CHINESE JOURNAL OF ENERGETIC MATERIALS
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1,2,5-噁二唑桥联双1,2,4-噁二唑化合物的合成及性能
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南京理工大学化工学院,江苏 南京 210094

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国家自然科学基金(22538009, 22505109, 22505110),江苏省自然科学基金(BK20220958), 中国博士后科学基金(2024M764227, 2023M741696), 航天化学动力国家重点实验室开放研究基金项目


Synthesis and Properties of Energetic Compound Based on 1,2,5-Oxadiazole-Bridged Bis(1,2,4-oxadiazole)
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School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, China

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    摘要:

    氧化呋咱由于具有“潜硝基”结构而拥有高能量被广泛研究,但其稳定性相对较差限制了实际应用。本研究以二氰基氧化呋咱为原料,通过还原-肟化-环化缩合反应将氧化呋咱替换为呋咱结构,合成了稳定性更高的新型1,2,5-噁二唑桥联双1,2,4-噁二唑含能化合物 (1),对其硝化后得到3-(4-(5-氨基-1,2,4-噁二唑-3-基)-1,2,5-噁二唑-3-基)-1,2,4-噁二唑-5(4H)-酮(2)。利用核磁共振(NMR)、元素分析(EA)和红外光谱(IR)对新合成的化合物进行了表征。此外,还采用单晶X射线衍射法进一步验证了化合物的准确结构,化合物1(斜方晶系,Pbcn空间群,Z = 4, ρ = 1.825 g·cm?3)与化合物2·3H?O(三斜晶系,P-1空间群,Z = 2, ρ = 1.641 g·cm?3)。化合物1和2的撞击感度均为40 J,摩擦感度为360 N,爆速分别为7921 m·s-1和7660 m·s-1,爆压分别为22.4 GPa和20.5 GPa,均高于传统炸药 TNT(6881 m·s-1, 19.5 GPa)。

    Abstract:

    Furoxan has been extensively studied for its high energy due to its potential "nitro" fragment, but its relatively poor stability limits practical applications. A novel energetic compound, 3,3'-(1,2,5-oxadiazole-3,4-diyl)bis(1,2,4-oxadiazol-5-amine) (1), was synthesized from dicyanofuroxan via a three-step procedure involving reduction, oximation, and cyclization-dehydration. Subsequent nitration afforded 3-(4-(5-amino-1,2,4-oxadiazol-3-yl)-1,2,5-oxadiazol-3-yl)-1,2,4-oxadiazol-5(4H)-one (2). The structures of both compounds were confirmed by nuclear magnetic resonance (NMR) spectroscopy, elemental analysis (EA), and infrared (IR) spectroscopy. Single-crystal X-ray diffraction analyses revealed that compound 1 crystallizes in the orthorhombic space group Pbcn with Z = 4 and a crystal density of 1.825 g·cm?3, whereas the trihydrate of compound 2·3H?O crystallizes in the triclinic space group P?1 with Z = 2 and a density of 1.641 g·cm?3. Both compounds exhibit high insensitivity to mechanical stimuli, with impact sensitivities > 40 J and friction sensitivities > 360 N. Their calculated detonation velocities (7921 m·s?1 for 1 and 7660 m·s?1 for 2) and detonation pressures (22.4 GPa for 1 and 20.5 GPa for 2) are superior to those of TNT (6881 m·s?1, 19.5 GPa).

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朱腾,唐杰,程广斌,等. 1,2,5-噁二唑桥联双1,2,4-噁二唑化合物的合成及性能[J]. 含能材料,.

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  • 收稿日期: 2025-10-15
  • 最后修改日期: 2026-01-09
  • 录用日期: 2026-01-26
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