Catalyst Utilized Patents (Class 564/479)
  • Patent number: 11104637
    Abstract: The present invention relates to a process for the conversion of 2-aminoethanol to ethane-1,2-diamine and/or linear polyethylenimines of the formula H2N—[CH2CH2NH]n—CH2CH2NH2 wherein n?1 comprising: (i) providing a catalyst comprising a zeolitic material having the MOR framework structure comprising YO2 and X2O3, wherein Y is a tetravalent element and X is a trivalent element, said zeolitic material containing copper as extra-framework ions; (ii) providing a gas stream comprising 2-aminoethanol and ammonia; (iii) contacting the catalyst provided in (i) with the gas stream provided in (ii) for converting 2-aminoethanol to ethane-1,2-diamine and/or linear polyethylenimines.
    Type: Grant
    Filed: November 29, 2017
    Date of Patent: August 31, 2021
    Assignee: BASF SE
    Inventors: Andrei-Nicolae Parvulescu, Alvaro Gordillo, Marie Katrin Schroeter, Johann-Peter Melder, Juergen Bechtel, Thomas Heidemann, Stephan A. Schunk, Ulrich Müller
  • Patent number: 11091425
    Abstract: The present invention relates to a process for the conversion of ethane-1,2-diol to ethane-1,2-diamine and/or linear polyethylenimines of the formula H2N—[CH2CH2NH]n—CH2CH2NH2 wherein n?1 comprising (i) providing a catalyst comprising a zeolitic material comprising YO2 and X2O3, wherein Y is a tetravalent element and X is a trivalent element, wherein the zeolitic material is selected from the group consisting of zeolitic materials having the MOR, FAU, CHA and/or GME framework structure, including combinations of two or more thereof; (ii) providing a gas stream comprising ethane-1,2-diol and ammonia; (iii) contacting the catalyst provided in (i) with the gas stream provided in (ii) for converting ethane-1,2-diol to ethane-1,2-diamine and/or linear polyethylenimines.
    Type: Grant
    Filed: November 29, 2017
    Date of Patent: August 17, 2021
    Assignee: BASF SE
    Inventors: Andrei-Nicolae Parvulescu, Alvaro Gordillo, Marie Katrin Schroeter, Johann-Peter Melder, Juergen Bechtel, Thomas Heidemann, Stephan A. Schunk, Ulrich Müller
  • Patent number: 10975017
    Abstract: A process for preparing polyethyleneamines of formula NH2-(CH2-CH2-NH-)pH wherein p is at least 3 and wherein one or more —NH-CH2-CH2-NH— units may be piperazine units and/or ethylene urea derivatives of these compounds, includes reacting monoethylene glycol with an amine-functional compound having at least two —NH— units, of which at least one is selected from primary amine groups and cyclic secondary amine groups, in the presence of a carbon oxide-delivering agent. The amine-functional compound includes at least one —NH-CH2-CH2-NH— unit, and one or more —NH-CH2-CH2-NH— units may be in the form of cyclic ethylene urea moieties, piperazine moieties, or linear ethylene urea moieties. The molar ratio of amine-functional compound to monoethylene glycol is above 1.2:1 and the molar ratio of carbon oxide delivering agent to —NH-CH2-CH2-NH— units is at least 0.5:1. The process makes it possible to obtain ethylene amines and derivatives thereof without using ammonia or metal-containing catalysts.
    Type: Grant
    Filed: December 12, 2017
    Date of Patent: April 13, 2021
    Assignee: NOURYON CHEMICALS INTERNATIONAL B.V.
    Inventors: Eike Nicolas Kantzer, Karl Fredrik Lake, Antoon Jacob Berend Ten Kate, Michiel Jozef Thomas Raaijmakers, Rens Veneman, Ina Ehlers, Michael Bertil Einar Sarning, Hendrik Van Dam, Rolf Krister Edvinsson, Jenny Valborg Therese Adrian Meredith
  • Patent number: 10844001
    Abstract: The present invention relates to a process to prepare ethylene amines of the formula NH2—(C2H4—NH—)pH wherein p is at least 3 or derivatives thereof wherein one or more units —NH—C2H4—NH— may be present as a cyclic ethylene urea unit or between two units —NH—C2H4—NH— a carbonyl moiety is present, by reacting an ethanolamine-functional compound, an amine-functional compound in the presence of a carbon oxide delivering agent, wherein the molar ratio of carbon oxide delivering agent to amine-functional compound is at least 0.6 to 1.
    Type: Grant
    Filed: February 10, 2017
    Date of Patent: November 24, 2020
    Assignee: NOURYON CHEMICALS INTERNATIONAL B.V.
    Inventors: Rolf Krister Edvinsson, Eike Nicolas Kantzer, Per Fredrik Olmo Larsson, Karl Fredrik Lake, Antoon Jacob Berend Ten Kate
  • Patent number: 10836704
    Abstract: Preparing ethanolamines/ethyleneamines in the presence of an amination catalyst prepared by reducing a calcined catalyst precursor containing one or more metals of groups 8, 9, 10 and/or 11 and low basicity achieved by: a) coprecipitating catalyst precursor and active composition additionally contains alkali metals or alkaline earth metals; b) the catalyst precursor is prepared by impregnating a support material or precipitative application onto a support material containing alkali metals, Be, Ca, Ba, Sr, hydrotalcite, chrysotile or sepiolite; c) the catalyst precursor is prepared by impregnating a support material or precipitative application onto a support material and the active composition of the catalyst support contains one or more of alkali metals and alkaline earth metals; d) the catalyst precursor is calcined at temperatures of 600° C. or more; or e) the catalyst precursor is prepared by a combination of a) and d), b) and d), or c) and d).
