Preparing Hexamethylene Diamine Patents (Class 564/492)
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Patent number: 11359295Abstract: Provided are methods of making aliphatic or aromatic compounds (e.g., small molecules or polymers) having one or more amine groups and/or imine groups. A method of the present disclosure is an electrohydrogenation method, where a potential is applied to an aliphatic or aromatic compound (e.g., small molecule or polymer) having one or more nitrile groups, where after the potential is applied one or more of the nitrile groups are reduced to an amine or imine. The electrohydrogenation may be carried out using non-pulsed or pulsed potential waveforms.Type: GrantFiled: May 11, 2021Date of Patent: June 14, 2022Assignee: New York UniversityInventors: Miguel A. Modestino, Daniela Eugenia Blanco, Zainub Aaliyah Imran Dookhith
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Patent number: 11192845Abstract: Provided is a hydrogenation method of a phthalate compound. According to the present invention, in the hydrogenation reaction, generation of by-products is suppressed, and thus catalytic activity is improved and life-time is extended, thereby increasing efficiency of a commercial process and economic efficiency. Further, since the hydrogenation product prepared by the present invention has high purity and a low acid value, its quality as a plasticizer is excellent, thereby being applied to a variety of products.Type: GrantFiled: November 1, 2018Date of Patent: December 7, 2021Assignee: HANWHA SOLUTIONS CORPORATIONInventors: Ki Taeg Jung, Hyo Suk Kim, Seong Min Park, Hye Won Lee, Jae Heum Jung
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Patent number: 11148992Abstract: Provided is a hydrogenation method of a phthalate compound. According to the present invention, in the hydrogenation reaction, generation of by-products is suppressed, and thus catalytic activity is improved and life-time is extended, thereby increasing efficiency of a commercial process and economic efficiency. Further, since the hydrogenation product prepared by the present invention has high purity and a low acid value, its quality as a plasticizer is excellent, thereby being applied to a variety of products.Type: GrantFiled: November 1, 2018Date of Patent: October 19, 2021Assignee: HANWHA SOLUTIONS CORPORATIONInventors: Ki Taeg Jung, Hyo Suk Kim, Seong Min Park, Hye Won Lee, Jae Heum Jung
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Patent number: 10519096Abstract: The present invention relates to a process for hydrogenating nitrile compounds to amino compounds, in which the cross-sectional loading of the reactor during the hydrogenation is less than or equal to 4.0 kg/m2*s, based on the liquid phase.Type: GrantFiled: May 17, 2018Date of Patent: December 31, 2019Assignee: Evonik Degussa GmbHInventors: Anne Rittsteiger, Stephan Kohlstruk, Dirk Hoppe, Alexander Martin Rüfer, Sabrina Sowka, Sven Schneider, Norbert Schlüter, Axel Hengstermann, Markus Galle, Stefan Röder, Monika Berweiler
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Patent number: 9822067Abstract: The present invention relates to a process for purifying adiponitrile (ADN), wherein crude ADN is introduced into a rectification apparatus (R1). The rectification apparatus (R1) comprises a first side draw and preferably also a second side draw, the first side draw being disposed below the crude ADN introduction point and the optional second side draw being disposed above the crude ADN introduction point. The first side draw is used to draw off a gaseous stream comprising ADN while the optional second side draw is used to draw off undesired by-products such as 1-amino-2-cyanocyclopentene (ACCP) which are often generated in ADN production and consequently may be present in the crude ADN. The gaseous stream from the first side draw of (R1) is introduced into a second rectification apparatus (R2). (R2) is used to separate off ADN from remaining high boilers and any other by-products present, pure ADN being drawn off from (D2) as overhead product.Type: GrantFiled: February 3, 2015Date of Patent: November 21, 2017Assignee: BASF SE (Ellwanger & Baier Patentanwälte)Inventors: Hermann Luyken, Peter Pfab, Tim Jungkamp
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Patent number: 8933272Abstract: It is described a process for the production of hexamethylenediamine by hydrogenation of adiponitrile, comprising an improved step of regeneration of the catalyst. Also described are an equipment for the production of hexamethylenediamine, and a washing apparatus (14) for implementing the catalyst regeneration step.Type: GrantFiled: April 15, 2011Date of Patent: January 13, 2015Assignee: Radici Chimica S.p.A.Inventors: Tommaso Crippa, Stefano Alini, Luciano Guida, Alberto Corona
