Preparing Directly By Ring Alkylation Or Dealkylaton Patents (Class 564/409)
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Patent number: 11858873Abstract: Disclosed is a method for continuously synthesizing a propellane compound. The method includes the following steps: using 1,1-dibromo-2,2-bis(chloromethyl)cyclopropane or a derivative thereof as a raw material to form a ring with a lithium metal agent by a continuous reaction, so as to synthesize the propellane compound. A technical scheme of the present disclosure is applied, and a continuous reaction device is used.Type: GrantFiled: June 18, 2019Date of Patent: January 2, 2024Assignee: JILIN ASYMCHEM LABORATORIES CO., LTD.Inventors: Hao Hong, Enxuan Zhang, Jiangping Lu, Fuliang Wei, Sihang Yang
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Patent number: 11186537Abstract: Provided are: a method for producing a compound that excels in storage stability and handleability; the compound; and an epoxy curing agent containing the compound. The method for producing a compound represented by Formula (1-1) includes subjecting the compound represented by Formula (5-1) to an addition reaction to add ethylene and/or propylene in the presence of a base. In Formula (5-1), RX to RZ each independently represent a hydrogen atom, an ethyl group, an n-propyl group, or an isopropyl group, and n is an integer of from 1 to 3. In Formula (1-1), RA to RD each independently represent a hydrogen atom, an ethyl group, an n-propyl group, or an isopropyl group, and n is an integer of from 1 to 3.Type: GrantFiled: May 28, 2019Date of Patent: November 30, 2021Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventors: Yoichi Takano, Kazuyoshi Uera
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Patent number: 9029603Abstract: A process for preparing alkylated p-phenylenediamine having the steps of reacting aniline and nitrobenzene in presence of a complex base catalyst to obtain 4-aminodiphenylamine intermediates, hydrogenating the 4-aminodiphenylamine intermediates to 4-aminodiphenylamine in presence of a hydrogenation catalyst, and reductively alkylating the 4-aminodiphenylamine to alkylated p-phenylenediamine.Type: GrantFiled: September 14, 2012Date of Patent: May 12, 2015Assignee: Jiangsu Sinorgchem Technology Co., Ltd.Inventors: Xiaogen Feng, Nongyue Wang, Xiaohui Mao, Ruibiao Yu, Qianwen Cheng
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Publication number: 20150105588Abstract: Aromatic amines, for example, diarylamines such as diphenylamine, dinaphthylamine, N-phenyl-N-naphthyl amine etc., are alkylated by passing a mixture of the amine and an olefin, though a clay catalyst in a fixed bed reactor system. The process is conveniently run as a continued process, produces an alkylated aromatic amine in excellent purity and provides efficiencies in material and energy use.Type: ApplicationFiled: October 8, 2014Publication date: April 16, 2015Applicant: CHEMTURA CORPORATIONInventors: MITCHEL COHN, RONALD ABBOTT, ALAN B. TRUE, HUIYUAN CHEN
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Patent number: 8921600Abstract: The invention relates to a process for producing carbon fillers having covalently bonded amino groups, by converting a mixture comprising carbon fillers and alkali metals and/or alkaline earth metals and/or amides thereof in liquid anhydrous ammonia, optionally together with an inert solvent, at temperatures of 35 to 500° C. and a pressure of 30 to 250 bar.Type: GrantFiled: May 17, 2012Date of Patent: December 30, 2014Assignee: BASF SEInventors: Christof Wilhelm Wigbers, Marion Kristina Brinks, Johann-Peter Melder
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Patent number: 8828916Abstract: The present invention relates to a process for preparing nonylated diphenylamines which improves nonene usage by recycling and reusing stripped nonene from an earlier process. The process comprising consecutive recycle of recovered nonene is conducted at a sequential two step temperature reaction, namely a more severe temperature followed by a lower temperature. The product prepared by this process is a useful antioxidant for lubricating oil compositions.Type: GrantFiled: December 20, 2007Date of Patent: September 9, 2014Assignee: Chevron Oronite Company LLCInventor: Francois Simard
