Polynitro Patents (Class 568/932)
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Patent number: 11460776Abstract: A method of making a semiconductor device is provided. The method includes forming a photoresist material over a substrate, the photoresist material having a polymer that includes a backbone having a segment and a linking group, the segment including a carbon chain and an ultraviolet (UV) curable group, the UV curable group coupled to the carbon chain and to the linking group; performing a first exposure process that breaks the backbone of the polymer via decoupling the linking group from the connected UV curable group of each segment; performing a second exposure process to form a patterned photoresist layer; and developing the patterned photoresist layer.Type: GrantFiled: November 1, 2019Date of Patent: October 4, 2022Assignee: TAIWAN SEMICONDUCTOR MANUFACTURING COMPANY, LTD.Inventors: An-Ren Zi, Ching-Yu Chang
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Patent number: 10466593Abstract: A method of making a semiconductor device is provided. The method includes forming a photoresist material over a substrate, the photoresist material having a polymer that includes a backbone having a segment and a linking group, the segment including a carbon chain and an ultraviolet (UV) curable group, the UV curable group coupled to the carbon chain and to the linking group; performing a first exposure process that breaks the backbone of the polymer via decoupling the linking group from the connected UV curable group of each segment; performing a second exposure process to form a patterned photoresist layer; and developing the patterned photoresist layer.Type: GrantFiled: July 29, 2015Date of Patent: November 5, 2019Assignee: TAIWAN SEMICONDUCTOR MANUFACTURING COMPANY, LTD.Inventors: An-Ren Zi, Ching-Yu Chang
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Patent number: 8445734Abstract: The present invention discloses novel and improved nucleosidic and nucleotidic compounds that are useful in the light-directed synthesis of oligonucleotides, as well as, methods and reagents for their preparation. These compounds are characterized by novel photolabile protective groups that are attached to either the 5?- or the 3?-hydroxyl group of a nucleoside moiety. The photolabile protective group is comprised of a 2-(2-nitrophenyl)-ethyoxycarbonyl skeleton with at least one substituent on the aromatic ring that is either an aryl, an aroyl, a heteroaryl or an alkoxycarbonyl group. The present invention includes the use of the aforementioned compounds in light-directed oligonucleotide synthesis, the respective assembly of nucleic acid microarrays and their application.Type: GrantFiled: June 2, 2010Date of Patent: May 21, 2013Assignee: NIGU Chemie GmbHInventors: Sigrid Buehler, Markus Ott, Wolfgang Pfleiderer
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Patent number: 7767868Abstract: A process for preparing trinitrotoluene (TNT) in which toluene is treated with nitric acid having a concentration of about 90% to about 99%, and preferably about 98% to about 99%, by weight at a temperature of less than about 60° C., and preferably less than 30° C., to produce high purity dinitrotoluene. The resulting dinitrotoluene is then treated with nitric acid having a concentration of about 98% to about 99% by weight and trifluoromethane sulfuric acid to produce high purity TNT.Type: GrantFiled: April 21, 2004Date of Patent: August 3, 2010Assignee: BAE Ordnance Systems, Inc.Inventors: Keith S. Kyler, Andrew R. Wilson, Curtis Teague
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Patent number: 7449610Abstract: The invention provides a process for removing nitrocresols from wastewater of mononitrotoluene preparation, which comprises acidifying the alkaline wastewater of mononitrotoluene preparation with acids to a pH of at most 3 and treating the nitrocresols with an extractant. The invention further provides the preparation of dinitrotoluene by use of the nitrocresol-containing extracts as a feedstock.Type: GrantFiled: September 18, 2004Date of Patent: November 11, 2008Assignee: BASF SEInventors: Johannes Buettner, Holger Allardt, Reinhard Tonder, Reiner Reetz, Michael Reichelt
