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Axthammer, Quirin J.; Klapötke, Thomas M.; Krumm, Burkhard (2016): Studies on the synthesis and properties of 1,1,1-trinitroprop-2-yl urea, carbamate and nitrocarbamate. In: Zeitschrift für Naturforschung Section B - A Journal of Chemical Sciences, Vol. 71, Nr. 7: S. 811-820
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Potential high energetic dense oxidizers with the 1,1,1-trinitropropan-2-yl moiety are described in this study. The urea, N,N'-bis(1,1,1-trinitropropan-2-yl)urea (1), is synthesized by the reaction of urea with acetaldehyde and trinitromethane. The reaction of 1,1,1-trinitropropan-2-ol (2) with the reagent chlorosulfonyl isocyanate results in the formation of 1,1,1-trinitroprop-2-yl carbamate (3). The nitration of 3 with anhydrous nitric and sulfuric acid yields the nitrocarbamate (4). All compounds were fully characterized by multinuclear NMR (H-1, C-13, N-14/15) and vibrational spectroscopy, mass spectrometry and elemental analysis (C,H,N). For analysis of the thermostability differential scanning calorimetry (DSC) was used. Energetic properties, the sensitivities towards impact, friction and electrostatic discharge were tested and compared with the corresponding 2,2,2-trinitroethyl and 3,3,3-trinitropropyl derivatives. The crystal structures of two compounds with that of the 1,1,1-trinitroprop-2-yl moiety have been determined by low temperature X-ray diffraction and discussed. The energies of formation were evaluated and several detonation parameters such as the velocity of detonation and the propulsion performance were calculated with the program package EXPLO5.