Preparing Directly From Hetero Ring Containing Compound Patents (Class 564/487)
  • Publication number: 20080261814
    Abstract: The present invention generally relates to a process for preparing the alkoxylated alkylamines and/or alkyl ether amines. The process consists of three stages, and utilizes an alkali catalyst. The alkoxylated alkyl amines and alkoxylated alkyl ether amines prepared by the process possess the peaked distribution and contain less hazardous by-product.
    Type: Application
    Filed: September 23, 2005
    Publication date: October 23, 2008
    Applicants: MONSANTO TECHNOLOGY LLC, AKZO NOBEL N.V.
    Inventors: Shawn Zhu, Giao Nguyen, Kha Nguyen, Alberto Slikta, David Eaton, David Becher, Henry Agbaje, Michael Seitz
  • Patent number: 7432399
    Abstract: A polyol monomer comprising the formula: R1 and R3 are —H, aliphatic, aromatic, or ether; R2 is aliphatic, aromatic, ester, ether, or acrylic, and R1 contains a hydroxyl group, R3 contains a hydroxyl group, R2 contains —O—CH2—CH(OH)—, or any combination thereof. The polyol monomer may be made by reacting an epoxy and an amine. Either the epoxy contains more than one epoxide groups, the amine contains a hydroxyl group, or both. A thermoset made by reacting the polyol monomer with a polyisocyanate.
    Type: Grant
    Filed: November 2, 2004
    Date of Patent: October 7, 2008
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Jozef Verborgt, Arthur Anthony Webb
  • Patent number: 7307184
    Abstract: The present invention provides a process of starting from N-alkoxycarbonyl-ethylamine compounds having a leaving group at the ?-position to prepare oxazolidinone derivatives of ?-hydroxyethylamine compounds having an inverted steric configuration at the ?-position carbon, which comprises introducing a step of treating in contact with water with heating under acidic to neutral conditions into the process. Also, the present invention provides a process of starting from N-alkoxycarbonyl-ethylamine compounds having a leaving group at the ?-position to prepare ?-hydroxyethylamine compounds having an inverted steric configuration at the ?-position carbon, which comprises subjecting the oxazolidinone derivatives prepared as described above to a step of treating in contact with water under basic conditions.
    Type: Grant
    Filed: May 23, 2002
    Date of Patent: December 11, 2007
    Assignee: Kaneka Corporation
    Inventors: Hiroshi Murao, Koki Yamashita, Toshihiro Takeda, Yasuyoshi Ueda
  • Patent number: 7220883
    Abstract: Process for the preparation of primary amines of formula (I): where R3 represents an alkyl, cycloalkyl or aralkyl group, by reaction of a triazolium salt of formula (II): where R1 and R2 represent hydrogen or an alkyl, aralkyl or aryl group, R4 represents an alkyl or aralkyl group or a residue of an organic polymer functionalized by an alkylating group, and A? represents a halogen, alkylsulphonate, arylsulphonate, alkyl sulphate, hydrogensulphate, hemisulphate, perchlorate or hydroxide, with a hydride, in order to obtain an amine of formula (I), which is isolated, if desired, and intermediates.
    Type: Grant
    Filed: July 28, 2003
    Date of Patent: May 22, 2007
    Assignee: Clariant (France)
    Inventors: Muriel Serradeil Albalat, Jean-Claude Vallejos, Christian Roussel, Didier Wilhelm
  • Patent number: 7189879
    Abstract: A new process for the production of 1-hydroxymethyl-1,3,5-triazapentane, trihydrochloride is described.
    Type: Grant
    Filed: May 24, 2005
    Date of Patent: March 13, 2007
    Assignee: Schering AG
    Inventors: Johannes Platzek, Jan Huebner, Orlin Petrov
  • Patent number: 7026515
    Abstract: A readily available and inexpensive natural ?-amino acid is converted into a compound represented by formula (1), which is then reacted with an organometallic reagent represented by formula (2) to give an optically active 5-hydroxyoxazolidine represented by formula (3), which is then treated with an acid to provide an optically active aminoketone represented by formula (4). The product is then converted into an optically active aminoalcohol represented by formula (5) or (6) by, for example reduction.
