Synthesis of Energetic Materials at High Pressures.
Abstract
The utility of a high-pressure technique to effect the trimerization of fluorodinitroacetonitrite to the corresponding triazine has been investigated. Whereas fluorodinitroacetonitrile has resisted previous ambient pressure attempts at trimerization with a variety of catalysts, it was found to form triazines quite readily when subjected to 1 GPa pressures in the presence of certain primary alcohols and phenols. However, the triazines formed contained a mixture of fluorodinitromethyl and alkoxy or aryloxy substituents, apparently as a consequence of competition between CF(NO2)2 and ROH for elimination in the cyclization steps, or of nucleophilic displacement of CF(NO2)2 by ROH in the initial triazine product. A study was made of the effect of ROH acidity on product composition with the finding that mixed triazines formed in all cases in which reaction occurred. An alternative mechanisms for triazine formation from nitriles was postulated to account for some novel observations made during this work. Our results indicate that tris (fluorodinitromethyl) triazine must be highly susceptible to nucleophilic attack with displacement of at least one CF(NO2)2 group, and would thus be subject to easy hydrolysis.
Document Details
- Document Type
- Technical Report
- Publication Date
- Mar 01, 1980
- Accession Number
- ADA084800
Entities
People
- Horst G. Adolph
- William M. Koppes
Organizations
- Naval Ordnance Laboratory