Of Carbonyl Containing Compound Patents (Class 564/396)
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Patent number: 12037303Abstract: A method for preparing a diaryl-p-phenylenediamine compound of Formula I comprises the steps of reacting a compound of Formula II and a compound of Formula III in a condensation dehydrogenation reaction in the presence of a solvent, a hydrogen acceptor, a water-carrying agent, and a catalyst; wherein R1, R2 and R3 are independently selected and each is H, a C1-C8 alkyl, a C3-C8 cycloalkyl, a C1-C8 alkoxy, a C3-C8 cycloalkoxy, or phenyl; a and c are independently selected and each is an integer of 0 to 5, and b is an integer of 0 to 4:Type: GrantFiled: December 29, 2022Date of Patent: July 16, 2024Assignee: Sennics Co., Ltd.Inventors: Jinguo Xing, Xiangyun Guo, Zhimin Tang
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Patent number: 8809591Abstract: The present invention is directed to a process for the manufacture of 2,3,5-trimethyl-hydro-p-benzoquinone comprising the following steps: a) hydrogenating 2,6-dimethyl-p-benzoquinone with hydrogen in the presence of a hydrogenation catalyst in an organic solvent to obtain 2,6-dimethyl-hydro-p-benzoquinone; b) reacting 2,6-dimethyl-hydro-p-benzoquinone with a secondary amine and formal-dehyde in an organic solvent to obtain 2,6-dimethyl-3-(N,N-disubstituted aminomethyl)-hydro-p-benzoquinone; c) reacting 2,6-dimethyl-3-(N,N-disubstituted aminomethyl)-hydro-p-benzoquinone with hydrogen in the presence of a hydrogenolysis catalyst in an organic solvent to obtain 2,3,5-trimethylhydro-p-benzoquinone; wherein the organic solvent in all steps a), b) and c) is independently selected from the group consisting of methyl tert.-butyl ether, ethyl tert.-butyl ether, methyl tert.-amyl ether, methoxycyclopentane and any mixtures thereof. Preferably the organic solvent used in all steps a), b) and c) is the same.Type: GrantFiled: August 25, 2011Date of Patent: August 19, 2014Assignee: DSM IP Assets B.V.Inventors: Werner Bonrath, Thomas Netscher, Jan Schütz, Bettina Wüstenberg
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Patent number: 8592631Abstract: A process for synthesizing 2-methoxymethyl-1,4-benzenediamine, its derivatives of formula (IV) and the salts thereof, which comprises a reductive amination step. The preferred final product is 2-methoxymethyl-1,4-benzenediamine of formula (IV-a). These compounds may be used as primary intermediates in compositions for dyeing keratin fibers.Type: GrantFiled: January 28, 2011Date of Patent: November 26, 2013Assignee: The Procter & Gamble CompanyInventors: John Michael Gardlik, Garry Steven Garrett, Bryan Patrick Murphy, John Michael Janusz, John August Wos
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Publication number: 20130211080Abstract: The present invention is directed to a process for the manufacture of 2,3,5-trimethyl-hydro-p-benzoquinone comprising the following steps: a) hydrogenating 2,6-dimethyl-p-benzoquinone with hydrogen in the presence of a hydrogenation catalyst in an organic solvent to obtain 2,6-dimethyl-hydro-p-benzoquinone; b) reacting 2,6-dimethyl-hydro-p-benzoquinone with a secondary amine and formal-dehyde in an organic solvent to obtain 2,6-dimethyl-3-(N,N-disubstituted aminomethyl)-hydro-p-benzoquinone; c) reacting 2,6-dimethyl-3-(N,N-disubstituted aminomethyl)-hydro-p-benzoquinone with hydrogen in the presence of a hydrogenolysis catalyst in an organic solvent to obtain 2,3,5-trimethylhydro-p-benzoquinone; wherein the organic solvent in all steps a), b) and c) is independently selected from the group consisting of methyl tert.-butyl ether, ethyl tert.-butyl ether, tert.-amyl ether, methoxycyclopentane and any mixtures thereof. Preferably the organic solvent used in all steps a), b) and c) is the same.Type: ApplicationFiled: August 25, 2011Publication date: August 15, 2013Applicant: DSM IP ASSETS B.V.Inventors: Werner Bonrath, Thomas Netscher, Jan Schütz, Bettina Wüstenberg
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Publication number: 20130030073Abstract: Amine-initiated polyether polyols are made by reacting an amine adduct with a triglyceride in the presence of an alkylene oxide to obtain a polyol having a total renewables content of at least 20%.Type: ApplicationFiled: July 26, 2011Publication date: January 31, 2013Applicant: Bayer MaterialScience LLCInventors: Don S. Wardius, Steven L. Schilling
