SYNTHESIS OF C-14-LABELED HEXAHYDRO-1,3,5-TRINITRO-1,3,5-TRIAZINE (RDX), 2,4,6-TRINITROTOLUENE (TNT), NITROCELLULOSE (NC) AND GLYCIDYLAZIDE POLYMER (GAP) FOR USE IN ASSESSING THE BIODEGRADATION POTENTIAL OF THESE ENERGETIC COMPOUNDS

Within the framework of an R & D project on bioremediation of soils contaminated with energetic compounds, the biodegradation of energetic products such as hexogen (RDX), trinitrotoluene (TNT), nitrocellulose (NC) and glycidyl azide polymer (GAP) is under study. Microcosm assays must be performed with radioactive carbon-14 labelled products in order to follow the biodegradation process. C-14-RDX was prepared by nitration of hexamethylenetetramine (HMTA) according to the Hale process. C-14-ring and methyl labelled TNTs were synthesized according to the Dorey and Carper procedure. C-14-cellulose was synthesized from C-14-glucose by Acetobacter xylinum. Nitration of the C-14-cellulose yielded C-14-nitrocellulose. C-14-glycidyl azide polymer was obtained by polymerization and azidation of C-14-epichlorohydrin (ECH) which was synthesized from C-14-glycerol. Hydrochlorination of C-14-glycerol and epoxidation of the resulting C-14-1,3-dichloro 2-propanol yielded C-14-ECH. The syntheses of these C-14-labelled explosives are described in this paper.