Preparing Directly By Amination Patents (Class 564/395)
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Patent number: 11306262Abstract: Disclosed are a pretreatment method and system for a fraction oil for the production of alkylbenzene, the method comprising: adding a fraction oil, a weak base solution and an inorganic salt solution into a reactor, and leaving same to stand and layering same after the reaction is complete; adding water and an inorganic salt solution into an oil phase for washing with water; extracting same with a polar solvent having a high boiling point, and then adsorbing same with an adsorbent to separate oxygen-containing compounds in the neutral fraction oil; sending the extraction agent containing the oxygen-containing compounds to an extraction agent recovery unit; and then sending the neutral fraction oil to an alkylation reactor for a reaction.Type: GrantFiled: June 11, 2019Date of Patent: April 19, 2022Assignee: INNER MONGOLIA YITAI COAL-BASED NEW MATERIALS RESEARCH INSTITUTE CO., LTD.Inventors: Zhen Qian, Jingwei Wu, Xiaolong Zhang, Jingquan Zhang, Juncheng Li, Qinge Jian
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Patent number: 9440932Abstract: A new process for making agrochemically important N-[2,4-dichloro-5-[4-(difluoro methyl)-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl] phenyl]methanesulfonamide by reacting 1-(5-amino-2,4-dichlorophenyl)-4,5-dihydro-4-difluoromethyl-3-methyl-1,2,4-triazol-5(1H)-one and methanesulfonyl chloride in water using an inorganic base to dynamically control the reaction pH and in the presence of a phase transfer catalyst suspended in an 1:1 aromatic solution.Type: GrantFiled: July 23, 2014Date of Patent: September 13, 2016Inventor: Bomi P Framroze
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Patent number: 9006489Abstract: Method for pretreating the copper-based catalyst having the steps of dehydrating the copper-based catalyst at an elevated temperature, reducing the dehydrated copper-based catalyst with hydrogen, and passivating the activated copper-based catalyst to obtain a catalyst suitable for N-alkylation. The dehydration and reduction steps may be conducted simultaneously.Type: GrantFiled: June 15, 2011Date of Patent: April 14, 2015Assignee: Jiangsu Sinorgchem Technology Co., Ltd.Inventor: Shiming Gao
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Publication number: 20140371418Abstract: The invention generally relates to biological engineering of microorganisms and production of chemical compounds therefrom. More particularly, the invention relates to novel genetically engineered microorganisms for the fermentative production of p-aminobenzoic acid and related compounds from fermentable carbon substrates. The biologically derived PABA and related compounds from fermentable carbon substrates can be used in a number of applications including as a food supplement or raw materials for the syntheses of other industrial chemicals or polymers.Type: ApplicationFiled: January 4, 2013Publication date: December 18, 2014Applicant: pAromatics, LLCInventors: Wing On Ng, Shingo Watanabe, Robert W.R. Humphreys, Steven C. Slater
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Patent number: 8901354Abstract: The invention relates to a method for producing a N-substituted amine compound by catalyzed alkylation. The method uses amine and alcohol or two kinds of amines as the reaction materials, employs composite metal oxides catalyst at a reaction temperature of 80-180° C. to catalyze the reaction for 6-36 hours, so as to produce the N-substituted amine compound. The reaction condition of the method of the invention is relatively moderate, using a catalyst made of cheap non-noble metals, which is non-caustic and easy to be separated and reused. The reaction does not need any medium and has relatively high conversion rate and selectivity.Type: GrantFiled: December 28, 2012Date of Patent: December 2, 2014Assignee: Lanzhou Institute of Chemical Physics, Chinese Academy of SciencesInventors: Feng Shi, Xinjiang Cui, Hangkong Yuan, Youquan Deng
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Patent number: 8766008Abstract: Process for preparing 2,2-difluoroethylamine, comprising the following steps: (i) mixing 2,2-difluoro-1-chloroethane and gaseous, liquid or supercritical ammonia in a pressure-stable, closed reaction vessel under a pressure in the range from 10 to 180 bar; (ii) reacting the reaction mixture at a reaction temperature in the range from 80° C. to 200° C.; (iii) letting down the reaction mixture and isolating 2,2-difluoroethylamine.Type: GrantFiled: January 11, 2012Date of Patent: July 1, 2014Assignee: Bayer Cropscience AGInventors: Norbert Lui, Rafael Warsitz, Christian Funke, Christian Severins
