Cumene hydroperoxide is the organic compound with the formula C6H5C(CH3)2OOH. An oily liquid, it is classified as an organic hydroperoxide.[2] Products of decomposition of cumene hydroperoxide are methylstyrene, acetophenone, and 2-Phenyl-2-propanol.[3]

It is produced by treatment of cumene with oxygen, an autoxidation. At temperatures >100 °C, oxygen is passed through liquid cumene:[4]

C
6H
5(CH
3)
2CH + O2 → C
6H
5(CH
3)
2COOH

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.

Overview of the cumene process

Cumene hydroperoxide is a free radical initiator for production of acrylates.[5]

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.[6]

The oxidation by cumene hydroperoxide of propylene affords propylene oxide and the byproduct 2-Phenyl-2-propanol. The reaction follows this stoichiometry:

CH
3CHCH
2 + C
6H
5(CH
3)
2COOH → CH
3CHCH
2O + C
6H
5(CH
3)
2COH

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

  1. ^ University, Safety Officer in Physical Chemistry at Oxford (2005). "Safety (MSDS) data for cumene hydroperoxide". Archived from the original on 2009-02-28. Retrieved 2009-05-13.
  2. ^ Richard J. Lewis, Richard J. Lewis (Sr.), Hazardous chemicals desk reference, Publisher Wiley-Interscience, 2008, ISBN 0-470-18024-2, ISBN 978-0-470-18024-2, 1953 pages (page 799)
  3. ^ Cumene Hydroperoxide at the Organic Chemistry Portal
  4. ^ Roger A. Sheldon (1983). Patai, Saul (ed.). Syntheses and Uses of Hydroperoxides and Dialkylperoxides. PATAI'S Chemistry of Functional Groups. John Wiley & Sons. doi:10.1002/9780470771730.ch6.
  5. ^ "Hazardous substance fact sheet: Cumene Hydroperoxide" (PDF). New Jersey Government. April 2003.
  6. ^ "Summary of Sumitomo process from Nexant Reports". Archived from the original on 2006-01-17. Retrieved 2007-09-18.
  7. ^ PubChem. "Cumene hydroperoxide". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-04-25.

Related terms

External links