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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.
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.
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]
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]
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 ( anilines ) are produced from nitro precursors.
While the first nitration, on the activated toluene ring, can be done at room temperature and with dilute acid, the second one, on the deactivated nitrotoluene ring, already needs prolonged heating and more concentrated acid, and the third one, on very strongly deactivated dinitrotoluene, has to be done in boiling concentrated sulfuric acid ...
They can be viewed as nitro derivatives of toluene or as methylated derivatives of nitrobenzene. Mononitrotoluene comes in four isomers, differing by the relative position of the methyl and nitro groups. All are pale yellow with faint fragrances: ortho-nitrotoluene (also called ONT, o-nitrotoluene, or 2-nitrotoluene). m.p. = -10.4 °C
o-Toluidine is produced industrially by nitration of toluene to give a mixture of nitrotoluenes, favoring the ortho isomer.This mixture is separated by distillation. 2-Nitrotoluene is hydrogenated to give o-toluidine.