By Replacing Hydroxy Patents (Class 564/402)
  • Patent number: 9359390
    Abstract: An activated carbon having a high catalytic activity as an oxidation catalyst or a decomposition catalyst, and use therefor are provided. The activated carbon has (a) an oxygen content in a range from 1.40 to 4.30% by mass, (b) a nitrogen content in a range from 0.90 to 2.30% by mass, (c) a sulfur content in a range from 0.50 to 1.20% by mass, and (d) a hydrogen content in a range from 0.40 to 0.65% by mass. The activated carbon may have at least one characteristic of (e) an amount of an acidic surface functional group of 0.10 to 0.36 meq/g, (f) an amount of a basic surface functional group of 0.50 to 1.30 meq/g, and (g) a benzene adsorption capacity of 25 to 50%. The activated carbon catalyzes an oxidation reaction of N-(phosphonomethyl)iminodiacetic acid with a peroxide (e.g., hydrogen peroxide) and achieves an efficient production of N-(phosphonomethyl)glycine even after repetitive use. The activated carbon also efficiently decomposes a chloramine.
    Type: Grant
    Filed: March 24, 2011
    Date of Patent: June 7, 2016
    Assignee: Kuraray Chemical Co., Ltd.
    Inventors: Mitsunori Hitomi, Takayuki Yoshikawa, Takayuki Yamada
  • Patent number: 9006489
    Abstract: Method for pretreating the copper-based catalyst having the steps of dehydrating the copper-based catalyst at an elevated temperature, reducing the dehydrated copper-based catalyst with hydrogen, and passivating the activated copper-based catalyst to obtain a catalyst suitable for N-alkylation. The dehydration and reduction steps may be conducted simultaneously.
    Type: Grant
    Filed: June 15, 2011
    Date of Patent: April 14, 2015
    Assignee: Jiangsu Sinorgchem Technology Co., Ltd.
    Inventor: Shiming Gao
  • Patent number: 8946463
    Abstract: The present invention relates to a chemocatalytic liquid-phase process for the direct one-stage amination of alcohols to primary amines by means of ammonia in high yields using a catalyst system containing at least one transition metal compound and a xantphos ligand.
    Type: Grant
    Filed: December 14, 2011
    Date of Patent: February 3, 2015
    Assignee: Evonik Degussa GmbH
    Inventors: Florian Klasovsky, Thomas Tacke, Jan Christoph Pfeffer, Thomas Haas, Matthias Beller, Andreas Martin, Jens Deutsch, Angela Koeckritz, Sebastian Imm, Juergen Haberland
  • Publication number: 20140046054
    Abstract: The invention relates to a process for preparing amines (A) by alcohol amination of alcohols (Al) by means of an aminating agent (Am) with elimination of water, wherein the alcohol amination is carried out in the presence of a complex catalyst comprising iridium and an amino acid.
    Type: Application
    Filed: August 7, 2013
    Publication date: February 13, 2014
    Applicant: BASF SE
    Inventors: Alexander WETZEL, Michael Limbach, Marion Brinks, Mathias Schelwies
  • Publication number: 20140039181
    Abstract: The invention relates to a method for producing a N-substituted amine compound by catalyzed alkylation. The method uses amine and alcohol or two kinds of amines as the reaction materials, employs composite metal oxides catalyst at a reaction temperature of 80-180° C. to catalyze the reaction for 6-36 hours, so as to produce the N-substituted amine compound. The reaction condition of the method of the invention is relatively moderate, using a catalyst made of cheap non-noble metals, which is non-caustic and easy to be separated and reused. The reaction does not need any medium and has relatively high conversion rate and selectivity.
    Type: Application
    Filed: December 28, 2012
    Publication date: February 6, 2014
    Applicant: Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences
    Inventor: Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences
  • Publication number: 20130331580
    Abstract: The present invention relates to a chemocatalytic liquid-phase process for the direct one-stage amination of alcohols to primary amines by means of ammonia in high yields using a catalyst system containing at least one transition metal compound and a xantphos ligand.
    Type: Application
    Filed: December 14, 2011
    Publication date: December 12, 2013
    Applicant: EVONIK DEGUSSA GmbH
    Inventors: Florian Klasovsky, Thomas Tacke, Jan Christoph Pfeffer, Thomas Haas, Matthias Beller, Andreas Martin, Jens Deutsch, Angela Koeckritz, Sebastian Imm, Juergen Haberland
  • Publication number: 20130245276
    Abstract: The present invention relates to a process for preparing primary amines comprising the process steps A) provision of a solution of a primary alcohol in a fluid, nongaseous phase, B) contacting of the phase with free ammonia and/or at least one ammonia-releasing compound and a homogeneous catalyst and optionally C) isolation of the primary amine formed in process step B), characterized in that the volume ratio of the volume of the liquid phase to the volume of the gas phase in process step B is greater than 0.05 and/or in that process step B is carried out at pressures greater than 10 bar.