    Type: Grant
    Filed: December 7, 2017
    Date of Patent: November 17, 2020
    Assignee: BASF SE
    Inventors: Marie Katrin Schroeter, Alvaro Gordillo, Andrei-Nicolae Parvulescu, Johann-Peter Melder, Carlos Lizandara Pueyo, Juergen Bechtel, Thomas Heidemann, Stephan A. Schunk, Ulrich Mueller
  • Patent number: 9518005
    Abstract: Processes are disclosed for the conversion of a carbohydrate source to hexamethylenediamine (HMDA) and to intermediates useful for the production of hexamethylenediamine and other industrial chemicals. HMDA is produced by direct reduction of a furfural substrate to 1,6-hexanediol in the presence of hydrogen and a heterogeneous reduction catalyst comprising Pt or by indirect reduction of a furfural substrate to 1,6-hexanediol wherein 1,2,6-hexanetriol is produced by reduction of the furfural substrate in the presence of hydrogen and a catalyst comprising Pt and 1,2,6-hexanediol is then converted by hydrogenation in the presence of a catalyst comprising Pt to 1,6 hexanediol, each process then proceding to the production of HMDA by known routes, such as amination of the 1,6 hexanediol. Catalysts useful for the direct and indirect production of 1,6-hexanediol are also disclosed.
    Type: Grant
    Filed: April 15, 2015
    Date of Patent: December 13, 2016
    Assignee: Rennovia Inc.
    Inventors: Eric L. Dias, James A. W. Shoemaker, Thomas R. Boussie, Vincent J. Murphy
  • Patent number: 9061964
    Abstract: The present invention discloses the method for producing a tertiary amine, using the column reactor packed with catalyst layers, containing supplying a liquid and a gaseous raw materials from the bottom of the column, reacting these raw materials in the column, and discharging the product from the top of the column, wherein the column reactor includes two or more honeycomb catalyst layers as the catalyst layers, one or more spaces between each honeycomb catalyst layer, and one or more rectifying sections that prevents a partial or whole back flow of the raw materials, arranged in each space without contacting with the honeycomb catalyst layer.
    Type: Grant
    Filed: July 10, 2014
    Date of Patent: June 23, 2015
    Assignee: KAO CORPORATION
    Inventors: Yasumitsu Sakuma, Wataru Nomura, Goshi Yamamoto, Takeshi Narushima
  • Patent number: 9018423
    Abstract: Disclosed herein are processes for preparing an ?,?-Cn-diol, wherein n is 5 or greater, from a feedstock comprising a Cn oxygenate. In one embodiment, the process comprises contacting the feedstock with hydrogen gas in the presence of a catalyst comprising Pt, Cu, Ni, Pd, Pt, Rh, Ir, Ru, or Fe on a WO3 or WOx support. In one embodiment, the process comprises contacting the feedstock with hydrogen in the presence of a catalyst comprising a metal M1 and a metal M2 or an oxide of M2, and optionally a support. In one embodiment, M1 is Pd, Pt, or Ir; and M2 is Mo, W, V, Mn, Re, Zr, Ni, Cu, Zn, Cr, Ge, Sn, Ti, Au, or Co. The Cn oxygenate may be obtained from a biorenewable resource.
    Type: Grant
    Filed: April 25, 2013
    Date of Patent: April 28, 2015
    Assignee: E I du Pont de Nemours and Company
    Inventors: Alan Martin Allgeier, Torren Ryan Carlson, David Richard Corbin, Wathudura Indika Namal De Silva, Ekaterini Korovessi, Carl Andrew Menning, Joachim C Ritter, H David Rosenfeld, Sourav Kumar Sengupta
  • Patent number: 9000218
    Abstract: The present application relates to a process for preparing secondary amines by aminating excess primary or secondary alcohols with primary amines in the liquid phase in the presence of copper-comprising catalysts.
    Type: Grant
    Filed: January 9, 2013
    Date of Patent: April 7, 2015
    Assignee: BASF SE
    Inventors: Christof Wilhelm Wigbers, Johann-Peter Melder, Bernd Stein
  • Publication number: 20150087837
    Abstract: The present invention provides techniques that selectively recover Re from reductive amination catalysts. In particular, the present invention allows Re to be recovered selectively relative to Ni, Co, and/or Cu, and particularly Ni, that are often present on reductive amination catalysts. The present invention uses a combination of oxidation and extraction techniques to selectively recover Re relative to Ni, Co, and/or Cu. Advantageously, the recovery is selective even when using aqueous solutions for extraction.
