Of Nitro Or Nitroso Patents (Class 564/416)
  • Patent number: 11339115
    Abstract: The present invention relates to a process for continuous hydrogenation of a nitro compound to the corresponding amine in a liquid reaction mixture comprising the nitro compound in a reaction chamber in the presence of a supported catalyst which comprises as the active component at least one element from groups 7 to 12 of the periodic table of the elements, wherein ammonia is added to the reaction chamber during the hydrogenation.
    Type: Grant
    Filed: October 8, 2018
    Date of Patent: May 24, 2022
    Assignee: BASF SE
    Inventors: Barbara Wucher, Thomas Heidemann, Michael Friko, Christian Bechtold
  • Patent number: 9102585
    Abstract: An efficient continuous manufacturing process for 4-aminodiphenylamine by coupling aniline with nitrobenzene in the presence of tetramethylammonium hydroxide (TMAH) as a base, using flow reactors wherein base decomposition is considerably reduced by optimizing base quantity, process conditions and process equipment.
    Type: Grant
    Filed: April 13, 2012
    Date of Patent: August 11, 2015
    Assignee: NOCIL LIMITED
    Inventors: Chinmoy Nandi, Narendra Gangal, Pramod Purohit, Vinay Ketkar, Prahlad Rao
  • Publication number: 20150111976
    Abstract: The present disclosure provides a series of new and improved porous polyamide aerogels derived from multifunctional aromatics that combine the high mechanical strength of aramids with the pore structure of aerogels. The polyamide aerogels have a hyperbranched structure, relatively low density, high porosity and may be derived from functionalized monomers having more aromatic groups than functional groups. The present disclosure also provides a new method for producing the porous polyamide aerogels by polymerizing an aromatic multifunctional carboxylic acid or a ferrocene multifunctional carboxylic acid with a polyfunctional aromatic isocyanate at moderate reaction conditions followed by drying with liquid CO2. Also disclosed are various methods of use of these polyamide aerogels in a variety of applications.
    Type: Application
    Filed: October 31, 2014
    Publication date: April 23, 2015
    Inventors: Nicholas Leventis, Chariklia Sotiriou-Leventis, Malik Adnan Saeed
  • Publication number: 20140303402
    Abstract: Process for the preparation of known sulfonamides having antibacterial activity applicable on industrial scale, which allows their production in high yields and purity, comprising in particular the step of nucleophile aromatic substitution and oxidation in suitable conditions.
    Type: Application
    Filed: April 2, 2014
    Publication date: October 9, 2014
    Applicant: DIPHARMA FRANCIS S.r.l.
    Inventors: Pietro ALLEGRINI, Simone MANTEGAZZA
  • Patent number: 8853455
    Abstract: The present invention relates to a process for preparing substituted 2-nitrobiphenyls and to specific 2-nitrobiphenyls. The invention further relates to a process for preparing 2-aminobiphenyls from such 2-nitrobiphenyls and to a process for preparing (het)arylamides of such 2-aminobiphenyls.
    Type: Grant
    Filed: March 8, 2010
    Date of Patent: October 7, 2014
    Assignee: BASF SE
    Inventors: Alexander Korte, Jan Klaas Lohmann, Thomas Grote, Klaus Ebel, Thomas Zierke, Horst Mayer, Ralf Wazulek
  • Patent number: 8614355
    Abstract: The invention relates to a catalyst and to a process for hydrogenating organic compounds. In particular, the invention is directed to a process and catalyst for hydrogenating organic compounds with hydrogen. The organic compounds are subjected to hydrogenation in the presence of a catalyst comprising nitrogen-doped carbon nanotubes as a catalytically active component, wherein the proportion of nitrogen in the nanotubes is in the range of from about 0.05 to 20 wt. %.
    Type: Grant
    Filed: June 3, 2009
    Date of Patent: December 24, 2013
    Assignee: Bayer Technology Services GmbH
    Inventors: Aurel Wolf, Volker Michele, Jens Aβmann, Leslaw Mleczko
  • Patent number: 8609899
    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: Grant
    Filed: May 17, 2011
    Date of Patent: December 17, 2013
    Assignee: BASF SE
    Inventors: Andreas Raichle, Joana Coelho Tsou, Samuel Neto, Ulrich Penzel, Steffen Oehlenschlaeger, Michael Zoellinger, Holgar Braunsberg, Stefanie Haase, Johannes Buettner
  • Publication number: 20130253083
    Abstract: The present invention relates to a polymer supported reagent comprising a novel crosslinked mesoporous polymer, enabling a simple and easy production of an azoxy compound or an azo compound from an aromatic nitro compound, and a method of selectively reducing an aromatic nitro compound by using the same. The polymer supported reagent comprises a certain acrylamide mesoporous crosslinked polymer.
