By Reductive Amination Patents (Class 564/472)
  • Patent number: 10899726
    Abstract: A process for the production of aromatic primary amines, by reacting an aromatic dialdehyde with hydrogen and ammonia or an ammonia-liberating compound, in the presence of a hydrogenation catalyst and an amine, wherein the molar ratio of the amine to the aromatic dialdehyde is no less than 1:4 at the start of the reaction.
    Type: Grant
    Filed: July 8, 2015
    Date of Patent: January 26, 2021
    Assignee: RHODIA OPERATIONS
    Inventors: Peng Li, Floryan Decampo
  • Patent number: 8916728
    Abstract: The present invention relates to a process for preparing alkylalkanolamines, comprising the reaction of a carbonyl-based compound with a hydroxylalkylamine, in the presence of hydrogen and a catalyst.
    Type: Grant
    Filed: June 25, 2010
    Date of Patent: December 23, 2014
    Assignee: Arkema France
    Inventors: Christophe Ruppin, François Guillemet
  • Publication number: 20140275475
    Abstract: A process for preparing olefin-CO copolymers with the steps of: providing a reactor; charging the reactor with a gaseous olefin and with CO, such that there is a first pressure p1 in the reactor; and reacting olefin with CO in the presence of a catalyst in the reactor. Prior to the reaction, either no CO is present in the reactor or the volume ratio of gaseous olefin to CO is ?90:10. During the reaction, gaseous olefin and CO are metered in at least intermittently, with an average over time of the volume ratio of the olefin metered into CO metered in of ?90:10.
    Type: Application
    Filed: March 11, 2014
    Publication date: September 18, 2014
    Applicant: Bayer Intellectual Property GmbH
    Inventors: Thomas Ernst Müller, Christoph Gürtler, Walter Leitner, Henning Vogt, Saeeda Soomro
  • Publication number: 20140275371
    Abstract: The present invention relates to a process for preparing olefin-CO terpolymers with the steps of: providing a reactor; charging the reactor with a first, gaseous olefin and with CO, such that there is a first pressure p1 in the reactor; reacting the first olefin with CO in the presence of a catalyst in the reactor; wherein a second olefin is initially charged in the reactor and/or metered in during the reaction, prior to the reaction either no CO is present in the reactor or the volume ratio of first, gaseous olefin to CO is >60:40, and during the reaction the average over time of the volume ratio of gaseous olefin metered in to CO metered in is >60:40.
    Type: Application
    Filed: March 11, 2014
    Publication date: September 18, 2014
    Applicant: Bayer Intellectual Property GmbH
    Inventors: Thomas Ernst Müller, Christoph Gürtler, Walter Leitner, Henning Vogt, Saeeda Soomro
  • Patent number: 8653306
    Abstract: An improved method for the production of 2-amino-1,3-propanediol (serinol) and its bis-adduct, 2,2?-iminobis-1,3-propanediol, from dihydroxyacetone and ammonia in the presence of a hydrogenation catalyst such as Raney nickel, followed by separation using an acidic ion-exchange resin.
    Type: Grant
    Filed: December 21, 2012
    Date of Patent: February 18, 2014
    Assignee: Penn A Kem LLC
    Inventors: Shridhar G. Hegde, Lei Zhao
  • Publication number: 20130310560
    Abstract: Processes for preparing an amine are described which comprise reacting a primary or secondary alcohol, aldehyde and/or ketone with hydrogen and a nitrogen compound selected from the group of ammonia, primary and secondary amines, in the presence of a zirconium dioxide-, copper- and nickel-containing catalyst. The catalytically active composition of the catalyst, before its reduction with hydrogen, comprises oxygen compounds of zirconium, of copper, of nickel, in the range from 1.0 to 5.0% by weight of oxygen compounds of cobalt, calculated as CoO, and in the range from 0.2 to 5.0% by weight of oxygen compounds of sulfur, of phosphorus, of gallium, of lead and/or of antimony, calculated in each case as H2SO4, H3PO4, Ga203, PbO and Sb203 respectively.
