Fullerene Stabilizer 4,11,15,30-Tetraarylamino Fullerenoarylaziridine: Regioselective Synthesis, Crystallographic Characterization Derivatives, and Potential Application as Propellant Stabilizer

Abstract

The safe storage of propellants has become increasingly challenging because of extreme storage and operational environments. Hence, high-performance stabilizers should be urgently developed to improve the stability of propellants. In consideration of the stability mechanism of stabilizers and the excellent free radical scavenging ability of fullerenes, we synthesized six fullerene stabilizers, 4,11,15,30-tetraarylamino fullerenoarylaziridines, through the nucleophilic substitution reaction of hexachlorofullerene (C 60 Cl 6 ) and corresponding aromatic amines with high yields. Their structures were adequately confirmed by HRMS, FT-IR, UV−vis, 1 H NMR, 13 C NMR spectroscopy, and single-crystal X-ray diffraction. The results of methyl violet test paper and thermogravimetric analysis manifested that the stabilities of these multifunctional fullerene derivatives to nitrocellulose were remarkably better than traditional stabilizers, such as N, N′-dimethyl-N, N′-diphenylurea and diphenylamine. Further electron paramagnetic resonance spectroscopy and FT-IR analysis reasonably revealed that this excellent stability ascribed the efficient scavenging ability for nitroxide radicals produced by nitrocellulose pyrolysis, thereby inhibiting the autocatalytic decomposition of nitrocellulose.

Assessment of the effect of lignin biopolymer on the thermal stability of energetic nitrocellulose/diethylene glycol dinitrate composite

“…Consequently, significant challenges have prompted the scientific community to seek effective alternatives. In this context, some other organic and inorganic chemical substances, such as fullerene-derivatives [1], phenols [11], lignin [12], triphenylamine (TPA), polymers, ketones, N-methyl-pnitroaniline derivatives, ionic liquids [13], natural products [14], zeolites [15], and malonanilides [16], have been tested as stabilizers for nitrate esters. Nevertheless, it is found that the replacement of the classical stabilizers with new compounds presenting less/no effect on the environment and human health is at the expense of the energetic material stability.…”

“…Double base propellants (DBPs) are widely used for solid rocket motors and missile weapons owing to their high energy, wide range of burn rates, and low gas emissions [1]. DBPs are mainly composed of nitrate esters compounds [2].…”