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5433127 
Journal Article 
Synthesis and characterization of 1-azido, 2,3-dihydroxy 2-azidomethylpropane (ADMP): A new energetic organic azide 
Karanjule, NS; Talawar, MB; Sivabalan, R; Gore, GM; Dhavale, DD; Asthana, SN 
2007 
Yes 
Indian Journal of Chemical Technology
ISSN: 0971-457X 
NATL INST SCIENCE COMMUNICATION 
NEW DELHI 
14 
1 
34-38 
English 
WOS:000244670500005 
This paper reports the synthesis of title compound (ADMP) 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-1-propanol (4). Tosyl protection (5) of the resulting compound 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 on ADMP indicated that it undergoes exothermic decomposition in the temperature in the range of 191-260°C with heat release of the order of 1390 J/g. The theoretical performance parameters suggest its superior energetic in comparison to that of non-energetic plasticizers such as dioctyl phthalate, diamyl phthalate and dibutyl phthalate. 
ADMP; Aldol-Cannizarro condensation; theoretical performance; energetic azido plasticizer