    Type: Grant
    Filed: November 9, 2001
    Date of Patent: April 11, 2006
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Hidetoshi Tsunoda, Kunio Okumura, Kengo Otsuka
  • Patent number: 6924315
    Abstract: The present invention provides compounds useful as surfactants having formula (1), including isomers thereof: wherein a and b are integers independently selected from about 3 to about 6; x is an integer from about 1 to about 12; (m+n) is from about 1 to about 4; the R1 groups are independently selected from the group consisting of linear, cyclic, and branched alkyl, alkenyl, aryl, and alkylaryl groups having from about C3 to about C30 atoms; and when (m+n) is equal to or greater than 2, each R1 may be independently R2 or R3, wherein R2 and R3 are independently selected from the group consisting of linear, cyclic, and branched alkyl, alkenyl, aryl, and alkylaryl groups having from about C3 to about C30 atoms. The invention also provides a method for reducing surface tension in a waterborne composition or an industrial process by the incorporation of a surfactant having formula (1) and an aqueous composition comprising a surfactant having formula (1).
    Type: Grant
    Filed: March 13, 2003
    Date of Patent: August 2, 2005
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Christine Peck Kretz, Michael Edward Ford, Kevin Rodney Lassila
  • Patent number: 6906224
    Abstract: A process for producing ?-aminohalomethyl ketones or N-protected ?-aminohalomethyl ketones from specified 3-oxazolidin-5-one derivatives via 5-halomethyl-5-hydroxy-3-oxazolidine derivatives. By this process, ?-aminohalomethyl ketones and compounds relating to them can be obtained efficiently and economically in industrial scale.
    Type: Grant
    Filed: October 30, 2003
    Date of Patent: June 14, 2005
    Assignee: Ajinomoto Co., Inc.
    Inventors: Tomoyuki Onishi, Naoko Hirose, Takayuki Suzuki, Takashi Nakano, Masakazu Nakazawa, Kunisuke Izawa
  • Publication number: 20040210089
    Abstract: A process for producing &agr;-aminohalomethyl ketones or N-protected &agr;-aminohalomethyl ketones from specified 3-oxazolidin-5-one derivatives via 5-halomethyl-5-hydroxy-3-oxazolidine derivatives. By this process, &agr;-aminohalomethyl ketones and compounds relating to them can be obtained efficiently and economically in industrial scale.
    Type: Application
    Filed: October 30, 2003
    Publication date: October 21, 2004
    Applicant: Ajinomoto Co., Inc.
    Inventors: Tomoyuki Onishi, Naoko Hirose, Takayuki Suzuki, Takashi Nakano, Masakazu Nakazawa, Kunisuke Izawa
  • Patent number: 6800764
    Abstract: 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: Grant
    Filed: November 26, 2002
    Date of Patent: October 5, 2004
    Assignee: Wyeth
    Inventors: Anthony Frank Kreft, Madelene Miyoko Antane, Derek Cecil Cole, Dennis Martin Kubrak, Lynn Resnick, Joseph Raymond Stock, Zheng Wang
  • Patent number: 6790996
    Abstract: The invention relates to a process for preparing primary amines by hydrogenating nitrites in the presence of a catalyst comprising cobalt and optionally, in addition, nickel and also at least one further doping metal on a particulate support material, the cobalt and, if present, the nickel having an average particle size of from 3 to 30 nm in the active catalyst. The invention further relates to the use of the catalyst in a process for preparing primary amines by hydrogenating nitrites.
    Type: Grant
    Filed: October 17, 2002
    Date of Patent: September 14, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Andreas Ansmann, Christoph Benisch
  • Patent number: 6646150
    Abstract: The present invention provides a process for industrially producing (aminomethyl)trifluoromethylcarbinol derivatives, in particularly, optically active compounds thereof, which are useful as starting compounds for drugs such as protease inhibitors, etc.
    Type: Grant
    Filed: June 13, 2002
    Date of Patent: November 11, 2003
    Assignee: Dainippon Pharmaceutical Co., Ltd.
    Inventors: Fuminori Sato, Tomoki Omodani, Ryotaro Shiratake, Yasunao Inoue, Takashi Deguchi
  • Patent number: 6613944
    Abstract: The present invention includes a number of novel intermediates such as the (S)-secondary alcohol of formula (VIIIA) X2—CH2—C*H(OH)—CH2—NH—CO—RN  (VIIIA) and processes for production of pharmacologically useful oxazolidinones.
