Of Carbonyl Containing Compound Patents (Class 564/396)
  • Patent number: 8809591
    Abstract: The present invention is directed to a process for the manufacture of 2,3,5-trimethyl-hydro-p-benzoquinone comprising the following steps: a) hydrogenating 2,6-dimethyl-p-benzoquinone with hydrogen in the presence of a hydrogenation catalyst in an organic solvent to obtain 2,6-dimethyl-hydro-p-benzoquinone; b) reacting 2,6-dimethyl-hydro-p-benzoquinone with a secondary amine and formal-dehyde in an organic solvent to obtain 2,6-dimethyl-3-(N,N-disubstituted aminomethyl)-hydro-p-benzoquinone; c) reacting 2,6-dimethyl-3-(N,N-disubstituted aminomethyl)-hydro-p-benzoquinone with hydrogen in the presence of a hydrogenolysis catalyst in an organic solvent to obtain 2,3,5-trimethylhydro-p-benzoquinone; wherein the organic solvent in all steps a), b) and c) is independently selected from the group consisting of methyl tert.-butyl ether, ethyl tert.-butyl ether, methyl tert.-amyl ether, methoxycyclopentane and any mixtures thereof. Preferably the organic solvent used in all steps a), b) and c) is the same.
    Type: Grant
    Filed: August 25, 2011
    Date of Patent: August 19, 2014
    Assignee: DSM IP Assets B.V.
    Inventors: Werner Bonrath, Thomas Netscher, Jan Schütz, Bettina Wüstenberg
  • Patent number: 8592631
    Abstract: A process for synthesizing 2-methoxymethyl-1,4-benzenediamine, its derivatives of formula (IV) and the salts thereof, which comprises a reductive amination step. The preferred final product is 2-methoxymethyl-1,4-benzenediamine of formula (IV-a). These compounds may be used as primary intermediates in compositions for dyeing keratin fibers.
    Type: Grant
    Filed: January 28, 2011
    Date of Patent: November 26, 2013
    Assignee: The Procter & Gamble Company
    Inventors: John Michael Gardlik, Garry Steven Garrett, Bryan Patrick Murphy, John Michael Janusz, John August Wos
  • Publication number: 20130211080
    Abstract: The present invention is directed to a process for the manufacture of 2,3,5-trimethyl-hydro-p-benzoquinone comprising the following steps: a) hydrogenating 2,6-dimethyl-p-benzoquinone with hydrogen in the presence of a hydrogenation catalyst in an organic solvent to obtain 2,6-dimethyl-hydro-p-benzoquinone; b) reacting 2,6-dimethyl-hydro-p-benzoquinone with a secondary amine and formal-dehyde in an organic solvent to obtain 2,6-dimethyl-3-(N,N-disubstituted aminomethyl)-hydro-p-benzoquinone; c) reacting 2,6-dimethyl-3-(N,N-disubstituted aminomethyl)-hydro-p-benzoquinone with hydrogen in the presence of a hydrogenolysis catalyst in an organic solvent to obtain 2,3,5-trimethylhydro-p-benzoquinone; wherein the organic solvent in all steps a), b) and c) is independently selected from the group consisting of methyl tert.-butyl ether, ethyl tert.-butyl ether, tert.-amyl ether, methoxycyclopentane and any mixtures thereof. Preferably the organic solvent used in all steps a), b) and c) is the same.
    Type: Application
    Filed: August 25, 2011
    Publication date: August 15, 2013
    Applicant: DSM IP ASSETS B.V.
    Inventors: Werner Bonrath, Thomas Netscher, Jan Schütz, Bettina Wüstenberg
  • Publication number: 20130030073
    Abstract: Amine-initiated polyether polyols are made by reacting an amine adduct with a triglyceride in the presence of an alkylene oxide to obtain a polyol having a total renewables content of at least 20%.
    Type: Application
    Filed: July 26, 2011
    Publication date: January 31, 2013
    Applicant: Bayer MaterialScience LLC
    Inventors: Don S. Wardius, Steven L. Schilling
  • Patent number: 7737302
    Abstract: This invention described a synthesis method of bupropion hydrochloride. m-chloropropiophenone was brominated directly with bromine, then aminated with t-butylamine and finally reacted with HCl to obtain crude product of bupropion hydrochloride. Pure product was obtained after recrystallization. This method is convenient and suitable for commercial manufacturing because of low cost of production, high yield, less byproducts and being environmental friendly.
    Type: Grant
    Filed: July 7, 2008
    Date of Patent: June 15, 2010
    Assignee: Zhejiang Apeloa Medical Technology Co., Ltd.