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Patent number: 8614354Abstract: There is described a process for the preparation of cinacalcet hydrochloride (I) which includes the steps of: a) reacting (R)-(+)-1-(1-naphthyl)ethylamine (II) with 3-[3-(trifluoromethyl)phenyl]propenaldehyde (III) to afford the non isolated intermediate (R)—N-[3-[3-(trifluoromethyl)phenyl]-2-propenylimino-N-[1-(1-naphthyl)ethylamine (IV); b) reducing the non isolated intermediate (R)—N-[3-[3-(trifluoromethyl)phenyl]-2-propenylimino-N-[-1-(1-naphthyl)ethylamine (IV) with a sequential addition of:—a solution of sodium borohydride, methanol and a base,—oxalic acid and—a base to obtain (R)—N-[3-[3-(tifluoromethyl)phenyl]-2-propenyl]-1-(1-naphthyl)ethylamine (V) by passing through the precipitation of the oxalate salt of compound (V) after the addition of oxalic acid; c) hydrogenating (R)—N-[3-[3-(trifluoromethyl)phenyl]-2-propenyl]-1-(1-naphthyl)ethylamine (V) thus obtaining (R)—N-(3-(3-(trifluoromethyl)phenyl]propyl]-1-(1-naphthyl)ethylamine cinacalcet base (VI), which is retaken in ethyl acetate; and d) treatiType: GrantFiled: June 18, 2008Date of Patent: December 24, 2013Assignee: Erregierre S.p.A.Inventors: Massimo Ferrari, Marcello Ghezzi, Matteo Bonaldi
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Patent number: 8592631Abstract: A process for synthesizing 2-methoxymethyl-1,4-benzenediamine, its derivatives of formula (IV) and the salts thereof, which comprises a reductive amination step. The preferred final product is 2-methoxymethyl-1,4-benzenediamine of formula (IV-a). These compounds may be used as primary intermediates in compositions for dyeing keratin fibers.Type: GrantFiled: January 28, 2011Date of Patent: November 26, 2013Assignee: The Procter & Gamble CompanyInventors: John Michael Gardlik, Garry Steven Garrett, Bryan Patrick Murphy, John Michael Janusz, John August Wos
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Patent number: 8399680Abstract: The invention relates to a method for preparing arylamines and, in particular, a method for preparing aniline and anilines substituted on the aromatic ring from ammonia, under easily-industrialized mild conditions with good selectivity and yields, in the presence of a catalytic system including a copper complex.Type: GrantFiled: September 24, 2008Date of Patent: March 19, 2013Assignee: Centre National de la Recherche Scientifique (C.N.R.S.)Inventors: Marc Taillefer, Ning Xia
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Publication number: 20130018204Abstract: Disclosed is an edge-functionalized graphitic material manufactured by using a mechanochemical process. The edge-functionalized graphitic material is manufactured by pulverizing graphite in the presence of a variety of atmospheric agents in the form of gas phase, liquid phase, or solid phase. The edge-functionalized graphitic material, which is a precursor applicable into various fields, is expected to replace the prior art oxidized graphite.Type: ApplicationFiled: October 10, 2011Publication date: January 17, 2013Applicant: UNIST Academy-Industry Research CorporationInventors: In Yup JEON, Jong Beom BAEK
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Patent number: 8304550Abstract: Described is a process for preparing diaryl ethers of the formula (I) Ar—O—Ar???(I) In which Ar is an aryl or substituted aryl group and Ar? is an aryl, substituted aryl, heteroaryl or substituted heteroaryl group, by reacting an aryl of formula (II) or a aryloxy salt of formula (III) Ar—OH??(II) Ar—OR??(III) In which Ar has the same meaning as in formula (I) and R is an alkali metal, with an aryl or heteroaryl bromide of formula (IV) Ar?—Br??(IV) In which Ar? has the same meaning as in formula (I), characterized in that the reaction is carried out in the presence of a copper(I)salt and a 1-substituted imidazole as catalyst system.Type: GrantFiled: November 21, 2008Date of Patent: November 6, 2012Assignee: Saltigo GmbHInventors: Alain Cotte, Nikolaus Muller, Matthias Gotta, Matthias Beller, Thomas Schareina, Alexander Zapf
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Publication number: 20110172463Abstract: Methods of producing TATB are disclosed. The method comprises providing acid wet TNPG and distilling water from the acid wet TNPG. The TNPG is reacted with an alkoxylating agent to form a solution of 1,3,5-trialkoxy-2,4,6-trinitrobenzene solution, which is reacted with an aminating agent. An alternate method comprises nitrating phloroglucinol in a first vessel to produce TNPG, which is reacted with an alkoxylating agent in a second vessel to form a solution comprising 1,3,5-trialkoxy-2,4,6-trinitrobenzene and at least one of at least one volatile byproduct and at least one nonvolatile byproduct. The at least one of at least one volatile byproduct and at least one nonvolatile byproduct is removed in situ. The 1,3,5-trialkoxy-2,4,6-trinitrobenzene is reacted with an aminating agent.Type: ApplicationFiled: May 7, 2007Publication date: July 14, 2011Applicant: ALLIANT TECHSYSTEMS INC.Inventors: Stephen P. Velarde, Vincent E. Mancini
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Publication number: 20100317894Abstract: Methods of producing 1,3,5-triamino-2,4,6-trinitrobenzene (TATB), from alkoxy derivatives of phloroglucinol, such as 5-methoxyresorcinol, 3,5-dimethoxyphenol, or 1,3,5-trimethoxybenzene, are disclosed. The alkoxy derivatives may be exposed to and directly nitrated with a reaction mixture comprising a sulfuric acid solution and at least one nitrate salt. The nitrated alkoxy derivative of phloroglucinol may be alkoxylated and, thereafter, aminated to produce the TATB.Type: ApplicationFiled: June 15, 2009Publication date: December 16, 2010Applicant: ALLIANT TECHSYSTEMS INC.Inventors: Nicholas A. Straessler, Stephen P. Velarde