    Type: Grant
    Filed: January 28, 2003
    Date of Patent: September 2, 2003
    Assignee: Pharmacia & Upjohn Company
    Inventor: Bruce Allen Pearlman
  • Patent number: 6528687
    Abstract: 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: Grant
    Filed: July 23, 2001
    Date of Patent: March 4, 2003
    Assignee: Chirotech Technology Limited
    Inventors: Christopher James Cobley, Julian Paul Henschke, James Andrew Ramsden
  • Patent number: 6521564
    Abstract: A process for the modification of a hydrogenation catalyst of the Raney nickel, Raney cobalt, nickel-on-carrier or cobalt-on-carrier type, which process includes treating the hydrogenation catalyst at temperatures of about 0° C. to about 120° C. with carbon monoxide, carbon dioxide, formaldehyde, a lower aliphatic aldehyde, an aromatic aldehyde, an aliphatic ketone, an aromatic ketone, a mixed aliphatic/aromatic ketone, glyoxal, pyruvaldehyde or glyoxylic acid as the modification agent in a liquid dispersion medium consisting of water or an organic solvent for a duration of about 15 minutes to about 24 hours. When the thus-modified catalyst is used in the hydrogenation of a nitrile to the corresponding amine, the selectivity is increased, and significantly favors the amount of the primary amine vis-à-vis the undesired secondary amine in the hydrogenation product as compared to when the corresponding unmodified catalyst is employed.
    Type: Grant
    Filed: November 30, 2000
    Date of Patent: February 18, 2003
    Assignee: Roche Vitamins, Inc.
    Inventors: Oliver Gerald Degischer, Felix Roessler
  • Patent number: 6350714
    Abstract: The present invention relates to a process for preparing a catalyst by activating a catalytic composition which comprises a) at least one metal of group IB or IIB or a compound thereof, b) where appropriate a carrier which comprises treating the composition with an alkyne of the general formula I R1—C≡C—R2  (I) in which R1 is alkyl, cycloalkyl, aryl, hydroxyalkyl, haloalkyl, alkoxy or alkoxyalkyl, R2 is a hydrogen atom, alkyl, cycloalkyl or aryl, and a carbonyl compound of the general formula II in which R3 and R4 are, independently of one another, a hydrogen atom, alkyl, haloalkyl, cycloalkyl or aryl, to catalysts obtainable by this process, and to alkynylations and aminoalkylations employing these catalysts.
    Type: Grant
    Filed: May 31, 2000
    Date of Patent: February 26, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Arnd Böttcher, Jochem Henkelmann, Thomas Preiss, Melanie Brunner
  • Patent number: 6312538
    Abstract: A new compound, 1,1-diamino-2,2-dinitroethylene suitable for use as an explosive, as well as an intermediate for preparing the compound consisting of a heterocyclic 5- or 6-ring of the general formula wherein n=at least 1. The compound is prepared by nitrating a heterocyclic 5- or 6-ring containing the structural element wherein Y is an alkoxy group, with a nitrating acid at a low temperature, preferably 0-30° C., and selecting the acidity of the nitrating acid for obtaining a substantial yield of a product containing the structural element and hydrolyzing said product in an aqueous medium for separating 1,1-diamino-2,2--dinitroethylene which is recovered as a precipitate.
    Type: Grant
    Filed: January 18, 2000
    Date of Patent: November 6, 2001
    Assignee: Totalforsvarets Forskningsinstitut
    Inventors: Nikolai Latypov, Abraham Langlet, Ulf Wellmar
  • Patent number: 6307067
    Abstract: Nucleophilic oxygen species, such as primary alcohols, carboxylates, and water, are added to vinyl epoxides in a highly regioselective and enantioselective manner, providing a convenient route to enantiomerically enriched 1,2-diols and oxygen-containing heterocycles. The reaction employs a chiral Pd(0) complex and a borane or borate as co-catalysts Also described are similar additions of nitrogen nucleophiles, and the addition of carbonates to vinyl epoxides using a chiral Pd(0) catalyst.
    Type: Grant
    Filed: September 7, 1999
    Date of Patent: October 23, 2001
    Assignee: The Board of Trustees of the Leland Stanford Junior University
    Inventors: Ernest John McEachern, Francisco Dean Toste, Barry Martin Trost
  • Patent number: 6075168
    Abstract: This invention concerns a process for the production of diethanolamine (DEA) by contacting monoethanolamine (MEA) and ethylene oxide (EO) in a reactive distillation column. The process may achieve high selectivity to DEA.
