Preparing Alicyclic Ring Containing Compound Directly By Amination Patents (Class 564/445)
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Patent number: 10343975Abstract: A process for fine purification of isophoronediamine (IPDA), including producing IPDA by aminating hydrogenation of isophorone nitrile in the presence of at least ammonia, hydrogen, a a hydrogenation catalyst and optionally further additions to obtain a crude IPDA, and subjecting the crude IPDA to a fine purification via two vacuum distillation columns, wherein in the first vacuum distillation column the removal of any remaining relatively low-boiling byproducts is effected and in the second vacuum distillation column the IPDA is obtained in pure form as tops and thus separated from the organic residues, and wherein the first vacuum distillation column has vacuum distillation column has a partial condenser fitted to it.Type: GrantFiled: March 30, 2017Date of Patent: July 9, 2019Assignee: Evonik Degussa GmbHInventors: Anne Rittsteiger, Alexander Martin Rüfer, Guido Streukens, Stephan Kohlstruk, Matthias Orschel, Matthias Mendorf, Jorn Walscharts, Axel Hengstermann, Anja Müller
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Patent number: 9035098Abstract: A process for conversion of aliphatic bicyclic amines to aliphatic diamines including contacting one or more bicyclic amines selected from the group consisting of 3-azabicyclo[3.3.1]nonane and azabicyclo[3.3.1]non-2-ene with ammonia and hydrogen, and alcohols in the presence of heterogeneous metal based catalyst systems, a metal selected from the group consisting of Co, Ni, Ru, Fe, Cu, Re, Pd, and their oxides at a temperature from 140° C. to 200° C. and a pressure from 1540 to 1735 psig for at least one hour reactor systems; forming a product mixture comprising aliphatic diamine(s), bicyclic amine(s), ammonia, hydrogen, and alcohol(s); removing said product mixture from the reactor system; removing at least some of the ammonia, hydrogen, water, alcohols, bicyclic amines from said product mixture; thereby separating the aliphatic diamines from said product mixture.Type: GrantFiled: July 30, 2010Date of Patent: May 19, 2015Assignee: Dow Global Technologies LLCInventors: Shawn D. Feist, Daniel A. Hickman, Erich J. Molitor, David C. Molzahn, Stacie Santhany, Abraham D. Schuitman
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Patent number: 8877976Abstract: The invention relates to an improved process for preparing 3-aminomethyl-3,5,5-trimethylcyclohexylamine, referred to hereinafter as isophoronediamine or IPDA for short, by means of catalytic hydrogenation and/or catalytic reductive amination (also referred to as aminating hydrogenation) of 3-cyano-3,5,5-trimethylcyclohexanone, also called isophoronenitrile or IPN for short hereinafter.Type: GrantFiled: November 17, 2011Date of Patent: November 4, 2014Assignee: Evonik Degussa GmbHInventors: Christian Lettmann, Guido Streukens, Matthias Orschel, Gerda Grund
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Publication number: 20140039181Abstract: 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: ApplicationFiled: December 28, 2012Publication date: February 6, 2014Applicant: Lanzhou Institute of Chemical Physics, Chinese Academy of SciencesInventor: Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences
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Patent number: 8592632Abstract: The present invention relates to a process for preparing a cyclic diamine, comprising the reaction of at least one cyclic alkene with a gas mixture (G) comprising dinitrogen the subsequent conversion of monoxide to give at least one cyclic ketone and then converting the at least one cyclic ketone to a cyclic diamine. The invention also relates to the use of a cyclic diamine with primary and secondary amine functions thus obtained to prepare polyamides and polyurethanes.Type: GrantFiled: November 6, 2009Date of Patent: November 26, 2013Assignee: BASF SEInventors: Kirsten Dahmen, Martin Ernst, Michael Limbach, Johann-Peter Melder, Beatrice Rössler-Feigel, Joaquim Henrique Teles
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Patent number: 8586793Abstract: Aldehyde or ketone compounds having more than one carbonyl group are reductively aminated to form a product amine compound having more than one primary amino group. The aldehyde or ketone compound is reacted with the product amine compound, to form a reaction mixture that contains one or more intermediates. The intermediate is then reductively aminated to form the desired product. This process produces the desired product in very high yields with low levels of secondary amine impurities.Type: GrantFiled: June 29, 2006Date of Patent: November 19, 2013Assignee: Dow Global Technologies LLCInventors: Michael Leo Tulchinsky, Barry B. Fish
