Of Hydrocarbon Patents (Class 564/408)
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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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Patent number: 8642810Abstract: Process for the direct amination of hydrocarbons to aminohydrocarbons by reaction of a feed stream E comprising at least one hydrocarbon and at least one aminating reagent to form a reaction mixture R comprising aminohydrocarbon and hydrogen in a reaction zone RZ and electrochemical separation of at least part of the hydrogen formed in the reaction from the reaction mixture R by means of a gastight membrane-electrode assembly having at least one selectively proton-conducting membrane and at least one electrode catalyst on each side of the membrane, where at least part of the hydrogen is oxidized to protons at the anode catalyst on the retentate side of the membrane and the protons pass through the membrane and on the permeate side are reacted with oxygen to form water, where the oxygen originates from an oxygen-comprising stream O which is brought into contact with the permeate side of the membrane, over the cathode catalyst.Type: GrantFiled: July 7, 2010Date of Patent: February 4, 2014Assignee: BASF SEInventors: Petr Kubanek, Alexander Panchenko, Andreas Fischer, Thomas Heidemann
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Patent number: 8529869Abstract: The present invention relates to a hydroamination catalyst comprising boron beta zeolites, wherein the hydroamination catalyst is doped with lithium, and also a process for producing it. The present patent application further relates to a process for preparing amines by reaction of ammonia or primary or secondary amines with olefins at elevated temperatures and pressures in the presence of the hydroamination catalyst of the invention.Type: GrantFiled: April 19, 2010Date of Patent: September 10, 2013Assignee: BASF SEInventors: Thomas Heidemann, Jens Kehrer
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Publication number: 20130197178Abstract: The present invention provides novel and stable crystalline 1H-1,2,3 triazolium carbenes and metal complexes of 1H-1,2,3 triazolium carbenes. The present invention also provides methods of making 1H-1,2,3 triazolium carbenes and metal complexes of 1H-1,2,3 triazolium carbenes. The present invention also provides methods of using 1H-1,2,3 triazolium carbenes and metal complexes of 1H-1,2,3 triazolium carbenes in catalytic reactions.Type: ApplicationFiled: April 26, 2011Publication date: August 1, 2013Applicant: The Regents of the University of CaliforniaInventors: Guy Bertrand, Gregorio Gulsado-Barrios, Jean Bouffard, Bruno Donnadieu
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Publication number: 20130090445Abstract: The present invention provides a synthesis system that can synthesize aniline and/or styrene efficiently, a synthesis system that can synthesize butadiene (1,3-butadiene) efficiently, a rubber chemical for a tire which is synthesized from the aniline obtained by the synthesis system, a synthetic rubber for a tire which is synthesized from the styrene and/or butadiene obtained by the synthesis systems, and a pneumatic tire produced using the rubber chemical for a tire and/or the synthetic rubber for a tire. The present invention relates to a synthesis system for synthesizing aniline and/or styrene from an alcohol having two or more carbon atoms via an aromatic compound.Type: ApplicationFiled: January 25, 2012Publication date: April 11, 2013Applicant: SUMITOMO RUBBER INDUSTRIES, LTD.Inventors: Takayuki Hattori, Takao Wada, Keitaro Fujikura, Yuka Yokoyama, Toshiro Matsuo
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Publication number: 20120296121Abstract: 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: ApplicationFiled: May 17, 2012Publication date: November 22, 2012Applicant: BASF SEInventors: Christof Wilhelm Wigbers, Marion Kristina Brinks, Johann-Peter Melder
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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: 7838702Abstract: A process for aminating hydrocarbons with ammonia, wherein the N2 content in the mixture at the reactor exit is less than 0.1% by volume based on the total volume of the mixture at the reactor exit.Type: GrantFiled: February 13, 2007Date of Patent: November 23, 2010Assignee: BASF SEInventors: Frederik Van Laar, Ekkehard Schwab, Joachim-Thierry Anders, Sven Crone, Karl Hoelemann, Wolfgang Mackenroth, Petr Kubanek