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Patent number: 7737302Abstract: This invention described a synthesis method of bupropion hydrochloride. m-chloropropiophenone was brominated directly with bromine, then aminated with t-butylamine and finally reacted with HCl to obtain crude product of bupropion hydrochloride. Pure product was obtained after recrystallization. This method is convenient and suitable for commercial manufacturing because of low cost of production, high yield, less byproducts and being environmental friendly.Type: GrantFiled: July 7, 2008Date of Patent: June 15, 2010Assignee: Zhejiang Apeloa Medical Technology Co., Ltd.Inventors: Chaogang Wu, Huayou Xiang, Xianghua Yu, Chun He, Fengying Li, Xianghong Shi, Chengyue Lu, Guoliang Chen, Yangxiang Ge
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Patent number: 7709679Abstract: The invention provides a process for the simultaneous preparation of 4,4?-diphenylmethanediamine and also diphenylmethane diisocyanate and polyphenylenepolymethylene polyisocyanates, which comprises the steps a) preparation of a mixture of diphenylmethanediamine and polyphenylenepolymethylenepolyamines by acid condensation of aniline and formaldehyde and subsequent work-up of the mixture, b) splitting-off of part of the mixture prepared in step a), c) distillation of the mixture separated off in step b) in a column, d) recirculation of the bottom product from step c) to the end product from step a) and condensation of the overhead product from step c), e) distillation of the overhead product from step c) in a column, f) recirculation of the overhead product from step e) to the end product from step a), g) isolation of the 4,4?-diphenylmethanediamine obtained as bottom product in step e), h) reaction of the mixture from step a) with phosgene and subsequent work-up of the reaction product.Type: GrantFiled: January 12, 2007Date of Patent: May 4, 2010Assignee: BASF AktiengesellschaftInventors: Michael Bock, Hans-Juergen Pallasch, Filip Deberdt, Johnny Moors
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Patent number: 7538251Abstract: Severely sterically hindered secondary aminoether alcohols are prepared by a process comprising reacting a ketene with sulfuric acid to produce an anhydride which is then reacted with, to cleave the ring of, a dioxane to yield a cleavage product which is then aminated using an amine, followed by hydrolysis with a base to yield the desired severely sterically hindered secondary aminoether alcohol.Type: GrantFiled: February 1, 2005Date of Patent: May 26, 2009Assignee: ExxonMobil Research and Engineering CompanyInventors: Michael Siskin, Alan Roy Katritzky, Kostyantyn Mykolayevich Kirichenko, Adeana Richelle Bishop, Christine Nicole Elia
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Patent number: 7524990Abstract: Severely sterically hindered secondary aminoether alcohols are prepared by reacting organic carboxylic, organic carboxylic acid halides, acid anhydrides or a ketene with an alkyl, alkaryl or alkylhalo sulfonate to yield a sulfonic-carboxylic anhydride compound which is then reacted with a dioxane to cleave the ring of the dioxane, yielding a cleavage product which cleavage product is then aminated with an alkylamine and hydrolyzed with base to yield the severely sterically hindered secondary aminoether alcohol.Type: GrantFiled: February 1, 2005Date of Patent: April 28, 2009Assignee: ExxonMobil Research and Engineering CompanyInventors: Michael Siskin, Alan Roy Katritzky, Kostyantyn Mykolayevich Kirichenko, Adeana Richelle Bishop, Christine Nicole Elia
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Publication number: 20080315155Abstract: This invention provides compositions which comprise at least one aromatic secondary diamine having a Gardner color number no more than about 6. The aromatic secondary diamine either is in the form of one benzene ring having two secondary amino groups on the ring, or is in the form of two benzene rings connected by an alkylene bridge and having one secondary amino group on each ring. At least one N,N?-dihydrocarbylhydroxylamine is optionally present in the composition. Processes for producing such compositions are also provided.Type: ApplicationFiled: December 21, 2006Publication date: December 25, 2008Applicant: ALBEMARLE CORPORATIONInventors: John Y. Lee, David W. Owens, Richard D. Glass, Paul L. Wiggins
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Patent number: 7361789Abstract: The present invention relates to novel dihydronaphthalene compounds, compositions, methods for using the same, and processes for preparing the same. The present invention also relates to novel total synthesis approaches for preparing these compounds. In addition, the present invention relates to methods of producing quantities of isomers of these compounds and separating and purifying them using chiral separation techniques. The present invention also relates to methods of producing quantities of a single isometric compound without the need for chiral separation techniques.Type: GrantFiled: July 27, 2005Date of Patent: April 22, 2008Assignee: Amgen Inc.Inventors: Qi Yan, Carlos Orihuela, Bo Shen, Ying Chen, Xin Wang, John Ng, Ruizhi Ji, Pengzu Zhou
