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Contribution to the Synthesis of 4,10-Dinitro-2,6,8,12-tetraoxa-4,10-diazatetracyclo[5.5.0.05,903,11]dodecane (TEX)

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Języki publikacji
EN
Abstrakty
EN
The influence of the reaction conditions on 4,10-dinitro-2,6,8,12-tetraoxa- 4,10-diazatetracyclo[5.5.0.05,903,11]dodecane (TEX) yield was studied. TEX was prepared by the reaction of 1,4-diformyl-2,3,5,6-tetrahydroxypiperazine with glyoxal in nitric acid. The influence of the acidity of reaction mixture and ratios of starting materials on the yield of TEX was examined and synthesis was optimised. The highest yield (37%) was obtained at 1,4-diformyl-2,3,5,6-tetrahydroxypiperazine/nitric acid molar ratio 67 and sulfuric acid/nitric acid molar ratio around 0.15. Starting material 1,4-diformyl-2,3,5,6-tetrahydroxypiperazine was prepared from formamide and glyoxal using triethylamine or other tertiary amines to adjust suitable basicity. The best yield (84%) of 1,4-diformyl-2,3,5,6-tetrahydroxypiperazine was reached at molar ratio triethylamine/formamide equal to 0.1.
Rocznik
Strony
189--196
Opis fizyczny
Bibliogr. 19 poz.
Twórcy
autor
autor
autor
  • University of Pardubice, Faculty of Chemical Technology, Institute of Energetic Materials, Studentská 95, CZ-532 10, Pardubice, Czech Republic, robert.matyas@upce.cz
Bibliografia
  • [1] Braithwaite P.C., Edwards W.W., Hajik R.M., Highsmith T.K., Lund G.K., Wardle R.B., TEX. A Promising New Insensitive High Explosive, 29th Int. Ann. Conf. ICT, Karlsruhe, Germany, 1998, pp. 62.61-62.67.
  • [2] Lund G.K., Highsmith T.K., Braithwaite P.C., Wardle R.B., Insensitive High Performance Explosive Compositions, WO 9418144 A1, 1994.
  • [3] Wallace I.A., Braithwaite P.C., Neidert J.B., Plastisol Explosive, US 5468313, 1995.
  • [4] Doherty R.M., Simpson R.L., A Comparative Evaluation of Several Insensitive Explosives, 28th Int. Ann. Conf. ICT, Karlsruhe, Germany, 1997, pp. 32.31-32.23.
  • [5] Marraud C., Marre S., Cansell F., Aymonier C., Desensitization of Crystals of Explosive Substances by Coating, Coated Crystals of Such Substances, and Explosives, WO 2009081048 A2, 2009.
  • [6] Doll D.W., Rasmussen N., Impact Resistat Explosive Compositions, US 2010065170 A1, 2010.
  • [7] Koch E., Weapon for Selective Causation of a Detonation or Deflagration, EP 2151422 A2, 2010.
  • [8] Ramakrishnan V.T., Vedachalam M., Boyer H., 4,10-Dinitro-2,6,8,12-tetraoxa-4,10-diazatetracyclo[5.5.0.05,903,11]dodecane, Heterocycles, 1990, 31, 179-180.
  • [9] Highsmith T.K., Edwards W.W., Wardle R.B., Synthesis of 4,10-Dinitro-2,6,8,12-tetraoxa-4,10-diazatetracyclo[5.5.0.05,9.03,11]dodecane, WO 9504062 A1, 1995.
  • [10] Mareček P., Pokorná J., Vávra P., A Study of Some Insensitive Explosives, 29th Int. Ann. Conf. ICT, Karlsruhe, 1998, pp. 52.51 - 52.55.
  • [11] Wardle R.B., Hajik R.M., Hinshaw J.C., Highsmith T.K., Large-scale Synthesis of 4,10-Dinitro-2,6,8,12- tetraoxa-4,10-diazatetracyclo-[5.5.0.05,903,11]-dodecane by Nitration of Substituted Piperazines, WO 0009509 A2, 2000.
  • [12] Jalový Z., Matyáš R., The Influence of Reaction Conditions on TEX Synthesis, 5th Seminar New Trends in Research of Energetic Materials, Pardubice, Czech Republic, 2002, pp. 92-97.
  • [13] Talwar M.B., Nair J.K., Palaiah R.S., Mukundan T., Singh H., Gejji S.P., TEX: The New Insensitive High Explosive, Defence Sci. J., 2002, 52, 157-163.
  • [14] Sanderson A.J., Hajik R.M., Highsmith T.K., Johnston H.E., Synthesis for 4,10-Dinitro-2,6,8,12-tetraoxa-4,10-diazatetracyclo-[5.5.0.05,903,11]-dodecane, US 6512113 B1, 2003.
  • [15] Vail S.L., Moran C.M., Barker R.H., The Formation of N,N’-dihydroxyethylenebisamides from Glyoxal and Selected Amides, J. Org. Chem., 1965, 30, 1195-1199.
  • [16] Currie A.C., Dinwoodie A.H., Fort G., Thompson J.M.C., Base-catalyzed Reactions of Glyoxal. I. 1,4-Diformyl- and 1,4-bis(methylsulfonyl) Derivatives of 2,3,5,6-Tetrahydroxypiperazines, J. Chem. Soc. (C), 1967, 491-496.
  • [17] Vedachalam M., Ramakrishnan V.T., Boyer J.H., Dagley I.J., Nelson K.A., Adolph H.G., Gilardi R., George C., Flippen-Anderson J.L., Facile Synthesis and Nitration of cis-syn-cis-2,6-Dioxodecahydro-1H,5H-diimidazo[4,5-b:4’,5’-e] pyrazine, J. Org. Chem., 1991, 56, 3413-3419.
  • [18] Dinwoodie A.H., Gibson J.A., Parker J.B., Base-catalysed Reactions of Glyoxal. Part II. 2,3,5,7-Tetrahydroxypiperazine-1,4-disulphonic Acid Derivates, J. Chem. Soc. (C), 1967, 496-497.
  • [19] Karaghiosoff K., Klapötke T.M., Michailovski A., Nöth H., Suter M., Holl G., 1,4-Diformyl-2,3,5,6-tetranitratopiperazine: A New Primary Explosive Based on Glyoxal, Propellants, Explos., Pyrotech., 2003, 28, 1-6.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BAT6-0014-0001
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