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Publication number: 20080268462Abstract: A method for performing a multiplexed diagnostic assay, such as for two or more different targets in a sample, is described. One embodiment comprised contacting the sample with two or more specific binding moieties that bind specifically to two or more different targets. The two or more specific binding moieties are conjugated to different haptens, and at least one of the haptens is an oxazole, a pyrazole, a thiazole, a nitroaryl compound other than dinitrophenyl, a benzofurazan, a triterpene, a urea, a thiourea, a rotenoid, a coumarin, a cyclolignan, a heterobiaryl, an azo aryl, or a benzodiazepine. The sample is contacted with two or more different anti-hapten antibodies that can be detected separately. The two or more different anti-hapten antibodies may be conjugated to different detectable labels.Type: ApplicationFiled: November 1, 2007Publication date: October 30, 2008Inventors: Jerome W. Kosmeder, Mark Lefever, Donald Johnson, Michael Farrell, Zhanna Zhilina, Christopher Bieniarz
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Patent number: 6984762Abstract: The invention relates to a process for the production of dinitrotoluene by the two-stage nitration of toluene. In the first stage of this process, toluene was reacted adiabatically with nitrating acid so that at least 90% of the toluene was reacted off and no more than 70% of the toluene formed dinitrotoluene. The resulting organic phase containing mononitrotoluene and the aqueous acid phase containing sulfuric acid were separated, and the aqueous acid phase containing sulfuric acid was concentrated by flash evaporation. The resulting concentrated sulfuric acid was recycled into the reaction in the first stage, and/or into the reaction in the second stage, and/or into the concentration in the second stage. In the second stage, the organic phase containing mononitrotoluene from the first stage was completely reacted isothermally with nitrating acid.Type: GrantFiled: February 17, 2004Date of Patent: January 10, 2006Assignee: Bayer AktiengesellschaftInventors: Erwin Dieterich, Anke Hielscher, Berthold Keggenhoff, Manfred Keller-Killewald, Jürgen Münnig, Dietmar Wastian
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Patent number: 6815567Abstract: The present invention is directed to a novel 4-sulfanylalkyl-3,5-dinitro benzyl alcohol compound and its preparation method, more specifically, derivatives of 4-sulfanylalkyl-3,5-dinitro benzyl alcohol compound having the following formula 1 and its preparation method: wherein, R is hydrogen, alkyl group, or acetyl group, and n is an integer of 1 to 25. The organic compound of the present invention can be used as a material for molecular electronic device.Type: GrantFiled: December 5, 2003Date of Patent: November 9, 2004Assignee: Electronics and Telecommunications Research InstituteInventors: Hyoyoung Lee, Mun Seok Jeong, Sung Yool Choi, Tae Hyoung Zyung
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Patent number: 6696613Abstract: A process for preparing compounds of the formula: wherein R2 is lower alkyl; or phenyl optionally substituted by from one to five groups, the same or different, which are lower alkyl, lower haloalkyl, halogen or —SR4; R3 is halogen, lower alkyl, lower haloalkyl, lower alkoxy, lower haloalkoxy, —S-alkyl, cycloalkyl having from 3 to 7 carbon atoms in the ring, alkenyl or alkynyl having from 3 to 7 carbon atoms, or —(CR5R6)—SR2 wherein q is one or two; R4 is lower alkyl; R5 and R6 independently represent hydrogen, lower alkyl or lower haloalkyl; and n is zero or an integer from one to three; intermediate compounds of the formula: and processes for preparing them.Type: GrantFiled: December 31, 2002Date of Patent: February 24, 2004Assignee: Rhone Poulenc AgrochimieInventors: Virginie Pevere, Alain Gadras, Susan Mary Cramp, Charles Walter Ellwood
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Publication number: 20030097022Abstract: A process for preparing compounds of the formula: 1Type: ApplicationFiled: December 31, 2002Publication date: May 22, 2003Inventors: Virginie Pevere, Alain Gadras, Susan Mary Cramp, Charles Walter Ellwood