    Type: Application
    Filed: December 7, 2011
    Publication date: September 19, 2013
    Applicant: Evonik Degussa GmbH
    Inventors: Florian Klasovsky, Jan Christoph Pfeffer, Thomas Tacke, Thomas Haas, Matthias Beller, Angela Koeckritz, Jens Deutsch, Andreas Martin, Sebastian Imm
  • Publication number: 20130090445
    Abstract: The present invention provides a synthesis system that can synthesize aniline and/or styrene efficiently, a synthesis system that can synthesize butadiene (1,3-butadiene) efficiently, a rubber chemical for a tire which is synthesized from the aniline obtained by the synthesis system, a synthetic rubber for a tire which is synthesized from the styrene and/or butadiene obtained by the synthesis systems, and a pneumatic tire produced using the rubber chemical for a tire and/or the synthetic rubber for a tire. The present invention relates to a synthesis system for synthesizing aniline and/or styrene from an alcohol having two or more carbon atoms via an aromatic compound.
    Type: Application
    Filed: January 25, 2012
    Publication date: April 11, 2013
    Applicant: SUMITOMO RUBBER INDUSTRIES, LTD.
    Inventors: Takayuki Hattori, Takao Wada, Keitaro Fujikura, Yuka Yokoyama, Toshiro Matsuo
  • Publication number: 20120316363
    Abstract: Method for pretreating the copper-based catalyst having the steps of dehydrating the copper-based catalyst at an elevated temperature, reducing the dehydrated copper-based catalyst with hydrogen, and passivating the activated copper-based catalyst to obtain a catalyst suitable for N-alkylation. The dehydration and reduction steps may be conducted simultaneously.
    Type: Application
    Filed: June 15, 2011
    Publication date: December 13, 2012
    Applicant: Jiangsu Sinorgchem Technology Co., Ltd.
    Inventor: SHIMING GAO
  • Publication number: 20120071692
    Abstract: A process for preparing an aromatic amine by reacting a corresponding aromatic alcohol with an aminating agent selected from the group consisting of ammonia, primary amines and secondary amines, in the presence of hydrogen and a catalyst molding, at a temperature of from 60-300°. The catalyst molding comprises Zr, Pd and Pt and has an annular tablet form with an external diameter in the range from 2-6 mm, a height in the range from 1-4 mm and an internal diameter of from 1-5 mm or a topologically equivalent form with the same volume. Catalyst moldings comprising Zr, Pd and Pt are also provided. The catalyst molding has an annular tablet form with an external diameter in the range from 3-6 mm, a height in the range from 1-4 mm and an internal diameter of from 2-5 mm or a topologically equivalent form.
    Type: Application
    Filed: September 16, 2011
    Publication date: March 22, 2012
    Applicant: BASF SE
    Inventors: SEBASTIAN AHRENS, Christoph Mueller, Axel Paul, Martin Ernst, Nadja Pollmer, Johann-Peter Melder, Thomas Heidemann, Joachim-Thierry Anders, Bram Willem Hoffer
  • Patent number: 8134030
    Abstract: A process for preparing a primary amine with a tertiary alpha-carbon atom by reacting a tertiary alcohol with ammonia in the presence of a heterogeneous catalyst, by performing the reaction in the presence of a non-microporous, non-zeolitic aluminosilicate as a catalyst, where the aluminosilicate has a molar Al/Si ratio in the range from 0.1 to 30.
    Type: Grant
    Filed: October 14, 2008
    Date of Patent: March 13, 2012
    Assignee: BASF SE
    Inventors: Marcus Sigl, Thomas Heidemann
  • Patent number: 7754922
    Abstract: Processes comprising: (i) providing a reactant selected from the group consisting of primary alcohols, secondary alcohols, aldehydes, ketones and mixtures thereof; and (ii) reacting the reactant with hydrogen and a nitrogen compound selected from the group consisting of ammonia, primary amines, secondary amines and mixtures thereof, in the presence of a catalyst comprising a zirconium dioxide- and nickel-containing catalytically active composition, to form an amine; wherein the catalytically active composition, prior to reduction with hydrogen, comprises oxygen compounds of zirconium, copper, nickel and cobalt, and one or more oxygen compounds of molybdenum in an amount of 5.5 to 12% by weight, calculated as MoO3.
