Английская Википедия:Bis-oxadiazole

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Bis-oxadiazole, or more formally known as bis(1,2,4-oxadiazole)bis(methylene) dinitrate, is a nitrated heterocyclic compound of the oxadiazole family.[1]

Bis-oxadiazole is related to bis-isoxazole tetranitrate (BITN), which was developed at the United States Army Research Laboratory (ARL). With a high nitrogen content, these compounds are poised to release a large volume of very stable N2.[2] It is a “melt-cast” explosive material that is potentially both more powerful and environmentally friendly alternative to TNT.[3]

Synthesis

Glyoxal condenses with hydroxylamine to yield diaminoglyoxime (DAG). Treating DAG with methyl glycolate in the presence of base at high temperature yields bis(1,2,4-oxadiazole).[4]

Replacement for TNT

TNT is attractive explosive because it is a melt-castable. A low melting point of about 80 °C and high decomposition temperature of 295 °C allows manufacturers to safely pour TNT into molds. The production of TNT generates hazardous waste, e.g. red water and pink water.[1]

Bis-oxadiazole, which is also melt-castable, is about 1.5 times more powerful than TNT and yet produces less hazardous wastes.[1]

Physical Properties of Bis-oxadiazole Compared to TNT[4]
Physical Property bis-oxadiazole TNT
Onset temperature of melting 84.5 °C 80.4 °C
Onset temperature of decomposition 183.4 °C 295.0 °C
Derived density from X-ray data 1.832 g cm−3 1.65 g cm−3
Detonation pressure 29.4 GPa 20.5 GPa
Detonation velocity 8180 m s−1 6950 m s−1
Molar enthalpy of formation -79.4 kJ mol−1 -59.3 kJ mol−1

A major challenge in the production of bis-oxadiazole is its low yield.[5]

References

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