Tetranitromethane, also called TeNMe, is a colorless to pale yellow liquid that was first prepared by the action of nitric acid on trinitromethane back in 1861. The Germans used it back in WWII for an intermediate in making other explosives and as a substitute for nitric acid in the V-2 rocket. A pilot plant in New Jersey used to make tetranitromethane blew up in 1953. This compound is rather toxic, irritating the skin, mucous membranes and the respiratory tract. Prolonged exposure to vapors causes damage to the liver, kidneys, and other organs. A concentration of 0.1 ppm in the air is fatal. Mixtures of tetranitromethane with organic liquids tend to form more powerful explosives, but the sensitivity is worse. A list of mixtures has been provided. Tetranitromethane has been proposed as a chemical warfare agent.
|acetic anhydride||addition funnel|
|sodium hydroxide||Clasien adapter|
|water||250-ml Florence flask|
This reaction will produce toxic fumes, so take the necessary precautions. Measure out 21 mL of 100% nitric acid into a round-bottomed 250-ml Florence flask. It is important to only use anhydrous acid and no more than the amount proscribed, any deviation will drastically lower the yield of this reaction. Place a Clasien adapter on the flask and attach a thermometer on the straight arm, almost touching the bottom of the flask, and an addition funnel on the side arm. In this instance do not use a thermometer adapter to connect the thermometer, there must be a gap to allow reaction gasses to escape.
Cool the contents of the flask to 10 °C in an ice water bath. Slowly add 47.2 mL of acetic anhydride in portions of 0.5 mL at a time from the buret. Do not let the temperature of the mixture rise above 10 °C during the addition, failure to maintain the temp may result in a dangerous runaway reaction. After the first 5 mL of acid has been added the reaction should have calmed down enough where you can begin to add larger portions of 1 to 5 mL at a time with constant shaking.
After all the acetic anhydride has been added, everything is removed from the flask. The neck of the flask is wiped clean with a towel, the flask is then covered with an inverted beaker, and it is now allowed to come up to room temperature in the ice bath. It is important to keep the flask in the ice bath because the reaction can still become dangerous if it is allowed to warm up too rapidly. The flask should be left alone for 1 week (yes, 7 days) at room temperature.
After sitting for a week the contents are mixed with 300 mL of water in a 500-mL Florence flask. The tetranitromethane is removed by steam distillation, the tetranitromethane passes over with the first 20 mL of the distillate. The lower layer of the distillate is separated, washed with dilute sodium hydroxide, and then water, and finally dried over anhydrous sodium sulfate in a desiccator. Yield is 14–16 g, or about 57-65%. Do not distill tetranitromethane by ordinary distillation means, it may explode. The residues of distillation are especially dangerous. Use only steam distillation, and even then be careful. You will need a graduated cylinder for measuring liquids.
Explosive mixtures with organic compounds
Tetranitromethane can be mixed with several compounds including benzene, ethylene glycol, gasoline, naphthalene, and toluene, but the resulting explosive may be rather sensitive to detonation. Here are some mixing ratios:
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