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

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,highresolution 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.

Fullerene bisadduct stabilizers:The effect of different addition positions on inhibiting the autocatalytic decomposition of nitrocellulose absorbed nitroglycerin

To explore the effect of different positions and number of pyrrolidine bound to the carbon cage on the stabilization effect of fulleropyrrolidine derivatives to nitrocellulose(NC)/nitroglycerine(NG),we synthesized N-(4-methoxy)phenylpyrrolidine-C_(60) and four different of bis(N-(4-methoxy)phenylpyrrolidine)-C_(60) compounds through Prato reaction.Their structures were characterized by UVevis,^(1)H NMR,^(13)C NMR,high-resolution mass spectroscopy,and single-crystal X-ray diffraction.Their stabilization effect to NC/NG were investigated using differential scanning calorimetry,methyl violet,vacuum stabilization effect,weight loss,and accelerating rate calorimeter tests.The results indicated these compounds had excellent stabilization effect to NC/NG.The stabilization effect of the fulleropyrrolidine bisadducts to NC/NG is significantly better than that of fulleropyrrolidine monoadduct and C_(60).Moreover,the position where pyrrolidine binds to fullerene in fulleropyrrolidine bisadducts is different,and its stabilization effect to NC is also different.The stabilization effect order of different bisadduct isomers to nitrocellulose is as follows:e-edge>trans-2>cis-2>trans-3.Electron paramagnetic resonance(EPR)and FT-IR were used to study the stabilization mechanism of fulleropyrrolidine derivatives to NC/NG.The EPR results also show that fulleropyrrolidine bisadducts with different addition sites have different abilities to absorb nitroxide,and their ability is better than that of the monoadduct and C_(60),which is consistent with the results of stabilization effect performance test.