Preparing Directly By Dealkylation Patents (Class 564/486)
  • Patent number: 8766012
    Abstract: 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: Grant
    Filed: November 9, 2011
    Date of Patent: July 1, 2014
    Assignee: Bayer Cropscience AG
    Inventors: Norbert Lui, Christian Funke, Jens-Dietmar Heinrich, Thomas Norbert Müller
  • Patent number: 8415503
    Abstract: 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: Grant
    Filed: July 6, 2011
    Date of Patent: April 9, 2013
    Assignee: Agency for Defense Development
    Inventors: Eun Mee Goh, Jin Seuk Kim
  • Publication number: 20130018209
    Abstract: 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: Application
    Filed: March 17, 2011
    Publication date: January 17, 2013
    Applicant: Suzhou Zelgen Biopharmaceutical Co., Ltd.
    Inventors: Xiaoyong Gao, Weidong Feng, Xiaojun Dai
  • Patent number: 8124808
    Abstract: A method of transalkoxylation of nucleophilic compounds in which an alkoxylated and a nucleophilic compound are combined in a suitable vessel and reacted in the presence of a heterogeneous catalyst under conditions capable of transferring at least one hydroxyalkyl group from the alkoxylated compound to the nucleophilic compound. The method is especially useful in the transalkoxylation of alkanolamines to transfer a hydroxyalkyl group from an alkanolamine having a greater number of hydroxyalkyl groups to an alkanolamine having a lesser number of hydroxyalkyl groups.
    Type: Grant
    Filed: October 6, 2009
    Date of Patent: February 28, 2012
    Assignee: Union Carbide Chemicals & Plastics Technology LLC
    Inventors: Stephen W. King, William C. Hoffman
  • Publication number: 20110034732
    Abstract: 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: Application
    Filed: January 27, 2009
    Publication date: February 10, 2011
    Applicant: Central Glass Company, Limited
    Inventors: Akihiro Ishii, Takako Yamazaki, Manabu Yasumoto
  • Patent number: 7700805
    Abstract: An amine is prepared by cleaving a carbamate of the formula I wherein R1=hydrogen, alkyl, aryl or phenyl group, R2=alkyl, aryl or phenyl group, wherein R1 and R2 are independently substituted or unsubstituted, wherein the cleaving of the carbamate is performed in the presence of an acid of the formula II wherein R3, R4 and R5 are independently alkyl or phenyl group, wherein R1, R2, R3, R4 and R5 are the same or different.
    Type: Grant
    Filed: May 12, 2008
    Date of Patent: April 20, 2010
    Assignee: Evonik Degussa GmbH
    Inventors: Günther Köhler, Manfred Neumann, Marianne Omeis
  • Patent number: 7393979
    Abstract: 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: Grant
    Filed: June 8, 2004
    Date of Patent: July 1, 2008
    Assignee: Central Glass Company, Limited
    Inventors: Akihiro Ishii, Yokusu Kuriyama, Manabu Yasumoto, Masatomi Kanai, Kenjin Inomiya, Takashi Ootsuka, Koji Ueda
  • Patent number: 7115238
    Abstract: 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: Grant
    Filed: May 23, 2003
    Date of Patent: October 3, 2006
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Katsumi Higuchi, Akio Hashimoto, Toshihiro Nomura, Sachiko Arie, Takuo Ohshida, Takashi Kojima
  • Patent number: 7053246
    Abstract: Process for preparing a symmetrical secondary amine by reaction of a primary amine in the presence of hydrogen and a catalyst whose preparation has involved precipitation of catalytically active components onto monoclinic, tetragonal or cubic zirconium dioxide.
