Forming Amine Group Directly By Reduction Patents (Class 564/489)
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Publication number: 20140323764Abstract: 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: ApplicationFiled: July 10, 2014Publication date: October 30, 2014Inventors: Yasumitsu SAKUMA, Wataru NOMURA, Goshi YAMAMOTO, Takeshi NARUSHIMA
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Patent number: 8853457Abstract: A method for producing a polyamine is described that provides excellent safety, a lot of flexibility regarding a variety of its productions, and that can produce a polyamine of high-molecular weight easily and inexpensively. The polyamine includes a combination of units of formula (1) or (2): —(NH—(CH2)m—NH—(CH2)n)—??(1) (in the formula (1), independently in every unit, “m” indicates an integral number of 0 or more and “n” indicates an integral number of 3 or more.) —(NH—y—NH —Z)—??(2) (in the formula (2), independently in every unit, “Y” and “Z” are the same as or different from each other, and they indicate substituted or unsubstituted groups including unsaturated aliphatic, cyclic aliphatic or aromatic hydrocarbon radicals that can include hetero atoms.).Type: GrantFiled: December 17, 2010Date of Patent: October 7, 2014Assignee: Rhodia OperationsInventors: Hiroyuki Kitayama, Hironao Sajiki, Yasunari Monguchi
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Patent number: 8795631Abstract: The present invention relates to 18F radio-chemistry and in particular to a method for synthesising radiofluorinated amides and amines. The method of the invention has particular application in the radiosynthesis of a variety of 18F-labelled positron emission tomography (PET) tracers.Type: GrantFiled: October 20, 2009Date of Patent: August 5, 2014Assignees: HammerSmith Imanet Limited, GE Healthcare LimitedInventors: Robert James Domett Nairne, Erik Arstad, Matthias Eberhard Glaser
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Publication number: 20140011973Abstract: The invention discloses a compound having branching alkyl chains, the method for preparing the same and use thereof in photoelectric devices. By applying the branching alkyl chains as the solubilizing group to the preparation of organic conjugated molecules (for example, organic conjugated polymers), the number of methylenes between the resultant alky side chains and the backbone, i.e., m>1, which can effectively reduce the effect of the alkyl chains on the backbone ?-? stacking, thereby ensuring the solubility of the organic conjugated molecule while greatly increasing the mobility of their carriers. It is suitable for an organic semiconductor material in photoelectric devices such as organic solar cells, organic light emitting diodes and organic field effect transistors, etc.Type: ApplicationFiled: July 5, 2013Publication date: January 9, 2014Inventors: Jian PEI, Ting LEI, Jinhu DOU
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Publication number: 20130197234Abstract: The present invention relates to methods for producing an optically active amine compound via a highly enantioselective hydrogenation reaction of an imine compound, wherein the imine compound is hydrogenated using a ruthenium metal complex having high catalytic activity and represented by Formula (1) RuXYAB??(1) such as RuBr2[(S,S)-xylskewphos][(S,S)-dpen].Type: ApplicationFiled: February 1, 2013Publication date: August 1, 2013Applicants: National University Corporation Hokkaido University, Kanto Kagaku Kabushiki KaishaInventors: Kanto Kagaku Kabushiki Kaisha, National University Corporation Hokkaido University
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Patent number: 8354558Abstract: Diastereoselective conversion of chiral imines of the formula I to amines of the formula II where the R1 to R4 radicals are each as defined in the description and R1 and R2 are different than one another, by converting the imine of the formula I in the presence of hydrogen and a heterogeneous copper-containing catalyst.Type: GrantFiled: December 10, 2008Date of Patent: January 15, 2013Assignee: BASF SEInventors: Wolfgang Siegel, Thilo Hahn, Tobias Staeb