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Publication number: 20130253226Abstract: The invention relates to an improved process for preparing 3-aminomethyl-3,5,5-trimethylcyclohexylamine, referred to hereinafter as isophoronediamine or, in abbreviated form, IPDA, by: I. preparation of isophorone by catalyzed aldol condensations with acetone as reactant; II. reaction of isophorone with HCN to form isophoronenitrile (IPN, 3-cyano-3,5,5-trimethylcyclohexanone); III. catalytic hydrogenation and/or catalytic reductive amination (also referred to as aminative hydrogenation) of 3-cyano-3,5,5-trimethylcyclohexanone, hereinafter called isophoronenitrile or, in abbreviated form, IPN, to give the isophoronediamine.Type: ApplicationFiled: November 18, 2011Publication date: September 26, 2013Applicant: Evonik Degussa GmbHInventors: Markus Galle, Gerda Grund, Axel Hengstermann, Michael D. Hinton, Rolf Hirsch, Robert Jansen, Cord Knoop, Christian Lettmann, Juergen Lippe, Martin Maier, Joerg-Joachim Nitz, Matthias Orschel, Martina Ortelt, Norbert Richter, Armin Rix, Markus Schwarz, Guido Streukens
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Patent number: 8529869Abstract: The present invention relates to a hydroamination catalyst comprising boron beta zeolites, wherein the hydroamination catalyst is doped with lithium, and also a process for producing it. The present patent application further relates to a process for preparing amines by reaction of ammonia or primary or secondary amines with olefins at elevated temperatures and pressures in the presence of the hydroamination catalyst of the invention.Type: GrantFiled: April 19, 2010Date of Patent: September 10, 2013Assignee: BASF SEInventors: Thomas Heidemann, Jens Kehrer
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Publication number: 20120277469Abstract: There are provided a method for producing N-alkyl-?-valienamine analogs represented by formula (I): (where R1 is a C1-12 alkyl group), and useful novel intermediates for the production method.Type: ApplicationFiled: December 24, 2010Publication date: November 1, 2012Inventor: Naoki Ota
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Publication number: 20120116122Abstract: The instant invention is a process for the conversion of aliphatic cyclic amines to aliphatic diamines. The process for conversion of aliphatic cyclic amines to aliphatic diamines comprises the steps of: (1) selecting one or more cyclic amines; (2) contacting said one or more cyclic amines with ammonia and hydrogen, optionally water, and optionally one or more solvents in the presence of one or more heterogeneous metal based catalyst systems at a temperature in the range of from 120° C. to about 250° C.Type: ApplicationFiled: July 30, 2010Publication date: May 10, 2012Applicant: Dow Global Technologies LLCInventors: Shawn D. Feist, Daniel A. Hickman, Erich J. Molitor, David C. Molzahn, Stacie Santhany, Abraham D. Schuitman
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Patent number: 8134030Abstract: A process for preparing a primary amine with a tertiary alpha-carbon atom by reacting a tertiary alcohol with ammonia in the presence of a heterogeneous catalyst, by performing the reaction in the presence of a non-microporous, non-zeolitic aluminosilicate as a catalyst, where the aluminosilicate has a molar Al/Si ratio in the range from 0.1 to 30.Type: GrantFiled: October 14, 2008Date of Patent: March 13, 2012Assignee: BASF SEInventors: Marcus Sigl, Thomas Heidemann
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Patent number: 7985881Abstract: Compositions and methods relating to aromatic imine compounds and methods of their use are described. The compounds are formed from aromatic aldehydes and amino or amino derivatives. The compounds and their derivatives are useful, for example, as hydrogen sulfide and mercaptan scavengers for use in both water and petroleum products.Type: GrantFiled: September 12, 2007Date of Patent: July 26, 2011Assignee: Guard Products LLCInventors: Gary Westlund, David Weller
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Patent number: 7790927Abstract: This invention relates to processes for the production of optically active 2-(disubstituted aryl)cyclopropylamine compounds and optically active 2-(disubstituted aryl)cyclopropane carboxamide compounds which are useful intermediates for the preparation of pharmaceutical agents, and in particular the compound [1S-(1?,2?,3?(1S*,2R*),5?)]-3-[7-[2-(3,4-difluorophenyl)-cyclopropyl]amino]-5-(propylthio)-3H-1,2,3-triazolo[4,5-d]pyrimidin-3-yl)-5-(2-hydroxyethoxy)-cyclopentane-1,2-diol.Type: GrantFiled: August 3, 2007Date of Patent: September 7, 2010Assignee: AstraZeneca ABInventors: Masaru Mitsuda, Tadashi Moroshima, Kentaro Tsukuya, Kazuhiko Watabe, Masahiko Yamada