    Type: Grant
    Filed: August 21, 1998
    Date of Patent: June 13, 2000
    Assignee: Huntsman Petrochemical Corporation
    Inventors: Ralph M. DiGuilio, Michael W. McKinney
  • Patent number: 6040464
    Abstract: A process for producing protected 3-amino-1,2-dihydroxypropane acetal, particularly in chiral forms, for use as an intermediate in the preparation of various 3-carbon compounds which are chiral. In particular, the present invention relates to the process for preparation of 3-amino-1,2-dihydroxypropane isopropylidene acetal. The protected 3-amino-1,2-dihydroxypropane acetal is a key intermediate to the preparation of chiral 3-carbon compounds which in turn are intermediates to various pharmaceuticals.
    Type: Grant
    Filed: May 27, 1999
    Date of Patent: March 21, 2000
    Assignee: Board of Trustees operating Michigan State University
    Inventors: Rawle I. Hollingsworth, Guijun Wang
  • Patent number: 6028225
    Abstract: Hydroxy-substituted hydroxylamine antioxidants can be prepared by reacting hydroxylamine or a mono-substituted hydroxylamine, in free base form, with an epoxide. The antioxidant reaction product can be used without isolation from the reaction solution, and combined with a color developing agent to provide a photographic color developing composition in either concentrated or working strength formulations. The method for preparing the antioxidant is rapid and efficient because of the use of the free base form of the hydroxylamine reactant, higher temperatures (at or above 50.degree. C.) and certain molar ratios of reactants.
    Type: Grant
    Filed: September 15, 1998
    Date of Patent: February 22, 2000
    Assignee: Eastman Kodak Company
    Inventor: Lynda W. McGarry
  • Patent number: 5922916
    Abstract: The present invention relates to a process for preparing 5-methylene cyclic carbamates either by cyclization of an alkynyl amine with carbon dioxide in the presence of a copper catalyst or by forming an isocyanate from a substituted acetoacetamide followed by hydrolysis. The 5-methylene cyclic carbamates by either method are converted to 5-(chloromethylene) cyclic carbamates, using trichloroisocyanuric acid, followed by hydrolysis to a chloroketoamine.The chloroketoamine from the process of this invention additionally can be reacted with an organic acid chloride to form an amide compound which is useful as a fungicide.
    Type: Grant
    Filed: April 13, 1998
    Date of Patent: July 13, 1999
    Assignee: Rohm and Haas Company
    Inventors: Heather Lynnette Rayle, Renee Caroline Roemmele, Randall Wayne Stephens, Joshua Anthony Chong, Fereydon Abdesaken, Charles Chao Wu
  • Patent number: 5906998
    Abstract: In the decomposition of a polymer containing a urethane linkage and/or urea linkage in the presence of a decomposing agent, the amount of evolved carbon dioxide is measured and the decomposition reaction is conducted until a total amount of evolved carbon dioxide reaches a specified value to obtain a liquid decomposition product. According to the present invention, a decomposition product having constant quality can be obtained in a simple manner.
    Type: Grant
    Filed: August 20, 1996
    Date of Patent: May 25, 1999
    Assignees: Sumitomo Bayer Urethane Co., Inc., Toyota Jidosha Kabushiki Kaisha
    Inventors: Yuji Hoshino, Takaaki Masuda, Hiroshi Ikuta, Hisao Mitobe
  • Patent number: 5831129
    Abstract: N-Hydroxyalkyl-substituted aminoalkynes of the formula I ##STR1## are prepared by reacting an alkyne with a 1-oxa-3-azaheterocyclo-alkane in a reaction with heterogeneous catalysis by a catalyst which comprises a compound of a metal of the first or second sub-group.
    Type: Grant
    Filed: October 7, 1997
    Date of Patent: November 3, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Thomas Preiss, Jochem Henkelmann, Joachim Wulff-Doring, Susanne Stutz, Thomas Ruhl
  • Patent number: 5824821
    Abstract: The invention provides a process for the production of a 2,3-dihydroxypropylamino compound, said process comprising the reaction steps of:(i) obtaining an allylamino compound;(ii) epoxidizing said allylamino compound to yield an epoxypropylamino compound; and(iii) hydrolysing said epoxypropylamino compound to yield a 2,3-dihydroxypropylamino compound.This process may be used to produce simple 2,3-dihydroxypropylamino compounds such as APD or complex ones such as BAPD (an intermediate in the production of iohexol).
