EXPERIMENTAL INVESTIGATIONS OF 1,4-DI(AZIDOMETHYL)-1′,4′-DIMETHYL-2-TETRAZENE AND 1-AZIDOMETHYL-1′,4,4′-TRIMETHYL-2-TETRAZENE FOR THE REPLACEMENT OF HYDRAZINES IN BIPROPELLANT SYSTEMS-SYNTHESIS AND OPTIMIZATION

摘要

A new azidonation reaction has been realized on 1,1′,4,4′-tetramethyl-2-tetrazene (TMTZ) using iodosylbenzene/trimethylsilyl azide couple (PhIO/TMSN_3). This one-step synthesis has led to two azido derivatives: 1-azidomethyl-1′,4,4′-trimeihyl-2-tetrazene (MATMTZ) and 1,4-di(azidomethyl)-1′,4′-dimethyl-2-tetrazene (DADMTZ). Several conditions were tested such as TMTZ concentration, temperature, and reagent number of equivalents in order to increase the yield of the reaction and to optimize the MATMTZ/DADMTZ ratio. Due to the low thermal stability in solution of these two molecules, we decided to study their decomposition in solution at different temperatures using proton NMR analysis and quantitative NMR. Results showed that DADMTZ is more stable than MATMTZ.