Synthesis and pyrolysis studies of bis(nitratomethyl)-1,3-bishomocubane—A high-energy high-density liquid

The synthesis and thermal decomposition of the energetic material, bis(nitratomethyl)-1,3-bishomocubane (DNMBHC) were undertaken. The optimized structure of DNMBHC was obtained by ab initio methods and was utilized to calculate the heat of formation, heat of combustion and detonation properties. The slow thermal decomposition of DNMBHC was investigated by thermogravimetric analysis (TGA) at heating rates of 10 °C/min, while fast pyrolysis was investigated utilizing sub-milligram quantities at heating rates of 100 °C/s. The gaseous products from fast pyrolysis were detected by rapidscan FTIR spectroscopy to postulate probable decomposition pathways. The primary decomposition pathway was found to involve Osingle bondNO2 bond scissions to form NO2, subsequently leading to several secondary reactions. A secondary pathway involving detachment of the nitrate ester group from the ring to form MeONO2 was also predicted. The products involving the bishomocubane ring were found to be relegated to the condensed phase.