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Synthesis and Performance of [1,2,5] Oxadiazolo [3,4-b] Pyrazine-5,6-(1H,3H)-dione and its Energetic Salts
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School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, China

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    Abstract:

    [1,2,5] oxadiazole [3,4-b] pyrazine-5,6-(1H,3H)-dione(1) was synthesized directly from 3,4-diaminofurazan and oxalic acid by one-step amide condensation reaction, and the corresponding ionic salts 2-5 were further synthesized by reaction with base. The structures of compounds 1-5 were characterized by infrared spectrum (IR), 1H and 13C nuclear magnetic resonance(NMR). The structures of compounds 1 and 5 were further characterized by X-ray single crystal diffraction. The thermal behaviors of compounds 1-5 were investigated based on differential scanning calorimetry (DSC) measurement. The thermal decomposition temperatures of compounds 1-5 ranged from 210.5 ℃ to 313.5 ℃. The physicochemical properties and detonation performances of compounds 1-5 were estimated by Gaussian 09 program and Explo 5(v. 6.01). The calculated detonation velocities of compounds 1-5 ranged from 7327 m·s-1 to 8555 m·s-1, and the detonation pressures ranged from 20.5 GPa to 30.6 GPa. The impact and friction sensitivities were determined by using BAM technology. The impact sensitivity of compound 1 is 27 J and the friction sensitivity is 280 N. The impact sensitivities of compounds 2-4 are all greater than 40 J and the friction sensitivities of 2-4 are 360 N. The impact sensitivity of sodium salt is 7 J and the friction sensitivity is 120 N. Among them, energetic salts 3 and 4 are expected to be new energetic materials with high energy and low sensitivity.

    表 6 TNT、RDX和目标化合物的物化参数及爆轰性能Table 6 Physiochemical properties and detonation properties of TNT, RDX and compounds 1-5
    表 3 化合物1的氢键的键长和键角Table 3 Hydrogen bond distances(nm)and bond angles for compound 1
    表 5 化合物5的氢键的键长和键角Table 5 Hydrogen bond distances(nm)and bond angles for compound 5
    表 2 化合物1的部分键长和键角Table 2 Selected bond lengths and angles of compound 1
    图3 5 ℃·min-1时化合物1~5的DSC曲线Fig.3 DSC curves of compounds 1-5(5 ℃·min-1 )
    表 4 化合物5的部分键长和键角Table 4 Selected bond lengths and angles of compound 5
    表 1 化合物1和5的晶体学数据Table 1 Crystallographic data for compounds 1 and 5
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肖悠悠,雷才金,杨红伟,等.[1,2,5]噁二唑[3,4-b]吡嗪-5,6-(1H,3H)-二酮及其含能盐的合成及性能[J].含能材料,2022,30(3):236-241.
XIAO You-you, LEI Cai-jin, YANG Hong-wei, et al. Synthesis and Performance of [1,2,5] Oxadiazolo [3,4-b] Pyrazine-5,6-(1H,3H)-dione and its Energetic Salts[J]. Chinese Journal of Energetic Materials,2022,30(3):236-241.

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History
  • Received:July 23,2021
  • Revised:September 26,2021
  • Adopted:January 10,2022
  • Online: March 17,2022
  • Published: March 25,2022