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Patent number: 7683216Abstract: A process for the preparation of alkyleneimines by subjecting sulfuric acid monoesters of aminoalkanols to an at least two-stage reaction with aqueous bases at a temperature of at least 110° C. under pressure, relieving the pressure of the reaction mixture and distilling off the alkyleneimines from the reaction mixture after each reaction stage, wherein the conversion in the first stage is from 40 to 90% and that in the second stage is from more than 90% to 99.99%.Type: GrantFiled: April 18, 2008Date of Patent: March 23, 2010Assignee: BASF SEInventors: Thomas Knebel, Gerd Saas, Wolfgang Schreieck, Horst Schroeder, Manfred Winter
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Publication number: 20100041921Abstract: The invention relates to an improved process for preparing 3-aminomethyl-3,5,5-trimethylcyclohexylamine, referred to hereinafter as isophoronediamine or IPD for short, by aminating hydrogenation of 3-cyano-3,5,5-trimethylcyclohexanone, referred to hereinafter as isophoronenitrile or IPN for short, in the presence of a shaped Raney hydrogenation catalyst.Type: ApplicationFiled: January 25, 2008Publication date: February 18, 2010Applicant: EVONIK DEGUSSA GmbHInventors: Christian Lettmann, Gerda Grund, Juergen Lippe, Cord Knoop
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Patent number: 7456318Abstract: This present invention relates to a process for preparing benzylated amines by the reaction of an amine selected from methamphetamine and propylhexedrine with benzyl halide. Numerous improvements are obtained by employing the amine in molar excess with respect to benzyl halide, preferably in a molar ratio of 2 to 1. The excess amine is employed to selectively neutralize by-product acid as the amine salt. The amine salt is then separated from the reaction mixture and basified to reclaim starting amine for recycle to the process.Type: GrantFiled: November 2, 2005Date of Patent: November 25, 2008Assignee: Mallinckrodt Inc.Inventor: Dennis J. Kalota
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Publication number: 20080242861Abstract: This invention relates to methods of preparing the compounds of formula (V): Each variable in this formula is defined in the specification.Type: ApplicationFiled: April 2, 2007Publication date: October 2, 2008Inventors: Chi-Feng Yen, Chang-Pin Huang, Cheng-Kung Hu, Ming-Chen Chou, Chi-Hsin Richard King
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Patent number: 7355080Abstract: A new method of preparing memantine hydrochloride, comprising the following steps: reacting 1-bromo-3,5-dimethyl adamantane and urea/formic acid, with formic acid also acting as the solvent; hydrolyzing with aqueous inorganic acid; alkalifying, extracting and acidifying with hydrochloric acid; finally collecting target compound. The method uses inexpensive raw materials and is performed in homogeneous phase under mild conditions. It can achieve high yield and good product purity, and is suitable for macrochemistry. The purity of crude product is 99.0%, and reaches 99.98% after first recrystallization, yield: 69.5%, mp: 332 C (DSC).Type: GrantFiled: December 19, 2003Date of Patent: April 8, 2008Assignees: Shanghai Institute of Pharmaceutical Industry, Zhejiang Kangyu Pharmaceutical Co., Ltd.Inventors: Fuli Zhang, Meng Hu, Lizhi Zhao, Mengya Ge
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Patent number: 7317128Abstract: A process for preparing 3(4),8(9)-bis(aminomethyl)tricycle-[5.2.1.02,6]decane by hydroformylating dicyclopentadiene with subsequent reductive amination wherein the hydroformylation of dicyclopentadiene is carried out in two stages, and, in a first hydroformylation stage, the reaction is effected in a heterogeneous reaction system using an aqueous solution of transition metal compounds, containing water-soluble organic phosphorus (III) compounds in complex-bound form, of group VIII of the Periodic Table to give 8(9)-formyltricyclo[5.2.1.02,6]dec-3-ene, and, in a second hydroformylation stage, the thus obtained 8(9)-formyltricyclo[5.2.1.02,6]dec-3-ene is converted, in a homogeneous organic phase in the presence of transition metal compounds of group VIII of the Periodic Table of the Elements to 3(4),8(9)-bisformyltricyclo[5.2.1.Type: GrantFiled: October 18, 2004Date of Patent: January 8, 2008Assignee: Oxea Deutschland GmbHInventors: Peter Lappe, Helmut Springer, Rainer Lukas
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Patent number: 7235695Abstract: Conformationally restricted polyamine compounds useful in treatment of cancer and other diseases marked by abnormal cell proliferation are disclosed. Improved methods of synthesizing such compounds are also disclosed. In one method of the invention, a carbene-bearing or carbene equivalent-bearing compound is reacted with the double bond of an alkene compound to form a cyclopropyl ring as the first step in the synthesis.Type: GrantFiled: August 16, 2005Date of Patent: June 26, 2007Inventors: Benjamin Frydman, Aldonia L. Valasinas, Andrei V. Blokhin, Aparajita Sarkar, Hirak S. Basu, Venodhar K. Reddy, Laurence J. Marton, Yu Wang
