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AMINO NITROGEN-15 TRACER STUDIES OF THE NITROLYSIS OF HEXAMETHYLENETETRAMINE.
PICATINNY ARSENAL DOVER N J FELTMAN RESEARCH LABS
The path of amino nitrogens in the nitrolysis of hexamethylenetetramine hexamine to a mixture of the homologous cyclic methylenenitramines, 1,3,5,7-tetranitro-1,3,5,7-tetraazacyclo octane HMX and 1,3,5-trinitro-1,3,5-triazacyclohexane RDX, was traced using nitrogen-15. The equilibration of hexamine and ammonium nitrate amino-nitrogens in the formation of the stable intermediate, 1,5-dinitroendomethylene-1,3,5,7tetraazacyclooctane DPT, during the first stage of nitrolysis is attributed to exchange. Only the trimethylene-substituted and not the dimethylene-nitro-substituted amino-nitrogens in DPT undergo interchange with the ammonium ion. DPT does not cleave selectively in the formation of HMX and RDX during the second stage of nitrolysis. In the absence of paraformaldehyde, HMX and RDX are derived essentially from hexamine nitrogens with only a small fraction of approximately 5 of RDX derived from ammonium nitrate. In the presence of paraformaldehyde added initially to the reaction mixture, 7 of the HMX and 40 of the RDX are formed from ammonium nitrate. A mechanism is proposed in which the fragment of the type HOCH2NHNO2 exists as the common precursor to HMX and RDX. Author