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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: 7186864Abstract: A compound of Formula (IA) or Formula (IB) wherein R1, R2, R3, R4, R5, R6, R7, and R8 are as defined herein, or a tautomer, prodrug, solvate, or salt thereof; pharmaceutical compositions containing such compounds, and methods of modulating the glucocorticoid receptor function and methods of treating disease-states or conditions mediated by the glucocorticoid receptor function or characterized by inflammatory, allergic, or proliferative processes in a patient using these compounds.Type: GrantFiled: May 28, 2003Date of Patent: March 6, 2007Assignee: Boehringer Ingelheim Pharmaceuticals, Inc.Inventors: Thomas Martin Kirrane, Jr., Daniel Kuzmich, John Robert Proudfoot, David Thomson
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Patent number: 7164043Abstract: A conjugate addition reaction between an ?,?-unsaturated ketone compound and a carbamate compound is carried out to synthesize a ?-aminoketone, a salt or a hydrate salt of a transition metal of Groups 7 to 11 of the Periodic Table of Elements being present in the reaction system as the catalyst. The novel method and the catalyst are capable of synthesizing the ?-aminoketone by the Aza-Michael reaction with high yield and efficiency.Type: GrantFiled: March 7, 2003Date of Patent: January 16, 2007Assignee: Japan Science and Technology AgencyInventors: Shu Kobayashi, Masaharu Sugiura
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Patent number: 6888029Abstract: The present invention relates to a process for the preparation of N-aryl amine and N-aryl amide compounds. Generally, the process of the present invention involves reacting a compound having a primary or secondary amino or amido group with an arylating compound, in the presence of a weak base and a transition metal catalyst, under reaction conditions effective to form an N-aryl amine or N-aryl amide compound, the transition metal catalyst comprising a Group 8 metal, e.g., Ni, Pd, or Pt, and at least one carbene-containing ligand. Typically, the transition metal catalyst is formed in a preceding step from the conjugate acid form of the carbene ligand, a stoichiometric amount of a strong base, and a Group 8 metal atom or ion.Type: GrantFiled: January 22, 2003Date of Patent: May 3, 2005Assignee: Massachusetts Institute of TechnologyInventors: Stephen L. Buchwald, Joseph M. Fox
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Patent number: 6642420Abstract: A process for the preparation of aldehydes and/or alcohols or amines by reacting olefins in the liquid phase with carbon monoxide and hydrogen, a part of these gases being dispersed in the form of gas bubbles in the reaction liquid and another part being dissolved in the reaction liquid, in the presence or absence of a primary or secondary amine and in the presence of a cobalt carbonyl, rhodium carbonyl, palladium carbonyl or ruthenium carbonyl complex dissolved homogeneously in the reaction liquid and having a phosphorus-, arsenic-, antimony- or nitrogen-containing ligand, at elevated temperatures and at 1 to 100 bar, wherein the reaction is carried out in a vertically arranged, tubular reactor comprising a reactor body and at least one circulation line, a part of the reaction liquid is fed continuously via the circulation line to at least one nozzle which is mounted in the upper part of the reactor body and is coordinated with a guide member, open at the top and bottom and bounded by parallel walls, in theType: GrantFiled: February 7, 2001Date of Patent: November 4, 2003Assignee: BASF AktiengesellschaftInventors: Peter Zehner, Armin Ulonska, Rocco Paciello
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Patent number: 6620776Abstract: A novel composition having the formula: wherein R1 is selected from the group consisting of an alkyl group containing from 1 to 20 carbon atoms and an aryl group, and R2 is selected from the group consisting of an alkyl group containing from 1 to 20 carbon atoms and an aryl group. The composition is made by combining an amine compound, a carbonyl compound, a solvent, and a sulfur-containing compound. The composition is used as a detergent additive in cleaning process.Type: GrantFiled: June 19, 2002Date of Patent: September 16, 2003Assignee: Phillips Petroleum CompanyInventors: Mitchell D. Refvik, David W. Dockter
