Of Ether Or Alkylene Oxide Patents (Class 564/399)
  • Patent number: 10766851
    Abstract: It is provided a method of converting a diaryl ether source such as lignin and/or polyphenylene oxide (PPO) containing 4-O-5 linkages and an inorganic chemical such as ammonia into an organic compound, comprising reacting said diaryl ether source with the inorganic chemical in presence of a catalyst, preferably palladium, transforming the 4-O-5 linkages of said diaryl ether source into the organic compound. It is provided a palladium-catalyzed synthesis of aniline derivatives from 4-O-5 linkage lignin model compounds and cheap industrial inorganic chemical ammonia via dual C(Ar)—O bond cleavage.
    Type: Grant
    Filed: August 22, 2019
    Date of Patent: September 8, 2020
    Assignee: THE ROYAL INSTITUTION FOR THE ADVANCEMENT OF LEARNING / MCGILL UNIVERSITY
    Inventors: Huiying Zeng, Chao-Jun Li, Dawei Cao
  • Patent number: 8859111
    Abstract: The present invention relates to 4,4?-substituted spirobifluorenes which are suitable, owing to excellent properties, as functional materials in organic electroluminescent devices. In addition, the present invention relates to a process for the preparation of 4,4?-substituted spirobifluorenes and to the use of these compounds in organic electroluminescent devices.
    Type: Grant
    Filed: June 18, 2010
    Date of Patent: October 14, 2014
    Assignee: Merck Patent GmbH
    Inventors: Amir Hossain Parham, Susanne Heun, Esther Breuning
  • Publication number: 20130178655
    Abstract: The invention relates to a method for synthesizing 3,5-dichloroanisole from 1,3,5-trichlorobenzene, which comprises: a) the reaction between 1,3,5-trichlorobenzene and a methanolate of an alkaline or alkaline-earth metal in a first solvent chosen from among dimethylsulfoxide and 1,1,3,3-tetramethylurea; b) the precipitation of the product resulting from step a) in a second solvent which is not included among substances considered carcinogenic, mutagenic and/or toxic for reproduction by Regulation (EC) n° 1272/2008 of the European Parliament and of the Council of 16 Dec. 2008; then c) the recovery of the precipitate thus obtained. Application: synthesis of 1,3,5-triamino-2,4,6-trinitrobenzene of which 3,5-dichloroanisole is an intermediate product.
    Type: Application
    Filed: January 12, 2011
    Publication date: July 11, 2013
    Applicant: Commissariat a l'energie atomique et aux energies alternatives
    Inventors: Eric Pasquinet, Anne Wuillaume, Didier Poullain, François Kosciusko-Morizet, Bénédicte Geneviève Jeanne Marie Treuille, Caroline Marie Catherine Kosciusko-Morizet, Nathalie Geneviève Marie Kosciusko-Morizet, Pierre Thaddée Jacques Hubert Kosciusko-Morizet
  • Publication number: 20120126179
    Abstract: The present invention relates to 4,4?-substituted spirobifluorenes which are suitable, owing to excellent properties, as functional materials in organic electroluminescent devices. In addition, the present invention relates to a process for the preparation of 4,4?-substituted spirobifluorenes and to the use of these compounds in organic electroluminescent devices.
    Type: Application
    Filed: June 18, 2010
    Publication date: May 24, 2012
    Applicant: Merck Patent GmbH
    Inventors: Amir Hossain Parham, Susanne Heun, Esther Breuning
  • Patent number: 8030521
    Abstract: Methods of producing TATB are disclosed. The method comprises providing acid wet TNPG and distilling water from the acid wet TNPG. The TNPG is reacted with an alkoxylating agent to form a solution of 1,3,5-trialkoxy-2,4,6-trinitrobenzene solution, which is reacted with an aminating agent. An alternate method comprises nitrating phloroglucinol in a first vessel to produce TNPG, which is reacted with an alkoxylating agent in a second vessel to form a solution comprising 1,3,5-trialkoxy-2,4,6-trinitrobenzene and at least one of at least one volatile byproduct and at least one nonvolatile byproduct. The at least one of at least one volatile byproduct and at least one nonvolatile byproduct is removed in situ. The 1,3,5-trialkoxy-2,4,6-trinitrobenzene is reacted with an aminating agent.