    Inventors: Chaogang Wu, Huayou Xiang, Xianghua Yu, Chun He, Fengying Li, Xianghong Shi, Chengyue Lu, Guoliang Chen, Yangxiang Ge
  • Patent number: 7709679
    Abstract: The invention provides a process for the simultaneous preparation of 4,4?-diphenylmethanediamine and also diphenylmethane diisocyanate and polyphenylenepolymethylene polyisocyanates, which comprises the steps a) preparation of a mixture of diphenylmethanediamine and polyphenylenepolymethylenepolyamines by acid condensation of aniline and formaldehyde and subsequent work-up of the mixture, b) splitting-off of part of the mixture prepared in step a), c) distillation of the mixture separated off in step b) in a column, d) recirculation of the bottom product from step c) to the end product from step a) and condensation of the overhead product from step c), e) distillation of the overhead product from step c) in a column, f) recirculation of the overhead product from step e) to the end product from step a), g) isolation of the 4,4?-diphenylmethanediamine obtained as bottom product in step e), h) reaction of the mixture from step a) with phosgene and subsequent work-up of the reaction product.
    Type: Grant
    Filed: January 12, 2007
    Date of Patent: May 4, 2010
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Bock, Hans-Juergen Pallasch, Filip Deberdt, Johnny Moors
  • Patent number: 7538251
    Abstract: Severely sterically hindered secondary aminoether alcohols are prepared by a process comprising reacting a ketene with sulfuric acid to produce an anhydride which is then reacted with, to cleave the ring of, a dioxane to yield a cleavage product which is then aminated using an amine, followed by hydrolysis with a base to yield the desired severely sterically hindered secondary aminoether alcohol.
    Type: Grant
    Filed: February 1, 2005
    Date of Patent: May 26, 2009
    Assignee: ExxonMobil Research and Engineering Company
    Inventors: Michael Siskin, Alan Roy Katritzky, Kostyantyn Mykolayevich Kirichenko, Adeana Richelle Bishop, Christine Nicole Elia
  • Patent number: 7524990
    Abstract: Severely sterically hindered secondary aminoether alcohols are prepared by reacting organic carboxylic, organic carboxylic acid halides, acid anhydrides or a ketene with an alkyl, alkaryl or alkylhalo sulfonate to yield a sulfonic-carboxylic anhydride compound which is then reacted with a dioxane to cleave the ring of the dioxane, yielding a cleavage product which cleavage product is then aminated with an alkylamine and hydrolyzed with base to yield the severely sterically hindered secondary aminoether alcohol.
    Type: Grant
    Filed: February 1, 2005
    Date of Patent: April 28, 2009
    Assignee: ExxonMobil Research and Engineering Company
    Inventors: Michael Siskin, Alan Roy Katritzky, Kostyantyn Mykolayevich Kirichenko, Adeana Richelle Bishop, Christine Nicole Elia
  • Publication number: 20080315155
    Abstract: This invention provides compositions which comprise at least one aromatic secondary diamine having a Gardner color number no more than about 6. The aromatic secondary diamine either is in the form of one benzene ring having two secondary amino groups on the ring, or is in the form of two benzene rings connected by an alkylene bridge and having one secondary amino group on each ring. At least one N,N?-dihydrocarbylhydroxylamine is optionally present in the composition. Processes for producing such compositions are also provided.
    Type: Application
    Filed: December 21, 2006
    Publication date: December 25, 2008
    Applicant: ALBEMARLE CORPORATION
    Inventors: John Y. Lee, David W. Owens, Richard D. Glass, Paul L. Wiggins
  • Patent number: 7361789
    Abstract: The present invention relates to novel dihydronaphthalene compounds, compositions, methods for using the same, and processes for preparing the same. The present invention also relates to novel total synthesis approaches for preparing these compounds. In addition, the present invention relates to methods of producing quantities of isomers of these compounds and separating and purifying them using chiral separation techniques. The present invention also relates to methods of producing quantities of a single isometric compound without the need for chiral separation techniques.
    Type: Grant
    Filed: July 27, 2005
    Date of Patent: April 22, 2008
    Assignee: Amgen Inc.
    Inventors: Qi Yan, Carlos Orihuela, Bo Shen, Ying Chen, Xin Wang, John Ng, Ruizhi Ji, Pengzu Zhou
  • Patent number: 7355077
    Abstract: A process for preparing tolterodine with high purity.
    Type: Grant
    Filed: October 26, 2005
    Date of Patent: April 8, 2008
    Assignees: Dr. Reddy's Laboratories Limited, Dr. Reddy's Laboratories, Inc.
    Inventors: Sundaram Venkataraman, Vijayavitthal Thippannachar Mathad, Kikkuru Srirami Reddy, Neti Srinivasan, Chinta Raveendra Reddy, Muthulingam Arunagiri, Routhu Lalitha Kumari
  • Patent number: 7186864
    Abstract: A compound of Formula (IA) or Formula (IB) wherein R1, R2, R3, R4, R5, R6, R7, and R8 are as defined herein, or a tautomer, prodrug, solvate, or salt thereof; pharmaceutical compositions containing such compounds, and methods of modulating the glucocorticoid receptor function and methods of treating disease-states or conditions mediated by the glucocorticoid receptor function or characterized by inflammatory, allergic, or proliferative processes in a patient using these compounds.
