Cyclohexane is a colourless, flammable liquid with a distinctive detergent-like odor, reminiscent of cleaning products (in which it is sometimes used).
[7] On an industrial scale, cyclohexane is produced by hydrogenation of benzene in the presence of a Raney nickel catalyst.
In 1894, Baeyer synthesized cyclohexane starting with a ketonic decarboxylation of pimelic acid followed by multiple reductions: In the same year, E. Haworth and W.H.
The cyclohexanone–cyclohexanol mixture, called "KA oil", is a raw material for adipic acid and caprolactam, precursors to nylon.
Cyclohexane is also used for calibration of differential scanning calorimetry (DSC) instruments, because of a convenient crystal-crystal transition at −87.1 °C.
The idea that the chair conformation is the most stable structure for cyclohexane was first proposed as early as 1890 by Hermann Sachse, but only gained widespread acceptance much later.
The high-temperature phase I, stable between 186 K and the melting point 280 K, is a plastic crystal, which means the molecules retain some rotational degree of freedom.
Two other low-temperature (metastable) phases III and IV have been obtained by application of moderate pressures above 30 MPa, where phase IV appears exclusively in deuterated cyclohexane (application of pressure increases the values of all transition temperatures).