Highly Energetic, Low Sensitivity Aromatic Peroxy Acids

The synthesis, structure, and energetic materials properties of a series of aromatic peroxy acid compounds are described. Benzene‐1,3,5‐tris(carboperoxoic) acid is a highly sensitive primary energetic material, with impact and friction sensitivities similar to those of triacetone triperoxide. By con...

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Bibliographic Details
Published in:Chemistry : a European journal 2016-02, Vol.22 (8), p.2582-2585
Main Authors: Gamage, Nipuni-Dhanesha H., Stiasny, Benedikt, Stierstorfer, Jörg, Martin, Philip D., Klapötke, Thomas M., Winter, Charles H.
Format: Article
Language:English
Subjects:
Acids
Aromatic compounds
Benzene
Bonding
Chemistry
Contact
Detonation
Energetic materials
Explosive bonding
explosives
Friction
Hydrocarbons
Hydrogen bonding
Hydrogen bonds
Organic peroxides
Peracids
peroxides
sensitivities
Sensitivity
structure elucidation
Trinitrotoluene
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Summary:The synthesis, structure, and energetic materials properties of a series of aromatic peroxy acid compounds are described. Benzene‐1,3,5‐tris(carboperoxoic) acid is a highly sensitive primary energetic material, with impact and friction sensitivities similar to those of triacetone triperoxide. By contrast, benzene‐1,4‐bis(carboperoxoic) acid, 4‐nitrobenzoperoxoic acid, and 3,5‐dinitrobenzoperoxoic acid are much less sensitive, with impact and friction sensitivities close to those of the secondary energetic material 2,4,6‐trinitrotoluene. Additionally, the calculated detonation velocities of 3,5‐dinitrobenzoperoxoic acid and 2,4,6‐trinitrobenzoperoxoic acid exceed that of 2,4,6‐trinitrotoluene. The solid‐state structure of 3,5‐dinitrobenzoperoxoic acid contains intermolecular O‐H⋅⋅⋅O hydrogen bonds and numerous N⋅⋅⋅O, C⋅⋅⋅O, and O⋅⋅⋅O close contacts. These attractive lattice interactions may account for the less sensitive nature of 3,5‐dinitrobenzoperoxoic acid. The first low sensitivity organic peroxides: Compounds containing oxygen–oxygen bonds are notorious for being explosive and highly sensitive. A series of aromatic peroxy acids, however, demonstrates that low‐sensitivity compounds can be obtained by careful control of the substituents. Solid‐state structures suggest that O‐H⋅⋅⋅O hydrogen bonding and O⋅⋅⋅O close contacts stabilize the labile O−O bonds.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201502989