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Publication number: 20120077992Abstract: The present invention relates to a device for treatment of material transported through the device comprising at least one porous element consisting of solid, for example metallic, structure which allows cross-flow of the material through the porous element. The invention also relates to various types of uses of the device. A device in accordance with the invention is particularly useful to carry out chemical reactions under homogenous and heterogeneous conditions. Such a device hereinafter also referred as reactor may comprises a tube (1) having a cylindrical wall (2) with one inlet end (3) and one outlet end (4). Arranged in the tube (1) is at least one cylindrical porous element (5) consisting of solid metal structure, wherein said porous element (5) comprises a plurality of hollow spaces that are connected to each other and form an interconnected cavity network and wherein the at least one porous element (5) and the cylindrical wall (2) are made in one piece.Type: ApplicationFiled: June 14, 2010Publication date: March 29, 2012Inventors: Cédric Hutter, Francesco Mascarello, Philipp Von Rohr, David Ruppen
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Publication number: 20120071693Abstract: The present invention provide a process for the production of compounds of general formula (I), Y—CH2CH2—Z (I) wherein Y and Z are functional groups independently selected from the group consisting of a hydroxyl group and R1R2N and wherein R1 and R2 may be the same or different and are functional groups selected from the group consisting of hydrogen and substituted or non-substituited alkyl groups comprising 1 to 8 carbon atoms, or R1R2N is a cyclic compound selected from the group of aromatic and non-aromatic cyclic compounds optionally comprising one or more heteroatoms in addition to the nitrogen atom, said process comprising the steps of: (i) reacting carbon monoxide and an amine in the presence of oxygen to provide a compound of general formula (II) wherein R1 and R2 or R1R2N are as defined above and X is selected from the group consisting of R1R2N and R3O, wherein R3 is selected from alkyl groups comprising 1 to 8 carbon atoms; and (ii) converting the compound of general formula (II) into a compound ofType: ApplicationFiled: May 10, 2010Publication date: March 22, 2012Inventors: Eric Johannes Maria De Boer, Harry Van Der Heijden, Harry Van Der Heijden, Meurs Jan Hermen Hendrik, Sanne Wijnans
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Patent number: 8106242Abstract: Multi-step process for the preparation of compounds via hazardous intermediates comprising the steps of a) preparing in a microreactor a hazardous intermediate and b) optionally performing one or more reaction steps on the hazardous intermediate in one or more additional microreactors and c) further converting the hazardous intermediate with a suitable reaction agent in a subsequent microreactor until a stable end product is formed.Type: GrantFiled: May 23, 2007Date of Patent: January 31, 2012Assignee: DSM IP Assets B.V.Inventors: Rafael Wilhelmus Elisabeth Ghislain Reintjens, Quirinus Bernardus Broxterman, Martina Kotthaus, Peter Poechlauer
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Patent number: 8039675Abstract: Catalysts suitable for asymmetric hydrogenation reactions are described comprising the reaction product of a group 8 transition metal compound, a chiral phosphine and a chiral diamine of formula (I) in which R1, R2, R3 and R4 are independently hydrogen, a saturated or unsaturated alkyl or cycloalkyl group, an aryl group or a urethane or sulphonyl group and R5, R6, R7 and R8 are independently hydrogen, a saturated or unsaturated alkyl or cycloalkyl group, or an aryl group, at least one of R1, R2, R3 and R4 is hydrogen and A is a linking group comprising one or two substituted or unsubstituted carbon atoms.Type: GrantFiled: January 29, 2010Date of Patent: October 18, 2011Assignee: Johnson Matthey PLCInventors: William Patrick Hems, Gabriela Alexandra Grasa
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Patent number: 8013189Abstract: In a process for the accelerated reduction of organic substrates, selected from the group consisting of esters, amides, nitriles, acids, ketones, imines or mixtures thereof, they are reacted with an amine borane, sulfide borane or ether borane complex as a borane source in the presence of organic accelerator compounds containing either Lewis acidic or Lewis basic sites in their structure, of which the Lewis acidic site can coordinate with the carbonyl or nitrile or imine group of the substrate or the Lewis basic site can coordinate with the borane.Type: GrantFiled: September 21, 2007Date of Patent: September 6, 2011Assignee: BASF SEInventors: Elizabeth Burkhardt, Alex J. Attlesey, Christopher P. Sutton, Karl Matos
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Publication number: 20110189089Abstract: The present invention relates to 18F radio-chemistry and in particular to a method for synthesising radiofluorinated amides and amines. The method of the invention has particular application in the radiosynthesis of a variety of 18F-labelled positron emission tomography (PET) tracers.Type: ApplicationFiled: October 20, 2009Publication date: August 4, 2011Inventors: Robert James Domett Nairne, Erik Arstad, Matthias Eberhard Glaser
