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Title: Synthesis and characterization of 1-azido, 2,3-dihydroxy 2-azidomethylpropane (ADMP): A new energetic organic azide
Authors: Karanjule, N S
Talawar, M B
Sivabalan, R
Gore, G M
Dhavale, D D
Asthana, S N
Keywords: ADMP;Aldol-Cannizarro condensation;Theoretical performance;Energetic azido plasticizer
Issue Date: Jan-2007
Publisher: CSIR
IPC Code: C07C247/00
Abstract: 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 191-260ºC 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.
Page(s): 34-38
ISSN: 0971–457X
Appears in Collections:IJCT Vol.14(1) [January 2007]

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