    Type: Grant
    Filed: December 10, 2003
    Date of Patent: May 30, 2006
    Assignee: BASF Aktiengesellschaft
    Inventors: Till Gerlach, Frank Funke, Christoph Benisch, Johann-Peter Melder
  • Patent number: 6773928
    Abstract: 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: Grant
    Filed: August 27, 2001
    Date of Patent: August 10, 2004
    Assignee: The United States of America as represented by the Secretary of the Army
    Inventors: Ray Yin, H. Dupont Durst, Peter A. Emanuel, Gary L. Hagnauer
  • Patent number: 6495724
    Abstract: 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: Grant
    Filed: April 27, 2000
    Date of Patent: December 17, 2002
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Toshio Hidaka, Katsumi Higuchi, Takeshi Kawai
  • Patent number: 6469214
    Abstract: A process for the preparation of one or more ethanolamines (I), chosen from the group consisting of monoethanolamine, diethanolamine and triethanolamine, by conversion of one or more ethanolamines (II) different from the ethanolamine(s) (I), chosen from the group consisting of monoethanolamine, diethanolamine, triethanolamine. O,N,N-tris(2-hydroxyethyl) ethanol-N-(2-aminoethyl)-ethanolamine, N-(2-amine, hydroxy ethyl) piperazine, N-(2-hydroxyethyl)morpholine and N,N′-bis(2-hydroxyethyl)piperazine, where the ethanolamine(s) (II), optionally in the presence of ammonia, is/are treated with a strong base.
    Type: Grant
    Filed: November 29, 2001
    Date of Patent: October 22, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Johann-Peter Melder, Gerhard Schulz
  • Patent number: 6417403
    Abstract: 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: Grant
    Filed: December 7, 2000
    Date of Patent: July 9, 2002
    Assignee: Samsung Fine Chemicals Co., Ltd.
    Inventors: Kyoung Rok Roh, Jung Hwan Lee, Dae Il Hwang, Won Jang Lee, Kyung-Il Kim
  • Patent number: 6294633
    Abstract: 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: Grant
    Filed: August 2, 2000
    Date of Patent: September 25, 2001
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Toshio Hidaka, Katsumi Higuchi
  • Patent number: 6166259
    Abstract: 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: Grant
    Filed: March 28, 2000
    Date of Patent: December 26, 2000
    Assignee: American Cyanamid Company
    Inventors: Rudi Eisenacht, Hans-Peter Niedermann, Dieter Landau
  • Patent number: 5274118
    Abstract: 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: Grant
    Filed: December 4, 1991
    Date of Patent: December 28, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: Robert T. Jacobs, Andrew G. Brewster, George J. Sependa
  • Patent number: 5116916
    Abstract: 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: Grant
    Filed: January 29, 1988
    Date of Patent: May 26, 1992
    Assignee: Union Oil Company of California
    Inventor: Donald C. Young
  • Patent number: 5105014
    Abstract: 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: Grant
    Filed: August 6, 1991
    Date of Patent: April 14, 1992
    Assignee: Mallinckrodt Medical, Inc.
    Inventor: William L. Neumann
  • Patent number: 4871874
    Abstract: 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: Grant
    Filed: June 15, 1987
    Date of Patent: October 3, 1989
    Assignee: Ethyl Corporation
    Inventor: Joachim W. Wolfram
  • Patent number: 4625064
    Abstract: 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: Grant
    Filed: April 6, 1984
    Date of Patent: November 25, 1986
    Assignee: Toyo Soda Manufacturing Co., Ltd.
    Inventors: Sadakatsu Kumoi, Keiji Mitarai, Yukihiro Tsutsumi
  • Patent number: 4492803
    Abstract: 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: Grant
    Filed: September 26, 1983
    Date of Patent: January 8, 1985
    Assignee: Toyo Soda Manufacturing Co., Ltd.
    Inventors: Sadakatsu Kumoi, Keiji Mitarai, Yukihiro Tsutsumi
  • Patent number: 4485261
    Abstract: 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: Grant
    Filed: April 9, 1982
    Date of Patent: November 27, 1984
    Assignee: Nitto Kagaku Kogyo Kabushiki Kaisha
    Inventors: Yoshiro Ashina, Michio Fukatsu
  • Patent number: 4405812
    Abstract: 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: Grant
    Filed: February 19, 1982
    Date of Patent: September 20, 1983
    Assignee: Ethyl Corporation
    Inventors: Walter K. Dean, Bernard R. Meltsner
  • Patent number: 4328370
    Abstract: 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: Grant
    Filed: March 15, 1979
    Date of Patent: May 4, 1982
    Assignee: The Dow Chemical Company
    Inventor: Michael J. Fazio