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, Inhaltsverzeichnis

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

account

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

› Institutsangaben

Abstract

Alle Artikel dieser Rubrik

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

Volltext

Referenzen

References
1 He CL, Shreeve JM. Angew. Chem. Int. Ed. 2016; 55: 772
2 Klapötke TM, Piercey DG, Mehta N, Oyler KD, Jorgensen M, Lenahan S, Salan JS, Fronabarger JW, Williams MD. Z. Anorg. Allg. Chem. 2013; 639: 681
3 Fischer D, Klapötke TM, Stierstorfer J. Angew. Chem. Int. Ed. 2014; 53: 8172
4 Tang YX, He CL, Mitchell LA, Parrish DA, Shreeve JM. Angew. Chem. Int. Ed. 2016; 55: 5565
5 Matyáš R, Pachman J. Primary Explosives . Springer; Berlin, Heidelberg: 2013
6 Fronabarger JW, Williams MD, Sanborn WB, Bragg JG, Parrish DA, Bichayc M. Propellants Explos. Pyrotech. 2011; 36: 541
7 Fischer D, Klapötke TM, Stierstorfer J. Angew. Chem. Int. Ed. 2015; 54: 10299
8 Chen D, Yang HW, Yi ZX, Xiong HL, Zhang L, Zhu SG, Cheng GB. Angew. Chem. Int. Ed. 2018; 57: 2081
9 Fischer D, Gottfried JL. Angew. Chem. Int. Ed. 2016; 55: 16132
10 Singh RP, Gao H, Meshri DT, Shreeve JM. High Energy Density Materials. Springer; Berlin, Heidelberg: 2007
11 Huynh MV, Hiskey MA, Hartline EL, Montoya DP, Gilardi R. Angew. Chem. Int. Ed. 2004; 116: 5032
12 Christe KO, Wilson WW, Sheehy JA, Boatz JA. Angew. Chem. Int. Ed. 1999; 38: 2004
13 Klapötke TM, Martin FA, Stierstorfer J. Angew. Chem. Int. Ed. 2011; 50: 4227
14 Tang YX, Yang HW, Wu B, Ju XH, Lu CX, Cheng GB. Angew. Chem. Int. Ed. 2013; 52: 4875
15 Xu Z, Cheng GB, Yang HW, Ju XH, Yin P, Zhang JH, Shreeve JM. Angew. Chem. Int. Ed. 2017; 56: 5877
16 Kerth J, Lobbecke S. Propellants Explos. Pyrotech. 2002; 27: 111
17 Frumkin AE, Strelenko AM. Russ. Chem. Bull. 2002; 49: 482
18 Chavez DE, Hiskey MA, Naud DL. Org. Lett. 2004; 6: 2889
19 Chavez DE, Hiskey MA, Naud DL. Propellants Explos. Pyrotech. 2004; 29: 209
20 Clayden J, Rowbottom SM, Hutchings MG. Tetrahedron Lett. 2009; 50: 3923
21 Blotny G. Tetrahedron 2006; 62: 9507
22 Kolesinska B, Kaminski ZJ. Tetrahedron 2009; 65: 3573
23 Blotny G. Tetrahedron 2006; 62: 9507
24 Chavez DE, Hiskey MA. Heterocycl. Chem. 1998; 35: 1329
25 Ye CF, Gao HX, Boatz JA, Drake GW, Twamley B, Shreeve JM. Angew. Chem. Int. Ed. 2006; 45: 7262
26 Huynh MH. V, Hiskey MA. Angew. Chem. Int. Ed. 2004; 43: 4924
27 Huynh MH. V, Hiskey MA, Chavez DE. J. Am. Chem. Soc. 2005; 127: 12537
28 Qi C, Li SH, Li YC, Wang Y, Zhao XX, Pang SP. Chem. Eur. J. 2012; 18: 16562
29 Sućeska M. EXPLO5 6 01. Brodarski Institute; Zagreb Croatia: 2013
30 Khasainov B, Comet M, Veyssiere B, Spitzer D. Propellants Explos. Pyrotech. 2017; 42: 547
31 Tests were conducted according to the PRC GJB 5891 27-2006.
32 Tests were conducted according to the PRC GJB 5891 19-2006.
33 Fischer D, Klapötke TM, Stierstorfer J. Angew. Chem. Int. Ed. 2014; 53: 8172