By Reductive Amination Patents (Class 564/397)
  • Patent number: 11028042
    Abstract: A process for preparing an aromatic polyamine mixture including 4,4?-methylenedi(phenylamine) and higher homologues of MDA is provided. The process includes steps of (i) reaction of aniline with formaldehyde by means of an acid catalyst to form a crude product mixture (I), (ii) neutralization of the crude product mixture (I) and removal of the salts formed; (iii) isolation of aniline; (iv) distillation of the resulting crude product mixture so as to separate off (iv-1) a mixture (II) of MDA isomers (II-1) containing from 8 to 20% by weight of 4,4?-methylenedi(phenylamine) and not more than 0.3% by weight of secondary components (II-2) and (iv-2) a low boiler mixture of at least 55% by weight of secondary components (II-2) and MDA isomers (II-1); and (v) recirculation of the mixture (II).
    Type: Grant
    Filed: January 12, 2017
    Date of Patent: June 8, 2021
    Inventors: Viktor Ladnak, Silvia Tauro, Kerstin Heinen, Kai Thiele, Klaus-Peter Metzner, Torsten Mattke
  • Patent number: 9029603
    Abstract: A process for preparing alkylated p-phenylenediamine having the steps of reacting aniline and nitrobenzene in presence of a complex base catalyst to obtain 4-aminodiphenylamine intermediates, hydrogenating the 4-aminodiphenylamine intermediates to 4-aminodiphenylamine in presence of a hydrogenation catalyst, and reductively alkylating the 4-aminodiphenylamine to alkylated p-phenylenediamine.
    Type: Grant
    Filed: September 14, 2012
    Date of Patent: May 12, 2015
    Assignee: Jiangsu Sinorgchem Technology Co., Ltd.
    Inventors: Xiaogen Feng, Nongyue Wang, Xiaohui Mao, Ruibiao Yu, Qianwen Cheng
  • Publication number: 20140073800
    Abstract: Embodiments of the invention are directed to ONO pincer ligands that can be in a trianionic, protonated or protonated equivalent form. The ONO pincer ligand can be combined with a transition metal comprising compound to form an ONO pincer ligand comprising transition metal complex. By choice of the ONO pincer ligand structure, the steric and electronic properties of the transition metal complexes therefrom can be controlled. The ONO pincer ligands comprise a central nitrogen atom that is disubstituted with a pair of three atom comprising bridges where the three atoms are three sp2 hybridized carbons or the three atoms are a pair of sp2 hybridized carbons and an sp3 hybridized carbon or silicon.
    Type: Application
    Filed: November 12, 2013
    Publication date: March 13, 2014
    Applicant: UNIVERSITY OF FLORIDA RESEARCH FOUNDATION, INC.
    Inventors: ADAM STEVEN VEIGE, MATTHEW O'REILLY, MUHAMMAD TARIQ JAN
  • 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: 8450530
    Abstract: The present invention relates to a process for preparing unsymmetric secondary tert-butylamines by continuous amination in the gas phase, wherein tert-butylamine is converted over hydrogenation catalysts in the presence of an alcohol or aldehyde and hydrogen.
    Type: Grant
    Filed: April 6, 2011
    Date of Patent: May 28, 2013
    Assignee: BASF SE
    Inventors: Christoph Mueller, Christof Wilhelm Wigbers, Johann-Peter Melder, Gerd Haderlein, Norbert Gutfrucht
  • Patent number: 8445726
    Abstract: The present application relates to a process for preparing unsymmetric secondary tert-butylamines which, as well as the tert-butyl radical, also comprise an alkyl, cycloalkyl or benzyl radical. They are prepared by reacting corresponding aldehydes with tert-butylamine and hydrogen in the presence of hydrogenation catalysts (reductive amination) in the liquid phase.
    Type: Grant
    Filed: April 5, 2011
    Date of Patent: May 21, 2013
    Assignee: BASF SE
    Inventors: Christof Wilhelm Wigbers, Christoph Mueller, Johann-Peter Melder, Bernd Stein, Harald Meissner, Gerd Haderlein, Norbert Gutfrucht
  • Patent number: 8350047
    Abstract: The present application relates to novel methods for the preparation of secondary carbinamine compounds, particularly the preparation of secondary carbinamine compounds of the formula Ia, formula Ib or formula IV from aldehydes of the formula II and boronic acids of the formula III or formula V, in the presence of ammonia or an ammonia equivalent of the formula NH4+X?.
    Type: Grant
    Filed: March 28, 2008
    Date of Patent: January 8, 2013
    Inventors: Avinash N. Thadani, Bhartesh Dhudshia
  • Publication number: 20120142969
    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: Application
    Filed: January 28, 2011
    Publication date: June 7, 2012
    Inventors: John Michael GARDLIK, Garry Steven Garrett, Bryan Patrick Murphy, John Michael Janusz, John August Wos
  • Publication number: 20110218360
    Abstract: The present invention relates to processes for the preparation of rasagiline mesylate. Also provided is rasagiline mesylate having 90 volume percent of the particles (D90) with sizes less than about 6 ?m and processes for the preparation thereof.
