Synthesis and Characterization of Azido Esters as Green Energetic Plasticizers
Abstract
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 proper...ties 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.
Keywords:
Azido esters / Binder / Energetic materials / Plasticizers / Quantum chemical calculationsSource:
Propellants, Explosives, Pyrotechnics, 2021, 46, 10, 1537-1546Publisher:
- Wiley
Note:
- Supplementary material: https://cherry.chem.bg.ac.rs/handle/123456789/4613
Related info:
- Referenced by
https://cherry.chem.bg.ac.rs/handle/123456789/4613
DOI: 10.1002/prep.202100105
ISSN: 0721-3115
WoS: 000681569000001
Scopus: 2-s2.0-85111829278
URI
https://onlinelibrary.wiley.com/doi/abs/10.1002/prep.202100105https://cherry.chem.bg.ac.rs/handle/123456789/4612
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Institution/Community
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Nešić, Jovica AU - Cvijetić, Ilija AU - Bogdanov, Jovica AU - Marinković, Aleksandar PY - 2021 UR - https://onlinelibrary.wiley.com/doi/abs/10.1002/prep.202100105 UR - https://cherry.chem.bg.ac.rs/handle/123456789/4612 AB - 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. PB - Wiley T2 - Propellants, Explosives, Pyrotechnics T1 - Synthesis and Characterization of Azido Esters as Green Energetic Plasticizers VL - 46 IS - 10 SP - 1537 EP - 1546 DO - 10.1002/prep.202100105 ER -
@article{ author = "Nešić, Jovica and Cvijetić, Ilija and Bogdanov, Jovica and Marinković, Aleksandar", year = "2021", abstract = "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.", publisher = "Wiley", journal = "Propellants, Explosives, Pyrotechnics", title = "Synthesis and Characterization of Azido Esters as Green Energetic Plasticizers", volume = "46", number = "10", pages = "1537-1546", doi = "10.1002/prep.202100105" }
Nešić, J., Cvijetić, I., Bogdanov, J.,& Marinković, A.. (2021). Synthesis and Characterization of Azido Esters as Green Energetic Plasticizers. in Propellants, Explosives, Pyrotechnics Wiley., 46(10), 1537-1546. https://doi.org/10.1002/prep.202100105
Nešić J, Cvijetić I, Bogdanov J, Marinković A. Synthesis and Characterization of Azido Esters as Green Energetic Plasticizers. in Propellants, Explosives, Pyrotechnics. 2021;46(10):1537-1546. doi:10.1002/prep.202100105 .
Nešić, Jovica, Cvijetić, Ilija, Bogdanov, Jovica, Marinković, Aleksandar, "Synthesis and Characterization of Azido Esters as Green Energetic Plasticizers" in Propellants, Explosives, Pyrotechnics, 46, no. 10 (2021):1537-1546, https://doi.org/10.1002/prep.202100105 . .