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Patent number: 7741522Abstract: A process for aminating hydrocarbons with ammonia in the presence of catalyst (i) which catalyzes the amination, which comprises supplying oxidizing agent to the reaction mixture and reacting the oxidizing agent with hydrogen which is formed in the amination in the presence of a catalyst (ii) which catalyzes this reaction with hydrogen.Type: GrantFiled: February 15, 2007Date of Patent: June 22, 2010Assignee: BASF AktiengesellschaftInventors: Frederik Van Laar, Ekkehard Schwab, Joachim-Thierry Anders, Sven Crone, Karl Hoelemann, Wolfgang Mackenroth, Petr Kubanek
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Publication number: 20090292144Abstract: A process for aminating hydrocarbons with ammonia, which comprises performing the amination in the presence of an additive which reacts with hydrogen, the additive used being at least one organic chemical compound, N2O, hydroxylamine, hydrazine and/or carbon monoxide.Type: ApplicationFiled: July 17, 2007Publication date: November 26, 2009Applicant: BASF SEInventors: Joachim-Thierry Anders, Johann-Peter Melder, Petr Kubanek, Ekkehard Schwab, Wolfgang Mackenroth, Karl Hoelemann, Frederik Van Laar
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Publication number: 20090203941Abstract: A process for aminating hydrocarbons comprises physically removing hydrogen from the reaction mixture.Type: ApplicationFiled: August 21, 2006Publication date: August 13, 2009Applicant: BASF SEInventors: Frederik Van Laar, Ekkehard Schwab, Hartwig Voss, Joachim-Thierry Anders, Sven Crone, Wolfgang Mackenroth
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Publication number: 20090030234Abstract: A process for aminating hydrocarbons with ammonia, wherein the N2 content in the mixture at the reactor exit is less than 0.1 % by volume based on the total volume of the mixture at the reactor exit.Type: ApplicationFiled: February 13, 2007Publication date: January 29, 2009Applicant: BASF SEInventors: Frederik van Laar, Ekkehard Schwab, Joachim-Thierry Anders, Sven Crone, Karl Holemann, Wolfgang Mackenroth, Petr Kubanek
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Publication number: 20090023956Abstract: A process for aminating hydrocarbons with ammonia in the presence of catalyst (i) which catalyzes the amination, which comprises supplying oxidizing agent to the reaction mixture and reacting the oxidizing agent with hydrogen which is formed in the amination in the presence of a catalyst (ii) which catalyzes this reaction with hydrogen.Type: ApplicationFiled: February 15, 2007Publication date: January 22, 2009Applicant: BASF SEInventors: Frederik van Laar, Ekkehard Schwab, Joachim-Thierry Anders, Sven Crone, Karl Holemann, Wolfgang Mackenroth, Petr Kubanek
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Publication number: 20080146846Abstract: The invention relates to a process for preparing nitrogen-containing catalysts, comprising: a) preparation of an oxidic species comprising the following components: at least one metal M selected from groups Ib to VIIb and VIII of the Periodic Table of the Elements, it being possible for the same metal to be present in different oxidation states; if appropriate one or more promoters P selected from groups Ib to VIIb and VIII of the Periodic Table of the Elements, the lanthanides, and from groups IIIa to VIa of the Periodic Table of the Elements, excluding oxygen and sulfur; if appropriate one or more elements R selected from hydrogen, alkali metals and alkaline earth metals; if appropriate one or more elements Q selected from chloride and sulfate; oxygen, the molar proportion of oxygen being determined by the valency and frequency of the elements in the oxidic species other than other oxygen; b) reaction of the oxidic species with an amine component selected from ammonia, primary and secondary amines andType: ApplicationFiled: December 20, 2005Publication date: June 19, 2008Applicant: BASF AktiengesellschaftInventors: Harald Dialer, Matthias Frauenkron, Holger Evers, Ekkehard Schwab, Johann-Peter Melder, Frank Rosowski, Frederik Van Laar, Joachim-Thierry Anders, Sven Crone, Wolfgang Mackenroth
