| Adamantane and its derivatives are one of the most important organic compounds, which can be widely used in drugs, functional polymers and energetic materials. Polynitroadamantanes and polynitroxyadamantanes, have high energy density and good stability, might act as the candidates of energetic compounds.In this dissertation,2-nitro-2-azaadamantane-4,8-diyl dinitrate, a new energetic cage compound, was synthesized with a total yield of 27% from bicyclo[3.3.1]nonane-2,6-dione via hydrazonation, elimination, epoxidation, cyclization, acetylation and nitration. Reaction conditions for the elimination, epoxidation and nitration were optimized. The structures of the target compound and intermediates were determined by 1H NMR,13C NMR, FT-IR and elementary analysis. The thermal stability of target product was studied by thermogravimetry (TG) and differential scanning calorimetry (DSC). The results show that the decomposition starts from 170.0℃ and the decomposition peak temperature is 193.7 ℃, which indicates that it has good thermal stability. The detonation properties were predicted by Kamlet-Jacobs formula and the results show that the density, detonation velocity, detonation pressure of the target compound are 1.71 g·cm-3,5780 m·s-1,11.0 GPa respectively.The synthesis of 1,2,2,5,6,6-hexanitroadamantane, a new cage compound, was investigated.2,6-dioxoadamantane-1,5-dicarbonyl azide, an intermediate of 1,2,2,5,6,6-hexanitroadamantane, was synthesized via several steps using bicyclo[3.3.1] nonane-2,6-dione as the starting materials. The strategy offers the reference for the synthesis of other polynitroadamantanes.2-nitro-2-azaadamantane-4,8-diyl dinitrate, a new energetic cage compound, was synthesized in this paper, which might be used in the formula of explosives and propellants. The synthesis of 1,2,2,5,6,6-hexanitroadamantane was also tried in the dissertation. The methods paved mild and prospective ways for the synthesis of other polynitro cage compounds. |
PDF Full Text Request