Nitro Bonded Directly To Benzene Ring Patents (Class 568/939)
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Publication number: 20090005615Abstract: A method for producing nitrobenzene is disclosed which comprises forming a dispersion comprising benzene-containing droplets or particles dispersed in a mixture of concentrated nitric acid and concentrated sulfuric acid, wherein said particles have a mean diameter less than one micron, and subjecting the dispersion to reaction conditions comprising a pressure in the range of about 203 kPa (2 atm) to about 6080 kPa (60 atm) and a temperature in the range of about 20° C. to about 230° C., whereby at least a portion of said benzene is nitrated to form nitrobenzene. A system for carrying out the method is also disclosed.Type: ApplicationFiled: June 13, 2008Publication date: January 1, 2009Applicant: H R D CORPORATIONInventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
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Patent number: 7326816Abstract: Nitrobenzene is produced and then purified using an acidic wash, an alkaline wash, a neutral wash, subjecting a dispersion formed in the neutral wash to electrophoresis to separate water and benzene from the nitrobenzene and recover purified nitrobenzene.Type: GrantFiled: January 30, 2007Date of Patent: February 5, 2008Assignee: Bayer MaterialScience AGInventors: Thomas Knauf, Franz-Ulrich Von Gehlen, Jörg Schmiedler, Klaus Pilarczyk, Peter Drinda
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Patent number: 6953869Abstract: The present invention relates to a process for working up organic secondary components which are formed in the one-stage or two-stage nitration of toluene to dinitrotoluene. These organic secondary components are present in the acidic and alkaline waste water from the dinitrotoluene washing step and in the aqueous distillate from the sulfuric acid concentration step, together with small amounts of mononitrotoluene and dinitrotoluene. This process comprises a) combining the acidic and alkaline waste waters from the washing step and the aqueous distillate from the sulfuric acid concentration step such that the resulting mixture has a pH below 5, b) separating the aqueous and organic phases which form by phase separation, and c) recycling the organic phase from step b) into the nitration process.Type: GrantFiled: June 28, 2004Date of Patent: October 11, 2005Assignee: Bayer MaterialScience AGInventors: Jürgen Münnig, Dietmar Wastian, Wolfgang Lorenz, Berthold Keggenhoff
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Patent number: 6936741Abstract: The present invention relates to a process for working up or treating aqueous waste waters which are formed during the nitration of toluene to dinitrotoluene with nitrating acid. These aqueous waste waters containing acidic wash water and alkaline wash water from the dinitrotoluene washing step, and distillate from the sulfuric acid concentration step. The process comprises, a) combining the acidic and alkaline waste waters from the washing step and the aqueous distillate from the sulfuric acid concentration step such that the resulting mixture has a pH below 5, b) separating the aqueous and organic phases which are formed by phase separation, c) subjecting the aqueous phase from b) to an extraction step, wherein d) the organic components contained in the aqueous phase from c) are extracted with toluene, and e) introducing the toluene phase enriched with the organic components into the toluene nitration.Type: GrantFiled: June 28, 2004Date of Patent: August 30, 2005Assignee: Bayer MaterialScience AGInventors: Jürgen Münnig, Dietmar Wastian, Wolfgang Lorenz, Berthold Keggenhoff
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Patent number: 6906231Abstract: A process for the nitration of an aromatic compound, wherein the aromatic compound is admixed with a nitrating agent in the presence of an ionic liquid is described. The method for the nitration of aromatic compounds in (e.g. neutral) ionic liquids has advantages over conventional nitrations, such as the only by-product being water, the ionic liquid not being consumed and the nitrating agent being relatively inexpensive.Type: GrantFiled: October 5, 2001Date of Patent: June 14, 2005Assignee: The Queen's University of BelfastInventors: Martyn John Earle, Suhas Prabhakar Katdare