    Type: Grant
    Filed: May 28, 2003
    Date of Patent: March 6, 2007
    Assignee: Boehringer Ingelheim Pharmaceuticals, Inc.
    Inventors: Thomas Martin Kirrane, Jr., Daniel Kuzmich, John Robert Proudfoot, David Thomson
  • Patent number: 7164043
    Abstract: A conjugate addition reaction between an ?,?-unsaturated ketone compound and a carbamate compound is carried out to synthesize a ?-aminoketone, a salt or a hydrate salt of a transition metal of Groups 7 to 11 of the Periodic Table of Elements being present in the reaction system as the catalyst. The novel method and the catalyst are capable of synthesizing the ?-aminoketone by the Aza-Michael reaction with high yield and efficiency.
    Type: Grant
    Filed: March 7, 2003
    Date of Patent: January 16, 2007
    Assignee: Japan Science and Technology Agency
    Inventors: Shu Kobayashi, Masaharu Sugiura
  • Patent number: 6888029
    Abstract: The present invention relates to a process for the preparation of N-aryl amine and N-aryl amide compounds. Generally, the process of the present invention involves reacting a compound having a primary or secondary amino or amido group with an arylating compound, in the presence of a weak base and a transition metal catalyst, under reaction conditions effective to form an N-aryl amine or N-aryl amide compound, the transition metal catalyst comprising a Group 8 metal, e.g., Ni, Pd, or Pt, and at least one carbene-containing ligand. Typically, the transition metal catalyst is formed in a preceding step from the conjugate acid form of the carbene ligand, a stoichiometric amount of a strong base, and a Group 8 metal atom or ion.
    Type: Grant
    Filed: January 22, 2003
    Date of Patent: May 3, 2005
    Assignee: Massachusetts Institute of Technology
    Inventors: Stephen L. Buchwald, Joseph M. Fox
  • Patent number: 6642420
    Abstract: A process for the preparation of aldehydes and/or alcohols or amines by reacting olefins in the liquid phase with carbon monoxide and hydrogen, a part of these gases being dispersed in the form of gas bubbles in the reaction liquid and another part being dissolved in the reaction liquid, in the presence or absence of a primary or secondary amine and in the presence of a cobalt carbonyl, rhodium carbonyl, palladium carbonyl or ruthenium carbonyl complex dissolved homogeneously in the reaction liquid and having a phosphorus-, arsenic-, antimony- or nitrogen-containing ligand, at elevated temperatures and at 1 to 100 bar, wherein the reaction is carried out in a vertically arranged, tubular reactor comprising a reactor body and at least one circulation line, a part of the reaction liquid is fed continuously via the circulation line to at least one nozzle which is mounted in the upper part of the reactor body and is coordinated with a guide member, open at the top and bottom and bounded by parallel walls, in the
    Type: Grant
    Filed: February 7, 2001
    Date of Patent: November 4, 2003
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Zehner, Armin Ulonska, Rocco Paciello
  • Patent number: 6620776
    Abstract: A novel composition having the formula: wherein R1 is selected from the group consisting of an alkyl group containing from 1 to 20 carbon atoms and an aryl group, and R2 is selected from the group consisting of an alkyl group containing from 1 to 20 carbon atoms and an aryl group. The composition is made by combining an amine compound, a carbonyl compound, a solvent, and a sulfur-containing compound. The composition is used as a detergent additive in cleaning process.
    Type: Grant
    Filed: June 19, 2002
    Date of Patent: September 16, 2003
    Assignee: Phillips Petroleum Company
    Inventors: Mitchell D. Refvik, David W. Dockter
  • Patent number: 6506721
    Abstract: A novel composition having the formula: wherein R1 is selected from the group consisting of an alkyl group containing from 1 to 20 carbon atoms and an aryl group, and R2 is selected from the group consisting of an alkyl group containing from 1 to 20 carbon atoms and an aryl group. The composition is made by combining an amine compound, a carbonyl compound, a solvent, and a sulfur-containing compound. The composition is used as a detergent additive in cleaning process.
    Type: Grant
    Filed: September 22, 2000
    Date of Patent: January 14, 2003
    Assignee: Phillips Petroleum Company
    Inventors: Mitchell D. Refvik, David W. Dockter
  • Patent number: 6479697
    Abstract: A process for the preparation of &agr;-(2,4-disulfophenyl)-N-tert-butylnitrone diacids and pharmaceutically acceptable salts thereof by the reaction of the corresponding disulfophenyl aldehyde with N-tert-butylhydroxylammonium acetate is disclosed.
