Preparing Directly By Amination Patents (Class 564/395)
  • Patent number: 11306262
    Abstract: 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: Grant
    Filed: June 11, 2019
    Date of Patent: April 19, 2022
    Assignee: INNER MONGOLIA YITAI COAL-BASED NEW MATERIALS RESEARCH INSTITUTE CO., LTD.
    Inventors: Zhen Qian, Jingwei Wu, Xiaolong Zhang, Jingquan Zhang, Juncheng Li, Qinge Jian
  • Patent number: 9440932
    Abstract: 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: Grant
    Filed: July 23, 2014
    Date of Patent: September 13, 2016
    Inventor: Bomi P Framroze
  • Patent number: 9006489
    Abstract: 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: Grant
    Filed: June 15, 2011
    Date of Patent: April 14, 2015
    Assignee: Jiangsu Sinorgchem Technology Co., Ltd.
    Inventor: Shiming Gao
  • Publication number: 20140371418
    Abstract: 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: Application
    Filed: January 4, 2013
    Publication date: December 18, 2014
    Applicant: pAromatics, LLC
    Inventors: Wing On Ng, Shingo Watanabe, Robert W.R. Humphreys, Steven C. Slater
  • Patent number: 8901354
    Abstract: 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: Grant
    Filed: December 28, 2012
    Date of Patent: December 2, 2014
    Assignee: Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences
    Inventors: Feng Shi, Xinjiang Cui, Hangkong Yuan, Youquan Deng
  • Patent number: 8766008
    Abstract: 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: Grant
    Filed: January 11, 2012
    Date of Patent: July 1, 2014
    Assignee: Bayer Cropscience AG
    Inventors: Norbert Lui, Rafael Warsitz, Christian Funke, Christian Severins
  • Patent number: 8614354
    Abstract: 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) treati
    Type: Grant
    Filed: June 18, 2008
    Date of Patent: December 24, 2013
    Assignee: Erregierre S.p.A.
    Inventors: Massimo Ferrari, Marcello Ghezzi, Matteo Bonaldi
  • Patent number: 8592631
    Abstract: 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: Grant
    Filed: January 28, 2011
    Date of Patent: November 26, 2013
    Assignee: The Procter & Gamble Company
    Inventors: John Michael Gardlik, Garry Steven Garrett, Bryan Patrick Murphy, John Michael Janusz, John August Wos
  • Patent number: 8399680
    Abstract: 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: Grant
    Filed: September 24, 2008
    Date of Patent: March 19, 2013
    Assignee: Centre National de la Recherche Scientifique (C.N.R.S.)
    Inventors: Marc Taillefer, Ning Xia
  • Publication number: 20130018204
    Abstract: 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: Application
    Filed: October 10, 2011
    Publication date: January 17, 2013
    Applicant: UNIST Academy-Industry Research Corporation
    Inventors: In Yup JEON, Jong Beom BAEK
  • Patent number: 8304550
    Abstract: 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: Grant
    Filed: November 21, 2008
    Date of Patent: November 6, 2012
    Assignee: Saltigo GmbH
    Inventors: Alain Cotte, Nikolaus Muller, Matthias Gotta, Matthias Beller, Thomas Schareina, Alexander Zapf
  • Publication number: 20110172463
    Abstract: 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: Application
    Filed: May 7, 2007
    Publication date: July 14, 2011
    Applicant: ALLIANT TECHSYSTEMS INC.
    Inventors: Stephen P. Velarde, Vincent E. Mancini
  • Publication number: 20100317894
    Abstract: 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: Application
    Filed: June 15, 2009
    Publication date: December 16, 2010
    Applicant: ALLIANT TECHSYSTEMS INC.
