A “Green” Primary Explosive: Design, Synthesis, and Testing

Jie Tang; Dan Chen; Gen Zhang; Hongwei Yang; Guangbin Cheng

doi:10.1055/s-0037-1611696

Synlett, Table of Contents

Synlett 2019; 30(08): 885-892
DOI: 10.1055/s-0037-1611696

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A “Green” Primary Explosive: Design, Synthesis, and Testing

Authors

Jie Tang
Dan Chen
Gen Zhang
Hongwei Yang*

School of Chemical Engineering, Nanjing University of Science and Technology, Xiaolingwei 200, Nanjing, Jiangsu, P. R. of China Email: hyang@mail.njust.edu.cn Email: gcheng@mail.njust.edu.cn
Guangbin Cheng*

School of Chemical Engineering, Nanjing University of Science and Technology, Xiaolingwei 200, Nanjing, Jiangsu, P. R. of China Email: hyang@mail.njust.edu.cn Email: gcheng@mail.njust.edu.cn

Abstract

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Abstract

This account presents the synthesis and the characterization of triazine-tetrazine nitrogen heterocyclic compounds. Some compounds were characterized by NMR and IR spectroscopy, mass spectrometry, differential scanning calorimetry (DSC), and single-crystal X-ray diffraction. The physical and chemical properties were obtained by EXPLO5 v6.01, gas pycnometer, BAM Fallhammer, BAM Friction tester, and several detonation tests. The results show that the new metal-free polyazido compound 3,6-bis-[2-(4,6-diazido-1,3,5-triazin-2-yl)-diazenyl]-1,2,4,5-tetrazine (4) with high heat of formation (2820 kJ mol^–1/6130.2 kJ kg^–1) and excellent detonation velocity and pressure (D = 8602 m s^–1, P = 29.4 GPa) could be used as ingredient in secondary explosives. 3,6-Bis-[2-(4,6-diazido-1,3,5-triazin-2-yl)-hydrazinyl]-1,2,4,5-tetrazine (3) can detonate research department explosive (RDX, cyclonite) as a primer (Δ_f H _m = 2114 kJ mol^–1/4555.2 kJ kg^–1, D = 8365 m s^–1, P = 26.8 GPa), whose initiation capacity is comparable to that of the traditional primary explosive Pb(N₃)₂. Therefore, the metal-free compound 3 can potentially replace lead-based-primary explosives, which would be advantageous for the environment.

1 Introduction

2 Strategies to Form High-Nitrogen Compounds with High Heat of Formation

3 Metal-Free Strategies to Prepare Primary Explosives

4 Concluding Remarks

Key words

high-nitrogen energetic compounds - tetrazines - nucleophilic substitution - metal-free primary explosive

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References

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