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Patent number: 7803953Abstract: To provide a process for preparing an arylamine highly selectively and highly efficiently, which is also industrially superior without a fear of a side reaction when a strong base is employed. An aryl compound having an active group is reacted with an amine compound in the presence of a base by means of a catalyst for producing an arylamine which comprises a palladium compound having a tertiary phosphine group and a phase-transfer catalyst.Type: GrantFiled: June 1, 2007Date of Patent: September 28, 2010Assignee: Tosoh CorporationInventors: Takanori Miyazaki, Masakazu Nishiyama, Naoki Matsumoto
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Publication number: 20090143594Abstract: Described is a process for preparing diaryl ethers of the formula (I) Ar—O—Ar???(I) In which Ar is an aryl or substituted aryl group and Ar? is an aryl, substituted aryl, heteroaryl or substituted heteroaryl group, by reacting an aryl of formula (II) or a aryloxy salt of formula (III) Ar—OH ??(II) Ar—OR ??(III) In which Ar has the same meaning as in formula (I) and R is an alkali metal, with an aryl or heteroaryl bromide of formula (IV) Ar?—Br ??(IV) In which Ar? has the same meaning as in formula (I), characterized in that the reaction is carried out in the presence of a copper(I)salt and a 1-substituted imidazole as catalyst system.Type: ApplicationFiled: November 21, 2008Publication date: June 4, 2009Applicant: SALTIGO GMBHInventors: Alain Cotte, Nikolaus Muller, Matthias Gotta, Matthias Beller, Thomas Schareina, Alexander Zapf
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Patent number: 7538251Abstract: Severely sterically hindered secondary aminoether alcohols are prepared by a process comprising reacting a ketene with sulfuric acid to produce an anhydride which is then reacted with, to cleave the ring of, a dioxane to yield a cleavage product which is then aminated using an amine, followed by hydrolysis with a base to yield the desired severely sterically hindered secondary aminoether alcohol.Type: GrantFiled: February 1, 2005Date of Patent: May 26, 2009Assignee: ExxonMobil Research and Engineering CompanyInventors: Michael Siskin, Alan Roy Katritzky, Kostyantyn Mykolayevich Kirichenko, Adeana Richelle Bishop, Christine Nicole Elia
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Publication number: 20090124747Abstract: The present disclosure describes carbon nanotube materials and condensation polymers having at least one bridge between carbon nanotubes. Carbon nanotube materials comprise a plurality of functionalized single-wall carbon nanotubes linked to at least one other single-wall carbon nanotube by at least one bridge. The at least one bridge comprises at least one amine functionality bonded to the functionalized single-wall carbon nanotubes. The amine functionality may be alkyl or aryl. Carbon nanotube condensation polymers having at least one bridge between single-wall carbon nanotubes are also disclosed. The bridges in the condensation polymers comprise an amine functionality and a condensation agent.Type: ApplicationFiled: October 14, 2008Publication date: May 14, 2009Applicant: William Marsh Rice UniversityInventor: Valery N. Khabashesku
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Patent number: 7524990Abstract: Severely sterically hindered secondary aminoether alcohols are prepared by reacting organic carboxylic, organic carboxylic acid halides, acid anhydrides or a ketene with an alkyl, alkaryl or alkylhalo sulfonate to yield a sulfonic-carboxylic anhydride compound which is then reacted with a dioxane to cleave the ring of the dioxane, yielding a cleavage product which cleavage product is then aminated with an alkylamine and hydrolyzed with base to yield the severely sterically hindered secondary aminoether alcohol.Type: GrantFiled: February 1, 2005Date of Patent: April 28, 2009Assignee: ExxonMobil Research and Engineering CompanyInventors: Michael Siskin, Alan Roy Katritzky, Kostyantyn Mykolayevich Kirichenko, Adeana Richelle Bishop, Christine Nicole Elia
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Publication number: 20080183017Abstract: Improved methods for making hole transport molecules (HTMs) that are incorporated into imaging members, such as layered photoreceptor devices, to increase the photoreceptor's “hole mobility,” or its ability to move charge, across its charge transport layer (CTL). Embodiments pertain to a continuous process for making N,N-diphenyl-4-biphenylamine and a system for performing the same.Type: ApplicationFiled: January 25, 2007Publication date: July 31, 2008Applicant: Xerox CorporationInventors: Timothy P. Bender, Emily L. Moore, Jennifer A. Coggan, Frank Ping-Hay Lee, David Borbely
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Patent number: 7358399Abstract: A process is described for the preparation of N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenyl-propaneamine comprising substitution of the sulfonyloxy group of the compound of the formula in which the substituents R and R? have the meanings stated in the description, in a solvent comprising an ionic liquid, to yield the tertiary amine of the formula and the subsequent deprotection thereof.Type: GrantFiled: October 6, 2005Date of Patent: April 15, 2008Assignee: Chemi SPAInventors: Stefano Turchetta, Umberto Ciambecchini, Pietro Massardo
