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Structure–activity relationship of thermal interaction between arylmalonamide[70]fullerocyclopropane stabilizer and nitrocellulose

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Abstract

The thermal decomposition or even explosion of nitrocellulose during long-term storage is prevented by adding stabilizers to nitrocellulose-based propellants. A series of novel arylmalonamide[70]fullerocyclopropane (3a–c) were synthesized through Bingel reaction. The molecular structures of 3a–c were verified through 1H NMR, 13C NMR, Fourier transform infrared spectroscopy (FT-IR), UV–visible spectroscopy, and mass spectrum. The thermal stability of 3a–c to nitrocellulose was studied by methyl violet paper test and iso-thermogravimetry method, and the results showed that the stability of 3a–c to nitrocellulose was significantly better than that of the [60]fullerene-based stabilizers. The thermal stability of 3a–c to nitrocellulose improved as the increase of the carbon chain length on the p-position of the benzene ring. The effects of 3a–c on the thermal decomposition of nitrocellulose were obtained by differential thermal analysis, and the results showed that the critical temperature of the thermal explosion of nitrocellulose can be increased by 0.1–2.8 °C by 3a–c. The thermal stability of 3a–c to nitrocellulose in adiabatic environment was confirmed by accelerating rate calorimetry. In addition, the stabilization mechanism was studied through ESR and FT-IR, and the results showed that 3a–c can react with nitrogen oxide radicals released by nitrocellulose. These arylmalonamide[70]fullerocyclopropane with excellent thermal stability and strong radical scavenging ability can be used as a promising stabilizer for single and double based propellants.

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Acknowledgments

This work was supported by the financial support received from National Natural Science Foundation of China (51972278), Associated Foundation of Xi’an Modern Chemistry Research Institute (No. 204-J-2020-2634), and Open Project of State Key Laboratory of Environment-friendly Energy Materials (Southwest University of Science and Technology, No. 21fksy19).

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  1. State Key Laboratory of Environment-Friendly Energy Materials, Southwest University of Science and Technology, Mianyang, 621010, Sichuan, China

    Yang Zhao, Bo Jin, Tian Zheng & Rufang Peng

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  1. Yang Zhao
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  2. Bo Jin
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  3. Tian Zheng
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Correspondence to Bo Jin or Rufang Peng.

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Zhao, Y., Jin, B., Zheng, T. et al. Structure–activity relationship of thermal interaction between arylmalonamide[70]fullerocyclopropane stabilizer and nitrocellulose. Cellulose 29, 6579–6593 (2022). https://doi.org/10.1007/s10570-022-04669-5

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