Preparing Directly By Dealkylation Patents (Class 564/486)
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Patent number: 8766012Abstract: A process for the preparation of 2,2-difluoroethylamine of the formula (I) CHF2CH2NH2??(I) comprising the stages (i) and (ii): stage (i): reaction of 2,2-difluoro-1-haloethane of the formula (II) CHF2—CH2Hal??(II) in which Hal is chlorine, bromine or iodine, with prop-2-en-1-amine of the formula (III) to give N-(2,2-difluoroethyl)prop-2-en-1-amine of the formula (IV) preferably in the presence of an acid scavenger, and stage (ii): removal of the allyl group from the N-(2,2-difluoroethyl)prop-2-en-1-amine of the formula (IV) obtained in stage (i) to give 2,2-difluoroethylamine of the formula (I) or a salt thereof.Type: GrantFiled: November 9, 2011Date of Patent: July 1, 2014Assignee: Bayer Cropscience AGInventors: Norbert Lui, Christian Funke, Jens-Dietmar Heinrich, Thomas Norbert Müller
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Patent number: 8415503Abstract: Disclosed is a method for preparation of 1,1-diamino-2,2-dinitroethylene (DADNE) through the hydrolysis of 4,6-dihydroxy-5,5-dinitro-2-(dinitromethylene)-2,5-dihydropyrimidine (DHDNDP) obtained by the nitration of 4,6-dihydroxy-2-methylpyrimidine (DHMP), which can avoid eruption or sudden frothing of a reaction solution on a lab scale and even a large scale preparation as well as reduce the reaction time.Type: GrantFiled: July 6, 2011Date of Patent: April 9, 2013Assignee: Agency for Defense DevelopmentInventors: Eun Mee Goh, Jin Seuk Kim
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Publication number: 20130018209Abstract: Preparation methods of methyl-d3-amine and salts thereof are provided, which contain the following steps: (i) nitromethane is subjected to react with deuterium oxide in the present of bases and phase-transfer catalysts to form nitromethane-d3, which is subsequently subjected to reduction in an inert solvent to form methyl-d3-amine, and optionally, methyl-d3-amine reacts subsequently with acids to form salts of methyl-d3-amine; or (ii) N-(1,1,1-trideuteriomethyl)phthalimide is subjected to react with acids to form salts of methyl-d3-amine. The present methods are easy, high efficient, and low cost.Type: ApplicationFiled: March 17, 2011Publication date: January 17, 2013Applicant: Suzhou Zelgen Biopharmaceutical Co., Ltd.Inventors: Xiaoyong Gao, Weidong Feng, Xiaojun Dai
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Patent number: 8124808Abstract: A method of transalkoxylation of nucleophilic compounds in which an alkoxylated and a nucleophilic compound are combined in a suitable vessel and reacted in the presence of a heterogeneous catalyst under conditions capable of transferring at least one hydroxyalkyl group from the alkoxylated compound to the nucleophilic compound. The method is especially useful in the transalkoxylation of alkanolamines to transfer a hydroxyalkyl group from an alkanolamine having a greater number of hydroxyalkyl groups to an alkanolamine having a lesser number of hydroxyalkyl groups.Type: GrantFiled: October 6, 2009Date of Patent: February 28, 2012Assignee: Union Carbide Chemicals & Plastics Technology LLCInventors: Stephen W. King, William C. Hoffman
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Publication number: 20110034732Abstract: Disclosed is a process for producing a protected optically active fluoroamine, which comprises the step of reacting an imine-protected optically active hydroxyamine, an oxazolidine-protected optically active hydroxyamine, or a mixture of the imine-protected optically active hydroxyamine and the oxazolidine-protected optically active hydroxyamine, with sulfuryl fluoride (SO2F2) in the presence of a tertiary amine having a carbon number of 7 to 18 (produced by substituting all of three hydrogen atoms in ammonia by alkyl groups). The desired optically active fluoroamine can be produced by hydrolyzing the protected optically active fluoroamine under acidic conditions.Type: ApplicationFiled: January 27, 2009Publication date: February 10, 2011Applicant: Central Glass Company, LimitedInventors: Akihiro Ishii, Takako Yamazaki, Manabu Yasumoto
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Patent number: 7700805Abstract: An amine is prepared by cleaving a carbamate of the formula I wherein R1=hydrogen, alkyl, aryl or phenyl group, R2=alkyl, aryl or phenyl group, wherein R1 and R2 are independently substituted or unsubstituted, wherein the cleaving of the carbamate is performed in the presence of an acid of the formula II wherein R3, R4 and R5 are independently alkyl or phenyl group, wherein R1, R2, R3, R4 and R5 are the same or different.Type: GrantFiled: May 12, 2008Date of Patent: April 20, 2010Assignee: Evonik Degussa GmbHInventors: Günther Köhler, Manfred Neumann, Marianne Omeis
