2‐Hydrazonyl‐Propandihydrazide – A Versatile Precursor for High‐Energy Materials

Abstract

In this work, 2‐hydrazonyl‐propandihydrazide (2), a new precursor for energetic materials based on diethyl 2,2‐diazidomalonate (1) was investigated. Therefore, its versatility was shown by various secondary reactions, including formation of energetic salts (3–5), the synthesis of a nitrogen‐rich bistriazole (10) and a highly instable diazido derivative (6). In addition, a Curtius degradation could be observed in detail. When possible, the compounds were analyzed by low temperature X‐ray diffraction. All measurable compounds were analyzed by 1H and 13C NMR spectroscopy, elemental analysis, differential thermal analysis (DTA) and regarding their sensitivity towards impact and friction according to BAM standard techniques. All promising compounds were evaluated regarding their energetic behavior using the EXPLO5 code (V6.05) and compared to RDX and CL‐20. In addition, compound 2 was investigated towards its aquatic toxicity, using the bioluminescent bacteria vibrio fischeri.

Nitraza‐/Oxa‐Propylene‐ and Hydrazonemethylene‐Bridged 1,2,4‐Nitraminotriazoles and Selected Salts

“…Finally, the hydrazono bridged nitraminotriazole, 1,3-bis(3nitramino-4H-1,2,4-triazol-5-yl) hydrazonemethane (BNATHM), available in three steps from diethyl 2,2-diazidomalonate, [23] was converted into four salts 18-21 as shown in Scheme 3. The reaction with the other bases as applied before, did not result in uniform products.…”