Oxetane Monomers Based On the Powerful Explosive LLM-116: Improved Performance, Insensitivity, and Thermostability

Born, Max; Karaghiosoff, Konstantin; Klapötke, Thomas M. and Voggenreiter, Michael (2022): Oxetane Monomers Based On the Powerful Explosive LLM-116: Improved Performance, Insensitivity, and Thermostability. In: Chempluschem, Vol. 87, No. 3

Abstract

3-Bromomethyl-3-hydroxymethyloxetane represents an inexpensive and versatile precursor for the synthesis of 3,3-disubstituted oxetane derivatives. In the present work, its synthesis was improved and energetic oxetanes based on the explosive LLM-116 (4-amino-3,5-dinitro-1H-pyrazole) prepared. Reaching detonation velocities and pressures of up to 7335 ms(-1) and 20.9 GPa in combination with a high thermostability and insensitivity, these surpass the prior art by far. Next to a symmetric LLM-116 derivative, three asymmetric compounds were prepared using azido-, nitrato- and tetrazolyl-moieties. All compounds were intensively characterized by vibrational-, mass- and multinuclear (H-1, C-13, N-14) NMR spectroscopy, differential scanning calorimetry and elemental analysis. The molecular structures were elucidated by single crystal X-ray diffraction. Hirshfeld analysis allowed to estimate their sensitivity next to a practical evaluation using BAM standard procedures. Their performance was calculated using the EXPLO5 V6.04 code and a small-scale shock reactivity test and initiation test demonstrated their insensitivity and performance.

• Item Type: Journal article
• Faculties: Chemistry and Pharmacy > Department of Chemistry
• Subjects: 500 Science > 540 Chemistry
• ISSN: 2192-6506
• Language: English
• DFG: Gefördert durch die Deutsche Forschungsgemeinschaft (DFG) - 491502892