    Inventors: Nicholas A. Straessler, Stephen P. Velarde
  • Patent number: 7803953
    Abstract: 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: Grant
    Filed: June 1, 2007
    Date of Patent: September 28, 2010
    Assignee: Tosoh Corporation
    Inventors: Takanori Miyazaki, Masakazu Nishiyama, Naoki Matsumoto
  • Publication number: 20090143594
    Abstract: 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: Application
    Filed: November 21, 2008
    Publication date: June 4, 2009
    Applicant: SALTIGO GMBH
    Inventors: Alain Cotte, Nikolaus Muller, Matthias Gotta, Matthias Beller, Thomas Schareina, Alexander Zapf
  • Patent number: 7538251
    Abstract: 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: Grant
    Filed: February 1, 2005
    Date of Patent: May 26, 2009
    Assignee: ExxonMobil Research and Engineering Company
    Inventors: Michael Siskin, Alan Roy Katritzky, Kostyantyn Mykolayevich Kirichenko, Adeana Richelle Bishop, Christine Nicole Elia
  • Publication number: 20090124747
    Abstract: 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: Application
    Filed: October 14, 2008
    Publication date: May 14, 2009
    Applicant: William Marsh Rice University
    Inventor: Valery N. Khabashesku
  • Patent number: 7524990
    Abstract: 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: Grant
    Filed: February 1, 2005
    Date of Patent: April 28, 2009
    Assignee: ExxonMobil Research and Engineering Company
    Inventors: Michael Siskin, Alan Roy Katritzky, Kostyantyn Mykolayevich Kirichenko, Adeana Richelle Bishop, Christine Nicole Elia
  • Publication number: 20080183017
    Abstract: 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: Application
    Filed: January 25, 2007
    Publication date: July 31, 2008
    Applicant: Xerox Corporation
    Inventors: Timothy P. Bender, Emily L. Moore, Jennifer A. Coggan, Frank Ping-Hay Lee, David Borbely
  • Patent number: 7358399
    Abstract: 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: Grant
    Filed: October 6, 2005
    Date of Patent: April 15, 2008
    Assignee: Chemi SPA
    Inventors: Stefano Turchetta, Umberto Ciambecchini, Pietro Massardo
  • Publication number: 20080039633
    Abstract: 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: Application
    Filed: August 9, 2007
    Publication date: February 14, 2008
    Inventors: Joerg JUNG, Andreas Meudt, Bernd Wilheilm Lehnemann
  • Patent number: 7312331
    Abstract: 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: Grant
    Filed: June 7, 2006
    Date of Patent: December 25, 2007
    Assignee: The Regents of the University of California
    Inventors: Guy Bertrand, Vincent Lavallo, Yves Canac
  • Publication number: 20070282111
    Abstract: 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: Application
    Filed: June 1, 2007
    Publication date: December 6, 2007
    Applicant: TOSOH CORPORATION
    Inventors: Takanori Miyazaki, Masakazu Nishiyama, Naoki Matsumoto
  • Patent number: 7186864
    Abstract: 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: Grant
    Filed: May 28, 2003
    Date of Patent: March 6, 2007
    Assignee: Boehringer Ingelheim Pharmaceuticals, Inc.
    Inventors: Thomas Martin Kirrane, Jr., Daniel Kuzmich, John Robert Proudfoot, David Thomson
  • Patent number: 7053246
    Abstract: 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: Grant
    Filed: December 10, 2003
    Date of Patent: May 30, 2006
    Assignee: BASF Aktiengesellschaft
    Inventors: Till Gerlach, Frank Funke, Christoph Benisch, Johann-Peter Melder
  • Patent number: 7005449
    Abstract: 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: Grant
    Filed: April 23, 2002
    Date of Patent: February 28, 2006
    Assignee: Pharmacia & Upjohn Company
    Inventors: Michael Hawley, Satish Kumar Singh, Walter Morozowich, Mark P. Warchol
  • Patent number: 6933409
    Abstract: 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: Grant
    Filed: May 15, 2000
    Date of Patent: August 23, 2005
    Assignees: Symyx Technologies, Inc., Bayer AG
    Inventors: Damodara M. Poojary, Ramesh Borade, Alfred Hagemeyer, Xiao Ping Zhou, Christopher E. Dube, Ulrich Notheis, Ralph Armbrust, Christian Rasp, David M. Lowe
  • Patent number: 6822128
    Abstract: 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: Grant
    Filed: December 20, 2001
    Date of Patent: November 23, 2004
    Assignee: Corning Incorporated
    Inventors: Didier Letourneur, Charles M. Sorensen, Jr., Pierre Woehl
  • Publication number: 20040229958
    Abstract: A process is disclosed for manufacturing N-methyl-N-phenylaminoacrolein of formula (I) 1
    Type: Application
    Filed: May 7, 2004
    Publication date: November 18, 2004
    Applicant: Clariant Life Science Molecules (Italia) S.p.A.
    Inventors: Aldo Banfi, Alfredo Mancini
  • Publication number: 20040162444
    Abstract: 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: Application
    Filed: January 30, 2004
    Publication date: August 19, 2004
    Inventors: Russell E. Malz, Ranjit Kumar, Luis Javier Garces, Steven L. Suib
  • Publication number: 20040106807
    Abstract: Disclosed are methods of making aryl intermediate compounds of the formula (A) which are useful in the production of heteroaryl ureas, 1
    Type: Application
    Filed: November 17, 2003
    Publication date: June 3, 2004
    Applicant: Boehringer Ingelheim Pharmaceuticals, Inc.