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Patent number: 6506721Abstract: A novel composition having the formula: wherein R1 is selected from the group consisting of an alkyl group containing from 1 to 20 carbon atoms and an aryl group, and R2 is selected from the group consisting of an alkyl group containing from 1 to 20 carbon atoms and an aryl group. The composition is made by combining an amine compound, a carbonyl compound, a solvent, and a sulfur-containing compound. The composition is used as a detergent additive in cleaning process.Type: GrantFiled: September 22, 2000Date of Patent: January 14, 2003Assignee: Phillips Petroleum CompanyInventors: Mitchell D. Refvik, David W. Dockter
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Patent number: 6479697Abstract: A process for the preparation of &agr;-(2,4-disulfophenyl)-N-tert-butylnitrone diacids and pharmaceutically acceptable salts thereof by the reaction of the corresponding disulfophenyl aldehyde with N-tert-butylhydroxylammonium acetate is disclosed.Type: GrantFiled: April 5, 2001Date of Patent: November 12, 2002Assignee: AstraZeneca ABInventors: Henry Kruk, John McGinley, Sergei Pouhov, John Vajda, Jörgen Blixt
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Patent number: 6409773Abstract: Couplers for hair coloring compositions for oxidative dyeing of hair are compounds of the formula at least one coupler comprising a compound of the formula (1): wherein R is selected from of C1 to C2 alkyl and hydroxyethyl, R1 and R2 are each independently selected from the group consisting of C1 to C5 alkyl, C3 to C6 cycloalkyl, C1 to C5 alkoxy, C1 to C5 hydroxyalkyl, C1 to C5 hydroxyalkoxy, or R1 and R2 together with the carbon atom to which they are attached form a C3 to C6 cycloalkyl group.Type: GrantFiled: December 14, 2000Date of Patent: June 25, 2002Assignee: Clairol IncorporatedInventors: Mu-Ill Lim, Yuh-Guo Pan, Margaret Popp
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Publication number: 20020016507Abstract: Process for the preparation of azine and of hydrazine by bringing ammonia, hydrogen peroxide and a reactant carrying a carbonyl group into contact with a working solution, comprising:Type: ApplicationFiled: April 5, 2001Publication date: February 7, 2002Inventors: Georges Brenguer, Remi Jullin, Jean-Philippe Ricard
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Publication number: 20010003136Abstract: Amines are prepared by reacting aldehydes or ketones at elevated temperature under elevated pressure with nitrogen compounds selected from the group of ammonia, primary and secondary amines, and with hydrogen in the presence of a catalyst, wherein the catalytically active mass of the catalyst contains, after its preparation and before the treatment with hydrogen, 22 to 45% by weight of oxygen-containing compounds of zirconium, calculated as ZrO2,Type: ApplicationFiled: December 5, 2000Publication date: June 7, 2001Inventors: Jan Nouwen, Arthur Hohn, Horst Neuhauser, Frank Funke, Stephan Andreas Schunk, Johann-Peter Melder, Knut Eger, Michael Hesse, Joachim Wulff-Doring
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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: 6072085Abstract: The method of the present invention provides a simple general route to a wide range of secondary amines.Type: GrantFiled: September 30, 1997Date of Patent: June 6, 2000Assignee: Massachusetts Institute of TechnologyInventors: Xavier Verdaguer, Udo E. W. Lange, Stephen L. Buchwald
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Patent number: 5885538Abstract: The present invention provides a method and composition regeneration of an aminal that has previously been reacted with a sulfide selected from hydrogen sulfide and mercaptans. The method includes contacting a scavenging mixture which includes an aminal, and an oxidation catalyst with a gas such as air, oxygen enriched air, oxygen, ozone enriched air and ozone. The composition includes an aminal, and an oxidation catalyst. The method and composition are useful for the regeneration of an aminal base sulfur scavenging compound.Type: GrantFiled: July 2, 1997Date of Patent: March 23, 1999Assignee: Quaker Chemical CorporationInventors: Edward A. Trauffer, Muge Caglar
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Patent number: 5861535Abstract: Tertiary aminoaryl compounds, such as N,N'dialkylaminoaryl compounds, are prepared using successive reductive steps without isolation therebetween, at high temperature and pressure. A nitroaryl compound is reduced using a ketone as both solvent and reactant in a reductive environment, and the resulting intermediate is further reacted with an aldehyde in the same reaction mixture without isolation to provide the second substituent on the amino group.Type: GrantFiled: September 23, 1997Date of Patent: January 19, 1999Assignee: Eastman Kodak CompanyInventor: Victor L. Mylroie
