Synthesis, crystallographic characterization, and potential application of fullerene anisole derivatives as nitrocellulose stabilizer

Abstract

A series of fullerene anisole derivative stabilizers was synthesized by nucleophilic substitution reaction using hexachlorofullerene and benzyl alcohol as raw materials to extend the service duration of nitrocellulose (NC)-based propellants. Single-crystal X-ray diffraction, nuclear magnetic resonance, high-resolution mass spectrometry, Fourier transform infrared (FT-IR) spectroscopy, and UV–Vis spectroscopy were used to characterize the structures of the synthesized fullerene anisole derivative stabilizers. Methyl violet, differential scanning calorimetry test, isothermal weight loss, vacuum stability test, and adiabatic accelerated test were used to study their compatibility with NC and their ability to stabilize NC. The results show that the designed and synthesized novel fullerene anisole derivative stabilizer has good compatibility with NC, and their overall stabilizing effects on NC are better than those of the traditional stabilizers, diphenylamine (DPA), and N,N′-dimethyl-N,N′-diphenylurea (C2). The stabilizing effects was ranked as: 3b > 2d > 2a > 2c > C2 > 2b > DPA > NC. In addition, FT-IR analysis and electron spin resonance spectroscopy were applied to explore the stability mechanism of fullerene-based stabilizers to NC. The results reveal that the new fullerene stabilizer can adsorb and effectively eliminate the nitrogen oxide free radicals generated by NC degradation; therefore, it can forbid the autocatalytic degradation of NC and stabilize NC.

Keywords

• Fullerene
• Nitrocellulose
• Stability
• Propellant
• Mechanism