    Type: Grant
    Filed: April 5, 2001
    Date of Patent: November 12, 2002
    Assignee: AstraZeneca AB
    Inventors: Henry Kruk, John McGinley, Sergei Pouhov, John Vajda, Jörgen Blixt
  • Patent number: 6409773
    Abstract: Couplers for hair coloring compositions for oxidative dyeing of hair are compounds of the formula at least one coupler comprising a compound of the formula (1): wherein R is selected from of C1 to C2 alkyl and hydroxyethyl, R1 and R2 are each independently selected from the group consisting of C1 to C5 alkyl, C3 to C6 cycloalkyl, C1 to C5 alkoxy, C1 to C5 hydroxyalkyl, C1 to C5 hydroxyalkoxy, or R1 and R2 together with the carbon atom to which they are attached form a C3 to C6 cycloalkyl group.
    Type: Grant
    Filed: December 14, 2000
    Date of Patent: June 25, 2002
    Assignee: Clairol Incorporated
    Inventors: Mu-Ill Lim, Yuh-Guo Pan, Margaret Popp
  • Publication number: 20020016507
    Abstract: Process for the preparation of azine and of hydrazine by bringing ammonia, hydrogen peroxide and a reactant carrying a carbonyl group into contact with a working solution, comprising:
    Type: Application
    Filed: April 5, 2001
    Publication date: February 7, 2002
    Inventors: Georges Brenguer, Remi Jullin, Jean-Philippe Ricard
  • Publication number: 20010003136
    Abstract: Amines are prepared by reacting aldehydes or ketones at elevated temperature under elevated pressure with nitrogen compounds selected from the group of ammonia, primary and secondary amines, and with hydrogen in the presence of a catalyst, wherein the catalytically active mass of the catalyst contains, after its preparation and before the treatment with hydrogen, 22 to 45% by weight of oxygen-containing compounds of zirconium, calculated as ZrO2,
    Type: Application
    Filed: December 5, 2000
    Publication date: June 7, 2001
    Inventors: Jan Nouwen, Arthur Hohn, Horst Neuhauser, Frank Funke, Stephan Andreas Schunk, Johann-Peter Melder, Knut Eger, Michael Hesse, Joachim Wulff-Doring
  • Patent number: 6100430
    Abstract: An alicyclic polyamine of the formula (1) ##STR1## wherein Y.sub.1 represents a saturated aliphatic hydrocarbon group and R.sub.1 through R.sub.4 are the same or different and each represents hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, or an aralkyl group. The alicyclic polyamine can be obtained by subjecting a 3-formylcycloalkanone or 3-formylcycloalkenone to reductive amination reaction.
    Type: Grant
    Filed: September 10, 1998
    Date of Patent: August 8, 2000
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Kenichi Yamamoto, Kazuyuki Matsuoka, Hiroshi Yagihara
  • Patent number: 6072085
    Abstract: The method of the present invention provides a simple general route to a wide range of secondary amines.
    Type: Grant
    Filed: September 30, 1997
    Date of Patent: June 6, 2000
    Assignee: Massachusetts Institute of Technology
    Inventors: Xavier Verdaguer, Udo E. W. Lange, Stephen L. Buchwald
  • Patent number: 5885538
    Abstract: The present invention provides a method and composition regeneration of an aminal that has previously been reacted with a sulfide selected from hydrogen sulfide and mercaptans. The method includes contacting a scavenging mixture which includes an aminal, and an oxidation catalyst with a gas such as air, oxygen enriched air, oxygen, ozone enriched air and ozone. The composition includes an aminal, and an oxidation catalyst. The method and composition are useful for the regeneration of an aminal base sulfur scavenging compound.
    Type: Grant
    Filed: July 2, 1997
    Date of Patent: March 23, 1999
    Assignee: Quaker Chemical Corporation
    Inventors: Edward A. Trauffer, Muge Caglar
  • Patent number: 5861535
    Abstract: Tertiary aminoaryl compounds, such as N,N'dialkylaminoaryl compounds, are prepared using successive reductive steps without isolation therebetween, at high temperature and pressure. A nitroaryl compound is reduced using a ketone as both solvent and reactant in a reductive environment, and the resulting intermediate is further reacted with an aldehyde in the same reaction mixture without isolation to provide the second substituent on the amino group.
    Type: Grant
    Filed: September 23, 1997
    Date of Patent: January 19, 1999
    Assignee: Eastman Kodak Company
    Inventor: Victor L. Mylroie
  • Patent number: 5817877
    Abstract: A process of preparing an organic amine having at least one unsaturated group, such as an arylamine, involving contacting an unsaturated organic sulfonate, such as an aryl sulfonate, with a reactant amine, such as an alkyl or aryl amine, in the presence of a base and a transition metal catalyst under reaction conditions. The transition metal catalyst contains a Group 8 metal and a chelating ligand, for example a Group 15-substituted arylene or Group 15-substituted metallocene, such as 1,1'-bis(diphenylphosphino)-2,2'-binaphthyl or 1,1'-bis(diphenylphosphino)-ferrocene, respectively. The aryl sulfonate can be prepared from a phenol and sulfonating agent.