    Type: Application
    Filed: November 8, 2012
    Publication date: November 21, 2013
    Applicant: BASF SE
    Inventors: PETR KUBANEK, WOLFGANG MÄRGELEIN, EKKEHARD SCHWAB, JOHANN-PETER MELDER, MANFRED JULIUS
  • Patent number: 8211949
    Abstract: Novel mixtures of long-chain (C10-C20) olefins are functionalized by conversion to aldehydes using an OXO process, or to sulfates, sulfonates, sulfones, sulfides, or sulfoxides by direct sulfonation. The aldehydes may then be hydrogenated to form alcohols, or aminated to form amines or amides. The olefins starting mixture may be acquired as a byproduct of the tetramerization of ethylene in the presence of certain chromium-containing tetramerization catalysts. The functionalized mixtures, and derivatives prepared therefrom such as alkoxylates prepared from the alcohols, may be useful as surfactants that may offer improved performance in many applications, while their preparation based on a byproduct mixture reduces their cost and also reduces waste-handling issues for this non-targeted stream.
    Type: Grant
    Filed: September 16, 2008
    Date of Patent: July 3, 2012
    Assignee: Dow Global Technologies LLC
    Inventors: Pierre T. Varineau, Brian W. Kolthammer, Aaron W. Sanders, David A. Wilson, Kara S. Weber, Robert Kirk Thompson, Cynthia L. Rand, Thomas C. Eisenschmid
  • Publication number: 20120116126
    Abstract: The present invention relates to a process for preparing alkylalkanolamines, comprising the reaction of a carbonyl-based compound with a hydroxylalkylamine, in the presence of hydrogen and a catalyst.
    Type: Application
    Filed: June 25, 2010
    Publication date: May 10, 2012
    Inventors: Christophe Ruppin, Francois Guillemet
  • Patent number: 8093431
    Abstract: A novel method for producing amine-aldehyde sulfur scavenging compositions are disclosed, where the method comprises contacting an amine containing component and a aldehyde containing component in the presence of an alcohol at an amine to aldehyde ratio of between about 0.8 and 0.45 for a reaction time and at a reaction temperatures sufficient to produce an amine-aldehyde adduct product having a specific gravity between about 3% and 7% less than the specific gravity of a mixture of starting materials.
    Type: Grant
    Filed: February 2, 2009
    Date of Patent: January 10, 2012
    Assignee: Clearwater International LLC
    Inventors: Olusegun Matthew Falana, Ray Veldman, Frank Zamora, Emilia U. Ugwu, Zoraida Vazquez
  • Patent number: 8034978
    Abstract: Process for preparing an amine by reacting an aldehyde and/or ketone with hydrogen and a nitrogen compound selected from the group consisting of primary and secondary amines in the presence of a heterogeneous catalyst, wherein the reaction is carried out using a suspended catalyst as heterogeneous catalyst and is carried out in the semibatch mode in which the nitrogen compound as one reactant is placed in the reaction vessel and the aldehyde and/or the ketone as the other reactant is added during the course of the reaction and the aldehyde and/or the ketone is added in portions or continuously to the reaction mixture during the course of the reaction as a function of the achieved conversion of the nitrogen compound until a conversion of the nitrogen compound of at least 95% results, and all or part of the catalyst remains in the reaction vessel after the reaction batch and is reused for the next reaction batch.
    Type: Grant
    Filed: May 24, 2007
    Date of Patent: October 11, 2011
    Assignee: BASF SE
    Inventors: Jan Eberhardt, Harald Meiβner, Bram Willem Hoffer, Johann-Peter Melder, Ekkehard Schwab
  • Patent number: 8012913
    Abstract: A new class of sulfur scavenging or converting compositions is disclosed comprising diamine terminated, amine-aldehyde adducts, where the adducts are substantially bimolecular amine-aldehyde adducts and the composition is substantially free of trimer and/or triazines. Methods for making and using the new class of sulfur scavenging or converting composition are also disclosed.
