Of Ether Or Alkylene Oxide Patents (Class 564/399)
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Patent number: 10766851Abstract: 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: GrantFiled: August 22, 2019Date of Patent: September 8, 2020Assignee: THE ROYAL INSTITUTION FOR THE ADVANCEMENT OF LEARNING / MCGILL UNIVERSITYInventors: Huiying Zeng, Chao-Jun Li, Dawei Cao
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Patent number: 8859111Abstract: 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: GrantFiled: June 18, 2010Date of Patent: October 14, 2014Assignee: Merck Patent GmbHInventors: Amir Hossain Parham, Susanne Heun, Esther Breuning
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Publication number: 20130178655Abstract: 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: ApplicationFiled: January 12, 2011Publication date: July 11, 2013Applicant: Commissariat a l'energie atomique et aux energies alternativesInventors: 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
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Publication number: 20120126179Abstract: 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: ApplicationFiled: June 18, 2010Publication date: May 24, 2012Applicant: Merck Patent GmbHInventors: Amir Hossain Parham, Susanne Heun, Esther Breuning
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Patent number: 8030521Abstract: 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: GrantFiled: May 7, 2007Date of Patent: October 4, 2011Assignee: Alliant Techsystems Inc.Inventors: Stephen P. Velarde, Vincent E. Mancini
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Patent number: 7910776Abstract: 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: GrantFiled: June 15, 2009Date of Patent: March 22, 2011Assignee: Alliant Techsystems Inc.Inventors: Nicholas A. Straessler, Stephen P. Velarde
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Publication number: 20100298571Abstract: 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: ApplicationFiled: September 24, 2008Publication date: November 25, 2010Inventors: Marc Taillefer, Ning Xia
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Patent number: 7763753Abstract: 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: GrantFiled: June 15, 2009Date of Patent: July 27, 2010Assignee: Alliant Techsystems Inc.Inventors: Alexander J. Paraskos, Michael P. Kramer
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Patent number: 7482492Abstract: 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: GrantFiled: April 12, 2007Date of Patent: January 27, 2009Assignee: Xerox CorporationInventors: Jennifer A. Coggan, Nan-Xing Hu
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Patent number: 7453010Abstract: 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 optionaType: GrantFiled: May 26, 2003Date of Patent: November 18, 2008Assignee: Sanofi AventisInventors: Philippe R. Bovy, Roberto Cecchi, Tiziano Croci, Olivier Venier
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Patent number: 7355077Abstract: A process for preparing tolterodine with high purity.Type: GrantFiled: October 26, 2005Date of Patent: April 8, 2008Assignees: 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
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Patent number: 7115780Abstract: 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; RType: GrantFiled: December 2, 2002Date of Patent: October 3, 2006Assignee: Sanofi-AventisInventors: Laura Barzaghi, Roberto Cecchi, Nunzia Viviani
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Patent number: 6723880Abstract: 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: GrantFiled: June 19, 2002Date of Patent: April 20, 2004Assignee: BASF AktiengesellschaftInventors: Peter Neumann, Johann-Peter Melder, Christoph Benisch, Arthur Höhn, Joachim Pfeffinger
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Patent number: 6613944Abstract: 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: GrantFiled: January 28, 2003Date of Patent: September 2, 2003Assignee: Pharmacia & Upjohn CompanyInventor: Bruce Allen Pearlman
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Patent number: 6563003Abstract: 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: GrantFiled: October 16, 2002Date of Patent: May 13, 2003Assignee: Pharmacia & Upjohn CompanyInventor: Bruce Allen Pearlman
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Patent number: 6403834Abstract: 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: GrantFiled: July 23, 2001Date of Patent: June 11, 2002Assignee: Rhodia ChimieInventors: Michel Alas, Albert Bouniot
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Patent number: 6222073Abstract: 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: GrantFiled: July 3, 2000Date of Patent: April 24, 2001Assignee: Aventis Research & Technologies GmbH & Co. KGInventors: Jürgen Herwig, Matthias Beller, Claudia Breindl, Harald Trauthwein, Elisabeth Eichberger, Anton Eichberger