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Patent number: 7915453Abstract: Disclosed is a process for producing a tertiary amine from a primary or secondary amine and alcohol as corresponding starting materials, which includes step (i) of dehydrogenating an alcohol to obtain an aldehyde, step (ii) of reacting the aldehyde with a primary or secondary amine to obtain a primary or secondary amine adduct, and step (iii) of hydrogenating the primary or secondary amine adduct to obtain a tertiary amine, wherein step (ii) is carried out independently of the other steps.Type: GrantFiled: December 26, 2006Date of Patent: March 29, 2011Assignee: Kao CorporationInventors: Shoji Hasegawa, Toru Nishimura, Atsushi Hirota
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Patent number: 7834224Abstract: Disclosed are iron ligand catalysts for selective hydrogenation of aldehydes, ketones and imines. A catalyst such as dicarbonyl iron hydride hydroxycyclopentadiene) complex uses the OH on the five member ring and hydrogen linked to the iron to facilitate hydrogenation reactions, particularly in the presence of hydrogen gas.Type: GrantFiled: November 20, 2007Date of Patent: November 16, 2010Assignee: Wisconsin Alumni Research FoundationInventors: Charles P. Casey, Hairong Guan
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Patent number: 7767858Abstract: This invention provides aromatic diimines which have imino hydrocarbylidene groups with at least two carbon atoms, and aromatic secondary diamines which have amino hydrocarbyl groups with at least two carbon atoms. Both the aromatic diimines and the aromatic secondary diamines either are in the form of one phenyl ring, or are in the form of two phenyl rings connected by an alkylene bridge; each position ortho to an imino group or an amino group bears a hydrocarbyl group. When in the form of one phenyl ring, there are two imino groups on the ring or two amino groups on the ring; the imino groups or amino groups are meta or para relative to each other. When in the form of two phenyl rings connected by an alkylene bridge, there is either one imino group or one amino group on each phenyl ring. Also provided are processes for forming diimines and secondary diamines.Type: GrantFiled: September 14, 2007Date of Patent: August 3, 2010Assignee: Albemarle CorporationInventors: Paul L. Wiggins, Judit Orgad, John Y. Lee, Mahmood Sabahi
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Patent number: 7763758Abstract: The present invention relates to the field of catalytic hydrogenation and, more particularly, to the use of Ru complexes with bidentate ligands, having one amino or imino coordinating group and one phosphino coordinating group, in hydrogenation processes for the reduction of esters or lactones into the corresponding alcohol or diol respectively.Type: GrantFiled: September 12, 2007Date of Patent: July 27, 2010Assignee: Firmenich SAInventors: Lionel Saudan, Philippe Dupau, Jean-Jacques Riedhauser, Patrick Wyss
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Publication number: 20100160688Abstract: The present invention relates to linear amine-functionalized poly(trimethylene ether) compositions, and processes to produce these compositions.Type: ApplicationFiled: December 23, 2008Publication date: June 24, 2010Applicant: E.I. DU PONT DE NEMOURS AND COMPANYInventors: Kai Qi, Hari Babu Sunkara
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Patent number: 7737303Abstract: A method of selectively preparing a chiral 2S-amino alcohol useful in preparation of an amide sulfonated or acylated with alkyl, substituted aryl or substituted heteroaryl is described. The method involves reacting a di-tert-butyl diazene-1,2-dicarboxylate with a (4S)-4-benzyl-3-[(S)-trifluoromethyl-alkyl substituted alkanoyl]-1,3-oxazolidin-2-one to afford a di-tert-butyl 1-(1S,2S)-([(4S)-4-benzyl-2-oxo-1,3-oxazolidine-3-yl]-carbonyl}-trifluoromethyl-alkyl substituted alkyl)hydrazine-1,2-dicarboxylate. This dicarboxylate is then reduced to yield di-tert-butyl 1-(1S,2S)-[trifluoromethyl-alkyl substituted alkyl]hydrazine-1-(hydroxymethyl)-1,2-dicarboxylate. The resulting product is deblocked with an acid to yield the acid addition salt of (2S,3S)-trifluoro-hydrazino-methyl alkan-1-ol. The acid addition salt of (2S,3S)-trifluoro-2-hydrazino-methyl alkan-1-ol is hydrogenated in the presence of a suitable metal catalyst to yield the amino alcohol (2S,3S)-2-amino-trifluoro-methyl alkan-1-ol HCl.Type: GrantFiled: August 24, 2009Date of Patent: June 15, 2010Assignee: Wyeth LLCInventors: John Sellstedt, Gloria Cheal, Razzak Noureldin, Anita Wai-Yin Chan, Panolil Raveendranath, Thomas Joseph Caggiano