    Type: Application
    Filed: March 16, 2012
    Publication date: September 26, 2013
    Applicants: IUCF-HYU (Industry-University Cooperation Foundation Hanyang University), LG Chem, Ltd.
    Inventors: Yang-Kyoo Han, Jin Cho, Sang-Mi Lee, Seung-Hoon Shin
  • Publication number: 20130237725
    Abstract: Asymmetrical 2,5-disubstituted-1,4-diaminobenzenes are provided, along with a process for forming both symmetrical and asymmetrical 2,5-disubstituted-1,4-diaminobenzenes.
    Type: Application
    Filed: March 9, 2012
    Publication date: September 12, 2013
    Inventors: Zhang-Lin Zhou, Si-Ty Lam, Lihua Zhao
  • Patent number: 8334410
    Abstract: A method for producing a 3-mercaptoaniline compound, which is a known intermediate for a 3-(1H-1,2,4-triazol-1-yl)phenylsulfide derivative, useful as a pesticide, and a method for producing a compound which can be used as a starting material in producing the 3-mercaptoaniline compound are disclosed. In one embodiment the nitro group and the chlorosulfonyl group of a 3-nitrobenzenesulfonyl chloride compound represented by general formula (1): are reduced in the presence of an acid catalyst to produce a compound of general formula (2): In the above general formulas (1) and (2), R represents an alkyl group or a cyclic alkyl group, and X represents a halogen atom.
    Type: Grant
    Filed: November 28, 2008
    Date of Patent: December 18, 2012
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventor: Kentaro Kawazoe
  • Publication number: 20120202994
    Abstract: The invention relates to a method for carrying out a chemical reaction for producing a target compound by heating in a reactor a reaction medium containing at least one first reactant, such that a chemical bond inside the first reactant or between the first and a second reactant is formed or modified. The reaction medium is brought into contact with a solid heating medium that can be warmed by electromagnetic induction and that is inside the reactor and is surrounded by the reaction medium. Said heating medium is heated by electromagnetic induction with the aid of an inductor and the target bond is formed from the first reactant or from the first and a second reactant and said target bond is separated from the heating medium.
    Type: Application
    Filed: April 16, 2012
    Publication date: August 9, 2012
    Inventors: Carsten Friese, Andreas Kirschning, Jürgen Wichelhaus, Sascha Volkan Ceylau
  • Publication number: 20120157713
    Abstract: Provided is a method for preparing 4,4?-dinitrodiphenylamine (4,4?-DNDPA) in high yield via the NASH reaction using a mixture of a bis-quaternary ammonium base and a base catalyst for the reaction of urea with nitrobenzene, and a method of preparing 4,4?-bis(alkylamino)diphenylamine (4,4?BAADA) in high yield and purity by hydrogenating the resulting 4,4?-DNDPA with a ketone in the presence of hydrogen and hydrogenation catalyst. The catalyst complex used in the present invention allows easy recovery, provides superior alkaline stability and is capable of reducing production cost.
    Type: Application
    Filed: June 17, 2011
    Publication date: June 21, 2012
    Applicant: KOREA KUMHO PETROCHEMICAL CO., LTD.
    Inventors: Jin-Eok Kim, Seoung-IL Kim, Han Jin Kwag, Sang hee Park
  • Patent number: 8188316
    Abstract: Processes are provided for preparing complexes of 2,3,5,6-tetraaminotoluene with an aromatic diacid where the aromatic diacid is insoluble in water under ambient conditions. An integrated process design starting with nitration of 2,6-dihalotoluene eliminates costly intermediate drying and recrystallization steps. Handling of solid materials with possible skin sensitizing properties and toxicity is avoided, thereby eliminating human and environmental exposure.