    Type: Grant
    Filed: October 10, 2006
    Date of Patent: September 6, 2011
    Assignee: Clearwater International LLC
    Inventors: Larry W. Gatlin, Daniel R. Dostie, Timothy Eric Gatlin
  • Patent number: 7985882
    Abstract: A modified solid-support for use as a supported reagent for use in reduction reactions, including reductive amination comprising a solid-support having an tetrasubstituted ammonium cation species ionically bonded to a borohydride anion species extending therefrom having the general formula: wherein P is a solid-support, S is a spacer group selected from the group consisting of alkylene, {including —(CH2)n—}, alkyleneoxy {including -0(CH2)n—}, alkylenethio {including —S(CH2)n—} and alkylenecarboxy, {including —O(O)C—(CH2)n—}, n=2-16. R1, R2, R3 and R are each independently selected from the group consisting of alkyl, cycloalkyl, haloalkyl and aryl. Y equals 1, 2 or 3. H is hydrogen or deuterium.
    Type: Grant
    Filed: August 23, 2002
    Date of Patent: July 26, 2011
    Assignee: Biotage AB
    Inventors: Sukanta Bhattacharyya, Jeffrey W. Labadie, Owen W. Gooding, Sunil Rana
  • Publication number: 20110137030
    Abstract: A process for preparing an amine by reacting a primary or secondary alcohol, aldehyde and/or ketone with hydrogen and a nitrogen compound selected from the group of ammonia and primary and secondary amines, in the presence of a supported copper-, nickel- and cobalt-containing catalyst, wherein the catalytically active material of the catalyst, before the reduction thereof with hydrogen, comprises oxygen compounds of aluminum, of copper, of nickel and of cobalt, and in the range from 0.2 to 5.0% by weight of oxygen compounds of tin, calculated as SnO, and catalysts as defined above.
    Type: Application
    Filed: December 2, 2010
    Publication date: June 9, 2011
    Applicant: BASF SE
    Inventors: Petr Kubanek, Wolfgang Mägerlein, Johann-Peter Melder, Thomas Heidemann
  • Publication number: 20100274011
    Abstract: Processes for preparing an amine, the processes comprising: reacting a reactant selected from the group consisting of primary alcohols, secondary alcohols, aldehydes, ketones, and mixtures thereof, 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 zirconium dioxide-, copper- and nickel-containing catalyst; wherein the catalyst comprises a catalytically active composition which comprises, before reduction with hydrogen, oxygen compounds of zirconium, copper, and nickel, 1.5 to 4.5% by weight of an oxygen compound of cobalt, calculated as CoO, and 0.2 to 5.0% by weight of at least one oxygen compound of niobium, sulfur, phosphorus, gallium, boron, lead or antimony, calculated in each case as Nb2O5, H2SO4, H3PO4, Ga2O3, B2O3, PbO and Sb2O3 respectively, and wherein the catalytically active composition does not comprise any molybdenum.
    Type: Application
    Filed: December 10, 2008
    Publication date: October 28, 2010
    Applicant: BASF SE
    Inventors: Petr Kubanek, Wolfgang Mägerlein, Ekkehard Schwab, Johann-Peter Melder, Manfred Julius
  • 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
  • Publication number: 20090312579
    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, and nickel, and one or more oxygen compounds of silver in an amount of 0.5 to 6% by weight, calculated as AgO.
    Type: Application
    Filed: July 4, 2007
    Publication date: December 17, 2009
    Applicant: BASF SE
    Inventors: Petr Kubanek, Bram Willem Hoffer, Ekkehard Schwab, Johann-Peter Melder
  • Patent number: 7619118
    Abstract: Processes for the conversion of glycerol to a product mixture of an amino alcohol product and propylene glycol are disclosed. Glycerol is converted to hydroxyacetone and the hydroxyacetone is reduced with a reducing agent or reacted with an amine compound to give an adduct which is reduced using the reducing agent to obtain a product mixture of propylene glycol and an amino alcohol product.
