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Cumene is oxidized in air, which removes the tertiary benzylic hydrogen from cumene and hence forms a cumene radical: The cumene radical then bonds with an oxygen molecule to give cumene peroxide radical, which in turn forms cumene hydroperoxide (C 6 H 5 C(CH 3) 2 O 2 H) by abstracting a benzylic hydrogen from another cumene molecule. This ...
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Acetophenone is formed as a byproduct of the cumene process, the industrial route for the synthesis of phenol and acetone.In the Hock rearrangement of isopropylbenzene hydroperoxide, migration of a methyl group rather than the phenyl group gives acetophenone and methanol as a result of an alternate rearrangement of the intermediate:
Products of decomposition of cumene hydroperoxide are methylstyrene, acetophenone, and 2-phenylpropan-2-ol. [3] It is produced by treatment of cumene with oxygen, an autoxidation. At temperatures >100 °C, oxygen is passed through liquid cumene: [4] C 6 H 5 CH(CH 3) 2 + O 2 → C 6 H 5 C(CH 3) 2 OOH. Dicumyl peroxide is a side product.
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In commercial applications, the alkylating agents are generally alkenes, some of the largest scale reactions practiced in industry.Such alkylations are of major industrial importance, e.g. for the production of ethylbenzene, the precursor to polystyrene, from benzene and ethylene and for the production of cumene from benzene and propene in cumene process:
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