Cumene hydroperoxide is the organic compound with the formula C6H5C(CH3)2OOH; this oily liquid is classified as an organic hydroperoxide.Richard J. Lewis, Richard J. Lewis (Sr.), Hazardous chemicals desk reference, Publisher Wiley-Interscience, 2008, , , 1953 pages (page 799) Products of decomposition of cumene hydroperoxide are methylstyrene, acetophenone, and 2-phenylpropan-2-ol.Cumene Hydroperoxide at the Organic Chemistry Portal
It is produced by treatment of cumene with oxygen, an autoxidation. At temperatures >100 °C, oxygen is passed through liquid cumene: + O2 → 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: + → +
Dehydrating and hydrogenating cumyl alcohol recycles the cumene.
Safety Cumene hydroperoxide, like all organic peroxides, is potentially explosive. It is also toxic, corrosive and flammable as well as a skin-irritant.
References
Related terms Cumene process
External links Cumene hydroperoxide at International Chemical Safety Cards