    Type: Application
    Filed: May 20, 2011
    Publication date: September 8, 2011
    Applicants: DR. REDDY'S LABORATORIES LTD., DR. REDDY'S LABORATORIES, INC.
    Inventors: Praveen Cherukupally, Venkata Reddy Vajrala, Vijaya Kumar Adla, Srinivasulu Rangineni, Sundaralakshmi Kanniah
  • Publication number: 20100298572
    Abstract: The present application relates to novel methods for the preparation of secondary carbinamine compounds, particularly the preparation of secondary carbinamine compounds of the formula Ia, formula Ib or formula IV from aldehydes of the formula II and boronic acids of the formula III or formula V, in the presence of ammonia or an ammonia equivalent of the formula NH4+X?.
    Type: Application
    Filed: March 28, 2008
    Publication date: November 25, 2010
    Applicant: PANASONIC CORPORATION
    Inventors: Avinash N. Thadani, Bhartesh Dhudshia
  • Patent number: 7754922
    Abstract: Processes comprising: (i) providing a reactant selected from the group consisting of primary alcohols, secondary alcohols, aldehydes, ketones and mixtures thereof; and (ii) reacting the reactant with hydrogen and a nitrogen compound selected from the group consisting of ammonia, primary amines, secondary amines and mixtures thereof, in the presence of a catalyst comprising a zirconium dioxide- and nickel-containing catalytically active composition, to form an amine; wherein the catalytically active composition, prior to reduction with hydrogen, comprises oxygen compounds of zirconium, copper, nickel and cobalt, and one or more oxygen compounds of molybdenum in an amount of 5.5 to 12% by weight, calculated as MoO3.
    Type: Grant
    Filed: July 4, 2007
    Date of Patent: July 13, 2010
    Assignee: BASF SE
    Inventors: Petr Kubanek, Bram Willem Hoffer, Ekkehard Schwab, Johann-Peter Melder, Holger Evers, Till Gerlach
  • Patent number: 7709679
    Abstract: The invention provides a process for the simultaneous preparation of 4,4?-diphenylmethanediamine and also diphenylmethane diisocyanate and polyphenylenepolymethylene polyisocyanates, which comprises the steps a) preparation of a mixture of diphenylmethanediamine and polyphenylenepolymethylenepolyamines by acid condensation of aniline and formaldehyde and subsequent work-up of the mixture, b) splitting-off of part of the mixture prepared in step a), c) distillation of the mixture separated off in step b) in a column, d) recirculation of the bottom product from step c) to the end product from step a) and condensation of the overhead product from step c), e) distillation of the overhead product from step c) in a column, f) recirculation of the overhead product from step e) to the end product from step a), g) isolation of the 4,4?-diphenylmethanediamine obtained as bottom product in step e), h) reaction of the mixture from step a) with phosgene and subsequent work-up of the reaction product.
    Type: Grant
    Filed: January 12, 2007
    Date of Patent: May 4, 2010
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Bock, Hans-Juergen Pallasch, Filip Deberdt, Johnny Moors
  • Patent number: 7473805
    Abstract: The process comprises reacting a compound of formula (II), where R is a hydroxyl protecting group, and the asterisk indicates an asymmetric carbon atom, with diisopropylamine in the presence of a reducing agent; optionally converting the resulting intermediate into a salt and, if so desired, isolating it; removing the hydroxyl protecting group; and if so desired, separating the desired (R) or (S) enantiomer, or the mixture of enantiomers and/or converting the obtained compound into a pharmaceutically acceptable salt thereof. Tolterodine is a muscarinic receptor antagonist useful in treating urinary incontinence and other symptoms of urinary bladder hyperactivity.
    Type: Grant
    Filed: December 21, 2004
    Date of Patent: January 6, 2009
    Assignee: Ragactives, S.L. Parque Tecnologico de Boecillo
    Inventors: Gustavo Pascual Coca, Pablo Martin Pascual, Jorge Martin Juarez
  • Patent number: 7361789
    Abstract: The present invention relates to novel dihydronaphthalene compounds, compositions, methods for using the same, and processes for preparing the same. The present invention also relates to novel total synthesis approaches for preparing these compounds. In addition, the present invention relates to methods of producing quantities of isomers of these compounds and separating and purifying them using chiral separation techniques. The present invention also relates to methods of producing quantities of a single isometric compound without the need for chiral separation techniques.
    Type: Grant
    Filed: July 27, 2005
    Date of Patent: April 22, 2008
    Assignee: Amgen Inc.