    Type: Grant
    Filed: June 7, 2007
    Date of Patent: November 17, 2009
    Assignee: The Procter & Gamble Company
    Inventors: Victor Manuel Arredondo, Patrick Joseph Corrigan
  • Patent number: 7619119
    Abstract: Processes for converting glycerol to an amino alcohol product involving reacting glycerol with a metal catalyst to obtain hydroxyacetone, and reacting the hydroxyacetone with an amine compound to obtain an adduct that is then reduced using a reducing agent to obtain an amino alcohol product are described.
    Type: Grant
    Filed: June 7, 2007
    Date of Patent: November 17, 2009
    Assignee: The Procter & Gamble Company
    Inventors: Victor Manuel Arredondo, Patrick Joseph Corrigan, Angella Christine Cearley, Deborah Jean Back, Michael Steven Gibson, Neil Thomas Fairweather
  • Publication number: 20090275781
    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: Application
    Filed: July 4, 2007
    Publication date: November 5, 2009
    Applicant: BASF SE
    Inventors: Petr Kubanek, Bram Willem Hoffer, Ekkehard Schwab, Johann-Peter Melder, Holger Evers, Till Gerlach
  • Patent number: 7405327
    Abstract: Process for the continuous preparation of an amine by reaction of a primary or secondary alcohol, aldehyde and/or ketone with hydrogen and a nitrogen compound selected from the group consisting of ammonia, primary and secondary amines at a temperature in the range from 60 to 300° C.
    Type: Grant
    Filed: May 4, 2005
    Date of Patent: July 29, 2008
    Assignee: BASF Aktiengesellschaft
    Inventors: Frank Haese, Arnd Bottcher, Bernd Stein, Wolfgang Reif, Johann-Peter Melder, Karl-Heinz Roβ, Heinz Rutter, Shelue Liang, Stefan Rittinger
  • 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: 7122702
    Abstract: Process for the catalytic hydrogenation of an aliphatically unsaturated group in an organic compound 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: October 17, 2006
    Assignee: BASF Aktiengesellschaft
    Inventors: Till Gerlach, Frank Funke, Johann-Peter Melder
  • Patent number: 7074963
    Abstract: Disclosed herein is a process for the reductive alkylation of primary amines to form secondary amines, by high pressure reaction of the primary amine with an alkylating agent and hydrogen in the presence of a catalyst which comprises metallic palladium. A process of the present invention is characterized in having high conversion rates and high selectivities, both greater than 95% on a first pass through the reactor. According to a preferred embodiment, the secondary amine produced comprises at least one 2-alkyl group bonded to the nitrogen atom of the primary amine product.
    Type: Grant
    Filed: July 18, 2003
    Date of Patent: July 11, 2006
    Assignee: Huntsman Petrochemical Corporation
    Inventors: Wei-Yang Su, Christopher H. Nelli
  • 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
  • Patent number: 7001708
    Abstract: Image formation via photoinduced fluorescence changes in a polymeric medium with two-photon fluorescence readout of a multi-layer structure. Fluorophore-containing polymers, possessing one or more basic functional groups, underwent protonation in the presence of a photoinduced acid generator upon exposure to a broad-band UV light source or fast-pulsed red to near-IR laser irradiation. Solution studies demonstrated formation of monoprotonated and diprotonated species upon irradiation, each resulting in distinctly different absorption and fluorescence properties. The fluorescence of the original, neutral, fluorophore was reduced upon monoprotonation, leading to a concomitant increase in fluorescence at longer wavelengths due to the monoprotonated form, the basis for multichannel data readout.
    Type: Grant
    Filed: November 27, 2002
    Date of Patent: February 21, 2006
    Assignee: University of Central Florida Research Foundation, Inc.
