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
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南京理工大学

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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
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1.Nanjing University of Science and Technology;2.Sichuan Huachuan Industry Co., LTD

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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),并深入研究了反应条件,包括溶剂选择,反应温度和反应时间等,化合物3基于ANTA的总收率为35.4%。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其理论爆轰性能。结果表明,化合物3的晶体堆积属于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 °C,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-1; P, 21.3 GPa)。

    Abstract:

    Starting from 5-amino-3-nitro-1,2,4-triazole (ANTA), a new type of energetic compound with a methyl-bridged nitrogen-oxygen heterocyclic ring, the methylene bridging compound 3-((5-amino-3-nitro-1H-1,2,4-triazol-1-yl)methyl)-1,2,4-oxadiazol-5-amine (3), has been synthesized through a three-step reaction. The reaction conditions, including appropriate solvent selection, reaction temperature, and reaction time, were thoroughly investigated and the total yield of 3 was 35.4% based on ANTA. 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 properties of compound 3 were studied by Gaussian software. The results show that the crystal packing of compound 3 belongs to the P21/c monoclinic crystal system, each cell contains four compound 3 molecules (Z = 4), and there are 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 °C, the friction sensitivity is >360 J, and the impact sensitivity is>40 J. The theoretical detonation velocity D is 7196 m·s-1, and the detonation pressure P is 22 GPa, which is better than the traditional explosive TNT (D, 6881 m·s-1; P, 21.3 GPa).

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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,DOI:10.11943/CJEM2025036.

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  • 收稿日期: 2025-02-26
  • 最后修改日期: 2025-04-16
  • 录用日期: 2025-04-24
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