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Synthesis and Properties of N,N′-Bis(difuroxano [3,4-b:3′,4′-d]phenyl)oxalic Amide

✍ Scribed by Jian-Long WANG; Lian-Ying LÜ; Yu-Xian OU


Publisher
John Wiley and Sons
Year
2008
Tongue
English
Weight
95 KB
Volume
26
Category
Article
ISSN
0256-7660

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✦ Synopsis


Abstract

N,N′‐Bis(difuroxano[3,4‐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 ^1^H 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 (E~a~) and pre‐exponential constant (A) were 226.7 kJ·mol^−1^ and 10^23.17^ s^−1^ respectively. It was presupposed that N,N′‐bis(difuroxano[3,4‐b:3′,4′‐d]phenyl)oxalic amide would be a promising high energetic explosive with low sensitivity.


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