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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: 6486346Abstract: Durene diisocyanate is prepared by reacting durene with nitric acid in sulfuric acid, catalytic hydrogenation of the dinitrodurene that is formed, and phosgenation of the resultant durene diamine in a conventional manner. The intermediate products dinitrodurene and durene diamine do not have to be worked up in a complicated manner as solid products, but can be worked up in dissolved form. The intermediate products dinitrodurene and durene diamine do not have to be isolated and purified in a complicated manner. but can be processed directly after preparation. Another advantage of this process is that only a single organic solvent need be used for the overall preparation process. Separation and re-use of spent acid in the conversion of durene with nitric acid also renders the process of the present invention significantly less environmentally harmful than the known processes of the prior art.Type: GrantFiled: December 14, 1999Date of Patent: November 26, 2002Assignee: Bayer AktiengesellschaftInventors: Peter Heitkämper, Klaus Jost, Stefan Penninger
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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: 6288289Abstract: An integrated process for treating alkaline wash water effluent from nitroaromatic manufacture, principally containing nitro-hydroxy-aromatic compounds is described. The integrated process concentrates the alkaline wash water to recover chemicals and water prior to treating the concentrate through supercritical water oxidation. The supercritical water oxidation step consists of treating the concentrate in the presence of an oxygen source at conditions, which are supercritical for water to cause a substantial portion of the organic component of the concentrate to oxidize. The product effluent includes a gaseous component and a clean water component, and in the event that insoluble ash is formed, an ash component. The new integrated process results in reduced chemical and water consumption compared to existing processes. In addition, the treated wash water effluent can be recycled to process or directly discharged.Type: GrantFiled: January 27, 2000Date of Patent: September 11, 2001Assignee: Noram Engineering and Constructors Ltd.Inventors: David Anthony Boyd, Stuart Alan Gairns, Alfred Alexander Guenkel
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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: 6258986Abstract: Dinitrotoluene is produced by nitrating toluene with nitrating acid under adiabatic conditions in a manner such that some mononitrotoluene is present in reaction mixture. The nitration reaction mixture is then treated to remove at least 5% by weight of water before the reaction mixture is separated into an acid phase and an organic phase. The product dinitrotoluene is recovered from the organic phase. The acid phase may be recycled after nitric acid has been added to replace that which was used in the nitration reaction.Type: GrantFiled: August 3, 1995Date of Patent: July 10, 2001Assignee: Bayer AktiengesellschaftInventors: Uwe Klingler, Thomas Schieb, Dietmar Wastian, Gerhard Wiechers, Jürgen Zimmerman
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Patent number: 6191325Abstract: Dinitro aromatic compounds are improvedly prepared by reacting an aromatic compound with a nitric acid nitrating agent and thence separating the nitrating acid from the process stream thus formed, the process stream containing said at least one dinitro aromatic compound and also having a fraction of the nitrating acid dissolved therein, the subject process also comprising (a) distilling/stripping nitric acid from said process stream, (b) recovering nitric acid from the top of the distillation/stripping vessel and recycling same to the nitration reaction and (c) washing the process stream which contains the at least one dinitro aromatic compound, but having the nitric acid removed therefrom.Type: GrantFiled: August 13, 1998Date of Patent: February 20, 2001Assignee: Rhodia ChimieInventors: Philippe Marion, Pascal Metivier