    Type: Grant
    Filed: February 7, 1997
    Date of Patent: October 20, 1998
    Assignee: Nycomed Imaging AS
    Inventors: David Redick Lane, Janis Vasilevskis
  • Patent number: 5801202
    Abstract: 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: Grant
    Filed: May 30, 1997
    Date of Patent: September 1, 1998
    Assignee: Kao Coproration
    Inventors: Taketoshi Fujimori, Hiroshi Kusuoku, Akira Yamamuro, Yukihiro Yada, Kazuhiko Higuchi, Genji Imokawa, Naoki Kondo, Yoshinori Masukawa, Hajime Tokuda, Hisashi Tsujimura
  • Patent number: 5777165
    Abstract: N-alkyl polyhydroxy alkyl amines such as N-methyl glucamine having a Gardner Color of less than 1 are reacted with sources of fatty acyl groups such as methyl esters, anhydrides, and/or fatty acids that have greater than 98% transmittance at 460 nm in organic hydroxy solvents such as methanol to prepare N-alkyl polyhydroxy amine amides with good color. The N-alkyl polyhydroxyamines can be purified by crystallization, and/or subjected to reductive bleaching, to provide superior color. The reaction is preferably carried out at low temperature for short periods of time and with low catalyst levels to minimize formation of cyclic products. The resulting amide product can be further purified by treatment with anionic and cationic exchange resins to remove soap and amine impurities. The anionic ion exchange resin can be readily regenerated by acidifying it followed by washing with an organic solvent.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: July 7, 1998
    Assignee: The Procter & Gamble Company
    Inventors: Junan Kao, Ephraim Lamar Kelly, Vicki Lynn Weber, Michael Steven Gibson, Donald Benjamin Appleby, Joseph Fredrich Sherman, Ronald Edward Pegoli, Mary Celine Schneider, Terry Franklin Formyduval, Larry Nelson Hawkins
  • Patent number: 5770773
    Abstract: A process for the preparation of 5-amino-1,3-dioxanes of formula (I), comprising the catalytic hydrogenation of the new oximes of formula (II) is described.
    Type: Grant
    Filed: March 28, 1997
    Date of Patent: June 23, 1998
    Assignee: Zambon Group S.p.A.
    Inventors: Antonio Nardi, Marco Villa
  • Patent number: 5723673
    Abstract: N-alkyl polyhydroxy alkyl amines such as N-methyl glucamine having a Gardner Color of less than 1 are reacted with sources of fatty acyl groups such as methyl esters, anhydrides, and/or fatty acids that have greater than 98% transmittance at 460 nm in organic hydroxy solvents such as methanol to prepare N-alkyl polyhydroxy amine amides with good color. The N-alkyl polyhydroxyamines can be purified by crystallization, and/or subjected to reductive bleaching, to provide superior color. The reaction is preferably carried out at low temperature for short periods of time and with low catalyst levels to minimize formation of cyclic products. The resulting amide product can be further purified by treatment with anionic and cationic exchange resins to remove soap and amine impurities. The anionic ion exchange resin can be readily regenerated by acidifying it followed by washing with an organic solvent.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: March 3, 1998
    Assignee: The Procter & Gamble Company
    Inventors: Junan Kao, Ephraim Lamar Kelly, Vicki Lynn Weber, Michael Steven Gibson, Donald Benjamin Appleby, Joseph Fredrich Sherman, Ronald Edward Pegoli, Mary Celine Schneider, Terry Franklin Formyduval, Larry Nelson Hawkins
  • Patent number: 5693865
    Abstract: Fluorinated alkene compounds useful for and methods of controlling nematodes, insects, and acarids that prey on agricultural crops. Polar compounds, for example, 3,4,4-trifluoro-3-butene-1-amine or 3,4,4-trifluoro-3-butenoic acid, are particularly useful for systemic control of pests. Novel method and intermediates for the preparation of 3,4,4-trifluoro-3-butene-1-amine are also provided.
    Type: Grant
    Filed: December 11, 1996
    Date of Patent: December 2, 1997
    Assignee: Monsanto Company
    Inventor: Peter Gerrard Ruminski
  • Patent number: 5679862
    Abstract: A process for the amination of aliphatic alkane derivatives such as alcohols (mono and polyhydric) which uses catalytic distillation to take advantage of the condensing distillate within the distillation reaction zone in the distillation column reactor. The operation of the distillation column reactor results in both a liquid and vapor phase within the distillation reaction zone. The catalyst is prepared in the form of a distillation structure. The reaction is carried out in a distillation column reactor at a low hydrogen partial pressure, e.g. in the range of 0.1 psia to less than 10 psia.