    Type: Grant
    Filed: December 10, 2009
    Date of Patent: May 29, 2012
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Rajiv Dhawan, Joachim C. Ritter
  • Patent number: 8188317
    Abstract: An integrated process is provided for preparing complexes of 2,3,5,6-tetraminotoluene with an aromatic diacid starting with nitration of 2,6-dihalotoluene. The process design eliminates costly intermediate drying and recrystallization steps. Handling of solid materials with possible skin sensitizing properties and toxicity is avoided, thereby eliminating human and environmental exposure.
    Type: Grant
    Filed: December 10, 2009
    Date of Patent: May 29, 2012
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Rajiv Dhawan, Joachim C. Ritter
  • Patent number: 8163961
    Abstract: Complexes of 2,3,5,6-tetraaminotoluene with an aromatic diacid are prepared by reaction with a divalent salt of the aromatic diacid while maintaining the pH of the reaction solution between 3 and 10. The resulting complexes are suitable for making high molecular weight polybenzimidazole polymers for high-performance fibers.
    Type: Grant
    Filed: February 22, 2010
    Date of Patent: April 24, 2012
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Rajiv Dhawan, Joachim C. Ritter
  • Patent number: 8163955
    Abstract: An improved process is provided for the preparation of 2,6-diamino-3,5-dinitrotoluene by amination of 2,6-dichloro-3,5-dinitrotoluene. The presence of water unexpectedly results in a highly pure product, free of glycol ether impurities. This product can be used to make highly pure 2,3,5,6-tetraaminotoluene, which in turn can be used to make high molecular weight polybenzimidazoles for high strength fibers.
    Type: Grant
    Filed: December 10, 2009
    Date of Patent: April 24, 2012
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Rajiv Dhawan, Joachim C. Ritter
  • Patent number: 8158830
    Abstract: An integrated process is provided for preparing 1,2,4,5-tetraminobenzene and salts thereof, starting in certain embodiments with nitration of 1,3-dihalobenzene. The process design eliminates costly intermediate drying and recrystallization steps. Handling of solid materials with possible skin sensitizing properties and toxicity is avoided, thereby eliminating human and environmental exposure.
    Type: Grant
    Filed: December 17, 2008
    Date of Patent: April 17, 2012
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Joachim C. Ritter, Ekaterini Korovessi, Rajiv Dhawan
  • Patent number: 8071812
    Abstract: A process is provided for the preparation of 1,3-diamino-4,6-dinitrobenzene by amination of 1,3-dihalo-4,6-dinitrobenzene. The presence of water advantageously results in a highly pure product, free or essentially free of glycol ether impurities.
    Type: Grant
    Filed: December 16, 2008
    Date of Patent: December 6, 2011
    Assignee: E.I du Pont de Nemours & Company
    Inventors: Joachim C. Ritter, Annalisa Hargis
  • Patent number: 8030522
    Abstract: The invention relates to a process for the production of toluene diisocyanate, in which the crude toluenediamine obtained from the hydrogenation is purified and then phosgenated. The purification step reduces the total amount of cyclic ketones to less than 0.1% by weight, based on 100% by weight of the toluenediamine.
    Type: Grant
    Filed: June 7, 2006
    Date of Patent: October 4, 2011
    Assignees: Bayer MaterialScience LLC, Bayer MaterialScience AG
    Inventors: Joachim Zechlin, Bernd Pennemann, Friedhelm Steffens, Wenbin Ji
  • Publication number: 20110130575
    Abstract: A clay comprising a 2:1 aluminosilicate clay having negative charge sites, the 2:1 aluminosilicate clay containing subnano-sized zero valent iron (ZVI) particles distributed on clay surfaces is provided. In one embodiment, at least some or all of the particles have a cross-section of five (5) angstroms or less. Methods of synthesizing and the novel clays and the clay-templated subnano-scale ZVI particles themselves are also described. Such novel products are useful in a variety of remediation applications, including for reduction and dechlorination reactions.
    Type: Application
    Filed: October 29, 2010
    Publication date: June 2, 2011
    Inventors: Hui Li, Cheng Gu, Stephen A. Boyd
  • 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: 7541497
    Abstract: A process for preparing xylylenediamine, comprising the steps of ammoxidizing xylene to phthalonitrile, by contacting the vaporous product of the ammoxidation stage directly with a liquid organic solvent (quench), and hydrogenating the phthalonitrile in the resulting quench solution or suspension, wherein the organic solvent is N-methyl-2-pyrrolidone (NMP).