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Patent number: 6791000Abstract: Nitration of benzene is an important reaction for the production of nitro benzene, which is an important intermediate in chemical and pharmaceutical industries. Conventionally nitrobenzene is produced by liquid phase reactions employing mixed acids. A sulfuric acid/nitric acid mixture is the most commonly used nitrating agent. Generation of large amount dilute sulfuric acid, organic wastes and products of their neutralization makes the benzene nitration a environmentally harmful process. The present process enables the preparation of nitrobenzene by vapor phase nitration of benzene over solid acid catalyst, MoO3/SiO2 using nitric acid. This process is a clean and environment friendly process without use of sulphuric acid.Type: GrantFiled: May 30, 2003Date of Patent: September 14, 2004Assignee: Council of Scientific and Industrial ResearchInventors: Mohan Keraba Dongare, Pratap Tukaram Patil, Kusum Madhukar Malshe
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Patent number: 6768032Abstract: The present invention relates to a continuous isothermal process for preparing mononitrotoluenes in the presence of a mixed acid component comprising mixtures of sulfuric acid and phosphoric acid with concentration of the resultant waste acid and recycling of the concentrated waste acid to the process.Type: GrantFiled: April 2, 2002Date of Patent: July 27, 2004Assignee: Bayer Chemicals AGInventors: Matthias Gotta, Ralf Demuth, Eberhard Zirngiebl, Hans-Martin Weber, Georg Ronge
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Patent number: 6756504Abstract: The invention relates to compounds of the general formula (I), as defined, and to pharmaceutical compositions containing them. The compounds of formula (I) are inhibitors of various lipid-related enzymes. They can be used in reducing accumulation of sphingolipids and thus in the treatment of lipid storage diseases. The compounds of formula (I) can also be used for the treatment of cancerous diseases and for killing of wild type and drug-resistant cancer cells.Type: GrantFiled: October 17, 2002Date of Patent: June 29, 2004Assignee: Yissum Research Development Company of the Hebrew University of JerusalemInventors: Arieh Dagan, Shimon Gatt
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Patent number: 6703532Abstract: This invention relates to a process for the nitration of xylene isomers by using zeolite-beta as a catalyst. This invention particularly relates to a process for the nitration of xylenes using solid acid catalyst, thus totally eliminating the disposal of spent acid and salts. Herein we describe the nitration of disubstituted benzenes, all the isomers of xylene, by employing nitric acid and beta zeolite catalyst dispensing the use of acetic anhydride.Type: GrantFiled: December 21, 2001Date of Patent: March 9, 2004Assignee: Council of Scientific and Industrial ResearchInventors: Boyapati Manoranjan Choudary, Mannepalli Lakshmi Kantam, Nadakuditi Sailendra Kumar, Kompella Vishweshwara Ram Prasad, Kondapuram Vijaya Raghavan
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Publication number: 20040024267Abstract: Nitration of benzene is an important reaction for the production of nitro benzene, which is an important intermediate in chemical and pharmaceutical industries. Conventionally nitrobenzene is produced by liquid phase reactions employing mixed acids. A sulfuric acid/nitric acid mixture is the most commonly used nitrating agent. Generation of large amount dilute sulfuric acid, organic wastes and products of their neutralization makes the benzene nitration a environmentally harmful process. The present process enables the preparation of nitrobenzene by vapor phase nitration of benzene over solid acid catalyst, MoO3/SiO2 using nitric acid. This process is a clean and environment friendly process without use of sulphuric acid.Type: ApplicationFiled: May 30, 2003Publication date: February 5, 2004Applicant: COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCHInventors: Mohan Keraba Dongare, Pratap Tukaram Patil, Kusum Madhukar Malshe
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Patent number: 6583327Abstract: The present invention relates to a process for the continuous isothermal preparation of mononitrotoluenes with concentration of the resultant waste sulfuric acid and recycling of the concentrated waste sulfuric acid to the process.Type: GrantFiled: October 26, 2001Date of Patent: June 24, 2003Assignee: Bayer AktiengesellschaftInventors: Ralf Demuth, Frank Döbert, Harald Petersen, Georg Ronge, Hans-Martin Weber, Thomas Würminghausen, Eberhard Zirngiebl