    Type: Grant
    Filed: May 7, 2007
    Date of Patent: October 4, 2011
    Assignee: Alliant Techsystems Inc.
    Inventors: Stephen P. Velarde, Vincent E. Mancini
  • Patent number: 7910776
    Abstract: Methods of producing 1,3,5-triamino-2,4,6-trinitrobenzene (TATB), from alkoxy derivatives of phloroglucinol, such as 5-methoxyresorcinol, 3,5-dimethoxyphenol, or 1,3,5-trimethoxybenzene, are disclosed. The alkoxy derivatives may be exposed to and directly nitrated with a reaction mixture comprising a sulfuric acid solution and at least one nitrate salt. The nitrated alkoxy derivative of phloroglucinol may be alkoxylated and, thereafter, aminated to produce the TATB.
    Type: Grant
    Filed: June 15, 2009
    Date of Patent: March 22, 2011
    Assignee: Alliant Techsystems Inc.
    Inventors: Nicholas A. Straessler, Stephen P. Velarde
  • Publication number: 20100298571
    Abstract: The invention relates to a method for preparing arylamines and, in particular, a method for preparing aniline and anilines substituted on the aromatic ring from ammonia, under easily-industrialised mild conditions with good selectivity and yields, in the presence of a catalytic system including a copper complex.
    Type: Application
    Filed: September 24, 2008
    Publication date: November 25, 2010
    Inventors: Marc Taillefer, Ning Xia
  • Patent number: 7763753
    Abstract: Methods of producing 1,3,5-triamino-2,4,6-trinitrobenzene are disclosed. One method comprises dissolving a 1,3,5-trialkoxy-2,4,6-trinitrobenzene compound in an organic solvent to form a 1,3,5-trialkoxy-2,4,6-trinitrobenzene compound solution. The 1,3,5-trialkoxy-2,4,6-trinitrobenzene compound solution is heated to a temperature of from approximately 30° C. to approximately 110° C. The 1,3,5-trialkoxy-2,4,6-trinitrobenzene compound is reacted with an aminating agent at a pressure of from approximately 30 pounds per square inch to approximately 120 pounds per square inch to produce a 1,3,5-triamino-2,4,6-trinitrobenzene solution.
    Type: Grant
    Filed: June 15, 2009
    Date of Patent: July 27, 2010
    Assignee: Alliant Techsystems Inc.
    Inventors: Alexander J. Paraskos, Michael P. Kramer
  • Patent number: 7482492
    Abstract: A process for forming a triarylamine compound includes reacting a halogenated aryl alcohol with an alcohol protecting agent and a first base to form a halogenated protected aryl alcohol compound, and reacting the halogenated protected aryl alcohol compound with an amine in the presence of a suitable catalyst and a second base.
    Type: Grant
    Filed: April 12, 2007
    Date of Patent: January 27, 2009
    Assignee: Xerox Corporation
    Inventors: Jennifer A. Coggan, Nan-Xing Hu
  • Patent number: 7453010
    Abstract: The invention relates to compounds of general formula (I): where R1 represents H or a (C1-C4)alkyl, —CO(C1-C4)alkyl, (C1-C4)alkylphenyl or —CO-phenyl group, said phenyl optionally being substituted; R2 represents H, a halogen atom, an —S(O)z(C1-C4)alkyl group, where z is equal to 0, 1 or 2, an —NHSO2(C1-C4)alkyl group, an —NHSO2-phenyl group or an —NHSO2—(C1-C4)alkylphenyl group, said phenyl optionally being substituted; R3 represents an —X—R4 group—in which X represents a bond, an oxygen atom or a —CH2— group and R4 represents H or a —CR5R6—COOR7 group, where R5, R6 and R7 independently represent H or a (C1-C4)alkyl group—a phenyl group optionally substituted or fused with a dioxolane group, a —CO—NR8R9 group—where R8 represents H, a (C1-C4)alkyl group or a (C1-C4)alkyl(C1-C4)alkoxy group and R9 represents a (C1-C4)alkyl(C1-C4)alkoxy group, a —(CH2)n-A group, where n is equal to 0, 1, 2, 3 or 4 and where A represents an indolyl group, a fluorenyl group or a phenyl group which is substituted, an optiona
    Type: Grant
