Of Nitro Or Nitroso Patents (Class 564/416)
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Patent number: 11339115Abstract: 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: GrantFiled: October 8, 2018Date of Patent: May 24, 2022Assignee: BASF SEInventors: Barbara Wucher, Thomas Heidemann, Michael Friko, Christian Bechtold
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Efficient continuous process for manufacturing of 4-aminodiphenylamine from aniline and nitrobenzene
Patent number: 9102585Abstract: 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: GrantFiled: April 13, 2012Date of Patent: August 11, 2015Assignee: NOCIL LIMITEDInventors: Chinmoy Nandi, Narendra Gangal, Pramod Purohit, Vinay Ketkar, Prahlad Rao -
Publication number: 20150111976Abstract: 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: ApplicationFiled: October 31, 2014Publication date: April 23, 2015Inventors: Nicholas Leventis, Chariklia Sotiriou-Leventis, Malik Adnan Saeed
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Publication number: 20140303402Abstract: 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: ApplicationFiled: April 2, 2014Publication date: October 9, 2014Applicant: DIPHARMA FRANCIS S.r.l.Inventors: Pietro ALLEGRINI, Simone MANTEGAZZA
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Patent number: 8853455Abstract: 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: GrantFiled: March 8, 2010Date of Patent: October 7, 2014Assignee: BASF SEInventors: Alexander Korte, Jan Klaas Lohmann, Thomas Grote, Klaus Ebel, Thomas Zierke, Horst Mayer, Ralf Wazulek
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Patent number: 8614355Abstract: 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: GrantFiled: June 3, 2009Date of Patent: December 24, 2013Assignee: Bayer Technology Services GmbHInventors: Aurel Wolf, Volker Michele, Jens Aβmann, Leslaw Mleczko
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Patent number: 8609899Abstract: 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: GrantFiled: May 17, 2011Date of Patent: December 17, 2013Assignee: BASF SEInventors: Andreas Raichle, Joana Coelho Tsou, Samuel Neto, Ulrich Penzel, Steffen Oehlenschlaeger, Michael Zoellinger, Holgar Braunsberg, Stefanie Haase, Johannes Buettner
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Publication number: 20130253083Abstract: 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: ApplicationFiled: March 16, 2012Publication date: September 26, 2013Applicants: IUCF-HYU (Industry-University Cooperation Foundation Hanyang University), LG Chem, Ltd.Inventors: Yang-Kyoo Han, Jin Cho, Sang-Mi Lee, Seung-Hoon Shin
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Publication number: 20130237725Abstract: 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: ApplicationFiled: March 9, 2012Publication date: September 12, 2013Inventors: Zhang-Lin Zhou, Si-Ty Lam, Lihua Zhao
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Patent number: 8334410Abstract: 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: GrantFiled: November 28, 2008Date of Patent: December 18, 2012Assignee: Ihara Chemical Industry Co., Ltd.Inventor: Kentaro Kawazoe
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Publication number: 20120202994Abstract: 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: ApplicationFiled: April 16, 2012Publication date: August 9, 2012Inventors: Carsten Friese, Andreas Kirschning, Jürgen Wichelhaus, Sascha Volkan Ceylau
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Publication number: 20120157713Abstract: 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: ApplicationFiled: June 17, 2011Publication date: June 21, 2012Applicant: KOREA KUMHO PETROCHEMICAL CO., LTD.Inventors: Jin-Eok Kim, Seoung-IL Kim, Han Jin Kwag, Sang hee Park
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Patent number: 8188316Abstract: 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: GrantFiled: December 10, 2009Date of Patent: May 29, 2012Assignee: E. I. du Pont de Nemours and CompanyInventors: Rajiv Dhawan, Joachim C. Ritter
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Patent number: 8188317Abstract: 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: GrantFiled: December 10, 2009Date of Patent: May 29, 2012Assignee: E. I. du Pont de Nemours and CompanyInventors: Rajiv Dhawan, Joachim C. Ritter
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Patent number: 8163961Abstract: 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: GrantFiled: February 22, 2010Date of Patent: April 24, 2012Assignee: E. I. du Pont de Nemours and CompanyInventors: Rajiv Dhawan, Joachim C. Ritter
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Patent number: 8163955Abstract: 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: GrantFiled: December 10, 2009Date of Patent: April 24, 2012Assignee: E. I. du Pont de Nemours and CompanyInventors: Rajiv Dhawan, Joachim C. Ritter