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Publication number: 20030055300Abstract: The invention relates to an optimized tubular reactor for adiabatically mononitrating aromatics, halogenated aromatics and halogenated hydrocarbons, which tubular reactor is divided into from 4 to 12 chambers by plates which have openings and effect a pressure drop of from 0.5 to 4 bar per plate.Type: ApplicationFiled: September 6, 2002Publication date: March 20, 2003Inventors: Andreas Chrisochoou, Ralf DeMuth, Thomas Linn, Paul Wagner, Knud Werner
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Patent number: 6515190Abstract: Porous microcomposites have been prepared from perfluorinated ion-exchange polymer and metal oxides such as silica using the sol-gel process. Such microcomposites possess high surface area and exhibit extremely high catalytic activity.Type: GrantFiled: September 27, 2000Date of Patent: February 4, 2003Assignee: E. I. du Pont de Nemours and CompanyInventors: Mark Andrew Harmer, Qun Sun
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Patent number: 6515189Abstract: A method of reacting an aromatic compound with an immiscible reacting agent involves the passage of the reactant along a flow path having a width of from 10 to 1000 &mgr;m in such a way that essentially laminar flow of the reactant takes place. Reaction takes place across the interface between the phases and without substantial mixing of the unreacted aromatic compound and the reacting agents. A preferred reaction is the nitration reaction which involves reaction of a first phase comprising an organic aromatic compound on a second phase comprising a nitrating agent to produce two new phases of different chemical composition to the starting phases. The aqueous and organic phases produced are ideally separated such that minimum contamination occurs. Other examples of this type of reaction include the sulphonation of an aromatic compound using sulphuric acid as the sulphonating agent. The aromatic compound is slowly consumed in the reaction yielding a single aqueous phase.Type: GrantFiled: February 5, 2001Date of Patent: February 4, 2003Assignee: British Nuclear Fuels PLCInventors: Paul Harston, John Burns, Colin Ramshaw
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Patent number: 6506948Abstract: This invention relates to an improvement in a process for the production of dinitrotoluene and particularly to the recovery of dinitrotoluene and organic by-products from the wastewater and wash waters generated in the process. Wastewater and wash water streams contaminated with residual levels of mononitrotoluene, dinitrotoluene, and organic by-products, formed in the purification process, are contacted with toluene. An organic phase and an aqueous phase are generated. The phases are separated and the dinitrotoluene recovered from the organic phase.Type: GrantFiled: February 7, 2002Date of Patent: January 14, 2003Assignee: Air Products and Chemicals, Inc.Inventor: John Edward Sawicki
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Patent number: 6506949Abstract: A tubular reactor characterized by having short static mixing elements separated by coalescing zones is used to conduct multiphase liquid/liquid reactions. Small droplets of one of the phases are dispersed into the other phase by the static mixing elements. These droplets coalesce and at least partially phase separate as the mixture passes through the subsequent coalescing zone. The tubular reactor is particularly suitable for nitrating organic compounds while forming low levels of improperly nitrated by-products and low levels of nitrophenolics.Type: GrantFiled: March 1, 2001Date of Patent: January 14, 2003Assignee: Dow Global Technologies, Inc.Inventors: Paul A. Gillis, Helge Braun, Joerg Schmidt, Jan Willem Verwijs, Harald Velten, Kristina Platkowski
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Patent number: 6362381Abstract: Aromatic hydrocarbons are nitrated by a process in which the aromatic hydrocarbon is reacted in the liquid phase with an oxide of nitrogen selected from NO, N2O3, NO2 and N2O4 and with an oxygen-containing gas stream in the presence of a heterogeneous oxidic catalyst, wherein at least 0.1 mol %, based on the aromatic hydrocarbon, of water is present at the beginning of the reaction.Type: GrantFiled: September 6, 2001Date of Patent: March 26, 2002Assignee: BASF AktiengesellschaftInventors: Matthias Eiermann, Klaus Ebel
