Heat Resistant Explosives, XVII. Improved Procedures for the Preparation of 3,3'-diamino-2,2',4,4',6,6'heranitrohiphenyl, Dipam.
Abstract
Improvements in the synthesis of 3,3'-diamino2,2', 4,4', 6,6'-hexanitrobiphenyl, DIPAM, from 3-bromoanisole, I, via 3-bromo-2,4,6-trinitroanisole, II, and 3,3'-dimethoxy-2,2', 4,4', 6,6'hexanitrobiphenyl, III, were effected by modifications in the Ullman and amination reactions. The Ullmann reaction was carried out in refluxing toluene for relatively short periods of time. DIPAM was also prepared from 3-chloroanisole, IV, via 3-chloro-2,4,6-trinitroanisole, V, and III with nearly equal facility. In this series, the Ullmann reaction was run in refluxing xylene. The dianisole, III, was converted to DIPAM by several procedures; most conveniently, by purification in situ followed by amination in mixed solvents. Yields of crude DIPAM as high as 81%, based on II and IV were realized. Most of these products melted above 300 C (dec), some as high as 306 C (dec). The improvements in the synthesis facilitate large scale production and will reduce the cost of DIPAM manufacture. (Author)
Document Details
- Document Type
- Technical Report
- Publication Date
- May 18, 1964
- Accession Number
- AD0352151
Entities
People
- J. C. Dacons
- R. E. Oesterling
Organizations
- Naval Ordnance Laboratory