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Combinations of furoxan and 1,2,4-oxadiazole for the generation of high performance energetic materials

Dalton Transactions, ISSN: 1477-9234, Vol: 48, Issue: 39, Page: 14705-14711
2019
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Article Description

Several energetic materials, which are composed of furoxan and 1,2,4-oxadiazole backbones, were synthesized by nitrating 3,3′-bis(5-amino-1,2,4-oxadiazol-3-yl)-4,4′-azofuroxan (2) under 100 wt% HNO or 100 wt% HNO/AcO followed by a cation metathesis. All synthesized compounds were fully characterized by multinuclear NMR spectroscopy, IR spectroscopy, and elemental analysis, while 3,3′-bis(1,2,4-oxadiazol-5(4H)-one-3-yl)-4,4′-azofuroxan (3) and diammonium 3,3′-bis(5-nitramino-1,2,4-oxadiazole-3-yl)-4,4′-azofuroxan (4a) were confirmed by single crystal X-ray diffraction. The physicochemical and energetic properties of these compounds including density, thermal stability and sensitivity were investigated. Compounds 3 and 4 have high densities (3: 1.90 g cm, 4: 1.92 g cm), which are comparable to that of HMX (1.91 g cm). All energetic compounds show relatively high calculated heat of formation in the range from 504.79 kJ mol to 1405.62 kJ mol. Their detonation properties were evaluated by EXPLO5 code using the measured density and calculated heat of formation. Among them, compounds 3 and 4 have good detonation performance (3: D = 8891 m s, P = 34.7 GPa, 4: D = 9505 m s, P = 41.3 GPa) and acceptable sensitivities (3: IS = 10 J, 4: IS = 4 J), which indicate their potential applications as high-performance energetic materials.

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