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Patent number: 6329529Abstract: Disclosed are a fluorinating agent represented by the general formula (1): wherein R1 to R4 are a substituted or unsubstituted, saturated or unsaturated alkyl group or a substituted or unsubstituted aryl group, and can be the same or different; R1 and R2 or R3 and R4 can bond to form a ring including a nitrogen atom or a nitrogen atom and other hetero atoms; or R1 and R3 can bond to form a ring including a nitrogen atom or a nitrogen atom and other hetero atoms, for example: a preparation process of the fluorinating agent and a process for preparing fluorine compounds by reacting various compounds with the fluorinating agent. The invention has also disclosed that the fluorinating agent is very effective for fluorinating oxygen containing functional compounds.Type: GrantFiled: July 31, 1998Date of Patent: December 11, 2001Assignee: Mitsui Chemicals, Inc.Inventors: Hiroshi Sonoda, Kazunari Okada, Akira Takahashi, Kouki Fukumura, Hidetoshi Hayashi, Teruyuki Nagata, Yasuhiro Takano
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Patent number: 6316675Abstract: A process for the synthesis of olefins having aromatic substituents is described in which olefins are reacted with aryl halides in the presence of catalysts consisting of palladium compounds and tetraaryl phosphonium salts.Type: GrantFiled: September 23, 1999Date of Patent: November 13, 2001Assignee: Studiengesellschaft Kohle mbHInventors: Manfred T. Reetz, Gunther Lohmer, Renate Lohmer
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Patent number: 6303820Abstract: The invention relates to a process for the preparation of nitrosobenzenes from aromatic amines by oxidation with hydrogen peroxide in the presence of sodium molybdate dihydrate and an inert organic solvent.Type: GrantFiled: November 6, 2000Date of Patent: October 16, 2001Assignee: Bayer AktiengesellschaftInventors: Henry Giera, Walter Lange, Michaela Meiers, Raul Pires
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Patent number: 6291726Abstract: The nitration of aromatic compounds is achieved in high yield and selectivity by using oxygen activated by an inorganic catalyst and nitrogen dioxide. Since this process uses neither concentration nitric nor sulfuric acids, the generation of spent waste acid does not occur. Furthermore, the process does not encounter the problem of high costs associated with the generation of ozone as in an alternative nitration process. Since the solubility of oxygen in a reaction medium is increased by using pressurized oxygen, nitrogen dioxide is activated by a porous inorganic oxide and thus an aromatic compound(e.g., benzene) is nitrated into a nitro compound (e.g., PhNO2), the reaction rate is significantly increased, and the recovery of reactants is easy due to the insolubility of the catalyst.Type: GrantFiled: October 18, 2000Date of Patent: September 18, 2001Assignee: Inha University FoundationInventors: Bon-Su Lee, Kyoo-Hyun Chung, Yoon-Sik Lee, Young-Gyu Kim
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Patent number: 6284894Abstract: A process for the preparation of an allylic aromatic compound in which an aromatic amine is reacted first with a nitrite and then with an allylic olefin having an eliminatable terminal substituent. Novel allylic derivatives of disubstituted benzene compounds are also described.Type: GrantFiled: December 17, 1999Date of Patent: September 4, 2001Assignee: Nycomed Imaging ASInventors: Fredrik Ek, Lars Goran Wistrand
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Patent number: 6274775Abstract: The invention relates to a process for the preparation of nitrosobenzene from aromatic amines by oxidation with hydrogen peroxide in the presence of a catalyst based on compounds of tungsten and/or molybdenum without the addition of the organic solvents conventionally used.Type: GrantFiled: November 6, 2000Date of Patent: August 14, 2001Assignee: Bayer AktiengesellschaftInventors: Henry Giera, Michaela Meiers, Uwe Hugger
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Patent number: 6242657Abstract: In the reaction of aromatic compounds with nitrating acids comprising HNO3 and, if appropriate, H2SO4 and/or H2O and/or H3PO4 to form aromatic nitro compounds, according to the invention an amount of from 0.5 to 20,000 ppm of one or more surface-active substances from the group of the anionic, cationic, zwitterionic or nonionic surface-active substances is added to the reaction mixture.Type: GrantFiled: April 26, 2000Date of Patent: June 5, 2001Assignee: Bayer AktiengesellschaftInventors: Bernd-Michael König, Johannes Dühr, Hans-Joachim Raatz, Manfred Kaczorowski
