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Phenol
Phenol, also known under the old name carbolic acid, is a colorless crystallinesolidwith a typical sweet tarry odor. Its chemical formulais C6H5OHand its structure is that of a hydroxylgroup(-OH) bondedto a phenyl ring; it is thus an aromatic compound. The word phenol is also used to refer in general to an aromatic compound in which a hydroxyl group(-OH) is bonded directly to a six-membered aromatic ring. In effect, phenols are a class of organic compoundsof which the phenol discussed in this article is the simplest member. For more information on this class, see Phenols. Phenol has a limited solubilityin water (8.3 g/100 ml). It is slightly acidic: the phenol molecule has weak tendencies to lose the H+ ion from the hydroxyl group, resulting in the highly water-soluble phenolate anionC6H5O−. Phenol can be made from the partial oxidationof benzene, by the cumene process, or by the Raschig process. It can also be found as a product of coaloxidation. Phenol has antisepticproperties, and was used by Sir Joseph Listerin his pioneering technique of antiseptic surgery, though the skin irritation caused by continual exposure to phenol eventually led to the substitution of aseptic (germ-free) techniques in surgery. It is one of the main components of the commercial antiseptic TCP. Phenol has anestheticproperties, and is the active ingredient in some oral anesthetics such as Chloraseptic®spray. It is also used in the production of drugs (it is the starting material in the industrial production of aspirin), weedkillers, and syntheticresins (Bakelite, one of the first synthetic resins to be manufactured, is a polymerof phenol with formaldehyde). Exposure of the skin to concentrated phenol solutions causes chemical burns which may be severe; in laboratorieswhere it is used, it is usually recommended that polyethylene glycolsolution is kept available for washing off splashes. Washing with large amounts of plain water (most labs have a safety shower or eye-wash) and removal of contaminated clothing are required, and immediate ER treatment for large splashes; particularly if the phenol is mixed with chloroform(a commonly used mixture in molecular biology for DNA purification). Notwithstanding the effects of concentrated solutions, it is also used in cosmetic surgeryas an exfoliant, to remove layers of dead skin. During the Second World WarJosef Mengeleinjected it directly into the heart of concentration campprisoners in order to kill them. Compared to aliphaticalcohols, phenol shows higher acidity. This is due to the mesomeric effect. See also
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