Nitration of anhydrous Ethanediol is done with Adding 65% Nitric acid with excess 98% sulfuric acid around 100 degrees C (adding one chemical drop by drop on mix of other two, allowing copious fumes of NO2 go out and) and then boiled above 180 C (to remove all yellow-brown color of the liquid to colorless).

The dehydration of ethanediol is likely to produce ethene-1-ol that may be further dehydrated to ethyne (acetylene, and escape from solution) or tautomerized to ethanal (acetaldehyde). Nitrating can produce either 2-nitroethanol or 1.2-dinitroethane, or the nitric acid itself can oxidize acetaldehyde to acetic acid. Or can nitroethene form?

However, I cooled the solution to 4 C and reheated to around 30 C, but fine needle shaped crystals precipitated that didn't dissolve. Is this glacial acetic acid? I cannot separate them due to lack of distillation apparatus or Barium Nitrate.

BTW: I took the supernatent liquid at room temperature, dissolved it 2000 times and drank it a little. It tastes awfully sour, but doesn't taste like vinegar. When I was boiling the solution, upon ceasing of chocking sharp metallic-smelling brown fume evolution, a strong vinegary smell appeared.

As I kept the solution bottled shut for a day or two , some tiny gas bubbles started to appear. What are these bubbles? Acetic anhydride, Acetylene, or something else? they are very low voluminous, so cannot be put to test for gases as per wet-chemical method. And I do not have Gas Chromatography at my hand.

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