CHINESE JOURNAL OF ENERGETIC MATERIALS
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亚甲基桥联三唑-噁二唑不敏感含能化合物的合成及性能
作者:
作者单位:

1.南京理工大学化学与化工学院;2.四川华川工业股份有限公司

作者简介:

通讯作者:

基金项目:

国家自然科学基金(22305124);江苏省自然科学基金(BK20220967)


Synthesis and Properties of Insensitive Energetic Compound Based on Methyl-Bridged Triazole-Oxadiazole
Author:
Affiliation:

1.School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology;2.Sichuan Huac/huan Industry Co, LTD

Fund Project:

Grant support: National Natural Science Foundation of China (No. 22305124);Natural Science Foundation of Jiangsu Province (No. BK20220967)

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    摘要:

    以5-氨基-3-硝基-1,2,4-三唑(ANTA)为原料,通过三步反应合成新型亚甲基桥联氮氧杂环含能化合物1-((3-氨基-1,2,4-噁二唑-5-基)甲基)-3-硝基-1H-1,2,4-三唑-5-胺(3),并深入研究了溶剂,反应温度和反应时间等反应条件。利用核磁共振(NMR)、傅里叶红外光谱(FT-IR)和元素分析(EA)等方法对化合物1~3进行了表征。同时对化合物3进行了晶体培养和X射线单晶衍射测试,利用真空密度仪、热重-差示扫描量联用仪、撞击/摩擦感度仪等测试仪器,对化合物3进行性能研究,并运用高斯软件研究了其理论爆轰性能。结果表明,化合物3基于ANTA的总收率为35.4%,晶体堆积属于P21/c单斜晶系,每个晶胞包含4个化合物3分子(Z=4),分子内、分子间存在大量氢键,其密度为1.68 g·cm-³,分解温度为232.2 ℃,摩擦感度>360 J,撞击感度>40 J,理论爆速D为7196 m·s-1,爆压P为22 GPa,优于传统炸药TNT(D, 6881 m·s-1P, 21.3 GPa)。

    Abstract:

    By using 5-amino-3-nitro-1,2,4-triazole (ANTA) as raw material, a new methyl-bridged nitrogen-oxygen heterocyclic energetic compound 3-((5-amino-3-nitro-1H-1,2,4-triazol-1-yl)methyl)-1,2,4-oxadiazol-5-amine (3) was synthesized through a three-step reaction. The reaction conditions, including solvent, reaction temperature, and reaction time, were thoroughly investigated. Compounds 1-3 were characterized by nuclear magnetic resonance (NMR), fourier-transform infrared spectroscopy (FT-IR) and elemental analysis (EA). Single crystal X-ray diffraction analysis was also performed on compound 3. The properties of compound 3 were studied by vacuum densitometer, thermogravimetric differential scanning meter and impact/friction sensitivity meter. The theoretical detonation performances of compound 3 were calculated by Gaussian software. Results show that the total yield of compound 3 is 35.4% based on ANTA. The crystal packing of compound 3 belongs to the monoclinic system, space group P21/c, and each cell contains four molecules (Z=4) with a large number of intramolecular and intermolecular hydrogen bonds. The density of compound 3 is 1.68 g·cm-3, the decomposition temperature is 232.2 ℃, the friction sensitivity is above 360 N, and the impact sensitivity is above 40 J. The theoretical detonation velocity and pressure of compound 3 are 7196 m·s-1 and 22 GPa, respectively, which are better than that of the traditional explosive TNT(D, 6881 m·s-1P, 21.3 GPa).

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引用本文

刘尊棋,谭明,易文斌,等.亚甲基桥联三唑-噁二唑不敏感含能化合物的合成及性能[J].含能材料, 2025, 33(5):469-476. DOI:10.11943/CJEM2025036.
LIU Zun-qi, TAN Ming, YI Wen-bin, et al. Synthesis and Properties of Insensitive Energetic Compound Based on Methyl-Bridged Triazole-Oxadiazole[J]. Chinese Journal of Energetic Materials, 2025, 33(5):469-476. DOI:10.11943/CJEM2025036.

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历史
  • 收稿日期: 2025-02-26
  • 最后修改日期: 2025-04-30
  • 录用日期: 2025-04-24
  • 在线发布日期: 2025-04-27
  • 出版日期: 2025-05-25