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Patent number: 7728175Abstract: The present invention relates to linear amine-functionalized poly(trimethylene ether) compositions, and processes to produce these compositions.Type: GrantFiled: December 23, 2008Date of Patent: June 1, 2010Assignee: E. I. du Pont de Nemours and CompanyInventors: Kai Qi, Hari Babu Sunkara
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Publication number: 20100048949Abstract: A compound having the formula (I) where each of R1, R2, R3 and R4 is independently C6-C18 aryl-, C5-C8 cycloalkyl-, C6-C18 aryl having at least one C1-C20 alkyl substituent, C5-C8 cycloalkyl having at least one C1-C20 alkyl substituent, C4-C20 branched alkyl-, C16-C20 linear alkyl-, RO—, —NRR?, —PRR?, —SR, fluoro substituted forms thereof, and perfluoro forms thereof: and R5 is C6-C18 aryl-, C5-C8 cycloalkyl-, C6-C18 aryl having at least one C1-C20 alkyl substituent, C5-C8 cycloalkyl having at least one C1-C20 alkyl substituent, C3-C20 branched alkyl-, C2-C30 linear alkyl-, fluoro substituted forms thereof, and perfluoro forms thereof; where R and R? are each independently C6-C18aryl-, C5-C8 cycloalkyl-, C6-C18 aryl having at least one C1-C20 alkyl substituent, C5-C8 cycloalkyl having at least one C1-C20 alkyl substituent, C4-C20 branched alkyl-, C2-C30 linear alkyl-, fluoro substituted forms thereof, and perfluoro forms thereof; A is N, P, S, or O with the proviso that when A is S, R2 is a nullify; and M isType: ApplicationFiled: November 14, 2007Publication date: February 25, 2010Applicant: STEPHAN CONSULTING CORPORATIONInventors: Douglas W. Stephan, Preston A. Chase, Gregory C. Welch
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Patent number: 7667058Abstract: Disclosed are heterogeneous processes (i) for the hydrogenation of a compound containing at least one unsaturated carbon-carbon bond, and (ii) for the hydro-dehalogenation of a compound containing at least one C—Cl, C—Br or C—I bond. The processes comprise reacting said compound with a hydrogenating agent and a heterogeneous hydrogenation catalyst in the presence of an ionic liquid.Type: GrantFiled: May 17, 2002Date of Patent: February 23, 2010Assignee: The Queen's University of BelfastInventors: Kris Anderson, Peter Goodrich, Christopher Hardacre, Sarah Elizabeth Jane McMath
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Publication number: 20100029990Abstract: Multi-step process for the preparation of compounds via hazardous intermediates comprising the steps of a) preparing in a microreactor a hazardous intermediate and b) optionally performing one or more reaction steps on the hazardous intermediate in one or more additional microreactors and c) further converting the hazardous intermediate with a suitable reaction agent in a subsequent microreactor until a stable end product is formed.Type: ApplicationFiled: May 23, 2007Publication date: February 4, 2010Inventors: Rafael Wilhelmus Elisabeth Ghislain Reintjens, Quirinus Bernardus Broxterman, Martina Kotthaus, Peter Poechlauer
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Publication number: 20100029976Abstract: The invention relates to a process for preparing tetraethylenepentamine (TEPA) by hydrogenation of diethylenetriaminediacetonitrile (DETDN) over a catalyst. If appropriate, DETDN can also be present as a constituent of an amino nitrile mixture which additionally comprises diethylenetriaminemonoacetonitrile (DETMN).Type: ApplicationFiled: February 27, 2008Publication date: February 4, 2010Applicant: BASF SEInventors: Kirsten Dahmen, Alfred Oftring, Randolf Hugo, Thilo Hahn, Katrin Baumann, Johann-Peter Melder
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Publication number: 20090264679Abstract: A process for the adjustment of a catalyst's or a catalyst precursor's suspension and settling properties, whereby the catalyst is treated with flocculants.Type: ApplicationFiled: December 14, 2004Publication date: October 22, 2009Inventors: Daniel Ostgard, Monika Berweiler, Barbara Bender
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Patent number: 7598422Abstract: A method of selectively preparing a chiral 2S-amino alcohol useful in preparation of an amide sulfonated or acylated with alkyl, substituted aryl or substituted heteroaryl is described. The method involves reacting a di-tert-butyl diazene-1,2-dicarboxylate with a (4S)-4-benzyl-3-[(S)-trifluoromethyl-alkyl substituted alkanoyl]-1,3-oxazolidin-2-one to afford a di-tert-butyl 1-(1S,2S)-([(4S)-4-benzyl-2-oxo-1,3-oxazolidine-3-yl]-carbonyl}-trifluoromethyl-alkyl substituted alkyl)hydrazine-1,2-dicarboxylate. This dicarboxylate is then reduced to yield di-tert-butyl 1-(1S,2S)-[trifluoromethyl-alkyl substituted alkyl]hydrazine-1-(hydroxymethyl)-1,2-dicarboxylate. The resulting product is deblocked with an acid to yield the acid addition salt of (2S,3S)-trifluoro-hydrazino-methyl alkan-1-ol. The acid addition salt of (2S,3S)-trifluor-2-hydrazino-methyl alkan-1-ol is hydrogenated in the presence of a suitable metal catalyst to yield the amino alcohol (2S,3S)-2-amino-trifluoro-methyl alkan-1-ol HCl.Type: GrantFiled: April 18, 2007Date of Patent: October 6, 2009Assignee: WyethInventors: John Sellstedt, Gloria Cheal, Razzak Noureldin, Anita Wai-Yin Chan, Panolil Raveendranath, Thomas Joseph Caggiano