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Patent number: 7368610Abstract: A process for preparing xylylenediamine, comprising the steps of ammoxidizing xylene to phthalonitrile and hydrogenating the phthalonitrile, which comprises contacting the vaporous product of the ammoxidation stage directly with a liquid organic solvent or with molten phthalonitrile (quench), partly or fully removing components having a boiling point lower than phthalonitrile (low boilers) from the resulting quench solution or suspension or phthalonitrile melt and, after the low boiler removal and before the hydrogenation, removing products having a boiling point higher than phthalonitrile (high boilers).Type: GrantFiled: September 4, 2004Date of Patent: May 6, 2008Assignee: BASF AktiengesellschaftInventors: Randolf Hugo, Sabine Jourdan, Kirsten Wenz, Thomas Preiss, Alexander Weck
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Patent number: 7157606Abstract: The process for producing an amino composition of the present invention by addition reaction of a polyamine with an alkenyl group-containing compound wherein said polyamine is reacted preliminarily with a strongly basic catalyst to produce a reaction mixture comprising a reaction intermediate and then an alkenyl group-containing compound is added to the reaction mixture to proceed the addition reaction provides an amino composition having stable properties.Type: GrantFiled: August 5, 2004Date of Patent: January 2, 2007Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Masatoshi Echigo, Hisayuki Kuwahara, Takeshi Koyama
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Patent number: 7074964Abstract: In a process for preparing alkylamines by reacting olefins with ammonia, primary or secondary amines under hydroaminating conditions over a calcined zeolitic catalyst, the calcined zeolitic catalyst is thermally activated at from 100 to 550° C. in a gaseous stream of air, nitrogen, other inert gases or mixtures thereof not more than 24 hours before commencement of the reaction.Type: GrantFiled: March 23, 2004Date of Patent: July 11, 2006Assignee: BASF AktiengesellschaftInventors: Marcus Sigl, Ulrich Müller
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Patent number: 6933409Abstract: Noble metal/reducible metal oxide catalysts effective for the direct amination of aromatic hydrocarbons and heterocyclic analogs thereof are disclosed. In one embodiment, the cataloxidant comprises a noble metal selected from Pd, Rh, Ir and/or Ru and a reducible metal oxide. In another embodiment, the cataloxidant comprises a noble metal and a reducible oxide of a metal selected from Ni, Mn, V, Ce, Th, Pr, Te, Re, Co, Fe, Cu and/or Bi. A preferred cataloxidant comprises one or more noble metals selected from Pd, Rh, Ir and/or Ru, in combination with nickel oxide and/or manganese oxide. In preferred applications, benzene can be aminated in the presence of the cataloxidants to form aniline. A benzene conversion of at least 5% is achieved, with more than 90% selectivity for aniline. Significantly, the cataloxidant can be regenerated without a substantial loss of performance.Type: GrantFiled: May 15, 2000Date of Patent: August 23, 2005Assignees: Symyx Technologies, Inc., Bayer AGInventors: Damodara M. Poojary, Ramesh Borade, Alfred Hagemeyer, Xiao Ping Zhou, Christopher E. Dube, Ulrich Notheis, Ralph Armbrust, Christian Rasp, David M. Lowe
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Patent number: 6723879Abstract: Disclosed is a process for the enantioselective production of an optically active amino compound by the amination of the C—H bond of an organic compound. The amino compound is produced by converting the C—H bond at the allyl position of an alkene or the C—H bond at the benzyl position of an alkylarene to the corresponding C—N bond, using a salen-manganese complex as the catalyst and N-substituted iminoaryliodinane as the amination agent. Both the catalytic activity and the enantioselectivity are very high when there is used a catalyst in which the 3- and 5-positions of the salicylaldehyde moiety of the salen ligand are substituted with an electron-withdrawing group, particularly with a halogen atom.Type: GrantFiled: November 7, 2002Date of Patent: April 20, 2004Assignee: Japan Science and Technology CorporationInventors: Tsutomu Katsuki, Yoshinori Kohmura
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Patent number: 6583320Abstract: The invention is directed-to a method of producing one or more 4-aminodiphenylamine intermediates comprising the steps of bringing an aniline or aniline derivative and nitrobenzene into reactive contact and reacting the aniline and nitrobenzene in a confined zone at a suitable time and temperature, in the presence of a mixture comprising an inorganic salt or metal organic salt having a cation that would be a suitable cation of a strong inorganic base, an oxidant and an organic base, the mixture not including a reaction product of betaine and a strong inorganic base.Type: GrantFiled: May 10, 2002Date of Patent: June 24, 2003Assignee: Flexsys America L.P.Inventors: Ralph Dale Triplett, II, Roger Keranen Rains
