Preparing Directly By Ring Alkylation Or Dealkylaton Patents (Class 564/409)
  • Patent number: 11186537
    Abstract: 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: Grant
    Filed: May 28, 2019
    Date of Patent: November 30, 2021
    Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Yoichi Takano, Kazuyoshi Uera
  • Patent number: 9029603
    Abstract: 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: Grant
    Filed: September 14, 2012
    Date of Patent: May 12, 2015
    Assignee: Jiangsu Sinorgchem Technology Co., Ltd.
    Inventors: Xiaogen Feng, Nongyue Wang, Xiaohui Mao, Ruibiao Yu, Qianwen Cheng
  • Publication number: 20150105588
    Abstract: 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: Application
    Filed: October 8, 2014
    Publication date: April 16, 2015
    Applicant: CHEMTURA CORPORATION
    Inventors: MITCHEL COHN, RONALD ABBOTT, ALAN B. TRUE, HUIYUAN CHEN
  • Patent number: 8921600
    Abstract: 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: Grant
    Filed: May 17, 2012
    Date of Patent: December 30, 2014
    Assignee: BASF SE
    Inventors: Christof Wilhelm Wigbers, Marion Kristina Brinks, Johann-Peter Melder
  • Patent number: 8828916
    Abstract: 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: Grant
    Filed: December 20, 2007
    Date of Patent: September 9, 2014
    Assignee: Chevron Oronite Company LLC
    Inventor: Francois Simard
  • Publication number: 20130225815
    Abstract: 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: Application
    Filed: February 19, 2013
    Publication date: August 29, 2013
    Applicant: The Board of Trustees of the University of Illinois
    Inventors: John F. Hartwig, Hiroyuki Morimoto, Patrick Fier
  • Publication number: 20130184485
    Abstract: 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: Application
    Filed: February 1, 2011
    Publication date: July 18, 2013
    Applicant: SALTIGO GMBH
    Inventors: Matthias Gotta, Bernd Wilhelm Lehnemann, Waldemar Maximilian Czaplik, Matthias Mayer, Axel Jacobi Von Wangelin
  • Publication number: 20130150608
    Abstract: 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: Application
    Filed: December 13, 2011
    Publication date: June 13, 2013
    Inventors: Beth A. Winsett, James I. Arnett, II, Kenwyn M. Leger, Brady A. Compton
  • Publication number: 20130150607
    Abstract: 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: Application
    Filed: December 7, 2011
    Publication date: June 13, 2013
    Inventor: Beth A. WINSETT
  • Publication number: 20130066113
    Abstract: 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: Application
    Filed: September 14, 2012
    Publication date: March 14, 2013
    Applicant: Jiangsu Sinorgchem Technology Co., Ltd.
    Inventors: Xiaogen FENG, Nongyue WANG, Xiaohui MAO, Ruibiao YU, Qianwen CHENG
  • Patent number: 8329952
    Abstract: 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: Grant
    Filed: July 15, 2008
    Date of Patent: December 11, 2012
    Assignee: Matrix Laboratories Limited
    Inventors: Ramakoteswara Rao Jetti, Purandhar Koilkonda, Jagan Mohana Chary Tummanapally, Mohana Vamsi Krishna Vadlamudi, Prasanth Kumar Barik, Om Dutt Tyagi
  • Patent number: 8236988
    Abstract: 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: Grant
    Filed: August 1, 2008
    Date of Patent: August 7, 2012
    Assignee: Albemarle Corporation
    Inventor: Kannappan Chockalingam
  • Patent number: 7928265
    Abstract: 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: Grant
    Filed: May 5, 2006
    Date of Patent: April 19, 2011
    Assignee: Duslo A.S.
    Inventors: Viera Andruskova, Jan Uhlar, Peter Lehocky, Jaroslav Horak
  • Patent number: 7847030
    Abstract: 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: Grant
    Filed: February 29, 2008
    Date of Patent: December 7, 2010
    Assignee: ExxonMobil Research and Engineering Company
    Inventor: Abhimanyu O. Patil
  • Patent number: 7674935
    Abstract: Methods for preparing crystalline forms of O-desmethylvenlafaxine are described.
    Type: Grant
    Filed: April 17, 2007
    Date of Patent: March 9, 2010
    Assignee: Teva Pharmaceutical Industries Ltd.
    Inventors: Sigalit Levi, Valerie Niddam-Hildesheim, Iamas Koltai
  • Patent number: 7605290
    Abstract: 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: Grant
    Filed: July 26, 2007
    Date of Patent: October 20, 2009
    Assignee: Teva Pharmaceutical Industries Ltd.
