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Synlett 2019; 30(08): 885-892
DOI: 10.1055/s-0037-1611696
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© Georg Thieme Verlag Stuttgart · New York

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

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
› Author AffiliationsThis work was supported by the National Natural Science Foundation of China (No. 21676147, 21875110), the Science Challenge Project (TZ2018004), and the Natural Science Foundation of Jiangsu Province (BK20150770).
Further Information

Publication History

Received: 21 October 2018

Accepted after revision: 22 November 2018

Publication Date:
05 February 2019 (online)

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A “Green” Primary Explosive: Design, Synthesis, and TestingSynlett 2019; 30(08): e2-e2
DOI: 10.1055/s-0037-1611544

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 (Δf 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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