Synthesis and Characterization of Azido Esters as Green Energetic Plasticizers

Three azido‐esters based green energetic plasticizers were synthesized from their chlorides including DEGBAA (diethyleneglycol bis(azidoacetate)), DPGBAA (dipropyleneglycol bis(azidoacetate)) and HETTAA (hexanetriol tris(azidoacetate)). The syntheses were carried out in a two‐step process: the first...

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Bibliographic Details
Published inPropellants, explosives, pyrotechnics Vol. 46; no. 10; pp. 1537 - 1546
Main Authors Nešić, Jovica, Cvijetić, Ilija N., Bogdanov, Jovica, Marinković, Aleksandar
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 01.10.2021
Subjects
Azido esters
Binder
Chemical analysis
Chlorides
Detonation
Dimethyl sulfoxide
Dimethylformamide
Energetic materials
Esterification
Esters
Heat of formation
Infrared analysis
Infrared spectroscopy
Mathematical analysis
NMR
Nuclear magnetic resonance
Physical properties
Plasticizers
Quantum chemical calculations
Quantum chemistry
Rheological properties
Sodium azides
Synthesis
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Summary:Three azido‐esters based green energetic plasticizers were synthesized from their chlorides including DEGBAA (diethyleneglycol bis(azidoacetate)), DPGBAA (dipropyleneglycol bis(azidoacetate)) and HETTAA (hexanetriol tris(azidoacetate)). The syntheses were carried out in a two‐step process: the first step was esterification of glycol or triol using chloroacetyl chloride, and the second step was substitution of chloracetate with sodium azide that yields corresponding azido derivatives. The parameters of synthesis such as molar ratio of hydroxyl and acyl groups, and amount and type of solvent (dimethyl sulfoxide and dimethyl formamide) were optimized to achieve maximal conversion and purity of the products. The obtained products were characterized by elemental analysis, nuclear magnetic resonance (NMR), and infrared vibrational spectroscopy (IR). Thermal and rheological properties were determined using DSC and Modular Compact Rheometer. Condensed phase heat of formation and several properties important for high‐energy materials were predicted from quantum chemical calculations using CBS‐4M method. Detonation and combustion performance of energetic compounds were calculated with the thermochemical computer code EXPLO5V06.05. using the predicted heats of formation and experimentally determined densities as input. The energetic and physical properties of the synthesized compounds were compared to the literature data for common plasticizers.
ISSN:0721-3115
1521-4087
DOI:10.1002/prep.202100105