A Mild Method to Synthesize TATB by Amination of 1,3,5-Trialkoxy-2,4,6- Trinitrobenzene under Phase Transfer Catalysis Conditions

Nucleophilic amination, as a vital step in the synthesis of 1,3,5-triamino2,4,6-trinitrobenzene (TATB) using 1,3,5-trialkoxy-2,4,6-trinitrobenzene (TORTNB) and aqueous ammonia as the starting materials and catalyzed by phase transfer catalysis (PTCs) under mild conditions is described. Various phase transfer catalysts, such as crown ethers, tertiary amines, quaternary ammonium salts, poly ethers and cyclodextrin, and various experimental parameters, such as no. of equivalents of PTC, mole ratio of ammonium hydroxide to the starting material, reaction time, reaction temperature and cycle times of the organic phase were investigated. The crown ethers, especially 18-crown-6, show good catalytic activity and re-usability for the amination of 1,3,5-triethoxy-2,4,6-trinitrobenzene giving a yield of 96.52%. This makes for a safe process and suitable for scale-up, because the reactions are carried out under atmospheric conditions. The material synthesised by the new system was characterized by DSC, SEM and LPS.