    Type: Grant
    Filed: March 25, 1996
    Date of Patent: October 21, 1997
    Assignee: Chemical Research & Licensing Company
    Inventors: Speros Peter Nemphos, Dennis Hearn
  • Patent number: 5663372
    Abstract: Described herein is a process for the preparation of 5-amino-1,3-dioxanes of formula (I), wherein R and R.sub.1 have the meanings reported in the description, comprising the catalytic hydrogenation of the new oximes of formula (II).
    Type: Grant
    Filed: October 10, 1996
    Date of Patent: September 2, 1997
    Assignee: Zambon Group S.p.A.
    Inventors: Antonio Nardi, Marco Villa
  • Patent number: 5625098
    Abstract: Amines such as methyl amine are reacted with materials such as reducing sugars in aqueous/hydroxy solvents such as water and/or methanol to prepare N-alkyl polyhydroxy amines. Accordingly, glucose is reacted with methyl amine and the resulting adduct is hydrogenated to yield N-methylglucamine. The N-alkyl polyhydroxyamines can be subsequently reacted with fatty esters to provide polyhydroxy fatty acid amides useful as detersive surfactants. Thus, detersive surfactants are available from non-petrochemical precursors such as sugars and sugar sources such as corn syrup, and fatty acid esters derivable from various fats and oils.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: April 29, 1997
    Assignee: The Procter & Gamble Company
    Inventors: Junan Kao, Jeffrey J. Scheibel, Robert E. Shumate, Cynthia M. Stark, Roland G. Severson, Jr., Kevin L. Garber, Scott A. VanDiest
  • Patent number: 5610227
    Abstract: The present invention provides anionic polymerization initiators, comprising lithium amino magnesiate complexes, resulting in diene polymer and copolymer elastomers. The invention initiators have stable living ends at high polymerization temperatures and produce polymers containing a high level of tertiary amine functionality. Such polymers exhibit an increased efficiency in coupling termination reactions, and elastomers and products prepared from such polymers exhibit reduced hysteresis properties. Methods are also provided for preparing the initiators, the polymers and the elastomers.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: March 11, 1997
    Assignee: Bridgestone/Firestone, Inc.
    Inventors: Thomas A. Antkowiak, James E. Hall
  • Patent number: 5600001
    Abstract: Azines of formula (I): ##STR1## in which R and R' either are identical and represent an alkyl radical containing 1 to 4 carbon atoms or an alkenyl radical containing 3 to 5 carbon atoms, or together form a radical of formula (II):--CHR.sub.1 --(CR.sub.2 R.sub.3).sub.n --CHR.sub.4 -- (II)in which R.sub.1, R.sub.2, R.sub.3 and R.sub.4, identical or different, represent a hydrogen atom or an alkyl radical containing 1 to 4 carbon atoms and n represents 0 or 1, in their different stereoisomer forms, their preparation process and their use.
    Type: Grant
    Filed: February 22, 1996
    Date of Patent: February 4, 1997
    Assignee: Societe Francaise Hoechst
    Inventors: Alain Schouteeten, Yani Christidis
  • Patent number: 5541321
    Abstract: A process is disclosed for the preparation of a substituted diaminoalcohol of the formula: ##STR1##
    Type: Grant
    Filed: March 30, 1995
    Date of Patent: July 30, 1996
    Assignee: Abbott Laboratories
    Inventors: William R. Baker, John K. Pratt, Daniel W. Norbeck, Chen Zhao
  • Patent number: 5541320
    Abstract: A process is disclosed for the preparation of a substituted diaminoalcohol of the formula: ##STR1##
    Type: Grant
    Filed: March 30, 1995
    Date of Patent: July 30, 1996
    Assignee: Abbot Laboratories
    Inventors: William R. Baker, John K. Pratt, Daniel W. Norbeck, Chen Zhao
  • Patent number: 5488166
    Abstract: Provided by the present invention is a process for the biocatalytic synthesis of optically pure sphingosines from achiral starting material. The stereoisomers of sphingosine are prepared from chiral arene diols using stereospecific reaction techniques to obtain the desired sphingosine or derivative thereof.
    Type: Grant
    Filed: January 23, 1995
    Date of Patent: January 30, 1996
    Assignee: Virginia Tech Intellectual Properties, Inc.
