Methyl Bonded Directly To Benzene Ring (e.g., Nitroxylene, Etc.) Patents (Class 568/940)
  • Patent number: 8907144
    Abstract: A process for continuous adiabatic nitration of toluene to mononitrotoluene (MNT). The process yields a product quality of MNT that is comparable to that obtained by isothermal production. The process uses excess toluene, with the reaction rate being controlled to maintain a residual of 0.003-0.102 wt % nitric acid in the spent acid and an orange to red color of the spent acid. Further process conditions include re-concentrated sulfuric acid at 83 to 99 degrees C. with a concentration of sulfuric acid from 66 to 70.5 wt %. This is mixed with nitric acid to generate a mixed acid with 1.0 to 3.8 wt % nitric acid and toluene is added at a rate of 1.1 to 1.71 moles toluene/mole nitric acid. The reactants are mixed in a reactor with an overall average mixing intensity of 5.8 to 19 W/kg of contained solution.
    Type: Grant
    Filed: March 22, 2012
    Date of Patent: December 9, 2014
    Assignee: NORAM International Limited
    Inventor: Michael Gattrell
  • Publication number: 20130253233
    Abstract: A process for continuous adiabatic nitration of toluene to mononitrotoluene (MNT). The process yields a product quality of MNT that is comparable to that obtained by isothermal production. The process uses excess toluene, with the reaction rate being controlled to maintain a residual of 0.003-0.102 wt % nitric acid in the spent acid and an orange to red color of the spent acid. Further process conditions include re-concentrated sulfuric acid at 83 to 99 degrees C. with a concentration of sulfuric acid from 66 to 70.5 wt %. This is mixed with nitric acid to generate a mixed acid with 1.0 to 3.8 wt % nitric acid and toluene is added at a rate of 1.1 to 1.71 moles toluene/mole nitric acid. The reactants are mixed in a reactor with an overall average mixing intensity of 5.8 to 19 W/kg of contained solution.
    Type: Application
    Filed: March 22, 2012
    Publication date: September 26, 2013
    Applicant: NORAM International Limited
    Inventor: Michael Gattrell
  • Publication number: 20130122599
    Abstract: A mass spectrometry electron transfer dissociation reagent comprising an unsaturated compound having a Frank Condon factor between 0.1 and 1.0 and an electron affinity having a positive value between 0.1 to 150 kJ/mol.
    Type: Application
    Filed: January 31, 2011
    Publication date: May 16, 2013
    Applicant: MICROMASS UK LIMITED
    Inventors: Jeffery Mark Brown, Iain Campuzano, Darryl W. Brousmiche, Craig Dorschel, Jonathan Paul Williams, Steven Derek Pringle, Keith Richardson
  • Publication number: 20130018210
    Abstract: A method and apparatus for removing non-aromatic impurities from non-nitrated aromatic reactant in a nitration production process, in which process an aromatic reactant is nitrated (100) to produce a nitrated aromatic product using a molar excess of the aromatic reactant, and non-nitrated aromatic reactant is recovered (102) from the produced nitrated aromatic product and is recycled (104) for use in the nitration production process. A portion of the removed excess non-nitrated aromatic reactant is diverted (106) and subjected to nitration (108). The nitrated stream may be further processed by separating out the spent acids (110) and the non-aromatic impurities (116). These streams may be sent (114, 118) to a suitable location in the nitration production train.
    Type: Application
    Filed: February 17, 2011
    Publication date: January 17, 2013
    Applicant: NORAM INTERNATIONAL LIMITED
    Inventors: Alfred A. Guenkel, Sergio Berretta
  • Publication number: 20120136181
    Abstract: A method of removing alkalinity and salt from a nitroaromatic product downstream of water washing to remove mineral acids and alkaline washing to remove salts of organic acids, comprises washing the product stream with an acidic aqueous solution, prior to the step of removing excess organic reactant, by steam stripping or distillation. Acid removed from the stripper or column is recycled back for use in the acidic washing. The acidic washing is done instead of the neutral washing step of the prior art. It removes residual salt and decreases the level of entrained colloidal water in the nitroaromatic product.
    Type: Application
    Filed: August 18, 2009
    Publication date: May 31, 2012
    Applicant: NORAM INTERNATIONAL LIMITED
    Inventor: Sergio Berretia
  • Publication number: 20110237836
    Abstract: The present invention relates to a process for preparing nitrobenzene derivatives and aniline derivatives, which are of significance as intermediates for fungicidally active alkylanilides.