    Inventors: Qi Yan, Carlos Orihuela, Bo Shen, Ying Chen, Xin Wang, John Ng, Ruizhi Ji, Pengzu Zhou
  • Patent number: 7312362
    Abstract: The present invention relates to a process for the production of mixtures of di- and polyamines of the diphenylmethane series (MDA) containing less than 1,000 ppm of water and less than 200 ppm of aniline by reaction of aniline and formaldehyde in the presence of acid catalysts and subsequent separation of the acid catalyst and subsequent distillative separation of water and aniline in an at least a two-stage distillation including a flash evaporation and subsequent cooling.
    Type: Grant
    Filed: January 24, 2007
    Date of Patent: December 25, 2007
    Assignee: Bayer MaterialScience AG
    Inventors: Berthold Keggenhoff, Richard Adamson, Rudolf Uchdorf, Fritz Pohl
  • Publication number: 20070179317
    Abstract: The present invention relates to a process for the production of mixtures of di- and polyamines of the diphenylmethane series (MDA) containing less than 1,000 ppm of water and less than 200 ppm of aniline by reaction of aniline and formaldehyde in the presence of acid catalysts and subsequent separation of the acid catalyst and subsequent distillative separation of water and aniline in an at least a two-stage distillation including a flash evaporation and subsequent cooling.
    Type: Application
    Filed: January 24, 2007
    Publication date: August 2, 2007
    Inventors: Berthold Keggenhoff, Richard Adamson, Rudolph Uchdorf, Fritz Pohl
  • Publication number: 20070179316
    Abstract: The invention provides an improved process for preparing diamines and polyamines from the diphenylmethane series by reacting aniline and formaldehyde in the presence of an acid catalyst, the improvement involving the aniline containing less than about 3 wt. % of diamines and polyamines from the diphenylmethane series, based on the weight of the aniline.
    Type: Application
    Filed: January 24, 2007
    Publication date: August 2, 2007
    Inventors: Fritz Pohl, Jeffrey Bolton, Richard Adamson, Heinz-Herbert Muller, Rudolf Uchdorf
  • Patent number: 7230134
    Abstract: This application claims the benefit of German priority Application No. 10138140.9, filed on Aug. 9, 2001, and International Application No. PCT/EP02/08748, filed on Aug. 6, 2002. The invention relates to the production of amines by the reaction of aldehydes or ketones with ammonia or primary or secondary amines in the presence of a hydrogen-donor and the presence of homogeneous metal catalysts of the eighth sub-group under mild conditions.
    Type: Grant
    Filed: August 6, 2002
    Date of Patent: June 12, 2007
    Assignee: Degussa AG
    Inventors: Armin Borner, Uwe Dingerdissen, Renat Kadyrov, Thomas Riermeier, Vitali Tararov
  • Patent number: 7183438
    Abstract: Disclosed are catalysts, the catalytically active mass of which contains 22 to 40 percent by weight of oxygen-containing compounds of zirconium, calculated as ZrO2, 1 to 30 percent by weight of oxygen-containing compounds of copper, calculated as CuO, 15 to 50 percent by weight of oxygen-containing compounds of nickel, calculated as NiO, the molar ratio between nickel and copper being greater than 1, 15 to 50 percent by weight of oxygen-containing compounds of cobalt, calculated as CoO, and less than 1 percent by weight of an alkali metal, calculated as alkali metal oxide, prior to being treated with hydrogen. Also disclosed is a method for the production of amines by reacting primary and secondary alcohols, aldehydes, or ketones with hydrogen and nitrogen compounds selected from the group ammonia, primary and secondary amines, in the presence of said catalysts at an elevated temperature and an elevated pressure.
    Type: Grant
    Filed: March 7, 2003
    Date of Patent: February 27, 2007
    Assignee: BASF Aktiengesellschaft
    Inventors: Till Gerlach, Frank Funke, Johann-Peter Melder, Stefan Iselborn, Martin Rudloff, Michael Hüllmann
  • Patent number: 7176332
    Abstract: A method for the preparation of a compound of formula (VI): in which R2 is an optionally substituted C1–C6 alkyl; R4 is H, OH, an optionally substituted C1–C6 alkyl or an optionally substituted C1–C6 alkoxy; R5 is an optionally substituted aryl, an optionally substituted aralkyl, or an optionally substituted alkyl; and R6 is H or an optionally substituted C1–C6 alkyl; the method including the step of subjecting a ketone of formula (V) in which R2, R4 and R5 are as defined above, to reductive amination with an amine of formula R3NH2 in which R3 is an optionally substituted alkyl, and a reductant to form the compound of formula (VI), wherein the reaction is conducted in the presence of a supercritical fluid or a liquefied gas.
    Type: Grant
    Filed: August 26, 2002
    Date of Patent: February 13, 2007
    Assignees: Victoria University of Technology, Polychip Pharmaceuticals Pty. Ltd.