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Publication number: 20130225815Abstract: A method of forming a fluorinated molecular entity includes reacting in a reaction mixture an aromatic halide, copper, a fluoroalkyl group, and a ligand. The aromatic halide includes an aromatic group and a halogen substituent bonded to the aromatic group. The ligand includes at least one group-V donor selected from phosphorus and an amine. The overall molar ratio of copper to aromatic halide in the reaction mixture is from 0.2 to 3. The method further includes forming a fluoroalkylarene including the aromatic group and the fluoroalkyl group bonded to the aromatic group. A composition, which may be used in the method, consists essentially of copper, the fluoroalkyl group, and the ligand, where the molar ratio of copper to the fluoroalkyl group is approximately 1.Type: ApplicationFiled: February 19, 2013Publication date: August 29, 2013Applicant: The Board of Trustees of the University of IllinoisInventors: John F. Hartwig, Hiroyuki Morimoto, Patrick Fier
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Publication number: 20130184485Abstract: What is described is a process for preparing organic compounds of the general formula (I) R—R???(I) by converting a corresponding compound of the general formula (II) R—X ??(II) in which X is fluorine, chlorine, bromine or iodine to an organomagnesium compound of the general formula (III) [M+]n[RmMgXkY1]??(III) wherein compounds of the formula (III) are reacted with a compound of the general formula (IV) characterized in that the reaction of (III) with (IV) is performed in the presence of a) catalytic amounts of an iron compound, based on the compound of the general formula (II), and optionally in the presence of b) a nitrogen-, oxygen- and/or phosphorus-containing additive in a catalytic or stoichiometric amount, based on the compound of the general formula (II).Type: ApplicationFiled: February 1, 2011Publication date: July 18, 2013Applicant: SALTIGO GMBHInventors: Matthias Gotta, Bernd Wilhelm Lehnemann, Waldemar Maximilian Czaplik, Matthias Mayer, Axel Jacobi Von Wangelin
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Publication number: 20130150607Abstract: This invention is directed to a new process for making an alkylaromatic compound. In an embodiment of this invention, the process is directed to selective synthesizing an alkylaromatic compound comprising a high amount of dialkylate product. In general, this process involves contacting at least one alkylatable aromatic compound with an alkylating agent and a catalyst under suitable reaction conditions such that the resulting reactor effluent prior to any stripping step may be characterized by a dialkylate product content of at least 44 wt % and a trialkylate and higher polyalkylate product content of no more than 20 wt %. The alkylaromatic compounds produced have excellent thermal and oxidative stabilities, good additive solvency, and improved seal compatibility while maintaining good VI and low temperature properties. They are useful as lubricant basestocks and lubricant additives.Type: ApplicationFiled: December 7, 2011Publication date: June 13, 2013Inventor: Beth A. WINSETT
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Publication number: 20130150608Abstract: This invention is directed to an improvement in the process for the production of alkylaromatic compounds that results in lower levels of residual unreacted materials in the final product. This invention comprises: 1) alkylation of an aromatic compound with an alkylating agent and a catalyst to produce an effluent stream comprising an alkylaromatic compound and unreacted materials; 2) heating the effluent stream; 3) stripping the effluent stream in a stripping device in the presence of steam; 4) separating a stripping stream from the stripping device, the stripping stream rich in unreacted materials; and 5) separating a product stream from the stripping device, the product stream rich in alkylated aromatic compound.Type: ApplicationFiled: December 13, 2011Publication date: June 13, 2013Inventors: Beth A. Winsett, James I. Arnett, II, Kenwyn M. Leger, Brady A. Compton
