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.