    Type: Application
    Filed: March 11, 2013
    Publication date: March 26, 2015
    Inventors: Stephen W. King, William C. Hoffman
  • Publication number: 20150057467
    Abstract: Process to prepare ethylene amines by the amination of ethylene oxide, ethylene glycol or ethanolamine in the presence of a catalyst, including a step wherein methylamine and ethylamine are removed from the reaction effluents, wherein the methylamine and the ethylamine are adsorbed onto or absorbed by absorbents and adsorbents (absorption/adsorption) and wherein the absorption/adsorption takes place in the liquid phase or in the gas phase.
    Type: Application
    Filed: October 30, 2014
    Publication date: February 26, 2015
    Applicant: AKZO NOBEL N.V.
    Inventors: Martin Stefan HANSON, Leif Kenny Christian GUSTAFSON, Johan LIF, Boris KUZMANOVIC, Ulf SCHRÖDER
  • Patent number: 8952198
    Abstract: Disclosed is a process for the preparation of an amine (particularly diamines and polyamines) by reacting an alkanolamine or a polyol with ammonia in the presence of a catalyst composed of two active metals from the group of transition metals, namely nickel and chromium supported on a microporous refractory substrate, in a hydrogenated, trickle bed reactor.
    Type: Grant
    Filed: January 30, 2013
    Date of Patent: February 10, 2015
    Inventors: Ian Williams, John Christopher Williams, German Maya Maya-Hernandez, Lilia Patricia Hernandez Salas, Miguel Angel Lopez Guerrero
  • Patent number: 8927772
    Abstract: The present invention relates to a process for producing a tertiary amine, including the following steps (1) and (2): Step (1); introducing an alcohol having 1 to 36 carbon atoms and a raw amine represented by the following general formula (I) into a first reaction vessel to react with each other in the presence of a catalyst and hydrogen, and then continuing the reaction while discharging water produced in the reaction and a hydrogen-containing gas out of a reaction system in the first reaction vessel: R1R2NH??(I) wherein R1 and R2 are each independently a hydrogen atom or a hydrocarbon group having 1 to 36 carbon atoms; and Step (2): introducing the hydrogen-containing gas discharged from the first reaction vessel into a second reaction vessel to reduce an amount of carbon monoxide contained in the hydrogen-containing gas, and then introducing a part or whole of the hydrogen-containing gas into the first reaction vessel.
    Type: Grant
    Filed: December 27, 2011
    Date of Patent: January 6, 2015
    Assignee: Kao Corporation
    Inventors: Masahiko Watanabe, Gosuke Tateno, Hirofumi Mizukoshi
  • Patent number: 8912361
    Abstract: Process for preparing primary amines which have at least one functional group of the formula (—CH2—NH2) and at least one further primary amino group by alcohol amination of starting materials having at least one functional group of the formula (—CH2—OH) and at least one further functional group (—X), where (—X) is selected from among hydroxyl groups and primary amino groups, by means of ammonia with elimination of water, wherein the reaction is carried out homogeneously catalyzed in the presence of at least one complex catalyst comprising at least one element selected from groups 8, 9 and 10 of the Periodic Table and also at least one donor ligand.
    Type: Grant
    Filed: March 8, 2012
    Date of Patent: December 16, 2014
    Assignee: BASF SE
    Inventors: Thomas Schaub, Boris Buschhaus, Marion Kristina Brinks, Mathias Schelwies, Rocco Paciello, Johann-Peter Melder, Martin Merger
  • Patent number: 8895784
    Abstract: The present invention relates to a catalyst for reductive amination-reaction, and uses thereof. The catalyst according to the present invention can show high amine conversion rate because it can maintain the catalytic activity even in the presence of moisture especially while maintaining the balance of dehydrogenation and hydrogenation reaction basically. Accordingly, the catalyst can be usefully used for preparing a polyetheramine compound through reductive amination-reaction not only in a continuous preparation process but also in a batch preparation process, irrespective of the existence of moisture.
    Type: Grant
    Filed: May 9, 2013
    Date of Patent: November 25, 2014
    Assignee: Lotte Chemical Corporation
    Inventors: Kyung-Jun Kim, Chun-Sik Byun, Jin-Heung Kim, Hui-Chan Kim, Young-Jong Seo
  • Patent number: 8877977
    Abstract: Process for the preparation of polyalkylenepolyamines by homogeneously catalyzed alcohol amination, in which aliphatic amino alcohols are reacted with one another or aliphatic diamines or polyamines are reacted with aliphatic diols or polyols with the elimination of water in the presence of a homogeneous catalyst and in the presence of hydrogen gas. Polyalkylenepolyamines obtainable by such processes and polyalkylenepolyamines comprising hydroxy groups, secondary amines or tertiary amines. Uses of such polyalkylenepolyamines as adhesion promoters for printing inks, adhesion promoters in composite films, cohesion promoters for adhesives, crosslinkers/curing agents for resins, primers for paints, wet-adhesion promoters for emulsion paints, complexing agents and flocculating agents, penetration assistants in wood preservation, corrosion inhibitors, immobilizing agents for proteins and enzymes.
    Type: Grant
    Filed: November 19, 2012
    Date of Patent: November 4, 2014
    Assignee: BASF SE
    Inventors: Julia Strautmann, Thomas Schaub, Stephan Hueffer, Steffen Maas, Rocco Paciello
  • Patent number: 8877978
    Abstract: The present invention discloses the method for producing a tertiary amine, using the column reactor packed with catalyst layers, containing supplying a liquid and a gaseous raw materials from the bottom of the column, reacting these raw materials in the column, and discharging the product from the top of the column, wherein the column reactor includes two or more honeycomb catalyst layers as the catalyst layers, one or more spaces between each honeycomb catalyst layer, and one or more rectifying sections that prevents a partial or whole back flow of the raw materials, arranged in each space without contacting with the honeycomb catalyst layer.
