Ethyl nitrate is found in the atmosphere, where it can react with other gases to form smog. The pollutant was originally thought to have been formed mainly by the combustion of fossil fuels. However recent analysis of ocean water samples reveal that in places where cool water rises from the deep, the water is saturated with alkyl nitrates, likely formed by natural processes.[2]
History and synthesis
Reaction of ethanol with nitric acid was investigated since the Middle Ages, but the fact that it produces mostly ethyl nitrite was not discovered until the 19th century. Eugène Millon was the first to synthesize ethyl nitrate in 1843 by adding urea to the mixture in order to remove any nitrous acid.[3][4]
Ethyl nitrate can be prepared by nitroxylating ethanol with fuming nitric acid or a mixture of concentrated sulfuric and nitric acids. Besides decomposing nitrous acid, the aforementioned necessary addition of urea prevents explosion.[5] Further purifying by distillation carries a risk of explosion.[6]
Ethyl nitrate has also been prepared by bubbling gaseous nitryl fluoride through ethanol at −10 °C.[7] The reaction was subsequently studied in detail.[8][9]
A nucleophilic substitution reaction of ethyl halides and silver nitrate can also yield ethyl nitrate. Again, purification poses explosion risks.
Ethyl nitrate is a sensitive explosive that is prone to detonating upon impact or high temperatures, though is less so than methyl nitrate. It has a detonation velocity of 6,010 m/s,[11] and is therefore a high explosive.
References
^Schofield, Kenneth (1980). Aromatic nitration. Cambridge: Cambridge University Press. p. 94. ISBN9780521233620. OCLC6357479.