    Type: Grant
    Filed: July 4, 2007
    Date of Patent: July 13, 2010
    Assignee: BASF SE
    Inventors: Petr Kubanek, Bram Willem Hoffer, Ekkehard Schwab, Johann-Peter Melder, Holger Evers, Till Gerlach
  • Patent number: 7547805
    Abstract: The present invention relates to a process for the production of severely sterically hindered amino-ether alcohols using a catalyst based on the combination of one or more catalytically active metals supported in a dispersed form on one or more ordered mesoporous materials as support.
    Type: Grant
    Filed: February 1, 2005
    Date of Patent: June 16, 2009
    Assignee: Exxonmobil Research and Engineering Company
    Inventors: Andrzej Malek, Christine Nicole Elia, Adeana Richelle Bishop, Edmund John Mozeleski, Michael Siskin
  • Publication number: 20090076306
    Abstract: A process for continuously preparing a primary aromatic amine by reacting a corresponding cycloaliphatic alcohol with ammonia in the presence of hydrogen at a temperature in the range from 80 to 350° C. in the presence of a heterogeneous catalyst, wherein the catalytically active composition of the catalyst, before its reduction with hydrogen, comprises from 90 to 99.8% by weight of zirconium dioxide (ZrO2), from 0.1 to 5.0% by weight of oxygen compounds of palladium and from 0.1 to 5.0% by weight of oxygen compounds of platinum.
    Type: Application
    Filed: December 21, 2006
    Publication date: March 19, 2009
    Applicant: BASF SE
    Inventors: Frank Haese, Joachim Wulff-Doring, Ulrich Kohler, Peter Gaa, Frank-Friedrich Pape, Johann-Peter Melder, Manfred Julius
  • Patent number: 7183438
    Abstract: Disclosed are catalysts, the catalytically active mass of which contains 22 to 40 percent by weight of oxygen-containing compounds of zirconium, calculated as ZrO2, 1 to 30 percent by weight of oxygen-containing compounds of copper, calculated as CuO, 15 to 50 percent by weight of oxygen-containing compounds of nickel, calculated as NiO, the molar ratio between nickel and copper being greater than 1, 15 to 50 percent by weight of oxygen-containing compounds of cobalt, calculated as CoO, and less than 1 percent by weight of an alkali metal, calculated as alkali metal oxide, prior to being treated with hydrogen. Also disclosed is a method for the production of amines by reacting primary and secondary alcohols, aldehydes, or ketones with hydrogen and nitrogen compounds selected from the group ammonia, primary and secondary amines, in the presence of said catalysts at an elevated temperature and an elevated pressure.
    Type: Grant
    Filed: March 7, 2003
    Date of Patent: February 27, 2007
    Assignee: BASF Aktiengesellschaft
    Inventors: Till Gerlach, Frank Funke, Johann-Peter Melder, Stefan Iselborn, Martin Rudloff, Michael Hüllmann
  • Patent number: 7034186
    Abstract: Process for preparing an amine by reacting a primary or secondary alcohol, aldehyde or ketone with hydrogen and a nitrogen compound selected from the group consisting of ammonia and primary and secondary amines in the presence of 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: April 25, 2006
    Assignee: BASF Aktiengesellschaft
    Inventors: Till Gerlach, Frank Funke, Johann-Peter Melder
  • Patent number: 6953866
    Abstract: A process is disclosed for preparing ortho substituted phenylamines comprising contacting phenylhydroxylamine, optionally substituted with at least one inert substituent, with a nucleophilic reagent in the presence of a manganese oxide at a temperature between about 10° C. and about 170° C. and a pressure from subatmospheric to superatmospheric such that an ortho substituted phenylamine, optionally correspondingly substituted with at least one inert substituent, is predominantly formed.
    Type: Grant
    Filed: January 30, 2004
    Date of Patent: October 11, 2005
    Assignee: Crompton Corporation
    Inventors: Russell E. Malz, Jr., Ranjit Kumar, Luis Javier Garces, Steven L. Suib
  • Patent number: 6737460
    Abstract: Vinyl monomers having polyenic side chains derived from highly unsaturated fatty acids represented by the general formula: R1COOH wherein R1 is a C19-24 hydrocarbon having 5 or 6 unsaturated bonds, and the derivatives thereof. Vinyl monomers having polyenic side chains derived from highly polyunsaturated fatty acids and the polymers of said monomers can be provided. In addition polymers having double bonds in the side chain into which various functional groups can be introduced can be provided. Useful utilization of fatty acid esters remaining as the residue in distillation of fish oil can be provided.
