Cumene hydroperoxide
chemical compound
Cumene hydroperoxide is the organic compound with the formula C6H5C(CH3)2OOH; this oily liquid is classified as an organic hydroperoxide. Products of decomposition of cumene hydroperoxide are methylstyrene, acetophenone, and 2-phenylpropan-2-ol.
It is produced by treatment of cumene with oxygen, an autoxidation. At temperatures >100 °C, oxygen is passed through liquid cumene:
C6H5CH(CH3)2 + O2 → C6H5C(CH3)2OOH
Dicumyl peroxide is a side product.
Applications
Cumene hydroperoxide is an intermediate in the cumene process for producing phenol and acetone from benzene and propylene.
Cumene hydroperoxide is a radical initiator for production of acrylates.
Cumene hydroperoxide is involved as an organic peroxide in the production of propylene oxide by the oxidation of propylene. This technology was commercialized by Sumitomo Chemical.
The oxidation by cumene hydroperoxide of propylene affords propylene oxide and the byproduct 2-phenylpropan-2-ol. The reaction follows this stoichiometry:
CH3CHCH2 + C6H5C(CH3)2OOH → CH3CHCH2O + C6H5C(CH3)2OH
Dehydrating and hydrogenating cumyl alcohol recycles the cumene.
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