4.7 Article

3,3-Dinitratooxetane - an important leap towards energetic oxygen-rich monomers and polymers

Journal

CHEMICAL COMMUNICATIONS
Volume 57, Issue 22, Pages 2804-2807

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d1cc00466b

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Funding

  1. Ludwig-Maximilian University of Munich (LMU)
  2. Office of Naval Research (ONR) [ONR N00014-19-1-2078]
  3. Strategic Environmental Research and Development Program (SERDP) [WP19-1287, W912HQ19C0033]

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A new solid-state oxidizer, 3,3-dinitratooxetane, with 62.2% oxygen content was synthesized and characterized by X-ray diffraction. The study also involved the preparation of 3-nitratooxetane and the first-time synthesis of 3-nitrato-3-methyloxetane, along with theoretical calculations and sensitivity tests towards impact and friction.
3-Substituted oxetanes are valuable monomers for modern ring-opening polymerizations. A new solid-state oxidizer, 3,3-dinitratooxetane (C3H4N2O7), which has an oxygen content of 62.2% was synthesized by the addition of N2O5 to oxetan-3-one. Monoclinic single crystals suitable for X-ray diffraction (rho 1.80 g cm(-3)) were obtained by recrystallization from dichloromethane. In addition, 3-nitratooxetane was prepared by an improved method and 3-nitrato-3-methyloxetane was synthesized for the first time. Theoretical calculations were computed by the EXPLO5 software and additionally sensitivities towards impact and friction were determined.

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