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Patent number: 6562934Abstract: An amino compound obtained by addition reaction of diamine represented by the following formula (1) and an alkenyl compound and a process for producing the same. H2N—H2C—A—CH2—NH2 (1) wherein A is a phenylene group or a cyclohexylene group.Type: GrantFiled: September 10, 2001Date of Patent: May 13, 2003Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Shinichi Yonehama, Tetsushi Ichikawa
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Patent number: 6395933Abstract: The invention is directed to a method of producing one or more 4-aminodiphenylamine intermediates comprising the steps of bringing an aniline or aniline derivative and nitrobenzene into reactive contact; and reacting the aniline and nitrobenzene in a confined zone at a suitable time and temperature, in the presence of a mixture comprising a strong base and a suitable phase transfer catalyst. Certain phase transfer catalysts may also function as the strong base.Type: GrantFiled: July 23, 2001Date of Patent: May 28, 2002Assignee: Flexsys America, L.P.Inventors: Ralph Dale Triplett, II, Roger Keranen Rains
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Patent number: 6384282Abstract: The present invention is directed to a process for addition of amines to carbon-carbon double bonds in a substrate, comprising: reacting an amine with a compound containing at least one carbon-carbon double bond in the presence a transition metal catalyst under reaction conditions effective to form a product having a covalent bond between the amine and a carbon atom of the former carbon-carbon double bond. The transition metal catalyst comprises a Group 8 metal and a ligand containing one or more 2-electron donor atoms. The present invention is also directed to enantioselective reactions of amine compounds with compounds containing carbon-carbon double bonds, and a calorimetric assay to evaluate potential catalysts in these reactions.Type: GrantFiled: February 26, 2001Date of Patent: May 7, 2002Assignee: Yale UniversityInventors: John F. Hartwig, Motoi Kawatsura, Oliver Loeber
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Patent number: 6297196Abstract: Benzoyl derivatives of the formula (I), process for their preparation and their use as herbicides and plant growth regulators are described. In this formula (I), R1, R2, R3, R4 and R5 are various organic radicals, Q is isothiazole, isoxazole, cyclohexanedione or a &bgr;-ketonitrile radical and A, B, E and X are divalent units containing one or more atoms.Type: GrantFiled: September 2, 1999Date of Patent: October 2, 2001Assignee: Hoechst Schering AgrEvo GmbHInventors: Andreas Van Almsick, Lothar Willms, Thomas Auler, Hermann Bieringer, Christopher Rosinger
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Patent number: 6229035Abstract: A method for producing aromatic amines such as N-phenyl-p-phenylenediamine is disclosed wherein an amine substituted aromatic such as aniline is oxidized with oxygen or hydrogen peroxide in the presence of a preferred alkali metal pentacyano ferrate(II) complex made using water soluble ferrous salts with a non-oxidizing anion, preferably, ferrous sulfate, and containing various water soluble ligands, such as ammonia, mono alkyl amine, dialkyl amines, and trialkyl amines. The complex is subsequently catalytically reduced by hydrogenation using certain heterogeneous metal catalysts to yield the desired aromatic amine.Type: GrantFiled: June 16, 1999Date of Patent: May 8, 2001Assignee: Uniroyal Chemical Company, Inc.Inventors: Edward L. Wheeler, Mark W. Simon
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Patent number: 6204411Abstract: Process for the production of an aromatic amine by reacting an aromatic hydrocarbon with ammonia at a temperature of less than 500° C. and a pressure of less than 10 bara in the presence of a catalyst comprising at least one metal selected from the group consisting of the transition elements, lanthanides and actinides, preferably in the presence of an oxidant.Type: GrantFiled: August 21, 1998Date of Patent: March 20, 2001Assignee: Imperial Chemical Industries PLCInventors: Sean Alexander Axon, Samuel David Jackson, Peter Rene Rik Claes