    Inventors: Valerie Niddam-Hildesheim, Natalia Shenkar, Sharona Shachan-Tov
  • Publication number: 20090156449
    Abstract: 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: Application
    Filed: September 17, 2008
    Publication date: June 18, 2009
    Inventors: Robert G. Rowland, Joseph F. Stieber, Clifford M. Pratt, Ronald D. Abbott
  • Patent number: 7528283
    Abstract: 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: Grant
    Filed: January 24, 2007
    Date of Patent: May 5, 2009
    Assignee: Bayer MeterialScience AG
    Inventors: Fritz Pohl, Jeffrey Bolton, Richard Adamson, Heinz-Herbert Muller, Rudolf Uchdorf
  • Publication number: 20080312472
    Abstract: 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: Application
    Filed: June 14, 2007
    Publication date: December 18, 2008
    Inventors: Stephen Arrowsmith, Christopher James Booth, Aubrey L. Burrows, Paul Wilson, Ronald P. Wangner
  • Patent number: 7456319
    Abstract: 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: Grant
    Filed: December 8, 2005
    Date of Patent: November 25, 2008
    Assignee: ExxonMobil Research and Engineering Company
    Inventors: George A Knudsen, Richard H. Schlosberg
  • Patent number: 7435854
    Abstract: The present invention provides an efficient method of making O-desmethyl-venlafaxine.
    Type: Grant
    Filed: June 1, 2007
    Date of Patent: October 14, 2008
    Assignee: Wyeth
    Inventor: Beat Theodor Weber
  • Publication number: 20080234517
    Abstract: 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: Application
    Filed: April 16, 2008
    Publication date: September 25, 2008
    Applicant: Chemtura Corporation
    Inventors: Steven J. HOBBS, Joseph F. STIEBER
  • Publication number: 20080161216
    Abstract: 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: Application
    Filed: December 20, 2007
    Publication date: July 3, 2008
    Inventor: Francois Simard
  • Patent number: 7390928
    Abstract: 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: Grant
    Filed: December 14, 2005
    Date of Patent: June 24, 2008
    Assignee: Chemtura Corporation
    Inventors: Steven J. Hobbs, Joseph F. Stieber
  • Patent number: 7390927
    Abstract: 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: Grant
    Filed: March 30, 2006
    Date of Patent: June 24, 2008
    Assignee: FUJILFILM Corporation
    Inventors: Daisuke Urazoe, Hideto Mori
  • Patent number: 7378554
    Abstract: 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: Grant
    Filed: December 14, 2005
    Date of Patent: May 27, 2008
    Assignee: Chemtura Corporation
    Inventors: Steven J. Hobbs, Venkatramanan K. Madabusi, Jin-Yun Wang, Joseph F. Steiber
  • Patent number: 7342133
    Abstract: 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: Grant
    Filed: January 16, 2007
    Date of Patent: March 11, 2008
    Assignee: Gruenenthal GmbH
    Inventors: Petra Bloms-Funke, Elmar Friderichs, Ivars Graudums, Hagen-Heinrich Hennies, Achim Kless, Klaus Schiene, Oswald Zimmer
  • Patent number: 7253321
    Abstract: 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: Grant
    Filed: June 29, 2005
    Date of Patent: August 7, 2007
    Assignee: Bayer MaterialScience AG
    Inventors: Torsten Hagen, Daniel Koch, Hans-Georg Pirkl, Fritz Pohl, Stefan Wershofen, Rudolf Uchdorf, Richard Adamson
  • Patent number: 7145038
    Abstract: 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: Grant
    Filed: December 14, 2005
    Date of Patent: December 5, 2006
    Assignee: Chemtura Corporation
    Inventor: Steven J. Hobbs
  • Patent number: 7005553
    Abstract: 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: Grant
    Filed: July 22, 2002
    Date of Patent: February 28, 2006
    Assignee: Portela, C.A., S.A.
    Inventor: David Alexander Learmonth
  • Patent number: 6689912
    Abstract: The present invention provides an efficient method of making O-desmethyl-venlafaxine.
    Type: Grant
    Filed: November 26, 2002
    Date of Patent: February 10, 2004
    Assignee: Wyeth
    Inventor: Beat T. Weber
  • Patent number: 6639102
    Abstract: 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: Grant
    Filed: March 10, 2003
    Date of Patent: October 28, 2003
    Assignee: Bayer Aktiengesellschaft
    Inventors: Torsten Hagen, Friedhelm Kämper, Daniel Koch, Rudolf Uchdorf, Stefan Wershofen
  • Patent number: 6624201
    Abstract: 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: Grant
    Filed: October 30, 2001
    Date of Patent: September 23, 2003
    Assignee: Orion Corporation
    Inventors: Gyula Lukács, Gyula Simig, Tibor Mezei, Zoltán Budai, Márta Porcs-Makkay, György Krasznai, Kálmán Nagy, Györgyi Donáth Vereczkey, Tibor Szabó, Norbert Németh, János Szulágyi
  • Patent number: 6600074
    Abstract: 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: Grant
    Filed: July 29, 2002
    Date of Patent: July 29, 2003
    Assignee: Nihon Nohyaku Co., Ltd.
