Synthesis of Erythritol Tetranitrate Derivatives: Functional Group Tuning of Explosive Sensitivity

Understanding the factors that affect explosive sensitivity is paramount to the safe handling and development of new explosives molecules. Erythritol tetranitrate (ETN) is an explosive that recently has attracted significant attention in the explosives community because of its ease of synthesis and...

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Bibliographic Details
Published in:Journal of organic chemistry 2020-04, Vol.85 (7), p.4619-4626
Main Authors: Lease, Nicholas, Kay, Lisa M, Brown, Geoffrey W, Chavez, David E, Robbins, David, Byrd, Edward F. C, Imler, Gregory H, Parrish, Damon A, Manner, Virginia W
Format: Article
Language:English
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Summary:Understanding the factors that affect explosive sensitivity is paramount to the safe handling and development of new explosives molecules. Erythritol tetranitrate (ETN) is an explosive that recently has attracted significant attention in the explosives community because of its ease of synthesis and physical properties. Herein, we report the synthesis of ETN derivatives using azide, nitramine, and nitrate ester functional groups. Impact, spark, and friction sensitivity measurements, computationally calculated explosive properties, and the crystal structure analysis of the ETN derivatives are reported. Mixing explosive functional groups led to changes in the explosive sensitivity, explosive performance as well as physical properties including melting point and physical state at room temperature. Overall, we have demonstrated that combining functional groups can enable the tuning of explosive and physical properties of a molecule. This tunability can potentially aid in the development of new explosives in which characteristics are varied to meet certain specifications.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b03344