Synthesis of trimethoxytrinitrobenzene
Trimethoxytrinitrobenzene is an energetic intermediate used to prepare the explosives TATB, ADAP, and a few additional energetic materials.
- benzene, 1,3,5-trimethoxy-2,4,6-trinitro- (8CI,9CI)
- 1,3,5-trimethoxy-2,4,6-trinitrobenzene
Synthesis 1:
Prepare a solution of 5.0 g of trinitrophloroglucinol and 12.5 g of potassium carbonate in 100 mL of dimethyl sulfate. Heat this solution at 125 C for 4 hours. Pour the solution into a beaker containing 100 mL of cold water, add a slight excess of 30% sodium hydroxide to make the solution basic, and heat the solution to almost boiling. Allow the solution to cool to room temperature. Filter to collect the solid and extract it with 150 mL of acetone in several portions. Heat the combined extract on a steam bath to concentrate itthe product should precipitate. Filter to collect the crystals of trimethoxytrinitrobenzene, and allow them to dry. Yield is about 2 g or 34%.
Synthesis 2:
Prepare a solution of 5.22 g of trinitrophloroglucinol in 30 mL of trimethyl orthoformate. Distill this solution at 95-100 C for 4 hours. An azeotropic mixture of methanol and methyl formate will distill off at 65-78 C. The reaction mixture is then heated at 105-110 C for 30 minutes to obtain yet more distillate at 92-98 C. Allow the solution to cool somewhat and concentrate the remaining orange solution at a lower temperature to precipitate the product. The final yield of trimethoxytrinitrobenzene is about 6 g or 99%.
By using other alkylated versions of methyl formate, for example ethyl formate, or propyl formate, you can prepare triethoxytrinitrobenzene and tripropoxytrinitrobenzene respectively.
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