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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: 5773656Abstract: Known (R)-1-aryl-alkylamines of the formula ##STR1## in whichR.sup.1 and Ar have the meanings indicated in the description, are prepared by a new process, which comprisesa) reacting a racemate of an ethyl or methyl 2-aryl-alkanoate of the formula ##STR2## with ammonia in the presence of a lipase which is suitable for the cleavage of esters, in the presence of a diluent,b) separating off from the reaction mixture the resulting (R)-2-aryl-alkanamide of the formula ##STR3## and then reacting it with sodium hypochlorite or sodium hypobromite in the presence of water.Type: GrantFiled: August 9, 1996Date of Patent: June 30, 1998Assignee: Bayer AktiengesellschaftInventor: Uwe Stelzer
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Patent number: 5739374Abstract: 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: GrantFiled: February 14, 1997Date of Patent: April 14, 1998Assignee: BASF AktiengesellschaftInventors: Bernd Janssen, Hans-Heiner Wuest
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Patent number: 5665756Abstract: Novel aminoalkyloximes of the formula ##STR1## wherein: a. X is hydrogen, loweralkyl, loweralkoxy, halogen, trifluoromethyl, or a group of the formula ##STR2## wherein Y is hydrogen or loweralkyl, and p is 1 or 2; b. A is a group of the formula ##STR3## c. R.sup.1 and R.sup.2 are independently hydrogen or lowerakyl; and d. m is 2 to 6 and n is 0, or 2 to 6, inclusive, serotonin reuptake inhibitors, useful for treating depression and obsessive compulsive disorders are described. Also described are precursors of and processes for the preparation of such aminoakyloximes.Type: GrantFiled: August 3, 1994Date of Patent: September 9, 1997Assignee: Hoechst Marion Roussel, Inc.Inventors: Gregory M. Shutske, Brian S. Freed, John D. Tomer, IV, R. Richard L. Hamer
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Patent number: 5616799Abstract: A process for the preparation of glycoloylanilide of the formula (G) ##STR1## is recited that involves reacting a nitrobenzene with hydrogen and, if desired, with a carbonyl compound, in the presence of a noble metal catalyst and a solvent, reacting the compound produced with chloroacetyl chloride, reacting the resulting product with a benzyl alcohol and with a base, or reacting the resulting compound with an O-benzylglycoloyl chloride, and debenzylating the resulting benzylglycoloylanilide product by reacting with hydrogen in the presence of a noble metal catalyst. The invention also relates to a process for the preparation of O-benzylglycoloylanilide.Type: GrantFiled: April 17, 1995Date of Patent: April 1, 1997Assignee: Hoechst AktiengesellschaftInventors: Siegfried Planker, Theodor Papenfuhs
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Patent number: 5536878Abstract: Disclosed are (1) a method for preparing an aromatic secondary amino compound which comprises reacting an N-cyclohexylideneamino compound in the presence of a hydrogen moving catalyst and a hydrogen acceptor by the use of a sulfur-free polar solvent and/or a cocatalyst, and (2) a method for preparing an aromatic secondary amino compound which comprises reacting cyclohexanone or a nucleus-substituted cyclohexanone, an amine and a nitro compound corresponding to the amine in a sulfur-free polar solvent in the presence of a hydrogen moving catalyst, a cocatalyst being added or not added. In a further aspect, a method is provided for the preparation of aminodiphenylamine by reacting phenylenediamine and cyclohexanone in the presence of a hydrogen transfer catalyst in a sulfur-free polar solvent while using nitroaniline as a hydrogen acceptor.Type: GrantFiled: December 2, 1994Date of Patent: July 16, 1996Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Teruyuki Nagata, Chiyuki Kusuda, Masaru Wada, Kenichi Satou, Masae Uchida
