By Reductive Amination Patents (Class 564/472)
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Patent number: 10899726Abstract: 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: GrantFiled: July 8, 2015Date of Patent: January 26, 2021Assignee: RHODIA OPERATIONSInventors: Peng Li, Floryan Decampo
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Patent number: 8916728Abstract: 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: GrantFiled: June 25, 2010Date of Patent: December 23, 2014Assignee: Arkema FranceInventors: Christophe Ruppin, François Guillemet
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Publication number: 20140275475Abstract: 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: ApplicationFiled: March 11, 2014Publication date: September 18, 2014Applicant: Bayer Intellectual Property GmbHInventors: Thomas Ernst Müller, Christoph Gürtler, Walter Leitner, Henning Vogt, Saeeda Soomro
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Publication number: 20140275371Abstract: 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: ApplicationFiled: March 11, 2014Publication date: September 18, 2014Applicant: Bayer Intellectual Property GmbHInventors: Thomas Ernst Müller, Christoph Gürtler, Walter Leitner, Henning Vogt, Saeeda Soomro
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Patent number: 8653306Abstract: 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: GrantFiled: December 21, 2012Date of Patent: February 18, 2014Assignee: Penn A Kem LLCInventors: Shridhar G. Hegde, Lei Zhao
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Publication number: 20130310560Abstract: 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: ApplicationFiled: November 8, 2012Publication date: November 21, 2013Applicant: BASF SEInventors: PETR KUBANEK, WOLFGANG MÄRGELEIN, EKKEHARD SCHWAB, JOHANN-PETER MELDER, MANFRED JULIUS
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Patent number: 8211949Abstract: 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: GrantFiled: September 16, 2008Date of Patent: July 3, 2012Assignee: Dow Global Technologies LLCInventors: Pierre T. Varineau, Brian W. Kolthammer, Aaron W. Sanders, David A. Wilson, Kara S. Weber, Robert Kirk Thompson, Cynthia L. Rand, Thomas C. Eisenschmid
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Publication number: 20120116126Abstract: 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: ApplicationFiled: June 25, 2010Publication date: May 10, 2012Inventors: Christophe Ruppin, Francois Guillemet
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Patent number: 8093431Abstract: 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: GrantFiled: February 2, 2009Date of Patent: January 10, 2012Assignee: Clearwater International LLCInventors: Olusegun Matthew Falana, Ray Veldman, Frank Zamora, Emilia U. Ugwu, Zoraida Vazquez
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Patent number: 8034978Abstract: 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: GrantFiled: May 24, 2007Date of Patent: October 11, 2011Assignee: BASF SEInventors: Jan Eberhardt, Harald Meiβner, Bram Willem Hoffer, Johann-Peter Melder, Ekkehard Schwab
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Patent number: 8012913Abstract: 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: GrantFiled: October 10, 2006Date of Patent: September 6, 2011Assignee: Clearwater International LLCInventors: Larry W. Gatlin, Daniel R. Dostie, Timothy Eric Gatlin
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Patent number: 7985882Abstract: 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: GrantFiled: August 23, 2002Date of Patent: July 26, 2011Assignee: Biotage ABInventors: Sukanta Bhattacharyya, Jeffrey W. Labadie, Owen W. Gooding, Sunil Rana
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Publication number: 20110137030Abstract: 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: ApplicationFiled: December 2, 2010Publication date: June 9, 2011Applicant: BASF SEInventors: Petr Kubanek, Wolfgang Mägerlein, Johann-Peter Melder, Thomas Heidemann
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Publication number: 20100274011Abstract: 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: ApplicationFiled: December 10, 2008Publication date: October 28, 2010Applicant: BASF SEInventors: Petr Kubanek, Wolfgang Mägerlein, Ekkehard Schwab, Johann-Peter Melder, Manfred Julius
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Patent number: 7754922Abstract: 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: GrantFiled: July 4, 2007Date of Patent: July 13, 2010Assignee: BASF SEInventors: Petr Kubanek, Bram Willem Hoffer, Ekkehard Schwab, Johann-Peter Melder, Holger Evers, Till Gerlach
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Publication number: 20090312579Abstract: 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: ApplicationFiled: July 4, 2007Publication date: December 17, 2009Applicant: BASF SEInventors: Petr Kubanek, Bram Willem Hoffer, Ekkehard Schwab, Johann-Peter Melder
