화학공학소재연구정보센터
Indian Journal of Chemical Technology, Vol.14, No.1, 34-38, 2007
Synthesis and characterization of 1-azido, 2,3-dihydroxy 2-azidomethylpropane (ADMP): A new energetic organic azide
This paper reports file Synthesis of title compound (ADW) for its possible Use as an energetic azido plasticizer The synthesis was carried out by protecting readily available sugar D-mannitol (1) by treating it with acetone in presence of fused FeCl3, at room temperature. leading to the formation of 1,2-5,6 di-O-isopropylidene-D-mannitol (2), which on further oxidation with sodium meta periodate in acetone gave 2,3-O-isopropylidene 1-propanal (3). The subsequent treatment with formaldehyde in presence of base (Aldol-Cannizarro condensation) yielded 2,3-O-isopropylidene 2-hydroxymethyl-l-propanol (4). Tosyl protection (5) of the resulting compounds)followed by introduction of azide substituents gave 2,3-O-isopropylidene-2- azidomethyl-1-propane (6) and finally deprotection of acetonoide functionality using 10% H2SO4 gave title compound (ADMP, 7). All the intermediates and the final product have been characterized by IR and NMR spectra. The differential scanning calorimetry (DSC) study oil ADMP indicated that it undergoes exothermic decomposition ill the temperature in the range of 191-260 degrees C with heat release of the order of 1390 J/g. The theoretical performance parameters suggests its superior energetic in comparison to that of non-energetic plasticizers such as dioctyl phthalate, diamyl phthalate and dibutyl phthalate.