Heat Resistant Explosives. XI. An Unusual Oxidation Reaction Leading to 3,3'-Dihydroxy-2,2', 4,4', 6,6'-Hexanitrobiphenyl (Dipicric Acid, DIPA)
NAVAL ORDNANCE LAB WHITE OAK MD
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The oxidation of 3,3-dimethyl-2,2,4,4,6,6hexanitrobiphenyl with a dichromate-oleum-nitric acid mixture yielded dipicric acid rather than 3,3- dicarboxy-2,2,4,4,6,6-hexanitrobiphenyl as reported by Adams and coworkers J. Am Chem. Soc. 522054, 1930. The replacement of a methyl group by hydroxyl under these oxidizing conditions appears to be general for trinitrotoluene derivatives but not for dinitrotoluenes or other alkyl trinitrobenzenes. The potentialities of DIPA as a high temperature explosive are discussed.
- Organic Chemistry
- Ammunition and Explosives