Synthesis and Characterization of 4-(1,2,4-Triazole-5-yl)furazan Derivatives as High-Performance Insensitive Energetic Materials

Zhen Xu; Guangbin Cheng; Hongwei Yang; Jiaheng Zhang; Jean'ne M Shreeve

doi:10.1002/chem.201801597

Synthesis and Characterization of 4-(1,2,4-Triazole-5-yl)furazan Derivatives as High-Performance Insensitive Energetic Materials

Chemistry. 2018 Jul 20;24(41):10488-10497. doi: 10.1002/chem.201801597. Epub 2018 Jun 25.

Authors

Zhen Xu¹, Guangbin Cheng¹, Hongwei Yang¹, Jiaheng Zhang^{2

3}, Jean'ne M Shreeve⁴

Affiliations

¹ School of Chemical Engineering, Nanjing University of Science and Technology, Xiaolingwei, 200, Nanjing, P.R. China.
² State Key Laboratory of Advanced Welding and Joining and Research Centre of Flexible Printed Electronic Technology, Harbin Institute of Technology, Shenzhen, 518055, China.
³ School of Materials Science and Energy Engineering, FoShan University, Guangdong, China.
⁴ Department of Chemistry, University of Idaho, Moscow, ID, 83844-2343, USA.

PMID: 29762890
DOI: 10.1002/chem.201801597

Abstract

3-Nitro-4-(5-nitro-1,2,4-triazol-3-yl)furazan (2), N,N'-bis(trinitroethyl)-3,5'-diamino-4-(1,2,4-triazol-3-yl)furazan (3), N,N'-bis(trinitroethyl)-3,5'-dinitramino-4-(1,2,4-triazol-3-yl)furazan (4) and eighteen nitrogen-rich salts (5 a, 5 b, 5 d-5 i, 5 g-1, 6 a-6 i) were designed and synthesized. These 4-(1,2,4-triazole-5-yl)furazan derivatives were fully characterized by IR and NMR spectra, elemental analysis, and differential scanning calorimetry (DSC). The solid-state structures of 2, 5 d, 5 e, 5 h, 5 g-1, 6 g, and 6 i were confirmed via single crystal X-ray analysis. Detonation performance (detonation velocities and pressures) of these energetic compounds was evaluated and the impact and friction sensitivities were measured using standard BAM technology. Some of the compounds, for example, 2 (D: 9152 m s^-1 , P=37.1 GPa) and 4 (D: 9355 m s^-1 , P=40.1 GPa) exhibit excellent detonation performance, which are comparable to the highly explosive benchmarks such as RDX (D: 8795 m s^-1 , P=34.9 GPa) and HMX (D: 9144 m s^-1 , P=39.2 GPa).

Keywords: 1,2,4-triazole; energetic materials; furazan; heterocycles; nitramine.