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Patent number: 8884064Abstract: The present invention relates to a process comprising at least the steps (A) chemical reaction of at least one organic compound in the presence of at least one heterogeneous catalyst in a reaction mixture and (B) removal of the at least one heterogeneous catalyst by means of a magnetic filter, and also the use of a magnetic filter for separating off catalyst particles in a process for the hydrogenation of at least one organic compound.Type: GrantFiled: December 29, 2011Date of Patent: November 11, 2014Assignee: BASF SEInventors: Frank Kuhnke, Jörg Heilek, Daniela Rieck
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Publication number: 20140024859Abstract: It is described a process for the production of hexamethylenediamine by hydrogenation of adiponitrile, comprising an improved step of regeneration of the catalyst. Also described are an equipment for the production of hexamethylenediamine, and a washing apparatus (14) for implementing the catalyst regeneration step.Type: ApplicationFiled: April 15, 2011Publication date: January 23, 2014Applicant: Radici Chimica S.p.A.Inventors: Tommaso Crippa, Stefano Alini, Luciano Guida, Alberto Corona
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Publication number: 20130324694Abstract: Processes for producing nitrogen containing compounds include producing hexamethylenediamine (HMD), adiponitrile (ADN), adipamide (ADM) and derivatives thereof from adipic acid (AA) obtained from fermentation broths containing diammonium adipate (DAA) or monoammonium adipate (MAA).Type: ApplicationFiled: June 10, 2011Publication date: December 5, 2013Applicant: BIOAMBER S.A.S.Inventors: Olan S. Fruchey, Leo E. Manzer, Dilum Dunuwila, Brian T. Keen, Brooke A. Albin, Nye A. Clinton, Bernard D. Dombek
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Patent number: 8362301Abstract: Amine compounds, more particularly diamine compounds, are prepared by hydrogenating compounds including nitrile functions. The preparation can include the use of a hydrogenation catalyst, adapted for the hydrogenation of nitrile compounds into amine compounds, including Raney nickel as well as iron, chromium, and zinc as doping elements.Type: GrantFiled: September 1, 2009Date of Patent: January 29, 2013Assignee: Rhodia OperationsInventors: Didier Letourneur, Stephan Verdier
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Publication number: 20120329981Abstract: The invention provides a process for the preparation of valerolactone, said process comprising reacting levulinic acid with hydrogen by using a solid Ru catalyst, characterised in that the process is carried out in the presence of at least 0.08% (w/w) water relative to the amount of levulinic acid. Said process may be faster and more selective. This process advantageously allows the production of valerolactone from renewable sources. The valerolactone may be used in the preparation of methylpentenoate, adipic acid dimethylester, adipic acid, hexamethylenediamine, and polyamide 6,6 (all claimed).Type: ApplicationFiled: June 20, 2012Publication date: December 27, 2012Applicant: DSM IP ASSETS B.V.Inventors: Anna Maria Cornelia Francisca Castelijns, Michele Catherine Christianne Janssen, Henricus Wilhemus Leonardus Marie Vaessen
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Patent number: 8329955Abstract: Amino compounds are continuously prepared by hydrogenation of nitrile compounds in the presence of a catalyst, and more particularly diamines are prepared by the continuous hydrogenation of dinitrile compounds in the presence of a Raney metal catalyst and in the absence of an alcoholic solvent; the subject process includes extracting a portion of the catalyst present in the reaction medium, the extracted portion of the catalyst is submitted to a regeneration for providing a catalyst having a catalytic activity lower than that of a fresh catalyst but still high and the regenerated catalyst is recycled to the reaction medium together with fresh catalyst according to a predetermined ratio, whereby the consumption of catalyst is reduced per ton of amines produced.Type: GrantFiled: October 2, 2008Date of Patent: December 11, 2012Assignee: Rhodia OperationsInventors: Didier Letourneur, Philippe Leconte, Jean-Francis Spindler, Patrick Lermusiaux, Vincent Boschat
