explodes at 114 °C
EGDN stands for ethylene glycol dinitrate, other names include 1,2-ethanediol dinitrate, glycol dinitrate, or nitroglycol. EGDN is almost exactly like nitroglycerin, from its chemical properties to its preparation. EGDN will cause severe headaches, as does nitroglycerin, but EGDN headaches are worse, it is also more poisonous, so wear appropriate safety gear. EGDN has better stability in comparison to nitroglycerin, it is also safer to manufacture and handle. The disadvantages of EGDN vs. nitroglycerin is its greater volatility and slower explosive velocity. EGDN was first used in France as a component in non-freezing dynamites. The critical precursor in this synthesis is ethylene glycol, which is the primary ingredient in automobile anti-freeze.
|nitric acid||graduated cylinder|
|sodium carbonate||litmus paper|
|sulfuric acid||separatory funnel|
Prepare a nitrating mixture by mixing 22 mL of concentrated sulfuric acid (>75%) and 15 mL of concentrated nitric acid (>75%) in a 250-mL beaker. Place the beaker into a salt-ice bath and cool it to under 20 °C. While monitoring the temperature with a thermometer, very slowly add 9 mL of ethylene glycol drop by drop with a pipet or buret, keep the temperature below 25 °C at all times. After the glycol addition is complete, allow the mixture to sit for 15 minutes. Next, pour the mixture into a 1000-mL beaker filled with 600 mL of water and stir for several minutes with a stirring rod. Pour the solution into a separatory funnel, allow the EGDN to settle out, it will form a layer on the bottom of the separatory funnel. Drain off the EGDN and keep the acid waste for further extraction. Place the EGDN back into a clean separatory funnel and add plenty of 38° C to 45° C water, mix, then separate. Wash the EGDN again, then wash with a warm 4% solution of sodium carbonate. Wash with warm water three more times. Give it a final wash of concentrated sodium chloride solution, let it sit one day before separating. Separate and check the EGDN for acidity with blue litmus paper. If it is still acidic, keep washing. It must be neutral or it will explode. Dry the neutral EGDN in a desiccator, this may take several days. You will need a graduated cylinder for measuring liquids.
To extract any EGDN that may still be in the waste acid, first neutralize the acid with sodium carbonate solution. Next add an equal volume of chloroform to the neutral waste acid. Mix well then place it into the separatory funnel. Separate out the EGDN and let it stand in the open for one day so the chloroform may evaporate. Add the EGDN to the washing process above.
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