    Type: Grant
    Filed: August 27, 2004
    Date of Patent: June 2, 2009
    Assignee: BASF Aktiengesellschaft
    Inventors: Randolf Hugo, Sabine Jourdan, Kirsten Wenz, Thomas Preiss, Alexander Weck
  • Publication number: 20090076307
    Abstract: A novel aromatic diamine compound obtained by introducing aromatic amino groups into both terminals of a specific bifunctional phenylene ether oligomer and a novel aromatic dinitro compound obtained by introducing aromatic nitro groups into both terminals of a specific bifunctional phenylene ether oligomer, these compounds being used as raw materials for obtaining high molecular weight materials having high heat resistance, a low dielectric constant, a low dielectric loss tangent and a low water absorption coefficient.
    Type: Application
    Filed: August 8, 2008
    Publication date: March 19, 2009
    Inventors: Kazuyoshi Uera, Daisuke Ohno, Kenjji Ishii
  • 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
  • Publication number: 20080161610
    Abstract: The present invention relates to a process for the preparation of compounds of formula (I) wherein the substituents are as defined in claim 1, by a) reaction of a compound of formula (II) to form a compound of formula (III) b) reaction of that compound in the presence of a base to form a compound of formula (IV) c) conversion of that compound in the presence of a reducing agent into a compound of formula (I).
    Type: Application
    Filed: February 20, 2006
    Publication date: July 3, 2008
    Applicant: SYNGENTA CROP PROTECTION, INC.
    Inventors: Harald Walter, Camilla Corsi, Josef Ehrenfreund, Clemens Lamberth, Hermann Schneider, Hans Tobler
  • 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: 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
  • Publication number: 20040199017
    Abstract: This invention relates to improved catalytic compositions suited for use in hydrogenation processes and to an improved process for hydrogenating organic compounds as in amination of alcohols or hydrogenation of nitro groups to the amine using the catalyst. The catalytic composition is more particularly an improvement in nickel catalysts promoted with palladium carried on a support. The improvement resides in including a promoting effect of a metal M and/or its oxide, selected from Zn, Cd, Cu, and Ag, typically from about 0.01 to 10% by weight of the support.
    Type: Application
    Filed: April 15, 2004
    Publication date: October 7, 2004
    Inventor: Hao Ding
  • Publication number: 20040106830
    Abstract: The present invention is to prepare efficiently 2′-amino-5′-hydroxypropiophenone corresponding to the AB-ring part of camptothecin (CPT) skeleton and a tricyclic ketone corresponding to the CDE-ring part in order to provide efficiently CPT by the total synthesis, which is a starting material for irinotecan hydrochloride and various kinds of camptothecin derivatives, and to provide stably CPT and its derivatives.
    Type: Application
    Filed: December 18, 2003
    Publication date: June 3, 2004
    Inventors: Takanori Ogawa, Hiroyuki Nishiyama, Miyuki Uchida, Seigo Sawada
  • Publication number: 20040092773
    Abstract: A process for the production of an aromatic amine which comprises the reduction of an aromatic compound containing at least two nitro groups with hydrogen in the presence of a catalyst comprising a metal of Group VIII, wherein the reaction is carried out so as to maintain 30% or less by weight of reaction intermediates and wherein the solution produced is treated to recover the aromatic amine with a purity of over 99% and a mixture comprising aromatic amine and a reaction intermediate which is recycled to the reduction step.
    Type: Application
    Filed: July 7, 2003
    Publication date: May 13, 2004
    Inventors: Anna Forlin, Antonio Beccari
  • Publication number: 20040073066
    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: Application
    Filed: July 25, 2003
    Publication date: April 15, 2004
    Inventors: Peter Zehner, Oliver Bey, Gunter Georgi, Jorn Muller
  • Patent number: 6706924
    Abstract: The invention relates to a process for the production of 1,5-naphthalenediamine and to the intermediates 4-(2-nitrophenyl)butyronitrile, 5-nitro-3,4-dihydro-1(2H)-naphthyl-imine, 5-nitroso-1-naphthylamine, 5-nitro-1-naphthylamine, 4-(2-aminophenyl)-butyronitrile, 5-amino-3,4-dihydro-1(2H)-naphthalene imine, 4-(2-nitrophenyl)ethyl butyrate and 4-(2-nitrophenyl)butyramide obtainable during the process.
