CHINESE JOURNAL OF ENERGETIC MATERIALS
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Synthesis and Properties of N,N′-(4,8-Dinitrooctahydrodiimidazo[4,5-b:4′,5′-e] piperazine-2,6(1H,3H)-diylidene)dinitramide
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(Department of Chemistry, Nanjing University of Science and Technology, Nanjing 210094, China)

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    Abstract:

    With glyoxal formamide and guanidine hydrochloride as starting materials,N,N′-(4,8-dinitrooctahydrodiimidazo[4,5-b:4′,5′-e]piperazine-2,6(1H,3H)-diylidene)dinitramide(TNIP) was synthesized by two stages of nitration reaction. The title compound and its intermediates were characterized by IR,NMR and MS. The factors affecting nitration reactions were investigated as well. Results show that the optimized conditions of the first stage of nitration are: V(Ac2O):V(HNO3)=1.2:1,reaction time 2 h and reaction temperature 45 ℃,and for the second stage of nitration,the optimized conditions are: V(Ac2O):V(HNO3)=3:1,reaction time 4h and reaction temperature 50 ℃. Thermal decomposition behavior of TNIP was studied using thermogravimetry and differential scanning calorimetry. The peak temperature is 290 ℃,indicating that TNIP has a better thermal stability. The calculated characteristic drop height of impact sensitivity for TNIP (H50) is 108.1 cm,better than that of RDX(38 cm) and HMX(30-32 cm).

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徐奎,陆明.4,8-二硝基八氢化二咪唑[4,5-b:4′,5′-e]哌嗪-2,6-(1H,3H)-N, N′-二亚硝胺的合成及热性能[J].含能材料,2015,23(8):716-719.
XU Kui, LU Ming. Synthesis and Properties of N, N′-(4,8-Dinitrooctahydrodiimidazo[4,5-b:4′,5′-e] piperazine-2,6(1H,3H)-diylidene)dinitramide[J]. Chinese Journal of Energetic Materials,2015,23(8):716-719.

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History
  • Received:July 14,2014
  • Revised:November 04,2014
  • Adopted:December 12,2014
  • Online: June 29,2015
  • Published: July 15,2015