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Publication number: 20130066113Abstract: A process for preparing alkylated p-phenylenediamine having the steps of reacting aniline and nitrobenzene in presence of a complex base catalyst to obtain 4-aminodiphenylamine intermediates, hydrogenating the 4-aminodiphenylamine intermediates to 4-aminodiphenylamine in presence of a hydrogenation catalyst, and reductively alkylating the 4-aminodiphenylamine to alkylated p-phenylenediamine.Type: ApplicationFiled: September 14, 2012Publication date: March 14, 2013Applicant: Jiangsu Sinorgchem Technology Co., Ltd.Inventors: Xiaogen FENG, Nongyue WANG, Xiaohui MAO, Ruibiao YU, Qianwen CHENG
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Patent number: 8329952Abstract: The present invention relates to process for the preparation of novel crystalline Desmethylvenlafaxine succinate polymorphic Forms-A, B. The present invention also relates to novel processes for the preparation of 0-Desmethylvenlafaxine succinate polymorphic Forms-(I), (II), (III) and amorphous.Type: GrantFiled: July 15, 2008Date of Patent: December 11, 2012Assignee: Matrix Laboratories LimitedInventors: Ramakoteswara Rao Jetti, Purandhar Koilkonda, Jagan Mohana Chary Tummanapally, Mohana Vamsi Krishna Vadlamudi, Prasanth Kumar Barik, Om Dutt Tyagi
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Patent number: 8236988Abstract: Methods are provided for preparing branched alkyl-substituted-anilines, such as 2-(1,3-dimethylbutyl)aniline. Such methods comprise combining aniline, an alkyl-substituted-1-alkene, such as 4-methyl-i-pentene, and an aluminum alkyl catalyst.Type: GrantFiled: August 1, 2008Date of Patent: August 7, 2012Assignee: Albemarle CorporationInventor: Kannappan Chockalingam
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Patent number: 7928265Abstract: Method of preparation of antioxidant composition on the basis of diphenylamine by catalytic alkylation of diphenylamine by an threefold excess of diisobutylene with regard to diphenylamine in the presence of an alkylation catalyst t in an amount of 5 to 30% by weight, as referred to diphenylamine, at a temperature of 140 to 160° C. Water contained in the catalyst, is removed and subsequently diphenylamine is left to complete the reaction with diisobutylene and after the reaction is finished, the reaction mixture is separated from the catalyst, unreacted diisobutylene is removed from it and the reaction product is obtained.Type: GrantFiled: May 5, 2006Date of Patent: April 19, 2011Assignee: Duslo A.S.Inventors: Viera Andruskova, Jan Uhlar, Peter Lehocky, Jaroslav Horak
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Patent number: 7847030Abstract: Provided is a process for making a diphenylamine-functionalized poly-?-olefin. The process has the following step: reacting an amount of a poly-?-olefin having a terminal double bond with a diphenylamine in the presence of a catalyst. The poly-?-olefin has a terminal double bond having a number average molecular weight of 120 to 600. The ratio of poly-?-olefin to diphenylamine is 1.0:1.0 to 10.0:1.0. Provided is also a diphenylamine-functionalized poly-?-olefin product.Type: GrantFiled: February 29, 2008Date of Patent: December 7, 2010Assignee: ExxonMobil Research and Engineering CompanyInventor: Abhimanyu O. Patil
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Patent number: 7674935Abstract: Methods for preparing crystalline forms of O-desmethylvenlafaxine are described.Type: GrantFiled: April 17, 2007Date of Patent: March 9, 2010Assignee: Teva Pharmaceutical Industries Ltd.Inventors: Sigalit Levi, Valerie Niddam-Hildesheim, Iamas Koltai
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Patent number: 7605290Abstract: The present invention describes processes for the preparation of O-desmethylvenlafaxine and tridesmethylvenlafaxine, which may be used as an intermediate in preparing O-desmethylvenlafaxine.Type: GrantFiled: July 26, 2007Date of Patent: October 20, 2009Assignee: Teva Pharmaceutical Industries Ltd.Inventors: Valerie Niddam-Hildesheim, Natalia Shenkar, Sharona Shachan-Tov