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Patent number: 8158830Abstract: 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: GrantFiled: December 17, 2008Date of Patent: April 17, 2012Assignee: E. I. du Pont de Nemours and CompanyInventors: Joachim C. Ritter, Ekaterini Korovessi, Rajiv Dhawan
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Patent number: 8071812Abstract: 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: GrantFiled: December 16, 2008Date of Patent: December 6, 2011Assignee: E.I du Pont de Nemours & CompanyInventors: Joachim C. Ritter, Annalisa Hargis
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Patent number: 8030522Abstract: 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: GrantFiled: June 7, 2006Date of Patent: October 4, 2011Assignees: Bayer MaterialScience LLC, Bayer MaterialScience AGInventors: Joachim Zechlin, Bernd Pennemann, Friedhelm Steffens, Wenbin Ji
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Publication number: 20110130575Abstract: 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: ApplicationFiled: October 29, 2010Publication date: June 2, 2011Inventors: Hui Li, Cheng Gu, Stephen A. Boyd
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Patent number: 7795472Abstract: 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: GrantFiled: October 7, 2005Date of Patent: September 14, 2010Assignee: Kyorin Pharmaceutical Co., Ltd.Inventors: Takeshi Tsubuki, Kenichi Kobayashi, Hidetaka Komatsu
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Patent number: 7541497Abstract: 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: GrantFiled: August 27, 2004Date of Patent: June 2, 2009Assignee: BASF AktiengesellschaftInventors: Randolf Hugo, Sabine Jourdan, Kirsten Wenz, Thomas Preiss, Alexander Weck
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Publication number: 20090076307Abstract: 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: ApplicationFiled: August 8, 2008Publication date: March 19, 2009Inventors: Kazuyoshi Uera, Daisuke Ohno, Kenjji Ishii
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Patent number: 7504539Abstract: 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: GrantFiled: December 15, 2006Date of Patent: March 17, 2009Assignee: Flexsys America LLPInventors: Ralph D. Triplett, Roger Keranen Rains
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Publication number: 20080161610Abstract: 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: ApplicationFiled: February 20, 2006Publication date: July 3, 2008Applicant: SYNGENTA CROP PROTECTION, INC.Inventors: Harald Walter, Camilla Corsi, Josef Ehrenfreund, Clemens Lamberth, Hermann Schneider, Hans Tobler
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Patent number: 7381844Abstract: 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: GrantFiled: August 4, 2006Date of Patent: June 3, 2008Assignee: National Central UniversityInventors: Yu-Chang Liu, Chung-Yin Huang, Yu-Wen Chen
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Patent number: 7282610Abstract: 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: GrantFiled: November 24, 2004Date of Patent: October 16, 2007Assignee: Fujifilm CorporationInventors: Hiroshi Yasuoka, Hideto Mori
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Patent number: 7183439Abstract: 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: GrantFiled: May 23, 2003Date of Patent: February 27, 2007Assignee: Flexsys America L.P.Inventors: Ralph Dale Triplett, II, Roger Keranen Rains
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Publication number: 20040199017Abstract: 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: ApplicationFiled: April 15, 2004Publication date: October 7, 2004Inventor: Hao Ding
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Publication number: 20040106830Abstract: 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: ApplicationFiled: December 18, 2003Publication date: June 3, 2004Inventors: Takanori Ogawa, Hiroyuki Nishiyama, Miyuki Uchida, Seigo Sawada
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Publication number: 20040092773Abstract: 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: ApplicationFiled: July 7, 2003Publication date: May 13, 2004Inventors: Anna Forlin, Antonio Beccari
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Publication number: 20040073066Abstract: 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: ApplicationFiled: July 25, 2003Publication date: April 15, 2004Inventors: Peter Zehner, Oliver Bey, Gunter Georgi, Jorn Muller
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Patent number: 6706924Abstract: 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: GrantFiled: December 18, 2001Date of Patent: March 16, 2004Assignee: Bayer AktiengesellschaftInventors: Michael Schelhaas, Katrin Joschek, Manfred Jautelat, Joachim Zechlin, Dietmar Wastian
