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Cumene hydroperoxide is the
organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
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: : + O2Dicumyl peroxide is a side product.


Applications

Cumene hydroperoxide is an intermediate in the cumene process for producing
phenol Phenol (also known as carbolic acid, phenolic acid, or benzenol) is an aromatic organic compound with the molecular formula . It is a white crystalline solid that is volatile and can catch fire. The molecule consists of a phenyl group () ...
and
acetone Acetone (2-propanone or dimethyl ketone) is an organic compound with the chemical formula, formula . It is the simplest and smallest ketone (). It is a colorless, highly Volatile organic compound, volatile, and flammable liquid with a charact ...
from
benzene Benzene is an Organic compound, organic chemical compound with the Chemical formula#Molecular formula, molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar hexagonal Ring (chemistry), ring with one hyd ...
and propene. : 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 propene. This technology was commercialized by Sumitomo Chemical. The oxidation by cumene hydroperoxide of propene 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 {{Authority control Hydroperoxides