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Patent number: 7595029Abstract: The invention pertains to an improved apparatus comprised of a monolith catalytic reactor having an inlet and an outlet and a static mixer having an inlet and an outlet thereto with the outlet of said static mixer in communication with the inlet of said monolith catalytic reactor. The invention also pertains to an improvement in a process for effecting a reaction in the monolith catalytic reactor wherein a reactant gas and reactant liquid are introduced to the inlet to the monolith catalytic reactor, reacted and, then, the reaction product passed through the outlet of the monolith catalytic reactor.Type: GrantFiled: February 1, 2005Date of Patent: September 29, 2009Assignee: Air Products and Chemicals, Inc.Inventors: Keith Allen Welp, Anthony Rocco Cartolano, David Joseph Parrillo, Richard Peter Boehme, Reinaldo Mario Machado, Sylvia Caram
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Publication number: 20090082599Abstract: In a process for the accelerated reduction of organic substrates, selected from the group consisting of esters, amides, nitriles, acids, ketones, imines or mixtures thereof, they are reacted with an amine borane, sulfide borane or ether borane complex as a borane source in the presence of organic accelerator compounds containing either Lewis acidic or Lewis basic sites in their structure, of which the Lewis acidic site can coordinate with the carbonyl or nitrile or imine group of the substrate or the Lewis basic site can coordinate with the borane.Type: ApplicationFiled: September 21, 2007Publication date: March 26, 2009Applicant: BASF AktiengesellschaftInventors: Elizabeth Burkhardt, Alex J. Attlesey, Christopher P. Sutton, Karl Matos
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Publication number: 20090082568Abstract: In a process for the accelerated reduction of organic substrates, selected from the group consisting of ester, amides, nitriles, acids, ketones, imines or mixtures thereof, the substrates are reacted with an amine borane, sulfide borane or ether borane complex as a borane source in the presence of organic accelerator compounds containing both Lewis acidic and Lewis basic sites in their structure, of which the Lewis acidic site can coordinate with the carbonyl or nitrile or imine group of the substrate and the Lewis basic site can coordinate with the borane.Type: ApplicationFiled: September 21, 2007Publication date: March 26, 2009Applicant: BASF AktiengesellschaftInventor: Elizabeth Burkhardt
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Patent number: 7291753Abstract: The invention relates to a process for the reduction of compounds comprising a carbon-carbon (C?C), carbon-oxygen (C?O), or carbon-nitrogen (C?N) double bond, to a corresponding hydrogenated alkane, alcohol or amine, comprising contacting a compound comprising the C?C, C?O or C?N double bond with a hydrogen donor solvent and a catalyst comprising a metal complex having a tridentate aminodiphosphine ligand under transfer hydrogenation conditions.Type: GrantFiled: November 10, 2004Date of Patent: November 6, 2007Inventor: Kamaluddin Abdur-Rashid
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Patent number: 7265237Abstract: Certain chiral monophosphites and their monothio derivatives are suitable as ligands in the asymmetrical transition-metal-catalyzed hydrogenation, hydroborination and hydrocyanation of prochiral olefins, ketones and imines.Type: GrantFiled: June 5, 2001Date of Patent: September 4, 2007Assignee: Studiengesellschaft Kohle mbHInventors: Manfred T. Reetz, Gerlinde Mehler, Andreas Meiswinkel
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Publication number: 20070197830Abstract: Processes for preparing amino alcohols or salts thereof and sulfonamide substituted alcohol compounds are provided. Desirably, the sulfonamide substituted alcohol compounds are heterocyclic sulfonamide trifluoroalkyl-substituted alcohol compounds or phenyl sulfonamide trifluoroalkyl-substituted alcohol compounds.Type: ApplicationFiled: February 15, 2007Publication date: August 23, 2007Applicant: WyethInventors: Anita Wai-Yin Chan, Jianxin Ren, Mousumi Ghosh, Arkadiy Rubezhov, Panolil Raveendranath, Joseph Zeldis
