Fluorodinitroethyl Ortho-carbonate and -formate as Potential High Energy Dense Oxidizers

Tetrakis(2-fluoro-2,2-dinitroethyl) ortho-carbonate (1) and tris(2-fluoro-2,2-dinitroethyl) ortho-formate (2) were synthesized by the reaction of carbon tetrachloride, respectively chloroform, with 2-fluoro-2,2-dinitroethanol and catalytic amounts of anhydrous iron(III) chloride. The compounds were characterized by single-crystal X-ray diffraction, vibrational spectroscopy (IR and Raman), multinuclear NMR spectroscopy, elemental analysis, and multi-temperature DSC measurements. The suitability of the compounds as potential oxidizers in energetic formulations has been investigated and discussed. The heats of formation of the products were determined experimentally using bomb calorimetric methods. With this value and the experimental (X-ray) density, several detonation parameters such as the detonation pressure, velocity, energy, and temperature were computed using the Explo5 code. The sensitivity towards impact, friction and electrostatic discharge was tested using the BAM drop hammer, a friction tester and a small-scale electrostatic discharge device.