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Patent number: 6143934Abstract: In a process for preparing amines of the general formula I ##STR1## where R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 are hydrogen, C.sub.1 -C.sub.20 -alkyl, C.sub.2 -C.sub.20 -alkenyl, C.sub.2 -C.sub.20 -alkynyl, C.sub.3 -C.sub.20 -cycloalkyl, C.sub.4 -C.sub.20 -alkylcycloalkyl, C.sub.4 -C.sub.20 -cycloalkylalkyl, aryl, C.sub.7 -C.sub.20 -alkylaryl or C.sub.7 -C.sub.20 -aralkyl,R.sup.1 and R.sup.2 are together a saturated or unsaturated, divalent C.sub.3 -C.sub.9 -alkylene chain andR.sup.3 and R.sup.5 are each C.sub.21 -C.sub.200 -alkyl, C.sub.21 -C.sub.200 -alkenyl or together are a divalent C.sub.2 -C.sub.12 -alkylene chain,by reacting olefins of the general formula II ##STR2## where R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are as defined above, with ammonia or primary or secondary amines of the general formula III ##STR3## where R.sup.1 and R.sup.2 are as defined above, at from 200 to 350.degree. C.Type: GrantFiled: January 20, 1998Date of Patent: November 7, 2000Assignee: BASF AktiengesellschaftInventors: Uwe Dingerdissen, Rudolf Kummer, Peter Stops, Ulrich Muller, Jurgen Herrmann, Karsten Eller
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Patent number: 6103937Abstract: A process for producing unsaturated nitrogen containing compounds such as enamides, enamines and aryl amineslamides is disclosed. A vinyl halide or aryl halide is reacted with an --NH-- containing compound in the presence of a catalytic amount of a catalyst precursor composition comprising a zero-valent nickel and an organophosphine or carbene ligand. One step coupling of vinyl halides and aryl halides with --NH-- containing compounds is made possible by practice of the invention.Type: GrantFiled: December 29, 1998Date of Patent: August 15, 2000Assignee: E. I. du Pont de Nemours and CompanyInventors: Ralph Thomas Baker, Sigridur Soley Kristjansdottir
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Patent number: 6069277Abstract: The present invention relates to a process to aminate electrophilic aromatic compounds by vicarious nucleophilic substitution of hydrogen using quaternary hydrazinium salts. The use of trialkylhydrazinium halide, e.g., trimethylhydrazinium iodide, as well as hydroxylamine, alkoxylamines, and 4-amino-1,2,4-triazole to produce aminated aromatic structures, such as 1,3-diamino-2,4,6-trinitrobenzene (DATB), 1,3,5-triamino-2,4,6-trinitrobenzene (TATB) and 3,5-diamino-2,4,6-trinitrotoluene (DATNT), is described. DATB and TATB are useful insensitive high explosives. TATB is also used for the preparation of benzenehexamine, a starting material for the synthesis of novel materials (optical imaging devices, liquid crystals, ferromagnetic compounds).Type: GrantFiled: November 12, 1997Date of Patent: May 30, 2000Assignee: The Regents of the University of CaliforniaInventors: Alexander R. Mitchell, Philip F. Pagoria, Robert D. Schmidt
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Patent number: 5977411Abstract: This invention provides a method for preparing 4-ADPA by charging nitrobenzene into a reaction zone under hydrogen pressure in the presence of a strong organic base and a catalyst for hydrogenation. The method provides the convenience and economy of a one-step process, while producing improved yields and selectivities. The invention further provides for various embodiments of the foregoing which are suitable for the production of 4-ADPA, and the hydrogenation or reductive alkylation to produce PPD. Important to the invention are the molar ratios of aniline to nitrobenzene and nitrobenzene to the strong organic base and the choice and use of hydrogenation catalyst.Type: GrantFiled: June 10, 1997Date of Patent: November 2, 1999Assignee: Flexsys America L.P.Inventor: Antonio L. DeVera
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Patent number: 5955634Abstract: A process and reagent for allylating a nucleophile preferably of formula (V).(R).sub.n Ar--Y--H (V)The nucleophile is reacted with a reagent containing an allyl derivative and a catalyst in an aqueous phase containing at least one element of group VIII of the Classification of the elements. A water-soluble phosphine may also be present in the reagent, and the reagent may also contain at least one organic phase.Type: GrantFiled: August 2, 1991Date of Patent: September 21, 1999Assignee: Rhone-Poulenc ChimieInventors: Jean-Michel Grosselin, Hubert Kempf, Jean-Pierre LeCouve