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Publication number: 20080039633Abstract: The invention relates to a process for preparing arylamines or heteroarylamines or arylamides or heteroarylamides by cross-coupling of primary or secondary amines or amides with substituted aryl or heteroaryl compounds in the presence of a Brønsted base and a catalyst or precatalyst, wherein the catalyst comprises a) a transition metal, a complex, a salt or a compound of this transition metal selected from the group consisting of Ni, Pd and b) at least one ligand selected from the group consisting of bidentate bis(phosphino)alkanediyls having the following formula in a solvent or solvent mixture, where the radicals Ar1-4 are each, independently of one another, an aryl or heteroaryl substituent selected from the group consisting of phenyl, naphthyl, pyridyl and biphenyl or Ar1-4 is hydrogen, C1-, C2-alkyl, straight-chain, branched or cyclic C3-C8-alkyl, and L is an alkanediyl bridge which has from 1 to 20 carbon atoms.Type: ApplicationFiled: August 9, 2007Publication date: February 14, 2008Inventors: Joerg JUNG, Andreas Meudt, Bernd Wilheilm Lehnemann
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Patent number: 7312331Abstract: Stable carbene ligands are provided having a carbene center flanked by a quaternary carbon and an amino group, and having utility in the preparation of various transition metal complexes.Type: GrantFiled: June 7, 2006Date of Patent: December 25, 2007Assignee: The Regents of the University of CaliforniaInventors: Guy Bertrand, Vincent Lavallo, Yves Canac
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Publication number: 20070282111Abstract: To provide a process for preparing an arylamine highly selectively and highly efficiently, which is also industrially superior without a fear of a side reaction when a strong base is employed. An aryl compound having an active group is reacted with an amine compound in the presence of a base by means of a catalyst for producing an arylamine which comprises a palladium compound having a tertiary phosphine group and a phase-transfer catalyst.Type: ApplicationFiled: June 1, 2007Publication date: December 6, 2007Applicant: TOSOH CORPORATIONInventors: Takanori Miyazaki, Masakazu Nishiyama, Naoki Matsumoto
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Patent number: 7186864Abstract: A compound of Formula (IA) or Formula (IB) wherein R1, R2, R3, R4, R5, R6, R7, and R8 are as defined herein, or a tautomer, prodrug, solvate, or salt thereof; pharmaceutical compositions containing such compounds, and methods of modulating the glucocorticoid receptor function and methods of treating disease-states or conditions mediated by the glucocorticoid receptor function or characterized by inflammatory, allergic, or proliferative processes in a patient using these compounds.Type: GrantFiled: May 28, 2003Date of Patent: March 6, 2007Assignee: Boehringer Ingelheim Pharmaceuticals, Inc.Inventors: Thomas Martin Kirrane, Jr., Daniel Kuzmich, John Robert Proudfoot, David Thomson
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Patent number: 7053246Abstract: Process for preparing a symmetrical secondary amine by reaction of a primary amine in the presence of hydrogen and a catalyst whose preparation has involved precipitation of catalytically active components onto monoclinic, tetragonal or cubic zirconium dioxide.Type: GrantFiled: December 10, 2003Date of Patent: May 30, 2006Assignee: BASF AktiengesellschaftInventors: Till Gerlach, Frank Funke, Christoph Benisch, Johann-Peter Melder
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Patent number: 7005449Abstract: The present invention concerns novel pharmaceutically active compounds, pharmaceutical compositions containing the same, the compounds for use as medicaments, and use of the compounds for the manufacture of specific medicaments. The present invention also concerns a method of treatment involving administration of the compounds. Specifically, the compounds are pharmaceutically acceptable salts of tolterodine or hydroxytolterodine, wherein the salt is of an acid selected from the group consisting of aliphatic mono- and dicarboxylic acids comprising from 7 to 24 carbon atoms, alkanedisulfonic acids comprising from 2 to 4 carbon atoms, naphthoic acid derivatives comprising from 11 to 27 carbon atoms, maleic acid and fumaric acid.Type: GrantFiled: April 23, 2002Date of Patent: February 28, 2006Assignee: Pharmacia & Upjohn CompanyInventors: Michael Hawley, Satish Kumar Singh, Walter Morozowich, Mark P. Warchol
