Synthesis, characterization, thermal and computational studies of novel 
tetra-azido esters as energetic plasticizers

Kumari, Dimple; Singh, Haridwar; Patil, Mahendra; Thiel, Walter; Pant, Chandra Shekahr; Banerjee, Shaibal

doi:10.1016/j.tca.2013.03.042

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Synthesis, characterization, thermal and computational studies of novel tetra-azido esters as energetic plasticizers

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Thiel, Walter
Research Department Thiel, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Kumari, D., Singh, H., Patil, M., Thiel, W., Pant, C. S., & Banerjee, S. (2013). Synthesis, characterization, thermal and computational studies of novel tetra-azido esters as energetic plasticizers. Thermochimica Acta, 562, 96-104. doi:10.1016/j.tca.2013.03.042.

Cite as: https://hdl.handle.net/11858/00-001M-0000-0014-A351-A

Abstract

This paper describes the synthesis and characterization of two novel tetra-azido energetic plasticizers from readily available commercial sources possessing good thermal stability. Two new energetic azido esters named bis(1,3-diazido prop-2-yl)malonate (1) and bis(1,3-diazido prop-2-yl)glutarate (2) have been synthesized and characterized by IR, ¹H NMR, ¹³C NMR, HRMS, thermal analysis, and compatibility tests. Both azido esters (1 and 2) show good thermal stability with decomposition temperatures of 233.5 °C and 232.6 °C. Their densities are measured to be 1.25 g/cm³ and 1.27 g/cm³, respectively. Glass transition temperature (T_g) of both compounds 1 and 2 is −69°C and −68 °C and after addition with binder shows reduction in T_g of polymer-plasticizer blends as compared to T_g of polymer only with single decomposition temperature values which indicate the presence of single phase homogeneous system. Thermal decomposition kinetics of both compounds was determined by DSC, using non-isothermal Kissinger and Friedman differential isoconversional method. Density functional theory calculations on compounds 1 and 2 predict positive heats of formations.