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Patent number: 8227642Abstract: A method for producing amines by the hydrogenation of nitrile compounds in the presence of a catalyst, notably a method for producing diamines by the continuous hydrogenation of dinitrile compounds in the presence of a Raney-metal catalyst, includes controlling the molar flow of nitrile compounds and the mass flow of catalyst in a hydrogenation piston reactor in order to minimize the occurrence of impurities and deterioration of the catalyst.Type: GrantFiled: September 13, 2007Date of Patent: July 24, 2012Inventors: Philippe Roccati, Didier Letourneur, Philippe Denis
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Publication number: 20110313187Abstract: The present invention relates to a process for improving the catalytic properties of a catalyst comprising one or more elements selected from the group consisting of cobalt, nickel and copper, said catalyst being present in the form of a structured monolith, by contacting the catalyst with one or more basic compounds selected from the group of the alkali metals, alkaline earth metals and rare earth metals. The invention further relates to a process for hydrogenating compounds which comprise at least one unsaturated carbon-carbon, carbon-nitrogen or carbon-oxygen bond in the presence of a catalyst comprising one or more elements selected from the group consisting of cobalt, nickel and copper, said catalyst being present in the form of a structured monolith, by contacting the catalyst with one or more basic compounds selected from the group of the alkali metals, alkaline earth metals and rare earth metals.Type: ApplicationFiled: February 1, 2010Publication date: December 22, 2011Inventors: Christof Wilhelm Wigbers, Jochen Steiner, Martin Ernst, Bram Willem Hoffer, Ekkehard Schwab, Johann-Peter Melder
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Patent number: 8076518Abstract: This invention provides chain extender compositions. These compositions comprise (i) an aliphatic secondary diamine, and (ii) a component selected from the group consisting of: (a) a cycloaliphatic primary diamine; (b) an aliphatic secondary diamine; (c) an aliphatic secondary diamine and an aliphatic primary diamine; (d) an aliphatic diimine; and (e) a combination of any two or more of (a) through (d), with the proviso that when (ii) is (a), (i) is a noncyclic aliphatic secondary diamine. Processes for producing polyurethanes, polyureas, and polyurea-urethanes are also provided.Type: GrantFiled: September 25, 2006Date of Patent: December 13, 2011Assignee: Albemarle CorporationInventors: Paul L. Wiggins, John Y. Lee, Judit Orgad, David W. Owens
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Publication number: 20110230681Abstract: Amine compounds, more particularly diamine compounds, are prepared by hydrogenating compounds including nitrile functions. The preparation can include the use of a hydrogenation catalyst, adapted for the hydrogenation of nitrile compounds into amine compounds, including Raney nickel as well as iron, chromium, and zinc as doping elements.Type: ApplicationFiled: September 1, 2009Publication date: September 22, 2011Applicant: RHODIA OPERATIONSInventors: Didier . Letourneur, Stephan Verdier
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Patent number: 8003826Abstract: The invention relates to an improved process for preparing trimethylhexamethylenediamine, hereinafter referred to as TMD for short, by hydrogenation of trimethylhexamethylenedinitrile, hereinafter referred to as TMN for short, in the presence of a shaped hydrogenation catalyst of the Raney type.Type: GrantFiled: January 30, 2008Date of Patent: August 23, 2011Assignee: Evonik Degussa GmbHInventors: Christian Lettmann, Gerda Grund, Juergen Lippe, Cord Knoop
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Patent number: 7939691Abstract: Primary diamines are prepared by hydrogenation of a dinitrile compound in the presence of a catalyst, in particular hexamethylenediamine is prepared by hydrogenation of adiponitrile; the product diamines are recovered by distillation in several distillation columns mounted in series and the heavy impurities are separated from the second distillation.Type: GrantFiled: June 15, 2007Date of Patent: May 10, 2011Assignee: Rhodia OperationsInventors: Daniel Amoros, Denis Rachez