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Patent number: 6127583Abstract: A preparation process of an acetylene derivative comprising reacting a compound having a skeleton represented by the formula (1): ##STR1## in the molecular formula with a compound represented by the formula (2): ##STR2## wherein R.sup.1, R.sup.2 R.sup.3 and R.sup.4 are individually an alkyl group having 1 to 6 carbon atoms and can be the same or different, R.sup.1 and R.sup.3 can bond each other to form a ring, and R.sup.1 and R.sup.2 or R.sup.3 and R.sup.4 can be bond each other to form one or two heterocyclic rings: or with a compound represented by the formula (3): wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are the same as in the formula (2), and X.sub.1 is a ##STR3## chlorine, bromine or iodine atom.Type: GrantFiled: March 31, 1999Date of Patent: October 3, 2000Assignee: Mitsui Chemicals, Inc.Inventors: Hiroshi Sonoda, Kazunari Okada, Kenichi Goto, Kouki Fukumura, Junko Naruse, Hidetoshi Hayashi, Teruyuki Nagata, Akira Takahashi
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Patent number: 5998661Abstract: A process for selective, direct oxidation of amine or amine hydrochloride mpounds is described. It uses mixed oxidizing agents of monopersulfate and ozone.Type: GrantFiled: June 15, 1998Date of Patent: December 7, 1999Assignee: The United States of America as represented by the Secretary of the ArmyInventor: Abdollah Bashir-Hashemi
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Patent number: 5963878Abstract: A continuous process to nitrate a nitratable aromatic compound utilizing nitric acid and sulfuric acid feed stocks is described. The process includes the collecting of NO.sub.x O gases with water under pressure to and treating the NO.sub.x gases with water under pressure to produce weak nitric acid which is recycled to the nitric acid feed stock. The process is efficient, permitting the venting of NO.sub.x free gases to the atmosphere.Type: GrantFiled: July 30, 1998Date of Patent: October 5, 1999Assignee: Noram Engineering & Constructors Ltd.Inventors: Clive M. H. Brereton, Alfred A. Guenkel
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Patent number: 5952531Abstract: A process for the nitration of an aromatic or heteroaromatic compound with a nitrating agent comprising nitric acid or a mixture of nitric and sulphuric acids, characterised in that nitration is performed in a solvent comprising at least 50% v/v of a C.sub.1 -C.sub.6 alkyl ester of a C.sub.1 -C.sub.4 carboxylic acid. The process is of particular use for the nitration of diphenyl ethers to give compounds which are useful as herbicides or as intermediates in the synthesis of herbicides.Type: GrantFiled: October 30, 1997Date of Patent: September 14, 1999Assignee: Zeneca LimitedInventors: Ian Jeffrey Grassham Priestley, James Peter Muxworthy, John Heathcote Atherton, Martin Lennon, Stephen Martin Brown
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Patent number: 5886240Abstract: The invention relates to a process for preparing aromatic acetylenes of the formula (I): Ar--C.tbd.C--R.sup.8a, where Ar is: ##STR1## by reacting haloaromatics or aryl sulfonates of the formula (II): Ar--X, with monosubstituted acetylenes of the formula (III): Ar--C.tbd.C--R.sup.8a, where Ar is defined above and X is bromine, chlorine or OSO.sub.2 R, in the presence of a palladium compound catalyst of the formula (IV): ##STR2## where R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6 are, independently of one another, hydrogen (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-alkoxy, fluorine, NH.sub.2, NH-alkyl-(C.sub.1 -C.sub.4), N(alkyl).sub.2 -(C.sub.1 -C.sub.4), CO.sub.2 -alkyl-(C.sub.1 -C.sub.4), OCO-alkyl-(C.sub.1 -C.sub.4), or phenyl, or R.sup.1 and R.sup.2, R.sup.2 and R.sup.3, R.sup.3 and R.sup.4, R.sup.5 and R.sup.6, together form an aliphatic or aromatic ring, and R.sup.7, R.sup.8 are (C.sub.1 -C.sub.8)-alkyl, (C.sub.3 -C.sub.Type: GrantFiled: April 26, 1996Date of Patent: March 23, 1999Assignee: Hoechst AktiengesellschaftInventors: Matthias Beller, Claus Peter Reisinger, Wolfgang Anton Herrmann
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Patent number: 5847240Abstract: A process is disclosed for removing a light organic compound from a liquid composition comprising said light organic compound in admixture with a nitroaromatic compound, said light organic compound having a partial vapor pressure in said composition that is greater than the partial vapor pressure of said nitroaromatic compound in said composition, said process comprising contacting said composition with steam or a gas to cause at least a portion of said light organic compound to pass out of said composition and into admixture with said steam or gas.Type: GrantFiled: March 24, 1997Date of Patent: December 8, 1998Assignee: Arco Chemical Technology, L.P.Inventors: Allen B. Quakenbush, Buford T. Pennington