    Type: Grant
    Filed: December 19, 2011
    Date of Patent: November 4, 2014
    Assignee: Kao Corporation
    Inventors: Yasumitsu Sakuma, Wataru Nomura, Goshi Yamamoto, Takeshi Narushima
  • Patent number: 8865940
    Abstract: Disclosed are processes for preparing 1,6-hexanediol and synthetic intermediates useful in the production of 1,6-hexanediol from renewable biosources. In one embodiment, a process comprises contacting levoglucosenone with hydrogen in the presence of a first hydrogenation catalyst at a first temperature to form product mixture (I); and heating product mixture (I) in the presence of hydrogen and a second hydrogenation catalyst at a second temperature to form product mixture (II) which comprises 1,6-hexanediol. In one embodiment, the 1,6-hexanediol is converted to 1,6-diaminohexane.
    Type: Grant
    Filed: April 25, 2013
    Date of Patent: October 21, 2014
    Assignee: E I du Pont de Nemours and Company
    Inventors: Alan Martin Allgeier, Wathudura Indika Namal De Silva, Ekaterini Korovessi, Carl Andrew Menning, Joachim C Ritter, Sourav Kumar Sengupta, Christina S Stauffer
  • Patent number: 8853458
    Abstract: Processes are disclosed for the conversion of a carbohydrate source to hexamethylenediamine (HMDA) and to intermediates useful for the production of hexamethylenediamine and other industrial chemicals. HMDA is produced by direct reduction of a furfural substrate to 1,6-hexanediol in the presence of hydrogen and a heterogeneous reduction catalyst comprising Pt or by indirect reduction of a furfural substrate to 1,6-hexanediol wherein 1,2,6-hexanetriol is produced by reduction of the furfural substrate in the presence of hydrogen and a catalyst comprising Pt and 1,2,6-hexanediol is then converted by hydrogenation in the presence of a catalyst comprising Pt to 1,6 hexanediol, each process then proceeding to the production of HMDA by known routes, such as amination of the 1,6 hexanediol. Catalysts useful for the direct and indirect production of 1,6-hexanediol are also disclosed.
    Type: Grant
    Filed: January 11, 2013
    Date of Patent: October 7, 2014
    Assignee: Rennovia, Inc.
    Inventors: Eric L. Dias, James A. W. Shoemaker, Thomas R. Boussie, Vincent J. Murphy
  • Patent number: 8846985
    Abstract: Disclosed herein are processes for preparing an ?,?-Cn-diol, wherein n is 5 or greater, from a feedstock comprising a Cn oxygenate. In one embodiment, the process comprises contacting the feedstock with hydrogen gas in the presence of a catalyst comprising a first metal component comprising Ni, Ir, Pt, Rh, Ru, Pd, Fe, Ag, or Au; a heteropoly acid component comprising H3[P(W3O10)4], H4[Si(W3O10)4], H4[P(Mo3O10)4], H4[Si(Mo3O10)4], Cs2.5H0.5[P(W3O10)4]Cs2.5H0.5[Si(W3O10)4], or mixtures thereof; optionally a second metal component comprising Cr, a Cr oxide, Ni, a Ni oxide, Fe, a Fe oxide, Co, a Co oxide, Mn, a Mn oxide, Mo, a Mo oxide, W, a W oxide, Re, a Re oxide, Zn, a Zn oxide, SiO2, or Al2O3; optionally at least one promoter comprising Na, K, Mg, Rb, Cs, Ca, Sr, Ba, Ce, or mixtures thereof; and optionally a support.
    Type: Grant
    Filed: April 25, 2013
    Date of Patent: September 30, 2014
    Assignee: E I du Pont de Nemours and Company
    Inventors: Alan Martin Allgeier, Wathudura Indika Namal De Silva, Carl Andrew Menning, Joachim C Ritter, Sourav Kumar Sengupta
  • Patent number: 8846984
    Abstract: Disclosed herein are processes for preparing an ?,?-Cn-diol, wherein n is 5 or greater, from a feedstock comprising a Cn oxygenate. In one embodiment, the process comprises contacting the feedstock with hydrogen gas in the presence of a catalyst comprising Cu, a Cu oxide, or mixtures thereof; a heteropoly acid component comprising H3[P(W3O10)4], H4[Si(W3O10)4], H4[P(Mo3O10)4], H4[Si(Mo3O10)4], Cs2.5H0.5[P(W3O10)4], Cs2.5H0.5[Si(W3O10)4], or mixtures thereof; optionally a second metal component comprising Cr, a Cr oxide, Ni, a Ni oxide, Mn, a Mn oxide, Fe, an Fe oxide, Co, a Co oxide, Mo, a Mo oxide, W, a W oxide, Re, a Re oxide, Zn, or a Zn oxide, Ag, a Ag oxide, SiO2, or Al2O3; optionally at least one promoter comprising Na, K, Mg, Rb, Cs, Ca, Sr, Ba, Ce, or mixtures thereof; and optionally a support.