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Patent number: 7256311Abstract: A process is provided for the hydrogenation or asymmetric hydrogenation of dialkyl, alkylalkenyl and dialkenyl imines of formula (II) to provide amines of formula (III), wherein, (i) R1 and R2 are optionally substituted cyclic, linear or branched alkyl or alkenyl; R3 is a hydrogen atom, a hydroxy radical, optionally substituted C1 to C8 cyclic, linear or branched alkyl or alkenyl, optionally substituted aryl; or (ii) R1 is alkyl or alkenyl, R2 is alkyl or alkenyl and the two are linked together or with R3 to form one or more rings; using a catalytic system comprising a base and a ruthenium complex containing (1) a diamine and (2) a diphosphine ligand or monodentate phosphine ligands in hydrogenation and asymmetric hydrogenation processesType: GrantFiled: May 15, 2003Date of Patent: August 14, 2007Inventors: Kamaluddin Abdur-Rashid, Robert H. Morris
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Patent number: 7109378Abstract: The invention pertains to an improved apparatus comprised of a monolith catalytic reactor having an inlet and an outlet and a static mixer having an inlet and an outlet thereto with the outlet of said static mixer in communication with the inlet of said monolith catalytic reactor. The invention also pertains to an improvement in a process for effecting a reaction in the monolith catalytic reactor wherein a reactant gas and reactant liquid are introduced to the inlet to the monolith catalytic reactor, reacted and, then, the reaction product passed through the outlet of the monolith catalytic reactor.Type: GrantFiled: January 21, 2002Date of Patent: September 19, 2006Assignee: Air Products and Chemicals, Inc.Inventors: Keith Allen Welp, Anthony Rocco Cartolano, David Joseph Parrillo, Richard Peter Boehme, Reinaldo Mario Machado, Sylvia Caram
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Patent number: 6984759Abstract: Process for the perfluoropolyether preparation having reactive end groups —CH2NH2, —CHO, —CH2OH, by reduction of the corresponding perfluoropolyethers having —CN, —COCl, —CHO end groups by using gaseous hydrogen in the presence of a catalyst constituted by Pd, Rh, or Ru, supported on solid metal fluorides, at a temperature from 20° C. to 150° C. and under a pressure between 1 and 50 atm.Type: GrantFiled: July 31, 2003Date of Patent: January 10, 2006Assignee: Solvay Solexis S.p.A.Inventors: Antonella Di Meo, Rosaldo Picozzi, Claudio Tonelli
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Publication number: 20040267034Abstract: Disclosed are heterogeneous processes (i) for the hydrogenation of a compound containing at least one unsaturated carbon-carbon bond, and (ii) for the hydro-dehalogenation of a compound containing at least one C—Cl, C—Br or C—I bond. The processes comprise reacting said compound with a hydrogenating agent and a heterogeneous hydrogenation catalyst in the presence of an ionic liquid.Type: ApplicationFiled: July 30, 2004Publication date: December 30, 2004Inventors: Kris Anderson, Peter Goodrich, Christopher Hardacre, Sarah Elizabeth Jane McMath
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Patent number: 6800764Abstract: A process is provided for preparing chirally pure S-enantiomers of &agr;-amino acids comprising the steps of: a) preparing an organometallic reagent from an alkyl halide of the formula (R)2CH(CH2)nCH2X; b) adding the organometallic reagent to carbon dioxide to afford a carboxylic acid; c) activating the carboxylic acid with an acid chloride, phosphorus trichloride, acid anhydride, or thionyl chloride in the presence of a tertiary amine base; d) reacting the product of step c) with an alkali metal salt of S-4-benzyl-2-oxazolidinone; e) treating the product of step d) with a strong non-nucleophilic base to form an enolate anion; f) trapping the enolate anion with 2,4,6-triisopropylbenzenesulfonyl azide to afford an oxazolidinone azide; g) hydrolyzing the oxazolidinone azide with an aqueous base to afford an &agr;-azido acid; h) reducing the &agr;-azido acid to the &agr;-amino acid; and i) recrystallizing the &agr;-amino acid to the chirally pure &agr;-amino acid.Type: GrantFiled: November 26, 2002Date of Patent: October 5, 2004Assignee: WyethInventors: Anthony Frank Kreft, Madelene Miyoko Antane, Derek Cecil Cole, Dennis Martin Kubrak, Lynn Resnick, Joseph Raymond Stock, Zheng Wang