    Type: Application
    Filed: July 12, 2007
    Publication date: September 29, 2011
    Applicant: Bayer CropScience AG
    Inventor: Alexander Straub
  • Publication number: 20110224463
    Abstract: Modular microreactors are provided composed of microreactor parts including a plate body which has, on one plate side, a groove-shaped depression in which a reactor tube is accommodated, and the reaction tube has connection ends on the outer sides of the plate body. Also disclosed are reaction tubes for turbulent mixing, kits for producing the reactors and the use thereof for commencing chemical reactions.
    Type: Application
    Filed: November 10, 2009
    Publication date: September 15, 2011
    Inventors: Stefan Zikeli, Friedrich Ecker, Michael Longin, Klause Weidinger
  • Publication number: 20110178199
    Abstract: Disclosed herein are a reaction method and a production method of an organic compound which are capable of achieving high reaction selectivity according to the purpose and a high production rate of a target substance. The methods include at least two fluids, wherein at least one kind of the fluids is a fluid containing at least one organic compound and at least one kind of the fluids other than the above fluid is a fluid containing at least one reactant in the form of a liquid or solution, and the respective fluids join together in a thin film fluid foamed between processing surfaces arranged to be opposite to each other so as to be able to approach to and separate from each other, at least one of which rotates relative to the other, whereby an organic reaction is performed in the thin film fluid.
    Type: Application
    Filed: September 11, 2008
    Publication date: July 21, 2011
    Applicant: M. Technique Co., Ltd.
    Inventor: Masakazu Enomura
  • Patent number: 7928270
    Abstract: A process is proposed for distillatively removing dinitrotoluene from process wastewater from the preparation of dinitrotoluene by nitrating toluene with nitrating acid, which comprises basifying the process wastewater to a pH of >8.5, feeding it to a stripping column in the upper region thereof and stripping it with steam in countercurrent to obtain a vapor stream laden with dinitrotoluene and a bottom stream depleted in dinitrotoluene compared to the process wastewater used.
    Type: Grant
    Filed: March 6, 2007
    Date of Patent: April 19, 2011
    Assignee: BASF Aktiengesellschaft
    Inventors: Ulrich Penzel, Ruediger Fritz, Holger Allardt, Johannes Adam, Anne-Kathrin Merten
  • Publication number: 20100331566
    Abstract: The invention provides synthetic methods that utilize bromo or chloro substituents as blocking groups during the functionalization of aromatic rings, as well as compounds that are prepared from such methods.
    Type: Application
    Filed: June 25, 2010
    Publication date: December 30, 2010
    Inventors: Leslie S. Jimenez, Ahalya Ramanathan
  • Publication number: 20100130796
    Abstract: Improved micro machined (MEMs scale) heaters, which are particularly suitable for use in MEMs scale preconcentrators. Preferably the heater possess a trapping medium, in particular a polymer of intrinsic microporosity (PIMs). There is further provided devices comprising the preconcentrator, and methods of preparation and use. There is particular benefit directed to the use of a MEMs scale heater coated with the PIMs for use in hand-held or field portable chemical detection devices. The heater comprises a number of electrically conducting paths which have been engineered so that the electrical resistance of all the electrically conducting paths are substantially equal, to provide a more uniform heat distribution.
    Type: Application
    Filed: June 25, 2008
    Publication date: May 27, 2010
    Inventors: David J. Combes, Tomothy I. Cox, Ian C. Sage
  • Patent number: 7560462
    Abstract: Substituted urea compounds useful in the treatment of diseases and C1-3alkyleneOR3 conditions related to DNA damage or lesions in DNA replication are disclosed formula (I), wherein X1 is null, —O—, —S—, —CH2—, or —N(R1)—; X2 is —O—, . -£>. -, or —N(R1)—,—. . Y xs 0 or S; or =y represents two hydrogen atoms attached to a common carbon atom, —W is selected from the group consisting of heteroaryl, aryl, heterocycloalkyl, cycloalkyl, and C1-6alkyl substituted with a heteroaryl. or aryl group; R6 is —C?C—R7 or heteroaryl; R8, R9, and R10, independently, are selected from the group consisting of halo, optionally substituted C1-6alkyl, C2-6alkenyl, C2-6alkynyl, OCP3, CF3, NO2, CN, NC, N(R3)2, OR3, CO2R3, C(O)N (R3)2, C(O)R3, N(R1)COR3, N(R1)C(O)OR3, N(R8)C(O)OR3, N(R1)C(O)C1-3alkyleneC(O)R3, N(R1)C(O)C1 -3alkyleneC(O)OR3, N(R1)C(O)C1-3alkyleneOR3, N(R1)C(O)C1-3alkyleneNHC(O)OR3, N(R1)C(O)C1-3alkyleneSO2.