    Filed: May 26, 2003
    Date of Patent: November 18, 2008
    Assignee: Sanofi Aventis
    Inventors: Philippe R. Bovy, Roberto Cecchi, Tiziano Croci, Olivier Venier
  • 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: 7115780
    Abstract: The invention concerns compounds of formula (I), wherein A is a group of formula (a) or (b), wherein: R represents a hydrogen or halogen atom, a —S(O)z(C1–C4)Alk wherein z is 0, 1 or 2, a —NHSO2(C1–C4)Alk, —SO2NH(C1–C4)Alk, —NHSO2—(C1–C4)Alk-phenyl or —NHSO2-phenyl group, said phenyl capable of bearing a halogen atom, a (C1–C4)Alk group or a (C1–C6)alkoxy group; R1 represents a hydrogen atom or a —(C1–C4)Alk, —CO(C1–C4)Alk, —(C1–C4)Alk-phenyl or —CO-phenyl group, said phenyl capable of bearing a halogen atom or a —(C1–C4)Alk or (C1–C6)alkoxy group; R2 is a hydrogen atom, a —SO2(C1–C4)Alk, —SO2—(C1–C4)Alk-phenyl, —SO2-phenyl group, or a —(C1–C4)Alk group; X completes a saturated or unsaturated cycle of 5 to 8 atoms, capable of bearing one or two —(C1–C4)Alk groups and/or two carbonyl groups; R3 and R?3 represent each independently a hydrogen or halogen atom, a —(C1–C6)Alk, hydroxy, —CN, —(C1–C6)alkoxy, —COR4 or Y—CR8R9—COR4 group; Y represents O or CH2; R4 represents a hydroxy, (C1–C6)alkoxy or —NR5R6 group; R
    Type: Grant
    Filed: December 2, 2002
    Date of Patent: October 3, 2006
    Assignee: Sanofi-Aventis
    Inventors: Laura Barzaghi, Roberto Cecchi, Nunzia Viviani
  • Patent number: 6723880
    Abstract: A process for producing secondary amines of the formula R1R2N—A—NH—A—NR1R2, where R1 and R2 are linear or branched C1-20-alkyl radicals, optionally substituted with from 1 to 5 phenyl groups; or cyclohexyl radicals; or together with the nitrogen atom to which they are bound, form a 3 to 7 membered saturated ring, optionally containing further hetero atoms selected from the group consisting of N, O and S, and optionally substituted with from 1 to 5 C1-2-alkyl groups. The group A is a linear or branched C2-20-alkylene group, optionally containing from 1 to 5 phenylene groups; or a radical of the formula —CH(R3)—[CH2]k—X—[CH(R3)—[CH2]k—X]m—CH(R3)—[CH2]k—, where R3 is H or CH3, X is O, S or NR4, R4 is H or a linear or branched C1-4-alkyl group, k is 1 or 2, and m is an integer from 0 to 4; or a group of the formula where n, o, p, and q are, independently, integers from 1 to 4.
    Type: Grant
    Filed: June 19, 2002
    Date of Patent: April 20, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Neumann, Johann-Peter Melder, Christoph Benisch, Arthur Höhn, Joachim Pfeffinger
  • 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: 6563003
    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: October 16, 2002
    Date of Patent: May 13, 2003
    Assignee: Pharmacia & Upjohn Company
    Inventor: Bruce Allen Pearlman
  • 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: 6222073
    Abstract: Process for the preparation of an N-arylethylaniline of the formula (I) Ar—N(R1)2-n(CHR2CHR3Ar′)n  (I) by reacting an aromatic olefin of the formula (II) Ar′CR3=CHR2  (II) with an aniline of the formula (III) Ar—N(R1)2-n(H)n  (III) in an inert solvent in the presence of at least one basic catalyst selected from the group consisting of alkali metal alcoholates and alkaline earth metal alcoholates or alkali metal amides and alkaline earth metal amides, where, in the formulae (I) to (III), Ar and Ar′, independently of one another, are an aryl radical selected from the group consisting of the fused and nonfused C6-C22-aromatics and of the fused or nonfused C5-C22heteroaromatics which have at least one nitrogen, oxygen or sulfur atom in the ring; R1, R2 and R3, independently of one another, are a hydrogen atom, a C1-C8-alkyl radical or an aryl radical Ar; and n is the number 1 or 2.