    Type: Grant
    Filed: July 17, 1998
    Date of Patent: May 18, 2004
    Assignee: Nippon Suisan Kaisha, Ltd.
    Inventors: Nobushige Doisaki, Shuji Jinno, Kazuhiko Hata, Takeshi Endo
  • Patent number: 6706217
    Abstract: Liquid antiozonant mixtures obtained from the process comprising simultaneously reacting at least one unsubstituted and/or substituted paraphenylenediamine compound with a carbonyl compound mixture comprising acetone and at least one other carbonyl compound selected from the group consisting of ketones containing from 4 to about 12 carbon atoms, aldehydes containing from 1 to about 12 carbon atoms and mixtures thereof in the presence of a reductive alkylation catalyst is provided. Rubber compositions containing the liquid antiozonant mixtures is also provided.
    Type: Grant
    Filed: October 22, 2001
    Date of Patent: March 16, 2004
    Assignee: Uniroyal Chemical Company, Inc.
    Inventors: Russell E. Malz, Jr., Michael P. Reynolds, Richard A. Gencarelli
  • Patent number: 6706216
    Abstract: Liquid antiozonant mixtures obtained from the process comprising simultaneously reacting at least one unsubstituted and/or substituted paraphenylenediamine compound with a carbonyl compound mixture comprising acetone and at least one other carbonyl compound selected from the group consisting of ketones containing from 4 to about 12 carbon atoms, aldehydes containing from 1 to about 12 carbon atoms and mixtures thereof in the presence of a reductive alkylation catalyst is provided. Rubber compositions containing the liquid antiozonant mixtures is also provided.
    Type: Grant
    Filed: April 19, 2000
    Date of Patent: March 16, 2004
    Assignee: Uniroyal Chemical Company, Inc.
    Inventors: Russell E. Malz, Jr., Michael P. Reynolds, Richard A. Gencarelli
  • Publication number: 20020147366
    Abstract: Process for the preparation of alkoxylated tertiary and quaternary amine surfactants by reductive amination of alkoxylated alcohols with anhydrous ammonia or primary or secondary amines or polyamines, optionally followed by quaternization of the alkoxylated tertiary amines with a quaternizing agent such as an aliphatic halide.
    Type: Application
    Filed: June 29, 2001
    Publication date: October 10, 2002
    Inventors: Michael S. Wiggins, Reuben Grinstein, Dharmesh Chovatia
  • Publication number: 20020082455
    Abstract: Amines of the formula (I)
    Type: Application
    Filed: October 24, 2001
    Publication date: June 27, 2002
    Inventors: Shelue Liang, Frank Funke, Arthur Hohn
  • Patent number: 6403834
    Abstract: The invention concerns a method for preparing tris(ether-amines) of formula (I): N[A—O—(B—O)n—R]3 wherein R, A, B and n are as defined in Claim 1, comprising the reaction, in liquid phase, of an alkylene-glycol monoether of formula (II): HO—A—O—(B—O)nR wherein R, A, B and n are as defined in Claim 1, with an ammonolysis agent selected among ammonia and an etheramine of formula (I′): H3-pN[A—O—(B—O)nR]p wherein: A, B, n and R are as defined in Claim 1 and p represent 1 or 2, at a temperature ranging between 100 and 250° C., by contacting reagents with a hydrogenation-dehydrogenation catalyst.
    Type: Grant
    Filed: July 23, 2001
    Date of Patent: June 11, 2002
    Assignee: Rhodia Chimie
    Inventors: Michel Alas, Albert Bouniot
  • Patent number: 6281240
    Abstract: This invention provides methods of treating secretory diarrhea or cystic fibrosis in a mammal which comprises administering to a mammal in need thereof an effective amount of diarylsulfonylurea. This invention also describes specific diarylsulfonylureas for use in treating secretory diarrhea or cystic fibrosis.
    Type: Grant
    Filed: January 31, 2000
    Date of Patent: August 28, 2001
    Assignee: Eli Lilly and Company
    Inventor: Bruce D Schultz
  • Patent number: 6268535
    Abstract: The present invention is a method of preparing a 3-aryl-1-indanamine represented by structural formula I: and physiologically acceptable salts thereof. In structure I, phenyl ring A can be unsubstituted or substituted with 1-4 substitutents. R1 is an aromatic group which can be substituted or unsubstituted. R2 and R3 are each, independently, hydrogen, an aliphantic group, a substituted aliphatic group, an aromatic group, a substituted aromatic group, an aralkyl group, or a substituted aralkyl group. Alternatively, R2 and R3, taken together with the nitrogen substitutent on the indan ring, form a non-aromatic ring system having 1-2 heteroatoms.
