Journal of the American Chemical Society, Vol.141, No.50, 19581-19584, 2019
Bis(3-nitro-1-(trinitromethyl)-1H-1,2,4-triazol-5-yl)methanone: An Applicable and Very Dense Green Oxidizer
Ammonium perchlorate (AP) is most often used as a practical solid rocket propellant because of its excellent performance. However, AP has many short-comings, including instability, high negative enthalpy of formation, and claimed health and environmental issues resulting from its combustion products. The pursuit of highly dense, high-performance, and environmentally friendly oxidizers as solid propellants has long attracted scientists around the world. In this work, bis(3-nitro-1-(trinitromethyl)-1H-1,2,4-triazol-5-yl)methanone (3) was obtained from bis(3-nitro-1H-1,2,4-triazol-5-yl)methane (1) with chloroacetone followed by nitration. The structure of 3 was confirmed by elemental analysis and single-crystal X-ray diffraction. By introducing the carbonyl moiety, the density of 3 was increased to 1.945 g/cm(3) and the decomposition temperature increased to 164 degrees C. Compound 3 is a green energetic oxidizer that has a positive oxygen balance (+8.7%), a high specific impulse (218 s), and an acceptable sensitivity (9 J, 240 N), making it a practical replacement for AP in solid rocket propellant formulations.