    Type: Grant
    Filed: July 3, 2000
    Date of Patent: April 24, 2001
    Assignee: Aventis Research & Technologies GmbH & Co. KG
    Inventors: Jürgen Herwig, Matthias Beller, Claudia Breindl, Harald Trauthwein, Elisabeth Eichberger, Anton Eichberger
  • Patent number: 6162944
    Abstract: Process for production of, from inexpensive raw materials of high commercial availability, N-cyclopropylanilines which are an important intermediate in producing a quinolonecarboxylic acid having a cyclopropyl group at the 1-position, a fluorine atom at the 6-position, and an alkyl group, an alkoxy group or a fluorine-substituted methoxy group at the 8-position (this quinolonecarboxylic acid is a useful synthetic antibacterial agent); and intermediates therefor. For example, a process for producing an N-cyclopropyl-3,4-difluoroaniline represented by the formula (4): ##STR1## includes reacting, in the presence of an acid in an alcohol type solvent, a 3,4-difluoro-2-substituted-aniline with a 1-alkoxy-1-trialkylsilyloxycyclopropane to produce an N-alkoxycyclopropylaniline represented by the general formula (3): ##STR2## and then reducing the N-alkoxycyclopropylaniline.
    Type: Grant
    Filed: November 22, 1999
    Date of Patent: December 19, 2000
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Yasuo Yoshida, Kazuto Umezu, Yusuke Hamada, Fumiya Tabuchi
  • Patent number: 6127537
    Abstract: A method for the preparation of 3-amino-1,2-propandiol derivatives of the formula (I) ##STR1## by reacting a compound of the formula (II) ##STR2## with RNH.sub.2, wherein R and R.sub.1 have the same meaning as given in the description. The formula (I) derivatives are .beta.-blockers used for treating hypertension.
    Type: Grant
    Filed: December 10, 1999
    Date of Patent: October 3, 2000
    Assignee: Everlight USA, Inc.
    Inventors: Biing-Jiun Uang, Jia-Wen Chang
  • 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: 6090984
    Abstract: New .alpha.-phenoxy-alkanols represented by the general formula ##STR1## in which R.sup.1 and R.sub.2, which may be identical or different, represent a hydrogen atom or the CH.sub.3 radical, and their stereoisomers of R,S conformation when they contain at least one asymmetric carbon.
    Type: Grant
    Filed: July 2, 1998
    Date of Patent: July 18, 2000
    Assignee: CFPI Agro
    Inventors: Joseph Schapira, Jean-Claude Cheminaud, Jean-Jacques Gasse, Vincent Schanen, Benoit Rondot, Jean-Claude Lemoine
  • Patent number: 6060625
    Abstract: A process for the alkoxylation of a polyetheramine to form an etheramine alkoxylate. In the process, a polyetheramine is reacted with an alkylene oxide in the presence of an alcohol to form the etheramine alkoxylate. The alcohol serves as a catalyst to allow the reaction proceed at a heightened temperature as compared to the reaction in the absence of alcohol, while at the same time limiting the amount of glycol by-product production which would otherwise typically form when higher polyetheramines are to be alkoxylated. The alcohol may be, for instance, ethanol or methanol.
    Type: Grant
    Filed: April 30, 1999
    Date of Patent: May 9, 2000
    Assignee: Huntsman Petrochemical Corporation
    Inventors: Wei-Yang Su, Mike W. McKinney, Timothy L. Lambert, Edward T. Marquis
  • Patent number: 6046359
    Abstract: A catalyst comprises, based on the total weight of the catalyst,0.1-6% by weight of cobalt, nickel or a mixture thereof,0.001-25% by weight of ruthenium,0-10% by weight of copper and0-5% by weight of promoterson a porous metal oxide carrier.It preferably comprises 0.1-3% by weight of cobalt and 0.1-3% by weight of nickel. It can be used in hydrogenation reactions, dehydrogenation reactions or hydrogenation/dehydrogenation reactions, in particular in the amination of alkylene oxides, alcohols, aldehydes or ketones with ammonia or primary or secondary amines.