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Patent number: 5763697Abstract: The selective introduction of a nitro group into an aromatic compound by mixtures of nitric acid and sulphuric acid, wherein the aromatic compound to be nitrated is conveyed to a central driving jet of the acid mixture in such a way that it surrounds the mixed acid jet.Type: GrantFiled: May 16, 1996Date of Patent: June 9, 1998Assignee: Josef Meissner GmbH & Co.Inventors: Heinrich Hermann, Jurgen Gebauer
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Patent number: 5728901Abstract: A process for preparing a nitrated arene which comprises reacting an arene and nitric acid in the presence of a water tolerant Lewis acid catalyst under process conditions sufficient to form the nitrated arene and recovering the nitrated arene. Suitable Lewis acid catalysts are represented by the formula M.sup.n (A.sub.1).sub.x (A.sub.2).sub.n-x whereinM is selected from the group consisting of La, Pr, Nd, Sm, Eu, Gd, Dy, Ho, Er, Tm, Yb, Sc, Hf, Lu and Li;A.sub.1 and A.sub.2 are independently selected from a perfluoroalkylsulfonate, a fluorosulfonate, a hexafluorophosphate or a nitrate;n is the common oxidation state of M andx is 1, 2, 3 or 4 with the proviso that x is never greater than n.The catalysts of the process are isolatable from water and can be recycled for subsequent process cycles.Type: GrantFiled: October 4, 1996Date of Patent: March 17, 1998Assignee: Air Products and Chemicals, Inc.Inventors: Dorai Ramprasad, Francis Joseph Waller, Anthony Gerard Barrett, David Christopher Braddock
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Patent number: 5648565Abstract: Mononitrotoluenes can be prepared by intensively mixing together toluene, nitric acid, sulphuric acid and water, simultaneously or successively in their total amount, and, in the case of continuous preparation, redispersing the mixture at least twice, for which purpose a mixing energy of 1 to 40 watts per liter of the total reaction mixture, preferably 3 to 30 W/l, is employed per volume of the reactor, and, for the continuous procedure, the back mixing is substantially repressed. Adiabatic reaction conditions are maintained.Type: GrantFiled: July 12, 1996Date of Patent: July 15, 1997Assignee: Bayer AktiengesellschaftInventors: Bernd-Michael Konig, Helmut Judat, Heinz Ulrich Blank
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Patent number: 5488187Abstract: Aromatic nitration reactions and, more specifically, a process for nitrating benzene to produce dinitrobenzene or mononitrobenzene in the absence of sulfuric acid and in the absence of any dipolar aprotic solvent.Type: GrantFiled: August 15, 1994Date of Patent: January 30, 1996Assignee: Olin CorporationInventor: Robert W. Mason
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Patent number: 5399773Abstract: Nitrophenyl alkyl ethers can be advantageously prepared by reacting a nitrophenol with an alkyl halide in water as the reaction medium in such a manner that the nitrophenol is laid before with the water and the alkyl halide and a hydrogen halide-binding compound are then added simultaneously.Type: GrantFiled: June 5, 1992Date of Patent: March 21, 1995Assignee: Bayer AktiengesellschaftInventors: Bernhard Beitzke, Robert Weitz
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Patent number: 5395995Abstract: A process for the preparation and purification of nitroaromatics by nitration of the corresponding aromatics and subsequent melt crystallization. The residual melts which occur are recycled.Type: GrantFiled: May 10, 1993Date of Patent: March 7, 1995Assignee: Bayer AktiengesellschaftInventors: Dieter Grenner, Thomas Schieb, Gerhard Wiechers
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Patent number: 5329054Abstract: Activated carboxylic acids and esters such as pentafluorobenzoic acid are rapidly decarboxylated in high yields by reacting the acid or ester with an alkanolamine reagent which catalyzes the reaction.Type: GrantFiled: July 19, 1993Date of Patent: July 12, 1994Assignee: Albemarle CorporationInventors: Kevin J. Theriot, Niomi L. Krzystowczyk, Yueh-Dong Chen, Edward A. Burt, Lawrence H. Shepherd, Jr.
