Primary Nitramines Related to Nitroglycerine: 1-Nitramino-2,3-dinitroxypropane and 1,2,3-Trinitraminopropane

Abstract

The title compounds 1-nitramino-2,3-dinitroxypropane (NG-N1) and 1,2,3-trinitraminopropane (NG-N3) were formed by multi-step reaction from the corresponding amine. Both compounds were fully characterized by means of multinuclear NMR (1H, 13C, 14N), vibrational spectroscopy, elemental analysis and mass spectrometry. For prediction of the energetic properties ∆Hc values are determined by oxygen bomb calorimetry and validated by quantum theoretical methods. Both compounds are superior in their performance data to nitroglycerine (NG) and pentaerythritol tetranitrate (PETN). In comparison to nitroglycerine the sensitivities towards mechanical stimuli is greatly reduced. X-ray diffraction elucidated the molecular structure of both compounds. NG-N1 crystallizes in the monoclinic space group P21 with a density of 1.799 g/cm3, NG-N3 in the orthorhombic space group Pnma with a density of 1.783 g/cm3. The thermal behavior and long term stabilities were checked using differential scanning calorimetry and thermogravimetric measurements. NG-N1, shows for primary nitramines, exceptional stability in the molten phase making this compound suitable for melt-cast application (Tmp: 65 °C, Tdec: 170 °C).