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

Received: 14 May 2021, Revised: 17 May 2021, Accepted: 11 Nov 2021, Available online: 22 Dec 2021, Version of Record: 22 Dec 2021

Ling Liao, Bo Jin, Zhi-cheng Guo, Fei Xian, Chen-jie Hou, Ru-fang Peng
State Key Laboratory of Environment-friendly Energy Materials, School of Materials Science and Engineering, Southwest University of Science and Technology, Sichuan, Mianyang, 621010, China

Abstract


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-C60 and four different of bis(N-(4-methoxy) phenylpyrrolidine)-C60 compounds through Prato reaction. Their structures were characterized by UV–vis, 1H NMR, 13C 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 C60. 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 C60, which is consistent with the results of stabilization effect performance test.
Graphical abstract
The figure describes the stabilization mechanism of fulleropyrrolidine derivatives as stabilizers. Fulleropyrrolidine derivatives absorbed nitrogen oxides produced by NC/NG system in time, and this process substantially weakened the autocatalytic decomposition of NC/NG. In addition, the nitroxide radicals produced by the decomposition of NC/NG were absorbed quickly by fulleropyrrolidine derivatives, thus prolonging the safe storage life of NC/NG.Image 1

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Keywords
Fulleropyrrolidine bisadducts
Stabilization effect
Nitrocellulose/nitroglycerine



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