By Transamination Patents (Class 564/470)
  • Patent number: 11884609
    Abstract: The present disclosure pertains to a process for manufacturing ethyleneamine compounds selected from the group of ethyleneamines and hydroxyethylethyleneamines wherein the process comprises two reaction sequences.
    Type: Grant
    Filed: February 13, 2020
    Date of Patent: January 30, 2024
    Assignee: NOURYON CHEMICALS INTERNATIONAL B.V.
    Inventors: Rolf Krister Edvinsson, Antoon Jacob Berend Ten Kate, Michiel Jozef Thomas Raaijmakers, Rens Veneman, Slavisa Jovic, Lawien Feisal Zubeir, Eike Nicolas Kantzer, Ina Ehlers, Hendrik Van Dam, Karl Fredrik Lake
  • Patent number: 11878954
    Abstract: Process for manufacturing ethyleneamine compounds selected from the group of ethyleneamines and hydroxyethylethyleneamines wherein the process comprises two reaction sequences.
    Type: Grant
    Filed: February 13, 2020
    Date of Patent: January 23, 2024
    Assignee: NOURYON CHEMICALS INTERNATIONAL B.V.
    Inventors: Antoon Jacob Berend Ten Kate, Rolf Krister Edvinsson, Michiel Jozef Thomas Raaijmakers, Rens Veneman, Slavisa Jovic, Lawien Zubeir, Eike Nicolas Kantzer, Ina Ehlers, Hendrik Van Dam, Karl Fredrik Lake
  • Patent number: 9783486
    Abstract: A process for preparing high molecular weight, branched, acyclic polyalkyleneamines comprising transaminating a reaction mixture that includes at least a first polyalkyleneamine component that contains at least two non-tertiary amine groups separated from one another by a ternary or higher carbon atom and a second polyalkyleneamine component having the formula wherein x, y, and z are the same or different and are integers of from 1 to 10; a, b, c, d, e, and f are the same or different and are H or hydrocarbyl of from 1 to 10 carbon atoms; A, B, C, D, E, are the same or different and are H or hydrocarbyl of from 1 to 10 carbon atoms; provided that at least two of the amine groups are primary or secondary.
    Type: Grant
    Filed: November 24, 2014
    Date of Patent: October 10, 2017
    Assignee: DOW GLOBAL TECHNOLOGIES LLC
    Inventors: Stephen W. King, Sadeka Onam
  • Patent number: 9365492
    Abstract: The present invention relates to a production method for 2-(ethylamino)ethanol, including subjecting N-ethyldiethanolamine to a disproportionation reaction in the presence of at least one kind of catalyst selected from the group consisting of a manganese oxide catalyst and an alkali metal hydroxide-supporting zirconium oxide catalyst. According to the present invention, 2-(ethylamino)ethanol can be obtained by subjecting N-ethyldiethanolamine to the disproportionation reaction. 2-(Ethylamino)ethanol is a useful compound to be used in various applications such as a drug, an agricultural chemical, and a functional chemical.
    Type: Grant
    Filed: October 2, 2013
    Date of Patent: June 14, 2016
    Assignee: KOEI CHEMICAL COMPANY, LIMITED
    Inventors: Hidetaka Shimazu, Tsuyoshi Tagata
  • Patent number: 9000217
    Abstract: A process for preparing high molecular weight acyclic polyamines comprising providing a reaction mixture that includes at least a first component comprising a first organic, nitrogen-containing compound that contains at least two non-tertiary amine groups separated from one another by a ternary or higher carbon atom spacing that can be transaminated in the presence of a hydrogenation/dehydrogenation catalyst to form a mixture of higher molecular weight, acyclic polyamines while minimizing the formation of cyclic polyamines.
    Type: Grant
    Filed: October 20, 2011
    Date of Patent: April 7, 2015
    Assignee: DOW Global Technologies LLC
    Inventor: Stephen W. King
  • Patent number: 8993759
    Abstract: A transamination process is described to prepare polyamine product mixtures from reactants comprising mixed nitrogen-containing compounds with binary carbon spacing between nitrogen-containing groups (a binary component). A second nitrogen-containing component with a second carbon atom spacing between nitrogen-containing groups may also be employed. The molar ratio between the binary and second components can be adjusted to customize the product composition for desired end uses.
    Type: Grant
    Filed: October 20, 2011
    Date of Patent: March 31, 2015
    Assignee: DOW Global Technologies LLC
    Inventor: Stephen W. King
  • Patent number: 8987518
    Abstract: The present invention relates to polyamines and to a process for preparing polyamines.
