Cyclohexanol is the

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with the

formula In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwe ...

HOCH(CH₂)₅. The molecule is related to

cyclohexane Cyclohexane is a cycloalkane with the molecular formula . Cyclohexane is non-polar. Cyclohexane is a colourless, flammable liquid with a distinctive detergent-like odor, reminiscent of cleaning products (in which it is sometimes used). Cyclohexan ...

by replacement of one hydrogen atom by a hydroxyl group. This compound exists as a

deliquescent Hygroscopy is the phenomenon of attracting and holding water molecules via either absorption (chemistry), absorption or adsorption from the surrounding Natural environment, environment, which is usually at normal or room temperature. If water mol ...

colorless solid with a camphor-like odor, which, when very pure, melts near room temperature. Millions of tonnes are produced annually, mainly as a precursor to

nylon Nylon is a family of synthetic polymers characterised by amide linkages, typically connecting aliphatic or Polyamide#Classification, semi-aromatic groups. Nylons are generally brownish in color and can possess a soft texture, with some varieti ...

.Michael Tuttle Musser "Cyclohexanol and Cyclohexanone" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005.

Production

Cyclohexanol is produced by the

oxidation Redox ( , , reduction–oxidation or oxidation–reduction) is a type of chemical reaction in which the oxidation states of the reactants change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is ...

in air, typically using cobalt catalysts: :2 C₆H₁₂ + O₂ → 2 C₆H₁₁OH This process coforms cyclohexanone, and this mixture ("KA oil" for ketone-alcohol oil) is the main feedstock for the production of adipic acid. The oxidation involves radicals and the intermediacy of the hydroperoxide C₆H₁₁O₂H. Alternatively, cyclohexanol can be produced by the

hydrogenation Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to redox, reduce or Saturated ...

phenol Phenol (also known as carbolic acid, phenolic acid, or benzenol) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile and can catch fire. The molecule consists of a phenyl group () ...

: :C₆H₅OH + 3 H₂ → C₆H₁₁OH This process can also be adjusted to favor the formation of cyclohexanone.

Basic reactions

Cyclohexanol undergoes the main reactions expected for a secondary alcohol. Oxidation gives cyclohexanone, which is converted on a large scale in industry to the oxime, a precursor to caprolactam. As a laboratory exercise, this oxidation can be effected with chromic acid. Esterification affords the commercially useful derivatives dicyclohexyladipate and dicyclohexylphthalate, which are used as plasticizers. Heating in the presence of acid catalysts converts cyclohexanol to

cyclohexene Cyclohexene is a hydrocarbon with the formula . It is a cycloalkene. At room temperature, cyclohexene is a colorless liquid with a sharp odor. Among its uses, it is an chemical intermediate, intermediate in the commercial synthesis of nylon. Prod ...

Structure

Cyclohexanol has at least two solid phases. One of them is a plastic crystal.

Applications

As indicated above, cyclohexanol is an important feedstock in the polymer industry, firstly as a precursor to

s, but also to various

plasticizers A plasticizer (British English, UK: plasticiser) is a substance that is added to a material to make it softer and more flexible, to increase its plasticity (physics), plasticity, to decrease its viscosity, and/or to decrease friction during its ...

. Small amounts are used as a

solvent A solvent (from the Latin language, Latin ''wikt:solvo#Latin, solvō'', "loosen, untie, solve") is a substance that dissolves a solute, resulting in a Solution (chemistry), solution. A solvent is usually a liquid but can also be a solid, a gas ...

Safety

Cyclohexanol is moderately toxic: the Threshold Limit Value for the vapor for 8 h is 50 ppm. The IDLH concentration is set at 400 ppm, based on studies on the acute oral toxicity in animals. Few studies have been done on its carcinogenicity, but one study on rats found it to have co-carcinogenic effects.
Lucrecia Márquez-Rosado, Cristina Trejo-Solís 2, María del Pilar Cabrales-Romero, Evelia Arce-Popoca, Adolfo Sierra-Santoyo, Leticia Alemán-Lazarini, Samia Fatel-Fazenda, Claudia E. Carrasco-Legleu, Saúl Villa-Treviño, "Co-carcinogenic effect of cyclohexanol on the development of preneoplastic lesions in a rat hepatocarcinogenesis model", ''Molecular Carcinogenesis'', Vol. 46, No. 7, Pages 524 - 533, March 2007.

References

{{Chemical agents Cyclohexyl compounds Cyclohexanols Nerve agent precursors