Trinitroethyl hydrazides of dicarbonic acids – Energetic compounds with high oxygen and nitrogen content

Many currently used energetic materials need to be replaced with new compounds due to toxicity or other drawbacks. Among these is the oxidizer ammonium perchlorate, often used in solid state propellants, which itself, as well as its combustion products, poses health and environmental issues. Herein, three new polynitro energetic compounds are presented containing trinitroethyl moieties. Starting from easily available starting materials, such as malonic acid ethylester, diglycolic and diaminodiacetic acid, simple and straightforward syntheses were performed to obtain first the corresponding hydrazides and subsequently the trinitroethyl hydrazides in good yields and high purity. These compounds have a positive oxygen balance (assuming to the formation of CO), a high oxygen and nitrogen content and moderate densities. Full characterization was performed by NMR spectroscopy, vibrational analysis and elemental analysis. By using the Gaussian program package, the heats of formation were calculated and the energetic parameters were estimated utilizing the EXPLO5 computer code.