Synthesis and Properties of N,N′‐Bis(difuroxano [3,4‐b:3′,4′‐d]phenyl)oxalic Amide |
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Authors: | Jian‐Long WANG Lian‐Ying LÜ Yu‐Xian OU |
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Institution: | 1. School of Chemical Engineering and Environment, North University of China, Taiyuan 030051, China;2. School of Materials Science and Engineering, Beijing Institute of Technology, Beijing 100081, China |
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Abstract: | N,N′‐Bis(difuroxano3,4‐b:3′,4′‐d]phenyl)oxalic amide was synthesized via acylation, nitration, azidation, and pyrolysis‐denitrogenation from the starting materials of oxalyl chloride and 3,5‐dichloroaniline, under mild reaction conditions, with the yields of 81.0%, 82.0%, 86.0% and 81.7% respectively. The title compound and its precursors were characterized by 1H NMR, IR, MS, and elemental analysis. The title compound has a density of 1.92 g·cm?3 by a suspension method, a standard formation enthalpy of 979 kJ·mol?1 calculated by Gaussian programs, a detonation velocity of 8.17 km·s?1, and a detonation pressure of 31 GPa obtained by Kamlet Equation. The thermal decomposition reactions of the title compound at different heating rates were tested by differential scanning calorimetry (DSC). The kinetics parameters of the pyrolysis of the compound were calculated by Kissinger's method. The values of apparent activation energy (Ea) and pre‐exponential constant (A) were 226.7 kJ·mol?1 and 1023.17 s?1 respectively. It was presupposed that N,N′‐bis(difuroxano3,4‐b:3′,4′‐d]phenyl)oxalic amide would be a promising high energetic explosive with low sensitivity. |
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Keywords: | N N′ ‐bis(difuroxano[3 4‐b:3′ 4′ ‐d]phenyl)oxalic amide synthesis explosive thermal property detonation parameter |
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