    Inventors: Andrew John Smallridge, Maurice Arthur Trewhella, Kylie Anne Wilkinson
  • Patent number: 7081551
    Abstract: Optically active (R)-1-(4-trifluoromethylphenyl)ethylamine is a novel compound as an important intermediate for medicines and agricultural chemicals. This compound can be obtained with high optical purity and high yield by a process including the steps of (a) a dehydrocondensation of 4?-(trifluoromethyl)acetophenone and an optically active (R)-1-phenylethylamine to obtain an optically active imine; (b) asymmetrically reducing the imine into an optically active secondary amine; (c) reacting the amine with an organic acid (phthalic acid or benzenesulfonic acid), thereby obtaining a product that is a phthalate of or benzenesulfonate of the amine; (d) subjecting the product of the step (c) to a hydrogenolysis, thereby obtaining a product that is a phthalate of or benzenesuilfonate of optically active (R)-1-(4-trifluoromethylphenyl)ethylamine; and (e) neutralizing the product of the step (d) into the optically active (R)-1-(4-trifluoromethylphenyl)ethylamine.
    Type: Grant
    Filed: May 21, 2003
    Date of Patent: July 25, 2006
    Assignee: Central Glass Co., Ltd.
    Inventors: Akihiro Ishii, Manabu Yasumoto, Yokusu Kuriyama, Masatomi Kanai, Kanjin Inomiya
  • Patent number: 7074962
    Abstract: This invention relates to apparatus particularly a monolith catalytic reactor in a stirred tank reactor. The stirred tank reactor including the fixed bed catalytic reactor apparatus comprises: an housing having an open top and open bottom portion supportably maintained with said tank, said housing having a substantially outwardly extending, horizontal baffle near its top portion said baffle having a least one perforation in its surface, and said housing having at least one perforation in the wall near its top portion; a fixed bed catalyst system supportably retained within said housing permitting both liquid and gas flow therethrough; and, an agitator shaft terminating in a turbine blade substantially adjacent the perforation in the wall of said housing, said agitator having a passageway including an opening in an upper portion thereof to the interior of an upper part of said tank and terminating in an opening adjacent the turbine blade.
    Type: Grant
    Filed: February 15, 2002
    Date of Patent: July 11, 2006
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Reinaldo Mario Machado, James Edward Koniski, Stephen Kohler
  • Patent number: 7034186
    Abstract: Process for preparing an amine by reacting a primary or secondary alcohol, aldehyde or ketone with hydrogen and a nitrogen compound selected from the group consisting of ammonia and primary and secondary amines in the presence of 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: April 25, 2006
    Assignee: BASF Aktiengesellschaft
    Inventors: Till Gerlach, Frank Funke, Johann-Peter Melder
  • Publication number: 20040249212
    Abstract: A method for the preparation of a compound of formula (VI): in which R2 is an optionally substituted C1-C6 alkyl; R4 is H, OH, an optionally substituted C1-C6 alkyl or an optionally substituted C1-C6 alkoxy; R5 is an optionally substituted aryl, an optionally substituted aralkyl, or an optionally substituted alkyl; and R5 is H or an optionally substituted C1-C6 alkyl; the method including the step of subjecting a ketone of formula (V) in which R2, R4 and R5 are as defined above, to reductive animation with an amine of formula R3NH2 in which R3 is an optionally substituted alkyl, and a reductant to form the compound of formula (VI), wherein the reaction is conducted in the presence of a supercritical fluid or a liquefied gas.
    Type: Application
    Filed: July 27, 2004
    Publication date: December 9, 2004
    Inventors: Andrew John Smallridge, Maurice Arthur Trewhella, Kylie Anne Wilkinson
  • Publication number: 20040249211
    Abstract: The present invention relates to a cost effective and industrially advantageous process for the preparation of tolterodine and pharmaceutically acceptable salts thereof.
    Type: Application
    Filed: May 18, 2004
    Publication date: December 9, 2004
    Inventors: Yatendra Kumar, Mohan Prasad, Praveen Kumar Neela, Satyananda Misra
  • Publication number: 20040225155
    Abstract: Process for preparing vanillylamine or one of the salts thereof by reacting vanillin with hydroxylamine or the salts thereof in the presence of an organic salt, which may optionally be produced in situ, wherein the reaction is carried out in an inorganic or organic acid as diluent, and subsequently hydrogenating the resulting vanillyloxime with hydrogen in the presence of a suitable catalyst and an organic and/or inorganic acid.
    Type: Application
    Filed: June 9, 2004
    Publication date: November 11, 2004
    Applicant: Boehringer Ingelheim Pharma KG
    Inventors: Oliver Meyer, Ingo Heddesheimer
  • Publication number: 20040053330
    Abstract: Synthetic methods provide for the simple, efficient preparation of amino polyols and derivatives. The methods include a three-component reaction of a carbohydrates with organoboron compounds and primary or secondary amine derivatives. The resulting amino polyols can be transformed into amino sugars. In one implementation, the amine moiety is protected, and an alkenyl, aryl or heteroaryl moiety is cleaved to form the amino sugar. Amino polyols and amino sugars prepared according to the methods are also described.