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Publication number: 20090156449Abstract: An alkylated 1,3-benzenediamine compound used as a deposit-control lubricant additives for organic materials including lubricating oil, gasoline, and diesel fuels. The invention improves the oxidative stability of the lubricants and fuels by adding the alkylated 1,3-benzenediamine compound. The alkylated 1,3-benzenediamine compound is formed using a catalytic hydrogenation that alkylates the 4 and/or 6 position of the central aromatic ring.Type: ApplicationFiled: September 17, 2008Publication date: June 18, 2009Inventors: Robert G. Rowland, Joseph F. Stieber, Clifford M. Pratt, Ronald D. Abbott
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Patent number: 7528283Abstract: The invention provides an improved process for preparing diamines and polyamines from the diphenylmethane series by reacting aniline and formaldehyde in the presence of an acid catalyst, the improvement involving the aniline containing less than about 3 wt. % of diamines and polyamines from the diphenylmethane series, based on the weight of the aniline.Type: GrantFiled: January 24, 2007Date of Patent: May 5, 2009Assignee: Bayer MeterialScience AGInventors: Fritz Pohl, Jeffrey Bolton, Richard Adamson, Heinz-Herbert Muller, Rudolf Uchdorf
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Publication number: 20080312472Abstract: Para-alkylated diphenylamine antioxidants are made by catalytically alkylating diphenylamine with an alkylating agent in the form of a mixture of branched-chain oligomers of butene, the alkylating agent having an average molecular weight in the range of 140 to 300 and a methylvinylidene isomer content of no greater than 10%.Type: ApplicationFiled: June 14, 2007Publication date: December 18, 2008Inventors: Stephen Arrowsmith, Christopher James Booth, Aubrey L. Burrows, Paul Wilson, Ronald P. Wangner
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Patent number: 7456319Abstract: A method is provided for producing primarily para alkyl aromatic amines by alkylating a primary aromatic amine with an olefin in the presence of an acid activated clay.Type: GrantFiled: December 8, 2005Date of Patent: November 25, 2008Assignee: ExxonMobil Research and Engineering CompanyInventors: George A Knudsen, Richard H. Schlosberg
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Patent number: 7435854Abstract: The present invention provides an efficient method of making O-desmethyl-venlafaxine.Type: GrantFiled: June 1, 2007Date of Patent: October 14, 2008Assignee: WyethInventor: Beat Theodor Weber
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Publication number: 20080234517Abstract: A process for alkylation of a N?-phenyl-N-alkyl-p-phenylenediamine of specified formula in an ionic liquid unexpectedly produces a N?-phenyl-N-alkyl(alkylphenylene)diamine of a second specified formula. The use of an inorganic liquid permits convenient separation of the alkylated reaction product from the reaction mixture.Type: ApplicationFiled: April 16, 2008Publication date: September 25, 2008Applicant: Chemtura CorporationInventors: Steven J. HOBBS, Joseph F. STIEBER
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Publication number: 20080161216Abstract: The present invention relates to a process for preparing nonylated diphenylamines which improves nonene usage by recycling and reusing stripped nonene from an earlier process. The process comprising consecutive recycle of recovered nonene is conducted at a sequential two step temperature reaction, namely a more severe temperature followed by a lower temperature. The product prepared by this process is a useful antioxidant for lubricating oil compositions.Type: ApplicationFiled: December 20, 2007Publication date: July 3, 2008Inventor: Francois Simard
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Patent number: 7390927Abstract: A process for preparing a 3-aminophenylacetylene compound of formula (5), including: a) reacting a 3-haloaniline compound of formula (1) with an acetylene compound of formula (2) in the presence of a palladium compound, a copper compound, and an amine compound of formula (3) to form an aniline compound of formula (4); b) precipitating the aniline compound of formula (4) in the form of a crystal, and isolating it by solid/liquid separation; and c) reacting the aniline compound of formula (4) with a base to obtain 3-aminophenylacetylene.Type: GrantFiled: March 30, 2006Date of Patent: June 24, 2008Assignee: FUJILFILM CorporationInventors: Daisuke Urazoe, Hideto Mori