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Patent number: 7939027Abstract: The present invention relates to a process for the industrial preparation of a diamine starting from a corresponding alkenyl nitrile comprising at least one C—C double bond, which comprises the steps (a) reaction of the alkenyl nitrile with a corresponding monoamine in a first reactor so that the monoamine adds exothermically onto the at least one double bond to form an aminoalkyl nitrile, with the monoamine and water being charged initially and the alkenyl nitrile being fed in; (b) evaporation of unreacted alkenyl nitrile and monoamine to increase the concentration of the aminoalkyl nitrile product in the bottoms of the first reactor; (c) transfer of the aminoalkyl nitrile bottom product from step (b) to a second reactor; (d) batchwise catalytic hydrogenation of the aminoalkyl nitrile transferred in step (c) to the diamine in the second reactor, with each batch being obtained by initially charging a catalyst suitable for the hydrogenation of nitriles to amines and also water, the desired diamine and a basType: GrantFiled: January 6, 2010Date of Patent: May 10, 2011Assignee: BASF SEInventors: Martin Ernst, Steffen Oehlenschläger, Frank Kuhnke, Karl-Heinz Roβ, Roland Deeg, Johann-Peter Melder
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Patent number: 7915454Abstract: The invention relates to a process for preparing ethylenediamine by hydrogenation of aminoacetonitrile over a catalyst, wherein the hydrogenation is carried out in a solution comprising aminoacetonitrile, water in a proportion of from 0 to 60% by weight and a solvent and the aminoacetonitrile comprised in the solution is fed into the reaction vessel at a rate which is not greater than the rate at which the aminoacetonitrile reacts with hydrogen in the hydrogenation.Type: GrantFiled: February 28, 2008Date of Patent: March 29, 2011Assignee: BASF SEInventors: Alfred Oftring, Kirsten Dahmen, Randolf Hugo, Thilo Hahn, Katrin Baumann, Johann-Peter Melder
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Patent number: 7880036Abstract: The invention relates to a process for preparing an ethylene amine mixture, which comprises hydrogenating an amino nitrile mixture comprising at least two ?-amino nitriles in an amount of at least 5% by weight in each case in the presence of a catalyst and, if appropriate, a solvent.Type: GrantFiled: February 27, 2008Date of Patent: February 1, 2011Assignee: BASF SEInventors: Kirsten Dahmen, Alfred Oftring, Katrin Baumann, Randolf Hugo, Thilo Hahn, Johann-Peter Melder
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Patent number: 7875740Abstract: The iron-containing catalyst suitable for use as a catalyst contains a) iron or a mixture containing iron and an iron-based compound. The iron has an average crystallite size ranging from 1-35 nm measured by X-ray diffraction.Type: GrantFiled: October 18, 2002Date of Patent: January 25, 2011Assignee: BASF AktiengesellschaftInventors: Andreas Ansmann, Christoph Benisch, Peter Baβler, Rolf-Hartmuth Fischer, Stefan Maixner, Johann-Peter Melder, Hermann Luyken
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Publication number: 20100317823Abstract: The present invention generally relates to processes for the chemocatalytic conversion of a glucose source to an adipic acid product. The present invention includes processes for the conversion of glucose to an adipic acid product via glucaric acid or derivatives thereof. The present invention also includes processes comprising catalytic oxidation of glucose to glucaric acid or derivative thereof and processes comprising the catalytic hydrodeoxygenation of glucaric acid or derivatives thereof to an adipic acid product. The present invention also includes products produced from adipic acid product and processes for the production thereof from such adipic acid product.Type: ApplicationFiled: June 11, 2010Publication date: December 16, 2010Applicant: RENNOVIA, INC.Inventors: Thomas R. Boussie, Eric L. Dias, Zachary M. Fresco, Vincent J. Murphy, James Shoemaker, Raymond Archer, Hong Jiang
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Patent number: 7767859Abstract: A method of producing a primary amine by the hydrogenation of a nitrile in the presence of a hydrogenation catalyst. The hydrogenation catalyst contains at least one metal selected from the group consisting of nickel, cobalt and iron. Before use in the hydrogenation of nitrile, the hydrogenation catalyst is pretreated with at least one treating agent selected from the group consisting of hydrocarbons, alcohols, ethers, esters and carbon monoxide at 150 to 500° C.Type: GrantFiled: August 9, 2007Date of Patent: August 3, 2010Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Kazuhiko Amakawa, Yoshiaki Yamamoto
