Cumene hydroperoxide
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| Appearance | Colorless to pale yellow liquid |
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Cumene hydroperoxide is the organic compound with the formula C6H5C(CH3)2OOH; this oily liquid is classified as an organic hydroperoxide.[2] Products of decomposition of cumene hydroperoxide are methylstyrene, acetophenone, and 2-phenylpropan-2-ol.[3]
It is produced by treatment of cumene with oxygen, an autoxidation. At temperatures >100 °C, oxygen is passed through liquid cumene:[4]
Dicumyl peroxide is a side product.
Applications
Cumene hydroperoxide is an intermediate in the cumene process for producing phenol and acetone from benzene and propene.
Cumene hydroperoxide is a radical initiator for production of acrylates.[5]
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.[6]
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.[7]
References
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- ↑ Richard J. Lewis, Richard J. Lewis (Sr.), Hazardous chemicals desk reference, Publisher Wiley-Interscience, 2008, Template:ISBN, Template:ISBN, 1953 pages (page 799)
- ↑ Cumene Hydroperoxide at the Organic Chemistry Portal
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Related terms
External links
- Cumene hydroperoxide at International Chemical Safety Cards
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