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Chemical structure of the alkylphenol nonylphenol. Alkylphenols are a family of organic compounds obtained by the alkylation of phenols.The term is usually reserved for commercially important propylphenol, butylphenol, amylphenol, heptylphenol, octylphenol, nonylphenol, dodecylphenol and related "long chain alkylphenols" (LCAPs).
Via the Hock rearrangement, cyclohexylbenzene hydroperoxide cleaves to give phenol and cyclohexanone. Cyclohexanone is an important precursor to some nylons. [8] Starting with the alkylation of benzene with mixture of 1 and 2-butenes, the cumene process produces phenol and butanones. [5]
Many phenols of commercial interest are prepared by elaboration of phenol or cresols. They are typically produced by the alkylation of benzene/toluene with propylene to form cumene then O 2 is added with H 2 SO 4 to form phenol (Hock process). In addition to the reactions above, many other more specialized reactions produce phenols:
Alkylation is a chemical reaction that entails transfer of an alkyl group. The alkyl group may be transferred as an alkyl carbocation , a free radical , a carbanion , or a carbene (or their equivalents).
It can be prepared by acid-catalyzed alkylation of phenol with isobutene, 2-tert-butylphenol being the major side product. It can be produced by diverse transalkylation reactions. Uses
Nonylphenol can be produced industrially, naturally, and by the environmental degradation of alkylphenol ethoxylates. Industrially, nonylphenols are produced by the acid-catalyzed alkylation of phenol with a mixture of nonenes. This synthesis leads to a very complex mixture with diverse nonylphenols.
The butylation of phenol is typically achieved by a Friedel-Crafts alkylation with isobutylene catalysed by a strong acid. These acids can be either liquids like triflic acid, or solid acids such as zeolites.
Because, however, the product ketone forms a rather stable complex with Lewis acids such as AlCl 3, a stoichiometric amount or more of the "catalyst" must generally be employed, unlike the case of the Friedel–Crafts alkylation, in which the catalyst is constantly regenerated. [13] Reaction conditions are similar to the Friedel–Crafts ...