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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). Nitrations are, however, of wide importance virtually all aromatic amines are produced from nitro precursors. Millions of tons of nitroaromatics are produced ...
Nitration of toluene gives mono-, di-, and trinitrotoluene, all of which are widely used. Dinitrotoluene is the precursor to toluene diisocyanate, a precursor to polyurethane foam. Trinitrotoluene (TNT) is an explosive. Complete hydrogenation of toluene gives methylcyclohexane. The reaction requires a high pressure of hydrogen and a catalyst.
The most common one is 2,4-dinitrotoluene. The nitration of toluene gives sequentially mononitrotoluene, DNT, and finally TNT. 2,4-DNT is the principal product from dinitration, the other main product being about 30% 1,3-DN2-T. The nitration of 4-nitrotoluene gives 2,4-DNT. [5]
Together with other isomers, 4-nitrotoluene is prepared by nitration of toluene, [4] commonly using titanium(IV) nitrate. [5] It undergoes the reactions typical for nitrobenzene derivatives, e.g. hydrogenation gives p-toluidine. Oxidation of the methyl substituent of 4-nitrotoluene has been extensively investigated.
Control of nitrogen oxides in feed nitric acid is very important because free nitrogen dioxide can result in oxidation of the methyl group of toluene. This reaction is highly exothermic and carries with it the risk of a runaway reaction leading to an explosion. [citation needed] In the laboratory, 2,4,6-trinitrotoluene is produced by a two-step ...
It is made by nitrating toluene at above -10 °C. This reaction affords a 2:1 mixture of 2-nitro and 4-nitro isomers. [4] Chlorination of 2-nitrotoluene gives two isomers of the chloronitrotoluenes. Similarly nitration gives two isomers of dinitrotoluene. 2-Nitrotoluene is mainly consumed in the production of o-toluidine, a precursor to dyes. [4]
It is made by nitrating toluene by conventional mixed acid (acetyl nitrate doesn't produce it [4]): this reaction mainly affords a 2:1 mixture of 2-nitro and 4-nitro isomers, but after removal of the 2-isomer, the 3-nitrotoluene can be purified by distillation.
The nitration of benzene is achieved via the action of the nitronium ion as the electrophile. The sulfonation with fuming sulfuric acid gives benzenesulfonic acid. Aromatic halogenation with bromine, chlorine, or iodine gives the corresponding aryl halides. This reaction is typically catalyzed by the corresponding iron or aluminum trihalide.