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Patent number: 6933409Abstract: Noble metal/reducible metal oxide catalysts effective for the direct amination of aromatic hydrocarbons and heterocyclic analogs thereof are disclosed. In one embodiment, the cataloxidant comprises a noble metal selected from Pd, Rh, Ir and/or Ru and a reducible metal oxide. In another embodiment, the cataloxidant comprises a noble metal and a reducible oxide of a metal selected from Ni, Mn, V, Ce, Th, Pr, Te, Re, Co, Fe, Cu and/or Bi. A preferred cataloxidant comprises one or more noble metals selected from Pd, Rh, Ir and/or Ru, in combination with nickel oxide and/or manganese oxide. In preferred applications, benzene can be aminated in the presence of the cataloxidants to form aniline. A benzene conversion of at least 5% is achieved, with more than 90% selectivity for aniline. Significantly, the cataloxidant can be regenerated without a substantial loss of performance.Type: GrantFiled: May 15, 2000Date of Patent: August 23, 2005Assignees: Symyx Technologies, Inc., Bayer AGInventors: Damodara M. Poojary, Ramesh Borade, Alfred Hagemeyer, Xiao Ping Zhou, Christopher E. Dube, Ulrich Notheis, Ralph Armbrust, Christian Rasp, David M. Lowe
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Patent number: 6822128Abstract: A method is disclosed for maintaining a volumetric gas to liquid ratio in a segmented gas/liquid flow along a reactor of monolithic catalyst beds in series. The present invention includes the steps of: initiating the segmented gas/liquid flow at a first end of the reactor by introducing feed liquid and feed gas both at a predetermined volume and a predetermined flow rate; injecting an additional amount of gas at least once into any of the spaces between catalyst beds; and combining the segments of the segmented gas/liquid flow at a second end of the reactor. The injection of gas is controlled such that the segmented gas/liquid flow can be maintained near or at the Taylor regime.Type: GrantFiled: December 20, 2001Date of Patent: November 23, 2004Assignee: Corning IncorporatedInventors: Didier Letourneur, Charles M. Sorensen, Jr., Pierre Woehl
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Publication number: 20040229958Abstract: A process is disclosed for manufacturing N-methyl-N-phenylaminoacrolein of formula (I) 1Type: ApplicationFiled: May 7, 2004Publication date: November 18, 2004Applicant: Clariant Life Science Molecules (Italia) S.p.A.Inventors: Aldo Banfi, Alfredo Mancini
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Publication number: 20040162444Abstract: A process is disclosed for preparing ortho substituted phenylamines comprising contacting phenylhydroxylamine, optionally substituted with at least one inert substituent, with a nucleophilic reagent in the presence of a manganese oxide at a temperature between about 10° C. and about 170° C. and a pressure from subatmospheric to superatmospheric such that an ortho substituted phenylamine, optionally correspondingly substituted with at least one inert substituent, is predominantly formed.Type: ApplicationFiled: January 30, 2004Publication date: August 19, 2004Inventors: Russell E. Malz, Ranjit Kumar, Luis Javier Garces, Steven L. Suib
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Publication number: 20040106807Abstract: Disclosed are methods of making aryl intermediate compounds of the formula (A) which are useful in the production of heteroaryl ureas, 1Type: ApplicationFiled: November 17, 2003Publication date: June 3, 2004Applicant: Boehringer Ingelheim Pharmaceuticals, Inc.Inventors: Jinhua J. Song, Zhulin Tan, Nathan K. Yee
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Publication number: 20040092772Abstract: A process for the regeneration of a zeolitic catalyst which is at least partially exhausted by use in the synthesis of optionally substituted methylenedianiline (MDA) and derivatives thereof, or of a mixture of optionally substituted MDA and derivatives thereof, with a higher homologous product the process involving washing said catalyst with an aromatic compound having at least one substitutent on the aromatic ring having activating characteristics with respect to the electrophilic substitution, in liquid or at least partially liquid phase.Type: ApplicationFiled: September 4, 2003Publication date: May 13, 2004Inventors: Carlo Perego, Alberto De Angelis, Otello Faris, Aldo Bosetti
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Patent number: 6723880Abstract: A process for producing secondary amines of the formula R1R2N—A—NH—A—NR1R2, where R1 and R2 are linear or branched C1-20-alkyl radicals, optionally substituted with from 1 to 5 phenyl groups; or cyclohexyl radicals; or together with the nitrogen atom to which they are bound, form a 3 to 7 membered saturated ring, optionally containing further hetero atoms selected from the group consisting of N, O and S, and optionally substituted with from 1 to 5 C1-2-alkyl groups. The group A is a linear or branched C2-20-alkylene group, optionally containing from 1 to 5 phenylene groups; or a radical of the formula —CH(R3)—[CH2]k—X—[CH(R3)—[CH2]k—X]m—CH(R3)—[CH2]k—, where R3 is H or CH3, X is O, S or NR4, R4 is H or a linear or branched C1-4-alkyl group, k is 1 or 2, and m is an integer from 0 to 4; or a group of the formula where n, o, p, and q are, independently, integers from 1 to 4.Type: GrantFiled: June 19, 2002Date of Patent: April 20, 2004Assignee: BASF AktiengesellschaftInventors: Peter Neumann, Johann-Peter Melder, Christoph Benisch, Arthur Höhn, Joachim Pfeffinger