    Type: Grant
    Filed: December 18, 2001
    Date of Patent: March 16, 2004
    Assignee: Bayer Aktiengesellschaft
    Inventors: Michael Schelhaas, Katrin Joschek, Manfred Jautelat, Joachim Zechlin, Dietmar Wastian
  • 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: 6653509
    Abstract: A catalyst which consists of amorphous carbon with molecular planes that have curved surfaces and contain six-membered and non-six-membered carbon rings, optionally having at least one catalytically active, low-valency metal covalently bound thereto. Methods of producing the catalyst and applications thereof are included.
    Type: Grant
    Filed: April 15, 2002
    Date of Patent: November 25, 2003
    Assignee: Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V.
    Inventors: Robert Schlögl, Michael Wohlers, Thilo Belz, Thomas Braun
  • Publication number: 20030158435
    Abstract: A method for preparing organic products from aqueous solutions, such as waste or byproduct liquid streams and waste or byproduct gas or vapor streams, uses phase transfer catalysis to transfer a chemical species in low concentration from the aqueous solution to the organic phase or the aqueous-organic interface. The system has little or no organic solvent, and the organic phase contains an electrophile which participates in the reaction. In one embodiment, the aqueous solution is contacted with the electrophile and a phase transfer catalyst and, optionally, a pH adjusting agent in the event that the chemical species in the aqueous solution is not sufficiently ionized to react with the electrophile, and optionally an organic solvent. A method for continuously converting a chemical species involves this contacting step, separating the phases, then dividing the organic phase into the product, the phase transfer catalyst, and the optional organic solvent.
    Type: Application
    Filed: September 6, 2002
    Publication date: August 21, 2003
    Inventors: Peter J. Joyce, Roman Bielski, Marc Halpern
  • Publication number: 20030114690
    Abstract: A process for the preparation of aniline compounds of formula 1
    Type: Application
    Filed: November 15, 2002
    Publication date: June 19, 2003
    Inventors: Gottfried Seifert, Thomas Rapold
  • Patent number: 6509503
    Abstract: The invention relates to processes for the preparation of compounds of formula (I) wherein R1 and R2 each independently represent a halogen atom.
    Type: Grant
    Filed: May 3, 2002
    Date of Patent: January 21, 2003
    Assignee: Aventis Cropscience S.A.
    Inventors: Jean-Erick Angel, Gilles Perrin-Janet, Pierre Leroy
  • Patent number: 6462238
    Abstract: Disclosed is a process for selectively reducing a nitrile containing organic compound that also contains a sulfone moiety, the nitrile being reduced to a primary amine.
    Type: Grant
    Filed: April 27, 2001
    Date of Patent: October 8, 2002
    Assignee: Array BioPharma, Inc.
    Inventors: Jack (ChanKou) Hwang, Eugene Tarlton, Anthony D. Piscopio
  • Patent number: 6448446
    Abstract: An improved synthesis of N,N,-disubstituted-p-phenylene-diamine (DSPDA) preferably di-n-butyl-p-phenylenediamine is disclosed. The improvement rests on the discovery that DSPDA and its salts are extremely sensitive to oxygen so that once the product DSPDA or its salt is formed, oxygen must be excluded from all manipulations.
    Type: Grant
    Filed: January 12, 2001
    Date of Patent: September 10, 2002
    Assignee: AntiCancer, Inc.
    Inventors: Li Tang, Yuying Tan
  • Patent number: 6441235
    Abstract: A process for preparing 5-amino-N,N′-bis(R)isophthalamides, where A is 2,3-dihydroxypropyl or 1,3-dihydroxyisopropyl, useful as intermediates in preparing iodinated diagnostic agents, which comprises reacting a di-lower-alkyl 5-nitroisophthalate with a compound of the formula RNH2 in the presence of a basic catalyst and without isolating the intermediate 5-nitro-N,N′-bis(R)isophthalamide, catalytically hydrogenating the latter.
    Type: Grant
    Filed: May 14, 2001
    Date of Patent: August 27, 2002
    Assignee: Amersha, Health AS
    Inventors: Edward David Parady, Karl Olaf Gelotte
  • Patent number: 6414192
    Abstract: The invention provides a process for preparing 4-aminodiphenylamine, an important starting product for synthesizing antioxidants and stabilizers in the rubber and polymer industry, by hydrogenating nitrosobenzene with hydrogen in the presence of a proton acid as catalyst and in the presence of a hydrogenating catalyst, optionally in the presence of an inert organic solvent and thermally decomposing the 4-ADPA ammonium salt produced in this way, wherein 4-ADPA is obtained. 4-aminodiphenylamine is produced in good yields and high purity by the process according to the present invention. Furthermore, no effluent is produced, which makes the process particularly economic and ecological.