    Type: Application
    Filed: April 1, 2003
    Publication date: March 18, 2004
    Inventors: Nicos A. Petasis, Ilia A. Zavialov, Zubin D. Patel
  • Patent number: 6696609
    Abstract: A process for producing diamines which comprises the steps of: (1) reacting a dialdehyde with ammonia and hydrogen in the presence of an alcohol and a hydrogenation catalyst to synthesize the corresponding diamine; (2) separating and recovering the alcohol by distilling the reaction mixture obtained by the step (1); (3) separating the diamine by purifying the distillation residue obtained by the step (2); and (4) feeding at least part of the alcohol recovered in the step (2) to step (1); said step (1) comprising maintaining the amount of ammonia at a level of at least 200 moles per mole of the primary amine that has formed in the step (1) and accumulated in the reaction vessel for step (1). The process can produce diamines commercially advantageously and in high yields, the diamines having little impurities.
    Type: Grant
    Filed: March 4, 2003
    Date of Patent: February 24, 2004
    Assignee: Kuraray Co., Ltd.
    Inventors: Yoshihiro Tokuda, Shigeaki Suzuki
  • Patent number: 6696608
    Abstract: A catalytic transfer hydrogenation process is provided. The process can be employed to transfer hydrogenate N-substituted imines and iminium salts, which are preferably prochiral. The catalyst employed in the process is preferably a metal complex with one hydrocarbyl or cyclopentadienyl ligand and which is also coordinated to defined bidentate ligands. Preferred metals include rhodium, ruthenium and iridium. Preferred bidentate ligands are diamines and aminoalcohols, particularly those comprising chiral centres. The hydrogen donor is advantageously a mixture of triethylamine and formic acid. A process for the production of primary and secondary amines using the catalytic transfer hydrogenation of the N-substituted imines and iminium salts is also provided.
    Type: Grant
    Filed: February 14, 2002
    Date of Patent: February 24, 2004
    Assignee: Avecia Limited
    Inventors: Juliette Martin, Lynne Alison Campbell
  • Publication number: 20040029971
    Abstract: A process for preparing methane diphenyl diamine (MDA) or a mixture of methane diphenyl diamine (MDA) and its higher homologues with a controlled isomer distribution using a silanised zeolite have “shape selectivity”. The mixture contains compounds having the following general formula (I): where R represents a hydrogen atom or a C1 to C8 (iso) alkyl group, a C4 to C10 cycloalkyl group or a C6 to C12 aromatic group and n is a whole number greater than or equal to one so as to give a functionally of 2 to 6.
    Type: Application
    Filed: September 5, 2003
    Publication date: February 12, 2004
    Inventors: Alberto De Angelis, Cristina Flego, Otello Farias, Aldo Bosetti
  • Patent number: 6689913
    Abstract: Provided is a process for preparing terbinafine or its HCl salt comprising: reacting a furan derivative with a base to form a second compound; performing a reductive alkylation of the second compound obtained in the step with N-methyl-1-naphthalenemethylamine or its HCl salt to form a third compound; and purifying the third compound.
    Type: Grant
    Filed: December 27, 2002
    Date of Patent: February 10, 2004
    Assignee: Yuhan Corporation
    Inventors: Tai-Au Lee, Kyu-Jung Wang, Hong-Bae Kim, Kyoung-Chan Kwon, Chang-Hoe Ku
  • Patent number: 6689914
    Abstract: The preparation of amines of the formula (I): R1R2CH—N R3R4  (I) in which R1, R2, R3 and R4, independently of one another, are hydrogen, straight-chain or branched C1-C12-alkyl, C3-C12-cycloalkyl, C6-C10-aryl or C7-C11-aralkyl, takes place by catalytic, reductive amination of mixtures comprising carbonyl compounds of the formula (II) and/or alcohols of the formula (III) R1—C(═O)—R2  (II) R1—CH(OH)—R2  (III) which also comprise at least 50 ppm, based on the mixtures, of halogen, with nitrogen compounds of the formula (IV): H N R3 R4  (IV) with the abovementioned meanings for R1 to R4, in the presence of Co- and/or Ni-containing catalysts, which comprises carrying out the reductive amination additionally in the presence of solid acidic cocatalysts.