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Patent number: 7619119Abstract: 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: GrantFiled: June 7, 2007Date of Patent: November 17, 2009Assignee: The Procter & Gamble CompanyInventors: Victor Manuel Arredondo, Patrick Joseph Corrigan, Angella Christine Cearley, Deborah Jean Back, Michael Steven Gibson, Neil Thomas Fairweather
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Patent number: 7619118Abstract: 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: GrantFiled: June 7, 2007Date of Patent: November 17, 2009Assignee: The Procter & Gamble CompanyInventors: Victor Manuel Arredondo, Patrick Joseph Corrigan
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Publication number: 20090275781Abstract: 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: ApplicationFiled: July 4, 2007Publication date: November 5, 2009Applicant: BASF SEInventors: Petr Kubanek, Bram Willem Hoffer, Ekkehard Schwab, Johann-Peter Melder, Holger Evers, Till Gerlach
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Patent number: 7405327Abstract: 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: GrantFiled: May 4, 2005Date of Patent: July 29, 2008Assignee: BASF AktiengesellschaftInventors: Frank Haese, Arnd Bottcher, Bernd Stein, Wolfgang Reif, Johann-Peter Melder, Karl-Heinz Roβ, Heinz Rutter, Shelue Liang, Stefan Rittinger
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Patent number: 7230134Abstract: 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: GrantFiled: August 6, 2002Date of Patent: June 12, 2007Assignee: Degussa AGInventors: Armin Borner, Uwe Dingerdissen, Renat Kadyrov, Thomas Riermeier, Vitali Tararov
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Patent number: 7183438Abstract: 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: GrantFiled: March 7, 2003Date of Patent: February 27, 2007Assignee: BASF AktiengesellschaftInventors: Till Gerlach, Frank Funke, Johann-Peter Melder, Stefan Iselborn, Martin Rudloff, Michael Hüllmann
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Patent number: 7176332Abstract: 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: GrantFiled: August 26, 2002Date of Patent: February 13, 2007Assignees: Victoria University of Technology, Polychip Pharmaceuticals Pty. Ltd.Inventors: Andrew John Smallridge, Maurice Arthur Trewhella, Kylie Anne Wilkinson
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Patent number: 7122702Abstract: 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: GrantFiled: December 10, 2003Date of Patent: October 17, 2006Assignee: BASF AktiengesellschaftInventors: Till Gerlach, Frank Funke, Johann-Peter Melder
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Patent number: 7074963Abstract: 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: GrantFiled: July 18, 2003Date of Patent: July 11, 2006Assignee: Huntsman Petrochemical CorporationInventors: Wei-Yang Su, Christopher H. Nelli
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Patent number: 7034186Abstract: 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: GrantFiled: December 10, 2003Date of Patent: April 25, 2006Assignee: BASF AktiengesellschaftInventors: Till Gerlach, Frank Funke, Johann-Peter Melder
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Patent number: 7001708Abstract: 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: GrantFiled: November 27, 2002Date of Patent: February 21, 2006Assignee: University of Central Florida Research Foundation, Inc.Inventor: Kevin D. Belfield
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Patent number: 6982352Abstract: 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: GrantFiled: March 19, 2004Date of Patent: January 3, 2006Assignee: Celanese Chemicals Europe GmbHInventors: Peter Lappe, Helmut Springer
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Publication number: 20040267051Abstract: 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: ApplicationFiled: August 18, 2004Publication date: December 30, 2004Inventors: Amin Boerner, Uwe Dingerdissen, Renat Kaxyrov, Thomas Riermeier, Vitali Tararov
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Publication number: 20040225133Abstract: 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: ApplicationFiled: May 6, 2004Publication date: November 11, 2004Applicant: Battelle Memorial InstituteInventor: Johnathan E. Holladay
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Publication number: 20040122259Abstract: 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: ApplicationFiled: December 10, 2003Publication date: June 24, 2004Inventors: Till Gerlach, Frank Funke, Johann-Peter Melder
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Patent number: 6696608Abstract: 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: GrantFiled: February 14, 2002Date of Patent: February 24, 2004Assignee: Avecia LimitedInventors: Juliette Martin, Lynne Alison Campbell
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Patent number: 6689914Abstract: 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: GrantFiled: September 5, 2002Date of Patent: February 10, 2004Assignee: BASF AktiengesellschaftInventors: Martin Schäfer, Arnd Böttcher, Andreas Kramer, Arthur Höhn, Shelue Liang, Frank Funke