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Publication number: 20040181094Abstract: A method is provided for synthesizing substituted alkynes from an alkyne reactant and a nucleophile using rhenium (V) oxo complex as a catalyst. The alkyne reactant is substituted at the propargylic position with a leaving group susceptible to displacement by the nucleophile in a nucleophilic substitution reaction. The method involves contacting the alkyne reactant with a nucleophilic reactant in the presence of a catalytically effective amount of the rhenium (V) oxo complex. The method does not require activation of the leaving group or ionization of the nucleophilic reactant, and may be carried out in the presence of air and moisture. The invention is useful in synthesizing propargyl ethers, propargyl amines, and the like.Type: ApplicationFiled: March 11, 2003Publication date: September 16, 2004Inventor: F. Dean Toste
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Publication number: 20040063966Abstract: The catalysts of formula (II): [Ru(L)m(L′)wXY], wherein X and Y represent simultaneously or independently a hydrogen or halogen atom, a hydroxy group, or an alkoxy, carboxyl or other anionic radical, m is 1 or 2, w is 1 when m is 1 and w is 0 when m is 2, L is a phosphino-amine or phosphino-imine bidentate ligand and L′ a diphosphine, are useful for the hydrogenation of substrates having a carbon-hetero atom double bond.Type: ApplicationFiled: September 3, 2003Publication date: April 1, 2004Inventors: Valentin Rautenstrauch, Rene Challand, Eric Brazi, Hubert Mimoun, Kamaluddin Abdur-Rashid
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Patent number: 6683214Abstract: An amino group of an &agr;-amino acid ester is protected as an imine, and it is then reacted with a halomethyllithium to obtain an N-protected-&agr;-aminohalomethylketone. Further, this N-protected-&agr;-aminohalomethylketone is treated with an acid to obtain an &agr;-aminohalomethylketone. This process is suited for industrial production, and can produce an &agr;-aminohalomethylketone and its related compounds economically and efficiently.Type: GrantFiled: October 10, 2002Date of Patent: January 27, 2004Assignee: Ajinomoto Co., Inc.Inventors: Tomoyuki Onishi, Takashi Nakano, Naoko Hirose, Masakazu Nakazawa, Kunisuke Izawa
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Patent number: 6653507Abstract: There are disclosed are A diastereomer salt of formula (1): a process for producing the same, a process for producing optically active 3,3,3-trifluoro-2-hydroxy-2-methylpropionic acid of formula (2′): a novel optically active amine compound of formula (4): a novel optically active amine compound of formula (8): an imine compound of formula (7) or (11):Type: GrantFiled: May 20, 2002Date of Patent: November 25, 2003Assignee: Sumitomo Chemical Company, LimitedInventors: Miyuki Oikawa, Hideki Ushio, Isao Kurimoto, Takayuki Higashii
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Publication number: 20030199713Abstract: Catalyst for the asymmetric (transfer) hydrogenation represented by the formula MLaXbSc, where M is a transition metal, to be chosen from rhodium and ruthenium, and X is a counter ion and S is a ligand, a ranges from 0.5 to 3 and b and c, each independently, range from 0 to 2, and L is a chiral ligand having the formula (1), where Cn together with the two 2 O-atoms and the P-atom forms a substituted or non-substituted ring with 2-4 C-atoms, R1 and R2 each independently represent H, an optionally substituted alkyl, aryl, alkaryl or aralkyl group or may form a (heterocyclic) ring together with the N-atom to which they are bound. And a process for the asymmetric (transfer) hydrogenation of an olefinically unsaturated compound, ketone, imine or oxime derivate in the presence of a hydrogen donor and of a catalyst, use being made of a catalyst represented by formula MLaXbSc, where M is a transition metal, to be chosen from rhodium, iridium and ruthenium, X is a counter ion, S is a ligand, a ranges from 0.Type: ApplicationFiled: January 7, 2003Publication date: October 23, 2003Inventors: Michel Berg Van Den, Ben Feringa, Adriaan Jacobus Minnaard, Johannes Gerardus Vries De
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Publication number: 20030195369Abstract: A (R) or (S) chiral diphosphine of formula (I): 1Type: ApplicationFiled: January 31, 2003Publication date: October 16, 2003Applicant: PPG-SIPSYInventors: Michel Bulliard, Blandine Laboue, Sonia Roussiasse
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Publication number: 20030171608Abstract: Certain chiral monophosphites and their monothio derivatives are suitable as ligands in the asymmetrical transition-metal-catalyzed hydrogenation, hydroborination and hydrocyanation of prochiral olefins, ketones and imines.Type: ApplicationFiled: December 4, 2002Publication date: September 11, 2003Inventors: Manfred T Reetz, Gerlinde Mehler, Andreas Meiswinkel