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Patent number: 7393979Abstract: The present invention relates to a process for producing an optically active 1-alkyl-substituted 2,2,2-trifluoroethylamine, which is an important intermediate of medicines and agricultural chemicals, and which is represented by the formula [3] [in the formula R represents a lower alkyl group of a carbon and * represents an asymmetric carbon], or its salt by subjecting an optically active imine represented by the formula [1] to an asymmetric reduction under hydrogen atmosphere using a metal catalyst of Group VIII to convert it into an optically active secondary amine represented by the formula [2] and then by subjecting the secondary amine or its salt to hydrogenolysis. [Chem.Type: GrantFiled: June 8, 2004Date of Patent: July 1, 2008Assignee: Central Glass Company, LimitedInventors: Akihiro Ishii, Yokusu Kuriyama, Manabu Yasumoto, Masatomi Kanai, Kenjin Inomiya, Takashi Ootsuka, Koji Ueda
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Patent number: 7115238Abstract: Problems on catalyst production and catalyst performance with respect to conventional 8-oxygen-membered ring micropore-containing crystalline silicoaluminophosphate molecular sieves as non-equilibrium methylamine synthesis catalysts, are resolved. A chabazite type crystalline silicoaluminophosphate molecular sieve having high purity and high crystallinity and having, on a crystal grain surface, an amorphous oxide layer whose Si/Al atomic ratio is greater than that of the whole crystal grain can be stably produced with high yield with the use of a small amount of structure directing agents by the present method characterized in that hydrothermal treatment conducted in the production of 8-oxygen-membered ring micropore-containing crystalline silicoaluminophosphate sieves is controlled under specified treating conditions.Type: GrantFiled: May 23, 2003Date of Patent: October 3, 2006Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Katsumi Higuchi, Akio Hashimoto, Toshihiro Nomura, Sachiko Arie, Takuo Ohshida, Takashi Kojima
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Patent number: 7053246Abstract: Process for preparing a symmetrical secondary amine by reaction of a primary amine in the presence of hydrogen and a catalyst whose preparation has involved precipitation of catalytically active components onto monoclinic, tetragonal or cubic zirconium dioxide.Type: GrantFiled: December 10, 2003Date of Patent: May 30, 2006Assignee: BASF AktiengesellschaftInventors: Till Gerlach, Frank Funke, Christoph Benisch, Johann-Peter Melder
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Patent number: 6773928Abstract: Compositions of matter and methods for enhancing bioassay performance are disclosed. More particularly, the composition of matter comprises a molecularly compact polymer-ligand conjugate capable of self-orienting on a surface to improve the orientation of the ligand/receptor binding domains within the bioassay at the nanoscopic level. In a preferred embodiment, the molecularly compact polymer comprises a dendrimer polymer such as a fifth generation polyamidoamine dendrimer having exterior surface hydroxyl and amine functional groups, and the ligand/receptor comprises an antibody or Fab.Type: GrantFiled: August 27, 2001Date of Patent: August 10, 2004Assignee: The United States of America as represented by the Secretary of the ArmyInventors: Ray Yin, H. Dupont Durst, Peter A. Emanuel, Gary L. Hagnauer
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Patent number: 6495724Abstract: 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: GrantFiled: April 27, 2000Date of Patent: December 17, 2002Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Toshio Hidaka, Katsumi Higuchi, Takeshi Kawai
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Patent number: 6469214Abstract: A process for the preparation of one or more ethanolamines (I), chosen from the group consisting of monoethanolamine, diethanolamine and triethanolamine, by conversion of one or more ethanolamines (II) different from the ethanolamine(s) (I), chosen from the group consisting of monoethanolamine, diethanolamine, triethanolamine. O,N,N-tris(2-hydroxyethyl) ethanol-N-(2-aminoethyl)-ethanolamine, N-(2-amine, hydroxy ethyl) piperazine, N-(2-hydroxyethyl)morpholine and N,N′-bis(2-hydroxyethyl)piperazine, where the ethanolamine(s) (II), optionally in the presence of ammonia, is/are treated with a strong base.Type: GrantFiled: November 29, 2001Date of Patent: October 22, 2002Assignee: BASF AktiengesellschaftInventors: Johann-Peter Melder, Gerhard Schulz