    Type: Grant
    Filed: January 7, 1999
    Date of Patent: July 31, 2001
    Assignee: Pharm-Eco Laboratories, Inc.
    Inventors: Adel M. Moussa, Reem Haider, Heather Taft, Jurjus Jurayj, Weiheng Wang, HaeSuk Suh
  • Patent number: 5986138
    Abstract: The present invention relates to a process for the preparation of alkylated aromatic amines which comprises reacting an aromatic amine selected from aniline, toludine, xylidine, N-methyl aniline, N-ethyl aniline, m-ethyl aniline, p-ethyl aniline, o-ethyl aniline with a primary or secondary alcohol selected from ethanol, methanol, isopropyl alcohol in the presence of attalpulgite impregnated with combination of iron oxide and oxides selected from transition metals of the periodic table as a catalyst prepared by the method described and claimed in our co-pending U.S. patent application Ser. No. 09/047,718 at atmospheric pressure and at a temperature in the range of 300-400.degree. C. and recovering the desired amine by conventional methods.
    Type: Grant
    Filed: March 25, 1998
    Date of Patent: November 16, 1999
    Assignee: Council of Scientific & Industrial Research
    Inventors: Bankupalli Satyavathi, Akash Narhar Rao Patwari, Uday Triambakraj Bhalerao
  • Patent number: 5925789
    Abstract: The present invention provides novel methods for the asymmetric synthesis of (S)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1- benzoxazin-2-one of formula (VI-i) ##STR1## which is useful as a human immunodeficiency virus (HIV) reverse transcriptase inhibitor.
    Type: Grant
    Filed: April 6, 1998
    Date of Patent: July 20, 1999
    Assignee: DuPont Pharmaceuticals Company
    Inventors: Michael E. Pierce, Cheng Y. Chen, Anusuya Choudhury, Lilian A. Radesca, Lushi Tan, Dalian Zhao
  • 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: 5689007
    Abstract: Processes of preparing para substituted phenylamines, such as, p-phenylenediamines, and particularly, p-aminodiphenylamine. One process involves contacting phenylhydroxylamine with a nucleophilic reagent, such as aniline, in specified proportions and within a specified temperature range, in the absence of oxygen, and in the presence of a homogeneous acid catalyst, such as hydrochloric acid. A second process involves contacting phenylhydroxylamine with a nucleophilic reagent, such as aniline, in the presence of a solid acid catalyst, such as acidic zeolite Y, under reaction conditions.
    Type: Grant
    Filed: October 7, 1996
    Date of Patent: November 18, 1997
    Assignee: Uniroyal Chemical Company, Inc.
    Inventors: Russell Edward Malz, Gerard V. Smith, Mark Peter Ferrandino, Ruozhi Song, Chung-Yuan Lin, Franklin Herbert Barrows
  • Patent number: 5663438
    Abstract: A process for the preparation of a phenyl amine which may be substituted by alkyl or cycloalkyl in which the corresponding cyolohexylamine is reduced at temperatures of 150.degree. to 300.degree. C. and pressures of 0.01 to 50 bar in the presence of a heterogeneous dehydrogenation catalyst consisting essentially of palladium or a palladium/platinum mixture supported on carrier consisting of the oxides of rare earth metals and and metals of Group IVb of the Periodic Table of Elements, with the proviso that the palladium/platinum mixture may also be supported on an alumina carrier. The cyclohexylamine reactant can be advantageously prepared by reacting the corresponding phenol with ammonia and hydrogen at 100.degree. to 250.degree. C. in the presence of the same heterogeneous catalyst as a preliminary step to provide a two stage process using the same catalyst in both stages.
    Type: Grant
    Filed: August 17, 1995
    Date of Patent: September 2, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Ulrich Kohler, Frank-Friedrich Pape, Matthias Irgang, Joachim Wulff-Doring, Michael Hesse, Peter Polanek
  • Patent number: 5614647
    Abstract: The present invention provides a novel synthesis of the compounds of Formula (I): ##STR1## The compounds are produced in high yield and without utilizing expensive chromatographic separations. The synthesis is particularly advantageous because it is stereoselective.
