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CHNO Based Molecules Containing 2,2,2‐Trinitroethoxy Moieties as Possible High Energy Dense Oxidizers
Author(s) -
Klapötke Thomas M.,
Krumm Burkhard,
Moll Richard,
Rest Sebastian F.
Publication year - 2011
Publication title -
zeitschrift für anorganische und allgemeine chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.354
H-Index - 66
eISSN - 1521-3749
pISSN - 0044-2313
DOI - 10.1002/zaac.201100340
Subject(s) - detonation , detonation velocity , elemental analysis , anhydrous , chemistry , chloroform , raman spectroscopy , infrared spectroscopy , analytical chemistry (journal) , titanium tetrachloride , single crystal , molecule , standard enthalpy of formation , inorganic chemistry , catalysis , explosive material , organic chemistry , crystallography , physics , optics
Tetrakis(2,2,2‐trinitroethyl) orthocarbonate ( 1 ) and 2,2,2‐trinitroethyl formate ( 2 ) were synthesized by the reaction of carbon tetrachloride, respectively chloroform, with the corresponding equivalents of 2,2,2‐trinitroethanol and catalytic amounts of anhydrous iron(III)chloride. 2,2,2‐Trinitroethyl formal ( 3 ) was prepared by the condensation of paraformaldehyde with 2,2,2‐trinitroethanol. The compounds were fully characterized by single‐crystal X‐ray diffraction, vibrational spectroscopy (IR and Raman), multinuclear NMR spectroscopy, elemental analysis, and multi‐temperature DSC measurements. Due to the positive oxygen balance, the suitability of all three compounds mentioned as potential oxidizers in energetic formulations was investigated and discussed. In addition, the heats of formation of the products were determined experimentally using bomb calorimetric methods. With this value and the experimental (X‐ray) density, several detonation parameters such as the detonation pressure, velocity, energy, and temperature were computed using the EXPLO5 code. Furthermore, the sensitivity towards impact, friction and electrical discharge was tested using the BAM drop hammer, a friction tester as well as a small‐scale electrical discharge device.