    Type: Grant
    Filed: March 4, 1999
    Date of Patent: April 4, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Joachim Wulff-Doring, Johann-Peter Melder, Gerhard Schulz, Guido Voit, Gutshoven Frank, Wolfgang Harder
  • Patent number: 6028226
    Abstract: Preparation process for 3,4-disubstituted dinitroanilines of formula ##STR1## in which, R.sub.1 and R.sub.2, which are identical to or different from one another, represent a hydrogen atom, a C.sub.1 to C.sub.6 saturated, linear or branched alkyl radical, a C.sub.2 to C.sub.6 linear or branched alkylene radical, a cyclopropyl radical or a chloroethyl radical,R.sub.3 and R.sub.4, which are identical to or different from one another are chosen from the group containing the chlorine atom, the amino group, the C.sub.1 to C.sub.3 lower alkyl radicals and the trifluoromethyl radical,comprising successively a dinitration stage of a 3,4-disubstituted phenol, an alkylation stage of the dinitrated derivative thus obtained and an amination stage of the 3,4-disubstituted 2,6-dinitro-alkoxybenzene thus obtained.
    Type: Grant
    Filed: April 7, 1998
    Date of Patent: February 22, 2000
    Assignee: Cfpi Agro
    Inventors: Joseph Schapira, Jean-Claude Cheminaud, Jean-Jacques Gasse, Vincent Schanen, Benoit Rondot, Jean-Claude Lemoine
  • Patent number: 5986137
    Abstract: A process and reagent for allylating a nucleophile preferably of formula (V).(R).sub.n Ar--Y--H (V)The nucleophile is reacted with a reagent containing an allyl derivative and a catalyst in an aqueous phase containing at least lone element of group VIII of the Classification of the elements. A water-soluble phosphine may also be present in the reagent, and the reagent may also contain at least one organic phase.
    Type: Grant
    Filed: June 12, 1998
    Date of Patent: November 16, 1999
    Assignee: Rhodia Chimie
    Inventors: Jean-Michel Grosselin, Hubert Kempf, Jean-Pierre LeCouve
  • Patent number: 5981800
    Abstract: Preparation process for 4-substituted dinitroanilines of formula ##STR1## in which R.sub.1 is chosen from the group containing the tert-butyl, sulphonamido, trifluoromethyl, methyl-sulphonyl and isopropyl radicals,R.sub.2 and R.sub.3, which are identical to or different from one another, represent a hydrogen atom, a linear or branched alkyl, cycloalkyl, haloalkyl or alkenyl radical containing less than 6 carbon atoms, characterized in that that it comprises successively:a dinitration stage of the 4-substituted phenol corresponding to the sought 4-substituted dinitro-aniline, this dinitration stage being carried out in a reaction medium containing a slight excess of nitrating agent, a sufficient quantity of protons and a catalyst chosen from the group containing the soluble salts of the transition metals of columns IV to XII of the Periodic Table, preferably the soluble salts of Fe.sub.III, Fe.sub.II, Zn.sub.II and Cu.sub.
    Type: Grant
    Filed: April 7, 1998
    Date of Patent: November 9, 1999
    Assignee: CFPI Agro
    Inventors: Joseph Schapira, Jean-Claude Cheminaud, Jean-Jacques Gasse, Vincent Schanen, Benoit Rondot, Jean-Claude Lemoine
  • 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: 5902900
    Abstract: An (S)-1-phenyl-2-substituted propane derivative shown by the following formula (I) ##STR1## wherein R.sup.1 and R.sup.2 represent a lower alkyl group, etc., or R.sup.1 and R.sup.2 may form together an alkylene group, etc.; R.sup.3, R.sup.4 and R.sup.5 represent a hydrogen atom, etc.; and X represents a hydroxyl group which may be protected with a protective group, or a halogen atom etc., can readily be produced (i) by permitting a microorganism belonging to the genus Torulaspora, the genus Candida, the genus Pichia or the like to act on a phenylacetone derivative and asymmetrically reducing the compound, or (ii) by sterically inverting an (R)-enantiomer. (R,R)-1-phenyl-2-?(2-phenyl-1-methylethyl)amino!ethanol derivative having a high optical purity can easily be obtained from the compound of the formula (I). The ethanol derivative is useful as an anti-obesity agent and the like.