    Type: Grant
    Filed: September 19, 1997
    Date of Patent: October 6, 1998
    Assignee: Yale University
    Inventors: John F. Hartwig, Michael S. Driver, Janis Louie, Blake Hamann
  • Patent number: 5773656
    Abstract: Known (R)-1-aryl-alkylamines of the formula ##STR1## in whichR.sup.1 and Ar have the meanings indicated in the description, are prepared by a new process, which comprisesa) reacting a racemate of an ethyl or methyl 2-aryl-alkanoate of the formula ##STR2## with ammonia in the presence of a lipase which is suitable for the cleavage of esters, in the presence of a diluent,b) separating off from the reaction mixture the resulting (R)-2-aryl-alkanamide of the formula ##STR3## and then reacting it with sodium hypochlorite or sodium hypobromite in the presence of water.
    Type: Grant
    Filed: August 9, 1996
    Date of Patent: June 30, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventor: Uwe Stelzer
  • Patent number: 5739374
    Abstract: Diphenylheteroalkyl derivatives of the formula I ##STR1## where A and R.sup.1 -R.sup.6 have the meanings specified in the description, and the preparation thereof are described.The substances are suitable for controlling diseases and as cosmetic agents.
    Type: Grant
    Filed: February 14, 1997
    Date of Patent: April 14, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Janssen, Hans-Heiner Wuest
  • Patent number: 5665756
    Abstract: Novel aminoalkyloximes of the formula ##STR1## wherein: a. X is hydrogen, loweralkyl, loweralkoxy, halogen, trifluoromethyl, or a group of the formula ##STR2## wherein Y is hydrogen or loweralkyl, and p is 1 or 2; b. A is a group of the formula ##STR3## c. R.sup.1 and R.sup.2 are independently hydrogen or lowerakyl; and d. m is 2 to 6 and n is 0, or 2 to 6, inclusive, serotonin reuptake inhibitors, useful for treating depression and obsessive compulsive disorders are described. Also described are precursors of and processes for the preparation of such aminoakyloximes.
    Type: Grant
    Filed: August 3, 1994
    Date of Patent: September 9, 1997
    Assignee: Hoechst Marion Roussel, Inc.
    Inventors: Gregory M. Shutske, Brian S. Freed, John D. Tomer, IV, R. Richard L. Hamer
  • Patent number: 5616799
    Abstract: A process for the preparation of glycoloylanilide of the formula (G) ##STR1## is recited that involves reacting a nitrobenzene with hydrogen and, if desired, with a carbonyl compound, in the presence of a noble metal catalyst and a solvent, reacting the compound produced with chloroacetyl chloride, reacting the resulting product with a benzyl alcohol and with a base, or reacting the resulting compound with an O-benzylglycoloyl chloride, and debenzylating the resulting benzylglycoloylanilide product by reacting with hydrogen in the presence of a noble metal catalyst. The invention also relates to a process for the preparation of O-benzylglycoloylanilide.
    Type: Grant
    Filed: April 17, 1995
    Date of Patent: April 1, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Siegfried Planker, Theodor Papenfuhs
  • Patent number: 5536878
    Abstract: Disclosed are (1) a method for preparing an aromatic secondary amino compound which comprises reacting an N-cyclohexylideneamino compound in the presence of a hydrogen moving catalyst and a hydrogen acceptor by the use of a sulfur-free polar solvent and/or a cocatalyst, and (2) a method for preparing an aromatic secondary amino compound which comprises reacting cyclohexanone or a nucleus-substituted cyclohexanone, an amine and a nitro compound corresponding to the amine in a sulfur-free polar solvent in the presence of a hydrogen moving catalyst, a cocatalyst being added or not added. In a further aspect, a method is provided for the preparation of aminodiphenylamine by reacting phenylenediamine and cyclohexanone in the presence of a hydrogen transfer catalyst in a sulfur-free polar solvent while using nitroaniline as a hydrogen acceptor.
    Type: Grant
    Filed: December 2, 1994
    Date of Patent: July 16, 1996
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Teruyuki Nagata, Chiyuki Kusuda, Masaru Wada, Kenichi Satou, Masae Uchida
  • Patent number: 5436371
    Abstract: A process for preparing p-nitroaromatic amides is provided which comprises contacting a nitrile, nitrobenzene, a suitable base and water in the presence of a suitable solvent system to form a mixture, and reacting the mixture at a suitable temperature in a confined reaction zone in the presence of a controlled amount of protic material. The p-nitroaromatic amides of the invention can be reduced to p-aminoaromatic amides. In one embodiment, the p-aminoaromatic amide is further reacted with ammonia under conditions which produce the corresponding p-aminoaromatic amine and the amide corresponding to the nitrile starting material or with water in the presence of a suitable basic or acidic catalyst under conditions which produce the corresponding p-aminoaromatic amine and the acid or salt thereof corresponding to the nitrile starting material. In another embodiment, the p-aminoaromatic amine is reductively alkylated to produce alkylated p-aminoaromatic amine.
