REACTIONS AND CHEMICALS OF TOLUENE

Toluene (methylbenzene) is similar to benzene as a mononuclear aromatic, but it is more active due to presence of the electron-donating methyl group. However, toluene is much less useful than benzene because it produces more polysubstituted products. Most of the toluene extracted for chemical use is converted to benzene via dealkylation or disproportionation. The rest is used to produce a limited number of petrochemicals.

The main reactions related to the chemical use of toluene (other than conversion to benzene) are the oxidation of the methyl substituent and the hydrogenation of the phenyl group. Electrophilic substitution is limited to the nitration of toluene for producing mononitrotoluene and dinitrotoluenes. These compounds are important synthetic intermediates.

The 1994 U.S. toluene production (of all grades) was approximately 6.8 billion pounds. Hydrodealkylating toluene to benzene was the largest end use in United States and West Europe, followed by solvent applications.