    Type: Grant
    Filed: February 26, 2014
    Date of Patent: March 24, 2015
    Assignee: BASF SE
    Inventors: Ansgar Gereon Altenhoff, Christoph Mueller, Christian Mueller, Andreas Kunst, Thomas Reissner, Kirsten Dahmen
  • Publication number: 20140039181
    Abstract: The invention relates to a method for producing a N-substituted amine compound by catalyzed alkylation. The method uses amine and alcohol or two kinds of amines as the reaction materials, employs composite metal oxides catalyst at a reaction temperature of 80-180° C. to catalyze the reaction for 6-36 hours, so as to produce the N-substituted amine compound. The reaction condition of the method of the invention is relatively moderate, using a catalyst made of cheap non-noble metals, which is non-caustic and easy to be separated and reused. The reaction does not need any medium and has relatively high conversion rate and selectivity.
    Type: Application
    Filed: December 28, 2012
    Publication date: February 6, 2014
    Applicant: Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences
    Inventor: Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences
  • Patent number: 8642810
    Abstract: Process for the direct amination of hydrocarbons to aminohydrocarbons by reaction of a feed stream E comprising at least one hydrocarbon and at least one aminating reagent to form a reaction mixture R comprising aminohydrocarbon and hydrogen in a reaction zone RZ and electrochemical separation of at least part of the hydrogen formed in the reaction from the reaction mixture R by means of a gastight membrane-electrode assembly having at least one selectively proton-conducting membrane and at least one electrode catalyst on each side of the membrane, where at least part of the hydrogen is oxidized to protons at the anode catalyst on the retentate side of the membrane and the protons pass through the membrane and on the permeate side are reacted with oxygen to form water, where the oxygen originates from an oxygen-comprising stream O which is brought into contact with the permeate side of the membrane, over the cathode catalyst.
    Type: Grant
    Filed: July 7, 2010
    Date of Patent: February 4, 2014
    Assignee: BASF SE
    Inventors: Petr Kubanek, Alexander Panchenko, Andreas Fischer, Thomas Heidemann
  • Patent number: 8604248
    Abstract: The present invention provides catalyst compositions useful for transamination reactions. The catalyst compositions have a catalyst support that includes transitional alumina, use a low metal loading (for example, less than 25 wt. %), and do not require the presence of rhenium. The catalyst compositions are able to advantageously promote transamination of a reactant product (such as the transamination of EDA to DETA) with excellent activity and selectivity, and similar to transaminations promoted using a precious metal-containing catalyst.
    Type: Grant
    Filed: September 20, 2012
    Date of Patent: December 10, 2013
    Assignee: Union Carbide Chemicals & Plastics Technolgy LLC
    Inventors: Stephen W. King, Stefan K. Mierau
  • Patent number: 8580990
    Abstract: Methods are provided for the catalytic hydroamination of compounds having an alkyne or allene functional group, in which the compound is contacted with ammonia or an amine in the presence of a catalytic amount of a gold complex under conditions sufficient for hydroamination to occur.
    Type: Grant
    Filed: May 8, 2009
    Date of Patent: November 12, 2013
    Assignee: The Regents of the University of California
    Inventors: Guy Bertrand, Vincent Lavallo, Guido D. Frey, Bruno Donnadieu, Michele Soleilhavoup
  • Publication number: 20130225864
    Abstract: A process for preparing high molecular weight acyclic polyamines comprising providing a reaction mixture that includes at least a first component comprising a first organic, nitrogen-containing compound that contains at least two non-tertiary amine groups separated from one another by a ternary or higher carbon atom spacing that can be transaminated in the presence of a hydrogenation/dehydrogenation catalyst to form a mixture of higher molecular weight, acyclic polyamines while minimizing the formation of cyclic polyamines.
    Type: Application
    Filed: October 20, 2011
    Publication date: August 29, 2013
    Inventor: Stephen W. King
  • Patent number: 8492592
    Abstract: The invention provides a method of transaminating a reactant with a catalyst composition comprising support and catalyst portions. The support includes an acidic mixed metal oxide including a transitional alumina and a second metal oxide. The transitional alumina can comprise delta or theta alumina, in combination with other transitional phases, or an alpha or gamma alumina. The second metal oxide has a weight percentage less than the weight percentage of alumina. The catalyst portion is 25 weight percent or less of the catalyst composition and is composed of nickel and rhenium. The catalyst portion includes nickel in an amount in the range of 2 to 20 weight percent, based upon total catalyst composition weight, and there is no boron in the catalyst portion. The method provides high activity and selectivity for reactant transamination to a desired product while minimizing the formation of unwanted cyclic products.
