Advertisement

Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

Interaction of nitrocellulose with pentaacyloxyphenyl fullerene derivatives: autocatalytic inhibition in thermal decomposition of nitrocellulose

  • 19 Accesses

Abstract

The safe storage of nitrocellulose has become challenging due to their requirements of extreme storage environments, and existing stabilizers cannot fully meet the demand. Thus, developing new high-performance stabilizers to improve the stability of nitrocellulose is urgently needed. Considering the stabilizing mechanism of stabilizers and the excellent free radical scavenging ability of fullerenes, two novel fullerene-based stabilizers, pentaacyloxyphenyl fullerene derivatives (PAOP-C60), were designed and synthesized, and their structures were characterized by FTIR, UV–Vis and NMR. The thermal action of PAOP-C60 during thermal decomposition process of nitrocellulose was studied by thermal analysis, which indicating that the thermal stability of nitrocellulose was increased with addition of PAOP-C60 and the PAOP-C60 was found to exhibit superior thermal stability than traditional stabilizer. The results of electron spin resonance showed that fullerene-based stabilizers had a significant scavenging effect on nitrogen oxide radicals, and the IC50 of PAOP-C60 (0.674–0.818 g L−1) was smaller than that of diphenylamine (1.717 g L−1). Moreover, the intermediate product produced by PAOP-C60 and nitrocellulose action was extracted and characterized by FTIR. A possible stabilization mechanism of PAOP-C60, which was different from traditional stabilization mechanism, was proposed.

This is a preview of subscription content, log in to check access.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11

References

  1. Bhattacharya A (2005) A general kinetic model framework for the interpretation of adiabatic calorimeter rate data. Chem Eng J 110:67–78

  2. Birkett PR, Avent AG, Darwish AD, Kroto HW, Walton DRM (1993) Preparation and 13C NMR spectroscopic characterisation of C60Cl6. J Chem Soc, Chem Commun 24:1230–1232

  3. Birkett PR, Avent AG, Darwish AD, Hahn I, Kroto HW, Langley GJ, Loughlin JO, Taylor R, Walton DRM (1997) Arylation of [60]fullerene via electrophilic aromaticsubstitution involving the electrophile C60Cl6: frontside nucleophilic substitution of fullerenes. J Chem Soc Perkin Trans 2(6):1121–1126

  4. Dong Y, Hiroshi H, Kazutoshi K (2003) Predicting the self-accelerating decomposition temperature (SADT) of organic peroxides based on non-isothermal decomposition behavior. J Loss Prev Process Ind 16:411–416

  5. Drzyzga O (2003) Diphenylamine and derivatives in the environment: a review. Chemosphere 53:809–818

  6. Fryš O, Bajerová P, Eisner A, Skládal J, Ventura K (2011) Utilization of new non-toxic substances as stabilizers for nitrocellulose-Based propellants. Propellants Explosives Pyrotech 36:347–355

  7. Gharbi N, Pressac M, Hadchouel M, Szwarc H, Wilson SR, Moussa F (2005) [60]Fullerene is a powerful antioxidant in vivo with no acute or subacute toxicity. Nano Lett 5:2578–2585

  8. Hare JP, Kroto HW, Taylor R (2013) Reprint of: preparation and UV/visible spectra of fullerenes C60 and C70. Chem Phys Lett 589:57–60

  9. Hassan MA, Shehata AB (2010) Studies on some acrylamido polymers and copolymer as stabilizers for nitrocellulose. J Appl Polym Sci 85:2808–2819

  10. He Y, Liu J, Li P, Chen M, Wei R, Wang J (2017) Experimental study on the thermal decomposition and combustion characteristics of nitrocellulose with different alcohol humectants. J Hazard Mater 340:202–210

  11. Heil M, Kerstin W, Manfred AB (2017) Characterization of gun propellants by Longmilerm mass loss measurements. Propellants Explosives Pyrotech 42:706–711

  12. Hussien AE, Elbeih A, Klapötke TM, Krumm B (2018) Higher performance and safer handling: new formulation based on 2,2,2-trinitroethyl-formate and nitrocellulose. ChemPlusChem 83:128–131

  13. Jain S, Park W, Chen YP, Qiao L (2016) Flame speed enhancement of a nitrocellulose monopropellant using graphene microstructures. J Appl Phys 120:370–418

  14. Katoh K, Yoshino S, Kubota S, Wada Y, Ogata Y, Nakahama M, Kawaguchi S, Arai M (2010) The effects of conventional stabilizers and phenol compounds used as antioxidants on the stabilization of nitrocellulose. Propellants Explosives Pyrotech 32:314–321

