Synthesis, Characterization, and Rheological Evaluation of 1,3-Diazido-2-ethyl-2-nitropropane as an Energetic Plasticizer

Abstract

An energetic plasticizer, 1,3-diazido-2-ethyl-2-nitropropane (DAENP), was synthesized and characterized in good yield and high purity. DAENP is synthesized in three steps: 1) 1-nitropropane is condensed with formaldehyde to yield 2-ethyl-2-nitro-1,3-propane diol; 2) 2-ethyl-2-nitro-1,3-propane diol on tosylation gave 2-ethyl-2-nitro-1,3-bis(p-toluene sulfonyl) propyl ester; 3) azidation of the tosylated compound gives DAENP. The product was characterized by elemental analysis, Fourier transform infrared (FTIR) spectroscopy and 1H-NMR and purity was tested by high-performance liquid chromatography (HPLC). Thermal studies revealed that DAENP is thermally stable up to 196°C, has high energy output of the order 2,056 J/g, and a very low glass transition temperature (−96.76°C). DAENP is compatible with energetic binders like glycidyl azide polymer (GAP), 3,3-bis (azido methyl)oxetane–tetra hydroxyl furan (BAMO-THF) copolymer, and poly-3-nitrato methyl-3-methyl oxtetane (poly NIMMO or PLN). Rheological and thermal data showed that it can be used successfully with these binders.