Phenol

Phenol, also known under the old name carbolic acid, is a colorless crystalline solid with a typical sweet tarry odor. Phenol has a low solubility in water (8.3 g/100 ml). Phenol is an aromatic alcohol that is more acidic than aliphatic alcohols. It deprotonates in the presence of strongly alkaline solutions, resulting in the highly water soluble phenolate anion.

Phenol can be made from the partial oxidation of benzene, by the cumene process, or by the Raschig process. It can also be found as a product of coal oxidation.

Phenol has antiseptic properties, and was used by Sir Joseph Lister in his pioneering technique of antiseptic surgery, though the skin irritation caused by continual exposure to phenol eventually lead to the substitution of aseptic (germ-free) techniques in surgery.

It is used as a disinfectant and in the production of drugs, weedkillers, and synthetic resins - Bakelite, one of the first synthetic resins to be manufactured, is a polymer of phenol with formaldehyde. Exposure of the skin to concentrated phenol solutions causes chemical burns; in laboratories where it is used, it is usually recommended that polyethylene glycol solution is kept available for washing off splashes. Notwithstanding the effects of concentrated solutions, it is also used in cosmetic surgery as an exfoliant, to remove layers of dead skin.

Mesomeric structures of phenol, resulting in a partial positive charge δ⁺ on the oxygen atom. This together with the mesomeric stabilization of the phenolate anion causes an enhanced acidity.

Phenol is the first starting material in the industrially used three-step process to produce aspirin.

Dr. John H. Kellogg, the brother of Will Keith Kellogg who founded the Kellogg Company, advocated the application of "pure carbolic acid (phenol) on the clitoris of females to prevent masturbation in children".

See also

• Phenols