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Synthesis of 1-(2H-tetrazol-5-yl)-5-nitraminotetrazole and its derivatives from 5-aminotetrazole and cyanogen azide: a promising strategy towards development of C-N linked bistetrazolate energetic materials

Abstract

A series of C-N linked bistetrazolate nitramino compounds, i.e., 1-(2H-tetrazol-5-yl)-5-nitraminotetrazole (2) and its energetic salts (3-8), were successfully prepared from readily available 5-aminotetrazole. All new energetic compounds were fully characterized by IR, NMR spectra and elemental analysis, and six of them (1, 3-7) were further determined by single-crystal X-ray diffraction analysis. The nitrogen contents of these energetic bistetrazolate compounds, ranging from 59.3% (3) to 74.8% (7), are much higher than those of the commonly used high explosives such as RDX (N: 37.8%), HMX (N: 37.8%) and CL-20 (N: 38.3%). And theoretical calculations by using Gaussian 09 program package demonstrate compounds 1-8 have high positive heats of formation, which the heats of formation of ammonium salt 4 (3.60 kJ g-1), aminonitroguanidinium 5 (3.11 kJ g-1) and dihydrazinium salt 7 (3.25 kJ g-1) are approximately eight times higher than those of RDX (0.39 kJ g-1), HMX (0.39 kJ g-1), and four times higher than that of CL-20 (0.83 kJ g-1). The high nitrogen contents and high heats of formation have endowed these energetic compounds with prominent detonation performance. It is noteworthy that compound 7 exhibits an excellent calculated detonation velocity of 9822 m s-1 superior to that of CL-20 (9730 m s-1), while impact and friction sensitivities of 7 (IS = 8 J, FS = 192 N) are comparable to that of HMX (IS = 7 J, FS = 112 N). The good detonation properties with moderate sensitivities demonstrate compound 7 is a promising candidate for applications as high-performance energetic materials.

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Publication details

The article was received on 07 Jul 2017, accepted on 12 Sep 2017 and first published on 12 Sep 2017


Article type: Paper
DOI: 10.1039/C7TA05905A
Citation: J. Mater. Chem. A, 2017, Accepted Manuscript
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    Synthesis of 1-(2H-tetrazol-5-yl)-5-nitraminotetrazole and its derivatives from 5-aminotetrazole and cyanogen azide: a promising strategy towards development of C-N linked bistetrazolate energetic materials

    Q. Zhang, B. Wang, X. Qi, W. Zhang, K. Wang and W. Li, J. Mater. Chem. A, 2017, Accepted Manuscript , DOI: 10.1039/C7TA05905A

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