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Patent number: 6417403Abstract: A process for the preparation of chiral (S)-2,3-disubstituted-1-propylamine derivatives, in which a carbonyl group of (S) 3,4-disubstituted-1-butanecarbonyl derivatives is converted to an amine group, and the conversion reaction is performed through Curtius rearrangement or Hoffman rearrangement.Type: GrantFiled: December 7, 2000Date of Patent: July 9, 2002Assignee: Samsung Fine Chemicals Co., Ltd.Inventors: Kyoung Rok Roh, Jung Hwan Lee, Dae Il Hwang, Won Jang Lee, Kyung-Il Kim
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Patent number: 6294633Abstract: Catalysts for producing methylamines are provided, which comprise mordenite, as the essential component, of spherical fine particles having a crystal diameter of not more than 0.5 &mgr;m. When the catalysts are used for the production of dimethylamine from methanol and ammonia or through a disproportionation of methylamines, they exhibit a high dimethylamine productivity with the formation of few amount of trimethylamine whose demand is very small. The process can be operated for a long period of time without decrease in the catalyst activity.Type: GrantFiled: August 2, 2000Date of Patent: September 25, 2001Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Toshio Hidaka, Katsumi Higuchi
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Patent number: 6166259Abstract: The invention relates to a process for the preparation of a 1,1,1-trifluoro-2-aminoalkane of formula I ##STR1## wherein R.sup.1 represents an optionally substituted alkyl group; which comprises heating a mixture consisting essentially of a compound of formula II ##STR2## wherein R.sup.1 has the meaning given, and R.sup.2 represents an optionally substituted aryl group, a primary amine, and optionally a base and/or an inert diluent, whereby the compound of formula I is removed by distillation during the heating procedure.Type: GrantFiled: March 28, 2000Date of Patent: December 26, 2000Assignee: American Cyanamid CompanyInventors: Rudi Eisenacht, Hans-Peter Niedermann, Dieter Landau
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Patent number: 5274118Abstract: A process for the preparation of (2R)-methyl-4,4,4-trifluorobutylamine, or an acid addition salt thereof which comprisesa) acylating an optically active amine with 2-methyl-4,4,4-trifluorobutanoic acid or a reactive derivative thereof to afford a butyramide;b) separating (R)-diastereomeric butyramide from (S)-diastereomeric butyramide; andc) converting the (R)-diastereomeric butyramide into the desired (2R)-methyl-4,4,4-trifluorobutylamine, or an acid addition salt thereof. The product may be acylated with a carboxylic acid of formula III ##STR1## wherein U is carboxy, or a reactive derivative thereof to afford (R)-4-[5-(N-[4,4,4-trifluoro-2-methylbutyl]carbamoyl)-1-methylindol-3-yl-m ethyl]-3-methoxy-N-o-tolylsulphonylbenzamide. The indole is useful as a leukotriene antagonist, for example in the treatment of asthma or allergic rhinitis.Type: GrantFiled: December 4, 1991Date of Patent: December 28, 1993Assignee: Imperial Chemical Industries PLCInventors: Robert T. Jacobs, Andrew G. Brewster, George J. Sependa
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Patent number: 5116916Abstract: Compositions containing sulfuric acid and one or more of certain chalcogen-containing compounds in which the chalcogen compound/H.sub.2 SO.sub.4 molar ratio is below 2 contain the mono-adduct of sulfuric acid which is catalytically active for promoting organic chemical reactions. Suitable chalcogen-containing compounds have the empirical formula ##STR1## wherein X is a chalcogen, each of R.sub.1 and R.sub.2 is independently selected from hydrogen, NR.sub.3 R.sub.4, and NR.sub.5, at least one of R.sub.1 and R.sub.2 is other than hydrogen, each of R.sub.3 and R.sub.4 is hydrogen or a monovalent organic radical, and R.sub.5 is a divalent organic radical. Such compositions are useful for catalyzing organic reactions such as oxidation, oxidative addition, reduction, reductive addition, esterification, transesterification, hydrogenation, isomerication (including racemization of optical isomers), alkylation, polymerization, demetallization of organometallics, nitration, Friedel-Crafts reactions, and hydrolysis.Type: GrantFiled: January 29, 1988Date of Patent: May 26, 1992Assignee: Union Oil Company of CaliforniaInventor: Donald C. Young