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Patent number: 5436371Abstract: A process for preparing p-nitroaromatic amides is provided which comprises contacting a nitrile, nitrobenzene, a suitable base and water in the presence of a suitable solvent system to form a mixture, and reacting the mixture at a suitable temperature in a confined reaction zone in the presence of a controlled amount of protic material. The p-nitroaromatic amides of the invention can be reduced to p-aminoaromatic amides. In one embodiment, the p-aminoaromatic amide is further reacted with ammonia under conditions which produce the corresponding p-aminoaromatic amine and the amide corresponding to the nitrile starting material or with water in the presence of a suitable basic or acidic catalyst under conditions which produce the corresponding p-aminoaromatic amine and the acid or salt thereof corresponding to the nitrile starting material. In another embodiment, the p-aminoaromatic amine is reductively alkylated to produce alkylated p-aminoaromatic amine.Type: GrantFiled: August 29, 1994Date of Patent: July 25, 1995Assignee: Monsanto CompanyInventors: Michael K. Stern, Brian K. Cheng
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Patent number: 5395971Abstract: A process for making unsaturated .alpha.-amines from olefins wherein the process includes adding an aminating agent, an olefin and a molybdenum based catalyst to a reaction vessel having a nitrogen atmosphere. The catalyst may be described by the general formula LL'MoO.sub.2, L.sub.2 L'MoO.sub.2, or LL'MoO(X--Y).Type: GrantFiled: March 11, 1994Date of Patent: March 7, 1995Assignee: The Board of Regents of The University of OklahomaInventors: Kenneth M. Nicholas, Anurag S. Srivastava
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Patent number: 5382690Abstract: Disclosed are(1) a method for preparing an aromatic secondary amino compound which comprises reacting an N-cyclohexylideneamino compound in the presence of a hydrogen moving catalyst and a hydrogen acceptor by the use of a sulfur-free polar solvent and/or a cocatalyst, and(2) a method for preparing an aromatic secondary amino compound which comprises reacting cyclohexanone or a nucleus-substituted cyclohexanone, an amine and a nitro compound corresponding to the amine in a sulfur-free polar solvent in the presence of a hydrogen moving catalyst, a cocatalyst being added or not added.Type: GrantFiled: August 2, 1993Date of Patent: January 17, 1995Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Teruyuki Nagata, Chiyuki Kusuda, Masaru Wada, Kenichi Satou
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Patent number: 5371289Abstract: The present invention relates to a process for the preparation of a N-substituted-N'-phenyl-p-phenylenediamine of the formula: ##STR1## comprising reacting (a) a mixture of (1) N-phenyl-p-quinoneimine of the formula: ##STR2## and (2) p-hydroxydiphenylamine in a mole ratio of N-phenyl-p-quinoneimine to p-hydroxydiphenylamine of from 1.5:1 to 1:1.5 with (b) a primary amine of the formula:R.sup.1 --NH.sub.2in the presence of methanol wherein R.sup.1 is selected from the group of radicals consisting of alkyls having 1 to 20 carbon atoms, cycloalkyls having 6 to 8 carbon atoms and radicals of the structural formula: ##STR3## wherein R.sup.2 may be the same or different and is independently selected from the group of radicals consisting of hydrogen and an alkyl having 1 carbon atom, R.sup.3 is selected from the group of radicals consisting of an alkyl having 1 to 12 carbon atoms and n is an integer of from 0 to 6.Type: GrantFiled: March 22, 1993Date of Patent: December 6, 1994Assignee: The Goodyear Tire & Rubber CompanyInventors: Kirkwood S. Cottman, Joseph A. Kuczkowski
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Patent number: 5349109Abstract: A process for making unsaturated .alpha.-amines from olefins wherein the process includes adding an aminating agent, an olefin and a molybdenum based catalyst to a reaction vessel having a nitrogen atmosphere. The catalyst may be described by the general formula LL'MoO.sub.2, L.sub.2 L'MoO.sub.2, or LL'MoO(X-Y).Type: GrantFiled: August 26, 1993Date of Patent: September 20, 1994Assignee: The Board of Regents of the University of OklahomaInventors: Kenneth M. Nicholas, Anurag S. Srivastava
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Patent number: 5344987Abstract: Optionally substituted diphenylamines can be obtained by reacting optionally substituted anilines with optionally substituted cyclohexanones over a supported catalyst at 200.degree.-450.degree. C. and 0.1-20 bar, the supported catalyst containing one or more metals having a dehydrogenating action selected from the group Ru, Pd, Os, Ir, Pt, Fe, Co, Ni, Re, Mn, Cu, Ag, Cr and Ce.Type: GrantFiled: July 16, 1993Date of Patent: September 6, 1994Assignee: Bayer AktiengesellschaftInventors: Otto Immel, Gerhard Darsow, Hans-Josef Buysch
