Methylcyclohexane

While researching hydrogenation of arenes with hydroiodic acid in 1876[6] as part of his doctoral dissertation,[7] Felix Wreden [ru] first prepared the hydrocarbon from toluene.

[9] Most methylcyclohexane is extracted from petroleum but it can be also produced by catalytic hydrogenation of toluene: The hydrocarbon is a minor component of automobile fuel, with its share in US gasoline varying between 0.3 and 1.7% in early 1990s[10] and 0.1 to 1% in 2011.

[14][15] Methylcyclohexane is used as an organic solvent, with properties similar to related saturated hydrocarbons such as heptane.

The lowest energy form of this monosubstituted methylcyclohexane occurs when the methyl group occupies an equatorial rather than an axial position.

[17] Note, while methylcyclohexane is a substructure of 4-methylcyclohexanemethanol (MCHM), it is distinct in its physical, chemical, and biological (ecologic, metabolic, and toxicologic) properties.

NFPA 704 four-colored diamond Health 1: Exposure would cause irritation but only minor residual injury. E.g. turpentine Flammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasoline Instability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogen Special hazards (white): no code
The conversion of methylcyclohexane to toluene is a classic aromatization reaction. This platinum (Pt)-catalyzed process is practiced on scale in the production of gasoline from petroleum. [ 13 ]