Searching for new thermostable energetic materials: synthesis and characterization of 5-acyl- and 5-sulfonyl-N3-(2,4,6-trinitrophenyl)-(1H-1,2,4-triazole-3,5-diamine) derivatives

摘要

Nitrogen heterocycles are important building blocks in the synthesis of energetic materials. Azole based explosives exhibit not only good stability toward mechanical stimuli but also show increased thermostability. In this study, we present the synthesis of several new amide based nitroderivatives as potential candidates for thermostable energetic materials. Our convenient synthesis way is starting from 2-methoxy-1,3,5-trinitrobenzene. A subsequent controlled microwave-assisted aminolysis reaction with 3,5-diamino-l,2,4-IH-triazole represent a new synthetic procedure for the N3-(2,4,6-trinitrophenyl)-lH-1,2,4-triazole-3,5'-diamine. Further reaction of the obtained 5-aminocompound with acylating agents lead to the synthesis of new energetic derivatives of 5-acyl- and 3-sulfonyl-N3-(2,4,6-trinitrophenyl)-(IH)-1,2,4-triazole-3,5-diamine.The new synthesized compounds were characterized on the basis of HPLC-MS, spectroscopic methods, thermal analysis and flash points determination. The calculated energetic characteristics show that the new HEMs possess a perfect values, which are superior in comparison to the TNT. The data obtained from the thermal analysis and flash point investigation demonstrates a good thermal stability of these synthesized materials. On conclusion, the amide-based derivatization method may be useful for the thermostable materials design. Compounds, synthesized by this way, could serve as promising candidates for the application as thermostable explosives.