Journal of Molecular Modeling

, 25:346 | Cite as

Theoretical study on the mechanisms of the decomposition of nitrate esters and the stabilization of aromatic amines

  • Yang Sun
  • Shuang Ni
  • Xiu-mei PanEmail author
Original Paper


The nitrate esters are important components of double-base propellants. Aromatic amines are recommended as the stabilizers to delay the decomposition of nitrate esters and increase their storage time. The decomposition mechanisms of alkyl, alkoxy dinitrate, and poly-fluoride nitrate esters and the stabilizing effect of aromatic amines including new designed phenols are studied at the level of B3LYP/6-31G**. Alkyl and alkoxyl dinitrate esters are likely to be transformed by hydrogen abstraction, which is consistent with that of mononitrate and trinitrate esters. However, for poly-fluoride nitrate esters, NO2 catalyzed self-decomposition is preferred. In addition, comparing with mononitrate and trinitrate esters, the order of their stability is mononitrates > dinitrates > trinitrates. Poly-fluoride nitrate esters have a poorer stability than non-fluorinated nitrate esters. Comparing with parent nitrate esters, the stability of new designed poly-fluoride oxygen-containing nitrate esters is slightly improved. Aromatic amines including new designed phenols are effective stabilizers of nitrate esters, especially when introduced hydroxyl in the para position, can enhance the effects of stabilizers. The rate constants for the decomposition of nitrate esters and the bimolecular reaction between stabilizers and NO2 are calculated by using traditional transition state theory.

Graphical abstract

Comparison between the reaction energy barrier of nitrate esters and stabilizers with NO2


Nitrate esters Decomposition Stabilizers Rate constants 


Funding information

This work was supported by the fund of key technology research and development projects (20190302130GX), Jilin Province Science and Technology Department.

Supplementary material

894_2019_4245_MOESM1_ESM.docx (3.3 mb)
ESM 1 (DOCX 1723 kb)


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Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Institute of Functional Material Chemistry, National & Local United Engineering Lab for Power Battery, Faculty of ChemistryNortheast Normal UniversityChangchunPeople’s Republic of China

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