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Dinitrophenyl Triazoles – “A Class of Energetic Azoles”: Synthesis, Characterisation, and Performance Evaluation Studies
Author(s) -
Nimesh Sasidharan,
Rajendran Arolickal G.
Publication year - 2012
Publication title -
propellants, explosives, pyrotechnics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.56
H-Index - 65
eISSN - 1521-4087
pISSN - 0721-3115
DOI - 10.1002/prep.201000146
Subject(s) - exothermic reaction , chemistry , thermal decomposition , standard enthalpy of formation , energetic material , molecule , decomposition , heat capacity , 1,2,4 triazole , combustion , triazole , nitro , calorimetry , elemental analysis , thermal stability , organic chemistry , thermodynamics , explosive material , physics , alkyl
Energetic azoles have shown great potential as powerful energetic molecules, which find various applications in both military and civilian fields. This work describes the synthesis, characterization and performance evaluation of two energetic triazole derivatives, viz. N‐(2,4‐dinitrophenyl)‐3‐nitro‐1H‐1,2,4‐triazole ( 1a ) and N‐(2,4‐dinitrophenyl)‐3‐azido‐1H‐1,2,4‐triazole ( 1b ). The compounds were synthesized from 3‐nitro‐1,2,4‐triazole and 3‐azido‐1,2,4‐triazole, by a simple synthetic route and structurally characterized using FT‐IR and NMR ( 1 H, 13 C) spectroscopy as well as elemental analysis. Thermal analyses on the molecules were performed using simultaneous TG‐DTA. Both compounds ( 1a , 1b ) showed good thermal stability with exothermic decomposition peaks at 348 °C and 217 °C, respectively, on DTA. The energetic and sensitivity properties of both compounds like friction sensitivities and heats of formation are reported. The heats of combustion at constant volume were determined using oxygen bomb calorimetry and the results were used to calculate the standard molar heats of formation (Δ f H m ). The azido derivative ( 1b ) showed a higher positive heat of formation. The thermo‐chemical properties of the compounds as well as the thermal decomposition products were predicted using the REAL thermodynamic code.