    Type: Grant
    Filed: August 29, 1994
    Date of Patent: July 25, 1995
    Assignee: Monsanto Company
    Inventors: Michael K. Stern, Brian K. Cheng
  • Patent number: 5395971
    Abstract: A process for making unsaturated .alpha.-amines from olefins wherein the process includes adding an aminating agent, an olefin and a molybdenum based catalyst to a reaction vessel having a nitrogen atmosphere. The catalyst may be described by the general formula LL'MoO.sub.2, L.sub.2 L'MoO.sub.2, or LL'MoO(X--Y).
    Type: Grant
    Filed: March 11, 1994
    Date of Patent: March 7, 1995
    Assignee: The Board of Regents of The University of Oklahoma
    Inventors: Kenneth M. Nicholas, Anurag S. Srivastava
  • Patent number: 5382690
    Abstract: Disclosed are(1) a method for preparing an aromatic secondary amino compound which comprises reacting an N-cyclohexylideneamino compound in the presence of a hydrogen moving catalyst and a hydrogen acceptor by the use of a sulfur-free polar solvent and/or a cocatalyst, and(2) a method for preparing an aromatic secondary amino compound which comprises reacting cyclohexanone or a nucleus-substituted cyclohexanone, an amine and a nitro compound corresponding to the amine in a sulfur-free polar solvent in the presence of a hydrogen moving catalyst, a cocatalyst being added or not added.
    Type: Grant
    Filed: August 2, 1993
    Date of Patent: January 17, 1995
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Teruyuki Nagata, Chiyuki Kusuda, Masaru Wada, Kenichi Satou
  • Patent number: 5371289
    Abstract: The present invention relates to a process for the preparation of a N-substituted-N'-phenyl-p-phenylenediamine of the formula: ##STR1## comprising reacting (a) a mixture of (1) N-phenyl-p-quinoneimine of the formula: ##STR2## and (2) p-hydroxydiphenylamine in a mole ratio of N-phenyl-p-quinoneimine to p-hydroxydiphenylamine of from 1.5:1 to 1:1.5 with (b) a primary amine of the formula:R.sup.1 --NH.sub.2in the presence of methanol wherein R.sup.1 is selected from the group of radicals consisting of alkyls having 1 to 20 carbon atoms, cycloalkyls having 6 to 8 carbon atoms and radicals of the structural formula: ##STR3## wherein R.sup.2 may be the same or different and is independently selected from the group of radicals consisting of hydrogen and an alkyl having 1 carbon atom, R.sup.3 is selected from the group of radicals consisting of an alkyl having 1 to 12 carbon atoms and n is an integer of from 0 to 6.
    Type: Grant
    Filed: March 22, 1993
    Date of Patent: December 6, 1994
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Kirkwood S. Cottman, Joseph A. Kuczkowski
  • Patent number: 5349109
    Abstract: A process for making unsaturated .alpha.-amines from olefins wherein the process includes adding an aminating agent, an olefin and a molybdenum based catalyst to a reaction vessel having a nitrogen atmosphere. The catalyst may be described by the general formula LL'MoO.sub.2, L.sub.2 L'MoO.sub.2, or LL'MoO(X-Y).
    Type: Grant
    Filed: August 26, 1993
    Date of Patent: September 20, 1994
    Assignee: The Board of Regents of the University of Oklahoma
    Inventors: Kenneth M. Nicholas, Anurag S. Srivastava
  • Patent number: 5344987
    Abstract: Optionally substituted diphenylamines can be obtained by reacting optionally substituted anilines with optionally substituted cyclohexanones over a supported catalyst at 200.degree.-450.degree. C. and 0.1-20 bar, the supported catalyst containing one or more metals having a dehydrogenating action selected from the group Ru, Pd, Os, Ir, Pt, Fe, Co, Ni, Re, Mn, Cu, Ag, Cr and Ce.
    Type: Grant
    Filed: July 16, 1993
    Date of Patent: September 6, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Otto Immel, Gerhard Darsow, Hans-Josef Buysch
  • Patent number: 5344983
    Abstract: Process for preparing a pentane-1,5-diamine of the formula ##STR1## where R.sup.1 represents a variety of organic radicals including alkyl which can bear substituents such as hydroxyl, halogen, alkoxy, carbalkoxy, carboxyl, alkylamino, cycloalkyl or aryl, andR.sup.2 and R.sup.3 independently of one another, represent hydrogen or have the same meanings as R.sup.1 or together are a C.sub.4 -C.sub.7 -alkylene chain which is unsubstituted or substituted by one to five C.sub.1 -C.sub.4 -alkyl groups,which comprises:(a) reacting a .gamma.-cyanoketone of the formula ##STR2## where R.sup.1, R.sup.2 and R.sup.3 have the meanings given above, with excess ammonia in a first reaction space on an acidic heterogeneous catalyst at 20.degree.-150.degree. C. and 15-500 bar, and(b) hydrogenating the resulting reaction product in a second separate reaction space in the presence of excess ammonia on a cobalt, nickel or noble metal catalyst at 50.degree.-180.degree. C. and 30-500 bar.
