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 C
6H
5C(CH
3)
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:
: + O
2 →
Dicumyl 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 hydroperoxideat International Chemical Safety Cards
{{Authority control
Hydroperoxides