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Z. Naturforsch. 2014,
69b, 77 – 82
doi:10.5560/ZNB.2014-3160
Improved Synthesis and Characterization of 2-(Dinitromethylene)-1-nitro-1,3-diazacyclopentane
1 School of Chemical & Environmental Engineering, Beijing Institute of Technology, 100081, Beijing, P. R. China
2 Xi'an Modern Chemistry Research Institute, 710065, Xi'an, P. R. China
Reprint requests to Prof. Meng Zihui. Tel. & Fax: 86-10-68913065. E-mail:
m_zihui@yahoo.com.
Received May 26, 2013 / published online December 30, 2013
A new approach is described to synthesize 2-(dinitromethylene)-l-nitro-1,3-diazacyclopentane (4). 2-(Dinitromethylene)-1,3-diazacyclopentane (1) was synthesized first by the nucleophilic substitution of ethylenediamine and 1,1-diamino-2,2-dinitroethylene (FOX-7) catalyzed by Mg(OAc)2, then 1 was transformed to 4 through nitration, reduction and hydrolysis. The crystal morphology of 4 was investigated by scanning electron microscopy (SEM). Compound 4 was also characterized by IR, NMR, MS and elemental analysis, and by thermogravimetry (TG) and differential scanning calorimetry (DSC), which revealed that 4 decomposes at 126 °C. The explosive performance of 4 was calculated using the VLW equation. The crystal density of 4 was determined as 1.79 g · cm−3. The experimental
results indicate that 4 is sensitive towards impact and spark stimuli, but insensitive to friction.
Key words: 2-(Dinitromethylene)-1,3-diazacyclopentane, Thermal Stability, Energetic Material