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Publication number: 20100130789Abstract: A method for producing amines by the hydrogenation of nitrile compounds in the presence of a catalyst, notably a method for producing diamines by the continuous hydrogenation of dinitrile compounds in the presence of a Raney-metal catalyst, includes controlling the molar flow of nitrile compounds and the mass flow of catalyst in a hydrogenation piston reactor in order to minimize the occurrence of impurities and deterioration of the catalyst.Type: ApplicationFiled: September 13, 2007Publication date: May 27, 2010Inventors: Philippe Roccati, Didier Letourneur, Philippe Denis
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Publication number: 20100094058Abstract: Process for preparing trimethylhexamethylenediamine The invention relates to an improved process for preparing trimethylhexamethylenediamine, hereinafter referred to as TMD for short, by hydrogenation of trimethylhexamethylenedinitrile, hereinafter referred to as TMN for short, in the presence of a shaped hydrogenation catalyst of the Raney type.Type: ApplicationFiled: January 30, 2008Publication date: April 15, 2010Applicant: Evonik Degussa GmbHInventors: Christian Lettmann, Gerda Grund, Juergen Lippe, Cord Knoop
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Publication number: 20100036169Abstract: Primary diamines are prepared by hydrogenation of a dinitrile compound in the presence of a catalyst, in particular hexamethylenediamine is prepared by hydrogenation of adiponitrile; the product diamines are recovered by distillation in several distillation columns mounted in series and the heavy impurities are separated from the second distillation.Type: ApplicationFiled: June 15, 2007Publication date: February 11, 2010Inventor: Daniel Amoros
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Publication number: 20090018366Abstract: Method for the production of supported activated metal catalysts, whereby an alloy, a metal powder, a pore builder is dispersed in a water, the dispersion is sprayed on a support which is the dried, calcined and activated. The catalysts can be used for organic transformations, i.e. for hydrogenation reactions.Type: ApplicationFiled: September 8, 2005Publication date: January 15, 2009Inventors: Monika Berweiler, Daniel Ostgard, Thomas Quandt, Stefan Roder
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Publication number: 20080319220Abstract: Hexamethylenediamine and aminocapronitrile are simultaneoussly produced by hemihydrogenation of adiponitrile, which includes a stage of separation of the hexamethylenediamine from the hydrogenate by distillation of the hexamethylenediamine, the distillation of the hexamethylenediamine being carried out from the hydrogenate containing a free acid and/or an alkali metal or ammonium acid salt, whereby a top fraction A recovered at the column top of the stage of distillation of the hexamethylenediamine is essentially crude hexamethylenediamine and a small amount of THA; the amount of THA (tetrahydroazepine) present in the crude hexamethylenediamine constitutes a small proportion of the THA present in the hydrogenate.Type: ApplicationFiled: October 16, 2006Publication date: December 25, 2008Applicant: RHODIA OPERATIONSInventor: Philippe Leconte
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Publication number: 20080306305Abstract: A process for hydrogenating oligonitriles which have at least two nitrile groups in the presence of a catalyst which, before commencement of the hydrogenation, is pretreated by contacting with a compound A which is selected from alkali metal carbonates, alkaline earth metal carbonates, ammonium carbonate, alkali metal hydrogencarbonates, alkaline earth metal hydrogencarbonates, ammonium hydrogencarbonate, alkaline earth metal oxocarbonates, alkali metal carboxylates, alkaline earth metal carboxylates, ammonium carboxylates, alkali metal dihydrogen phosphates, alkaline earth metal dihydrogen phosphates, alkali metal hydrogen phosphates, alkaline earth metal hydrogen phosphates, alkali metal phosphates, alkaline earth metal phosphates and ammonium phosphate, alkali metal acetates, alkaline earth metal acetates, ammonium acetate, alkali metal formates, alkaline earth metal formates, ammonium formate, alkali metal oxalates, alkaline earth metal oxalates and ammonium oxalate.Type: ApplicationFiled: December 5, 2006Publication date: December 11, 2008Applicant: Basf SEInventors: Thilo Hahn, Martin Ernst, Johann-Peter Melder