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Patent number: 7038087Abstract: An object of the present invention is to provide a process for the production of an optically active amino alcohol, particularly an optically active amino alcohol of a trans-form, being excellent in economy and efficiency, and suitable for industry using easily available and less expensive materials. The present invention relates to a process for the production of an optically active amino alcohol comprising the steps that an optically active hydroxy ester in a trans-form obtained by an asymmetric hydrogenation of an easily available ?-keto ester is reacted with hydrazine, the resulting optically active hydrazinocarbonyl alcohol is subjected to a Curtius rearrangement in the presence of alcohol and protective group of amino group of the resulting optically active alkoxycarbonylamino alcohol is deprotected. As a result of the process for the production in accordance with the present invention, the objected substance is able to be prepared in a high optical purity and in a high yield.Type: GrantFiled: September 4, 2003Date of Patent: May 2, 2006Assignee: Takasago International CorporationInventors: Takahiro Fujiwara, Hideki Nara, Tsukasa Sotoguchi
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Patent number: 6982351Abstract: Conformationally restricted polyamine compounds useful in treatment of cancer and other diseases marked by abnormal cell proliferation are disclosed. Improved methods of synthesizing such compounds are also disclosed. In one method of the invention, a carbene-bearing or carbene equivalent-bearing compound is reacted with the double bond of an alkene compound to form a cyclopropyl ring as the first step in the synthesis.Type: GrantFiled: December 6, 2002Date of Patent: January 3, 2006Assignee: CellGate, Inc.Inventors: Benjamin Frydman, Aldonia L. Valasinas, Andrei V. Blokhin, Aparajita Sarkar, Hirak S. Basu, Venodhar K. Reddy, Laurence J. Marton, Yu Wang
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Patent number: 6891068Abstract: Disclosed is a one step method for preparing a ?-substituted sulfide by treating a ?-halosulfide with a nucleophile in water.Type: GrantFiled: March 19, 2003Date of Patent: May 10, 2005Assignee: Lexicon Pharmaceuticals, Inc.Inventors: Hartmuth C. Kolb, Zhi-Cai Shi, Zhi-Min Wang
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Patent number: 6828345Abstract: The invention relates to O-substituted 6-methyl-tramadol derivatives, to methods for producing them, to medicaments containing these compounds, to the use of O-substituted 6-methyl-tramadol derivatives for producing medicaments for treating pain and other symptoms or diseases, and to methods of treatment using the medicaments.Type: GrantFiled: March 31, 2003Date of Patent: December 7, 2004Assignee: Gruenenthal GmbHInventors: Helmut Buschmann, Babette-Yvonne Koegel, Elmar Friderichs, Dagmar Kaulartz
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Patent number: 6774270Abstract: A method of removing hexafluoropropylene dimers (“HFP dimers”), dimer hydrides and other oligomers from a fluid is described. The method comprises heating the fluid to isomerize the HFP dimers to the thermodynamic isomer, and contacting the fluid with a tertiary amine (or salts thereof) to form a hexafluoropropylene dimer—tertiary amine adduct. The method may further comprise the step of separating the dimer adducts from the reaction mixture.Type: GrantFiled: April 1, 2003Date of Patent: August 10, 2004Assignee: 3M Innovative Properties CompanyInventors: Zhongxing Zhang, Zai-Ming Qiu, Daniel R. Vitcak, Richard M. Flynn
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Patent number: 6723879Abstract: Disclosed is a process for the enantioselective production of an optically active amino compound by the amination of the C—H bond of an organic compound. The amino compound is produced by converting the C—H bond at the allyl position of an alkene or the C—H bond at the benzyl position of an alkylarene to the corresponding C—N bond, using a salen-manganese complex as the catalyst and N-substituted iminoaryliodinane as the amination agent. Both the catalytic activity and the enantioselectivity are very high when there is used a catalyst in which the 3- and 5-positions of the salicylaldehyde moiety of the salen ligand are substituted with an electron-withdrawing group, particularly with a halogen atom.Type: GrantFiled: November 7, 2002Date of Patent: April 20, 2004Assignee: Japan Science and Technology CorporationInventors: Tsutomu Katsuki, Yoshinori Kohmura
