Polynitro Containing Energetic Materials based on Carbonyldiisocyanate and 2, 2-Dinitropropane-1, 3-diol

Authors

  • Thomas M. Klapötke,

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

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  • Burkhard Krumm,

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

    1. Department of Chemistry, Ludwig Maximilian University of Munich, Butenandtstraße 5–13 (D), 81377 Munich, Germany
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  • Muhamed Sućeska

    1. Department of Chemistry, Ludwig Maximilian University of Munich, Butenandtstraße 5–13 (D), 81377 Munich, Germany
    2. Brodarski Institut d.o.o.AvenijaVeaeslava Holjevca 20, 10000 Zagreb, Croatia
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  • Dedicated to Professor Ingo-Peter Lorenz on the Occasion of His 70th Birthday

  • Supporting Information for this article is available on the WWW under http://dx.doi.org/10.1002/zaac.201300563 or from the author.

Abstract

New polynitro compounds containing a carbonyl biscarbamate moiety derived from the precursor carbonyldiisocyanate were synthesized. In addition, 2, 2-dinitropropane-1, 3-diyl bis(2, 2,2-trinitroethylcarbamate) and 2, 2-dinitropropane-1, 3-diyl bis(2, 2,2-trinitroethyl) dicarbonate, were synthesized using 2, 2-dinitropropane-1, 3-diol as starting material. The compounds were characterized by using the analytical methods, single-crystal X-ray diffraction, vibrational spectroscopy (IR and Raman), multinuclear NMR spectroscopy, elemental analysis, and mass spectrometry. The thermal behavior was investigated with DSC measurements. The suitability of the compounds as potential oxidizers in energetic formulations was determined. The heats of formation of the compounds were calculated with GAUSSIAN 09. The detonation parameters such as the detonation pressure, velocity, energy, and temperature were computed using the EXPLO5 code. For a secure handling of the materials, the sensitivity towards impact, friction, and electrical discharge was tested using the BAM drop hammer, BAM friction tester as well as a small-scale electrical discharge device, respectively.

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