Polynitrobenzenes Containing Alkoxy and Alkylenedioxy groups: Potential HEMs and Precursors of New Energetic Materials

• Autorzy: Šarlauskas J.
• Języki publikacji: EN

Abstrakty

EN

Several di-, tri- and tetranitroderivatives of alkoxy-, dialkoxy-, trialkoxy- and cyclic alkylenedioxybenzene derivatives were synthesized by nitration of starting compounds under different conditions and their properties were compared to the already known 2,4,6-trinitroanisole and TNT. Synthesized trinitro- and tetranitrocompounds of alkoxy-/alkylenedioxybenzene (especially cyclic derivatives) may serve as useful precursors for the synthesis of numerous energetic derivatives. The highest melting point (286 C) and calculated density (1.907 g/cm3) is marked for 5,6,7,8-tetranitro-2,3-dihydro-1,4-benzodioxine (TNBD). Promising properties of the latter compound allow further exploration of this material as a potential thermostable HEM.

Słowa kluczowe

EN

polynitroderivatives; HEMs; synthesis; 5,6,7,8-tetranitro-2,3-dihydro-1,4-benzodioxine (TNBD); reactions

• Czasopismo: Central European Journal of Energetic Materials
• Rocznik: 2010
• Tom: Vol. 7, nr 4
• Strony: 313--324
• Opis fizyczny: Bibliogr. 17 poz.

Twórcy

autor

Šarlauskas J.

• Institute of Biochemistry, Mokslininku 12, LT-08662, Vilnius, Lithuania,

Bibliografia

• [1] Agrawal J.P., Hodgson R., Organic Chemistry of Explosives, Wiley Interscience, N.Y. 2007, pp. 1-384.
• [2] Urbanski T., Chemistry and Technology of Explosives, Vol. 1-4, Warszawa 1964.
• [3] Orlova Ye.Yu., Chemistry and Technology of High Explosives, Khimija, Leningrad, 1973, pp. 1-686. (In Russian).
• [4] Everest D., The Power of High Explosives in Theory and Practice, Picatinny Arsenal, New Jersey (Unclassified), 2008, pp. 1-150.
• [5] Pagoria P.F., Lee G.S., Mitchell A.R., Schmidt R.D., A Review of Energetic Materials Synthesis, Thermochim. Acta, 2002, 384, 187-204.
• [6] Coburn M.D., Harris B.W., Lee K.-Y., Stinecipher M.M., Heyden H.H., Explosives Synthesis at Los Alamos, Ind. Eng. Chem. Prod. Res. Dev., 1986, 25, 68-72.
• [7] Heertjes P.M., Dahmen E.A.M.F., Wierda T. G., The Nitroderivatives of 1:2 Ethylenedioxybenzene (pyrocatecholethylene ether) Obtained by Direct Nitration, Recl. Trav. Chim. Pays-Bas, 1941, 60, 569-576.
• [8] Clarkson C.E., Holden I.G., Malkin T., The Nitration of Dimethylaniline to Tetryl, 2,4,6,N-Tetranitromethylaniline. The Course of Reaction, J. Chem. Soc., 1950, 1556-1562.
• [9] Dacons J.C., Camlet M.J., Heat Resistant Explosives. III. DATB from 1,3-dimethoxy-2,4,6-trinitrobenzene (C), Navord report 6208, (Unclassified), 1958, 1-20.
• [10] Bellamy A., Ward S.J., Golding P., A New Synthetic Route to 1,3,5-Triamino-2,4,6-Trinitrobenzene (TATB), Propellants, Explos., Pyrotech., 2002, 27(2), 49-58.
• [11] Šarlauskas J., Microwave-assisted Synthesis of Picryl-substituted Azole Derivatives, Proc. Int. Conference “Organic Chemistry”, Lithuania, Kaunas, Apr.19, 2009, pp. 12-17.
• [12] Šarlauskas J., Misevičienė L., Nivinskas H., Anusevičius Ž., Čėnas N., NemeikaitėČėnienė A., Maldutis E., Harris R.J., Scrutton N.S., Reduction of Nitroaromatic Explosives by Oxygen-insensitive NAD(P)H:nitroreductase: Implications for Their Cytotoxicity and Biodegradation, Cent. Eur. J. Energ. Mater., 2006, 3(4), 89-101.
• [13] Čėnas N., Nemeikaitė-Čėnienė A., Šarlauskas J., Anusevičius Ž., Nivinskas H., Mi-sevičienė L., Marozienė A., Mechanisms of the Mammalian Cell Cytotoxicity of Explosives, in: Ecotoxicology of Explosives, (Sunahara G.I., Lotufo G., Kuperman R.G., Hawari J., Eds.), CRC Press, Boca Raton, London, New York), ISBN 978-0-8493—2839-8, 2009, 211-226.
• [14] Nemeikaitė-Čėnienė A., Miliukienė V.; Šarlauskas J., Maldutis E., Čėnas N., Chemical Aspects of Cytotoxicity of Nitroaromatic Explosives: a Review, Chemija, 2006, 17, 34–41.
• [15] Šarlauskas J., Synthesis of Some New Heterocyclic Derivatives of Benzofuroxan, 7th Natl. Lithuanian Conference “Chemistry 2005”, Lithuania, Vilnius, Feb. 25, 2005, p. 104.
• [16] Šarlauskas J., Miliukienė V., Anusevičius Ž., Misevičienė L., Krikštopaitis K., Nemeikaitė-Čėnienė A., Vitėnienė I., Čėnas N., Redox Properties and Prooxidant Cytotoxicity of Benzofuroxans: a Comparison With Nitrobenzenes, Chemija, 2009, 20(2), 109-115.
• [17] Meyer R., Köhler J., Homburg A., Explosives, 5th ed., Wiley-VCH, 2002, pp. 1-461.