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Patent number: 7390928Abstract: A process for alkylation of a N?-phenyl-N-alkyl-p-phenylenediamine of specified formula in an ionic liquid unexpectedly produces a N?-phenyl-N-alkyl(alkylphenylene)diamine of a second specified formula. The use of an inorganic liquid permits convenient separation of the alkylated reaction product from the reaction mixture.Type: GrantFiled: December 14, 2005Date of Patent: June 24, 2008Assignee: Chemtura CorporationInventors: Steven J. Hobbs, Joseph F. Stieber
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Patent number: 7378554Abstract: A process for ring-alkylating aniline or an aniline derivative in which aniline or an aniline derivative is reacted with an alkylating agent in the presence of an ionic liquid which includes a Lewis acid and a quaternary cation, to produce a ring-alkylated alkylaniline or a ring-alkylated aniline derivative. The use of an ionic liquid permits convenient separation of the alkylated reaction product from the reactants.Type: GrantFiled: December 14, 2005Date of Patent: May 27, 2008Assignee: Chemtura CorporationInventors: Steven J. Hobbs, Venkatramanan K. Madabusi, Jin-Yun Wang, Joseph F. Steiber
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Patent number: 7342133Abstract: The invention relates to substituted amino compounds, to processes for their preparation, to pharmaceutical formulations containing these compounds and to the use of these substances in the preparation of pharmaceutical formulations, especially for the treatment or inhibition of depression, anxiety, pain and urinary incontinence, and to related methods of treating or inhibiting these disorders.Type: GrantFiled: January 16, 2007Date of Patent: March 11, 2008Assignee: Gruenenthal GmbHInventors: Petra Bloms-Funke, Elmar Friderichs, Ivars Graudums, Hagen-Heinrich Hennies, Achim Kless, Klaus Schiene, Oswald Zimmer
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Patent number: 7253321Abstract: The invention provides a process for the preparation of polyamines of the diphenylmethane series. This process comprises a) reacting aniline and formaldehyde in a molar ratio of 1.5:1 to 6:1, in the presence of an acid catalyst at temperatures of 20° C. to 100° C., in which the water content in the acid reaction mixture is <20 wt. % and a degree of protonation of <15% is established, and b) increasing the temperature of the reaction to a temperature of 110° C. to 250° C. when the ratio of the weight contents of p-aminobenzylaniline to 4,4?-MDA in the reaction mixture falls below a value of 1.00.Type: GrantFiled: June 29, 2005Date of Patent: August 7, 2007Assignee: Bayer MaterialScience AGInventors: Torsten Hagen, Daniel Koch, Hans-Georg Pirkl, Fritz Pohl, Stefan Wershofen, Rudolf Uchdorf, Richard Adamson
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Patent number: 7145038Abstract: A process for alkylation of a diphenylamine compound in an ionic liquid. The use of an ionic liquid permits convenient separation of the alkylated reaction product from the reaction mixture.Type: GrantFiled: December 14, 2005Date of Patent: December 5, 2006Assignee: Chemtura CorporationInventor: Steven J. Hobbs
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Patent number: 7005553Abstract: A method for the regioselective ortho-directed nitration of phenolic compounds useful for the preparation of ortho-nitro-phenols according to formula (I) is described.Type: GrantFiled: July 22, 2002Date of Patent: February 28, 2006Assignee: Portela, C.A., S.A.Inventor: David Alexander Learmonth
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Patent number: 6689912Abstract: The present invention provides an efficient method of making O-desmethyl-venlafaxine.Type: GrantFiled: November 26, 2002Date of Patent: February 10, 2004Assignee: WyethInventor: Beat T. Weber
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Patent number: 6639102Abstract: Polyisocyanates of the diphenyl methane series having reduced color values are obtained by a) reacting aniline and formaldehyde in the presence of an acid catalyst to form a polyamine, b) neutralizing the reaction mixture containing polyamine with a base, c) separating the neutralized mixture into the aqueous and the organic phases, d) adding a base to the organic phase and then e) phosgenating the resulting polyamine to produce the corresponding polyisocyanate.Type: GrantFiled: March 10, 2003Date of Patent: October 28, 2003Assignee: Bayer AktiengesellschaftInventors: Torsten Hagen, Friedhelm Kämper, Daniel Koch, Rudolf Uchdorf, Stefan Wershofen