    Inventor: Tomas Hudlicky
  • Patent number: 5468841
    Abstract: The present invention provides an improved method of carrying out cationic polymerization of cyclic ether monomers substituted with high-energy, electron-withdrawing pendant groups (e.g., BAMO and NMMO). Such cyclic ether monomers are polymerized with an initiator precursor (i.e., an alcohol) and boron trifluoride tetrahydrofuranate (BF.sub.3 .cndot.THF). It has been discovered that when boron trifluoride tetrahydrofuranate is used as a catalyst in the cationic polymerization of cyclic ether monomers substituted with high-energy, electron-withdrawing pendant groups (e.g., BAMO and NMMO), polymers are produced that have improved functionality and low poly-dispersity. The polymers formed using the method of the present invention are useful for forming cross-linked elastomers which, in turn, are useful for forming elastomeric binders for high-energy compositions, such as propellants, explosives, gasifiers or the like.
    Type: Grant
    Filed: April 13, 1994
    Date of Patent: November 21, 1995
    Assignee: Aerojet General Corporation
    Inventors: Aslam A. Malik, Thomas G. Archibald, Roland P. Carlson, Gerald E. Manser
  • Patent number: 5436339
    Abstract: A process is disclosed for the preparation of a substituted diaminoalcohol of the formula: ##STR1##
    Type: Grant
    Filed: July 14, 1992
    Date of Patent: July 25, 1995
    Assignee: Abbott Laboratories
    Inventors: William R. Baker, John K. Pratt, Daniel W. Norbeck, Chen Zhao
  • Patent number: 5426228
    Abstract: Described herein is a novel method of preparing selectively diastereomers of sphingosine bases and their analogues of general formula (1a) or (1b) ##STR1## where R is an aliphatic or aromatic substituent containing a straight, branched or cyclic chain, which may include one or several heteroatoms as chain members and one or several functional groups as substituents. The method comprises the steps of:a) converting a starting material into an intermediate product in the form of .alpha.,.beta.-unsaturated ketone having the general formula (4a) or (4b) ##STR2## where R is as defined above and PG are any protecting groups compatible with the method,b) reducing said .alpha.,.beta.-unsaturated ketone to an aminoalcohol with DIBAL in toluene to obtain selectively an anti-diastereomer, andc) removing the protecting groups to obtain the free sphingosine base or its analogue according to formula (1a) or (1b).
    Type: Grant
    Filed: June 27, 1994
    Date of Patent: June 20, 1995
    Inventors: Ari Koskinen, Paivi Koskinen
  • Patent number: 5410081
    Abstract: Compounds of the formula (I) ##STR1## are prepared by reacting 2-mercaptoethanol with compounds of the general formula (II) ##STR2## the substituents having the definition given in the description.
    Type: Grant
    Filed: June 24, 1994
    Date of Patent: April 25, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Klaus Kunde, Karl-Josef Herd
  • Patent number: 5368760
    Abstract: Cystamine is produced by a method which comprises reacting a 2,2-dialkyl thiazolidine represented by the general formula (1): ##STR1## wherein R.sup.1 and R.sup.2 independently are alkyl groups of 1 to 5 carbon atoms, with a peroxide in the presence of water. An alkylene oxide adduct of cystamine is produced by a method which comprises reacting the reaction mixture obtained as described above further with an alkylene oxide. These cystamine and alkylene oxide adduct of cystamine are useful as an additive for an aqueous lubricant.
    Type: Grant
    Filed: June 25, 1993
    Date of Patent: November 29, 1994
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Jun Okamoto, Yujiro Goto, Masao Kitano, Seiichi Suzuki
  • Patent number: 5347003
    Abstract: Methods are provided whereby an N-C-N compound is regenerated from a product of a sulfur scavenging reaction, in which said N-C-N compound removes a sulfur atom from a sulfur compound, to form the original N-C-N compound. The N-C-N compound is represented by the formula (I): ##STR1## The product includes a hetero compound having sulfur, carbon and nitrogen atoms in its backbone. In one embodiment, the product is mixed with (1) a nitrogen compound represented by the formula (II): ##STR2## and (2) an alkaline compound selected from alkali metal, alkaline earth metal and transition metal compounds, to form a solution, slurry or dispersion. The hetero compound is reacted with the nitrogen compound in the presence of the alkaline compound, such that a sulfur atom of the hetero compound is replaced by a nitrogen atom of the nitrogen compound. If necessary, the pH of the solution may be adjusted to about 8 to about 13 to facilitate the reaction. In alternative embodiments, the product also includes an amine complex.