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Patent number: 6162944Abstract: 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: GrantFiled: November 22, 1999Date of Patent: December 19, 2000Assignee: Ihara Chemical Industry Co., Ltd.Inventors: Yasuo Yoshida, Kazuto Umezu, Yusuke Hamada, Fumiya Tabuchi
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Patent number: 6127537Abstract: 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: GrantFiled: December 10, 1999Date of Patent: October 3, 2000Assignee: Everlight USA, Inc.Inventors: Biing-Jiun Uang, Jia-Wen Chang
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Patent number: 6100430Abstract: 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: GrantFiled: September 10, 1998Date of Patent: August 8, 2000Assignee: Daicel Chemical Industries, Ltd.Inventors: Kenichi Yamamoto, Kazuyuki Matsuoka, Hiroshi Yagihara
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Patent number: 6090984Abstract: 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: GrantFiled: July 2, 1998Date of Patent: July 18, 2000Assignee: CFPI AgroInventors: Joseph Schapira, Jean-Claude Cheminaud, Jean-Jacques Gasse, Vincent Schanen, Benoit Rondot, Jean-Claude Lemoine
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Patent number: 6060625Abstract: 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: GrantFiled: April 30, 1999Date of Patent: May 9, 2000Assignee: Huntsman Petrochemical CorporationInventors: Wei-Yang Su, Mike W. McKinney, Timothy L. Lambert, Edward T. Marquis
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Patent number: 6046359Abstract: 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: GrantFiled: March 4, 1999Date of Patent: April 4, 2000Assignee: BASF AktiengesellschaftInventors: Joachim Wulff-Doring, Johann-Peter Melder, Gerhard Schulz, Guido Voit, Gutshoven Frank, Wolfgang Harder
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Patent number: 6028226Abstract: 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: GrantFiled: April 7, 1998Date of Patent: February 22, 2000Assignee: Cfpi AgroInventors: Joseph Schapira, Jean-Claude Cheminaud, Jean-Jacques Gasse, Vincent Schanen, Benoit Rondot, Jean-Claude Lemoine
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Patent number: 5986137Abstract: 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: GrantFiled: June 12, 1998Date of Patent: November 16, 1999Assignee: Rhodia ChimieInventors: Jean-Michel Grosselin, Hubert Kempf, Jean-Pierre LeCouve
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Patent number: 5981800Abstract: 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: GrantFiled: April 7, 1998Date of Patent: November 9, 1999Assignee: CFPI AgroInventors: Joseph Schapira, Jean-Claude Cheminaud, Jean-Jacques Gasse, Vincent Schanen, Benoit Rondot, Jean-Claude Lemoine
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Patent number: 5925789Abstract: 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: GrantFiled: April 6, 1998Date of Patent: July 20, 1999Assignee: DuPont Pharmaceuticals CompanyInventors: Michael E. Pierce, Cheng Y. Chen, Anusuya Choudhury, Lilian A. Radesca, Lushi Tan, Dalian Zhao
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Patent number: 5902900Abstract: 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: GrantFiled: June 27, 1997Date of Patent: May 11, 1999Assignee: Daicel Chemical Industries, Ltd.Inventors: Michio Ito, Noritsugu Yamasaki, Yoshinori Kobayashi, Kiyoshi Ikura
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Patent number: 5895824Abstract: 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: GrantFiled: June 7, 1996Date of Patent: April 20, 1999Assignee: BASF AktiengesellschaftInventors: Stefan Dinsch, Regina Pretzsch, Juergen Winkler, Bernd Guettes, Karl-Heinz Steinchen
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Patent number: 5840981Abstract: 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: GrantFiled: October 28, 1997Date of Patent: November 24, 1998Assignee: BASF AktiengesellschaftInventors: Eberhard Fuchs, Horst Zimmermann, Tom Witzel, Boris Breitscheidel, Rainer Becker, Horst Nauhauser
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Patent number: 5817877Abstract: 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: GrantFiled: September 19, 1997Date of Patent: October 6, 1998Assignee: Yale UniversityInventors: John F. Hartwig, Michael S. Driver, Janis Louie, Blake Hamann
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Patent number: 5786405Abstract: 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: GrantFiled: November 1, 1996Date of Patent: July 28, 1998Assignee: Bayer CorporationInventors: Steven L. Schilling, Herman P. Doerge, Lotar H. Hanusa
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Patent number: 5777168Abstract: 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: GrantFiled: June 3, 1997Date of Patent: July 7, 1998Assignee: SRM Chemical, Ltd. Co.Inventors: Stefan Kwiatkowski, Krzysztof Pupek, Brenda L. Lawrence, Lowell J. Lawrence