    Type: Grant
    Filed: April 25, 2013
    Date of Patent: September 30, 2014
    Assignee: E I du Pont de Nemours and Company
    Inventors: Alan Martin Allgeier, Wathudura Indika Namal De Silva, Carl Menning, Joseph E Murphy, Joachim C Ritter, Sourav Kumar Sengupta
  • Patent number: 8785693
    Abstract: Process for the preparation of primary amines which have at least one functional group of the formula (—CH2—NH2) by alcohol amination of starting materials which have at least one functional group of the formula (—CH2—OH), with ammonia, with the elimination of water, where the alcohol amination is carried out under homogeneous catalysis in the presence of at least one complex catalyst which comprises at least one element selected from groups 8 and 9 of the Periodic Table of the Elements, and also at least one phosphorus donor ligand of the general formula (I).
    Type: Grant
    Filed: March 8, 2012
    Date of Patent: July 22, 2014
    Assignee: BASF SE
    Inventors: Thomas Schaub, Boris Buschhaus, Marion Kristina Brinks, Mathias Schelwies, Rocco Paciello, Johann-Peter Melder, Martin Merger
  • Patent number: 8766009
    Abstract: A process for preparing ethylamines and monoisopropylamine (MIPA), in which bioethanol is reacted with ammonia in the presence of hydrogen and of a heterogeneous catalyst to give ethylamines, said bioethanol having a content of sulfur and/or sulfur compounds of ?0.1 ppm by weight (calculated S), and then isopropanol is reacted with ammonia in the presence of the same catalyst and in the presence of hydrogen to give MIPA.
    Type: Grant
    Filed: November 20, 2012
    Date of Patent: July 1, 2014
    Assignee: BASF SE
    Inventors: Norbert Asprion, Manfred Julius, Oliver Bey, Stefanie Werland, Frank Stein, Matthias Kummer, Wolfgang Mägerlein, Johann-Peter Melder, Kevin Huyghe, Maarten Moors
  • Publication number: 20140179953
    Abstract: The present invention relates to a process to prepare ethylene amines by the amination of ethylene oxide, ethylene glycol or ethanolamine in the presence of a catalyst, comprising a step wherein methylamine and/or ethylamine are removed from the reaction effluents.
    Type: Application
    Filed: September 27, 2013
    Publication date: June 26, 2014
    Applicant: Akzo Nobel N.V.
    Inventors: Martin Stefan HANSON, Leif Kenny Christian GUSTAFSON, Johan LIF, Boris KUZMANOVIC, Ulf SCHRÖDER
  • Patent number: 8697930
    Abstract: Convert a methylamine (e.g. monomethylamine, dimethylamine and trimethylamine) to a mixture of olefins (e.g. ethylene, propylene and butylene) by placing the methylamine, optionally in a mixture with at least one of ammonia and an inert diluent, in contact with a microporous acidic silicoaluminophosphate catalyst or a microporous aluminosilicate catalyst.
    Type: Grant
    Filed: May 31, 2011
    Date of Patent: April 15, 2014
    Assignee: Dow Global Technologies LLC
    Inventors: Robert G. Bowman, Eric E. Stangland, Rainer Bruening, Angelika Heilmann, Roland Wagner, Jason Lee Bronkema
  • Patent number: 8664445
    Abstract: A method for providing a secondary or tertiary amine with formula (R1R2NR3)2NR4 is provided, wherein each of R1 and R2 are chosen from the group consisting of a methyl group, an ethyl group, an iso-propyl group and an n-propyl group; R3 being an alkoxyalkyl group chosen from the group consisting of —CH2CH2OCH2CH2-, —CH2CH2OCH2CH2CH2- and —CH2CH2CH2OCH2CH2CH2-; R4 is chosen from the group consisting of a hydrogen, a methyl group, an ethyl group, an iso-propyl group, an n-propyl group and a group with formula R1R2NR3. The method comprises the steps: (?)reacting R1R2NR3(OH) with ammonia, thereby providing a mixture comprising (R1R2NR3)2NR4; (?) separating (R1R2NR3)2NR4 from said mixture.
    Type: Grant
    Filed: May 6, 2010
    Date of Patent: March 4, 2014
    Assignees: Huntsman International LLC, Huntsman Corporation Hungary ZRT
    Inventors: Zsolt Gaspar, Heiko H. Humbert, Gabor Felber, Attila Gaspar, Robert A. Grigsby, Jr., Imre Kordas, Petra Emma Vanderstraeten
  • Patent number: 8637709
    Abstract: Preparing a primary amine by alcohol amination of alcohol with ammonia and elimination of water includes reacting, in a homogeneously catalyzed reaction, a mixture of alcohol, ammonia, nonpolar solvent, and catalyst, in a liquid phase, to obtain a product mixture. The process then includes phase separating the product mixture into a polar product phase and a nonpolar product phase, and separating off the nonpolar product phase. At least some of the nonpolar phase returns to the homogenously catalyzed reaction. The process further includes separating off amination product from the polar product phase. At least some of the catalyst is in the nonpolar phase, and the catalyst accumulates in the nonpolar phase.