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Patent number: 6540793Abstract: Couplers for hair coloring compositions for oxidative dyeing of hair are compounds of the formula (1): wherein R is selected from the group consisting of C1 to C2 alkyl and hydroxyethyl; R1 is selected from the group consisting of a hydrogen, hydroxy, nitro, halogen, C1 to C5 alkyl or haloalkyl, C1 to C5 alkoxy or cycloalkoxy, C1 to C5 hydroxyalkyl and C1 to C5 hydroxyalkoxy; Ar is an aromatic group, preferably an aromatic group selected from the group consisting of a furyl, thienyl, pyridyl, phenyl, 2,3-dihydro-benzo[1,4]dioxin-5 or -6-yl or benzo[1,3]dioxol-4 or -5-yl group; and y=1 to 3.Type: GrantFiled: December 7, 2000Date of Patent: April 1, 2003Assignee: Clairol IncorporatedInventors: Mu-lll Lim, Linas R. Stasaitis, Yuh-Guo Pan
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Publication number: 20020188158Abstract: A method for preparing lithium amide is described in which in a first method step lithium metal is reacted with ammonia to form lithium bronze and in a second method step the lithium bronze is reacted with a 1,3-diene or an arylolefin in the presence of a solvent.Type: ApplicationFiled: March 5, 2002Publication date: December 12, 2002Inventors: Wilfried Weiss, Dirk Dawidowski
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Patent number: 6423871Abstract: A method for selective mono-N-alkylation of primary amines to produce secondary amines that are substantially free of overalkylated tertiary amines and quaternary ammonium salts, under mild reaction conditions without the necessity of protecting groups. Compounds of the class of secondary amines are produced by reacting an alkyl halide with an alkyl amine in anhydrous solvent, preferably dimethyl sulfoxide or N,N-dimethylformamide, in the presence of 0.1 to 3 molar equivalents of a cesium base. Optionally, the extent and selectivity of mono-N-alkylation is enhanced by addition to the reaction mixture of a powdered molecular sieve material for removal of water produced by the reaction, and/or tetrabutylammonium iodide to promote halide exchange. The invention permits selective and efficient mono-N-alkylation of a wide variety of substrates at 23° C.Type: GrantFiled: February 25, 2000Date of Patent: July 23, 2002Assignee: University of South FloridaInventor: Kyung Woon Jung
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Patent number: 6414207Abstract: A catalyst comprising at least one alkali metal and at least one metallic or semimetallic promoter selected from the group consisting of Ca, Sr, Ba, Ag, Au, Zn, Cd, Hg, In, Tl, Sn, As, Sb and Bi, on a support which may be doped with one or more compounds of an alkali metal and/or alkaline earth metal, where the alkali metal/support ratio by weight is from 0.01 to 5, the promoter/alkali metal ratio by weight is from 0.0001 to 5 and, when a dopant is present, the dopant/support ratio by weight is from 0.01 to 5.Type: GrantFiled: June 20, 2001Date of Patent: July 2, 2002Assignee: BASF AktiengesellschaftInventors: Ulrich Steinbrenner, Eugen Gehrer
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Patent number: 6403834Abstract: The invention concerns a method for preparing tris(ether-amines) of formula (I): N[A—O—(B—O)n—R]3 wherein R, A, B and n are as defined in Claim 1, comprising the reaction, in liquid phase, of an alkylene-glycol monoether of formula (II): HO—A—O—(B—O)nR wherein R, A, B and n are as defined in Claim 1, with an ammonolysis agent selected among ammonia and an etheramine of formula (I′): H3-pN[A—O—(B—O)nR]p wherein: A, B, n and R are as defined in Claim 1 and p represent 1 or 2, at a temperature ranging between 100 and 250° C., by contacting reagents with a hydrogenation-dehydrogenation catalyst.Type: GrantFiled: July 23, 2001Date of Patent: June 11, 2002Assignee: Rhodia ChimieInventors: Michel Alas, Albert Bouniot
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Patent number: 6362373Abstract: The disclosed invention comprises a compound having the formula: in which R1 and R2 independently represent a hydrogen or an alkyl group of 4 carbon atoms or greater. Further disclosed is a process for the preparation of the disclosed chiral amino alcohols from a starting amine compound and a limonene oxide.Type: GrantFiled: September 13, 2000Date of Patent: March 26, 2002Assignees: The Dow Chemical CompanyInventors: Christian T. Goralski, Bakthan Singaram, William Chrisman
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Patent number: 6353136Abstract: Aromatic amines of the formula (I) Ar—[NR6R7]n (I) are prepared by reacting a haloaromatic of the formula (II) Ar—Hal (II) with an amine of the formula (III) R6R7NH (III) in the presence of a palladaphosphacyclobutane and a base and in the presence or absence of an ionic halide in a solvent at temperatures of from 20 to 200° C.Type: GrantFiled: September 8, 2000Date of Patent: March 5, 2002Assignee: Clariant GmbHInventors: Holger Geissler, Steffen Haber, Stefan Scherer, Andreas Meudt, Frank Vollmueller