    Type: Grant
    Filed: July 1, 2005
    Date of Patent: July 14, 2009
    Assignee: ICOS Corporation
    Inventors: John Joseph Gaudino, Adam Wade Cook
  • Patent number: 6953869
    Abstract: 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: Grant
    Filed: June 28, 2004
    Date of Patent: October 11, 2005
    Assignee: Bayer MaterialScience AG
    Inventors: Jürgen Münnig, Dietmar Wastian, Wolfgang Lorenz, Berthold Keggenhoff
  • Patent number: 6936741
    Abstract: 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: Grant
    Filed: June 28, 2004
    Date of Patent: August 30, 2005
    Assignee: Bayer MaterialScience AG
    Inventors: Jürgen Münnig, Dietmar Wastian, Wolfgang Lorenz, Berthold Keggenhoff
  • Patent number: 6906231
    Abstract: 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: Grant
    Filed: October 5, 2001
    Date of Patent: June 14, 2005
    Assignee: The Queen's University of Belfast
    Inventors: Martyn John Earle, Suhas Prabhakar Katdare
  • Patent number: 6825388
    Abstract: The present invention relates to the process for vapor phase nitration of o-xylene using dilute nitric acid over H-beta zeolite. More particularly it relates to the selective formation of 4-nitro o-xylene by vapor phase nitration of 0-xylene using dilute nitric acid over commercially available H-beta catalyst. The continuous process of nitration of o-xylene comprises of a reaction carried out in a downflow reactor using o-xylene and dilute nitric acid with mole ratio of 2:1 to 1:2 and WHSV of 0.1-0.5 at 100-250° C. at atmospheric pressure.
    Type: Grant
    Filed: March 25, 2003
    Date of Patent: November 30, 2004
    Assignee: Council of Scientific and Industrial Research
    Inventors: Mohan Keraba Dongare, Pratap Tukaram Patil, Kusum Madhukar Malshe
  • Patent number: 6768032
    Abstract: 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: Grant
    Filed: April 2, 2002
    Date of Patent: July 27, 2004
    Assignee: Bayer Chemicals AG
    Inventors: Matthias Gotta, Ralf Demuth, Eberhard Zirngiebl, Hans-Martin Weber, Georg Ronge
  • Patent number: 6703532
    Abstract: 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: Grant
    Filed: December 21, 2001
    Date of Patent: March 9, 2004
    Assignee: Council of Scientific and Industrial Research
    Inventors: Boyapati Manoranjan Choudary, Mannepalli Lakshmi Kantam, Nadakuditi Sailendra Kumar, Kompella Vishweshwara Ram Prasad, Kondapuram Vijaya Raghavan
  • Patent number: 6620981
    Abstract: The present invention relates to a process for the preparation of nitrotoluenesl. More particularly, the present invention relates to a process for the preparation of nitrotoluenes with high para -selectivity from toluene using zeolite beta with different binders as a catalyst.
    Type: Grant
    Filed: March 20, 2002
    Date of Patent: September 16, 2003
    Assignee: Council of Scientific and Industrial Research
    Inventors: Boyapati Manoranjan Choudary, Mannepalli Lakshmi Kantam, Kompella Vishweshwar Ramprasad
  • Patent number: 6583327
    Abstract: 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: Grant
    Filed: October 26, 2001
    Date of Patent: June 24, 2003
    Assignee: Bayer Aktiengesellschaft
    Inventors: Ralf Demuth, Frank Döbert, Harald Petersen, Georg Ronge, Hans-Martin Weber, Thomas Würminghausen, Eberhard Zirngiebl
  • Patent number: 6515189
    Abstract: 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: Grant
    Filed: February 5, 2001
    Date of Patent: February 4, 2003
    Assignee: British Nuclear Fuels PLC
    Inventors: Paul Harston, John Burns, Colin Ramshaw
  • Patent number: 6506948
    Abstract: 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: Grant
    Filed: February 7, 2002
    Date of Patent: January 14, 2003
    Assignee: Air Products and Chemicals, Inc.