    Type: Grant
    Filed: April 26, 2012
    Date of Patent: July 23, 2013
    Assignee: Union Carbide Chemicals & Plastics Technology LLC
    Inventors: Stephen W. King, Stefan K. Mierau
  • Patent number: 8383860
    Abstract: The present invention reacts ethylenediamine with one or more additional ethyleneamines in the presence of a transamination catalyst to provide a different, preferably more desirable product mix of one or more ethyleneamines.
    Type: Grant
    Filed: October 6, 2009
    Date of Patent: February 26, 2013
    Assignee: Union Carbide Chemicals & Plastics Technology LLC
    Inventors: Ronald G. Cook, Stephen W. King, David M. Petraitis, Thomas Z. Smak
  • Publication number: 20130023698
    Abstract: The present invention provides catalyst compositions useful for transamination reactions. The catalyst compositions have a catalyst support that includes transitional alumina, use a low metal loading (for example, less than 25 wt. %), and do not require the presence of rhenium. The catalyst compositions are able to advantageously promote transamination of a reactant product (such as the transamination of EDA to DETA) with excellent activity and selectivity, and similar to transaminations promoted using a precious metal-containing catalyst.
    Type: Application
    Filed: September 20, 2012
    Publication date: January 24, 2013
    Applicant: UNION CARBIDE CHEMICALS & PLASTICS TECHNOLOGY LLC
    Inventor: Union Carbide Chemicals & Plastics Technology
  • Patent number: 8293202
    Abstract: This idea relates to the use of polyalkylene glycols and non-salt polyether amines to improve the effectiveness of silica removal by coagulation and agglomeration of colloidal silica particles in aqueous mineral process streams.
    Type: Grant
    Filed: October 3, 2008
    Date of Patent: October 23, 2012
    Assignee: Huntsman Corporation Australia Pty Limited
    Inventor: Salvatore Lazzaro
  • Publication number: 20120238780
    Abstract: The invention provides a method of transaminating a reactant with a catalyst composition comprising support and catalyst portions. The support includes an acidic mixed metal oxide including a transitional alumina and a second metal oxide. The transitional alumina can comprise delta or theta alumina, in combination with other transitional phases, or an alpha or gamma alumina. The second metal oxide has a weight percentage less than the weight percentage of alumina. The catalyst portion is 25 weight percent or less of the catalyst composition and is composed of nickel and rhenium. The catalyst portion includes nickel in an amount in the range of 2 to 20 weight percent, based upon total catalyst composition weight, and there is no boron in the catalyst portion. The method provides high activity and selectivity for reactant transamination to a desired product while minimizing the formation of unwanted cyclic products.
    Type: Application
    Filed: April 26, 2012
    Publication date: September 20, 2012
    Inventors: Stephen W. King, Stefan K. Mierau
  • Patent number: 8232223
    Abstract: The present invention relates to a method for recovering N,N,N?-trimethylbisaminoethylether from a mixture with its amide and a method for separating N,N,N?-trimethylbisaminoethylether from mixtures comprising tertiary amines or tertiary aminoalkylether as well as a composition comprising a mixture of N,N,N?-trimethylbisaminoethylether and a transamidation agent.
    Type: Grant
    Filed: May 1, 2008
    Date of Patent: July 31, 2012
    Assignees: Huntsman International LLC, Huntsman Corporation Hungary ZRT
    Inventors: Imre Kordas, Heiko H. Humbert, Gabor Felber, Attila Gaspar, Robert A. Grigsby, Jr., Petra E. Vanderstraeten
  • Patent number: 8188318
    Abstract: The present invention provides methods of manufacturing ethyleneamines that makes use of an ethyleneamine-generating process that is coupled to a transamination process. The combination of an ethyleneamine-generating process with a transamination process improves the mix flexibility that can be obtained from the single process allowing the production of ethyleneamine compositions having an improved and more desirable product mix.