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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: 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: 5948944Abstract: A multi-step process for producing DNT employing a mononitration step in a single liquid phase at an elevated temperature using a carefully controlled amount of water, followed by a phase separation step prior to dinitration of the MNT present in the resulting organic phase. This process results in a DNT product with a desired isomer ratio of 2,4-DNT to 2,6-DNT and provide relatively fast nitration rates with less by-products.Type: GrantFiled: November 18, 1998Date of Patent: September 7, 1999Assignee: Arco Chemical Technology, L.P.Inventors: Chunjie Zhang, Buford T. Pennington, Jeffrey W. Baird, Allen B. Quakenbush, Stephen L. Goldstein, Donald L. Lickei, Peter J. Whitman
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Patent number: 5902910Abstract: This invention relates to an improved process for the production of dinitrotoluene wherein one is able to effectively employ a feed sulfuric acid, which is referred to as "weak acid" as the feed sulfuric acid for the nitration facility. The weak acid concentration, as feed, ranges from 86-91%, preferably 87-89% sulfuric acid by weight, to meet the total sulfuric acid requirements for the facility. This is accomplished by utilizing cocurrent processing in a mononitration zone and countercurrent nitration with respect to sulfuric acid in the dinitration zone.Type: GrantFiled: September 19, 1997Date of Patent: May 11, 1999Assignee: Air Products and Chemicals, Inc.Inventors: William Joseph Mazzafro, Stephen Ian Clarke, Mark Shedric Simpson, Richard Van Court Carr
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Patent number: 5874654Abstract: Environmentally-polluting nitrocresol values are removed from admixtures of nitroaromatic compounds comprised thereof, notably the media of nitration of aromatic compounds by reacting same with aqueous HNO.sub.3 /H.sub.2 SO.sub.4, by first intimately contacting such nitroaromatic compound admixtures with an oxidizing agent comprising hydrogen peroxide, javelle water, or mixture thereof, and thereafter with a neutralizing agent; the nitroaromatic aromatic compounds thus purified are conveniently catalytically hydrogenated into aromatic amines.Type: GrantFiled: September 19, 1997Date of Patent: February 23, 1999Assignee: Rhone Poulenc ChimieInventors: Antoinette Gacon-Camoz, Pascal Metivier
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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: 5820764Abstract: Objectionable byproduct aqueous effluents containing contaminating amounts of hydroxynitroaromatic compounds, in particular those aqueous effluents produced during the synthesis of nitroaromatic compounds, e.g., dinitrotoluenes, via reaction of an aromatic compound with nitric acid in the presence of sulfuric acid, are efficiently, facilely and economically treated/removed by (a) intimately contacting a mixture of at least one nitroaromatic compound and at least one hydroxynitroaromatic compound with an aqueous wash medium containing a neutralizing agent, (b) separating the resulting admixture into an organic phase and an aqueous phase, (c) recycling a fraction of the separated aqueous phase to the aqueous wash medium to thus constitute a portion thereof, and (d) periodically draining a fraction of the wash medium, whether to destruction thereof or to waste.Type: GrantFiled: October 28, 1997Date of Patent: October 13, 1998Assignee: Rhone-Poulenc ChimieInventors: Faouzi Joulak, Louis Le Bris, Philippe Marion
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Patent number: 5756867Abstract: A process for the removal and recovery of nitric acid, sulphuric acid and nitrous oxide (NO.sub.x) from crude dinitrotoluene (DNT) obtained by nitrating with a nitrating acid, a benzene derivative selected from the group consisting of tolulene or mononitrotoluene (after separation from the dinitrotoluene from the nitrating acid, wherein the crude dinitrotoluene is extracted in a plurality of steps whereby a dilute aqueous solution of nitric, sulfuric and nitrous acids countercurrently contacts the crude dinitrotoluene, the volume ratio of the dinitrotoluene to the aqueous solution being between 1:3 and 10:1, the extraction steps resulting in the formation of an aqueous extract which is blended directly into the nitrating acid for re-use in the acid nitration of the benzene derivative.Type: GrantFiled: September 15, 1995Date of Patent: May 26, 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: 5696305Abstract: Nitroaromatic compounds are produced by continuously reacting an aromatic compound with nitrating acid. The reaction mixture is separated into