    Type: Grant
    Filed: March 8, 2012
    Date of Patent: January 28, 2014
    Assignee: BASF SE
    Inventors: Thomas Schaub, Boris Buschhaus, Marion Kristina Brinks, Mathias Schelwies, Rocco Paciello, Johann-Peter Melder, Martin Merger
  • Publication number: 20130331573
    Abstract: Process for preparing piperazine of the formula I by reacting diethanolamine (DEOA) of the formula II with ammonia in the presence of hydrogen and a supported, metal-containing catalyst has been found, wherein the catalytically active mass of the catalyst, prior to its reduction with hydrogen, comprises oxygen-containing compounds of aluminum, copper, nickel and cobalt and in the range from 0.2 to 5.0% by weight of oxygen-containing compounds of tin, calculated as SnO, and the reaction is carried out in the liquid phase at an absolute pressure in the range from 160 to 220 bar, a temperature in the range from 180 to 220° C., using ammonia in a molar ratio to DEOA used of from 5 to 25 and in the presence of 0.2 to 9.0% by weight of hydrogen, based on the total amount of DEOA used and ammonia.
    Type: Application
    Filed: June 5, 2013
    Publication date: December 12, 2013
    Inventors: Roland Bou Chedid, Johann-Peter Melder, Ulrich Abel, Roman Dostalek, Nina Challand, Bernd Stein, Michael Jödecke
  • 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
  • Publication number: 20130289310
    Abstract: The present invention discloses the method for producing a tertiary amine, using the column reactor packed with catalyst layers, containing supplying a liquid and a gaseous raw materials from the bottom of the column, reacting these raw materials in the column, and discharging the product from the top of the column, wherein the column reactor includes two or more honeycomb catalyst layers as the catalyst layers, one or more spaces between each honeycomb catalyst layer, and one or more rectifying sections that prevents a partial or whole back flow of the raw materials, arranged in each space without contacting with the honeycomb catalyst layer.
    Type: Application
    Filed: December 19, 2011
    Publication date: October 31, 2013
    Applicant: KAO CORPORATION
    Inventors: Yasumitsu Sakuma, Wataru Nomura, Goshi Yamamoto, Takeshi Narushima
  • Publication number: 20130289309
    Abstract: The present invention relates to a process for producing a tertiary amine, including the following steps (1) and (2): Step (1); introducing an alcohol having 1 to 36 carbon atoms and a raw amine represented by the following general formula (I) into a first reaction vessel to react with each other in the presence of a catalyst and hydrogen, and then continuing the reaction while discharging water produced in the reaction and a hydrogen-containing gas out of a reaction system in the first reaction vessel: R1R2NH??(I) wherein R1 and R2 are each independently a hydrogen atom or a hydrocarbon group having 1 to 36 carbon atoms; and Step (2): introducing the hydrogen-containing gas discharged from the first reaction vessel into a second reaction vessel to reduce an amount of carbon monoxide contained in the hydrogen-containing gas, and then introducing a part or whole of the hydrogen-containing gas into the first reaction vessel.
    Type: Application
    Filed: December 27, 2011
    Publication date: October 31, 2013
    Applicant: KAO CORPORATION
    Inventors: Masahiko Watanabe, Gosuke Tateno, Hirofumi Mizukoshi
  • Patent number: 8563778
    Abstract: The present invention relates to a process to prepare ethylene amines by the amination of ethylene oxide, ethylene glycol or ethanolamine in the presence of a catalyst, comprising a step wherein methylamine and/or ethylamine are removed from the reaction effluents.
    Type: Grant
    Filed: December 29, 2008
    Date of Patent: October 22, 2013
    Assignee: Akzo Nobel N.V.
    Inventors: Martin Stefan Hanson, Leif Kenny Christian Gustafson, Johan Lif, Boris Kuzmanovic, Ulf Schröder
  • Publication number: 20130231505
    Abstract: Disclosed are processes for preparing 1,6-hexanediol from levoglucosenone. In one embodiment, the process comprises contacting levoglucosenone with hydrogen in the presence of a hydrogenation catalyst comprising palladium, platinum/tungsten, nickel/tungsten, rhodium/rhenium, or mixtures thereof at a first temperature between about 50° C. and 100° C. and at a first reaction pressure between about 50 psi and 2000 psi for a first reaction period, and at a second temperature between about 120° C. and 250° C. and at a second pressure between about 500 psi and 2000 psi for a second reaction period to form a product mixture comprising 1,6-hexanediol, wherein the first reaction period is the amount of time in which the levoglucosenone has a conversion of at least about 95%. In one embodiment, the 1,6-hexanediol is converted to 1,6-diaminohexane.
    Type: Application
    Filed: April 25, 2013
    Publication date: September 5, 2013
    Applicant: E I DU PONT DE NEMOURS AND COMPANY
    Inventors: Alan Martin Allgeier, Joachim C. Ritter, Sourav Kumar Sengupta
  • Patent number: 8519191
    Abstract: A synthesis method of 3-methylamino-1,2-propanediol is disclosed in the invention, and it includes the following steps: (a) adding glycerin chlorohydrin, aqueous monomethylamine solution and an amination catalyst, namely NaOH solution and NaHCO3, into a reactor, mixing the material sufficiently, and allowing amination reaction to proceed in two temperature stages; (b) removing monomethylamine and water from the amination solution after the amination reaction is completed, filtering out the solid resultant, and feeding the filtrate into a still; (c) distilling under reduced pressure to obtain 3-methylamino-1,2-propanediol, wherein the vacuum for distillation under reduced pressure is equal to or greater than 0.099 MPa and the temperature is 130-160° C.
