Heat Resistant Explosives. XI. An Unusual Oxidation Reaction Leading to 3,3'-Dihydroxy-2,2', 4,4', 6,6'-Hexanitrobiphenyl (Dipicric Acid, DIPA)
Abstract
The oxidation of 3,3'-dimethyl-2,2',4,4',6,6'hexanitrobiphenyl 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. 52:2054, 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.
Document Details
- Document Type
- Technical Report
- Publication Date
- Feb 26, 1962
- Accession Number
- AD0329453
Entities
People
- Horst G. Adolph
- Joseph C. Dacons
- Mortimer J. Kamlet
Organizations
- Naval Ordnance Laboratory