Synthesis and Properties of N¹, N³‐di (2,4‐dinitrophenyl) −2‐fluoro‐1,3‐diamino‐4,6‐ Dinitrobenzene and its Analogues

Abstract

Polynitrobenzene compounds are a type of heat‐resistant explosives with excellent thermal stability. This study reported three novel energetic compounds, namely compounds N1, N3‐bis(2,4‐dinitrophenyl)‐2‐fluoro‐4,6‐dinitrobenzene‐1,3‐ diamine (3), 2‐fluoro‐4,6‐dinitro‐N1,N3‐bis(2,4,6‐trinitrophenyl)benzene‐1,3‐ diamine (4), and 2‐chloro‐4,6‐dinitro‐N1,N3‐bis(2,4,6‐trinitrophenyl)benzene‐1,3‐ diamine (6). The target compounds were prepared with commercially available 2,3,4‐trifluoronitrobenzene and 2,3,4‐trichloronitrobenzole. The crystalline structures of compounds 3, 4, and 6 were determined by single‐crystal X‐ray diffraction, and the crystal densities (ρ) were calculated to be 1.7585 g cm−3, 1.6651 g cm−3, and 1.7371 g cm−3, respectively. Based on the calculated standard molar enthalpy of formation and crystal densities, the Chapman–Jouguet detonation properties of 3, 4, and 6 were predicted. Their enthalpy of formation (ΔHf), detonation velocities (D), and detonation pressures (P) were in the ranges of 110.1 kJ mol−1 to 349.9 Kj mol−1, 7264 m s−1 to 7770 m s−1, and 21.8 GPa to 25.9 GPa, respectively. Notably, the density, thermal decomposition temperature, detonation velocity, detonation pressure, and impact sensitivity value of compound 3 were 1.76 g cm−3, 313°C, 7546 m s−1, 24.2 GPa, and 16 J, respectively, suggesting that compound 3 is a high‐performance heat‐resistant explosive.