    Type: Grant
    Filed: October 6, 2009
    Date of Patent: May 29, 2012
    Assignee: Union Carbide Chemicals & Plastics Technology LLC
    Inventors: David M. Petraitis, Stephen W. King, Thomas Z. Srnak
  • Patent number: 8124808
    Abstract: A method of transalkoxylation of nucleophilic compounds in which an alkoxylated and a nucleophilic compound are combined in a suitable vessel and reacted in the presence of a heterogeneous catalyst under conditions capable of transferring at least one hydroxyalkyl group from the alkoxylated compound to the nucleophilic compound. The method is especially useful in the transalkoxylation of alkanolamines to transfer a hydroxyalkyl group from an alkanolamine having a greater number of hydroxyalkyl groups to an alkanolamine having a lesser number of hydroxyalkyl groups.
    Type: Grant
    Filed: October 6, 2009
    Date of Patent: February 28, 2012
    Assignee: Union Carbide Chemicals & Plastics Technology LLC
    Inventors: Stephen W. King, William C. Hoffman
  • Publication number: 20100144517
    Abstract: The present invention relates to a method for recovering N,N,N?-trimethylbisaminoethylether from a mixture with its amide and a method for separating N,N,N?-trimethylbisaminoethylether from mixtures comprising tertiary amines or tertiary aminoalkylether as well as a composition comprising a mixture of N,N,N?-trimethylbisaminoethylether and a transamidation agent.
    Type: Application
    Filed: May 1, 2008
    Publication date: June 10, 2010
    Applicant: HUNTSMAN INTERNATIONAL LLC.
    Inventors: Imre Kordas, Heiko H. Humbert, Gabor Felber, Attila Gaspar, Robert A. Grigsby, JR., Petra Emma Vanderstraeten
  • Publication number: 20100137642
    Abstract: The present invention provides catalyst compositions useful for transamination reactions. The catalyst compositions have a catalyst support that includes transitional alumina, use a low metal loading (for example, less than 25 wt. %), and do not require the presence of rhenium. The catalyst compositions are able to advantageously promote transamination of a reactant product (such as the transamination of EDA to DETA) with excellent activity and selectivity, and similar to transaminations promoted using a precious metal-containing catalyst.
    Type: Application
    Filed: October 6, 2009
    Publication date: June 3, 2010
    Inventors: Stephen W. King, Stefan K. Mierau
  • Patent number: 7700805
    Abstract: An amine is prepared by cleaving a carbamate of the formula I wherein R1=hydrogen, alkyl, aryl or phenyl group, R2=alkyl, aryl or phenyl group, wherein R1 and R2 are independently substituted or unsubstituted, wherein the cleaving of the carbamate is performed in the presence of an acid of the formula II wherein R3, R4 and R5 are independently alkyl or phenyl group, wherein R1, R2, R3, R4 and R5 are the same or different.
    Type: Grant
    Filed: May 12, 2008
    Date of Patent: April 20, 2010
    Assignee: Evonik Degussa GmbH
    Inventors: Günther Köhler, Manfred Neumann, Marianne Omeis
  • Publication number: 20100087682
    Abstract: The invention provides a catalyst composition composed of a support portion and a catalyst portion. The support portion includes an acidic mixed metal oxide including a transitional alumina and a second metal oxide. The transitional alumina can comprise delta or theta alumina, in combination with other transitional phases, or an alpha or gamma alumina. The second metal oxide has a weight percentage that is less than the weight percentage of alumina. The catalyst portion is 25 weight percent or less of the catalyst composition and is composed of nickel and rhenium. The catalyst portion includes nickel in an amount in the range of 2 to 20 weight percent, based upon total catalyst composition weight, and there is no boron in the catalyst portion.
    Type: Application
    Filed: October 6, 2009
    Publication date: April 8, 2010
    Inventors: Stephen W. King, Stefan K. Mierau
  • Publication number: 20100087683
    Abstract: The present invention reacts ethylenediamine with one or more additional ethyleneamines in the presence of a transamination catalyst to provide a different, preferably more desirable product mix of one or more ethyleneamines.
    Type: Application
    Filed: October 6, 2009
    Publication date: April 8, 2010
    Inventors: Ronald G. Cook, Stephen W. King, David M. Petraitis, Thomas Z. Smak
  • Publication number: 20100087681
    Abstract: The present invention provides methods of manufacturing ethyleneamines that makes use of an ethyleneamine-generating process that is coupled to a transamination process. The combination of an ethyleneamine-generating process with a transamination process improves the mix flexibility that can be obtained from the single process allowing the production of ethyleneamine compositions having an improved and more desirable product mix.
