Green Synthetic Approach for High-Performance Energetic Nitramino Azoles

Abstract

A mild and efficient strategy for the nitration of aminosubstituted pyrazoles/triazole employing a mixture of potassium nitrate and concentrated sulfuric acid (KNO 3 /H 2 SO 4 ) as a nitrating reagent proceeded smoothly to give nitramino-substituted products. These were treated with corresponding bases to give energetic salts 1− 10. The compounds were fully characterized, and single crystal X-ray diffraction studies were obtained for 1, 4, 6, and 10. The physical properties and detonation performance were measured or calculated. Salts 1, 2, 6, 8, and 9 exhibited excellent detonation performance and acceptable sensitivities as well as good stabilities, which suggested that they have potential to be useful as highperformance explosives.

Recent Advances in Synthesis and Properties of Nitrated-Pyrazoles Based Energetic Compounds

“…Moreover, nitrogen-rich heterocycles with a nitramino moiety could exhibit better performance than the corresponding nitro-substituted analogs as above mentioned [ 59 , 68 ]. In 2019, Shreeve and her group [ 69 ] reported a green synthetic route for high-performance nitramino nitropyrazoles. Figure 8 depicted the synthesis of corresponding derivatives, among them the 3,5-dinitramino-4-nitropyrazole ( 16 ) was quite sensitive to mechanical stimulation.…”

Alkaline metal and alkaline earth metal salts of di(1H-tetrazol-5-yl)methanone (DTO): energetic catalysts for ammonium perchlorate decomposition

“…Oxygen balance is a critical factor for the performance of energetic materials. [18][19][20] Di(1H-tetrazol-5-yl)methanone (DTO) introduces carbonyl group as bridge moiety, resulting in better oxygen balance and a higher molecular density.…”

Synthesis and Investigation of 2,4,6‐Trinitropyridin‐3‐ol and its Salts

“…The order of increase of detonation performance is 1 < 2 < 3, on the contrary, the order in which the value of impact sensitivity increases is 3 < 2 < 1. Thus, the contradiction among thermal stability, detonation performance, and sensitivity has not been solved [8][9][10].…”

“…In addition, their properties are readily improved and optimized through judicious combination of different anions and cations, as well as a result of independent modification of cationic and anionic components [5–7]. With regard to energetic ionic salts, the following energetic compounds have been widely noted: Dihydroxylammonium (4,4’‐dinitro 1H,1’H‐[3,3’‐bipyrazole]‐5,5’‐diyl)bis(nitroamide) ( 1 ) [8], Hydroxylammonium(3,4‐dinitro‐1H‐pyrazol‐5‐yl)(nitro)amide ( 2 ) [9], Dihydroxyl ammonium 3,4‐di(nitra‐mino)furazan ( 3 ) [10–11] (Figure 1).…”