    Type: Grant
    Filed: June 27, 1997
    Date of Patent: May 11, 1999
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Michio Ito, Noritsugu Yamasaki, Yoshinori Kobayashi, Kiyoshi Ikura
  • Patent number: 5895824
    Abstract: In a process for preparing polyether polyols containing aromatics by molecular addition of alkylene oxides to H-functional initiators at from 70.degree. C. to 135.degree. C. and pressures of from 0.1 MPa to 1.0 MPa, the alkoxylation is carried out using at least one initiator comprising at least 95% by weight of 2,3 and 3,4 isomers of tolylenediamine, from 0.5 to 4% by weight of 2,4 and 2,6 isomers of tolylenediamine and from 0.1 to 1.5% by weight of more volatile fractions from tolylenediamine production. The polyether polyols prepared by this process can be used as component of a polyol mixture for producing rigid polyurethane foams.
    Type: Grant
    Filed: June 7, 1996
    Date of Patent: April 20, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Stefan Dinsch, Regina Pretzsch, Juergen Winkler, Bernd Guettes, Karl-Heinz Steinchen
  • Patent number: 5840981
    Abstract: A process for preparing N-methyl-2-(3,4-dimethoxyphenyl)-ethylamine comprises hydrogenating 3,4-dimethoxyphenylacetonitrile with a methylamine of the general formula I ##STR1## where R.sup.1 is hydrogen, benzyl or tert-butyl, and hydrogen in the presence of a supported catalyst which comprises from 0.05 to 50% by weight of copper chromite, copper, silver, gold, iron, cobalt, nickel, ruthenium, rhodium, palladium, osmium, iridium, platinum or mixtures thereof, in the presence or absence of water at from 20.degree. to 200.degree. C. under from 1 to 300 bar.
    Type: Grant
    Filed: October 28, 1997
    Date of Patent: November 24, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Eberhard Fuchs, Horst Zimmermann, Tom Witzel, Boris Breitscheidel, Rainer Becker, Horst Nauhauser
  • 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: 5786405
    Abstract: Clear, amine-initiated polyether polyols are made by epoxidizing an amine in the presence of an alkali metal hydroxide catalyst. After the desired degree of epoxidation has been achieved, a hydroxy-carboxylic acid is added to the epoxidized mixture in an amount sufficient to neutralize any remaining alkali metal hydroxide. The polyols produced in this manner are particularly useful for the production of polyurethane and apolyisocyanurate foams.
    Type: Grant
    Filed: November 1, 1996
    Date of Patent: July 28, 1998
    Assignee: Bayer Corporation
    Inventors: Steven L. Schilling, Herman P. Doerge, Lotar H. Hanusa
  • Patent number: 5777168
    Abstract: This invention relates to a process for producing N-alkyl-dinitroalkylaniline and particularly N-sec-butyl-4-tert-butyl-2,6-dinitroaniline by methylation of an alkylphenol followed by a one or two stage dinitration of the resulting alkylanisole which is followed by reaction with an amine.
    Type: Grant
    Filed: June 3, 1997
    Date of Patent: July 7, 1998
    Assignee: SRM Chemical, Ltd. Co.
    Inventors: Stefan Kwiatkowski, Krzysztof Pupek, Brenda L. Lawrence, Lowell J. Lawrence
  • Patent number: 5763667
    Abstract: Ether-linked amine-terminated polyethers are produced by reacting (1) a polyether polyol in which substantially all of the hydroxyl groups have been replaced with good leaving groups with (2) an aminoalcohol and/or aminothiol and (3) a deprotonating agent. The aminopolyethers obtained by this process are characterized by low viscosities and excellent reactivities over a wide range of molecular weights and functionalities.
    Type: Grant
    Filed: January 31, 1996
    Date of Patent: June 9, 1998
    Assignee: Bayer Corporation
    Inventors: Rick L. Adkins, William E. Slack
  • Patent number: 5731463
    Abstract: The present invention relates to a process for the selective alkylation of intermediates of betaxolol.