    Type: Grant
    Filed: March 12, 2010
    Date of Patent: August 27, 2013
    Assignee: Weifang PBNS Chem. Industry Co., Ltd
    Inventors: Zhongfa Zhang, Xueyang Guo, Hui Huang
  • Publication number: 20130204037
    Abstract: A catalytic process is taught for non-oxidative alkylation of organic compounds, comprising alcohols, alkanes, glycols, ethers, aldehydes, ketones, carboxylic acids, esters, amines, thiols or phosphines, by alkyl groups produced from alcohols or glycols, forming products comprising ethers and other higher molecular weight alkylated compounds. The process is conducted at a reflux temperature below 200° C. in the presence of an acid, alkali or neutral salt dehydrating agent comprising sulfuric acid, phosphoric acid or their salts, lime or anhydrous calcium sulfate in the absence of zero valent metals and air. Specifically, this catalytic process converts ethanol to ethyl butyl ethers, ethyl hexyl ethers and dibutyl ethers or oxygenated gasoline as well as amines comprising n-butyl amine plus butanol to dibutyl amine and butyl hexyl amines at ambient pressure.
    Type: Application
    Filed: February 7, 2012
    Publication date: August 8, 2013
    Applicant: Carter Technologies
    Inventor: Melvin Keith Carter
  • Patent number: 8487135
    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: Grant
    Filed: December 2, 2010
    Date of Patent: July 16, 2013
    Assignee: BASF SE
    Inventors: Petr Kubanek, Wolfgang Mägerlein, Johann-Peter Melder, Thomas Heidemann
  • Patent number: 8486183
    Abstract: An acid gas absorbent comprising an alkylamino alkyloxy (alcohol) monoalkyl ether and a process for the selective removal Of H2S from gaseous mixtures containing H2S and CO2 using an absorbent solution comprising an alkylamino alkyloxy alcohol monoalkyl ether.
    Type: Grant
    Filed: July 21, 2006
    Date of Patent: July 16, 2013
    Assignee: ExxonMobil Research and Engineering Company
    Inventors: Michael Siskin, Edmund John Mozeleski, Robert Basil Fedich, Frank Cheng-Yu Wang
  • Publication number: 20130178656
    Abstract: The present application relates to a process for preparing secondary amines by aminating excess primary or secondary alcohols with primary amines in the liquid phase in the presence of copper-comprising catalysts.
    Type: Application
    Filed: January 9, 2013
    Publication date: July 11, 2013
    Inventors: Christof Wilhelm Wigbers, Johann-Peter Melder, Bernd Stein
  • Patent number: 8481787
    Abstract: The present invention provides a method for producing a tertiary amine by using a secondary amine and an alcohol as starting materials to obtain a corresponding tertiary amine. The method of the present invention includes reacting a secondary amine with an alcohol in the presence of a catalyst, wherein the catalyst is previously used in the reaction of a primary amine with an alcohol to obtain a tertiary amine.
    Type: Grant
    Filed: December 20, 2010
    Date of Patent: July 9, 2013
    Assignee: Kao Corporation
    Inventors: Toru Nishimura, Wataru Nomura, Yushin Takahashi
  • Patent number: 8471065
    Abstract: In another exemplary embodiment, an amine functional curing agent has an Amine Hydrogen Functionality (AHF) of at least 7 and an Amine-Hydrogen Equivalent Weight (AHEW) of at least about 50.
    Type: Grant
    Filed: March 26, 2012
    Date of Patent: June 25, 2013
    Assignee: Huntsman Petrochemical LLC
    Inventors: Bruce L. Burton, Terry L. Renken
  • Patent number: 8466322
    Abstract: Process for preparing tri-n-propylamine (TPA), wherein di-n-propylamine (DPA) is reacted in the presence of hydrogen and a copper-comprising heterogeneous catalyst. An integrated process for preparing TPA, which comprises the following operations: I) reaction of n-propanol with ammonia in a reactor in the presence of an amination catalyst and optionally hydrogen to form a mixture of mono-n-propylamine, DPA and TPA, II) separation of unreacted ammonia, unreacted n-propanol and possibly hydrogen from the reaction product mixture and recirculation of at least the ammonia and propanol to the reactor in I) and also separation of the n-propylamine mixture by distillation and isolation of the TPA, III) reaction of the DPA obtained in the separation by distillation in II) in a reactor in the presence of hydrogen and a copper-comprising heterogeneous catalyst to form TPA and IV) feeding of the reactor output from III) to operation II).