    Type: Grant
    Filed: September 5, 2002
    Date of Patent: February 10, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Martin Schäfer, Arnd Böttcher, Andreas Kramer, Arthur Höhn, Shelue Liang, Frank Funke
  • Publication number: 20040024253
    Abstract: Optically active (R)-1-(4-trifluoromethylphenyl)ethylamine is a novel compound as an important intermediate for medicines and agricultural chemicals. This compound can be obtained with high optical purity and high yield by a process including the steps of (a) a dehydrocondensation of 4′-(trifluoromethyl)acetophenone and an optically active (R)-1-phenylethylamine to obtain an optically active imine; (b) asymmetrically reducing the imine into an optically active secondary amine; (c) reacting the amine with an organic acid (phthalic acid or benzenesulfonic acid), thereby obtaining a product that is a phthalate of or benzenesulfonate of the amine; (d) subjecting the product of the step (c) to a hydrogenolysis, thereby obtaining a product that is a phthalate of or benzenesuilfonate of optically active (R)-1-(4-trifluoromethylphenyl)ethylamine; and (e) neutralizing the product of the step (d) into the optically active (R)-1-(4-trifluoromethylphenyl)ethylamine.
    Type: Application
    Filed: May 21, 2003
    Publication date: February 5, 2004
    Applicant: Central Glass Company, Limited
    Inventors: Akihiro Ishii, Manabu Yasumoto, Yokusu Kuriyama, Masatomi Kanai, Kanjin Inomiya
  • Patent number: 6642420
    Abstract: A process for the preparation of aldehydes and/or alcohols or amines by reacting olefins in the liquid phase with carbon monoxide and hydrogen, a part of these gases being dispersed in the form of gas bubbles in the reaction liquid and another part being dissolved in the reaction liquid, in the presence or absence of a primary or secondary amine and in the presence of a cobalt carbonyl, rhodium carbonyl, palladium carbonyl or ruthenium carbonyl complex dissolved homogeneously in the reaction liquid and having a phosphorus-, arsenic-, antimony- or nitrogen-containing ligand, at elevated temperatures and at 1 to 100 bar, wherein the reaction is carried out in a vertically arranged, tubular reactor comprising a reactor body and at least one circulation line, a part of the reaction liquid is fed continuously via the circulation line to at least one nozzle which is mounted in the upper part of the reactor body and is coordinated with a guide member, open at the top and bottom and bounded by parallel walls, in the
    Type: Grant
    Filed: February 7, 2001
    Date of Patent: November 4, 2003
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Zehner, Armin Ulonska, Rocco Paciello
  • Publication number: 20030187303
    Abstract: A process for producing diamines which comprises the steps of: (1) reacting a dialdehyde with ammonia and hydrogen in the presence of an alcohol and a hydrogenation catalyst to synthesize the corresponding diamine; (2) separating and recovering the alcohol by distilling the reaction mixture obtained by the step (1); (3) separating the diamine by purifying the distillation residue obtained by the step (2); and (4) feeding at least part of the alcohol recovered in the step (2) to step (1); said step (1) comprising maintaining the amount of ammonia at a level of at least 200 moles per mole of the primary amine that has formed in the step (1) and accumulated in the reaction vessel for step (1). The process can produce diamines commercially advantageously and in high yields, the diamines having little impurities.
    Type: Application
    Filed: March 4, 2003
    Publication date: October 2, 2003
    Applicant: Kuraray Co., Ltd.
    Inventors: Yoshihiro Tokuda, Shigeaki Suzuki
  • Patent number: 6583320
    Abstract: The invention is directed-to a method of producing one or more 4-aminodiphenylamine intermediates comprising the steps of bringing an aniline or aniline derivative and nitrobenzene into reactive contact and reacting the aniline and nitrobenzene in a confined zone at a suitable time and temperature, in the presence of a mixture comprising an inorganic salt or metal organic salt having a cation that would be a suitable cation of a strong inorganic base, an oxidant and an organic base, the mixture not including a reaction product of betaine and a strong inorganic base.
    Type: Grant
    Filed: May 10, 2002
    Date of Patent: June 24, 2003
    Assignee: Flexsys America L.P.
    Inventors: Ralph Dale Triplett, II, Roger Keranen Rains
  • Patent number: 6525222
    Abstract: Amines are prepared by reacting aldehydes or ketones at elevated temperature under elevated pressure with nitrogen compounds selected from the group of ammonia, primary and secondary amines, and with hydrogen in the presence of a catalyst, wherein the catalytically active mass of the catalyst contains, after its preparation and before the treatment with hydrogen, 22 to 45% by weight of oxygen-containing compounds of zirconium, calculated as ZrO2, 1 to 30% by weight of oxygen-containing compounds of copper, calculated as CuO, 5 to 50% by weight of oxygen-containing compounds of nickel, calculated as NiO, where the molar ratio of nickel to copper is greater than 1, 5 to 50% by weight of oxygen-containing compounds of cobalt, calculated as CoO, 0 to 5% by weight of oxygen-containing compounds of molybdenum, calculated as MoO3, and 0 to 10% by weight of oxygen-containing compounds of aluminum and/or manganese, calculated as Al2O3 or MnO2.