    Inventor: Kevin D. Belfield
  • Patent number: 6982352
    Abstract: The present invention relates to a process for preparing N-methyldialkyl-amines by reacting secondary dialkylamines with formaldehyde at a temperature of from 100 to 200° C., by using from 1.5 to 3 mol of formaldehyde per mole of secondary dialkylamine and degassing the resulting reaction product, removing the aqueous phase and distilling the organic phase.
    Type: Grant
    Filed: March 19, 2004
    Date of Patent: January 3, 2006
    Assignee: Celanese Chemicals Europe GmbH
    Inventors: Peter Lappe, Helmut Springer
  • Publication number: 20040267051
    Abstract: 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: Application
    Filed: August 18, 2004
    Publication date: December 30, 2004
    Inventors: Amin Boerner, Uwe Dingerdissen, Renat Kaxyrov, Thomas Riermeier, Vitali Tararov
  • Publication number: 20040225133
    Abstract: The invention relates to processes for converting amino acids and amides to desirable conversion products including pyrrolidines, pyrrolidinones, and other N-substituted products. L-glutamic acid and L-pyroglutamic acid provide general reaction pathways to numerous and valuable selective conversion products with varied potential industrial uses.
    Type: Application
    Filed: May 6, 2004
    Publication date: November 11, 2004
    Applicant: Battelle Memorial Institute
    Inventor: Johnathan E. Holladay
  • Publication number: 20040122259
    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: Application
    Filed: December 10, 2003
    Publication date: June 24, 2004
    Inventors: Till Gerlach, Frank Funke, Johann-Peter Melder
  • 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
  • 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: 20040019238
    Abstract: Disclosed herein is a process for the reductive alkylation of primary amines to form secondary amines, by high pressure reaction of the primary amine with an alkylating agent and hydrogen in the presence of a catalyst which comprises metallic palladium. A process of the present invention is characterized in having high conversion rates and high selectivities, both greater than 95% on a first pass through the reactor. According to a preferred embodiment, the secondary amine produced comprises at least one 2-alkyl group bonded to the nitrogen atom of the primary amine product.
    Type: Application
    Filed: July 18, 2003
    Publication date: January 29, 2004
    Applicant: Huntsman Petrochemical Corporation
    Inventors: Wei-Yang Su, Christopher H. Nelli
  • Publication number: 20040015016
    Abstract: Disclosed herein is a process for the reductive alkylation of primary amines to form secondary amines, by high pressure reaction of the primary amine with an alkylating agent and hydrogen in the presence of a catalyst which comprises metallic palladium. A process of the present invention is characterized in having high conversion rates and high selectivities, both greater than 95% on a first pass through the reactor. According to a preferred embodiment, the secondary amine produced comprises at least one 2-alkyl group bonded to the nitrogen atom of the primary amine product.
    Type: Application
    Filed: July 22, 2002
    Publication date: January 22, 2004
    Applicant: Huntsman Petrochemical Corporation
    Inventors: Wei-Yaug Su, Christopher H. Nelli
  • Patent number: 6620971
    Abstract: An asymmetric &bgr;-ketoiminate ligand compound, represented by the following chemical formula (4): wherein, R1 is a linear or branched alkyl group containing 1 to 8 carbon atoms; R2 is a linear or branched alkyl group containing 2 to 9 carbon atoms, with the proviso that R2 contains more carbon atoms than R1; R′ is a linear or branched alkylene group containing 1 to 8 carbon atoms or a hydrocarbon containing 1 to 3 ethylene ether or propylene ether moieties, represented by —(CH2)nO— (n=2 or 3); R3 is a hydrogen atom or a linear or branched alkyl group containing 1 to 9 carbon atoms; and X is an oxygen atom or a sulfur atom.
    Type: Grant
    Filed: January 22, 2002
    Date of Patent: September 16, 2003
    Assignee: Samsung Electronics Co., Ltd.