    Type: Grant
    Filed: June 30, 2011
    Date of Patent: June 18, 2013
    Assignee: BASF SE
    Inventors: Kevin Huyghe, Steven Brughmans, Falk Simon, Johann-Peter Melder, Peter Raatz
  • Patent number: 8455693
    Abstract: A process for preparing 2-(2-tert-butylaminoethoxy)ethanol (tert-butylaminodiglycol, TBADG) by reacting diethylene glycol (DG) with tert-butylamine (TBA) in the presence of hydrogen and of a copper catalyst, by effecting the reaction at a temperature in the range from 160 to 220° C. in the presence of a copper- and aluminum oxide-containing catalyst, where the catalytically active material of the catalyst, before the reduction thereof with hydrogen, comprises 20 to 75% by weight of aluminum oxide (Al2O3), 20 to 75% by weight of oxygen compounds of copper, calculated as CuO, and ?5% by weight of oxygen compounds of nickel, calculated as NiO.
    Type: Grant
    Filed: May 20, 2011
    Date of Patent: June 4, 2013
    Assignee: BASF SE
    Inventors: Roland Bou Chedid, Johann-Peter Melder, Steven Brughmans, Torsten Katz
  • 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
  • Publication number: 20130131385
    Abstract: A process for preparing ethylamines and monoisopropylamine (MIPA), in which bioethanol is reacted with ammonia in the presence of hydrogen and of a heterogeneous catalyst to give ethylamines, said bioethanol having a content of sulfur and/or sulfur compounds of ?0.1 ppm by weight (calculated S), and then isopropanol is reacted with ammonia in the presence of the same catalyst and in the presence of hydrogen to give MIPA.
    Type: Application
    Filed: November 20, 2012
    Publication date: May 23, 2013
    Applicant: BASF SE
    Inventor: BASF SE
  • Patent number: 8338647
    Abstract: The present invention provides a method for producing a tertiary amine by reacting an alcohol with a primary or secondary amine in the presence of a film catalyst containing a thermosetting resin and an active metal, wherein the film catalyst is reduced at 100 to 150° C., and a method for activating the film catalyst containing a thermosetting resin and an active metal, including applying a coating agent containing the thermosetting resin and a powder catalyst onto the surface of a support, drying the resultant, curing it at 80 to 170° C., and reducing the catalyst at 100 to 150° C.
    Type: Grant
    Filed: September 18, 2008
    Date of Patent: December 25, 2012
    Assignee: Kao Corporation
    Inventors: Wataru Nomura, Shoji Hasegawa
  • Patent number: 8324430
    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: Grant
    Filed: December 10, 2008
    Date of Patent: December 4, 2012
    Assignee: BASF SE
    Inventors: Petr Kubanek, Wolfgang Mägerlein, Ekkehard Schwab, Johann-Peter Melder, Manfred Julius
  • Patent number: 8318982
    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, of cobalt and of tin, and in the range from 0.2 to 5.0% by weight of oxygen compounds of yttrium, of lanthanum, of cerium and/or of hafnium, each calculated as Y2O3, La2O3, Ce2O3 and Hf2O3 respectively, and catalysts as defined above.
    Type: Grant
    Filed: December 2, 2010
    Date of Patent: November 27, 2012
    Assignee: BASF SE
    Inventors: Petr Kubanek, Wolfgang Mägerlein, Johann-Peter Melder, Thomas Heidemann
  • Patent number: 8293075
    Abstract: Processes for the continuous fractional distillation of a mixture containing morpholine (MO), monoaminodiglycol (ADG), ammonia and water from a reaction of diethylene glycol (DEG) with ammonia, the process including: (i) separating off ammonia from the mixture at a top of a first distillation column K10; (ii) feeding a bottom fraction from K10 to a second distillation column K20, in which water and an organic product are separated off at the top at a temperature at the top in the range from 45 to 198° C. and a pressure in the range from 0.
    Type: Grant
    Filed: September 12, 2007
    Date of Patent: October 23, 2012
    Assignee: BASF SE
    Inventors: Helmut Schmidtke, Oliver Buβmann, Ralph Versch, Udo Rheude, Uwe Leyk, Manfred Julius, Martin Rudloff, Erhard Henkes
  • Patent number: 8293945
    Abstract: Processes for preparing an amine, which processes comprise: 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-and nickel-containing catalyst; wherein the catalyst comprises a catalytically active composition which comprises, before reduction with hydrogen, oxygen compounds of zirconium, nickel, and iron, and 0.2 to 5.5% by weight of at least one oxygen compound of tin, lead, bismuth, molybdenum, antimony or phosphorus, calculated as SnO, PbO, Bi2O3, MoO3, Sb2O3 and H3PO4 respectively; and wherein the catalytically active composition of the catalyst does not comprise any copper.
    Type: Grant
    Filed: December 10, 2008
    Date of Patent: October 23, 2012
    Assignee: BASF SE
    Inventors: Petr Kubanek, Wolfgang Mägerlein, Ekkehard Schwab, Johann-Peter Melder, Manfred Julius
  • Patent number: 8293944
    Abstract: A reaction apparatus which is used for conducting a gas-liquid chemical reaction in a state that a liquid is in a continuous phase, wherein its reactor has therein a shear type stirring impeller for dispersing a raw reaction gas or a carrier gas and a film-formed catalyst, which apparatus is capable of producing a target reaction product; and a process for producing a tertiary amine in such reaction apparatus.
    Type: Grant
    Filed: January 19, 2012
    Date of Patent: October 23, 2012
    Assignee: Kao Corporation
    Inventors: Atsushi Hirota, Toru Nishimura