·
Linear Formula C6H5OH
·
Molecular Weight 94.11
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Beilstein Registry Number 969616
Phenol, also known as carbolic
acid, is an aromatic organic
compound with the molecular formula C6H5OH. It is a white crystallinesolid that is volatile. The molecule consists of a phenyl group (−C6H5) bonded to a hydroxyl group (−OH). It is mildly acidic and requires careful handling due to its propensity to cause chemical burns.
Detailed description
Phenol was first extracted from coal tar,
but today is produced on a large scale (about 7 billion kg/year) from petroleum. It is an important industrial commodity as a precursor to many materials and useful compounds.[7] It is primarily used to synthesize plastics and related materials. Phenol and its chemical derivatives are essential for production of polycarbonates, epoxies, Bakelite, nylon, detergents, herbicides such as phenoxy herbicides, and numerous pharmaceutical drugs.
Uses
The major uses of phenol, consuming two thirds of
its production, involve its conversion to precursors for plastics. Condensation with acetone gives bisphenol-A, a key precursor to polycarbonates and epoxide resins. Condensation of phenol, alkylphenols,
or diphenols with formaldehyde gives phenolic resins, a famous example of which is Bakelite. Partial hydrogenation of phenol gives cyclohexanone, a precursor to nylon. Nonionic detergents are produced by
alkylation of phenol to give the alkylphenols, e.g., nonylphenol, which are then subjected to ethoxylation.[7]
Phenol is also a versatile precursor to a large
collection of drugs, most notably aspirin but also many herbicides and pharmaceutical drugs.
Phenol is a component in liquid/liquid phenol–chloroform
extraction technique used in molecular biology for obtaining nucleic acids from tissues or cell
culture samples. Depending on the pH of the solution either DNA or RNA can be extracted.
Medical
Phenol once was widely used as an antiseptic, its
use pioneered by Joseph Lister (see section History).
From the early 1900s to the 1970s it was used as a
soap, known as carbolic soap. Concentrated
phenol liquids are commonly used for permanent treatment of ingrown toe and
finger nails, a procedure known as a chemical matrixectomy. The procedure was first
described by Otto Boll in 1945. Since that time it has become the chemical of
choice for chemical matrixectomies performed by podiatrists. Phenol is also
used as a preservative in some vaccines.[19]
Phenol spray is used medically to help sore throat.[20] It is the active
ingredient in some oral analgesics such as Chloraseptic spray
and Carmex, commonly used to temporarily treat pharyngitis.[21]
Niche uses
Phenol is so inexpensive that it attracts many
small-scale uses. It is a component of industrial paint strippers used in the aviation
industry for the removal of epoxy, polyurethane and other chemically resistant
coatings.[22]
Phenol derivatives are also used in the preparation
of cosmetics including sunscreens,[23] hair colorings, and skin lightening preparations.
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