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Patent number: 5105014Abstract: The present invention relates to an improved method of forming vicinal diamines. The method according to the present invention has the advantage of being highly stereoselective, capable of forming a wide variety of diamines including racemic and enantiomeric forms, and employing readily available starting and reaction materials.In particular the present invention relates to a method of forming vicinal diamines from a bis-imine precursor using nucleophilic additions of organometallic reagents.Type: GrantFiled: August 6, 1991Date of Patent: April 14, 1992Assignee: Mallinckrodt Medical, Inc.Inventor: William L. Neumann
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Patent number: 4871874Abstract: Alkadienes are produced by reacting alkenyltrialkylammonium halide in which the double bond is allylic or homoallylic relative to the nitrogen atom with a strong inorganic base under phase transfer conditions. In this reaction trialkylamine is eliminated from the quaternary ammonium halide thereby resulting in the concurrent formation of the alkadiene. Long chain (e.g., C.sub.6 -C.sub.20) conjugated alkadienes, can readily be prepared from the corresponding alkenes in good yields on an economical basis by a three-stage process involving:(a) allylically monobrominating an alkene in the liquid phase;(b) converting the allylically monobrominated alkene into alkenyl quaternary ammonium bromide by reaction with a trialkyl amine; and(c) reacting the alkenyl quaternary ammonium bromide with a strong inorganic base under phase transfer conditions so that conjugated alkadiene and trialkylamine are formed.Type: GrantFiled: June 15, 1987Date of Patent: October 3, 1989Assignee: Ethyl CorporationInventor: Joachim W. Wolfram
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Patent number: 4625064Abstract: An improved process for preparing a bis [.beta.-(N,N-dimethylamino)ethyl]ether by reacting a bismethohalide of bis [.beta.-(N,N-dimethylamino)ethyl]ether represented by the following general formula: ##STR1## (wherein X denotes a halogen atom), with an aliphatic amine having a boiling point of not lower than 220.degree. C. at atmospheric pressure and having a primary amino group in the molecule thereof. The process comprises the following two steps (a) and (b): (a) a step of distilling out water at a temperature of not more than 130.degree. C. under reduced pressure from a mixture of said bismethohalide aqueous solution and said aliphatic amine to provide a concentration of said bismethohalide to water of not less than 85% by weight, and (b) a step of reacting said bismethohalide and amine in a solid-liquid phase at a temperature of not lower than 140.degree. C.Type: GrantFiled: April 6, 1984Date of Patent: November 25, 1986Assignee: Toyo Soda Manufacturing Co., Ltd.Inventors: Sadakatsu Kumoi, Keiji Mitarai, Yukihiro Tsutsumi
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Patent number: 4492803Abstract: A method for preparing a bis[.beta.-(N,N-dimethylamino)alkyl]ether by reacting a bismethohalide of bis[.beta.-(N,N-dimethylamino)alkyl]ether represented by the following general formula ##STR1## (wherein R and R' denote alkyl groups having 2-3 carbon atoms, and X denotes halogen atom,) with the aliphatic amine having 40.degree.-170.degree. C. of boiling point at atmospheric pressure and having one or two primary amino group in a molecule thereof at an increased pressure.Type: GrantFiled: September 26, 1983Date of Patent: January 8, 1985Assignee: Toyo Soda Manufacturing Co., Ltd.Inventors: Sadakatsu Kumoi, Keiji Mitarai, Yukihiro Tsutsumi
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Patent number: 4485261Abstract: Methylamines rich in dimethylamine are produced through two-step reaction of ammonia and methanol in which two types of catalysts are used and the methylamine mixture produced is recycled to the first step reaction.Type: GrantFiled: April 9, 1982Date of Patent: November 27, 1984Assignee: Nitto Kagaku Kogyo Kabushiki KaishaInventors: Yoshiro Ashina, Michio Fukatsu
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Patent number: 4405812Abstract: Ortho-methyl groups are preferentially removed from o-methyl substituted aromatic amines by contacting with a nickel catalyst at about 200.degree.-400.degree. C.Type: GrantFiled: February 19, 1982Date of Patent: September 20, 1983Assignee: Ethyl CorporationInventors: Walter K. Dean, Bernard R. Meltsner
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Patent number: 4328370Abstract: Lower trialkanolamines such as triethanolamine and triisopropanolamine are converted to the corresponding mono- and dialkanolamine by reacting with ammonia at about 150.degree. C.-275.degree. C. under superatmospheric pressure in the presence of a hydrogenation catalyst. The process is particularly useful for the recovery of alkanolamine values from still bottoms of alkanolamine production processes.Type: GrantFiled: March 15, 1979Date of Patent: May 4, 1982Assignee: The Dow Chemical CompanyInventor: Michael J. Fazio