an organic phase from which the desired nitroaromatic compound is recovered and an acid phase. The acid phase is subjected to flash evaporation to remove at least 5% by weight of the water present therein. The vapors generated during the flash evaporation are introduced into a jet spray of coolant to produce a condensate made up coolant, condensed vapors and suspended organic compounds. A portion of the condensate is subjected to phase separation to remove water and organic compounds present therein. The water and organic compounds may be reused. The process of the present invention is particularly advantageous in that deposits which block pipelines and interfere with heat transfer are not generated.Type: GrantFiled: August 3, 1995Date of Patent: December 9, 1997Assignee: Bayer AktiengesellschaftInventors: Uwe Klingler, Thomas Schieb, Gerhard Wiechers, Jurgen Zimmermann
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Patent number: 5689018Abstract: Dinitrotoluene is produced from toluene and nitric acid in the presence of sulfuric acid in a two stage process in the first stage, toluene and nitric acid are reacted under isothermal conditions in amounts such that mononitrotoluene is produced. The reaction mixture is then separated into an organic phase and an acid phase. The organic phase is then further reacted with nitric acid under adiabatic conditions to produce dinitrotoluene. The reaction mixture is then separated into an organic phase and an acid phase. Dinitrotoluene is recovered from the organic phase. After at least 5% by weight water is removed from the acid phase and sufficient nitric acid to replace that consumed during the nitration reaction has been added, the acid phase may be recycled.Type: GrantFiled: August 3, 1995Date of Patent: November 18, 1997Assignee: Bayer AktiengesellschaftInventors: Uwe Klingler, Thomas Schieb, Gerhard Wiechers, Jurgen Zimmermann
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Patent number: 5679873Abstract: Dinitrotoluene is produced in a two-stage process from toluene and nitric acid in the presence of sulfuric acid under adiabatic conditions in the presence of nitrating acids made up of specified components. The reaction product of the first phase is separated into an acid phase and an organic phase containing the mononitrotoluene. Some water is removed from the acid phase, nitric acid is added and the resultant mixture is recycled. The organic phase containing mononitrotoluene is further nitrated to produce the dinitrotoluene. This nitration mixture is also separated into an acid phase and an organic phase. The acid phase is treated to remove some water, nitric acid is added and the resultant acid mixture is recycled. Dinitrotoluene is recovered from the organic phase. This process is advantageous in that dilute nitric acid may be used and the heat of the nitration reaction is utilized.Type: GrantFiled: August 3, 1995Date of Patent: October 21, 1997Assignee: Bayer AktiengesellschaftInventors: Uwe Klingler, Thomas Schieb, Gerhard Wiechers, Jurgen Zimmermann
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Patent number: 5663462Abstract: Dinitrotoluene and isomer mixtures of dinitrotoluene are produced in a single stage, continuous process by nitrating mononitrotoluene or an isomer mixture of mononitrotoluene in which the ortho-mononitrotoluene content is low with a nitrating acid made up of (1) from about 80 to about 100 wt. % inorganic constituents and (2) up to 20 wt. % organic constituents. The inorganic constituents of the nitrating acid include: (a) from about 60 to about 90 wt. % sulfuric acid, (b) from about 1 to about 20 wt. % nitric acid, and (c) at least 5 wt. % water. The organic constituents of the nitrating acid include: from about 70 to about 100% by weight nitrotoluene isomers and up to about 30% by weight nitration by-products. The nitration reaction is carrier out under adiabatic conditions. The molar ratio of nitric acid to mononitrotoluene during the nitration reaction is generally from about 0.7:1 to about 1.4:1.Type: GrantFiled: June 4, 1996Date of Patent: September 2, 1997Assignee: Bayer AktiengesellschaftInventors: Uwe Klingler, Thomas Schieb, Gerhard Wiechers
