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Toluene, also known as toluol  is an aromatic hydrocarbon. It is a colorless, water-insoluble liquid with the smell associated with paint thinners. It is a mono-substituted benzene derivative, consisting of a CH3 group attached to a phenyl group. As such, its IUPAC systematic name is methylbenzene. Toluene is predominantly used as an industrial feedstock and a solvent.

As the solvent in some types of paint thinner, contact cement and model airplane glue, toluene is sometimes used as a recreational inhalant  and has the potential of causing severe neurological harm.

Other names

Phenyl methane
Toluol
Anisen

Production

Toluene occurs naturally at low levels in crude oil and is a byproduct in the production of gasoline by a catalytic reformer or ethylene cracker; It is also a byproduct of the production of coke from coal. Final separation and purification is done by any of the distillation or solvent extraction processes used for BTX aromatics (benzene, toluene, and xylene isomers).

Uses

Toluene is mainly used as a precursor to benzene via hydrodealkylation:

C6H5CH3 + H2 → C6H6 + CH4

The second ranked application involves its disproportionation to a mixture of benzene and xylene. When oxidized it yields benzaldehyde and benzoic acid, two important intermediates. In addition to the synthesis of benzene and xylene, toluene is a feedstock for toluene diisocyanate (used in the manufacture of polyurethane foam), trinitrotoluene (the explosive, TNT), and a number of synthetic drugs.

Explosive

Trinitrotoluene explosive synthesis requires toluene. Toluene is nitrated to dinitrotoluene, which is then nitrated to trinitrotoluene.

Foam

Toluene is needed for dinitrotoluene, which is needed for toluene diisocyanate, which is used to produce polyurethane foams.

Solvent

Toluene is a common solvent, e.g. for paints, paint thinners, silicone sealants, many chemical reactants, rubber, printing ink, adhesives (glues), lacquers, leather tanners, and disinfectants.

Niche applications

In the laboratory, toluene is used as a solvent for carbon nanomaterials, including nanotubes and fullerenes, and it can also be used as a fullerene indicator. The color of the toluene solution of C60 is bright purple. Toluene is used as a cement for fine polystyrene kits (by dissolving and then fusing surfaces) as it can be applied very precisely by brush and contains none of the bulk of an adhesive. Toluene can be used to break open red blood cells in order to extract hemoglobin in biochemistry experiments. Toluene has also been used as a coolant for its good heat transfer capabilities in sodium cold traps used in nuclear reactor system loops.