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Patent number: 6166234Abstract: Novel tripodal cyclopentadiene derivatives have the formula (I) ##STR1## where E are identical or different and are --N(R)(R), --P(R)(R), --As(R)(R), --Sb(R)(R), --OR, --SR, --SeR, --TeR, where R are identical or different and are each hydrogen, a C.sub.1 -C.sub.20 -carboorganic radical or a C.sub.1 -C.sub.30 -organosilicon radical, or E is a leaving group X andR.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 are identical or different and are each hydrogen, a C.sub.1 -C.sub.20 -carboorganic radical or a C.sub.1 -C.sub.30 -organosilicon radical,Z is a cyclopentadienyl radical or a substituted cyclopentadienyl structural unit andT is hydrogen, a C.sub.1 -C.sub.20 -carboorganic radical or a C.sub.1 -C.sub.30 -organosilicon radical or a group E--Y--, where E is --N(R)(R), --P(R)(R), --As(R)(R), --Sb(R)(R), --OR, --SR, --SeR, --TeR or a leaving group X, where R are identical or different and are each hydrogen, a C.sub.1 -C.sub.20 -carboorganic radical or a C.sub.1 -C.sub.Type: GrantFiled: January 13, 1998Date of Patent: December 26, 2000Assignee: BASF AktiengesellschaftInventors: Gottfried Huttner, Joachim Vogelgesang, Ute Winterhalter, Bjorn Antelmann
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Patent number: 6143934Abstract: In a process for preparing amines of the general formula I ##STR1## where R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 are hydrogen, C.sub.1 -C.sub.20 -alkyl, C.sub.2 -C.sub.20 -alkenyl, C.sub.2 -C.sub.20 -alkynyl, C.sub.3 -C.sub.20 -cycloalkyl, C.sub.4 -C.sub.20 -alkylcycloalkyl, C.sub.4 -C.sub.20 -cycloalkylalkyl, aryl, C.sub.7 -C.sub.20 -alkylaryl or C.sub.7 -C.sub.20 -aralkyl,R.sup.1 and R.sup.2 are together a saturated or unsaturated, divalent C.sub.3 -C.sub.9 -alkylene chain andR.sup.3 and R.sup.5 are each C.sub.21 -C.sub.200 -alkyl, C.sub.21 -C.sub.200 -alkenyl or together are a divalent C.sub.2 -C.sub.12 -alkylene chain,by reacting olefins of the general formula II ##STR2## where R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are as defined above, with ammonia or primary or secondary amines of the general formula III ##STR3## where R.sup.1 and R.sup.2 are as defined above, at from 200 to 350.degree. C.Type: GrantFiled: January 20, 1998Date of Patent: November 7, 2000Assignee: BASF AktiengesellschaftInventors: Uwe Dingerdissen, Rudolf Kummer, Peter Stops, Ulrich Muller, Jurgen Herrmann, Karsten Eller
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Patent number: 6043393Abstract: The present invention relates to a process for preparing cyclopropylamines of the formula ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, and R.sup.5 have specified meanings, by reacting(1) a carboxamide of the formula ##STR2## wherein R.sup.1, R.sup.2, and R.sup.3 have specified meanings, with(2) an olefin of the formula ##STR3## wherein R.sup.4, R.sup.5, and R.sup.6 have specified meanings, (3) alkylmagnesium halides or zinc alkyl compounds of the formulaR.sup.8 --X (VIII),wherein R.sup.8 has a specified meaning and X represents MgCl, MgBr, Mgl, ZnCl, ZnBr, Znl, or ZnR.sup.8, and(4) orthometallates of the formula (IX) ##STR4## wherein R.sup.9 has a specified meaning, Y represents Ti, Zr, or V.dbd.O, and Z represents chlorine, bromine, or C.sub.1 -C.sub.4 -alkyl,with the provisos that when is Y os Ti or Zr, then is 3 or 4 and r are zero or 1 and the sum q+r=4, and that when Y is V.dbd.O, then q represents 3 and r represents zero.Type: GrantFiled: May 6, 1999Date of Patent: March 28, 2000Assignee: Bayer AktiengesellschaftInventors: Armin de Meijere, Vladimir Chaplinski, Alexandre Kourdioukov
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Patent number: 6011179Abstract: A process for the production of primary and/or secondary amines from imines or nitriles, comprising an aminating hydrogenation of imine or of nitrile with hydrogen in the presence of ammonia, of a hydrogenation catalyst based on cobalt, nickel, ruthenium or mixtures of these metals and of a base, at a temperature within the range of 50.degree. C. to 200.degree. C. and at a pressure within the range of 0.3 to 30 MPa. The yield of amine is increased by the use of a quaternary ammonium hydroxide as base. Preferably a tetraalkylammonium hydroxide is used in a quantity of from 0.01 to 100 mMol per mol of amine or of nitrile. The process is suitable in particular for the production of isophoronediamine from isophorone nitrile imine.Type: GrantFiled: October 30, 1998Date of Patent: January 4, 2000Assignee: Degussa-Huls AGInventors: Thomas Haas, Karl Ludwig Weber, Klaus Stadtmuller, Willi Hofen, Rudolf Vanheertum