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Patent number: 5344983Abstract: Process for preparing a pentane-1,5-diamine of the formula ##STR1## where R.sup.1 represents a variety of organic radicals including alkyl which can bear substituents such as hydroxyl, halogen, alkoxy, carbalkoxy, carboxyl, alkylamino, cycloalkyl or aryl, andR.sup.2 and R.sup.3 independently of one another, represent hydrogen or have the same meanings as R.sup.1 or together are a C.sub.4 -C.sub.7 -alkylene chain which is unsubstituted or substituted by one to five C.sub.1 -C.sub.4 -alkyl groups,which comprises:(a) reacting a .gamma.-cyanoketone of the formula ##STR2## where R.sup.1, R.sup.2 and R.sup.3 have the meanings given above, with excess ammonia in a first reaction space on an acidic heterogeneous catalyst at 20.degree.-150.degree. C. and 15-500 bar, and(b) hydrogenating the resulting reaction product in a second separate reaction space in the presence of excess ammonia on a cobalt, nickel or noble metal catalyst at 50.degree.-180.degree. C. and 30-500 bar.Type: GrantFiled: August 26, 1992Date of Patent: September 6, 1994Assignee: BASF AktiengesellschaftInventors: Tom Witzel, Eberhard Fuchs, Franz Merger, Claus-Ulrich Priester
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Patent number: 5276193Abstract: A process for preparing an N-alkyl-substituted aminophenol is disclosed, comprising continuously feeding an aldehyde or a ketone to a reaction system containing an organic solvent, a catalyst for reduction, hydrogen, and an aminophenol to conduct a reductive alkylation reaction, wherein said reductive alkylation reaction is carried out while continuously adding an organic carboxylic acid into the reaction system. The process attains a high yield even when the catalyst is repeatedly used and does not cause corrosion of equipment.Type: GrantFiled: August 1, 1990Date of Patent: January 4, 1994Assignee: Sumitomo Chemical Co., Ltd.Inventors: Hiroshi Maki, Michihiro Kawasaki, Hiroshi Shimizu, Yoshiaki Ito
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Patent number: 5231217Abstract: The present invention is directed to a novel solvent-free process for preparing amine terminated compounds by reacting a polyfunctional acetoacetic acid ester with either ammonia or an organic compound which contains one or more primary amino groups in the presence of an acidic catalyst selected from the group consisting of (i) boron trifluoride etherate and (ii) organic acids having pKa values of from 0.1 to 0.8.Type: GrantFiled: March 20, 1991Date of Patent: July 27, 1993Assignee: Miles Inc.Inventors: Robert P. Yeater, Robson Mafoti, Josef Sanders
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Patent number: 5221770Abstract: A process is disclosed for the preparation of 2-amino-5,6-dimethoxy-tetralin, which is a useful intermediate for the preparation of pharmacologically active chemical compounds.Type: GrantFiled: September 25, 1992Date of Patent: June 22, 1993Assignee: Zambon Group S.p.A.Inventors: Giorgio Bertolini, Cesare Casagrande, Francesco Santangelo
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Patent number: 5202485Abstract: 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: GrantFiled: April 29, 1991Date of Patent: April 13, 1993Assignee: Sumitomo Chemical Co., Ltd.Inventors: Hiroshi Maki, Michihiro Kawasaki, Horishi Shimizu, Yoshiaki Ito
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Patent number: 5066824Abstract: The present invention is directed to a process for preparing amine terminated compounds by reacting a polyfunctional acetoacetic acid ester with either ammonia or an organic compound which contains one or more primary amino groups in the presence of a solvent and an acidic catalyst selected from the group consisting of (i) boron trifuloride etherate and (ii) organic acids having pKa values of from 0.1 to 0.8 with the proviso that if the primary amino group containing compound contains no aromatically bound amino groups, the pKa of said organic acid is from 0.1 to less than 0.7.Type: GrantFiled: August 3, 1990Date of Patent: November 19, 1991Assignee: Mobay CorporationInventors: Robson Mafoti, Josef Sanders
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Patent number: 5053540Abstract: The present invention relates to a process for the preparation of a p-aminodiphenylamine comprising reacting N-phenylquinoneimine of the formula: ##STR1## with ammonia, ammonium hydroxide or mixtures thereof, wherein the molar ratio of N-phenylquinoneimine to NH.sub.3 in the reaction mixture ranges from about 1:1 to 1:80.Type: GrantFiled: March 8, 1990Date of Patent: October 1, 1991Assignee: The Goodyear Tire & Rubber CompanyInventor: Kirkwood S. Cottman