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Publication number: 20030236437Abstract: A process for the preparation of a sulfonamide of formula (II), comprising reacting at elevated temperature an aniline of formula (I), with a sulfonating agent A of the formula R1—SO2—Z in the presence of a catalytic amount of either: (i) an amide B-1, other than N,N-dimethylformamide, or (ii) a high boiling tertiary amine B-2. Also provided in accordance with the present invention are processes for preparing sulfonamides of formula (II) by reacting an aniline of formula (I) with sulfanating agent A of the formula R1—SO2—Z in the presence of N,N-dimethylformamide, at a temperature in the range of about 120° C. to about 160° C. for about three to about seven hours. X, Y, Z, R and R1 are defined herein.Type: ApplicationFiled: June 2, 2003Publication date: December 25, 2003Inventors: Leland A. Smeltz, Thomas C. Sedergran, Harold C. Jarrow
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Patent number: 6646163Abstract: In a method for producing xylylenediamine by hydrogenating phthalonitrile separated from a gas produced by causing xylene to react with ammonia and oxygen-containing gas in the presence of a catalyst, (1) the gas is brought into contact with an organic solvent to trap phthalonitrile; (2) a liquid in which phthalonitrile is trapped is distilled, to thereby recover phthalonitrile and the organic solvent from the top of the column and separate at the bottom of the column impurities having boiling points higher than that of phthalonitrile; (3) the organic solvent is recovered from the top of the column and liquefied phthalonitrile of high purity is recovered at the bottom of the column; and (4) the phthalonitrile is hydrogenated after mixing with liquid ammonia and at least one solvent selected from aromatic hydrocarbon and saturated hydrocarbon. Thus, high-purity phthalonitrile is produced at high yield industrially efficiently.Type: GrantFiled: July 2, 2002Date of Patent: November 11, 2003Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Kenichi Nakamura, Kazuhiko Amakawa, Takuji Shitara
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Publication number: 20030139627Abstract: Disclosed is a process for the enantioselective production of an optically active amino compound by the amination of the C—H bond of an organic compound. The amino compound is produced by converting the C—H bond at the allyl position of an alkene or the C—H bond at the benzyl position of an alkylarene to the corresponding C—N bond, using a salen-manganese complex as the catalyst and N-substituted iminoaryliodinane as the amination agent. Both the catalytic activity and the enantioselectivity are very high when there is used a catalyst in which the 3- and 5-positions of the salicylaldehyde moiety of the salen ligand are substituted with an electron-withdrawing group, particularly with a halogen atom.Type: ApplicationFiled: November 7, 2002Publication date: July 24, 2003Inventors: Tsutomu Katsuki, Yoshinori Kohmura
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Publication number: 20030135052Abstract: Disclosed is a method for preparing tertiary amine compounds from primary amines and nitrites in the presence of hydrogen gas and a metal catalyst, or metal-containing catalyst composition, at a temperature from about 50° C. to about 200° C. and at a pressure from about 100 psig to 1500 psig. The primary amines and the nitrites used in the process may be diamines and/or dinitriles, or may be combinations of primary amines and/or nitrites. Also disclosed are novel tertiary amine compounds made by the described method.Type: ApplicationFiled: November 13, 2001Publication date: July 17, 2003Inventors: Kelley Moran Whittle, Alan Martin Allgeier, THOMAS PAPIN GANNETT, DAVID PAGE HIGLEY
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Publication number: 20030130536Abstract: Disclosed is method for increasing the efficiency of a dirhodium catalyst. The method includes providing a dirhodium catalyst, providing an organic ester, and contacting the dirhodium catalyst and the organic ester under conditions effective to increase the efficiency of the dirhodium catalyst. The organic ester is selected such that it is not a substrate for catalysis by the dirhodium catalyst. Dirhodium catalyst compositions which include a dirhodium catalyst and an organic ester are also disclosed. In these compositions, the organic ester is not a substrate for catalysis by the dirhodium catalyst. The method and compositions can be used in a number of reactions, including insertion reactions (e.g., C—H insertions, Si—H insertions, O—H insertions, and N—H insertions) cyclopropanation reactions, annulations (e.g., [3+2] annulations and [3+4] annulations), and &ohgr;,&ohgr;-diarylalkanoate syntheses.Type: ApplicationFiled: August 27, 2002Publication date: July 10, 2003Inventor: Huw M. L. Davies
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Publication number: 20020188158Abstract: A method for preparing lithium amide is described in which in a first method step lithium metal is reacted with ammonia to form lithium bronze and in a second method step the lithium bronze is reacted with a 1,3-diene or an arylolefin in the presence of a solvent.Type: ApplicationFiled: March 5, 2002Publication date: December 12, 2002Inventors: Wilfried Weiss, Dirk Dawidowski