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Patent number: 5874621Abstract: Amines of the general formula I ##STR1## where R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 : are each hydrogen, C.sub.1 -C.sub.20 -alkyl, C.sub.2 -C.sub.20 -alkenyl, C.sub.2 -C.sub.20 -alkynyl, C.sub.3 -C.sub.20 -cycloalkyl, C.sub.4 -C.sub.20 -alkylcycloalkyl, C.sub.4 -C.sub.20 -cycloalkylalkyl, aryl, C.sub.7 -C.sub.20 -alkylaryl or C.sub.7 -C.sub.20 -aralkyl,R.sub.1 and R.sup.2 together are a saturated or unsaturated C.sub.3 -C.sub.9 -alkylene chain andR.sup.3 or R.sup.5 is C.sub.21 -C.sub.200 -alkyl or C.sub.21 -C.sub.200 -alkenyl or R.sup.3 and R.sup.5 together are a C.sub.2 -C.sub.12 -alkylene chain,are prepared by reacting an olefin of the general formula II ##STR2## where R.sup.3, R.sup.4, R.sup.5 and R.sup.6 have the abovementioned meanings, with ammonia or a primary or secondary amine of the general formula III ##STR3## where R.sup.1 and R.sup.2 have the abovementioned meanings, at from 200.degree.0 to 350.degree. C.Type: GrantFiled: February 12, 1998Date of Patent: February 23, 1999Assignee: BASF AktiengesellschaftInventors: Karsten Eller, Rudolf Kummer, Matthias Dernbach, Hans-Jurgen Lutzel
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Patent number: 5801202Abstract: Disclosed is an amine derivative represented by the following formula (1) or an acid addition salt thereof: ##STR1## wherein R.sup.1 represents a group ##STR2## a cyclopentyl group, cyclohexyl group, or a cycloheptyl group, R.sup.2 is a hydrogen atom or C1-C3 alkyl group which may be substituted by one or more hydroxyl groups, m is an integer falling in the range from 3 to 5 inclusive, and n is an integer falling in the range from 9 to 11 inclusive. Also, intermediates useful in the manufacture of the amine derivative (1), compositions for external application to the skin containing the amine derivative, and keratinization improvers containing the amine derivative as an active component are described. The compound (1) has excellent keratinization improving action, pigmentation preventing action, etc.Type: GrantFiled: May 30, 1997Date of Patent: September 1, 1998Assignee: Kao CoprorationInventors: Taketoshi Fujimori, Hiroshi Kusuoku, Akira Yamamuro, Yukihiro Yada, Kazuhiko Higuchi, Genji Imokawa, Naoki Kondo, Yoshinori Masukawa, Hajime Tokuda, Hisashi Tsujimura
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Patent number: 5786405Abstract: Clear, amine-initiated polyether polyols are made by epoxidizing an amine in the presence of an alkali metal hydroxide catalyst. After the desired degree of epoxidation has been achieved, a hydroxy-carboxylic acid is added to the epoxidized mixture in an amount sufficient to neutralize any remaining alkali metal hydroxide. The polyols produced in this manner are particularly useful for the production of polyurethane and apolyisocyanurate foams.Type: GrantFiled: November 1, 1996Date of Patent: July 28, 1998Assignee: Bayer CorporationInventors: Steven L. Schilling, Herman P. Doerge, Lotar H. Hanusa
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Patent number: 5773660Abstract: A process for preparing amines of the formula I ##STR1## where R.sup.1,R.sup.2,R.sup.3,R.sup.4,R.sup.5 and R.sup.6 are each hydrogen, C.sub.1 -C.sub.20 -alkyl, C.sub.2 -C.sub.20 -alkenyl, C.sub.2 -C.sub.20 -alkynyl, C.sub.3 -C.sub.20 -cycloalkyl, C.sub.4 -C.sub.20 -alkylcycloalkyl, C.sub.4 -C.sub.20 -cycloalkylalkyl, aryl, C.sub.7 -C.sub.20 -alkylaryl or C.sub.7 -C.sub.20 -aralkyl,R.sup.1 and R.sup.2 are together a saturated or unsaturated C.sub.3 -C.sub.9 -alkylene dichain, andR.sup.3 or R.sup.5 is C.sub.21 -C.sub.200 -alkyl or C.sub.21 -C.sub.200 -alkenyl or together they are a C.sub.2 -C.sub.12 -alkylene dichain,by reacting olefins of the formula II ##STR2## where R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are each as defined above, with ammonia or primary or secondary amines of the formula III ##STR3## where R.sup.1 and R.sup.2 are each as defined above, at temperatures from 200.degree. to 350.degree. C.Type: GrantFiled: January 21, 1997Date of Patent: June 30, 1998Assignee: BASF AktiengesellschaftInventors: Karsten Eller, Rudolf Kummer, Eugen Gehrer
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Patent number: 5763668Abstract: Amines are prepared by reacting a mixture obtained in the cracking of mineral oil fractions with ammonia or a primary or secondary amine of the general formula I ##STR1## where R.sup.1 and R.sup.2 are each hydrogen, C.sub.1 -C.sub.20 -alkyl, C.sub.2 -C.sub.20 -alkenyl, C.sub.2 -C.sub.20 -alkynyl, C.sub.3 -C.sub.20 -cycloalkyl, C.sub.4 -C.sub.20 -alkylcycloalkyl, C.sub.4 -C.sub.20 -cycloalkylalkyl, aryl, C.sub.7 --C.sub.20 -alkylaryl or C.sub.7 --C.sub.20 -aralkyl or together are a saturated or unsaturated C.sub.2 -C.sub.12 -alkylene ene chain,at from 200.degree. to 350.degree. C.Type: GrantFiled: July 3, 1996Date of Patent: June 9, 1998Assignee: BASF AktiengesellschaftInventors: Uwe Dingerdissen, Jurgen Herrmann, Karsten Eller
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Patent number: 5739397Abstract: Secondary amines having a hydrocarbon backbone, a functionality of at least 1 and a molecular weight of at least 74 are produced by reacting a hydrocarbon containing a leaving group with a primary amine, primary diamine, primary polyamine or ammonia at a temperature of from about 70.degree. to 250.degree. C.Type: GrantFiled: May 30, 1996Date of Patent: April 14, 1998Assignee: Bayer CorporationInventors: Rick L. Adkins, William E. Slack
