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Preparation of Imidazolium 2,4,5-Trinitroimidazolate from Derivatives of Imidazole and Its Oxidation Under Nitration Conditions

Lian Pengbao, Hou Changming, Chen Lizhen, Xu Jianxin, Xu Zishuai, Wang Jianlong

Central European Journal of Energetic Materials

2022

Vol. 19, no. 4

379--392

In this study, the nitration reactions of imidazole and its nitro derivatives with a mixture of 98% HNO₃ and 98% H₂SO₄ (or 15% SO₃ in H₂SO₄) were reinvestigated. When imidazole or 4(5)-nitroimidazole was nitrated with a mixture of 98% HNO₃ and 98% H₂SO₄ (or 15% SO₃ in H₂SO₄), only 4,5-dinitroimidazole was obtained. Imidazolium 2,4,5-trinitroimidazolate was prepared from 2-nitroimidazole or 2,4(5)-dinitroimidazole with a mixture of 98% HNO₃ and 98% H₂SO₄ (or 15% SO₃ in H₂SO₄); the highest yields were 57.8 and 62.8%, respectively. However, on increasing the reaction temperature, duration, amount of H₂SO₄ or HNO₃, the by-product ethanedioic acid was produced. A possible reaction mechanism for the formation of ethanedioic acid from 2,4,5-trinitroimidazole is suggested. The compounds 4,5-dinitroimidazole, imidazolium 2,4,5-trinitroimidazolate and ethanedioic acid were characterized by infrared spectroscopy, multinuclear ¹H and ¹³C NMR spectroscopy, and elemental analysis. The structures of 4,5-dinitroimidazole and ethanedioic acid were further confirmed by single-crystal X-ray diffraction.

Crystal Structure and Thermal Behaviour of Imidazolium 2,4,5-Trinitroimidazolate

Jian Chen, Pengbao Lian, Lizhen Chen, Jianlong Wang, Jun Chen

Central European Journal of Energetic Materials

2019

Vol. 16, no. 4

547--563

In this work, imidazolium 2,4,5-trinitroimidazolate was obtained from 2,4,5-tri-iodoimidazole in a yield of 48%. Single-crystal X-ray diffraction analysis showed that this compound belongs to the triclinic crystal system with space group P-1. Thermogravimetric-differential scanning calorimetry (TG-DSC) was performed under a nitrogen atmosphere at heating rates of 5, 10, 15 and 20 °C·min−1. Compound 3 clearly exhibits an exothermic decomposition. The activation energy (E) and pre-exponential factor (lnA) calculated by the Kissinger method were 113.67 kJ·mol−1 and 25.30 s−1, respectively. The E values obtained by the FWO and KAS methods changed slightly from 103.33 to 113.69 kJ·mol−1 and from 101.52 to 111.97 kJ·mol−1, respectively, which makes us believe that its thermal decomposition can be described using only one reaction model. The Šatava-Šesták method and the compensation effect were used to study the thermal decomposition mechanism of imidazolium 2,4,5-trinitroimidazolate. [Formula] is regarded as the most appropriate thermal decomposition kinetic equation. The impact sensitivity, friction sensitivity, detonation velocity and explosion pressure of imidazolium 2,4,5-trinitroimidazolate were 43 cm, 46%, 7056.9 m·s−1 and 1.9703 · 1010 Pa (ρ = 1.538 g·cm−3), respectively. Imidazolium 2,4,5-trinitroimidazolate is incompatible with RDX, HMX, TKX-50 and CL-20.