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Patent number: 5315043Abstract: A process for halogen exchange fluorination or fluoro-denitration of aromatic compounds having at least one replaceable non-fluorine halogen or nitro substituent with an anhydrous substantially molten alkali metal acid fluoride composition wherein the alkali metal is potassium, rubidium or cesium.Type: GrantFiled: February 5, 1992Date of Patent: May 24, 1994Assignee: E. I. Du Pont de Nemours and CompanyInventors: Richard E. Fernandez, Mark H. Krackov
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Patent number: 5313009Abstract: A continuous process to nitrate a nitratable aromatic compound in a nitronium ion solution in a nitrator. The process comprises feeding into the nitrator nitronium ion solution of a composition within an area defined by connecting three points in a ternary phase diagram of nitric acid, sulfuric acid and water. The three points correspond to first about 82% of sulfuric acid and 18% nitric acid, secondly about 55% sulfuric acid and about 45% water and, thirdly, 100% sulfuric acid, with the nitric acid preferably being below about 3%. The nitratable aromatic compound is introduced in a manner such that a fine emulsion of hydrocarbon in the nitronium ion solution is formed with the hydrocarbon evenly distributed in the acid phase. The acid and the nitratable aromatic compound are brought into intimate contact in a plug-flow nitrator that contains mixing elements.Type: GrantFiled: October 14, 1993Date of Patent: May 17, 1994Assignee: NRM International Technologies C.V.Inventors: Alfred A. Guenkel, John M. Rae, Edward G. Hauptmann
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Patent number: 5270309Abstract: 4-Oxo-1,4-dihydroquinoline compounds having a 2-acidic group or a group convertible thereto in vivo, and their pharmaceutically acceptable salts, are potent specific antagonists of N-methyl-D-aspartate (NMDA) receptors and are therefore useful in the treatment of neurodegenerative disorders. 4-Oxo-1,4-dihydroquinoline compounds having a 2-acidic group or a group convertible thereto in vivo, other than carboxy or C.sub.1-6 alkoxycarbonyl, are novel compounds, as also are compounds of formula II ##STR1## wherein R.sup.2 represents carboxy or a group convertible thereto in vivo, R.sup.6 is hydrogen and R.sup.5 and R.sup.7 represent C.sub.1-6 alkyl or halogen, provided that R.sup.5 and R.sup.7 are not simultaneously chlorine or simultaneously bromine; a process for preparing the novel compounds is described, as also are pharmaceutical compositions containing the novel compounds.Type: GrantFiled: July 20, 1992Date of Patent: December 14, 1993Assignee: Merck Sharp & Dohme LimitedInventor: Paul Leeson
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Patent number: 5247124Abstract: A process for preparing a substituted styrene by reacting a bisarylalkyl ether in the presence of an acid catalyst is disclosed. The process is preferably used for the preparation of 4-acetoxystyrene from 4,4'-(oxydiethylidene)bisphenol diacetate and 4-methoxystyrene from 4,4'-(oxydiethylidene)bisphenol dimethyl ether. A process for preparing a bisarylalkyl ether by reacting a corresponding arylalkanol in the presence of an acid catalyst is also disclosed.Type: GrantFiled: August 25, 1992Date of Patent: September 21, 1993Assignee: Hoechst Celanese CorporationInventors: Mohammad Aslam, Brad L. Smith, George Kvakovszky
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Patent number: 5245092Abstract: Process for preparing dinitrotoluene by reacting toluene with concentrated nitric acid. The process reacts toluene with a large excess of concentrated nitric acid at selected conditions to produce a product which has substantially reduced by-product content.Type: GrantFiled: September 14, 1992Date of Patent: September 14, 1993Assignee: Olin CorporationInventor: Allen B. Quakenbush
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Patent number: 5237077Abstract: The present invention relates to a process for producing an aromatic nitro compound by introducing a nitrogen oxide gas and ozone-containing oxygen or air into a halogenated organic solvent dissolving or suspending therein an aromatic compound, thereby subjecting the aromatic compound to nitration. By the use of a system comprising the nitrogen oxide and ozone-containing oxygen or air as the nitrating agent, the aromatic nitro compound can be produced under mild conditions without using any mineral acid. In addition, the various disadvantages due to the use of mineral acid in the conventional process can be avoided by the process of the present invention.Type: GrantFiled: March 27, 1992Date of Patent: August 17, 1993Assignee: Nippon Kayaku Kabushiki KaishaInventors: Hitomi Suzuki, Takashi Murashima, Kenkichi Tsukamoto