    Type: Grant
    Filed: August 26, 1992
    Date of Patent: September 6, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Tom Witzel, Eberhard Fuchs, Franz Merger, Claus-Ulrich Priester
  • Patent number: 5276193
    Abstract: A process for preparing an N-alkyl-substituted aminophenol is disclosed, comprising continuously feeding an aldehyde or a ketone to a reaction system containing an organic solvent, a catalyst for reduction, hydrogen, and an aminophenol to conduct a reductive alkylation reaction, wherein said reductive alkylation reaction is carried out while continuously adding an organic carboxylic acid into the reaction system. The process attains a high yield even when the catalyst is repeatedly used and does not cause corrosion of equipment.
    Type: Grant
    Filed: August 1, 1990
    Date of Patent: January 4, 1994
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Hiroshi Maki, Michihiro Kawasaki, Hiroshi Shimizu, Yoshiaki Ito
  • Patent number: 5231217
    Abstract: The present invention is directed to a novel solvent-free process for preparing amine terminated compounds by reacting a polyfunctional acetoacetic acid ester with either ammonia or an organic compound which contains one or more primary amino groups in the presence of an acidic catalyst selected from the group consisting of (i) boron trifluoride etherate and (ii) organic acids having pKa values of from 0.1 to 0.8.
    Type: Grant
    Filed: March 20, 1991
    Date of Patent: July 27, 1993
    Assignee: Miles Inc.
    Inventors: Robert P. Yeater, Robson Mafoti, Josef Sanders
  • Patent number: 5221770
    Abstract: A process is disclosed for the preparation of 2-amino-5,6-dimethoxy-tetralin, which is a useful intermediate for the preparation of pharmacologically active chemical compounds.
    Type: Grant
    Filed: September 25, 1992
    Date of Patent: June 22, 1993
    Assignee: Zambon Group S.p.A.
    Inventors: Giorgio Bertolini, Cesare Casagrande, Francesco Santangelo
  • Patent number: 5202485
    Abstract: A process for preparing an N-alkylaminophenol is disclosed, comprising subjecting an aminophenol to reductive alkylation with an aldehyde or a ketone in the presence of an organic solvent and hydrogen, wherein the reductive alkylation is carried out at a temperature of from 20.degree. to 70.degree. C. in the further presence of a catalyst for reduction comprising platinum and at least one metal element selected from metal elements belonging to the IB group, IIB group, IVB group, VB group, and VIB group of the Periodic Table, supported on activated carbon, or comprising palladium and at least one metal element selected from metal elements belonging to the IB group, IIB group, IVB group, VB group and VIB group of the Periodic Table, supported on activated carbon.
    Type: Grant
    Filed: April 29, 1991
    Date of Patent: April 13, 1993
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Hiroshi Maki, Michihiro Kawasaki, Horishi Shimizu, Yoshiaki Ito
  • Patent number: 5066824
    Abstract: The present invention is directed to a process for preparing amine terminated compounds by reacting a polyfunctional acetoacetic acid ester with either ammonia or an organic compound which contains one or more primary amino groups in the presence of a solvent and an acidic catalyst selected from the group consisting of (i) boron trifuloride etherate and (ii) organic acids having pKa values of from 0.1 to 0.8 with the proviso that if the primary amino group containing compound contains no aromatically bound amino groups, the pKa of said organic acid is from 0.1 to less than 0.7.
    Type: Grant
    Filed: August 3, 1990
    Date of Patent: November 19, 1991
    Assignee: Mobay Corporation
    Inventors: Robson Mafoti, Josef Sanders
  • Patent number: 5053540
    Abstract: The present invention relates to a process for the preparation of a p-aminodiphenylamine comprising reacting N-phenylquinoneimine of the formula: ##STR1## with ammonia, ammonium hydroxide or mixtures thereof, wherein the molar ratio of N-phenylquinoneimine to NH.sub.3 in the reaction mixture ranges from about 1:1 to 1:80.
    Type: Grant
    Filed: March 8, 1990
    Date of Patent: October 1, 1991
    Assignee: The Goodyear Tire & Rubber Company
    Inventor: Kirkwood S. Cottman
  • Patent number: 4774359
    Abstract: The synthesis and characterization of several polyenamine ketones are discussed wherein conjugated diacetylenic diketones and aromatic diamines are used as a route to the formation of high molecular weight polyenamine ketones which exhibit good mechanical properties and can be cast into creasible films. Typical polymerization conditions involved the reaction of stoichiometric amounts of 1,4- or 1,3-PPPO and a diamine at 60.degree.-130.degree. C. in m-cresol at (w/w) solids content of 8-26% for a specified period of time under a nitrogen atmosphere. Novel polyenamine ketones were prepared with inherent viscosities as high as 1.99 dl/g and tough, clear amber films with tensile strengths of 12,400 psi and tensile moduli of 397,000 psi were cast from solutions of the polymers in chloroform. The polymers exhibited T.sub.g s as high as 235.degree. C. and weight losses of 14% after aging at 232.degree. C. in circulating air for sixty hours.
