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Concept
Nitration
Summary
In organic chemistry, nitration is a general class of chemical processes for the introduction of a nitro group () into an organic compound. The term also is applied incorrectly to the different process of forming nitrate esters () between alcohols and nitric acid (as occurs in the synthesis of nitroglycerin). The difference between the resulting molecular structures of nitro compounds and nitrates () is that the nitrogen atom in nitro compounds is directly bonded to a non-oxygen atom (typically carbon or another nitrogen atom), whereas in nitrate esters (also called organic nitrates), the nitrogen is bonded to an oxygen atom that in turn usually is bonded to a carbon atom (nitrito group).
There are many major industrial applications of nitration in the strict sense; the most important by volume are for the production of nitroaromatic compounds such as nitrobenzene.
Nitration reactions are notably used for the production of explosives, for example the conversion of guanidine to nitroguanidine and the conversion of toluene to trinitrotoluene (TNT). However, they are of wide importance as chemical intermediates and precursors. Millions of tons of nitroaromatics are produced annually.
Typical nitration syntheses apply so-called "mixed acid", a mixture of concentrated nitric acid and sulfuric acids. This mixture produces the nitronium ion (NO2+), which is the active species in aromatic nitration. This active ingredient, which can be isolated in the case of nitronium tetrafluoroborate, also effects nitration without the need for the mixed acid. In mixed-acid syntheses sulfuric acid is not consumed and hence acts as a catalyst as well as an absorbent for water. In the case of nitration of benzene, the reaction is conducted at a warm temperature, not exceeding 50 °C. The process is one example of electrophilic aromatic substitution, which involves the attack by the electron-rich benzene ring:
Alternative mechanisms have also been proposed, including one involving single electron transfer (SET).
Official source
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