold
  • Patent number: 5801284
    Abstract: Process for preparing haloaromatic amines by catalytic hydrogenation of the corresponding halonitroaromatic compounds, characterized in that iron-containing Raney nickel is used as catalyst, where the haloaromatic amines prepared can be used for the synthesis of photographic couplers which are useful in photographic emulsions or elements.
    Type: Grant
    Filed: February 5, 1997
    Date of Patent: September 1, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Franz-Josef Mais, Klaus-Christian Paetz, Helmut Fiege, Heinz Ulrich Blank, Dieter Brueck, Wolf Mehl
  • Patent number: 5744643
    Abstract: The present invention relates to a process for preparing aromatic amines by reacting an aromatic nitro compound with carbon monoxide in a solvent mixture comprising water and a water-insoluble organic solvent by means of a catalyst comprising palladium and a water-soluble phosphine under a pressure of from 5 to 300 bar and at a temperature of from 50 to 200.degree. C., and separating the aqueous phase and the organic phase.
    Type: Grant
    Filed: February 21, 1996
    Date of Patent: April 28, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Matthias Beller, Ahmed Tafesh, Christian Kohlpaintner, Christoph Naumann
  • Patent number: 5629449
    Abstract: Disclosed is a method of making 3,5-diaminobenzotrifluoride from 4-chloro-3,5-dinitrobenzotrifluoride. A solution of 4-chloro-3,5-dinitrobenzotrifluoride in an alcohol is prepared. Separately, a slurry is prepared of a palladium catalyst on a suitable substrate, at least one equivalent of magnesium oxide per equivalent of 4-chloro-3,5-dinitrobenzotrifluoride, sufficient hydrogen-donating reducing agent to reduce the 4-chloro-3,5-dinitrobenzotrifluoride to 3,5-diaminobenzotrifluoride, and an amount of alcohol sufficient to make the slurry stirrable. The solution is added to the slurry with stirring at a rate that does not exceed the reaction rate of the 4-chloro-3,5-dinitrobenzotrifluoride so that no unreacted 4-chloro-3,5-dinitrobenzotrifluoride accumulates in the slurry. The reaction mixture is heated at about 75.degree. to about 100.degree. C.
    Type: Grant
    Filed: August 17, 1992
    Date of Patent: May 13, 1997
    Assignee: Occidental Chemical Corporation
    Inventor: David E. Albright, Jr.
  • Patent number: 5545754
    Abstract: p-Amino-phenols are advantageously prepared by catalytic hydrogenation of the aromatic nitro compounds on which they are based in a reaction medium of aqueous sulphuric acid in the sense of a Bamberger rearrangement at elevated temperature by a procedure in which the reaction medium additionally contains a water-miscible organic solvent.
    Type: Grant
    Filed: November 26, 1991
    Date of Patent: August 13, 1996
    Assignee: Bayer Aktiengesellschaft
    Inventors: Alexander Klausener, Heinz Landscheidt, Heinz-Ulrich Blank