Cumene hydroperoxide is the organic compound with the formula C6H5C(CH3)2OOH. An oily liquid, it is classified as an organic hydroperoxide.[1] Products of decomposition of cumene hydroperoxide are methylstyrene, acetophenone, and 2-phenyl-2-propanol.[2]
It is produced by treatment of cumene with oxygen, an autoxidation. At temperatures >100 °C, oxygen is passed through liquid cumene:[3]
+ O2 → Dicumyl peroxide is a side product.
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.[4]
Cumene hydroperoxide is involved as an organic peroxide in the manufacturing of propylene oxide by the oxidation of propylene. This technology was commercialized by Sumitomo Chemical.[5]
The oxidation by cumene hydroperoxide of propylene affords propylene oxide and the byproduct 2-phenyl-2-propanol. The reaction follows this stoichiometry:
+ → +
Dehydrating and hydrogenating cumyl alcohol recycles the cumene.
Cumene hydroperoxide, like all organic peroxides, is potentially explosive. It is also toxic, corrosive and flammable as well as a skin-irritant.[6]