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Patent number: 6657085Abstract: 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: GrantFiled: November 15, 2002Date of Patent: December 2, 2003Assignee: Syngenta Crop Protection, Inc.Inventors: Gottfried Seifert, Thomas Rapold
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Patent number: 6653509Abstract: 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: GrantFiled: April 15, 2002Date of Patent: November 25, 2003Assignee: Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V.Inventors: Robert Schlögl, Michael Wohlers, Thilo Belz, Thomas Braun
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Publication number: 20030158435Abstract: 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: ApplicationFiled: September 6, 2002Publication date: August 21, 2003Inventors: Peter J. Joyce, Roman Bielski, Marc Halpern
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Publication number: 20030114690Abstract: A process for the preparation of aniline compounds of formula 1Type: ApplicationFiled: November 15, 2002Publication date: June 19, 2003Inventors: Gottfried Seifert, Thomas Rapold
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Patent number: 6509503Abstract: The invention relates to processes for the preparation of compounds of formula (I) wherein R1 and R2 each independently represent a halogen atom.Type: GrantFiled: May 3, 2002Date of Patent: January 21, 2003Assignee: Aventis Cropscience S.A.Inventors: Jean-Erick Angel, Gilles Perrin-Janet, Pierre Leroy
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Patent number: 6462238Abstract: 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: GrantFiled: April 27, 2001Date of Patent: October 8, 2002Assignee: Array BioPharma, Inc.Inventors: Jack (ChanKou) Hwang, Eugene Tarlton, Anthony D. Piscopio
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Patent number: 6448446Abstract: 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: GrantFiled: January 12, 2001Date of Patent: September 10, 2002Assignee: AntiCancer, Inc.Inventors: Li Tang, Yuying Tan
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Patent number: 6441235Abstract: 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: GrantFiled: May 14, 2001Date of Patent: August 27, 2002Assignee: Amersha, Health ASInventors: Edward David Parady, Karl Olaf Gelotte
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Patent number: 6414192Abstract: 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: GrantFiled: November 6, 2001Date of Patent: July 2, 2002Assignee: Bayer AktiengesellschaftInventors: Michael Schelhaas, Carl Casser, Dietmar Bielefeldt, Pieter Ooms, Joachim Haider, Manfred Jautelat, Christian Laue, Henry Giera
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Publication number: 20020045779Abstract: 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: ApplicationFiled: June 8, 2001Publication date: April 18, 2002Inventors: Emanuel Beska, Peter Toman, Karol Fiedler, Milan Hronec, Jozef Pinter
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Patent number: 6278022Abstract: 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 groupType: GrantFiled: November 1, 1999Date of Patent: August 21, 2001Assignee: CK Witco CorporationInventor: Haihong Jin
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Patent number: 6262307Abstract: 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: GrantFiled: May 19, 1998Date of Patent: July 17, 2001Assignee: Degussa-Huls AktiengesellschaftInventors: Andreas Freund, Monika Berweiler, Barbara Bender, Bernd Kempf
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Patent number: 6258982Abstract: 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: GrantFiled: March 10, 1999Date of Patent: July 10, 2001Assignee: Novartis AGInventors: Peter Baumeister, Urs Siegrist, Martin Studer
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Patent number: 6242649Abstract: 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: GrantFiled: April 7, 2000Date of Patent: June 5, 2001Assignee: Bayer AktiengesellschaftInventors: Heiko Beckhaus, Reinhard Langer
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Patent number: 6232501Abstract: 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: GrantFiled: September 14, 2000Date of Patent: May 15, 2001Assignee: Ciba Specialty Chemicals CorporationInventors: Heinz Steiner, Markus Benz, Hans-Peter Jalett, Marc Thommen
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Patent number: 6156933Abstract: 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: GrantFiled: February 18, 1999Date of Patent: December 5, 2000Assignees: Degussa-Huls AG, Thomas Swan & Co. Ltd.Inventors: Martyn Poliakoff, Thomas M. Swan, Thomas Tacke, Martin G. Hitzler, Stephen K. Ross, Stefan Wieland
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Patent number: RE44175Abstract: 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: GrantFiled: April 21, 2010Date of Patent: April 23, 2013Inventors: Roger Keranen Rains, Ralph Albert Genetti, Edward Albert Lambers, Antonius Johannes van Hengstum