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Patent number: 6624201Abstract: The invention relates to high purity (1R,2S,4R)-(−)-2-[(2′-{N,N-dimethylamino}-ethoxy)]-2-[phenyl]-1,7,7-tri-[methyl]-bicyclo[2.2.1]heptane and pharmaceutically acceptable acid addition salts thereof containing not more than 0.2% of (1R,3S,4R)-3-[(2′-{N,N-dimethylamino}-ethyl)]-1,7,7-tri-[methyl]-bicyclo[2.2.1]heptane-2-one and/or of a pharmaceutically acceptable acid addition salt thereof. Furthermore the invention is concerned with a process for the preparation of these compounds. Moreover the invention relates to medicaments containing 1 or more of these compounds and their use.Type: GrantFiled: October 30, 2001Date of Patent: September 23, 2003Assignee: Orion CorporationInventors: Gyula Lukács, Gyula Simig, Tibor Mezei, Zoltán Budai, Márta Porcs-Makkay, György Krasznai, Kálmán Nagy, Györgyi Donáth Vereczkey, Tibor Szabó, Norbert Németh, János Szulágyi
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Patent number: 6600074Abstract: The present invention provides an aniline derivative represented by the formula (I) wherein R1 and R2 are each H, (C1-12)alkyl, (C3-8)cycloalkyl, hydroxy(C1-12)alkyl, hydroxycarbonyl (C1-12)alkyl, (C1-6)-alkoxycarbonyl(C1-6)alkyl, —COR8, wherein R8 is H, halo-(C1-12)alkyl, (C3-8)cycloalkyl or (substituted) phenyl, COOR9, wherein R9 is a halo(C1-6)alkyl group, (substituted) phenyl or (substituted) benzyl; R3, R4, R5, R6and R7 are each H, halogen, OH, nitro, halo(C1-12)alkylthio, (substituted)amino-(C1-2)alkyl, (substituted) phenyl, (substituted) benzyl, amino, —N(R10)R11 wherein R10 and R11 are each H, alkyl, cycloalkyl, (substituted) phenyl, (substituted) benzyl, —COR8 or COOR9, or (C2-27)perfluoroalkyl, etc., and a process for producing the aniline derivative. According to the process of the present invention, perfluoroalkylaniline derivatives can be obtained by using various anilines as the substrate with a high position selectivity and high yield.Type: GrantFiled: July 29, 2002Date of Patent: July 29, 2003Assignee: Nihon Nohyaku Co., Ltd.Inventors: Masanobu Onishi, Akihiko Yoshiura, Eiji Kohno, Kenji Tsubata
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Patent number: 6566571Abstract: Process for preparing monofunctional, bifunctional and/or polyfunctional biaryls of the formula (I) Ar—Ar′ (I) by reacting haloaromatics of the formula (II) Ar—X (II) with boron compounds of the formula (IIIa), (IIIb) and/or (IIIc) in the presence of at least one palladium complex of the formula (IVa) or (IVb)Type: GrantFiled: February 4, 2002Date of Patent: May 20, 2003Assignee: Degussa AGInventors: Thomas Riermeier, Matthias Beller, Alexander Zapf
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Patent number: 6392111Abstract: Olefins containing aromatic substituents are synthesized without the addition of phosphonium salts or phosphanes with the aid of a PdII compound as a catalyst in the presence of nitrogen-containing additives such as N,N-dimethylglycine and a base.Type: GrantFiled: March 21, 2001Date of Patent: May 21, 2002Assignee: Studiengesellschaft Kohle mbHInventors: Manfred T. Reetz, Gunther Lohmer, Renate Lohmer, Elke Westermann
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Publication number: 20020045775Abstract: The present invention relates to a process wherein heterogeneous finely dispersed palladium catalysts are used for cross coupling of alkenyl halides and boronic acids in the presence of base in an aprotic solvent to produce aryl- or heteroaryl-olefin compounds. The process provides for use with either electron-withdrawing or electron-donating substituents for cross coupling of alkyl halides with boronic acids.Type: ApplicationFiled: July 16, 2001Publication date: April 18, 2002Inventors: Yongkui Sun, Carl LeBlond, John R. Sowa