    Type: Application
    Filed: October 6, 2009
    Publication date: April 8, 2010
    Inventors: David M. Petraitis, Stephen W. King, Thomas Z. Smak
  • Patent number: 7651968
    Abstract: A process for producing a shaped body comprising a microporous material and at least one silicon-comprising binder, which comprises the steps (I) preparation of a mixture comprising the microporous material, the binder and a lubricant, (II) mixing and densification of the mixture, (III) shaping of the densified mixture to give a shaped body and (IV) calcination of the shaped body, wherein a silicone resin having a softening point of ?30° C. is used as binder, shaped bodies which can be produced by this process, their use as catalyst, in particular in organic synthesis and very particularly preferably in a process for preparing methylamines.
    Type: Grant
    Filed: December 5, 2006
    Date of Patent: January 26, 2010
    Assignee: BASF SE
    Inventors: Marco Bosch, Jan Eberhardt, Roderich Röttger
  • Patent number: 7582583
    Abstract: Process for producing a shaped body comprising a microporous material and at least one silicon-containing binder, which comprises the steps (I) preparing a mixture comprising the microporous material, the binder, a make-up aid and a solvent, (II) mixing and densifying the mixture, (III) shaping the densified mixture to give a shaped body, (IV) drying the shaped body and (V) calcining the dried shaped body, wherein the binder used is an organosilicon compound, shaped bodies which can be produced by this process, their use as catalyst, in particular in organic synthesis and very particularly preferably in a process for preparing triethylenediamine (TEDA).
    Type: Grant
    Filed: June 10, 2005
    Date of Patent: September 1, 2009
    Assignee: BASF SE
    Inventors: Marco Bosch, Matthias Frauenkron, Milan Kostur, Otto Hofstadt
  • Patent number: 7393978
    Abstract: Process for the preparation of ethylenamines, in particular diethylenetriamine (DETA), by continuous reaction of ethylenediamine (EDA) in the presence of a heterogeneous catalyst, where the reaction is carried out in a reaction column.
    Type: Grant
    Filed: July 15, 2004
    Date of Patent: July 1, 2008
    Assignee: BASF Aktiengesellschaft
    Inventors: Matthias Frauenkron, Thomas Krug, Holger Evers, Johann-Peter Melder, Roderich Röttger, Markus Siegert, Till Gerlach, Jan Nouwen, Ellen Dahlhoff, Christian Miller
  • Patent number: 7227040
    Abstract: A branched composition can be formed by reacting a reagent containing a saturated hydrocarbon moiety in the presence of (a) a catalyst capable of activating a carbon-hydrogen bond therein and (b) a branching reagent having a moiety that binds to the carbon atom in the carbon-hydrogen bond upon extraction of the hydrogen atom from that carbon-hydrogen bond. Suitable catalysts are those that comprise a transition metal cation possessing multiple oxidation states that is embedded in an anion that is a transition metal oxide possessing a higher oxidation state for the metal therein than the metal in the cation.
    Type: Grant
    Filed: June 7, 2004
    Date of Patent: June 5, 2007
    Assignee: Akzo Nobel N.V.
    Inventors: Zongchao Zhang, Xiaolei Sun
  • Patent number: 7053247
    Abstract: The invention relates to a process for the manufacture of diethylenetriamine and higher polyethylenepolyamines by a transamination of ethylenediamine. The transamination is performed at a temperature from 135° C. to 180° C. at a pressure from 5 Mpa to 40 Mpa in the presence of hydrogen and a particulate catalysts containing 26 to 65% by weight of nickel on an oxide carrier. A high conversion degree of ethylenediamine and a high selectivity to form acyclic polyethylenepolyamines, such as diethylenetriamine are obtained by the process. The formation of cyclic amine compounds, e.g. piperazine, is low.
    Type: Grant
    Filed: July 5, 2002
    Date of Patent: May 30, 2006
    Assignee: Akzo Nobel N.V.
    Inventors: Johan Lif, Kristina Ekenberg
  • Patent number: 7053246
    Abstract: Process for preparing a symmetrical secondary amine by reaction of a primary amine in the presence of hydrogen and a catalyst whose preparation has involved precipitation of catalytically active components onto monoclinic, tetragonal or cubic zirconium dioxide.
    Type: Grant
    Filed: December 10, 2003
    Date of Patent: May 30, 2006
    Assignee: BASF Aktiengesellschaft
    Inventors: Till Gerlach, Frank Funke, Christoph Benisch, Johann-Peter Melder
  • Publication number: 20040220428
    Abstract: Process for preparing a symmetrical secondary amine by reaction of a primary amine in the presence of hydrogen and a catalyst whose preparation has involved precipitation of catalytically active components onto monoclinic, tetragonal or cubic zirconium dioxide.
