Synthesis of 14C-labelled hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX), 2,4,6-trinitrotoluene (TNT), nitrocellulose (NC) and glycidyl azide polymer (GAP) for use in assessing the biodegradation potential of these energetic compounds

Article abstract of DOI:10.1002/jlcr.2580360608

Within the framework of an R and 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. ¹⁴C-RDX was prepared by nitration of hexamethylenetetramine (HMTA) according to the Hale process. ¹⁴C-ring and methyl labelled TNTs were synthesized according to the Dorey and Carper procedure. ¹⁴C-cellulose was synthesized from ¹⁴C-glucose by Acetobacter xylinum. Nitration of the ¹⁴C-cellulose yielded ¹⁴C-nitrocellulose. ¹⁴C-glycidyl azide polymer was obtained by polymerization and azidation of ¹⁴C-epichlorohydrin (ECH) which was synthesized from ¹⁴C-glycerol. Hydrochlorination of ¹⁴C-glycerol and epoxidation of the resulting ¹⁴C-1,3-dichloro 2-propanol yielded ¹⁴C-ECH. The syntheses of these ¹⁴C-labelled explosives are described in this paper.