Investigation of synthetic preparations of 5,5’-dinitro-3,3’-azo-1H-1,2,4-triazole (DNAT) and its precursor

Abstract

In the energetic materials field, the need for insensitive high-nitrogen energetic compounds is highly increasing. In this research project, we aim to prepare and investigate three specific synthetic preparations of DNT sodium salt, ANTA, and DNAT, following the reported methods in the literature.1, 2 Our IR and 1H/13C-NMR results indicate that we have successfully synthesized the desired products. DNT sodium salt reaction seems to be exothermic and temperature-sensitive in the first stage of it, which requires a slow addition rate of the DAT and dilute sulfuric acid solution to maintain the temperature low. In addition, the orange residue DNT should be slightly wet and not fully dry in the evaporation stage of the reaction in order to keep this energetic compound more stable and less sensitive. In the ANTA preparations, it has been found that the reaction mixture should be completely free of hydrazine before acidifying it with HCl avoiding the formation of undesired products, which could lead to reaction failure. Best ANTA purification levels were gained by dissolving the product in hot water at 60 °C, and then cooling it in an ice bath for 35 minutes, then filtering and drying. DNAT yield was very low (3.83 %), and its yield and purity alike depend on different experimental conditions, in which lowering the amount of HCl added and applying the potassium permanganate solution addition step in a few minutes might improve both yield and purity.