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Patent number: 7453012Abstract: A process for the hydrogenation of compounds comprising nitrile or nitro functional groups to amine, aminonitrile or aminonitro compounds is provided. The process can be a continuous process conducted in the presence of a heterogeneous hydrogenation catalyst in divided form and a basic compound. The reaction can be conducted in a stirred reactor comprising an external loop for circulating the reaction mixture, allowing one portion of the hydrogenated products to be separated without withdrawing the catalyst, by using tangential filtration. The process may be especially useful in the hydrogenation of adiponitrile to an aminocapronitrile/hexamethylenediamine mixture.Type: GrantFiled: January 20, 2003Date of Patent: November 18, 2008Assignee: Rhodia Polyamide IntermediatesInventors: Gérald Bocquenet, André Chesnais, Jean-Michel Desire, Philippe Leconte, Lionel Sever
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Patent number: 7381845Abstract: A process for hydrogenating nitrile functions present in organic compounds over at least one heterogeneous catalyst, in which the hydrogenation is carried out in the presence of an ionic liquid, is described.Type: GrantFiled: December 20, 2004Date of Patent: June 3, 2008Assignee: BASF AktiengesellschaftInventors: Verena Weiskopf, Till Gerlach, Kirsten Wenz
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Patent number: 7291754Abstract: Process for the catalytic hydrogenation of a nitrite in the presence of an amine and a catalyst wherein the catalyst is a liquid-rinsed Raney-type catalyst contacted with a hydroxide prior to contacting the catalyst with the amine. The process results in higher selectivity in the formation of diamines from diniriles.Type: GrantFiled: January 21, 2004Date of Patent: November 6, 2007Assignee: DSM IP Assets B.V.Inventors: Franciscus H. A. M. Vandenbooren, Hubertus J. M. Bosman, Alexander V. Peters, Maria J. G. Van Den Boer
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Patent number: 7214829Abstract: The present invention relates to an improvement in a process for preparing primary amines by hydrogenating nitriles. The improvement in the hydrogenation process is that a hydrogenation catalyst modified ex situ with preadsorbed alkali metal carbonate or hydrogencarbonate such as K2CO3 or KHCO3 is used.Type: GrantFiled: February 13, 2003Date of Patent: May 8, 2007Assignee: Clariant Produkte (Deutschland) GmbHInventors: Sandor Goeboeloes, Andras Fasi, Jozsef Margitfalvi, Laszlone Millian
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Patent number: 7208448Abstract: The invention relates to a passivated hydrogenation catalyst that is embedded in a primary amine, a derivative thereof, and/or a nitrile, the process to make such catalysts, as well as the use of such catalysts in a hydrogenation process in which an amine or a derivative thereof is produced.Type: GrantFiled: March 13, 2003Date of Patent: April 24, 2007Assignee: Akzo Nobel N.V.Inventors: Thale Jacob Ottens, Jacobus Van Den Berg, Paul Van Poecke
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Patent number: 7196223Abstract: A nitrile-containing mixture, which includes a nitrile dissolved in a higher alcohol solvent, and hydrogen are fed to a reactor containing a catalyst. An amine is produced by hydrogenating the nitrile that is dissolved in the higher alcohol solvent. In a preferred embodiment, the reactor also contains a caustic solution. The preferred nitrile-containing mixture includes octadecaneditrile (ODDN) and hexanol to produce a preferred octadecanediamine (ODDA) through hydrogenation.Type: GrantFiled: May 3, 2005Date of Patent: March 27, 2007Assignee: Solutia, Inc.Inventors: Tom L. Flowers, Anthony K. Uriarte, Shannon Davis, Gregory J. Ward
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Patent number: 7132562Abstract: Catalytic process for hydrogenating a dinitrile to produce both aminocapronitrile and hexamethylenediamine in which the dinitrile is contacted with hydrogen in the presence of a catalyst and a modifier selected from the group consisting of quaternary ammonium hydroxides, cyanides, fluorides and thiocyanides; quaternary phosphonium hydroxide; carbon monoxide; and hydrogen cyanide.Type: GrantFiled: November 12, 2003Date of Patent: November 7, 2006Assignee: Invista North America S.A R.L.Inventor: Alan Martin Allgeier
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Patent number: 7115781Abstract: An oxidic composition which is suitable as a catalyst having divalent and trivalent iron in an atomic ratio of divalent to trivalent iron in the range from greater than 0.5 to 5.5 and oxygen as a counterion to the divalent and trivalent iron. The catalyst composition is useful in the hydrogenation of nitriles to amines.Type: GrantFiled: October 18, 2002Date of Patent: October 3, 2006Assignee: BASF AktiengesellschaftInventors: Andreas Ansmann, Christoph Benisch, Peter Bassler, Rolf-Hartmuth Fischer, Stefan Maixner, Johann-Peter Melder, Hermann Luyken
