Introduction of an N-Amino Group onto 4-(Tetrazol-5-yl)-5-nitro-1,2,3-triazole: A Strategy for Enhancing the Density and Performance of Energetic Materials
Xun Huang
a
Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai, 200032, P. R. of China
,
Pinxu Zhao
a
Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai, 200032, P. R. of China
b
School of Chemistry and Chemical Engineering, Nanjing University of Science and Technology, Xiaolingwei Road 200, Nanjing, 210094, Jiangsu, P. R. of China
,
Haifeng Huang∗
a
Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai, 200032, P. R. of China
,
Jun Yang∗
a
Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai, 200032, P. R. of China
› Author AffiliationsThis work was financially supported by the National Natural Science Foundation of China (NSFC) (Grant No. 22175196), the CAS Project for Young Scientists in Basic Research (Grant No.YSBR-052), the Shanghai Science and Technology Committee (20XD1404800) and the Strategic Priority Research Program of the Chinese Academy of Sciences (Grant No. XDB0590000).
2-Amino-5-nitro-4-(tetrazol-5-yl)-1,2,3-triazole (HANTT), its corresponding energetic salts and a dimeric azo compound are successfully synthesized. Compared to 5-nitro-4-(tetrazol-5-yl)-1,2,3-triazole (H2NTT), the neutral N-amino compound HANTT exhibits excellent properties in many aspects, including a higher density (ρ = 1.86 g cm–3), a better detonation performance (Dv = 8931 m s–1, P = 32.2 GPa) and a higher thermal decomposition temperature (Td = 237 °C). Among the prepared materials, the hydroxylammonium energetic salt exhibits the best detonation performance (Dv = 9096 m s–1, P = 32.8 GPa) and an acceptable mechanical sensitivity (IS = 12 J, FS = 144 N). HANTT, the energetic salts and the azo compound are fully characterized by infrared spectroscopy, multinuclear NMR spectroscopy, elemental analysis and differential scanning calorimetry.
36 Tests were conducted according to: UN Recommendations on the Transport of Dangerous Goods, Manual of Tests and Criteria, 5th rev. ed.; United Nations Publications: New York, 2009; 75–82 and 104–107
37
Zhang C,
Wang X,
Huang H.
J. Am. Chem. Soc. 2008; 130: 8359