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Patent number: 5925790Abstract: A method for producing aromatic amines such as N-phenyl-p-phenylenediamine is disclosed wherein an amine substituted aromatic such as aniline is oxidized with oxygen or hydrogen peroxide in the presence of a preferred trisodium pentacyano ferrate(II) complex containing various water soluble ligands, such as ammonia, mono alkyl amine, dialkyl amines, and trialkyl amines. The complex is subsequently catalytically reduced by hydrogenation using certain heterogeneous metal catalysts to yield the desired aromatic amine.Type: GrantFiled: March 13, 1997Date of Patent: July 20, 1999Assignee: Uniroyal Chemical Company, Inc.Inventors: Edward L. Wheeler, Russell E. Malz, Jr., Mark W. Simon
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Patent number: 5900508Abstract: A process for the preparation of amines by reacting an olefin with ammonia or a primary or secondary amine at a temperature of from 200 to 350.degree. C. and a pressure of from 100 to 300 bar in the presence of at least one zeolite having the specific structure type PSH-3, MCM-22 or SSZ-25, as identified by X-ray diffractogram, or mixtures of these zeolites. These specific catalysts are broadly identified as alumina zeolites and may be modified by ion exchange, doping with other metals, by dealumination to remove or replace the alumina content and by other well known after treatments such as calcination, acid-treatment and the like. Monoolefins are preferred reactants but di- and polyolefins also can be reacted with relatively high selectivity and less tendency toward polymerization.Type: GrantFiled: July 18, 1996Date of Patent: May 4, 1999Assignee: BASF AktiengesellschaftInventors: Karsten Eller, Ulrich Muller, Rudolf Kummer, Peter Stops
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Patent number: 5861536Abstract: The present invention comprises a process for catalytic oxidative ammination of aromatic hydrocarbons which comprising contacting aromatic feedstock with oxidant, such as molecular oxygen, under suitable reaction conditions, in the presence of a catalyst comprising three essential components: a support; transition metal; and a mono- or binucleating ligand. In one embodiment of the invention the ligand comprises at least one nitro or nitroso group. In another embodiment, the ligand comprises a multidentate, chelating binuclear compound. The process is particularly suited, for example, to the one-step conversion of benzene to aniline.Type: GrantFiled: July 31, 1997Date of Patent: January 19, 1999Assignee: Sun Company, Inc. (R&M)Inventors: Vincent A. Durante, Tilak P. Wijesekera, Swati Karmakar
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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: 5773660Abstract: A process for preparing amines of the formula I ##STR1## where R.sup.1,R.sup.2,R.sup.3,R.sup.4,R.sup.5 and R.sup.6 are each hydrogen, C.sub.1 -C.sub.20 -alkyl, C.sub.2 -C.sub.20 -alkenyl, C.sub.2 -C.sub.20 -alkynyl, C.sub.3 -C.sub.20 -cycloalkyl, C.sub.4 -C.sub.20 -alkylcycloalkyl, C.sub.4 -C.sub.20 -cycloalkylalkyl, aryl, C.sub.7 -C.sub.20 -alkylaryl or C.sub.7 -C.sub.20 -aralkyl,R.sup.1 and R.sup.2 are together a saturated or unsaturated C.sub.3 -C.sub.9 -alkylene dichain, andR.sup.3 or R.sup.5 is C.sub.21 -C.sub.200 -alkyl or C.sub.21 -C.sub.200 -alkenyl or together they are a C.sub.2 -C.sub.12 -alkylene dichain,by reacting olefins of the formula II ##STR2## where R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are each as defined above, with ammonia or primary or secondary amines of the formula III ##STR3## where R.sup.1 and R.sup.2 are each as defined above, at temperatures from 200.degree. to 350.degree. C.Type: GrantFiled: January 21, 1997Date of Patent: June 30, 1998Assignee: BASF AktiengesellschaftInventors: Karsten Eller, Rudolf Kummer, Eugen Gehrer
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Patent number: 5763668Abstract: Amines are prepared by reacting a mixture obtained in the cracking of mineral oil fractions with ammonia or a primary or secondary amine of the general formula I ##STR1## where R.sup.1 and R.sup.2 are each hydrogen, C.sub.1 -C.sub.20 -alkyl, C.sub.2 -C.sub.20 -alkenyl, C.sub.2 -C.sub.20 -alkynyl, C.sub.3 -C.sub.20 -cycloalkyl, C.sub.4 -C.sub.20 -alkylcycloalkyl, C.sub.4 -C.sub.20 -cycloalkylalkyl, aryl, C.sub.7 --C.sub.20 -alkylaryl or C.sub.7 --C.sub.20 -aralkyl or together are a saturated or unsaturated C.sub.2 -C.sub.12 -alkylene ene chain,at from 200.degree. to 350.degree. C.Type: GrantFiled: July 3, 1996Date of Patent: June 9, 1998Assignee: BASF AktiengesellschaftInventors: Uwe Dingerdissen, Jurgen Herrmann, Karsten Eller