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Publication number: 20040182690Abstract: A method for recovering hexamethylene diamine (HMD) from a mixture comprising HMD, 6-aminocapronitrile (ACN) tetrahydroazepine (THA), and ADN comprising:Type: ApplicationFiled: March 7, 2003Publication date: September 23, 2004Inventor: John J. Ostermaier
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Patent number: 6790994Abstract: The present invention relates to a process for the hydrogenation of nitrile functional groups to amine functional groups. It relates more particularly to a process for the complete or partial hydrogenation of dinitrile compounds to diamine or aminonitrile compounds. The invention relates to a process for the hydrogenation of nitrile functional groups to amine functional groups using hydrogen in the presence of a hydrogenation catalyst and of a strong inorganic base preferably deriving from an alkali metal or alkaline earth metal. According to the invention, the process comprises a stage of conditioning the catalyst which consists in mixing the hydrogenation catalyst, a predetermined amount of strong inorganic base and a solvent in which the strong inorganic base is not very soluble. This solvent is an amine compound, such as hexamethylenediamine in the case of the hydrogenation of adiponitrile to HMD and/or aminocapronitrile.Type: GrantFiled: January 10, 2003Date of Patent: September 14, 2004Assignee: Rhodia Polyamide IntermediatesInventors: Vincent Boschat, Philippe Leconte
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Patent number: 6790996Abstract: The invention relates to a process for preparing primary amines by hydrogenating nitrites in the presence of a catalyst comprising cobalt and optionally, in addition, nickel and also at least one further doping metal on a particulate support material, the cobalt and, if present, the nickel having an average particle size of from 3 to 30 nm in the active catalyst. The invention further relates to the use of the catalyst in a process for preparing primary amines by hydrogenating nitrites.Type: GrantFiled: October 17, 2002Date of Patent: September 14, 2004Assignee: BASF AktiengesellschaftInventors: Andreas Ansmann, Christoph Benisch
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Patent number: 6677486Abstract: Nitriles are hydrogenated to primary amines over an activated, alpha-Al2O3-containing, macroporous Raney catalyst based on an alloy of aluminum and at least one transition metal selected from the group consisting of iron, cobalt and nickel, and, if desired, one or more further transition metals selected from the group consisting of titanium, zirconium, chromium and manganese, which is obtainable by a process comprising the steps in the order (a)-(f): (a) preparing a kneadable composition comprising the alloy, a shaping aid, water and a pore former; (b) shaping the kneadable composition to form a shaped body; (c) calcining the shaped body; (d) activating the calcined shaped body by treatment with aqueous alkali metal hydroxide solution; (e) rinsing the shaped catalyst body with aqueous alkali metal hydroxide solution; (f) rinsing the shaped catalyst body with water.Type: GrantFiled: November 7, 2001Date of Patent: January 13, 2004Assignee: BASF AktiengesellschaftInventors: Andreas Ansmann, Christoph Benisch, Frank Funke, Frank Ohlbach, Martin Merger
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Patent number: 6649799Abstract: A method for producing amines by catalytic hydrogenation of nitrites or imines with hydrogen-containing gases in the presence of a molded hydrogenation catalyst of Raney type, where the Raney catalyst is in the form of hollow bodies.Type: GrantFiled: December 21, 2001Date of Patent: November 18, 2003Assignee: Degussa AGInventors: Daniel Ostgard, Monika Berweiler, Stefan Röder
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Publication number: 20030212298Abstract: The invention relates to the production of hexamethylene diamine from butadiene. The method comprises the successively performed stages of: (i) a catalytic epoxidation of butadiene to 1,2-epoxy-3-butene; (ii) a basically catalyzed addition of hydrogen cyanide to butadiene monoxide to form a reaction mixture containing 3-hydroxy-4-pentene nitrile (3HPN) and 2-hydroxymethyl-3-butene nitrile (2HMBN); (iii) an acidically catalyzed dehydration of the cyanohydrines 3HPN and 2HMBN of stage (ii) to cis/trans-pentadiene nitrile (PDN); (iv) a basically catalyzed addition of the products of stage (iii) to form cis/trans-1,4-dicyanobutene-1 and -2 (DCB); and (v) a catalytic hydrogenation of the isomeric cis/trans-1,4-dicyanobutene of stage (iv) to hexamethylene diamine.Type: ApplicationFiled: March 26, 2003Publication date: November 13, 2003Applicant: Degussa AGInventors: Claudia Brasse, Thomas Haas, Robert Weber, Jurgen Neuroth