    Type: Grant
    Filed: December 5, 2000
    Date of Patent: February 25, 2003
    Assignee: BASF Aktiengesellschaft
    Inventors: Jan Nouwen, Arthur Höhn, Horst Neuhauser, Frank Funke, Stephan Andreas Schunk, Johann-Peter Melder, Knut Eger, Michael Hesse, Joachim Wulff-Döring
  • Patent number: 6479704
    Abstract: The present invention relates to an improved for the hydrogenation of an immiscible mixture of an organic reactant in water. The immiscible mixture can result from the generation of water by the hydrogenation reaction itself or, by the addition of, water to the reactant prior to contact with the catalyst. The improvement resides in effecting the hydrogenation reaction in a monolith catalytic reactor from 100 to 800 cpi, at a superficial velocity of from 0.1 to 2 m/second in the absence of a cosolvent for the immiscible mixture. In a preferred embodiment, the hydrogenation is carried out using a monolith support which has a polymer network/carbon coating onto which a transition metal is deposited.
    Type: Grant
    Filed: April 20, 2001
    Date of Patent: November 12, 2002
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Andrew Francis Nordquist, Frederick Carl Wilhelm, Francis Joseph Waller, Reinaldo Mario Machado
  • Patent number: 6462236
    Abstract: Amines of the formula (I) R1R2CH—NR3R4  (I) where R1, R2, R3 and R4 are each, independently of one another, hydrogen, straight-chain or branched C1-C12-alkyl, C3-C12-cycloalkyl, C6-C10-aryl or C7-C11-aralkyl, where at least one of the radicals R1 and R2 is aryl or aralkyl whose aromatic unit is substituted by at least one halogen, are prepared by catalytic, hydrogenative amination of carbonyl compounds of the formula (II) or alcohols of the formula (III) R1—C(═O)—R2  (II) R1—CH(OH)—R2  (III) by means of nitrogen compounds of the formula (IV) HNR3R4  (IV) where R1 to R4 are as defined above, in the presence of Co- and/or Ni-containing catalysts, in the additional presence of solid acid cocatalysts and in the absence of organic sulfur compounds.
    Type: Grant
    Filed: October 24, 2001
    Date of Patent: October 8, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Shelue Liang, Frank Funke, Arthur Höhn
  • Patent number: 6429335
    Abstract: The present invention relates to a process for preparing amines of formula (I) R1—CH2—NH2  (I), wherein R1 represents optionally branched C1-C12-alkyl, C3-C8-cycloalkyl, C6-C12-aryl or C6-C12-aryl substituted with halogen-and/or C1-C12-alkyl, C7-C10-aralkyl or C7-C10-aralkyl substituted on the aryl radical by halogen and/or C1-C12-alkyl, or an aldose residue of the formula CiH2i+1Oi in which i is 2 to 5 and wherein one hydrogen of the aldose residue is optionally replaced by a saccharide residue, by catalytically hydrogenating aldehydes of formula (II) R1—CHO  (II), wherein R1 has the meaning indicated for formula (I), in the presence of ammonia, a hydrogenation catalyst, and disodium tetraborate.
    Type: Grant
    Filed: December 12, 2001
    Date of Patent: August 6, 2002
    Assignee: Bayer Aktiengesellschaft
    Inventor: Wolfgang Kiel
  • Patent number: 6417353
    Abstract: Amines are prepared by reacting aldehydes or ketones at elevated temperature under elevated pressure with nitrogen compounds selected from the group of ammonia, primary and secondary amines, and with hydrogen in the presence of a catalyst containing copper, wherein the catalytically active mass of the catalyst contains, before the reduction with hydrogen, 20 to 85% by weight of oxygen-containing compounds of zirconium, calculated as ZrO2, 1 to 30% by weight of oxygen-containing compounds of copper, calculated as CuO, 14 to 70% by weight of oxygen-containing compounds of nickel, calculated as NiO, 0 to 5% by weight of oxygen-containing compounds of molybdenum, calculated as MoO3, and 0 to 10% by weight of oxygen-containing compounds of aluminum, calculated as Al2O3.
    Type: Grant
    Filed: March 7, 2000
    Date of Patent: July 9, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Frank Funke, Joachim Wulff-Döring, Gerhard Schulz, Wolfgang Siegel, Andreas Kramer, Johann-Peter Melder, Arthur Höhn, Philipp Buskens, Wolfgang Reif, Jan Nouwen
  • Publication number: 20020082455
    Abstract: Amines of the formula (I)
    Type: Application
    Filed: October 24, 2001
    Publication date: June 27, 2002
    Inventors: Shelue Liang, Frank Funke, Arthur Hohn
  • Publication number: 20020077505
    Abstract: A method for preparation of an amine from a carbonium ion precursor and a nitrile. The method comprises the steps of: (a) contacting the carbonium ion precursor and the nitrile with aqueous ammonium hydrogen sulfate to produce an amide; and (b) hydrolyzing the amide to the amine. Optionally, the ammonium hydrogen sulfate, nitrile and ammonia are recovered and recycled.
