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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.
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.
Fuel
Toluene can be used as an octane booster in gasoline fuels for internal combustion engines. Toluene at 86% by volume fuelled all the turbocharged engines in Formula One during the 1980s, first pioneered by the Honda team. The remaining 14% was a "filler" of n-heptane, to reduce the octane to meet Formula One fuel restrictions. Toluene at 100% can be used as a fuel for both two-stroke and four-stroke engines; however, due to the density of the fuel and other factors, the fuel does not vaporize easily unless preheated to 70 °C (158 °F). Honda solved this problem in their Formula One cars by routing the fuel lines through a heat exchanger, drawing energy from the water in the cooling system to heat the fuel.
In Australia in 2003, toluene was found to have been illegally combined with petrol in fuel outlets for sale as standard vehicular fuel. Toluene incurs no fuel excise tax, while other fuels are taxed at more than 40%, providing a greater profit margin for fuel suppliers. The extent of toluene substitution has not been determined.
Toluene is one of a group of fuels that have included in jet fuel surrogate blends. Toluene is used as a jet fuel surrogate for its content of aromatic compounds.
Recreational use
Toluene is used as an intoxicative inhalant in a manner unintended by manufacturers. People inhale toluene-containing products (e.g., paint thinner, contact cement, model glue, etc.) for its intoxicating effect. The possession and use of toluene and products containing it are regulated in many jurisdictions, for the supposed reason of preventing minors from obtaining these products for recreational drug purposes. As of 2007, 24 U.S. states had laws penalizing use, possession with intent to use, and/or distribution of such inhalants. In 2005 the European Union banned the general sale of products consisting of greater than 0.5% toluene.