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Patent number: 5763667Abstract: 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: GrantFiled: January 31, 1996Date of Patent: June 9, 1998Assignee: Bayer CorporationInventors: Rick L. Adkins, William E. Slack
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Patent number: 5731463Abstract: The present invention relates to a process for the selective alkylation of intermediates of betaxolol.Type: GrantFiled: September 23, 1996Date of Patent: March 24, 1998Assignee: Abbott LaboratoriesInventors: Xiu C. Wang, Ashok V. Bhatia, Steven Chamberlin, Luping Liu
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Patent number: 5723670Abstract: 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: GrantFiled: June 18, 1996Date of Patent: March 3, 1998Assignee: Bayer CorporationInventors: Rick L. Adkins, William E. Slack
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Patent number: 5693864Abstract: 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: GrantFiled: October 7, 1992Date of Patent: December 2, 1997Assignee: Bayer CorporationInventors: William E. Slack, Rick L. Adkins, Hans Georg Schmelzer
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Patent number: 5689006Abstract: 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: GrantFiled: June 29, 1995Date of Patent: November 18, 1997Assignee: SRM Chemical, Ltd. Co.Inventors: Stefan Kwiatkowski, Krzysztof Pupek, Brenda L. Lawrence, Lowell J. Lawrence
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Patent number: 5663441Abstract: 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: GrantFiled: March 22, 1996Date of Patent: September 2, 1997Assignee: SRM Chemical, Ltd. Co.Inventors: Stefan Kwiatkowski, Krzysztof Pupek, Brenda L. Lawrence, Lowell J. Lawrence
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Patent number: 5616811Abstract: 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: GrantFiled: June 6, 1995Date of Patent: April 1, 1997Assignee: Huntsman Petrochemical CorporationInventors: Jeffrey J. Vipond, John M. Larkin, Terry L. Renken, Howard M. Stridde
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Patent number: 5602283Abstract: 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: GrantFiled: May 23, 1995Date of Patent: February 11, 1997Assignee: Agan Chemical Manufacturers Ltd.Inventor: Morris Sarel
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Patent number: 5550292Abstract: 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: GrantFiled: April 29, 1995Date of Patent: August 27, 1996Assignee: Otsuka Pharmaceutical Co., Ltd.Inventors: Yohji Sakurai, Nobuyuki Kurahashi, Tsuyoshi Hirose, Takashi Miwa, Atsushi Mori, Takao Nishi
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Patent number: 5510535Abstract: 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: GrantFiled: November 22, 1994Date of Patent: April 23, 1996Assignee: Bayer CorporationInventors: Rick L. Adkins, William E. Slack
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Patent number: 5475148Abstract: 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: GrantFiled: June 23, 1994Date of Patent: December 12, 1995Assignee: Agan Chemical Manufacturers Ltd.Inventor: Morris Sarel
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Patent number: 5466871Abstract: 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: GrantFiled: July 11, 1994Date of Patent: November 14, 1995Assignee: Sumitomo Chemical Company, LimitedInventor: Shinzo Seko
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Patent number: 5434308Abstract: 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: GrantFiled: January 18, 1994Date of Patent: July 18, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventor: Stephen E. Jacobson
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Patent number: 5420353Abstract: 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: GrantFiled: March 11, 1994Date of Patent: May 30, 1995Assignee: Merck & Co., Inc.Inventors: Thomas R. Verhoeven, F. Edward Roberts, Christ H. Senanayake, Kenneth M. Ryan
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Patent number: 5344984Abstract: 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: GrantFiled: April 8, 1993Date of Patent: September 6, 1994Assignee: Texaco Chemical CompanyInventors: John F. Knifton, Carter G. Naylor
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Patent number: 5344986Abstract: 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: GrantFiled: March 7, 1991Date of Patent: September 6, 1994Assignee: Bromine Compounds, Ltd.Inventors: Jakob Oren, Joshua Hermolin, David Feldman, Michael Zviely, Dov Zamir, Hugo Keselman
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Patent number: 5300559Abstract: 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: GrantFiled: May 28, 1993Date of Patent: April 5, 1994Assignee: Hoechst Celanese CorporationInventors: Michael T. Sheehan, James R. Sounik