    Type: Application
    Filed: November 14, 2001
    Publication date: June 20, 2002
    Inventor: Newman Mayer Bortnick
  • Patent number: 6395933
    Abstract: The invention is directed to a method of producing one or more 4-aminodiphenylamine intermediates comprising the steps of bringing an aniline or aniline derivative and nitrobenzene into reactive contact; and reacting the aniline and nitrobenzene in a confined zone at a suitable time and temperature, in the presence of a mixture comprising a strong base and a suitable phase transfer catalyst. Certain phase transfer catalysts may also function as the strong base.
    Type: Grant
    Filed: July 23, 2001
    Date of Patent: May 28, 2002
    Assignee: Flexsys America, L.P.
    Inventors: Ralph Dale Triplett, II, Roger Keranen Rains
  • Patent number: 6342079
    Abstract: 1-(2,5-Diaminophenyl)ethanol useful as a primary intermediate for the oxidative dyeing of hair.
    Type: Grant
    Filed: January 27, 2000
    Date of Patent: January 29, 2002
    Assignee: Bristol-Myers Squibb Company
    Inventors: Yuh-Guo Pan, Mu-Ill Lim, Linas R. Stasaitis
  • Patent number: 6331649
    Abstract: The present invention relates to a process for producing a trifluoromethylbenzylamine represented by the general formula (1). This process includes the step of reducing an oxime represented by the general formula (2), where R1 represents hydrogen atom, a halogen atom selected from the group consisting of fluorine, chlorine, bromine and iodine, or trifluoromethyl group, where R1 is defined as above, and R2 represents hydrogen atom, an alkyl group or an aralkyl group. With this process, the trifluoromethylbenzylamine can be produced with high selectivity.
    Type: Grant
    Filed: March 21, 2000
    Date of Patent: December 18, 2001
    Assignee: Central Glass Company, Limited
    Inventors: Satoru Narizuka, Yutaka Katsuhara
  • Patent number: 6320084
    Abstract: The invention pertains to a process for the preparation of glyceraldehyde, or an acetal or a hemiacetal thereof, characterized in that 3-butene-1,2-diol is dissolved in a lower alkanol and is subjected to ozonolysis to obtain a 3-hydroperoxy-3-alkoxy-propane-1,2-diol, which is subjected to a reductive treatment to obtain a hemiacetal of glyceraldehyde, which optionally may be converted into glyceraldehyde or an acetal or hemiacetal thereof, and to a process wherein the hemiacetal of glyceraldehyde is converted to a 3-aminopropane-1,2-diol derivative, by subjecting the hemiacetal of glyceraldehyde to a reductive treatment in the presence of ammonia or a primary or secondary amine.
    Type: Grant
    Filed: February 26, 2001
    Date of Patent: November 20, 2001
    Assignee: Akzo Nobel NV
    Inventors: Ulrich Wecker, Manfred Josef Bergfeld
  • Publication number: 20010003136
    Abstract: Amines are prepared by reacting aldehydes or ketones at elevated temperature under elevated pressure with nitrogen compounds selected from the group of ammonia, primary and secondary amines, and with hydrogen in the presence of a catalyst, wherein the catalytically active mass of the catalyst contains, after its preparation and before the treatment with hydrogen, 22 to 45% by weight of oxygen-containing compounds of zirconium, calculated as ZrO2,
    Type: Application
    Filed: December 5, 2000
    Publication date: June 7, 2001
    Inventors: Jan Nouwen, Arthur Hohn, Horst Neuhauser, Frank Funke, Stephan Andreas Schunk, Johann-Peter Melder, Knut Eger, Michael Hesse, Joachim Wulff-Doring
  • Patent number: 6232501
    Abstract: This invention relates to a process for the cis-selective preparation of cyclic amines of the sertraline type by reductive alkylation of cyclic immines or of their precursors and for the catalytic hydrogenation in the presence of copper-containing catalysts.
    Type: Grant
    Filed: September 14, 2000
    Date of Patent: May 15, 2001
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Heinz Steiner, Markus Benz, Hans-Peter Jalett, Marc Thommen
  • Patent number: 6194615
    Abstract: The present invention relates to the composition, process of preparation, and use of novel derivatives prepared from 1,5-bis-(4′-carbomethoxyphenyl)-1,4-pentadien-3-one. These novel compositions can act as crosslinkers with polyfunctional monomeric, oligomeric, and/or polymeric anhydrides, esters, carboxylic acids, isocyantes, epoxies, carbonates, acetoacetates, and alkoxylated melamines.
    Type: Grant
    Filed: June 17, 1999
    Date of Patent: February 27, 2001
    Assignee: Eastman Chemical Company
    Inventors: Philip Conrad Heidt, Matthew Lynn Elliott