    Type: Grant
    Filed: September 23, 1996
    Date of Patent: March 24, 1998
    Assignee: Abbott Laboratories
    Inventors: Xiu C. Wang, Ashok V. Bhatia, Steven Chamberlin, Luping Liu
  • Patent number: 5723670
    Abstract: Amines which are solid at ambient temperature and pressure are liquified by reacting those amines with a derivatizing agent represented by the formula XY in which X represents a halide or sulfonate group and Y represents an alkyl group, a cycloalkyl group, an alkoxyalkyl group or an aryl group. The amine and derivatizing agent are reacted at temperatures of from about 50.degree. to about 250.degree. C. in amounts such that the molar ratio of derivatizing agent to amine groups is from about 0.25:1 to 8:1.
    Type: Grant
    Filed: June 18, 1996
    Date of Patent: March 3, 1998
    Assignee: Bayer Corporation
    Inventors: Rick L. Adkins, William E. Slack
  • Patent number: 5693864
    Abstract: Disclosed herein is a process for preparing an amine terminated polyether comprising reacting a polyether containing a leaving group with a primary amine or ammonia at a temperature of about 70 to 250 degrees Centigrade.
    Type: Grant
    Filed: October 7, 1992
    Date of Patent: December 2, 1997
    Assignee: Bayer Corporation
    Inventors: William E. Slack, Rick L. Adkins, Hans Georg Schmelzer
  • Patent number: 5689006
    Abstract: This invention relates to a process for producing N-alkyl-dinitroalkylaniline and particularly N-sec-butyl-4-tert-butyl-2,6-dinitroaniline by methylation of an alkylphenol followed by nitration of the resulting alkylanisole which is followed by reaction with an amine.
    Type: Grant
    Filed: June 29, 1995
    Date of Patent: November 18, 1997
    Assignee: SRM Chemical, Ltd. Co.
    Inventors: Stefan Kwiatkowski, Krzysztof Pupek, Brenda L. Lawrence, Lowell J. Lawrence
  • Patent number: 5663441
    Abstract: This invention relates to a process for producing mono- and di- N-alkyl-dinitroalkylaniline or dinitroaniline derivative and particularly N-sec-butyl-4-tert-butyl-2,6-dinitroaniline by methylation of an alkylphenol or phenol derivative followed by nitration of the resulting acetic acid alkylanisole or anisole derivative which is followed by reaction with an amine. Acetic acid by-product produced during nitration is recycled by converting back to acetic anhydride.
    Type: Grant
    Filed: March 22, 1996
    Date of Patent: September 2, 1997
    Assignee: SRM Chemical, Ltd. Co.
    Inventors: Stefan Kwiatkowski, Krzysztof Pupek, Brenda L. Lawrence, Lowell J. Lawrence
  • Patent number: 5616811
    Abstract: Etheramine alkoxylates are described which have the formula: ##STR1## where R.sup.1 is a straight or branched alkyl, aryl or alkylaryl group of 6 to 22 carbon atoms; R.sup.3 are independently hydrogen or C.sub.1 to C.sub.3 alkyl; m averages from about 1 to about 20; and x and y each independently average from about 0 to 30, where x+y averages from about 2 to about 60. These etheramine alkoxylates have surfactant properties. Further, they may be quaternized to make other compounds which will have useful surfactant properties.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: April 1, 1997
    Assignee: Huntsman Petrochemical Corporation
    Inventors: Jeffrey J. Vipond, John M. Larkin, Terry L. Renken, Howard M. Stridde
  • Patent number: 5602283
    Abstract: A multistage process of preparing N-alkyl-3,4-dialkyl-2,6-dinitroanilines starts from 3,4-dialkyl phenol and goes through the stages of 3,4-dialkyl-2,6-dinitrophenol and 3,4-dialkyl-2,6-ditro alkoxybenzene, wherein the latter are new compounds.
    Type: Grant
    Filed: May 23, 1995
    Date of Patent: February 11, 1997
    Assignee: Agan Chemical Manufacturers Ltd.
    Inventor: Morris Sarel
  • Patent number: 5550292
    Abstract: A benzylamine derivative or salt thereof having antidepressant and antianxiety activities having the general formula: ##STR1## wherein R.sup.1 is a lower alkyl group;R.sup.2 is a cycloalkyl group; andR.sup.3 is a halogen atom;or salt thereof.
    Type: Grant
    Filed: April 29, 1995
    Date of Patent: August 27, 1996
    Assignee: Otsuka Pharmaceutical Co., Ltd.