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Patent number: 6476269Abstract: A method for producing xylylenediamine by hydrogenating phthalonitrile synthesized through ammoxidation of xylene, wherein phthalonitrile is trapped in an organic solvent (A) by bringing a gas produced through ammoxidation into direct contact with the organic solvent (A), and hydrogenation including adding liquid ammonia to the resultant mixture is carried out without separation of phthalonitrile trapped in the organic solvent (A). Through this method, the phthalonitrile can be readily recovered from the produced gas and at high yield without need for new equipment, and xylylenediamine can be efficiently produced through hydrogenation. Xylylenediamine of high purity can be obtained by subjecting the produced xylylenediamine to extraction by use of an organic solvent (B) and water.Type: GrantFiled: September 17, 2001Date of Patent: November 5, 2002Assignee: Mitsubishi Gas Chemical Co. Inc.Inventors: Kenichi Nakamura, Susumu {overscore (O)}tsuka, Fumisada Kosuge, Takuji Shitara, Kazuhiko Amakawa
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Patent number: 6387545Abstract: A tertiary amine imparted quaterphenyl compound represented by the following formula: where R1 and R2, which can be different or the same, are hydrogen, C1-C5 alkyl, or C6-C12 aryl, and R3 is hydrogen, C1-C5 alkyl, a vinyl group, or an aryl vinyl group. The tertiary amine-imparted quaterphenyl compound exhibits good blue light luminescence and hole-transportability, and can be used in forming a hole-transporting layer, a blue light emitting layer, or a combined hole-transporting and light emitting layer of a light emitting organic electroluminescent device. Examples of the quaterphenyl compounds include N-quaterphenyl-4-yl-N,N-diphenylamine, N-(4′-(1,1-diphenylvinyl)quaterphenyl-4-yl)-N-phenyl-N-(m-tolyl)amine, or N-quaterphenyl-4-yl-N-phenyl-N-(m-tolyl)amine.Type: GrantFiled: April 14, 1999Date of Patent: May 14, 2002Assignee: Industrial Technology Research InstituteInventors: Jia-Ming Liu, Huan-Lurn Hsieh, Po-Yen Lu, Ying-Chuan Wang
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Publication number: 20020038054Abstract: A method for producing xylylenediamine by hydrogenating phthalonitrile synthesized through ammoxidation of xylene, wherein phthalonitrile is trapped in an organic solvent (A) by bringing a gas produced through ammoxidation into direct contact with the organic solvent (A), and hydrogenation including adding liquid ammonia to the resultant mixture is carried out without separation of phthalonitrile trapped in the organic solvent (A). Through this method, the phthalonitrile can be readily recovered from the produced gas and at high yield without need for new equipment, and xylylenediamine can be efficiently produced through hydrogenation. Xylylenediamine of high purity can be obtained by subjecting the produced xylylenediamine to extraction by use of an organic solvent (B) and water.Type: ApplicationFiled: September 17, 2001Publication date: March 28, 2002Inventors: Kenichi Nakamura, Susumu Otsuka, Fumisada Kosuge, Takuji Shitara, Kazuhiko Amakawa
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Publication number: 20020035295Abstract: The present invention provides an activator in arylamination using a palladium compound as a catalyst, which is superior to conventional phosphines in stability and performance. With the phosphine sulfide as an activator, an arylamination reaction achieves improved selectivity to produce a desired aromatic amine in an obviously increased yield as compared with a reaction using the corresponding phosphine compound. Moreover, the phosphine sulfide of the invention is impervious to oxidation and exists stably in air and therefore sufficiently withstands use on an industrial scale.Type: ApplicationFiled: September 6, 2001Publication date: March 21, 2002Applicant: TAKASAGO INTERNATIONAL CORPORATIONInventors: Mitsuhiko Fujiwara, Ken Suzuki, Tohru Kobayashi, Yoji Hori, Toshimitsu Hagiwara
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Publication number: 20020019551Abstract: This invention discloses a process for making dilithium initiators in high purity. This process can be conducted in the absence of amines which is desirable since amines can act as modifiers for anionic polymerizations. The dilithium compounds made are highly desirable because they are soluble in aromatic solvents. The present invention more specifically discloses a process for synthesizing a dilithium initiator which comprises reacting diisopropenylbenzene with a tertiary alkyl lithium compound in an aromatic solvent at a temperature which is within the range of about 0° C. to about 100° C. The present invention further discloses a process for synthesizing m-di-(1-methyl-3,3-dimethylbutyllithio) benzene which comprises reacting diisopropenylbenzene with tertiary-butyllithium in an aromatic solvent at a temperature which is within the range of about 0° C. to about 100° C.Type: ApplicationFiled: May 25, 2001Publication date: February 14, 2002Inventors: Adel Farhan Halasa, Wen-Liang Hsu
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Patent number: 6316673Abstract: The present invention relates to the production of aminodiphenyl-amines resulting in good yields and high purity levels when aromatic amines are reacted with nitrohalobenzenes in the presence of a palladium catalyst and a base and the product thus obtained is subsequently hydrogenated with hydrogen.Type: GrantFiled: February 2, 2001Date of Patent: November 13, 2001Assignee: Bayer AktiengesellschaftInventors: Henry Giera, Torsten Pohl, Uwe Hugger, Adolf Sicheneder, Fred Schuhmacher, Adolf Brill
