Improved preparation of 3,7-dinitro-1,3,5,7-tetraazabicyclo[3,3,1] nonane (DPT) from urea
Subject Areas : Journal of the Iranian Chemical ResearchMing Lu 1 , Xiaobing Liu, 2 , Xiaoyu Yu 3
1 - Chemical Engineering College, Nanjing University of Science and Technology, Nanjing 210094, China
2 - Chemical Engineering College, Nanjing University of Science and Technology, Nanjing 210094, China
3 - Chemical Engineering College, Nanjing University of Science and Technology, Nanjing 210094, China
Keywords: Urea, 3, 7-dinitro-1, 3, 5, 7-tetraazabicyclo[3, 3, 1]nonane (DPT), Nitration, N, N’- dinitrourea (DNU),
Abstract :
An improved and facile preparation of 3,7-dinitro-1,3,5,7-tetraazabicyclo [3,3,1] nonane(DPT) has been developed starting from urea. In the procedure DPT was synthesized viaN,N’-dinitrourea (DNU) as intermediate and various operating parameters such astemperature, pH and molar ratio of reagents have been optimized to give maximum yield ofthe desired product. The low cost method is concise, operationally simple and offers highpurity and satisfactory yield of DPT.
[1] S. Radhakrishnan, M.B. Talawar, S. Venugopalan, V.L. Narasimhan, J. Hazard. Mater. 152 (2008)
1317-1324.
[2] S. Radhakrisnan, K. Sunil Kumar, T. Soman, V.L. Narasimhan, J. Energ. Mater. 26 (2008) 102-114.
X. Liu & et al. / J. Iran. Chem. Res. 3 (2010) 133-139
139
[3] W.E. Bachmann, W.J. Horton, E.L. Jenner, N.W. Mac Naughton, L.B. Scot, J. Am. Chem. Soc. 73
(1951) 2769-2773.
[4] W.E. Bachmann, E.L. Jenner, J. Am. Chem. Soc. 73 (1951) 2773-2775.
[5] T.C. Castorina, F.S. Holahan, R.J. Graybush, J.V.R. Kaufman, S. Helf, J. Am. Chem. Soc. 82 (1960)
1617-1623.
[6] H.H. Richmond, G.S. Myers, G.F. Wright, J. Am. Chem. Soc. 70 (1948) 3659-3664.
[7] R.A. Strecker, N.J. Randolph, US Pat. (1982) 4338442.
[8] T.L. Davis, K.C. Blanchard, J. Am. Chem. Soc. 51 (1929) 1790-1801.
[9] A.C. Shead, Mikrochim. Acta. 5 (1967) 936-938.
[10] C. Ye, H. Gao, B. Twamley, J.M. Shreeve, New J. Chem. 32 (2008) 317-322.
[11] M. Syczewski, I. Cieslowska-Glinska, H. Boniuk, Propellants Explos. Pyrotech. 23 (1998) 155-158.
[12] A.A. Lobanova, R.R. Sataev, N.I. Popov, S.G. Il’yasov, Russ. J. Org. Chem. 36 (2000) 164-167.
[13] P. Goede, N. Wingborg, H. Bergman, N.V. Latypov, Propellants Explos. Pyrotech. 26 (2001) 17-20.
[14] G. Yong, T. Guo-Hong, J. Young-Hyuk, W. Ruihu, T. Brendan, A.P. Damon, J.M. Shreeve, Energy
Fuels 23 (2009) 4567-4574.
[15] S.G. Il’yasov, A.A. Lobanova, N.I. Popov, R.R. Sataev, Russ. J. Org. Chem. 38 (2002) 1739-1743.
[16] W.J. Chute, D.C. Downing, A.F. Mckay, G.S. Myers, G.F. Wright, Can. J. Research B 27 (1949)
218-223.
[17] A.A. Lobanova, S.G. Il’yasov, N.I. Popov, R.R. Sataev, Russ. J. Org. Chem. 38 (2002) 1-6.
[18] Z. Raszewski, M. Syczewski, Propellants Explos. Pyrotech. 24 (1999) 366-370.