    Inventors: Jinhua J. Song, Zhulin Tan, Nathan K. Yee
  • Publication number: 20040092772
    Abstract: 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: Application
    Filed: September 4, 2003
    Publication date: May 13, 2004
    Inventors: Carlo Perego, Alberto De Angelis, Otello Faris, Aldo Bosetti
  • Patent number: 6723880
    Abstract: 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: Grant
    Filed: June 19, 2002
    Date of Patent: April 20, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Neumann, Johann-Peter Melder, Christoph Benisch, Arthur Höhn, Joachim Pfeffinger
  • Publication number: 20030236437
    Abstract: 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: Application
    Filed: June 2, 2003
    Publication date: December 25, 2003
    Inventors: Leland A. Smeltz, Thomas C. Sedergran, Harold C. Jarrow
  • Patent number: 6646163
    Abstract: 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: Grant
    Filed: July 2, 2002
    Date of Patent: November 11, 2003
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Kenichi Nakamura, Kazuhiko Amakawa, Takuji Shitara
  • Publication number: 20030139627
    Abstract: 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: Application
    Filed: November 7, 2002
    Publication date: July 24, 2003
    Inventors: Tsutomu Katsuki, Yoshinori Kohmura
  • Publication number: 20030135052
    Abstract: 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: Application
    Filed: November 13, 2001
    Publication date: July 17, 2003
    Inventors: Kelley Moran Whittle, Alan Martin Allgeier, THOMAS PAPIN GANNETT, DAVID PAGE HIGLEY
  • Publication number: 20030130536
    Abstract: 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: Application
    Filed: August 27, 2002
    Publication date: July 10, 2003
    Inventor: Huw M. L. Davies
  • Publication number: 20020188158
    Abstract: 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: Application
    Filed: March 5, 2002
    Publication date: December 12, 2002
    Inventors: Wilfried Weiss, Dirk Dawidowski
  • Patent number: 6476269
    Abstract: 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: Grant
    Filed: September 17, 2001
    Date of Patent: November 5, 2002
    Assignee: Mitsubishi Gas Chemical Co. Inc.
    Inventors: Kenichi Nakamura, Susumu {overscore (O)}tsuka, Fumisada Kosuge, Takuji Shitara, Kazuhiko Amakawa
  • Patent number: 6387545
    Abstract: 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: Grant
    Filed: April 14, 1999
    Date of Patent: May 14, 2002
    Assignee: Industrial Technology Research Institute
    Inventors: Jia-Ming Liu, Huan-Lurn Hsieh, Po-Yen Lu, Ying-Chuan Wang
  • Publication number: 20020038054
    Abstract: 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: Application
    Filed: September 17, 2001
    Publication date: March 28, 2002
    Inventors: Kenichi Nakamura, Susumu Otsuka, Fumisada Kosuge, Takuji Shitara, Kazuhiko Amakawa
  • Publication number: 20020035295
    Abstract: 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: Application
    Filed: September 6, 2001
    Publication date: March 21, 2002
    Applicant: TAKASAGO INTERNATIONAL CORPORATION
    Inventors: Mitsuhiko Fujiwara, Ken Suzuki, Tohru Kobayashi, Yoji Hori, Toshimitsu Hagiwara
  • Publication number: 20020019551
    Abstract: 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: Application
    Filed: May 25, 2001
    Publication date: February 14, 2002
    Inventors: Adel Farhan Halasa, Wen-Liang Hsu
  • Patent number: 6316673
    Abstract: 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: Grant
    Filed: February 2, 2001
    Date of Patent: November 13, 2001
    Assignee: Bayer Aktiengesellschaft
    Inventors: Henry Giera, Torsten Pohl, Uwe Hugger, Adolf Sicheneder, Fred Schuhmacher, Adolf Brill
  • Publication number: 20010020115
    Abstract: 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: Application
    Filed: February 20, 2001
    Publication date: September 6, 2001
    Applicant: IMPERIAL CHEMICAL INDUSTRIES PLC
    Inventors: Sean Alexander Axon, Samuel David Jackson, Peter Rene Rik Claes
  • Patent number: 6235871
    Abstract: 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: Grant
    Filed: December 2, 1998
    Date of Patent: May 22, 2001
    Assignee: Massachusetts Institute of Technology
    Inventors: Robert A. Singer, Joseph P. Sadighi, Stephen L. Buchwald, Thomas Mackewitz
  • Patent number: 6222073
    Abstract: 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: Grant
    Filed: July 3, 2000
    Date of Patent: April 24, 2001
    Assignee: Aventis Research & Technologies GmbH & Co. KG
    Inventors: Jürgen Herwig, Matthias Beller, Claudia Breindl, Harald Trauthwein, Elisabeth Eichberger, Anton Eichberger
  • Patent number: 6166234
    Abstract: 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: Grant
    Filed: January 13, 1998
    Date of Patent: December 26, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Gottfried Huttner, Joachim Vogelgesang, Ute Winterhalter, Bjorn Antelmann
  • Patent number: 6143934
    Abstract: 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: Grant
    Filed: January 20, 1998
    Date of Patent: November 7, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Uwe Dingerdissen, Rudolf Kummer, Peter Stops, Ulrich Muller, Jurgen Herrmann, Karsten Eller