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Publication number: 20040019238Abstract: 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: ApplicationFiled: July 18, 2003Publication date: January 29, 2004Applicant: Huntsman Petrochemical CorporationInventors: Wei-Yang Su, Christopher H. Nelli
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Publication number: 20040015016Abstract: 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: ApplicationFiled: July 22, 2002Publication date: January 22, 2004Applicant: Huntsman Petrochemical CorporationInventors: Wei-Yaug Su, Christopher H. Nelli
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Patent number: 6620971Abstract: 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: GrantFiled: January 22, 2002Date of Patent: September 16, 2003Assignee: Samsung Electronics Co., Ltd.Inventors: Seok Chang, Soon Taik Hwang, Euk Che Hwang
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Publication number: 20030139628Abstract: A process produces an optically active amine or its salt and includes the steps of reacting a ketone of Formula (1a) 1Type: ApplicationFiled: December 6, 2002Publication date: July 24, 2003Inventors: Hiroki Tanaka, Li Rui Pan, Kiyoshi Ikura
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Patent number: 6563004Abstract: 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: GrantFiled: December 5, 2000Date of Patent: May 13, 2003Assignee: BASF AktiengesellschaftInventors: Jan Nouwen, Stefan Käshammer, Arthur Höhn, Frank Funke, Johann-Peter Melder, Frank Gutschoven, Philip Buskens
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Patent number: 6525222Abstract: 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: GrantFiled: December 5, 2000Date of Patent: February 25, 2003Assignee: BASF AktiengesellschaftInventors: Jan Nouwen, Arthur Höhn, Horst Neuhauser, Frank Funke, Stephan Andreas Schunk, Johann-Peter Melder, Knut Eger, Michael Hesse, Joachim Wulff-Döring
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Patent number: 6365778Abstract: 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: GrantFiled: March 9, 2000Date of Patent: April 2, 2002Assignee: Clariant GmbHInventors: Andreas Gallas, Johann Franz Hanauer, Hubert Seitz, Frank Weinelt
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Patent number: 6323370Abstract: 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: GrantFiled: August 25, 2000Date of Patent: November 27, 2001Assignee: Johnson Matthey Public Limited CompanyInventors: Penelope Ann Chaloner, Simon Collard, Richard David Ellis, Ann Kathleen Keep
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Publication number: 20010003136Abstract: 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: ApplicationFiled: December 5, 2000Publication date: June 7, 2001Inventors: Jan Nouwen, Arthur Hohn, Horst Neuhauser, Frank Funke, Stephan Andreas Schunk, Johann-Peter Melder, Knut Eger, Michael Hesse, Joachim Wulff-Doring
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Publication number: 20010003137Abstract: 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: ApplicationFiled: December 5, 2000Publication date: June 7, 2001Inventors: Jan Nouwen, Stefan Kashammer, Arthur Hohn, Frank Funke, Johann-Peter Melder, Frank Gutschoven, Philip Buskens
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Patent number: 6187957Abstract: 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: GrantFiled: December 14, 1999Date of Patent: February 13, 2001Assignee: BASF AktiengesellschaftInventors: Gerald Meyer, Frank Funke, Gerhard Schulz, Detlef Kratz, Marc Walter, Michael Hesse
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Patent number: 6013816Abstract: 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: GrantFiled: July 5, 1996Date of Patent: January 11, 2000Assignee: DSM NVInventors: Onko J. Gelling, Imre Toth
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Patent number: 5998669Abstract: 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: GrantFiled: September 17, 1998Date of Patent: December 7, 1999Assignee: Abbott LaboratoriesInventors: Russell C. Klix, Deborah A. Davis, Owen J. Goodmonson
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Patent number: 5885538Abstract: 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: GrantFiled: July 2, 1997Date of Patent: March 23, 1999Assignee: Quaker Chemical CorporationInventors: Edward A. Trauffer, Muge Caglar
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Patent number: 5840986Abstract: 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: GrantFiled: September 4, 1997Date of Patent: November 24, 1998Assignee: BASF AktiengesellschaftInventors: Thomas Preiss, Jochem Henkelmann, Joachim Wulff-Doring, Susanne Stutz
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Patent number: 5811459Abstract: 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: GrantFiled: June 4, 1996Date of Patent: September 22, 1998Assignee: Zeneca LimitedInventors: Gloria Ann Breault, John Oldfield, Howard Tucker, Peter Warner
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Patent number: 5808160Abstract: 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: GrantFiled: April 25, 1997Date of Patent: September 15, 1998Assignee: BASF AktiengesellschaftInventors: Thomas Ruhl, Thomas Preiss, Jochem Henkelmann