Issue 22, 2023

Synthesis and detonation performance of novel tetrazolyl–triazine nitrogen-rich energetic materials

Abstract

The properties of energetic materials (EMs) are significantly influenced by specific features of their components and including multiple nitrogen-rich (N-rich) heterocycles within a single rigid framework is perhaps one of the most impactful and modern techniques employed in the design and development of novel high-performing explosives. In this regard, coupling tetrazole and s-triazine moieties is an attractive approach given their high nitrogen content and heats of formation resulting from the multiple N–N and/or C–N bonds in their frameworks. With this in mind, herein we report the synthesis of 2,4,6-tris(1H-tetrazol-5-yl)-1,3,5-triazine (H3TTT, 1), a new N-rich (73.7%) EM, along with a series of its salts (3–7). All compounds were physically characterized by IR, multinuclear (1H, 13C) NMR spectroscopy, gas pycnometry, thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). The molecular structure of the TTT3− moiety was confirmed through single-crystal X-ray diffraction (SCXRD) analysis of the triethylammonium (TEA) salt (2). Key energetic parameters were assessed, revealing neutral H3TTT (1) exhibits excellent thermal stability over 247 °C as confirmed through DSC studies, while the decomposition temperatures of the energetic salts (3–7) were found to be lower than the parent material 1 (Tdec ranges from 144 °C (7) to 217 °C (3)). In terms of detonation performance, the highest values were observed for 4 (Pdet = 24.8 GPa, Vdet = 8061 m s−1) and 5 (Pdet = 24.6 GPa, Vdet = 7984 m s−1), as well as for 1 (Pdet = 22.4 GPa, Vdet = 7430 m s−1), where all three outperform TNT (Pdet = 19.5 GPa; Vdet = 6881 m s−1). The results of the thermochemical calculations indicate that H3TTT (1) and its salts 4 and 5 are characterized by ballistic parameters comparable to those of the commonly used JA-2 propellant. By using this simple and straightforward approach to EM development, we have generated a series of materials that may be employed as green alternatives to TNT secondary explosives and low-erosion, environmentally benign high-nitrogen ingredients for gun-propellants.

Graphical abstract: Synthesis and detonation performance of novel tetrazolyl–triazine nitrogen-rich energetic materials

Supplementary files

Article information

Article type
Paper
Submitted
13 7 2023
Accepted
25 10 2023
First published
26 10 2023
This article is Open Access
Creative Commons BY-NC license

Mater. Adv., 2023,4, 5775-5784

Synthesis and detonation performance of novel tetrazolyl–triazine nitrogen-rich energetic materials

P. Richardson, A. A. Kitos, M. Triglav, J. S. Ovens, I. Laroche, S. Delisle, B. Jolicoeur, J. L. Brusso and M. Murugesu, Mater. Adv., 2023, 4, 5775 DOI: 10.1039/D3MA00410D

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