    Type: Grant
    Filed: January 5, 1987
    Date of Patent: September 27, 1988
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: Paul M. Hergenrother, Robert G. Bass, Mark S. Sinsky, John W. Connell
  • Patent number: 4730075
    Abstract: A process for the production of (1) an ether or (2) a second amine comprises reacting an activated olefin with respectively an alcohol or first amine in the presence of a catalyst which is either (a) an amidine or (b) a Lewis base and epoxide. The same catalyst may also be used to carry out the reverse reaction in which an activated olefin and an alcohol or first amine are produced from the appropriate ether or second amine.
    Type: Grant
    Filed: June 20, 1986
    Date of Patent: March 8, 1988
    Assignee: BP Chemicals Limited
    Inventor: Michael J. Green
  • Patent number: 4663483
    Abstract: The synthesis and characterization of several polyenamine ketones are discussed wherein conjugated diacetylenic diketones and aromatic diamines are used as a route to the formation of high molecular weight polyenamine ketones which exhibit good mechanical properties and can be cast into creasible films. Typical polymerization conditions involved the reaction of stoichiometric amounts of 1,4- or 1,3-PPPO and a diamine at 60.degree.-130.degree. C. in m-cresol at (w/w) solids content of 8-26% for a specified period of time under a nitrogen atmosphere. Novel polyenamine ketones were prepared with inherent viscosities as high as 1.99 dl/g and tough, clear amber films with tensile strengths of 12,400 psi and tensile moduli of 397,000 psi were cast from solutions of the polymers in chloroform. The polymers exhibited T.sub.g s as high as 235.degree. C. and weight losses of 14% after aging at 232.degree. C. in circulating air for sixty hours.
    Type: Grant
    Filed: May 15, 1985
    Date of Patent: May 5, 1987
    Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space Administration
    Inventors: Paul M. Hergenrother, Robert G. Bass, Mark S. Sinsky, John W. Connell
  • Patent number: 4621158
    Abstract: A method for making amines by reacting alcohols and/or aldehydes with primary and/or secondary amines or with ammonia in the presence of a catalyst at elevated temperature, and optionally at elevated pressure, in the liquid phase, the catalyst being an unsupported catalyst consisting of a combination of copper and tin compounds.
    Type: Grant
    Filed: August 21, 1985
    Date of Patent: November 4, 1986
    Assignee: Schering Aktiengesellschaft
    Inventors: Hans-Juergen Hubert, Klaus D. Tillmetz
  • Patent number: 4506039
    Abstract: Polymer-containing polyether polyamines containing terminal aromatically-bound amino groups are produced by in situ polymerization of a polyether polyamine with an olefinically unsaturated monomer. The polyether polyamine starting material must have terminal aromatic amino groups, a molecular weight of from 800 to 10,000 and an aromatic amino group content of from 0.3 to 16 wt. %. Suitable olefinically unsaturated monomers include .alpha.,.beta.-unsaturated nitriles, aromatic vinyl compounds, .alpha.,.beta.-unsaturated carboxylic acids and esters thereof, vinyl esters, vinyl halides, vinylidene halides, .alpha.,.beta.-unsaturated carboxylic acid amides and aminoalkyl esters of unsaturated carboxylic acids. Acrylonitrile/styrene mixtures are preferred monomers. The starting materials are employed in quantities such that the product modified polyether polyamine contains from 1 to 60 wt. % polymer or graft-polymer. The product polyamines are particularly useful in the production of polyurethanes.
    Type: Grant
    Filed: December 20, 1982
    Date of Patent: March 19, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Balle, Werner Rasshofer, Winfried Schoberth
  • Patent number: 4480140
    Abstract: Phenols alkylated in the ortho and/or para positions are produced in good yields and in the absence of isomers from phenolic compounds having at least two alkylateable ortho-ortho or ortho-para positions open. The phenolic compound is first partially chlorinated or brominated and the desired halogenated phenol having at least one open position ortho or para is reacted with an aldehyde having one to four carbon atoms and a secondary non-aromatic amine. The reaction is conducted in the liquid phase with a stoichiometric amount of the phenolic compound and stoichiometric or excess of stoichiometric amounts of the aldehyde and the amine. The reaction is performed at a temperature of from about 0.degree. C. to about 100.degree. C. to produce an aminoalkylated halogenated phenolic compound. This aminoalkylated halogenated phenolic compound is contacted with hydrogen in the presence of a metal catalyst at a temperature of about 100.degree. C. to about 175.degree. C.
    Type: Grant
    Filed: March 16, 1983
    Date of Patent: October 30, 1984
    Assignee: Koppers Company, Inc.
    Inventor: Gerd Leston