    Inventors: Masanobu Onishi, Akihiko Yoshiura, Eiji Kohno, Kenji Tsubata
  • Patent number: 6566571
    Abstract: 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: Grant
    Filed: February 4, 2002
    Date of Patent: May 20, 2003
    Assignee: Degussa AG
    Inventors: Thomas Riermeier, Matthias Beller, Alexander Zapf
  • Patent number: 6392111
    Abstract: 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: Grant
    Filed: March 21, 2001
    Date of Patent: May 21, 2002
    Assignee: Studiengesellschaft Kohle mbH
    Inventors: Manfred T. Reetz, Gunther Lohmer, Renate Lohmer, Elke Westermann
  • Publication number: 20020045775
    Abstract: 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: Application
    Filed: July 16, 2001
    Publication date: April 18, 2002
    Inventors: Yongkui Sun, Carl LeBlond, John R. Sowa
  • Patent number: 6355839
    Abstract: 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: Grant
    Filed: August 31, 2001
    Date of Patent: March 12, 2002
    Assignee: Chevron U.S.A., Inc.
    Inventor: Anatoli Onopchenko
  • Patent number: 6315925
    Abstract: 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: Grant
    Filed: February 14, 2000
    Date of Patent: November 13, 2001
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Beat Michael Aebli, Samuel Evans, Sandor Gati
  • Patent number: 6215035
    Abstract: 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: Grant
    Filed: January 11, 1999
    Date of Patent: April 10, 2001
    Assignee: Council of Scientific and Industrial Research
    Inventors: Vasant Ramchandra Choudhary, Suman Kumar Jana, B-Phani Kiran
  • Patent number: 6204412
    Abstract: 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: Grant
    Filed: April 16, 1999
    Date of Patent: March 20, 2001
    Assignee: The B. F. Goodrich Company
    Inventor: John T. Lai
  • Patent number: 6028225
    Abstract: 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: Grant
    Filed: September 15, 1998
    Date of Patent: February 22, 2000
    Assignee: Eastman Kodak Company
    Inventor: Lynda W. McGarry
  • Patent number: 5962739
    Abstract: 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: Grant
    Filed: May 19, 1998
    Date of Patent: October 5, 1999
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Claus Korhummel, Hanspeter Baier
  • Patent number: 5902902
    Abstract: 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: Grant
    Filed: February 18, 1998
    Date of Patent: May 11, 1999
    Assignee: Secifarma S.p.A.
    Inventors: Walter Cabri, Erminio Oldani
  • Patent number: 5840979
    Abstract: 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: Grant
    Filed: July 14, 1997
    Date of Patent: November 24, 1998
    Assignee: University of Saskatchewan
    Inventors: David Durden, Alick Paterson, Bruce Davis, Lillian Dyck, Peter Yu, Xinmin Li, Alan Boulton
  • Patent number: 5817831
    Abstract: 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: Grant
    Filed: September 8, 1997
    Date of Patent: October 6, 1998
    Assignee: The Lubrizol Corporation
    Inventors: Douglas C. Rhubright, James D. Burrington, Ping Y. Zhu
  • Patent number: 5750787
    Abstract: 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: Grant
    Filed: May 30, 1996
    Date of Patent: May 12, 1998
    Assignee: B. F. Goodrich Company
    Inventors: John T. Lai, Deborah S. Filla
  • Patent number: 5734084
    Abstract: 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: Grant
    Filed: December 17, 1996
    Date of Patent: March 31, 1998
    Assignee: The Lubrizol Corporation
    Inventor: Ping Y. Zhu
  • Patent number: 5672752
    Abstract: 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: Grant
    Filed: September 13, 1995
    Date of Patent: September 30, 1997
    Assignee: The BFGoodrich Company
    Inventors: John T. Lai, Deborah S. Filla
  • Patent number: 5659084
    Abstract: Processes for preparing 2-substituted benzaldehydes of general formula (I), wherein: R.sub.1 is CH.sub.2 CH.sub.2 --(L.sub.1).sub.p --(CH.sub.2).sub.q --(L.sub.2).sub.r --CH.sub.2 --(T).sub.2 --Z; L.sub.1 and L.sub.2 are independently CH.sub.2 CH.sub.2, CH.dbd.CH or C.tbd.C; q is 0 to 8; p, r and s are independently 0 or 1; T is O, S, CH.sub.2, CH.dbd.CH, C.tbd.C; and Z is C.sub.1-4 alkyl, ethynyl, trifluoromethyl, isopropenyl, furanyl, thienyl, cyclohexyl or phenyl optionally mono substituted with CF.sub.3, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, methylthio, or trifluoromethylthio; and R.sub.2 and A are independently H, CF.sub.3, C.sub.1-4 alkyl, F, Cl, Br or I; are useful for preparing pharmaceutically active compounds.
    Type: Grant
    Filed: December 7, 1994
    Date of Patent: August 19, 1997
    Assignees: SmithKline Beecham Corporation, SmithKline Beecham plc
    Inventors: Kerry Joseph Gombatz, Michael Anthony Forth, Jerome Francis Hayes, Michael Barry Mitchell, Stephen Alexander Smith