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Publication number: 20030163003Abstract: Chiral ligands and transition metal complexes based on such chiral ligands useful in asymmetric catalysis are disclosed. The chiral ligands include phospholanes, P,N ligands, N,N ligands, biphenols, and chelating phosphines. The ferrocene-based irridium (R,R)-f-binaphane complex reduces imines to the corresponding amines with 95-99.6% enantioselectivity and reduces &bgr;-substituted-&agr;-arylenamides with 95% enantioselectivity.Type: ApplicationFiled: December 13, 2002Publication date: August 28, 2003Applicant: The Penn State Research FoundationInventors: Xumu Zhang, Dengming Xiao
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Publication number: 20030120088Abstract: There are disclosed an optically active azetidincarboxamide-coordinated transition metal complex of formula (1): 1Type: ApplicationFiled: December 11, 2002Publication date: June 26, 2003Inventors: Taichi Senda, Kazunori Iwakura, Naoto Konya
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Publication number: 20030065225Abstract: Catalysts useful for producing methylamines and having practical catalyst life and large selectivity for dimethylamine comprise crystalline silicoaluminophosphate molecular sieves which have a molar ratio of silicon atom to aluminum atom in the range of 0.01-0.30.Type: ApplicationFiled: July 10, 2002Publication date: April 3, 2003Applicant: Mitsubishi Gas Chemical Company, Inc.Inventors: Toshio Hidaka, Katsumi Higuchi, Takeshi Kawai
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Patent number: 6528687Abstract: A process for the preparation of an enantiomerically enriched chiral amine of formula (10), or the opposite enantiomer thereof, from an inline of formula (11) wherein (i) R1 is aryl, R2 is alkyl and R3 is aryl or aryl-CH2—, or (iii) R2 is linked with R1 and/or R3 to form one or more rings and R3 or R1 (if not in a ring) is H or a non-interfering organic group, the number of C atoms in each of R1, R2 and R3 being up to 30, comprises asymmetric hydrogenation of the imine in the presence of a base and, as catalyst, a ruthenium complex of a chiral diphosphine and a chiral diamine.Type: GrantFiled: July 23, 2001Date of Patent: March 4, 2003Assignee: Chirotech Technology LimitedInventors: Christopher James Cobley, Julian Paul Henschke, James Andrew Ramsden
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Patent number: 6500985Abstract: An amino group of an &agr;-amino acid ester is protected as an imine, and it is then reacted with a halomethyllithium to obtain an N-protected-&agr;-aminohalomethylketone. Further, this N-protected-&agr;-aminohalomethylketone is treated with an acid to obtain an &agr;-aminohalomethylketone. This process is suited for industrial production, and can produce an &agr;-aminohalomethylketone and its related compounds economically and efficiently.Type: GrantFiled: July 25, 2001Date of Patent: December 31, 2002Assignee: Ajinomoto Co., Inc.Inventors: Tomoyuki Onishi, Takashi Nakano, Naoko Hirose, Masakazu Nakazawa, Kunisuke Izawa
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Patent number: 6489373Abstract: The present invention provides a method of recovering a polyamine compound and/or a polyol compound useful for starting materials of polyurethane resin in an industrially advantageous manner by first dissolving the polyurethane resin such as polyurethane foams discharged in a large amount as industrial wastes in a solubilizing agent containing a polyamine compound, a low molecular glycol or an amino alcohol, hydrolyzing the resulting solution with liquid water at 200 to 320° C., then recovering the polyamino compound and/or polyol compound thus formed.Type: GrantFiled: October 1, 1999Date of Patent: December 3, 2002Assignee: Mitsui Takeda Chemicals Inc.Inventors: Katsuhisa Kodama, Kouichi Murayama, Takashi Kumaki
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Publication number: 20020156282Abstract: A catalytic transfer hydrogenation process is provided. The catalyst employed in the process is a metal cyclopentadienyl complex which is coordinated to defined bidentate ligands. Preferred metals include rhodium, ruthenium and iridium. Preferred bidentate ligands are diamines and aminoalcohols, particularly those comprising chiral centers. The hydrogen donor is advantageously a secondary alcohol or a mixture of triethylamine and formic acid. The process can be employed to transfer hydrogenate ketones and imines, which are preferably prochiral. Catalysts for use in such a process are also provided.Type: ApplicationFiled: February 27, 2002Publication date: October 24, 2002Applicant: Avecia LimitedInventors: Andrew John Blacker, Ben James Mellor