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An Insensitive Energetic Compound 5,7-Diamino-4,6-dinitrobenzotriazol-3-ium-1-oxide: Synthesis, Characterization and Performances
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(Xi′an Modern Chemistry Research Institute, Xi′an 710065)

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    Abstract:

    Using picryl chloride and hydrazine hydrate as the starting materials, an insensitive energetic compound 5, 7-diamino-4, 6-dinitrobenzotriazol-3-ium-1-oxide(2) was synthesized through cyclization and vicarious nucleophilic substitution(VNS) reactions with a total yield of 31.0%. The structures of the title compound and its intermediate were characterized by 1H NMR, 13C NMR, FT-IR and elementary analysis. The reaction condition of VNS was optimized. A cyclization reaction mechanism of 4, 6-dinitrobenzotriazol-3-ium-1-oxide(1) was speculated. The calculations of electrostatic potential(ESP) and molecular orbital of the title compound were performed by quantum chemical method. The detonation properties and thermal property of the titled compound and its intermediate 4, 6-dinitrobenzotriazol-3-ium-1-oxide were studied. Results show that the optimal reaction conditions of VNS were determined as the VNS reagent is NH2OH·HCl, the reaction time at room temperature is 5 h. The titled compound has insensitive characteristic and good thermal stability. The density and thermal stability of compound 2 formed after introducing the two amino groups in compound 1 are improved. Thermal decomposition temperature, density and detonation velocity of two kinds of compounds are 201.3 ℃, 1.73 g·cm-3 and 7371.13 m·s-1 for compound 1 and 248.5 ℃, 1.76 g·cm-3 and 7396.7 m·s-1 for compound 2.

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霍欢,王伯周,翟连杰,等.不敏感含能化合物5,7-二氨基-4,6-二硝基苯并连三唑-1-氧化物的合成、表征与性能(英)[J].含能材料,2016,24(9):857-861.
HUO Huan, WANG Bo-zhou, ZHAI Lian-jie, et al. An Insensitive Energetic Compound 5,7-Diamino-4,6-dinitrobenzotriazol-3-ium-1-oxide: Synthesis, Characterization and Performances[J]. Chinese Journal of Energetic Materials,2016,24(9):857-861.

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History
  • Received:August 21,2015
  • Revised:November 10,2015
  • Adopted:December 01,2015
  • Online: September 19,2016
  • Published: October 10,2016