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Patent number: 6355839Abstract: A process for preparation of alkylated diphenylamine antioxidant which comprises alkylating diphenylamine with a polyisobutylene in the presence of a clay catalyst, wherein the polyisobutylene has an average molecular weight in the range of 120 to 600 and wherein the polyisobutylene contains at least 25% methylvinylidene isomer.Type: GrantFiled: August 31, 2001Date of Patent: March 12, 2002Assignee: Chevron U.S.A., Inc.Inventor: Anatoli Onopchenko
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Patent number: 6315925Abstract: The invention relates to a mixture of nonylated diphenylamines, especially dinonylated diphenylamines, and to a technically advantageous methodological process for the preparation of that mixture by using acid catalysts in small quantities. The mixture is used as an additive for stabilizing organic products that are subjected to oxidative, thermal and/or light-induced degradation.Type: GrantFiled: February 14, 2000Date of Patent: November 13, 2001Assignee: Ciba Specialty Chemicals CorporationInventors: Beat Michael Aebli, Samuel Evans, Sandor Gati
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Patent number: 6215035Abstract: The invention relates to a process for the preparation of aralkylated aromatic compound with both small and large size aralkylating agents; wherein the catalyst used is heterogeneous solid catalyst removable from the reaction products by simple filtration, thus allowing the separated catalyst to be reused in the process. The catalyst is selected from micro or mesoporous gallosilicates and galloaluminosilicates, having structure similar to that of zeolites known in the prior art.Type: GrantFiled: January 11, 1999Date of Patent: April 10, 2001Assignee: Council of Scientific and Industrial ResearchInventors: Vasant Ramchandra Choudhary, Suman Kumar Jana, B-Phani Kiran
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Patent number: 6204412Abstract: A method of manufacturing an alkylated diphenylamine composition to generate an alkylated diphenylamine composition with relatively low amounts of unsubstituted diphenylamine, based on the total weight of substituted and unsubstituted diphenylamine in the alkylated diphenylamine composition. The method includes reaction of unsubstituted diphenylamine with at least two olefins. In at least some instances, the alkylated diphenylamine composition may be used, for example, as an antioxidant in a lubricating fluid or polymer composition.Type: GrantFiled: April 16, 1999Date of Patent: March 20, 2001Assignee: The B. F. Goodrich CompanyInventor: John T. Lai
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Patent number: 6028225Abstract: Hydroxy-substituted hydroxylamine antioxidants can be prepared by reacting hydroxylamine or a mono-substituted hydroxylamine, in free base form, with an epoxide. The antioxidant reaction product can be used without isolation from the reaction solution, and combined with a color developing agent to provide a photographic color developing composition in either concentrated or working strength formulations. The method for preparing the antioxidant is rapid and efficient because of the use of the free base form of the hydroxylamine reactant, higher temperatures (at or above 50.degree. C.) and certain molar ratios of reactants.Type: GrantFiled: September 15, 1998Date of Patent: February 22, 2000Assignee: Eastman Kodak CompanyInventor: Lynda W. McGarry
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Patent number: 5962739Abstract: The present invention provides a process for the production of an N,N-dialkylaminophenyl alkanol having the formula: ##STR1## in which R.sub.1 and R.sub.2, independently, are C.sub.1 -C.sub.4 alkyl, R.sub.3 is hydrogen, halogen, cyano, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy and n is an integer from 1 to 4, comprising reacting an aminophenyl alkanol having the formula: ##STR2## in which R.sub.3 and n have their previous significance, with at least two moles of a dialkylsulfate having the formula: ##STR3## in which R.sub.1 and R.sub.2 have their previous significance. N,N-dialkylaminophenyl alkanols so obtained are valuable as intermediates for a wide range of end-products and are also useful, e.g., as accelerators for the peroxide-catalyzed polymerization of vinyl monomers, especially in polymerizable or curable formulations employed in dental applications.Type: GrantFiled: May 19, 1998Date of Patent: October 5, 1999Assignee: Ciba Specialty Chemicals CorporationInventors: Claus Korhummel, Hanspeter Baier