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Patent number: 5693864Abstract: Disclosed herein is a process for preparing an amine terminated polyether comprising reacting a polyether containing a leaving group with a primary amine or ammonia at a temperature of about 70 to 250 degrees Centigrade.Type: GrantFiled: October 7, 1992Date of Patent: December 2, 1997Assignee: Bayer CorporationInventors: William E. Slack, Rick L. Adkins, Hans Georg Schmelzer
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Patent number: 5684132Abstract: The present invention relates to a process for preparing protected amines or amino acids. The invention furthermore relates to the use of tocopheryl radicals or radicals derived therefrom as protective groups for amines and amino acids, and to compounds obtained in this process as intermediates and to processes for preparing dipeptides and oligopeptides.Type: GrantFiled: December 4, 1995Date of Patent: November 4, 1997Assignee: BASF AktiengsellschaftInventors: Thomas Rosenau, Wolf-Dieter Habicher, Chen-Loung Chen
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Patent number: 5504254Abstract: A process is disclosed for the continuous preparation of 3-aminomethyl-3,5,5-trimethylcyclohexylamine (isophoronediamine) in high yield and high purity from 3-cyano-3,5,5-trimethylcyclohexanone (isophoronenitrile) by aminating hydrogenation with hydrogen and ammonia in the presence of a fixed bed catalyst. The aminating hydrogenation is carried out by allowing a mixture of isophoronenitrile, ammonia and a C.sub.1 -C.sub.3 -alcohol, in the presence of hydrogen, to trickle over a trickle bed reactor provided with a Co and/or Ru fixed bed catalyst, at 3 to 8 MPa and at a temperature of 40.degree. to 150.degree. C., preferably 90 to 130.degree. C., and working up the reaction mixture by distillation. Preferably, a high-boiling by-product fraction, containing a bicyclic amidine, is added to the mixture to be hydrogenated, thereby appreciably increasing the yield.Type: GrantFiled: December 22, 1994Date of Patent: April 2, 1996Assignee: Degussa AktiengesellschaftInventors: Thomas Haas, Dietrich Arntz, Dieter Most
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Patent number: 5440049Abstract: A compound of the formula: ##STR1## wherein R.sup.11 is hydrogen, lower alkyl, haloloweralkyl, lower alkenyl, lower alkynyl or cycloalkyl and R.sup.21 is a group selected from the group consisting of: ##STR2## wherein R.sup.3 -R.sup.5, R.sup.31, R.sup.32, R.sup.41, R.sup.42 and R.sup.51 are as defined herein, and W is chlorine or bromine, is prepared by reacting a compound of the formula:Z--CH.sub.2 --CH.dbd.CH--W (I)wherein W is as defined above and Z is a leaving group, with an amine of the formula: ##STR3## wherein R.sup.11 and R.sup.21 are as defined above.Type: GrantFiled: June 13, 1994Date of Patent: August 8, 1995Assignee: Banyu Pharmaceutical Co., Ltd.Inventors: Susumu Nakagawa, Akira Asai, Satoru Kuroyanagi, Makoto Ishihara, Yoshiharu Tanaka
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Patent number: 5405998Abstract: There is provided an improved method for the production of o-aminophenyl ketones of formula I wherein R is C.sub.3 -C.sub.6 cycloalkyl or C.sub.1 -C.sub.6 haloalkyl. ##STR1## Compounds of formula I are key intermediates in the manufacture of sulfamoyl urea herbicides.Type: GrantFiled: November 30, 1993Date of Patent: April 11, 1995Assignee: American Cyanamid CompanyInventor: Albert A. Cevasco
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Patent number: 5347053Abstract: This invention relates to an improvement in a process for producing an alkylamine from olefin and amine by hydrohalogenating the olefin to form haloalkane then reacting the haloalkane with amine to form an alkylamine. The improvement comprises heat-treating the alkylamine thus formed with an aqueous alkaline or alkaline earth metal hydroxide at a temperature and for a period of time sufficient to minimize the formation of flocculent precipitate during the formation and/or storage of the alkylamine.Type: GrantFiled: November 4, 1992Date of Patent: September 13, 1994Assignee: Albemarle CorporationInventors: Bonnie G. McKinnie, W. Brian Harrod
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Patent number: 5344990Abstract: Intermediates and a process for their preparation are disclosed which are useful for the preparation of a renin inhibiting compound of the formula: ##STR1## wherein R is a nitrogen-containing heterocycle which is bonded via a nitrogen atom to the sulfonyl group, R.sub.6 is hydrogen, alkoxy, halogen or loweralkyl, R.sub.7 is loweralkyl having 2 to 7 carbon atoms, and R.sub.8 is loweralkyl, cycloalkyl, or aryl or a pharmaceutically acceptable acid addition salt thereof.Type: GrantFiled: October 5, 1993Date of Patent: September 6, 1994Assignee: Abbott LaboratoriesInventors: William R. Baker, Stephen L. Condon