Based on the organocatalytic reaction of enamine azide addition of 2,4,6-triazido-1,3,5-triazine to acetylacetone acetoacetic ester, we synthesized a series of previously unknown mono-, di-, and tri(1,2,3-triazolyl)-substituted-1,3,5-triazines that additionally carried carbonyl, ester, and azide groups. The structure of the obtained compounds was proved by NMR (1H, 13C) and IR spectroscopy, and the composition was confirmed by elemental analysis. With the aid of differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA) coupled to mass spectrometry (TG-MS), we obtained data on the thermal behavior and decomposition mechanism for these compounds. We demonstrated that di(1,2,3-triazolyl)-substituted 1,3,5-triazines have an increased thermal stability and have higher values of decomposition onset temperature (220–250 °C) in comparison with tri(1,2,3-triazolyl)-substituted 1,3,5-triazines (180 °C and 160 °C, respectively).
In this study, a high-nitrogen insensitive energetic material, 2-amino-4,5-bis(tetrazole-5-yl)-1,2,3-triazole (H2ABTT), was successfully synthesized by introducing the N-amino group on the 1,2,3-triazole ring. This compound exhibits excellent properties in many aspects. Compared to 4,5-bis(tetrazol-5-yl)-1,2,3-triazole (H3BTT), which has a decomposition temperature (Td) of 277 oC, nitrogen content of 75.11 %, density of 1.69 g cm−3, a detonation velocity of 8630 m s−1, a detonation pressure of 26.3 GPa, an impact sensitivity (IS) of 2 J, and a friction sensitivity (FS) of 240 N, H2ABTT exhibits higher thermal stability of Td:303 oC, higher nitrogen content of N%:76.35 %, higher density of 1.86 g cm−3, more desirable detonation properties (detonation pressure Dv: 9185 m s−1; detonation pressure p: 31.7 GPa), and lower mechanical sensitivities (IS > 100 J; FS > 360 N). Furthermore, H2ABTT outperforms insensitive explosive TATB (Dv = 8179 m s−1; p = 30.5 GPa; IS = 50 J; FS > 360 N) in some properties, making it a potential high-performance insensitive explosive. Besides, energetic salts 4–6 were successfully synthesized based on H2ABTT. The calculated results show that some of these salts even possess higher detonation performance compared to H2ABTT.