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Patent number: 5763665Abstract: In a process for the preparation of crystalline N-methylol(meth)acrylamide from (meth)acryamide and paraformaldehyde, the reaction of the solid reactants to give a product melt and the subsequent crystallization thereof in a reactor while subjecting the reaction mixture to mechanical shear load is preferably carried out in a self-purging screw reactor or a disk reactor. The reaction of the reactants and the crystallization of the product melt are preferably carried out without added solvent. A catalyst, in particular an alkali metal carbonate or a trialkylamine, can be used for the reaction of the reactants.Type: GrantFiled: January 3, 1997Date of Patent: June 9, 1998Assignee: BASF AktiengesellschaftInventors: Kaspar Bott, Thomas Domschke, Michael Bohn
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Patent number: 5739405Abstract: A process for the preparation of amines of the general formula I ##STR1## in which R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 denote hydrogen, C.sub.1 -C.sub.20 alkyl, C.sub.2 -C.sub.20 alkenyl, C.sub.2 -C.sub.20 alkynyl, C.sub.3 -C.sub.20 cycloalkyl, C.sub.4 -C.sub.20 alkylcycloalkyl, C.sub.4 -C.sub.20 cycloalkylalkyl, aryl, C.sub.7 -C.sub.20 alkylaryl, or C.sub.7 -C.sub.20 aralkyl,R.sup.1 and R.sup.2 together denote a saturated or unsaturated C.sub.3 -C.sub.9 alkylene dichain andR.sup.3 or R.sup.5 denotes C.sub.21 -C.sub.200 alkyl, C.sub.21 -C.sub.200 alkenyl or they together form a C.sub.2 -C.sub.12 alkylene dichain,by the reaction of olefins of the general formula II ##STR2## in which R.sup.3, R.sup.4, R.sup.5, and R.sup.6 have the above meanings, with ammonia or primary or secondary amines of the general formula III ##STR3## in which R.sup.1 and R.sup.2 have the above meanings, at temperatures ranging from 200.degree. to 350.degree. C.Type: GrantFiled: December 4, 1996Date of Patent: April 14, 1998Assignee: BASF AktiengesellschaftInventors: Karsten Eller, Rudolf Kummer, Peter Stops
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Patent number: 5739403Abstract: 4-Aminodiphenylamines are produced by reacting optionally substituted aniline with optionally substituted nitrobenzene in the presence of water and/or alcohols and organic and/or inorganic bases and then catalytically hydrogenating the resultant nitro- and/or nitrosodiphenylamine in the presence of water, wherein the catalytic hydrogenation of the reaction mixture is performed in the presence of 25 to 80 wt. % of water, relative to the weight of the reaction mixture from the condensation reaction, the hydrogenation catalyst is removed from the hydrogenation mixture once absorption of hydrogen has ceased, 10 to 100 vol. % of aromatic solvent, relative to the total volume of the hydrogenation mixture, are optionally added to the hydrogenation mixture, the resultant organic phase is separated in order to isolate the 4-aminodiphenylamine and the aqueous phase is returned to the initial reaction mixture.Type: GrantFiled: January 6, 1997Date of Patent: April 14, 1998Assignee: Bayer AGInventors: Klaus Reinartz, Adolf Brill, Fred Schuhmacher
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Patent number: 5739397Abstract: Secondary amines having a hydrocarbon backbone, a functionality of at least 1 and a molecular weight of at least 74 are produced by reacting a hydrocarbon containing a leaving group with a primary amine, primary diamine, primary polyamine or ammonia at a temperature of from about 70.degree. to 250.degree. C.Type: GrantFiled: May 30, 1996Date of Patent: April 14, 1998Assignee: Bayer CorporationInventors: Rick L. Adkins, William E. Slack
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Patent number: 5728882Abstract: A method for producing aromatic amines such as N-phenyl-p-phenylenediamine is disclosed wherein an amine substituted aromatic such as aniline is oxidized with oxygen or hydrogen peroxide in the presence of trisodium pentacyano ferrate(II) complexes containing various water soluble ligands, such as ammonia, mono alkyl amine, dialkyl amines, and trialkyl amines. The complex is subsequently catalytically reduced by hydrogenation using certain heterogeneous metal catalysts to yield the desired aromatic amine.Type: GrantFiled: April 4, 1996Date of Patent: March 17, 1998Assignee: Uniroyal Chemical Company, Inc.Inventors: Edward Lockwood Wheeler, Russell Edward Malz, Jr.
