The Energetic Nitrocarbamate O2NN(H)CO[OCH2C(NO2)3] Derived from Phosgene

Authors

  • Quirin J. Axthammer,

    1. Energetic Materials Research, Department of Chemistry, Ludwig Maximilian University Munich, Butenandtstr. 5–13 (D), 81377 Munich, Germany
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  • Thomas M. Klapötke,

    Corresponding author
    1. Energetic Materials Research, Department of Chemistry, Ludwig Maximilian University Munich, Butenandtstr. 5–13 (D), 81377 Munich, Germany
    • Energetic Materials Research, Department of Chemistry, Ludwig Maximilian University Munich, Butenandtstr. 5–13 (D), 81377 Munich, Germany, Fax: +49-89-2180-77492

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  • Burkhard Krumm,

    1. Energetic Materials Research, Department of Chemistry, Ludwig Maximilian University Munich, Butenandtstr. 5–13 (D), 81377 Munich, Germany
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  • Richard Moll,

    1. Energetic Materials Research, Department of Chemistry, Ludwig Maximilian University Munich, Butenandtstr. 5–13 (D), 81377 Munich, Germany
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  • Sebastian F. Rest

    1. Energetic Materials Research, Department of Chemistry, Ludwig Maximilian University Munich, Butenandtstr. 5–13 (D), 81377 Munich, Germany
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Abstract

A new simple synthesis route for 2,2,2-trinitroethyl chloroformate (1), from easily available starting materials 2,2,2-trinitroethanol and phosgene is presented. 2,2,2-Trinitroethyl carbamate (2) was obtained by the reaction of 1 with aqueous ammonia. The nitration of 2 with anhydrous nitric acid and sulfuric acid yields 2,2,2-trinitroethyl nitrocarbamate (3), which has potential as a perchlorate free high energetic dense oxidizer with a high oxygen balance of Ω(CO2) = +14.9 %. The thermal stability was studied using differential scanning calorimetry and the energies of formation were calculated on the CBS-4M level of theory, as well as several detonation parameters and propulsion properties were determined. In addition to full spectroscopic characterization, X-ray diffraction studies were performed for 2 and 3.

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