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Polynitro-1,2,4-triazole Energetic Materials with <i>N</i>-Amino Functionalization

Xinyang Lu, Xiangyang Lin, Haifeng Huang, Jun Yang

2024The Journal of Organic Chemistry13 citationsDOI

Abstract

Trinitromethyl and N -amino groups were innovatively incorporated into the framework of 1,2,4-triazole, resulting in 1-amino-5-nitro-3-(trinitromethyl)-1,2,4-triazole ( 2 ). Ammonium and hydrazinium salts of 1-amino-5-nitro-3-(dinitromethyl)-1,2,4-triazole were synthesized by acidification, extraction, and neutralization with bases from the potassium salt. All of the newly prepared energetic compounds were comprehensively characterized by using infrared spectroscopy, elemental analysis, nuclear magnetic resonance spectroscopy, and single crystal X-ray diffraction. Compound 2 exhibits favorable properties such as positive oxygen balance (OB CO2 = 5.8%), high density (1.88 g cm –1 ), good detonation performances ( v D = 8937 m s –1, P = 35.5 GPa), and appropriate friction sensitivity (FS = 144 N). The potassium salt 3 demonstrates good thermal decomposition temperature (181 °C) and high density (1.98 g cm –1 ), while the ammonium salt and hydrazinium salt also display good thermal decomposition temperatures of 183 and 176 °C, respectively. Among these compounds, the ammonium salt exhibits the lowest mechanical sensitivities (FS = 144 N, IS = 6 J).

Topics & Concepts

Surface modification1,2,4-TriazoleChemistryCombinatorial chemistryMedicinal chemistryPhysical chemistryEnergetic Materials and CombustionChemical Reactions and MechanismsThermal and Kinetic Analysis