    Inventors: Seok Chang, Soon Taik Hwang, Euk Che Hwang
  • Publication number: 20030139628
    Abstract: A process produces an optically active amine or its salt and includes the steps of reacting a ketone of Formula (1a) 1
    Type: Application
    Filed: December 6, 2002
    Publication date: July 24, 2003
    Inventors: Hiroki Tanaka, Li Rui Pan, Kiyoshi Ikura
  • Patent number: 6563004
    Abstract: Monoisopropylamine is prepared by reacting acetone with ammonia and with hydrogen at elevated temperature and elevated pressure in the presence of a catalyst, wherein the catalytically active mass of the catalyst comprises, after its preparation and before the treatment with hydrogen, from 20 to 90% by weight of aluminum oxide (Al2O3), zirconium dioxide (ZrO2), titanium dioxide (TiO2) and/or silicon dioxide (SiO2), from 1 to 70% by weight of oxygen-containing compounds of copper, calculated as CuO, from 1 to 70% by weight of oxygen-containing compounds of nickel, calculated as NiO, and from 1 to 70% by weight of oxygen-containing compounds of cobalt, calculated as CoO.
    Type: Grant
    Filed: December 5, 2000
    Date of Patent: May 13, 2003
    Assignee: BASF Aktiengesellschaft
    Inventors: Jan Nouwen, Stefan Käshammer, Arthur Höhn, Frank Funke, Johann-Peter Melder, Frank Gutschoven, Philip Buskens
  • 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: 6365778
    Abstract: Aqueous, alcoholic or aqueous-alcoholic solutions of a monoalkylamine and a reducing sugar are simultaneously injected into a mixing unit and the two solutions are mixed under turbulence in the mixing unit for 6 seconds to 5 minutes at a temperature of 25 to 60° C. and a pressure of 50 to 90 bar. The mixture is then added to a hydrogenation reactor and hydrogenated with hydrogen in the presence of a hydrogenation catalyst. An alkylpolyhydroxyalkylamine is obtained in high yield and with high purity.
    Type: Grant
    Filed: March 9, 2000
    Date of Patent: April 2, 2002
    Assignee: Clariant GmbH
    Inventors: Andreas Gallas, Johann Franz Hanauer, Hubert Seitz, Frank Weinelt
  • Patent number: 6323370
    Abstract: The present invention relates to methods for the reductive amination of a carbonyl-containing compound. R1R2CO where R1 and R2 are either H, alkyl, aryl or heterocyclic etc with an amine NHR3R4 where R3 and R4 arm H, alkyl, aryl, or heterocyclic in the presence of a homogeneous iridium catalyst and gaseous hydrogen.
    Type: Grant
    Filed: August 25, 2000
    Date of Patent: November 27, 2001
    Assignee: Johnson Matthey Public Limited Company
    Inventors: Penelope Ann Chaloner, Simon Collard, Richard David Ellis, Ann Kathleen Keep
  • 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
  • Publication number: 20010003137
    Abstract: Monoisopropylamine is prepared by reacting acetone with ammonia and with hydrogen at elevated temperature and elevated pressure in the presence of a catalyst, wherein the catalytically active mass of the catalyst comprises, after its preparation and before the treatment with hydrogen,
    Type: Application
    Filed: December 5, 2000
    Publication date: June 7, 2001
    Inventors: Jan Nouwen, Stefan Kashammer, Arthur Hohn, Frank Funke, Johann-Peter Melder, Frank Gutschoven, Philip Buskens
  • Patent number: 6187957
    Abstract: Amines are prepared by reacting primary or secondary alcohols, aldehydes or ketones with nitrogen compounds selected from the group consisting of ammonia and primary and secondary amines at elevated temperatures and superatmospheric pressures in the presence of hydrogen and of a catalyst containing copper and oxygen-containing compounds of titanium by a process in which the catalyst is used in the form of moldings which have been prepared with the addition of metallic copper powder.