    Inventor: John Edward Sawicki
  • Publication number: 20020091290
    Abstract: 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: Application
    Filed: October 26, 2001
    Publication date: July 11, 2002
    Inventors: Ralf Demuth, Frank Dobert, Harald Petersen, Georg Ronge, Hans-Martin Weber, Thomas Wurminghausen, Eberhard Zirngiebl
  • Patent number: 6303820
    Abstract: 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: Grant
    Filed: November 6, 2000
    Date of Patent: October 16, 2001
    Assignee: Bayer Aktiengesellschaft
    Inventors: Henry Giera, Walter Lange, Michaela Meiers, Raul Pires
  • Patent number: 6291726
    Abstract: 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: Grant
    Filed: October 18, 2000
    Date of Patent: September 18, 2001
    Assignee: Inha University Foundation
    Inventors: Bon-Su Lee, Kyoo-Hyun Chung, Yoon-Sik Lee, Young-Gyu Kim
  • Patent number: 6284894
    Abstract: 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: Grant
    Filed: December 17, 1999
    Date of Patent: September 4, 2001
    Assignee: Nycomed Imaging AS
    Inventors: Fredrik Ek, Lars Goran Wistrand
  • Patent number: 6274775
    Abstract: 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: Grant
    Filed: November 6, 2000
    Date of Patent: August 14, 2001
    Assignee: Bayer Aktiengesellschaft
    Inventors: Henry Giera, Michaela Meiers, Uwe Hugger
  • Patent number: 6255542
    Abstract: A process for preparing 2-chloro-4-nitroalkylbenzenes is provided which comprises a ring chlorination of 4-nitroalkylbenzenes with elemental chlorine or chlorine-releasing compounds in liquid phase and in the presence of Friedel-Crafts catalysts and specific sulphur-containing aromatic compounds as co-catalysts.
    Type: Grant
    Filed: August 21, 2000
    Date of Patent: July 3, 2001
    Assignee: Bayer Aktiengesellschaft
    Inventors: Franz-Josef Mais, Helmut Lahr
  • Patent number: 6242657
    Abstract: 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: Grant
    Filed: April 26, 2000
    Date of Patent: June 5, 2001
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bernd-Michael König, Johannes Dühr, Hans-Joachim Raatz, Manfred Kaczorowski
  • Patent number: 5847240
    Abstract: 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: Grant
    Filed: March 24, 1997
    Date of Patent: December 8, 1998
    Assignee: Arco Chemical Technology, L.P.
    Inventors: Allen B. Quakenbush, Buford T. Pennington
  • Patent number: 5763697
    Abstract: 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: Grant
    Filed: May 16, 1996
    Date of Patent: June 9, 1998
    Assignee: Josef Meissner GmbH & Co.
    Inventors: Heinrich Hermann, Jurgen Gebauer
  • Patent number: 5728901
    Abstract: 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: Grant
    Filed: October 4, 1996
    Date of Patent: March 17, 1998
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Dorai Ramprasad, Francis Joseph Waller, Anthony Gerard Barrett, David Christopher Braddock
  • Patent number: 5648565
    Abstract: 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: Grant
    Filed: July 12, 1996
    Date of Patent: July 15, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bernd-Michael Konig, Helmut Judat, Heinz Ulrich Blank
  • Patent number: 5395995
    Abstract: 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: Grant
    Filed: May 10, 1993
    Date of Patent: March 7, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Dieter Grenner, Thomas Schieb, Gerhard Wiechers
  • Patent number: 5315043
    Abstract: 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: Grant
    Filed: February 5, 1992
    Date of Patent: May 24, 1994
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Richard E. Fernandez, Mark H. Krackov
  • Patent number: 5247124
    Abstract: 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: Grant
    Filed: August 25, 1992
    Date of Patent: September 21, 1993
    Assignee: Hoechst Celanese Corporation
    Inventors: Mohammad Aslam, Brad L. Smith, George Kvakovszky
  • Patent number: 5245092
    Abstract: 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: Grant
    Filed: September 14, 1992
    Date of Patent: September 14, 1993
    Assignee: Olin Corporation
    Inventor: Allen B. Quakenbush
  • Patent number: 5237077
    Abstract: 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: Grant
    Filed: March 27, 1992
    Date of Patent: August 17, 1993
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Hitomi Suzuki, Takashi Murashima, Kenkichi Tsukamoto
  • Patent number: 5210339
    Abstract: 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: Grant
    Filed: April 15, 1992
    Date of Patent: May 11, 1993
    Assignee: The Dow Chemical Company
    Inventors: P. J. Thomas, R. Garth Pews
  • Patent number: 5194672
    Abstract: 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: Grant
    Filed: May 14, 1991
    Date of Patent: March 16, 1993
    Assignee: Hoechst Celanese Corporation
    Inventors: Mohammad Aslam, Brad L. Smith, George Kvakovszky
  • Patent number: 5162583
    Abstract: 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: Grant
    Filed: September 27, 1990
    Date of Patent: November 10, 1992
    Assignee: Kureha Kagaku Kogyo Kabushiki Kaisha
    Inventors: Takafumi Shida, Hideo Arabori, Takeo Watanabe, Yoshikazu Kubota, Isao Ichinose, Yoichi Kanda, Shiro Yamazaki, Hiroyasu Shinkawa
  • Patent number: 5149890
    Abstract: 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: Grant
    Filed: November 1, 1991
    Date of Patent: September 22, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gunther Rauchschwalbe, Heinz-Ulrich Blank, Ludwig Deibele, Kaspar Hallenberger, Gerhard Ruffert
  • Patent number: 5118880
    Abstract: 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: Grant
    Filed: June 25, 1991
    Date of Patent: June 2, 1992
    Assignee: E. I. Du Pont de Nemours & Co.