    Type: Grant
    Filed: May 25, 1995
    Date of Patent: March 25, 1997
    Assignee: Eli Lilly and Company
    Inventors: Margaret M. Faul, Michael R. Jirousek, Leonard L. Winneroski, II
  • Patent number: 5574187
    Abstract: Processes of preparing para substituted phenylamines, such as, p-phenylenediamines, and particularly, p-aminodiphenylamine. One process involves contacting phenylhydroxylamine with a nucleophilic reagent, such as aniline, in specified proportions and within a specified temperature range, in the absence of oxygen, and in the presence of a homogeneous acid catalyst, such as hydrochloric acid. A second process involves contacting phenylhydroxylamine with a nucleophilic reagent, such as aniline, in the presence of a solid acid catalyst, such as acidic zeolite Y, under reaction conditions.
    Type: Grant
    Filed: October 6, 1994
    Date of Patent: November 12, 1996
    Assignee: Uniroyal Chemical Company, Inc.
    Inventors: Russell E. Malz, Gerard V. Smith, Mark P. Ferrandino, Ruozhi Song, Chung-Yuan Lin, Franklin H. Barrows
  • Patent number: 5545753
    Abstract: The process for preparing anilines by reaction of phenols with an amination agent in accordance with the present invention is disclosed, which process is characterized by carrying out the reaction of phenols with an amination agent in the presence of a low alkali and weakly acidic alumina catalyst having the alkali oxide content of less than 0.5% by weight, said alumina catalyst being obtained by firing an alumina catalyst containing in a dry state more than 80% by weight of alumina and less than 20% by weight of silica at a temperature of 600.degree.-900.degree. C., followed by acid treatment. According to the present invention, there are obtained such excellent effects that even when the reaction is carried out at a temperature lower than those employed in the case of conventionally well-known catalysts, the desired anilines can be prepared in high yields and high selectivity and, moreover, a high catalyst activity can be maintained over a long period of time.
    Type: Grant
    Filed: March 28, 1994
    Date of Patent: August 13, 1996
    Assignee: Mitsui Petrochemical Industries, Ltd.
    Inventors: Mitsuki Yasuhara, Yuuichirou Tatsuki, Mitsunori Nakamura, Fujihisa Matsunaga
  • Patent number: 5489710
    Abstract: A regioselective processes are disclosed for the synthesis of (1R,1S)-amino-(2S,2R)-alkanol, particularly (1R,1S)-amino-(2S,2R)-indanol.
    Type: Grant
    Filed: April 19, 1995
    Date of Patent: February 6, 1996
    Assignee: Merck & Co., Inc.
    Inventors: Thomas R. Verhoeven, F. Edward Roberts, Chris H. Senanayake, Kenneth M. Ryan
  • Patent number: 5449829
    Abstract: A diphenylamine with both the phenyl groups being substituted is prepared by reacting a phenol with ammonia in the presence of a hydrogen transfer catalyst and a cyclohexanone; or by converting a portion of the phenol to the cyclohexanone in the presence of a hydrogen transfer catalyst and under hydrogen pressure and then reacting the remaining portion of the phenol with ammonia in the presence of the cyclohexanone so converted and the hydrogen transfer catalyst. The diphenylamine can be obtained very efficiently.
    Type: Grant
    Filed: June 15, 1994
    Date of Patent: September 12, 1995
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Chiyuki Kusuda, Masaru Wada, Teruyuki Nagata
  • Patent number: 5371294
    Abstract: Cyclohexylamine and dicyclohexylamine can be prepared as a mixture with one another by reaction of phenol with aniline, ammonia or a mixture of aniline and ammonia in the presence of hydrogen over a catalyst, the reaction being carried out according to the invention over a palladium catalyst which has a support of niobic acid or tantalic acid or a mixture of niobic acid and tantalic acid or a support containing such acids. The reaction is carried out at 100.degree.-220.degree. C. under an H.sub.2 partial pressure of 0.5-500 bar.
    Type: Grant
    Filed: October 2, 1992
    Date of Patent: December 6, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Otto Immel, Hans-Josef Buysch, Gerhard Darsow
  • Patent number: 5371290
    Abstract: A process for the preparation of N,N-dialkylarylamines (I) by reacting arylamines (II) with alcohols (IIIa) or dialkyl ethers (IIIb) in the presence of an oxygen acid of phosphorus or in the presence of an ammonium salt thereof as catalyst, comprises reacting the oxygen acid of phosphorus with an arylamine (IV) before the reaction is commenced. The invention also relates to the regeneration of the catalyst by occasionally interrupting the reaction and treating the catalyst phase at from 100.degree. to 300.degree. C. with steam or water.