    Type: Grant
    Filed: March 5, 1993
    Date of Patent: September 13, 1994
    Assignee: Quaker Chemical Corporation
    Inventors: Edward A. Trauffer, Robert D. Evans
  • Patent number: 5344990
    Abstract: 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: Grant
    Filed: October 5, 1993
    Date of Patent: September 6, 1994
    Assignee: Abbott Laboratories
    Inventors: William R. Baker, Stephen L. Condon
  • Patent number: 5334764
    Abstract: Amines such as methyl amine are reacted with materials such as reducing sugars in hydroxy solvents such as methanol to prepare N-alkyl polyhydroxy amines. Accordingly, glucose is reacted with methyl amine and the resulting adduct is hydrogenated to yield N-methylglucamine. The N-alkyl polyhydroxyamines can be subsequently reacted with fatty esters to provide polyhydroxy fatty acid amides useful as detersive surfactants. Thus, detersive surfactants are available from non-petrochemical precursors such as sugars and sugar sources such as corn syrup, and fatty acid esters derivable from various fats and oils.
    Type: Grant
    Filed: May 6, 1993
    Date of Patent: August 2, 1994
    Assignee: The Procter & Gamble Company
    Inventors: Jeffrey J. Scheibel, Daniel S. Connor, Robert E. Shumate, James B. St. Laurent
  • Patent number: 5326873
    Abstract: A method of forming 4-amino-2-buten-1-ol using 3,4-epoxy-1-butene is disclosed. A nitrogen nucleophile (e.g., an amine) is reacted with 3,4-epoxy-1-butene in the presence of a polymer-bound complex of palladium having up to four phosphine ligands.
    Type: Grant
    Filed: June 5, 1992
    Date of Patent: July 5, 1994
    Assignee: Eastman Kodak Company
    Inventors: Stephen A. Godleski, Yann Hung
  • Patent number: 5274054
    Abstract: Adducts which are obtainable by reacting cycloaliphatic or heterocycloaliphatic polyamines containing at least two primary groups with polyfunctional epoxides containing more than two epoxy groups per molecule in such amounts as to supply 10-100 equivalents of active hydrogen atoms bound to amino nitrogen per one epoxide equivalent, are suitable hardeners for epoxy adhesives, especially adhesives for metals and thermosetting plastics.
    Type: Grant
    Filed: April 1, 1992
    Date of Patent: December 28, 1993
    Assignee: Ciba-Geigy Corporation
    Inventors: Roland Moser, Hans Lehmann, Daniel Bar
  • Patent number: 5262570
    Abstract: A method of producing ethylenediamines represented by the general formula ##STR1## wherein R represents a hydrogen atom, or a methyl or ethyl group, which comprises reacting an aziridine compound of the general formula ##STR2## wherein R is as defined, with ammonia in the gaseous phase in the presence of a solid acid catalyst. In another aspect, a method of producing ethylenediamines of the general formula (I), which comprises reacting a reaction product containing an aziridine compound of the general formula (II), obtained by the gaseous phase intramolecular dehydration reaction of an alkanolamine represented by the general formula ##STR3## wherein X represents the OH group or the NH.sub.2 group, Y represents the NH.sub.2 group when X is the OH group and the OH group when X is the NH.sub.2 group, and R is as defined,in the presence of a catalyst A, with ammonia in the gaseous phase in the presence of a solid acid catalyst (catalyst B).
    Type: Grant
    Filed: January 11, 1993
    Date of Patent: November 16, 1993
    Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd.
    Inventors: Yuuji Shimasaki, Hideaki Tsuneki, Youichi Hino, Tetsuro Hayashi, Michio Ueshima
  • Patent number: 5235107
    Abstract: A method of producing ethylenediamines represented by the general formula ##STR1## wherein R represents a hydrogen atom, or a methyl or ethyl group, which comprises reacting an aziridine compound of the general formula ##STR2## wherein R is as defined, with ammonia in the gaseous phase in the presence of a solid acid catalyst. In another aspect, a method of producing ethylenediamines f the general formula (I), which comprises reacting a reaction product containing an aziridine compound of the general formula (II), obtained by the gaseous phase intramolecular dehydration reaction of an alkanolamine represented by the general formula ##STR3## wherein X represents the OH group or the NH.sub.2 group, Y represents the NH.sub.2 group when X is the OH group and the OH group when X is the NH.sub.2 group, and R is as defined, in the presence of a catalyst A, with ammonia in the gaseous phase in the presence of a solid acid catalyst (catalyst B).
    Type: Grant
    Filed: April 10, 1991
    Date of Patent: August 10, 1993
    Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd.
    Inventors: Yuuji Shimasaki, Hideaki Tsuneki, Youichi Hino, Tetsuro Hayashi, Michio Ueshima