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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: 5616818Abstract: An aromatic compound is polynitrated in a continuous process in a single apparatus under adiabatic conditions in an emulsion as the reaction medium. From 1.3 to 3.5 mol of HNO.sub.3 per mol of aromatic compound are introduced in the form of a nitronium ion solution into the reactor with the aromatic compound under conditions such that an emulsion forms. The emulsion, which has a tendency to coalesce, is maintained by repeated dispersion. The first dispersion of the liquid streams to produce the emulsion takes place in less than one second. At least 20% of the total amount of HNO.sub.3 to be used should generally be present during this first dispersion. It is preferred, however, that the total amount of nitronium ion solution to be used be present at the time the aromatic compound and nitronium ion solution are first dispersed.Type: GrantFiled: October 13, 1995Date of Patent: April 1, 1997Assignee: Bayer AktiengesellschaftInventors: Hans-Georg Pirkl, Reinhard Schom acker, Uwe Klingler, Thomas Schieb, Gerhard Wiechers, J urgen Zimmermann
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Patent number: 5600035Abstract: Photoreactive compounds are synthesized from 2,5- or 2,6-dintrobenzyl groups. Also disclosed are methods of synthesizing reactive monomers containing 2,5- or 2,6-dintrobenzyl groups.Type: GrantFiled: July 13, 1994Date of Patent: February 4, 1997Assignee: PPG Industries, Inc.Inventors: Charles F. Kahle, II, Neil D. McMurdie, Raphael O. Kollah, Daniel E. Rardon, Gregory J. McCollum
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Patent number: 5554299Abstract: Objectionable byproduct aqueous effluents containing contaminating amounts of hydroxynitroaromatic compounds, in particular those aqueous effluents produced during the synthesis of nitroaromatic compounds, e.g., dinitrotoluenes, via reaction of an aromatic compound with nitric acid in the presence of sulfuric acid, are efficiently, facilely and economically treated/removed by (a) intimately contacting a mixture of at least one nitroaromatic compound and at least one hydroxynitroaromatic compound with an aqueous wash medium containing a neutralizing agent, (b) separating the resulting admixture into an organic phase and an aqueous phase, (c) recycling a fraction of the separated aqueous phase to the aqueous wash medium to thus constitute a portion thereof, and (d) periodically draining a fraction of the wash medium, whether to destruction thereof or to waste.Type: GrantFiled: January 3, 1995Date of Patent: September 10, 1996Assignee: Rhone-Poulenc ChimieInventors: Faouzi Joulak, Louis Le Bris, Philippe Marion
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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: 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: 5367108Abstract: Dinitro-polyalkylbenzenes can be prepared by nitration of polyalkylbenzenes using HNO.sub.3 in the presence of H.sub.2 SO.sub.4 in such a manner that at least 50% of the H.sub.2 SO.sub.4 is present as reaction medium and HNO.sub.3 and the polyalkylbenzene and any remaining H.sub.2 SO.sub.4 are added simultaneously in such a manner that the added substances polyalkylbenzene and HNO.sub.3 are in the molar ratio of 1:2-10. H.sub.2 SO.sub.4 is used at a concentration from 81 to 96% by weight and HNO.sub.3 at a concentration from 95 to 100% by weight. For the work-up, the dinitro-polyalkylbenzenes are first freed from the majority of the acids and then treated with a highly dilute aqueous solution of a dispersant for separating off residual acid.Type: GrantFiled: June 18, 1993Date of Patent: November 22, 1994Assignee: Bayer AktiengesellschaftInventors: Heinz-Ulrich Blank, Bernd-Michael Konig
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Patent number: 5334781Abstract: The invention concerns a process for the preparation of nitrobenzene from benzene and nitric acid, wherein catalysts are applied based on the zeolite clinoptilolite.Type: GrantFiled: January 15, 1993Date of Patent: August 2, 1994Assignee: CU Chemie Uetikon AGInventors: Herman W. Kouwenhoven, Leopoldo Bertea, Roel Prins
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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: 5324872Abstract: The invention concerns a gasphase process for the preparation of nitrobenzene from benzene and nitric acid, wherein catalysts are applied based on the zeolite mordenite.Type: GrantFiled: December 4, 1992Date of Patent: June 28, 1994Assignee: CU Chemie Uetikon AGInventors: Herman W. Kouwenhoven, Leopoldo Bertea, Roel Prins
