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Silica Sulfuric Acid/HNO3 as a Novel Heterogeneous System for the Nitrolysis of DADN to HMX under Mild Conditions

  • 투고 : 2012.07.12
  • 심사 : 2012.07.31
  • 발행 : 2012.11.20

초록

1,5-Diacetyl-3,7-dinitro-l,3,5,7-tetraazacyclooctane (DADN) is a key intermediate in the preparation of octahydro-1,3,5,7-tetranitro-1,3,5,7-tetrazocine (HMX), one of the most powerful high-melting explosives. The present investigation focuses on nitrolysis of DADN to HMX by developing a new nitrolysis process involving the use of nitric acid catalyzed by Silica Sulfuric Acid (SSA). In order to optimize the process parameters for synthesis of HMX to obtain higher yield and purity, a study was carried out with variation of some parametric conditions like time, mole ratio of SSA and nitric. This method gave us green and mild conditions for nitration reaction.

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참고문헌

  1. Siele, V. I.; Gilbert, E. E. US Patent 3939148, 1976.
  2. Silberman, L.; Adelman, S. M. Symposium Processing Propellants, Explosives and Ingredients, Section II; 1979.
  3. Greenfield, M.; Guo, Y. Q.; Bernstein, E. R. Chem. Phys. Lett. 2006, 430, 277. https://doi.org/10.1016/j.cplett.2006.09.025
  4. Bachmann, W. E.; Horton, W. J.; Jenner, E. L.; MacNaughton, N. W.; Scott, L. B. J. Am. Chem. Soc. 1951, 6, 2769.
  5. Bachmann, W. E.; Jenner, E. L. J. Am. Chem. Soc. 1951, 73, 2773. https://doi.org/10.1021/ja01150a100
  6. Das, S.; Raut, V. D.; Gawande, N. M.; Khopade, R. S.; Narasimhan, V. L. Indian. J. Chem. Technol. 2006, 13, 404.
  7. Radhakrishnan, S.; Talawar, M. B.; Venugopalan, S. J. Hazard. Mater. 2008, 152, 1317. https://doi.org/10.1016/j.jhazmat.2007.08.006
  8. Zhiyong, He.; Luo, J.; Lu, C. Cent. Eur. J. Energ. Mat. 2011, 8, 83.
  9. Chen, L.; Chen, Z. M.; Chen, X. H. Chin. J. Exp. Prop. 1986, 3, 1.
  10. Zhi, H. Z.; Luo, J.; Feng, G. A.; Lv, C. X. Chin Chem. Lett. 2009, 20, 379. https://doi.org/10.1016/j.cclet.2008.12.040
  11. Chen, J.; Wang, S. F. Prop. Exp. Pyro. 1984, 9, 58. https://doi.org/10.1002/prep.19840090206
  12. Ampleman, G.; Marois, A.; Thiboutot, S.; Hawari, J.; Greer, C. W.; Godbout, J.; Sunahara, G. I.; Shen, C. F.; Guiot, S. R. J. Labelled Compd. Radiopharm. 1999, 42, 1251. https://doi.org/10.1002/(SICI)1099-1344(19991230)42:13<1251::AID-JLCR281>3.0.CO;2-A
  13. Siele, V. I.; Warman, M.; Leccacorvi. Propellants, Explos., Pyrotech. 1981, 6, 67. https://doi.org/10.1002/prep.19810060304
  14. Salehi, P.; Zolfigol, M. A.; Shirini, F.; Baghbanzadeh, M. Curr. Org. Chem. 2006, 10, 2171. https://doi.org/10.2174/138527206778742650
  15. Minakata, S.; Komatsu, M. Chem. Rev. 2009, 109, 711. https://doi.org/10.1021/cr8003955
  16. Zolfigol, M. A. Tetrahedron 2001, 57, 9509. https://doi.org/10.1016/S0040-4020(01)00960-7