    Inventors: William A. Beck, David P. Higley, John R. Tyndall
  • Patent number: 5099078
    Abstract: Described herein is a one pot continuous process for preparing dinitrotoluene by reacting toluene with concentrated nitric acid.
    Type: Grant
    Filed: December 21, 1990
    Date of Patent: March 24, 1992
    Assignee: Olin Corporation
    Inventor: Allen B. Quakenbush
  • Patent number: 5099079
    Abstract: Described herein is a process for separating an acid impurity from a solution containing acid and a nitro substituted aromatic compound by contacting the solution with at least one molten nitrate salt.
    Type: Grant
    Filed: July 26, 1990
    Date of Patent: March 24, 1992
    Assignee: Olin Corporation
    Inventor: Allen B. Quakenbush
  • Patent number: 5099080
    Abstract: Described herein is a one pot continuous improved process for preparing dinitrotoluene by reacting toluene with concentrated nitric acid.
    Type: Grant
    Filed: March 8, 1991
    Date of Patent: March 24, 1992
    Assignee: Olin Corporation
    Inventor: Allen B. Quakenbush
  • Patent number: 5095157
    Abstract: In the preparation of 2-chloro-4-nitro-alkylbenzene by reaction of 4-nitro-alkylbenzene with elemental chlorine or chlorine-releasing compounds in the presence of a Friedel-Crafts catalyst in the liquid phase, particularly high selectivities in respect of the target compounds chlorinated exclusively in the 2-position are achieved if a dibenzo-condensed sulphur heterocycle of the formula ##STR1## having the meanings given in the description for R.sup.1 to R.sup.8, X and n, is used as co-catalyst.
    Type: Grant
    Filed: May 2, 1990
    Date of Patent: March 10, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Franz-Josef Mais, Helmut Fiege
  • Patent number: 5057632
    Abstract: Described herein is a continuous process for preparing dinitrotoluene by reacting toluene with dilute nitric acid to produce mononitrotoluene, then reacting the mononitrotoluene with concentrated nitric acid to produce dinitrotoluene.
    Type: Grant
    Filed: October 22, 1990
    Date of Patent: October 15, 1991
    Assignee: Olin Corporation
    Inventors: Peter C. Imm, Allan B. Quakenbush
  • Patent number: 5030776
    Abstract: Nitrobenzenes are prepared by nitrating benzenes in vapor phase using nitric acid as a nitrating agent and under continuous or intermittent feeding of sulfuric acid as a catalyst in the presence of a catalyst comprising sulfuric acid supported on a carrier or in the presence of only a carrier. This process can provide very high and prolonged nitration activity.
    Type: Grant
    Filed: June 6, 1990
    Date of Patent: July 9, 1991
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Hiroshi Sato, Koichi Nagai, Hiroshi Yoshioka, Yoshihiko Nagaoka
  • Patent number: 5012019
    Abstract: The present invention relates to a process for purifying an aromatic nitration product mixture comprising a nitrated aromatic compound, water, and nitric or sulfuric acid which comprises without regard to sequence: (a) removing at least a portion of said water from said product mixture by contacting and reacting said water in said mixture with magnesium nitrate trihydrate to form magnesium nitrate pentahydrate or magnesium nitrate hexahydrate and removing said magnesium nitrate pentahydrate or magnesium nitrate hexahydrate from said nitrated aromatic compound in said product mixture, and (b) removing at least a portion of said acid from said product mixture by contacting and reacting said acid with an ionic or non-ionic absorbent to form a reacted absorbent and removing said reacted absorbent from said nitrated aromatic compound in said product mixture.
    Type: Grant
    Filed: January 26, 1990
    Date of Patent: April 30, 1991
    Assignee: Olin Corporation
    Inventors: Robert W. Mason, Peter C. Imm, Paul J. Craney, Thomas W. Offill, Robert T. Brooker