    Type: Application
    Filed: December 10, 2003
    Publication date: November 4, 2004
    Inventors: Till Gerlach, Frank Funke, Christoph Benisch, Johann-Peter Melder
  • Publication number: 20040171884
    Abstract: The invention relates to a process for the manufacture of diethylenetriamine and higher polyethylenepolyamines by a transamination of ethylenediamine. The transamination is performed at a temperature from 135° C. to 180° C. at a pressure from 5 Mpa to 40 Mpa in the presence of hydrogen and a particulate catalysts containing 26 to 65% by weight of nickel on an oxide carrier. A high conversion degree of ethylenediamine and a high selectivity to form acyclic polyethylenepolyamines, such as diethylenetriamine are obtained by the process. The formation of cyclic amine compounds, e.g. piperazine, is low.
    Type: Application
    Filed: January 21, 2004
    Publication date: September 2, 2004
    Inventors: Johan Lif, Kristina Ekenberg
  • Patent number: 6576796
    Abstract: Preparation of alkylamines, where, in a first process stage, an olefin is reacted with ammonia, a primary amine and/or a secondary amine under hydroaminating conditions, and then, in a second process stage, the resulting hydroamination product(s) is/are reacted under transalkylating conditions.
    Type: Grant
    Filed: September 25, 2000
    Date of Patent: June 10, 2003
    Assignee: BASF Aktiengesellschaft
    Inventors: Frank Funke, Ulrich Steinbrenner, Matthias Frauenkron, Ralf Böhling, Johann-Peter Melder, Thomas Heidemann
  • Patent number: 6492558
    Abstract: Process for the preparation of n-butylamines where n-butenylamines are firstly prepared by reacting 1,3-butadiene in the form of a 1,3-butadiene containing mixture obtained during the cracking of petroleum fractions or during the dehydrogenation of LPG or LNG or from GTL technology with a primary amine and/or a secondary amine under hydroaminating conditions, and the resulting butenylamine(s) are then reacted in a second process stage under hydrogenating and transalkylating conditions.
    Type: Grant
    Filed: December 26, 2001
    Date of Patent: December 10, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Frank Funke, Ulrich Steinbrenner, Peter Zehner, Ralf Böhling, Wolfgang Harder
  • Publication number: 20020115890
    Abstract: A process for the preparation of one or more ethanolamines (I), chosen from the group consisting of monoethanolamine, diethanolamine and triethanolamine, by conversion of one or more ethanolamines (II) different from the ethanolamine(s) (I), chosen from the group consisting of monoethanolamine, diethanolamine, triethanolamine, O,N,N-tris(2-hydroxyethyl)ethanol-N-(2-aminoethyl)-ethanolamine, N-(2-amine, hydroxy ethyl) piperazine, N-(2-hydroxyethyl)morpholine and N,N′-bis(2-hydroxyethyl)piperazine, where the ethanolamine(s) (II), optionally in the presence of ammonia, is/are treated with a strong base.
    Type: Application
    Filed: November 29, 2001
    Publication date: August 22, 2002
    Inventors: Johann-Peter Melder, Gerhard Schulz
  • Patent number: 6248925
    Abstract: This invention pertains to an improvement in a process for the formation of secondary or tertiary amines by the catalytic reductive amination of a nitrile with a primary or secondary amine and, particularly to the reductive amination of C8-20 nitrites with a secondary amine. The catalyst employed in the improved reductive amination process is one which has been promoted with a lithium salt or base, e.g., lithium chloride or lithium hydroxide.
    Type: Grant
    Filed: October 22, 1999
    Date of Patent: June 19, 2001
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Michael Edward Ford, John Nelson Armor
  • Patent number: 5939588
    Abstract: The present invention, which is aimed at providing a novel reaction for converting a fluorine-containing carbonyl compound to an asymmetric fluorine-containing primary amine, relates to a method in which a Schiff base obtained by the condensation of a fluorine-containing carbonyl compound and an asymmetric amine ((S)- or (R)-1-phenylethylamine) is treated in the presence of an appropriate organic base to hydrolyze a tautomeric imine obtained by asymmetrically performing an enzyme-like transamination reaction, yielding an asymmetric fluorine-containing amine.
