Synthesis of Energetic Materials at High Pressures.
Abstract
Fluorodinitroacetonitrile (FDAN) has been trimerized to the 1, 3, 5-triazine structure at 10 kbar pressure with the use of acidic alcohol catalysts. The pseudohalogen character of the CF(NO2)2 group, however, makes it subject to displacement from the triazine ring by the alcohol catalyst. As a result of the major triazine products bear alkoxy substituents. In the case of CF3CH2OH as catalyst the chief triazine product is (CF3CH2O)2(CN)3CF(NO2)2. Reaction of preformed imidic ester with the nitrile can diminish this side reaction to the point where CF3CH2O(CN)3(CF(NO2)2)2 is the chief triazine product. There is evidence that the FDAN cyclotrimer is formed in low yield with CF3CH2OH as catalyst but the compound has not been isolated. The use of the more acidic PhOH as catalyst gives PhO(CN)3 (CF(NO2)2)2 as the chief product but the tris (fluorodinitromethyl) triazine still remains as a minor product, if present at all. Two mechanisms of cyclotrimerization appear operative, depending on the structure of the imidic ester intermediate.
Document Details
- Document Type
- Technical Report
- Publication Date
- Dec 21, 1978
- Accession Number
- ADA068484
Entities
People
- Horst G. Adolph
- William M. Koppes
Organizations
- Naval Ordnance Laboratory