    Type: Grant
    Filed: November 6, 2001
    Date of Patent: July 2, 2002
    Assignee: Bayer Aktiengesellschaft
    Inventors: Michael Schelhaas, Carl Casser, Dietmar Bielefeldt, Pieter Ooms, Joachim Haider, Manfred Jautelat, Christian Laue, Henry Giera
  • Publication number: 20020045779
    Abstract: A method of preparing 4-aminodiphylamine through an intermediate preparation of 4-nitrodiphenylamine and/or 4-nitrosodiphenylamine and/or their salts by reaction of aniline with nitobenzene in a liquid medium at a temperature of 50 to 130° C.
    Type: Application
    Filed: June 8, 2001
    Publication date: April 18, 2002
    Inventors: Emanuel Beska, Peter Toman, Karol Fiedler, Milan Hronec, Jozef Pinter
  • 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: 6262307
    Abstract: A shaped, activated metal, fixed-bed catalyst with a pore volume of 0.05 to 1 ml/g and an outer activated layer consisting of a sintered, finely-divided, catalyst alloy and optionally promoters. The catalyst alloy has metallurgical phase domains, resulting from the method of preparation of the alloy, in which the largest phase by volume has a specific interface density of more than 0.5 &mgr;m−1.
    Type: Grant
    Filed: May 19, 1998
    Date of Patent: July 17, 2001
    Assignee: Degussa-Huls Aktiengesellschaft
    Inventors: Andreas Freund, Monika Berweiler, Barbara Bender, Bernd Kempf
  • 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: 6242649
    Abstract: A continuous process for the preparation of aromatic di- and/or polyamines by catalytic hydrogenation of the corresponding aromatic di- and/or polynitro compounds with hydrogen, characterized in that, in a reactor with a catalytic fixed bed or trickle bed at a pressure between 5 and 100 bar and a reaction temperature of from 100 to 220° C. a) the aromatic di- and/or polynitro compounds, optionally in the presence of a solvent, are introduced into a product stream comprising essentially recycled hydrogenated product, water and hydrogen, and b) a part of the product stream is removed continuously from the reactor system.
    Type: Grant
    Filed: April 7, 2000
    Date of Patent: June 5, 2001
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heiko Beckhaus, Reinhard Langer
  • 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: 6156933
    Abstract: Process for the selective hydrogenation of alphatic or aromatic substrates under supercritical or near critical conditions. Hydrogenation is effected using a heterogeneous catalyst in a continuous flow reactor containing a supercritical or near critical reaction medium and selectively of product formation is achieved by varying one or more of the temperature, pressure, catalyst and flow rate.
    Type: Grant
    Filed: February 18, 1999
    Date of Patent: December 5, 2000
    Assignees: Degussa-Huls AG, Thomas Swan & Co. Ltd.
    Inventors: Martyn Poliakoff, Thomas M. Swan, Thomas Tacke, Martin G. Hitzler, Stephen K. Ross, Stefan Wieland
  • Patent number: RE44175
    Abstract: A process for preparing an optionally substituted 4-aminodiphenylamine comprising reacting an optionally substituted aniline and an optionally substituted nitrobenzene in the presence of water and a base while controlling the water content so as to ensure a molar ratio of water to the base charged of not less than about 4:1 at the start of the coupling reaction and not less than about 0.6:1 at the end of the coupling reaction to produce 4-nitrodiphenylamine and/or 4-nitrosodiphenylamine and/or salts thereof. The coupling reaction is followed by a hydrogenation reaction where the coupling reaction product is hydrogenated in the presence of a hydrogenation catalyst and added water so as to ensure a molar ratio of total water to base of at least about 4:1 at the end of hydrogenation. Aqueous and organic phases are obtained and the optionally substituted 4-aminodiphenylamine recovered from the organic phase.
    Type: Grant
    Filed: April 21, 2010
    Date of Patent: April 23, 2013
    Inventors: Roger Keranen Rains, Ralph Albert Genetti, Edward Albert Lambers, Antonius Johannes van Hengstum