    Inventors: Yohji Sakurai, Nobuyuki Kurahashi, Tsuyoshi Hirose, Takashi Miwa, Atsushi Mori, Takao Nishi
  • Patent number: 5510535
    Abstract: Ether-linked amine-terminated polyethers are produced by reacting (1) a polyether polyol in which substantially all of the hydroxyl groups have been replaced with good leaving groups with (2) an aminoalcohol and/or aminothiol and (3) a deprotonating agent. The aminopolyethers obtained by this process are characterized by low viscosities and excellent reactivities over a wide range of molecular weights and functionalities.
    Type: Grant
    Filed: November 22, 1994
    Date of Patent: April 23, 1996
    Assignee: Bayer Corporation
    Inventors: Rick L. Adkins, William E. Slack
  • Patent number: 5475148
    Abstract: The intermediate ##STR1## wherein R is a lower alkyl group, is used to prepare a N-alkyl-3,4-dialkyl-2,6,-dinitro-aniline in a relatively simple, inexpensive and safe fashion, and with a high yield.
    Type: Grant
    Filed: June 23, 1994
    Date of Patent: December 12, 1995
    Assignee: Agan Chemical Manufacturers Ltd.
    Inventor: Morris Sarel
  • Patent number: 5466871
    Abstract: A process for preparing a nitroaniline derivative comprising a step of reacting an aromatic nitro compound with an O-alkylhydroxylamine or a salt thereof in the presence of a base and optionally a metallic catalyst, which process is industrially advantageous since it provides the nitroaniline derivative from the aromatic nitro compound in a high yield in one step, and the aminating agent used can be obtained from hydroxylamine at a relatively low cost.
    Type: Grant
    Filed: July 11, 1994
    Date of Patent: November 14, 1995
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Shinzo Seko
  • Patent number: 5434308
    Abstract: A method of dehydrogenating 3-amino-2-cyclohexene-1-one with a supported palladium or palladium-platinum catalyst in a solvent in the presence of base to produce 3-aminophenol and its use directly without purification to produce 3,4'-oxydianiline.
    Type: Grant
    Filed: January 18, 1994
    Date of Patent: July 18, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Stephen E. Jacobson
  • Patent number: 5420353
    Abstract: A regioselective process is disclosed for synthesis of 1R-amino-2S-indanol or 1S-amino-2R-indanol, wherein the stereochemical integrity of the carbon-oxygen bond at C-2 in the indene oxide starting material is retained.
    Type: Grant
    Filed: March 11, 1994
    Date of Patent: May 30, 1995
    Assignee: Merck & Co., Inc.
    Inventors: Thomas R. Verhoeven, F. Edward Roberts, Christ H. Senanayake, Kenneth M. Ryan
  • Patent number: 5344986
    Abstract: Compounds of the formula: ##STR1## wherein: n=0 or 1;R.sub.1 and R.sub.2 are C.sub.1 to C.sub.3 alkyl groups, or R.sub.2 may be H when n=0; and Y is selected from the group: ##STR2## wherein: m=1-6Z=SO.sub.2, S, C=O, CH.sub.2 or C(CH.sub.3).sub.2 ; and a process for their preparation are described.
    Type: Grant
    Filed: March 7, 1991
    Date of Patent: September 6, 1994
    Assignee: Bromine Compounds, Ltd.
    Inventors: Jakob Oren, Joshua Hermolin, David Feldman, Michael Zviely, Dov Zamir, Hugo Keselman
  • 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: 5300559
    Abstract: Polyamines endowed with chain extension activity for formulations such as polyureas and polyurethanes are disclosed, which have the general formula: ##STR1## wherein n is 0-1000; R.sub.1 =R.sub.2, and R.sub.1 and R.sub.2 are from the group --CH.sub.2 --CH.sub.2 --; --CH.sub.2 --C(CH.sub.3)H--; and --C(CH.sub.3)H--CH.sub.2 --; and R.sub.3 and R.sub.4 are each independently selected from the group consisting of H, --CH.sub.3, --CH.sub.2 CH.sub.3, --CH.sub.2 OH, and --CH.sub.2 --CH.sub.2 --OH.
    Type: Grant
    Filed: May 28, 1993
    Date of Patent: April 5, 1994
    Assignee: Hoechst Celanese Corporation
    Inventors: Michael T. Sheehan, James R. Sounik