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Publication number: 20010020115Abstract: Process for the production of an aromatic amine by reacting an aromatic hydrocarbon with ammonia at a temperature of less than 500° C. and a pressure of less than 10 bara in the presence of a catalyst comprising at least one metal selected from the group consisting of the transition elements, lanthanides and actinides, preferably in the presence of an oxidant.Type: ApplicationFiled: February 20, 2001Publication date: September 6, 2001Applicant: IMPERIAL CHEMICAL INDUSTRIES PLCInventors: Sean Alexander Axon, Samuel David Jackson, Peter Rene Rik Claes
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Patent number: 6235871Abstract: The transition metal-catalyzed amination of aryl halides, in conjunction with an orthogonal protective group scheme, forms the basis of two routes to oligoaniline precursors. The oligoaniline precursors are soluble in a variety of common organic solvents, and are easily converted to the deprotected oligoanilines. The method allows the preparation of oligoanilines of even or odd chain lengths, and the incorporation of a variety of functional groups into the oligomers. Polyanilines of low polydispersity can also be prepared by this method.Type: GrantFiled: December 2, 1998Date of Patent: May 22, 2001Assignee: Massachusetts Institute of TechnologyInventors: Robert A. Singer, Joseph P. Sadighi, Stephen L. Buchwald, Thomas Mackewitz
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Patent number: 6222073Abstract: Process for the preparation of an N-arylethylaniline of the formula (I) Ar—N(R1)2-n(CHR2CHR3Ar′)n (I) by reacting an aromatic olefin of the formula (II) Ar′CR3=CHR2 (II) with an aniline of the formula (III) Ar—N(R1)2-n(H)n (III) in an inert solvent in the presence of at least one basic catalyst selected from the group consisting of alkali metal alcoholates and alkaline earth metal alcoholates or alkali metal amides and alkaline earth metal amides, where, in the formulae (I) to (III), Ar and Ar′, independently of one another, are an aryl radical selected from the group consisting of the fused and nonfused C6-C22-aromatics and of the fused or nonfused C5-C22heteroaromatics which have at least one nitrogen, oxygen or sulfur atom in the ring; R1, R2 and R3, independently of one another, are a hydrogen atom, a C1-C8-alkyl radical or an aryl radical Ar; and n is the number 1 or 2.Type: GrantFiled: July 3, 2000Date of Patent: April 24, 2001Assignee: Aventis Research & Technologies GmbH & Co. KGInventors: Jürgen Herwig, Matthias Beller, Claudia Breindl, Harald Trauthwein, Elisabeth Eichberger, Anton Eichberger
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Patent number: 6166234Abstract: Novel tripodal cyclopentadiene derivatives have the formula (I) ##STR1## where E are identical or different and are --N(R)(R), --P(R)(R), --As(R)(R), --Sb(R)(R), --OR, --SR, --SeR, --TeR, where R are identical or different and are each hydrogen, a C.sub.1 -C.sub.20 -carboorganic radical or a C.sub.1 -C.sub.30 -organosilicon radical, or E is a leaving group X andR.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 are identical or different and are each hydrogen, a C.sub.1 -C.sub.20 -carboorganic radical or a C.sub.1 -C.sub.30 -organosilicon radical,Z is a cyclopentadienyl radical or a substituted cyclopentadienyl structural unit andT is hydrogen, a C.sub.1 -C.sub.20 -carboorganic radical or a C.sub.1 -C.sub.30 -organosilicon radical or a group E--Y--, where E is --N(R)(R), --P(R)(R), --As(R)(R), --Sb(R)(R), --OR, --SR, --SeR, --TeR or a leaving group X, where R are identical or different and are each hydrogen, a C.sub.1 -C.sub.20 -carboorganic radical or a C.sub.1 -C.sub.Type: GrantFiled: January 13, 1998Date of Patent: December 26, 2000Assignee: BASF AktiengesellschaftInventors: Gottfried Huttner, Joachim Vogelgesang, Ute Winterhalter, Bjorn Antelmann
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Patent number: 6143934Abstract: In a process for preparing amines of the general formula I ##STR1## where R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 are hydrogen, C.sub.1 -C.sub.20 -alkyl, C.sub.2 -C.sub.20 -alkenyl, C.sub.2 -C.sub.20 -alkynyl, C.sub.3 -C.sub.20 -cycloalkyl, C.sub.4 -C.sub.20 -alkylcycloalkyl, C.sub.4 -C.sub.20 -cycloalkylalkyl, aryl, C.sub.7 -C.sub.20 -alkylaryl or C.sub.7 -C.sub.20 -aralkyl,R.sup.1 and R.sup.2 are together a saturated or unsaturated, divalent C.sub.3 -C.sub.9 -alkylene chain andR.sup.3 and R.sup.5 are each C.sub.21 -C.sub.200 -alkyl, C.sub.21 -C.sub.200 -alkenyl or together are a divalent C.sub.2 -C.sub.12 -alkylene chain,by reacting olefins of the general formula II ##STR2## where R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are as defined above, with ammonia or primary or secondary amines of the general formula III ##STR3## where R.sup.1 and R.sup.2 are as defined above, at from 200 to 350.degree. C.Type: GrantFiled: January 20, 1998Date of Patent: November 7, 2000Assignee: BASF AktiengesellschaftInventors: Uwe Dingerdissen, Rudolf Kummer, Peter Stops, Ulrich Muller, Jurgen Herrmann, Karsten Eller