    Type: Grant
    Filed: December 17, 1997
    Date of Patent: August 17, 1999
    Assignee: Agency of Industrial Science and Technology
    Inventors: Vadim A. Soloshonok, Taizo Ono, Takashi Abe
  • Patent number: 5817593
    Abstract: This invention includes catalysts comprising rhenium (atomic number 75), nickel, cobalt, boron and copper and/or ruthenium impregnated on a support material and a process for preparing said catalyst, said process comprising (i) impregnating a mixture of metals comprising rhenium, cobalt, copper and/or ruthenium, boron and nickel on a support material selected from the group consisting of alpha-alumina, silica, silica-alumina, kieselguhrs or diatomaceous earths, and silica-titanias; and (ii) activating said catalyst by heating the catalyst in the presence of hydrogen at an effective temperature preferably in the range of about 150.degree. C. to about 500.degree. C. for a sufficient period preferably of from about 30 minutes to about 6 hours.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: October 6, 1998
    Assignee: The Dow Chemical Company
    Inventors: Dane Chang, Fred A. Sherrod
  • Patent number: 5801285
    Abstract: The present invention relates to a process for preparing 2-methyl-2,4-diaminopentane by introducing acetone, ammonia and hydrogen into a two-zone reactor at a temperature of 20.degree. to 130.degree. C. and a pressure of 30 to 250 bar, wherein the first zone contains a cationic exchange resin containing NH.sub.4.sup..sym. groups or an aluminum oxide and/or silicon oxide catalyst and the second zone contains a hydrogenation catalyst containing nickel.
    Type: Grant
    Filed: October 31, 1997
    Date of Patent: September 1, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Helmut Waldmann, Jurgen Dahmer, Anatoly Bazanov, Alexandre Timofeev, Natalja Zubritskaya, Gennady Terechtchenko
  • Patent number: 5773659
    Abstract: To develop a zeolite catalyst which can prevent the drastic lowering of dimethylamine selectivity to be caused in the production of dimethylamine using a zeolite catalyst when the conversion of methanol is high, and which can give higher dimethylamine selectivity and lower trimethylamine selectivity as well as higher methanol-consuming reaction activity; and to provide a process for producing dimethylamine with high selectivity, using the catalyst.A process for producing dimethylamine by allowing methanol, or methanol and a methylamine mixture, or a methylamine mixture to react with ammonia in the gaseous phase in the presence of a catalyst, characterized in that a modified zeolite prepared by treating a zeolite with a solution containing a chelating agent is used as the catalyst.
    Type: Grant
    Filed: July 24, 1996
    Date of Patent: June 30, 1998
    Assignee: Nitto Kagaku Kogyo Kabushiki Kaisha
    Inventors: Michio Fukatsu, Katsumasa Nishijima, Takeshi Narita, Toshio Nakamura, Kiyonobu Niwa
  • Patent number: 5739403
    Abstract: 4-Aminodiphenylamines are produced by reacting optionally substituted aniline with optionally substituted nitrobenzene in the presence of water and/or alcohols and organic and/or inorganic bases and then catalytically hydrogenating the resultant nitro- and/or nitrosodiphenylamine in the presence of water, wherein the catalytic hydrogenation of the reaction mixture is performed in the presence of 25 to 80 wt. % of water, relative to the weight of the reaction mixture from the condensation reaction, the hydrogenation catalyst is removed from the hydrogenation mixture once absorption of hydrogen has ceased, 10 to 100 vol. % of aromatic solvent, relative to the total volume of the hydrogenation mixture, are optionally added to the hydrogenation mixture, the resultant organic phase is separated in order to isolate the 4-aminodiphenylamine and the aqueous phase is returned to the initial reaction mixture.
    Type: Grant
    Filed: January 6, 1997
    Date of Patent: April 14, 1998
    Assignee: Bayer AG
    Inventors: Klaus Reinartz, Adolf Brill, Fred Schuhmacher
  • Patent number: 5648545
    Abstract: Catalysts consisting of from 85 to 100 wt % of copper oxide and zirconium oxide and from 15 to 0 wt % of metal oxides of the subgroups Ib to VIIb and VIII of the Periodic Table and a process for the preparation of amines from nitriles and nitrogen compounds selected from the group comprising ammonia and primary and secondary amines, at temperatures of from 80.degree. to 250.degree. C. and pressures of from 1 to 400 bar using hydrogen in the presence of said catalysts.
    Type: Grant
    Filed: July 5, 1995
    Date of Patent: July 15, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Reif, Michael Hesse, Horst Zimmermann, Heinz Lingk
  • Patent number: 5608114
    Abstract: Upon subjecting trimethylamine with ammonia and optionally, a methylamine to a disproportioning reaction to reduce the proportion of the trimethylamine, use of a zeolite as a catalyst, said zeolite being mordenite, clinoptilolite or the like at least 80% of whose ion-exchangeable cations being in the form of hydrogen ions, makes it possible to efficiently conduct the reaction at a low reaction temperatures and also to suppress by-production of impurities such as acetonitrile.