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Patent number: 6600075Abstract: Disclosed is a method for preparing tertiary amine compounds from primary amines and nitrites in the presence of hydrogen gas and a metal catalyst, or metal-containing catalyst composition, at a temperature from about 50° C. to about 200° C. and at a pressure from about 100 psig to 1500 psig. The primary amines and the nitriles used in the process may be diamines and/or dinitriles, or may be combinations of primary amines and/or nitrites. Also disclosed are novel tertiary amine compounds made by the described method.Type: GrantFiled: November 13, 2001Date of Patent: July 29, 2003Assignee: E. I. du Pont de Nemours and CompanyInventors: Kelley Moran Whittle, Alan Martin Allgeier, Thomas Papin Gannett, David Page Higley
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Patent number: 6469211Abstract: In a process for the continuous hydrogenation of nitrites to primary amines in the liquid phase over a suspended, activated Raney catalyst based on an alloy of aluminum and at least one transition metal selected from the group consisting of iron, cobalt and nickel, and, if desired, one or more further transition metals selected from the group consisting of titanium, zirconium, chromium and manganese, the hydrogenation is carried out in the absence of ammonia and basic alkali metal compounds or alkaline earth metal compounds.Type: GrantFiled: November 14, 2001Date of Patent: October 22, 2002Assignee: BASF AktiengesellschaftInventors: Andreas Ansmann, Christoph Benisch, Frank Funke, Frank Ohlbach, Martin Merger
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Patent number: 6399830Abstract: 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 amine. The catalyst employed in the improved reductive amination process is one that has been promoted with an acidic promoter preferably a solid phase acidic promoter.Type: GrantFiled: December 13, 2000Date of Patent: June 4, 2002Assignee: Air Products and Chemicals, Inc.Inventors: John Nelson Armor, Michael Edward Ford, William Eamon Carroll
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Patent number: 6384283Abstract: The present invention relates to a process for the preparation of aminonitrile and of diamine by catalytic hydrogenation of dinitrile. It consists of a process for the preparation of aminonitrile and of diamine by catalytic hydrogenation of aliphatic dinitrile having from 3 to 12 carbon atoms, characterized in that the final reaction mixture, the catalyst of which has been separated beforehand, is acidified by addition of a sufficient amount of an inorganic or organic acid, before being subjected to an operation of distillation of the products of the reaction and of the unconverted dinitrile. It relates more particularly to the preparation of 6-aminocapronitrile and of hexamethylenediamine by hydrogenation of adiponitrile. The 6-aminocapronitrile can be hydrolysed in the liquid phase or in the gas phase to result in caprolactam. The hexamethylenediamine can be used very particularly to prepare polyamide-6,6 by reaction with adipic acid.Type: GrantFiled: January 26, 2001Date of Patent: May 7, 2002Assignee: Rhodia Fiber & Resin IntermediatesInventor: Philippe Leconte
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Patent number: 6380420Abstract: A process for preparing fatty amines by the cross-metathesis of normal alpha olefins and acrylonitrile to form an intermediate fatty acid nitrile which is hydrogenated to the corresponding fatty amine.Type: GrantFiled: September 8, 2000Date of Patent: April 30, 2002Assignee: Chevron U.S.A. Inc.Inventors: William L. Schinski, Michael S. Driver
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Patent number: 6376714Abstract: Process for converting a dinitrile to a diamine and optionally an aminonitrile, in which a Group VIII element catalyst is treated with a modifier either before or during a substantially solvent-free hydrogenation reaction in which the dinitrile is contacted with hydrogen in the presence of the catalyst.Type: GrantFiled: May 31, 2001Date of Patent: April 23, 2002Assignee: E. I. du Pont de Nemours and CompanyInventors: Alan M. Allgeier, Theodore A. Koch, Sourav K. Sengupta