    Type: Grant
    Filed: January 31, 1994
    Date of Patent: December 6, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Reuter, Willi A. Weber, Hans Diem
  • Patent number: 5344984
    Abstract: A method for preparing "twin-tailed" tertiary amines which have two moles of alkoxylated phenol bonded to each nitrogen function of a molecule of methylamine and represented by the formula: ##STR1## wherein x represents zero to about 30 which comprises alkylating a mole of methylamine with two moles of alkoxylated alkylphenol over a catalyst comprising:5 to 70% nickel;1 to 20% copper;0.1 to 10% chromium; and0.1 to 10% molybdenum on an alumina support.
    Type: Grant
    Filed: April 8, 1993
    Date of Patent: September 6, 1994
    Assignee: Texaco Chemical Company
    Inventors: John F. Knifton, Carter G. Naylor
  • Patent number: 5288911
    Abstract: Preparation of .alpha.,.omega.-aminoalcohols of the general formula IHO--CH.sub.2 --X--CH.sub.2 --NH.sub.2 (I),in which x denotes a C.sub.1 -C.sub.20 -alkylene chain optionally substituted by inert radicals and/or optionally interrupted by oxygen or nitrogen,by the reaction of .alpha.,.omega.-alkanediols of the general formula IIHO--CH.sub.2 --X--CH.sub.2 --OH (II),in which the connecting member x has the meanings stated above, with ammonia and a catalyst at a temperature ranging from 150.degree. to 300.degree. C. and under a pressure of from 50 to 300 bar, wherein the catalyst used is one whose catalytically active material consists of iron to an extent of from 5 to 100% w/w.
    Type: Grant
    Filed: April 22, 1992
    Date of Patent: February 22, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerhard Koppenhoefer, Wolfgang Schroeder, Dieter Voges
  • Patent number: 5288909
    Abstract: A process of reforming an alkyleneamine feedstock or a mixture of such feedstocks to an alkyleneamine or a mixture of alkyleneamines which is different from the feedstock or feedstock mixture. The process is catalyzed by one of the following: Group VB metal oxides, Group VB metal phosphates, Group IIA metal silicates, and tungsten oxides. For example, ethylenediamine is contacted with a catalyst of niobic acid or magnesium silicate to yield predominantly diethylenetriamine and non-cyclic triethylenetetramines; whereas high molecular weight polyethylenepolyamines are cracked by the same catalysts to mixtures of lower molecular weight linear and cyclic materials.
    Type: Grant
    Filed: August 19, 1992
    Date of Patent: February 22, 1994
    Assignee: The Dow Chemical Company
    Inventors: George E. Hartwell, Robert G. Bowman, David C. Molzahn
  • Patent number: 5214210
    Abstract: Phenolic compounds, particularly phenol, are aminated by reaction with ammonia in the presence of a catalyst made by calcining bayerite.
    Type: Grant
    Filed: September 5, 1991
    Date of Patent: May 25, 1993
    Assignee: Aristech Chemical Corporation
    Inventors: Alain A. Schutz, Leonard A. Cullo
  • Patent number: 5210306
    Abstract: This invention relates to a process for making amines by condensing an amino compound in the presence of a condensation catalyst and a condensation catalyst promoter, wherein said condensation catalyst promoter is present in an amount sufficient to promote the condensation catalyst. This invention also relates to an alkyleneamines producers composition rich in triethylenetetramine (TETA), tetraethylenepentamine (TEPA) and pentaethylenehexamine (PEHA).
    Type: Grant
    Filed: August 8, 1989
    Date of Patent: May 11, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Arthur R. Doumaux, Jr., David J. Schreck, Stephen W. King, George A. Skoler
  • Patent number: 5210307
    Abstract: A process for reforming alkyleneamines to predominantly linearly-extended polyalkylenepolyamines comprising contacting an alkyleneamine or mixture thereof with a catalyst under conditions such that a mixture of polyalkylenepolyamines enriched in linearly-extended products is formed, said catalyst containing at least one compound selected from the group consisting of (a) Group VB metal oxides, (b) Group VB metal phosphates, (c) silicates of Groups IIA, IIIB, IVB, VB, and the lanthanide and actinide metals, and (d) tungsten oxides, with the proviso that the silicates and tungsten oxides are essentially free of aluminum. For example, ethylenediamine is contacted with a catalyst of niobium phosphate or niobic acid under reaction conditions to yield predominantly non-cyclic polyethylenepolyamines.
    Type: Grant
    Filed: January 31, 1992
    Date of Patent: May 11, 1993
    Assignee: The Dow Chemical Company
    Inventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
  • 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: 5159115
    Abstract: Described are processes for the gas-phase mono N-alkylation of an aniline or an aminonaphthalene using a C.sub.1 to C.sub.5 aliphatic alcohol or ether over certain catalyst compositions based upon crystalline molecular sieves or amorphous silica-aluminas.