    Type: Grant
    Filed: December 15, 1994
    Date of Patent: March 4, 1997
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventor: Tadamitsu Kiyoura
  • Patent number: 5567847
    Abstract: This invention relates to an improvement in a process for the production of amines and particularly secondary amines by the hydrogenation of aliphatic and aromatic nitriles and disproportionation of the resulting primary amine containing feedstock. The improvement resides in the use of a bimetallic catalyst comprising nickel or cobalt in combination with rhodium, ruthenium or palladium platinum. Optionally, the catalyst is carried on an alumina support.
    Type: Grant
    Filed: February 21, 1995
    Date of Patent: October 22, 1996
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Gamini A. Vedage, John N. Armor
  • Patent number: 5559270
    Abstract: An improved process of synthesizing gasoline soluble polyolefinic amines or polyether amines comprising the steps of reacting polyolefinic halides or polyether halides with polyamines in a specific sequence of reactions; distilling off non-reactive polyamine; neutralizing the reaction mixture; recovering polyamine(s) and water; and separating polyolefinic amines from the solids with simple filtration or centrifuge or decanting.
    Type: Grant
    Filed: December 15, 1994
    Date of Patent: September 24, 1996
    Assignee: Petrokleen, Ltd.
    Inventors: Donald E. Koehler, William J. Claffey
  • Patent number: 5557011
    Abstract: Process for the preparation of diamines of the general formula I ##STR1## in which A denotes a C.sub.1 -C.sub.20 alkylene chain optionally mono- to penta-substituted by C.sub.1 -C.sub.4 alkyl,R.sup.1, R.sup.2 denote C.sub.1 -C.sub.20 alkyl, C.sub.1 -C.sub.20 hydroxyalkyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.4 -C.sub.20 alkylcycloalkyl, C.sub.4 -C.sub.20 cycloalkylalkyl, phenyl, C.sub.7 -C.sub.20 phenylalkyl, C.sub.1 -C.sub.20 alkoxyalkyl, C.sub.7 -C.sub.20 phenoxyalkyl or together a saturated or unsaturated C.sub.2 -C.sub.6 alkylene chain optionally monosubstituted, disubstituted, or trisubstituted by C.sub.1 -C.sub.4 alkyl and optionally interrupted by oxygen or nitrogen,by the reaction of dinitriles of the general formula IINC--A--CN (II),in which A has the aforementioned meaning,with secondary amines of the general formula II ##STR2## in which R.sup.1 and R.sup.2 have the aforementioned meanings, with hydrogen at temperatures ranging from 50.degree. to 200.degree. C.
    Type: Grant
    Filed: November 15, 1994
    Date of Patent: September 17, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Tom Witzel, Eberhard Fuchs
  • Patent number: 5554793
    Abstract: A process of reforming an alkyleneamine feedstock or a mixture of such feedstocks to an alkyleneamine or a mixture of alkyleneamines which is different from the feedstock or feedstock mixture. The process is catalyzed by one of the following: Group VB metal oxides, Group VB metal phosphates, Group IIA metal silicates, and tungsten oxides. For example, ethylenediamine is contacted with a catalyst of niobic acid or magnesium silicate to yield predominantly diethylenetriamine and non-cyclic triethylenetetramines; whereas high molecular weight polyethylenepolyamines are cracked by the same catalysts to mixtures of lower molecular weight linear and cyclic materials.
    Type: Grant
    Filed: December 19, 1994
    Date of Patent: September 10, 1996
    Assignee: The Dow Chemical Company
    Inventors: George E. Hartwell, Robert G. Bowman, David C. Molzahn
  • Patent number: 5410086
    Abstract: This invention relates to a method for controlling the weight ratio of diethylenetriamine to piperazine in a process in which ethylenediamine, or a mixture of ethylenediamine and monoethanolamine, and hydrogen are maintained in the presence of a hydrogenation catalyst, which method comprises adjusting the hydrogen concentration in the liquid phase in an amount sufficient to effectuate control of the weight ratio of diethylenetriamine to piperazine in said process.
    Type: Grant
    Filed: June 25, 1991
    Date of Patent: April 25, 1995
    Inventor: Lloyd M. Burgess