Issue 41, 2016

Novel trinitroethanol derivatives: high energetic 2-(2,2,2-trinitroethoxy)-1,3,5-triazines

Abstract

The multicomponent reaction of 2,4,6-trichloro-1,3,5-triazine with potassium trinitromethane and trinitroethanol was exploited for the first synthesis of the hetaryl trinitroethyl ether, 2,4-bis(2,2,2-trinitroethoxy)-6-trinitrometyl-1,3,5-triazine 13. The use of compound 13 as a scaffold for the synthesis of substituted trinitroethoxytriazine by sequential nucleophilic substitution processes is described. A number of trinitroethoxytriazines bearing a range of functional groups, including 2,4,6-tris(2,2,2-trinitroethoxy)-1,3,5-triazine 16, have been prepared. There has been no previous incorporation of the trinitroethoxy moiety to a heteroaromatic ring. All trinitroethoxytriazines were fully characterized using IR and multinuclear NMR spectroscopy, elemental analysis, and differential scanning calorimetry (DSC), and, in some cases, 16, 20 and 21, with single crystal X-ray structuring. When compared to the aliphatic trinitroethoxy compounds, the trinitroethoxytriazines show better energetic performance as calculated. The impact sensitivities and ignition points of the novel oxygen and nitrogen-rich triazines were measured. The ability of the applied trinitroethoxytriazines in solid composite propellants as well as in gas generant compositions for airbag inflators was evaluated. The straightforward preparation of these ethers highlights them as valuable new environmentally friendly and high-performing nitrogen and oxygen-rich materials.

Graphical abstract: Novel trinitroethanol derivatives: high energetic 2-(2,2,2-trinitroethoxy)-1,3,5-triazines

Supplementary files

Article information

Article type
Paper
Submitted
04 mar 2016
Accepted
30 mar 2016
First published
01 apr 2016
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2016,6, 34921-34934

Novel trinitroethanol derivatives: high energetic 2-(2,2,2-trinitroethoxy)-1,3,5-triazines

A. A. Gidaspov, V. A. Zalomlenkov, V. V. Bakharev, V. E. Parfenov, E. V. Yurtaev, M. I. Struchkova, N. V. Palysaeva, K. Y. Suponitsky, D. B. Lempert and A. B. Sheremetev, RSC Adv., 2016, 6, 34921 DOI: 10.1039/C6RA05826D

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