    Type: Grant
    Filed: December 14, 1999
    Date of Patent: February 13, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerald Meyer, Frank Funke, Gerhard Schulz, Detlef Kratz, Marc Walter, Michael Hesse
  • Patent number: 6013816
    Abstract: Process for the preparation of a linear .omega.-formyl-carboxylic acid or a corresponding linear formylnitrile compound starting from an internally unsaturated C.sub.4 -C.sub.12 carboxylic acid or a corresponding ester or nitrile by means of hydroformylation in the presence of carbon monoxide, hydrogen and a catalyst system, wherein the hydroformylation is carried out in an aqueous medium and in that the catalyst system comprises platinum and a water-soluble organic bidentate ligand.
    Type: Grant
    Filed: July 5, 1996
    Date of Patent: January 11, 2000
    Assignee: DSM NV
    Inventors: Onko J. Gelling, Imre Toth
  • Patent number: 5998669
    Abstract: The present invention relates to a process of making 2-amino-1,3-propanediol by reacting 1,3-dihyrdroxyacetone dimer with an amine compound.
    Type: Grant
    Filed: September 17, 1998
    Date of Patent: December 7, 1999
    Assignee: Abbott Laboratories
    Inventors: Russell C. Klix, Deborah A. Davis, Owen J. Goodmonson
  • Patent number: 5885538
    Abstract: The present invention provides a method and composition regeneration of an aminal that has previously been reacted with a sulfide selected from hydrogen sulfide and mercaptans. The method includes contacting a scavenging mixture which includes an aminal, and an oxidation catalyst with a gas such as air, oxygen enriched air, oxygen, ozone enriched air and ozone. The composition includes an aminal, and an oxidation catalyst. The method and composition are useful for the regeneration of an aminal base sulfur scavenging compound.
    Type: Grant
    Filed: July 2, 1997
    Date of Patent: March 23, 1999
    Assignee: Quaker Chemical Corporation
    Inventors: Edward A. Trauffer, Muge Caglar
  • Patent number: 5840986
    Abstract: A process for preparing N-alkyl-substituted aminoalkynes by reacting an alkyne with a carbonyl compound and an amine with heterogeneous catalysis in which an unsupported copper acetylide derived from malachite is used as the catalyst. The N-alkyl-substituted aminoalkyne have a wide variety of uses including their use as precursors for pharmaceuticals, their use in electroplating processes and their use as corrosion inhibitors.
    Type: Grant
    Filed: September 4, 1997
    Date of Patent: November 24, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Thomas Preiss, Jochem Henkelmann, Joachim Wulff-Doring, Susanne Stutz
  • Patent number: 5811459
    Abstract: The invention relates to compounds of the formula (I): ##STR1## wherein A, B and D are various ring systems such as phenyl, R.sup.1 includes carboxy, R.sup.3 is hydrogen or C.sub.1-4 alkyl and Z is a linking group such as --(CH(R.sup.5)).sub.m -- wherein m is 2, 3 or 4, and R.sub.5 includes hydrogen and methyl; and pharmaceutically acceptable salts and in vivo hydrolysable esters or amides thereof, processes for preparing these compounds, pharmaceutical compositions comprising them, and their use in the treatment of pain.
    Type: Grant
    Filed: June 4, 1996
    Date of Patent: September 22, 1998
    Assignee: Zeneca Limited
    Inventors: Gloria Ann Breault, John Oldfield, Howard Tucker, Peter Warner
  • Patent number: 5808160
    Abstract: Hydroxyalkyl-substituted aminoalkynes of the general formula I ##STR1## where at least one of the substituents R.sup.1, R.sup.4 or R.sup.5 is hydroxyalkyl are prepared in a reaction with heterogeneous catalysis.
    Type: Grant
    Filed: April 25, 1997
    Date of Patent: September 15, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Thomas Ruhl, Thomas Preiss, Jochem Henkelmann