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Patent number: 5902902Abstract: A process for the preparation of 3-aminophenylacetylene derivatives of formula: ##STR1## wherein R.sub.1 is as defined in the disclosure ##STR2## wherein Y is as defined in the disclosureR--C.tbd.C--Hwherein R is as defined in the disclosure.Type: GrantFiled: February 18, 1998Date of Patent: May 11, 1999Assignee: Secifarma S.p.A.Inventors: Walter Cabri, Erminio Oldani
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Patent number: 5840979Abstract: The present invention relates to the use of a group of propargylamines of the general formula (I) ##STR1## wherein R.sup.1 is hydrogen or CH.sub.3 and R.sup.2 is (CH.sub.2).sub.n CH.sub.3 and n is an integer from 0 to 16, and salts thereof, as cellular rescue agents in the treatment and prevention of diseases in which cell death occurs by apoptosis. Some of the compounds of formula I are novel. The invention is also directed to the use of these compounds in the treatment of these diseases, as well as to processes for the preparation of the compounds.Type: GrantFiled: July 14, 1997Date of Patent: November 24, 1998Assignee: University of SaskatchewanInventors: David Durden, Alick Paterson, Bruce Davis, Lillian Dyck, Peter Yu, Xinmin Li, Alan Boulton
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Patent number: 5817831Abstract: Aliphatic hydrocarbyl-substituted aromatic amines are prepared by reacting an aromatic amine and an aliphatic hydrocarbylating agent, such as an olefin, in the presence of a heteropolyacid catalyst such as Cs.sub.2.5 H.sub.0.5 PW.sub.12 O.sub.40, for a period of time and at a temperature sufficient to permit reaction.Type: GrantFiled: September 8, 1997Date of Patent: October 6, 1998Assignee: The Lubrizol CorporationInventors: Douglas C. Rhubright, James D. Burrington, Ping Y. Zhu
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Patent number: 5750787Abstract: A process for monoalkylating diphenylamine using a clay catalyst is disclosed which results in a reaction product having substantial amounts of desirable monoalkylated diphenylamine and minimal amounts of less desirable disubstituted diphenylamine and unsubstituted diphenylamine. The disclosed process uses clay catalysts which favor monoalkylation over dialkylation and specific conditions such as reaction temperature, mole ratios of alkylating olefin to diphenylamine, reaction times, and catalyst amounts. Preferred olefins are diisobutylene and linear alpha olefins having from 6 or 8 to 18 carbon atoms. When more than 1 wt. % residual unreacted diphenylamine is present it may be converted to alkylated diphenylamine by reacting with styrene, alpha-methylstyrene or isobutylene.Type: GrantFiled: May 30, 1996Date of Patent: May 12, 1998Assignee: B. F. Goodrich CompanyInventors: John T. Lai, Deborah S. Filla
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Patent number: 5734084Abstract: An improved method for making alkylated aromatic amines is disclosed. The method includes a new alkylating catalyst system comprising an aromatic amine alkylating catalyst and a non-catalyst solid such as silica. The method results in faster reaction rates and higher yields of alkylated aromatic amines.Type: GrantFiled: December 17, 1996Date of Patent: March 31, 1998Assignee: The Lubrizol CorporationInventor: Ping Y. Zhu
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Patent number: 5672752Abstract: A process for monoalkylating diphenylamine using clay catalyst is disclosed which results in a reaction product having substantial amounts of desirable monoalkylated diphenylamine and minimal amounts of less desirable disubstituted diphenylamine and unsubstituted diphenylamine. The disclosed process uses clay catalysts which favor monoalkylation over dialkylation and specific conditions such as reaction temperature and mole ratios of alkylating olefin to diphenylamine.Type: GrantFiled: September 13, 1995Date of Patent: September 30, 1997Assignee: The BFGoodrich CompanyInventors: John T. Lai, Deborah S. Filla