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Patent number: 5227538Abstract: A process is provided for the catalytic asymmetric reduction of ketones to provide alcohol reaction products which are enriched in one enantiomer. The asymmetric reduction is accomplished utilizing an achiral metal precatalyst in combination with an optically active additive.Type: GrantFiled: November 14, 1991Date of Patent: July 13, 1993Assignee: Massachusetts Institute of TechnologyInventors: Stephen L. Buchwald, Alberto Gutierrez, Robert B. Grossman
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Patent number: 5210339Abstract: An improved process for the nitration of a substituted or unsubstituted benzocyclobutene compound in a reaction mixture comprising a nitrating agent, an unhalogenated carboxylic acid anhydride, clay and a solvent to produce a corresponding nitrobenzocyclobutene compound, is that wherein:(a) the solvent has a density above that of the nitrating agent or an extractable precursor thereof;(b) the reaction mixture is heated at a temperature such that solvent is removed from the reaction mixture to a site outside the reaction mixture to extract nitrating agent or extractable precursor thereof; and(c) the thus-extracted nitrating agent or precursor thereof is fed into the reaction mixture to nitrate the benzocyclobutene compound.Type: GrantFiled: April 15, 1992Date of Patent: May 11, 1993Assignee: The Dow Chemical CompanyInventors: P. J. Thomas, R. Garth Pews
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Patent number: 5194672Abstract: A process for preparing a substituted styrene by reacting a bisarylalkyl ether in the presence of an acid catalyst is disclosed. The process is preferably used for the preparation of 4-acetoxystyrene from 4,4'-(oxydiethylidene)bisphenol diacetate and 4-methoxystyrene from 4,4'-(oxydiethylidene)bisphenol dimethyl ether. A process for preparing a bisarylalkyl ether by reacting a corresponding arylalkanol in the presence of an acid catalyst is also disclosed.Type: GrantFiled: May 14, 1991Date of Patent: March 16, 1993Assignee: Hoechst Celanese CorporationInventors: Mohammad Aslam, Brad L. Smith, George Kvakovszky
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Patent number: 5162583Abstract: Disclosed herein are the derivative of benzyl ether represented by the formula (I) ##STR1## which is useful as an intermediate compound of the derivatives of 1,5-diphenyl-1H-1,2,4- triazole-3-carboxamide represented by the formula (II), ##STR2## wherein R is a straight-chain alkyl group having 1 to 10 carbon atoms which is non-substituted or substituted with 1 to 19 fluorine atoms, a branched alkyl group having 3 to 10 carbon atoms which is non-substituted or substituted with 1 to 19 fluorine atoms, a cyclic alkyl group having 3 to 10 carbon atoms, an alkyl group having 1 to 3 carbon atoms which is substituted with an alicyclic structure having 3 to 7 carbon atoms, a phenyl group or an aralkyl group having 7 to 9 carbon atoms; X.sup.1 is a halogen or an alkyl group having 1 to 3 carbon atoms; X.sup.2 is a hydrogen, a halogen or an alkyl group having 1 to 3 carbon atoms; Y.sup.1 is a hydrogen or a fluorine; Y.sup.2 is a hydrogen or a fluorine; and Z is a nitro group or an amino group.Type: GrantFiled: September 27, 1990Date of Patent: November 10, 1992Assignee: Kureha Kagaku Kogyo Kabushiki KaishaInventors: Takafumi Shida, Hideo Arabori, Takeo Watanabe, Yoshikazu Kubota, Isao Ichinose, Yoichi Kanda, Shiro Yamazaki, Hiroyasu Shinkawa
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Patent number: 5149890Abstract: Pure or substantially enriched 2,4- and 2,6-dinitrotoluene can be isolated from a mixture containing these isomers if such a mixture is distilled under a pressure of 0.5 to 20 mbar at a temperature of 80.degree. to 200.degree. C. with exclusion of reducing conditions.Type: GrantFiled: November 1, 1991Date of Patent: September 22, 1992Assignee: Bayer AktiengesellschaftInventors: Gunther Rauchschwalbe, Heinz-Ulrich Blank, Ludwig Deibele, Kaspar Hallenberger, Gerhard Ruffert
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Patent number: 5118880Abstract: A method of preparing 2-bromo-4,6-dinitromesitylene having only small amounts of impurities, by first mixing fuming sulfuric acid with bromomesitylene, and then adding concentrated nitric acid.Type: GrantFiled: June 25, 1991Date of Patent: June 2, 1992Assignee: E. I. Du Pont de Nemours & Co.Inventors: William A. Beck, David P. Higley, John R. Tyndall
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Patent number: 5099080Abstract: Described herein is a one pot continuous improved process for preparing dinitrotoluene by reacting toluene with concentrated nitric acid.Type: GrantFiled: March 8, 1991Date of Patent: March 24, 1992Assignee: Olin CorporationInventor: Allen B. Quakenbush