    Type: Grant
    Filed: August 18, 1989
    Date of Patent: October 27, 1992
    Assignee: Amoco Corporation
    Inventors: Peter G. Pappas, Judith B. Melville
  • Patent number: 5155271
    Abstract: The invention relates to a process for the preparation of compounds of the formula ##STR1## in which Q is substituted or unsubstituted C.sub.1 -C.sub.6 alkyl, A is a direct bond or a bridging member, s is the number 1 or 2, Z is a radical of the formula --CH.sub.2 CH.sub.2 OH, --CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 --Y, and Y is a leaving group, and the benzene or napthalene nucleus I can be further substituted, which comprises reacting compounds of the formula ##STR2## with compounds of the formulaQ--OH (3)in which A, s, Z and Q are as defined under formula (1), in the presence of hydrogenation catalysts, and then carrying out further conversion reactions where appropriate.The compounds obtained by the process according to the invention are suitable as intermediates for the preparation of reactive dyes.
    Type: Grant
    Filed: June 25, 1990
    Date of Patent: October 13, 1992
    Assignee: Ciba-Geigy Corporation
    Inventor: Peter Aeschlimann
  • Patent number: 5142052
    Abstract: Aryl- and heterocyclic-methanamines are prepared by reacting a hydroxy-aryl carbinol or a heterocyclic carbinol with a primary or a secondary amine in the presence of a cationic effect reagent.
    Type: Grant
    Filed: October 21, 1988
    Date of Patent: August 25, 1992
    Assignee: Laboratoires Syntex
    Inventors: Serge Beranger, Bruno Francois
  • Patent number: 5118851
    Abstract: A process of preparing a mixture of polyalkylenepolyamines and alkanolpolyamines comprising contacting a difunctional aliphatic alcohol with a primary or secondary aliphatic amine in the presence of a metal silicate catalyst wherein the metal is selected from the group consisting of Groups IIA, IIIB, and the lanthanide and actinide metals. For example, monoethanolamine reacts with diethylenetriamine in the presence of magnesium silicate to yield a mixture of higher molecular weight linear and branched polyethylenepolyamines and their corresponding alkanolpolyamines. These product mixtures are useful in the formation of specialty polyurethanes.
    Type: Grant
    Filed: December 5, 1990
    Date of Patent: June 2, 1992
    Inventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
  • Patent number: 5118850
    Abstract: A process for reforming alkyleneamines to predominantly linearly-extended polyalkylenepolyamines comprising contacting an alkyleneamine or mixture thereof with a catalyst under conditions such that a mixture of polyalkylenepolyamines enriched in linearly-extended products is formed, said catalyst containing at least one compound selected from the group consisting of (a) Group VB metal oxides, (b) Group VB metal phosphates, (c) silicates of Groups IIA, IIIB, IVB, VB, and the lanthanide and actinide metals, and (d) tungsten oxdies, with the proviso that the silicates and tungsten oxides are essentially free of aluminum. For example, ethylenediamine is contacted with a catalyst of niobium phosphate or niobic acid under reaction conditions to yield predominantly non-cyclic polyethylenepolyamines.
    Type: Grant
    Filed: November 9, 1990
    Date of Patent: June 2, 1992
    Assignee: The Dow Chemical Company
    Inventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
  • Patent number: 5117064
    Abstract: A method for synthesizing an aromatic amine, an aromatic alcohol or an aromatic thiol by an aromatic nucleophilic substitution reaction is disclosed, which comprises reacting a compound represented by formula (I): ##STR1## wherein Q.sup.1 represents an aromatic ring; EWG represents a group having a positive Hammett's .sigma..sub.p value; m represents an integer of 1 to 5; n represents an integer of 1 to 3; and X represents a group represented by formula (III): ##STR2## wherein R.sup.4 represents hydrogen atom, an aryl group or an alkyl group; Q.sup.2 represents an atomic group for forming an aromatic ring; and Z.sup.1 and Z.sup.2 each represents an oxygen atom or a sulfur atom with a nucleophilic reagent represented by formula (II):M--Y (II)wherein M represents a hydrogen atom, a metal atom or an ammonium; Y represents a --NHR.sup.1 group, an --OR.sup.1 group, or a --SR.sup.1 group; R.sup.1 represents a hydrogen atom, an alkyl group, an aryl group, a residue of a heterocyclic ring, a --NR.sup.2 R.sup.
    Type: Grant
    Filed: January 25, 1991
    Date of Patent: May 26, 1992
    Assignee: Fuji Photo Film Co., Ltd.
    Inventors: Takayuki Ito, Koki Nakamura