  15. Klerk D, Wim PC (2015) Assessment of stability of propellants and safe lifetimes. Propellants Explosives Pyrotech 40:388–393

  16. Krumlinde P, Tunestål SEE, Hafstrand A (2016) Synthesis and characterization of novel stabilizers for nitrocellulose-based propellants. Propellants Explosives Pyrotech 42:78–83

  17. Krusic PJ, Wasserman E, Keizer PN, Morton JR, Preston KF (1991) Radical Reactions of C60. Science 254:1183–1185

  18. Kubota N (2010) Role of additives in combustion waves and effect on stable combustion limit of double-base propellants. Propellants Explosives Pyrotech 3:163–168

  19. Lindblom T (2002) Reactions in stabilizer and between stabilizer and nitrocellulose in propellants. Propellants Explosives Pyrotech 27:197–208

  20. Luo LQ, Jin B, Chai ZH, Huang Q, Chu SJ, Peng RF (2019a) Interaction and mechanism of nitrocellulose and N-methyl-4-nitroaniline by isothermal decomposition method. Cellulose 26:9021–9033

  21. Luo LQ, Jin B, Xiao YY, Zhang QC, Chai ZH, Huang Q, Chu SJ, Peng RF (2019b) Study on the isothermal decomposition kinetics and mechanism of nitrocellulose. Polym Test 75:337–343

  22. Merzhanov AG, Abramov VG (2010) Thermal explosion of explosives and propellants. Propellants Explosives Pyrotech 6:130–148

  23. Morley D, Keefer LK (1993) Nitric oxide/nucleophile complexes: a unique class of nitric oxide-based vasodilators. J Cardiovasc Pharmacol 22:3–9

  24. Ossa M, López-López M, Torre M, García-Ruiz C (2011) Analytical techniques in the study of highly-nitrated nitrocellulose. TrAC Trends Anal Chem 30:1740–1755

  25. Purves CB, Grassie VR, Mitchell L, Pepper JM (1950) Preliminary tests on possible new stabilizers for nitrocelluloses. Can J Res 28:468–484

  26. Saunders CW, Taylor LT (1990) A review of the synthesis, chemistry and analysis of nitrocellulose. J Energ Mater 8:149–203

  27. Tang Q, Fan X, Li J, Bi F, Fu X, Zhai L (2016) Experimental and theoretical studies on stability of new stabilizers for N-methyl-P-nitroaniline derivative in CMDB propellants. J Hazard Mater 327:187–196

  28. Taylor R, Walton DRM (1993) The chemistry of fullerenes. Nature 363:685–693

  29. Trache D, Tarchoun AF (2018) Stabilizers for nitrate ester-based energetic materials and their mechanism of action: a state-of-the-art review. J Mater Sci 53:100–123

  30. Tsang W, Herron JT (1991) Chemical kinetic data base for propellant combustion I. reactions involving NO, NO2, HNO, HNO2, HCN and N2O. J Phys Chem Ref Data 20:609–663

  31. Wang B, Xin L, Wang Z, Deluca LT, Liu Z, You F (2017) Preparation and properties of a nRDX-based propellant. Propellants Explosives Pyrotech 42:649–658

  32. Wiegand DA, Nicolaides S, Pinto J (1990) Mechanical and thermomechanical properties of NC base propellants. J Energ Mater 8:442–461

  33. Wilker S, Heeb G, Vogelsanger B, Petržílek J, Skládal J (2007) Triphenylamine-a ‘New’ stabilizer for nitrocellulose based propellants-part I: chemical stability studies. Propellants Explosives Pyrotech 32:135–148

Download references

Acknowledgments

This work was supported by the financial support received from the Key Projects of the Pre-research Fund of the General Armament Department (Project No. 6140720020101), National Natural Science Foundation of China (51572230), Outstanding Youth Science and Technology Talents Program of Sichuan (No. 19JCQN0085), National Defense Technology Foundation Project (Project No. JSJL2016404B002) and the Institute of Chemical Materials, China Academy of Engineering Physics.

Author information

Correspondence to Bo Jin or Rufang Peng.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Zhao, Y., Jin, B., Peng, R. et al. Interaction of nitrocellulose with pentaacyloxyphenyl fullerene derivatives: autocatalytic inhibition in thermal decomposition of nitrocellulose. Cellulose (2020). https://doi.org/10.1007/s10570-020-03027-7

Download citation

Keywords

  • Nitrocellulose
  • Fullerene derivative
  • Stabilizer
  • Radical scavenger
  • Thermal analysis