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Patent number: 5723670Abstract: Amines which are solid at ambient temperature and pressure are liquified by reacting those amines with a derivatizing agent represented by the formula XY in which X represents a halide or sulfonate group and Y represents an alkyl group, a cycloalkyl group, an alkoxyalkyl group or an aryl group. The amine and derivatizing agent are reacted at temperatures of from about 50.degree. to about 250.degree. C. in amounts such that the molar ratio of derivatizing agent to amine groups is from about 0.25:1 to 8:1.Type: GrantFiled: June 18, 1996Date of Patent: March 3, 1998Assignee: Bayer CorporationInventors: Rick L. Adkins, William E. Slack
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Patent number: 5633407Abstract: A process for preparing substituted aromatic azo compounds is provided which comprises contacting a nucleophilic compound and an azo containing compound in the presence of a suitable solvent system, and reacting the nucleophilic compound and the azo containing compound in the presence of a suitable base and a controlled amount of protic material at a temperature of about 10.degree. C. to about 150.degree. C. in a confined reaction zone wherein the molar ratio of protic material to base is 0:1 to about 5:1. In another embodiment, the substituted aromatic azo compounds are further reacted with a nucleophilic compound in the presence of a suitable solvent system, a suitable base and a controlled amount of protic material at a temperature of about 70.degree. C. to about 200.degree. C. in a confined reaction zone wherein the molar ratio of protic material to base is 0:1 to about 5:1 to produce a substituted aromatic amine.Type: GrantFiled: May 18, 1995Date of Patent: May 27, 1997Assignee: Flexsys America L. P.Inventors: Michael K. Stern, Brian K-M Cheng
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Patent number: 5633406Abstract: The present invention relates to a process to produce 1,3-diamino-2,4,6-trinitrobenzene (DATB) or 1,3,5-triamino-2,4,6,-trinitrobenzene (TATB) by:(a) reacting at ambient pressure and a temperature of between about 0.degree. and 50.degree. C. for between about 0.1 and 24 hr, a trinitroaromatic compound of structure V: ##STR1## wherein X, Y, and Z are each independently selected from the group consisting of --H and --NH.sub.Type: GrantFiled: May 12, 1995Date of Patent: May 27, 1997Assignee: The Regents of the University of CaliforniaInventors: Alexander R. Mitchell, Philip F. Pagoria, Robert D. Schmidt
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Patent number: 5618979Abstract: A process for preparing substituted aromatic amines which comprises contacting a nucleophilic compound and a substituted aromatic azo compound in the presence of a suitable solvent system, and reacting the nucleophilic compound and the substituted aromatic azo compound in the presence of a suitable base and a controlled amount of protic material at a temperature of about 70.degree. C. to about 200.degree. C. in a confined reaction zone wherein the molar ratio of protic material to base is 0:1 to about 5:1. In another embodiment, the substituted aromatic amines of the invention are reductively alkylated to produce alkylated diamines or substituted derivatives thereof.Type: GrantFiled: May 18, 1995Date of Patent: April 8, 1997Assignee: Flexsys America L. P.Inventors: Michael K. Stern, Brian K-M Cheng
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Patent number: 5612483Abstract: Nitro-substituted aromatics can be directly aminated with amines in the presence of simple bases and oxygen.Type: GrantFiled: September 6, 1995Date of Patent: March 18, 1997Assignee: Bayer AktiengesellschaftInventor: Manfred Jautelat
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Patent number: 5608111Abstract: A method of producing 4-ADPA is disclosed wherein aniline or substituted aniline derivatives and nitrobenzene are reacted under suitable conditions to produce 4-nitrodiphenylamine or substituted derivatives thereof and/or 4-nitrosodiphenylamine or substituted derivatives thereof and/or their salts, either or both of which are subsequently reduced to produce 4-ADPA or substituted derivatives thereof. The 4-ADPA or substituted derivatives thereof can be reductively alkylated to produce p-phenylenediamine products or substituted derivatives thereof which are useful as antiozonants.Type: GrantFiled: May 5, 1995Date of Patent: March 4, 1997Assignee: Flexsys America L. P.Inventors: Michael K. Stern, James M. Allman, James K. Bashkin, Roger K. Rains
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Patent number: 5587516Abstract: An electrophotographic photoconductor comprises an electroconductive substrate and a photoconductive layer formed thereon comprising as an effective component at least one pyrenylamine derivative of formula (I): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, W, j, k, l, m and n are specifically defined in the specification. Furthermore, a novel pyrenylamine derivative for use in the above electrophotographic photoconductor, an aldehyde compound, which is an intermediate for producing the pyrenylamine derivative, and methods of preparing the pyrenylamine derivative and the aldehyde compound are disclosed.Type: GrantFiled: June 5, 1995Date of Patent: December 24, 1996Assignee: Ricoh Company, Ltd.Inventors: Chiaki Tanaka, Masaomi Sasaki, Tamotsu Aruga, Tomoyuki Shimada, Hiroshi Adachi
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Patent number: 5545388Abstract: Methods for synthesis of chemical compounds by catalytic transfer hydrogenation comprise forming a mixture of a starting material, a hydrogen donor material and a catalyst. The catalyst is selected from a catalytic form of carbon, a polyethylene glycol phase transfer agent, and mixtures thereof. The mixture is heated at a temperature of from 30.degree. to 400.degree. C. in the presence of at least one alkali or alkaline earth metal compound to cause reduction of the starting material by catalytic transfer hydrogenation and form the desired chemical compound product.Type: GrantFiled: March 29, 1995Date of Patent: August 13, 1996Inventors: Charles J. Rogers, Alfred Kornel