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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: 5221440Abstract: A process for removing organic compounds, including nitro-hydroxy-aromatic compounds and amines, from alkaline wastewater, and in particular from wastewater generated in the production of nitrobenzene, dinitrobenzene, nitrotoluene and dinitrotoluene. The process involves distilling the alkaline wastewater steam at or near atmospheric pressure until it is concentrated five to twenty-five fold. The distillate includes water, which may be discharged to the environment, subjected to biological treatment, or recycled for use in the production process; and volatile organics, which are phase separated from the aqueous portion of the distillate and which may be recycled to the crude product stream. The concentrated residue from the distillation may be incinerated or subjected to biological treatment.Type: GrantFiled: April 20, 1992Date of Patent: June 22, 1993Assignee: Rubicon Inc.Inventors: Aki Miyagi, Walter Kraushaar, John B. Wilcoxon, Toby Gerhold
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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: 5194659Abstract: A nitrate ester which is 1,3-diamino-5-(hydroxyethylaminonitrate)-2,4,6-titrobenzene or 3-amino-3'-(hydroxyethylaminonitrate)-2,2',4,4',6,6'-hexanitrobiphenyl.Type: GrantFiled: June 15, 1992Date of Patent: March 16, 1993Assignee: The United States of America as represented by the Secretary of the NavyInventor: Michael E. Sitzmann
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Patent number: 5185454Abstract: Symmetrical diaryl-acetylenes can be prepared by reacting an aryl halide with acetylene in the presence of a palladium catalyst and a base. If the acetylene is introduced into the liquid reaction mixture using a high intensity gas dispersion means, the aryl halide used can be an aryl bromide.Type: GrantFiled: October 2, 1990Date of Patent: February 9, 1993Assignee: Bayer AktiengesellschaftInventors: Axel Bader, Dieter Arlt
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Patent number: 5099079Abstract: 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: GrantFiled: July 26, 1990Date of Patent: March 24, 1992Assignee: Olin CorporationInventor: Allen B. Quakenbush
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Patent number: 5072053Abstract: The new 1,3-di-arylmethoxy-4,6-dinitrobenzenes of the formula ##STR1## in which R.sup.1 and R.sup.2 independently of one another denote hydrogen or C.sub.1 -C.sub.4 -alkyl andAr represents C.sub.6 -C.sub.12 -aryl,can be prepared by reaction of 1,3-dihalogeno-4,6-dinitro-benzenes of the formula ##STR2## in which Hal represents chlorine or bromine, with an arylmethanol of the formulaAr--C(R.sup.1, R.sup.2)OH (IV),in which R.sup.1, R.sup.2 and Ar have the said meaning, and a strong base in the temperature range from 0.degree. to 100.degree. C.These di-arylmethoxy-dinitro-benzenes can be converted into 4,6-diaminoresorcinol by catalytic reduction with hydrogen.Type: GrantFiled: May 21, 1990Date of Patent: December 10, 1991Assignee: Bayer AktiengesellschaftInventors: Heinz U. Blank, Uwe Heinz
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Patent number: 5072061Abstract: 1,14-bis(4-nitrophenyl)-1,3,5,7,9,11,13-tetradecaheptaene having the following formula (I): ##STR1## and a method of preparing the above-mentioned 1,14-bis(4-nitrophenyl)-1,3,5,7,9,11,13-tetradecaheptaene having formula (I) by allowing a phosphonium salt having formula (II) to react with 5-(4-nitrophenyl)-2,4-pentadiene-1-al having formula (III) in the presence of a basic catalyst:R.sub.3 P.sup..sym. H.sub.2 C--CH.dbd.CH--CH.sub.2 P.sup..sym. R.sub.3.2X.sup..crclbar.Type: GrantFiled: June 4, 1990Date of Patent: December 10, 1991Assignee: Ricoh Company, Ltd.Inventors: Masaomi Sasaki, Tomoyuki Shimada, Mitsuru Hashimoto
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Patent number: 5012019Abstract: 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: GrantFiled: January 26, 1990Date of Patent: April 30, 1991Assignee: Olin CorporationInventors: Robert W. Mason, Peter C. Imm, Paul J. Craney, Thomas W. Offill, Robert T. Brooker