A Dihydrazone as a Remarkably Nitrogen-Rich Thermostable and Insensitive Energetic Material

Hydrogen bonds (H-bonds) in energetic compounds have a very pronounced effect on physicochemical properties such as density, thermal stability, sensitivity, and solubility. Now a strategy to synthesize nitrogen-rich energetic materials with overall good properties, which stem from the synergetic effects of inter- or intramolecular H-bonds, is reported. 1,2-Dihydrazono-1,2-di(1H-tetrazol-5-5-yl)ethane (4), a new thermostable and insensitive material, is obtained from the reaction of dioxime (2) with hydrazine hydrate. The exchange of the oxime (NOH) with the hydrazone (NNH₂) functionality results in the reduced acidic character and low solubility in water, which make it remarkably suitable for practical use. While the detonation velocity of 4 is comparable with RDX, it has an advantage of high nitrogen content (76%) and high thermal stability (275 °C) and is insensitive toward external stimuli.