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Patent number: 4774359Abstract: The synthesis and characterization of several polyenamine ketones are discussed wherein conjugated diacetylenic diketones and aromatic diamines are used as a route to the formation of high molecular weight polyenamine ketones which exhibit good mechanical properties and can be cast into creasible films. Typical polymerization conditions involved the reaction of stoichiometric amounts of 1,4- or 1,3-PPPO and a diamine at 60.degree.-130.degree. C. in m-cresol at (w/w) solids content of 8-26% for a specified period of time under a nitrogen atmosphere. Novel polyenamine ketones were prepared with inherent viscosities as high as 1.99 dl/g and tough, clear amber films with tensile strengths of 12,400 psi and tensile moduli of 397,000 psi were cast from solutions of the polymers in chloroform. The polymers exhibited T.sub.g s as high as 235.degree. C. and weight losses of 14% after aging at 232.degree. C. in circulating air for sixty hours.Type: GrantFiled: January 5, 1987Date of Patent: September 27, 1988Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventors: Paul M. Hergenrother, Robert G. Bass, Mark S. Sinsky, John W. Connell
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Patent number: 4730075Abstract: A process for the production of (1) an ether or (2) a second amine comprises reacting an activated olefin with respectively an alcohol or first amine in the presence of a catalyst which is either (a) an amidine or (b) a Lewis base and epoxide. The same catalyst may also be used to carry out the reverse reaction in which an activated olefin and an alcohol or first amine are produced from the appropriate ether or second amine.Type: GrantFiled: June 20, 1986Date of Patent: March 8, 1988Assignee: BP Chemicals LimitedInventor: Michael J. Green
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Patent number: 4663483Abstract: The synthesis and characterization of several polyenamine ketones are discussed wherein conjugated diacetylenic diketones and aromatic diamines are used as a route to the formation of high molecular weight polyenamine ketones which exhibit good mechanical properties and can be cast into creasible films. Typical polymerization conditions involved the reaction of stoichiometric amounts of 1,4- or 1,3-PPPO and a diamine at 60.degree.-130.degree. C. in m-cresol at (w/w) solids content of 8-26% for a specified period of time under a nitrogen atmosphere. Novel polyenamine ketones were prepared with inherent viscosities as high as 1.99 dl/g and tough, clear amber films with tensile strengths of 12,400 psi and tensile moduli of 397,000 psi were cast from solutions of the polymers in chloroform. The polymers exhibited T.sub.g s as high as 235.degree. C. and weight losses of 14% after aging at 232.degree. C. in circulating air for sixty hours.Type: GrantFiled: May 15, 1985Date of Patent: May 5, 1987Assignee: The United States of America as represented by the Administrator of the National Aeronautics and Space AdministrationInventors: Paul M. Hergenrother, Robert G. Bass, Mark S. Sinsky, John W. Connell
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Patent number: 4621158Abstract: A method for making amines by reacting alcohols and/or aldehydes with primary and/or secondary amines or with ammonia in the presence of a catalyst at elevated temperature, and optionally at elevated pressure, in the liquid phase, the catalyst being an unsupported catalyst consisting of a combination of copper and tin compounds.Type: GrantFiled: August 21, 1985Date of Patent: November 4, 1986Assignee: Schering AktiengesellschaftInventors: Hans-Juergen Hubert, Klaus D. Tillmetz
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Patent number: 4506039Abstract: Polymer-containing polyether polyamines containing terminal aromatically-bound amino groups are produced by in situ polymerization of a polyether polyamine with an olefinically unsaturated monomer. The polyether polyamine starting material must have terminal aromatic amino groups, a molecular weight of from 800 to 10,000 and an aromatic amino group content of from 0.3 to 16 wt. %. Suitable olefinically unsaturated monomers include .alpha.,.beta.-unsaturated nitriles, aromatic vinyl compounds, .alpha.,.beta.-unsaturated carboxylic acids and esters thereof, vinyl esters, vinyl halides, vinylidene halides, .alpha.,.beta.-unsaturated carboxylic acid amides and aminoalkyl esters of unsaturated carboxylic acids. Acrylonitrile/styrene mixtures are preferred monomers. The starting materials are employed in quantities such that the product modified polyether polyamine contains from 1 to 60 wt. % polymer or graft-polymer. The product polyamines are particularly useful in the production of polyurethanes.Type: GrantFiled: December 20, 1982Date of Patent: March 19, 1985Assignee: Bayer AktiengesellschaftInventors: Gerhard Balle, Werner Rasshofer, Winfried Schoberth