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The direct oxidation of benzene (C 6 H 6) to phenol is possible, but it has not been commercialized: C 6 H 6 + O → C 6 H 5 OH Nitrous oxide is a potentially "green" oxidant that is a more potent oxidant than O 2 .
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:
Similar to other phenols, the hydroxyl groups on the aromatic ring of a benzenediol are weakly acidic. Each benzenediol can lose an H + from one of the hydroxyls to form a type of phenolate ion. The Dakin oxidation is an organic redox reaction in which an ortho - or para -hydroxylated phenyl aldehyde ( −CH=O ) or ketone ( >C=O ) reacts with ...
Benzene can be easily converted to chlorobenzene by nucleophilic aromatic substitution via a benzyne intermediate. [1] It is treated with aqueous sodium hydroxide at 350 °C and 300 bar or molten sodium hydroxide at 350 °C to convert it to sodium phenoxide, which yields phenol upon acidification. [2]
Cumene hydroperoxide is an intermediate in the cumene process for producing phenol and acetone from benzene and propene. Cumene hydroperoxide is a free radical initiator for production of acrylates. [5] Cumene hydroperoxide is involved as an organic peroxide in the manufacturing of propylene oxide by the oxidation of propylene. This technology ...
The first stage of Fenton's reaction (oxidation of Fe 3+ with hydrogen peroxide) is used in Haber–Weiss reaction; Fenton's reagent can be used in organic synthesis reactions: e.g. hydroxylation of arenes via a free radical substitution; Conversion of benzene into phenol by using Fenton's reagent; Oxidation of barbituric acid into alloxan.
Substrates containing two phenols (or an aniline and a phenol; see equation (8) below for a related example), undergo oxidative coupling in the presence of hypervalent iodine(III) reagents. Coupling of both the ortho and para positions is possible; however, the use of bulky silyl-protected phenols provides complete selectivity for para coupling ...