Cumene hydroperoxide is the organic compound 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:
C6H5CH(CH3)2 + O2 → C6H5C(CH3)2OOHDicumyl 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.4
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.5
The oxidation by cumene hydroperoxide of propene affords propylene oxide and the byproduct 2-phenylpropan-2-ol. The reaction follows this stoichiometry:
CH3CHCH2 + C6H5C(CH3)2OOH → CH3CHCH2O + C6H5C(CH3)2OHDehydrating 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.6
Related terms
External links
- Cumene hydroperoxide at International Chemical Safety Cards
References
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) /wiki/ISBN_(identifier) ↩
Cumene Hydroperoxide at the Organic Chemistry Portal https://www.organic-chemistry.org/chemicals/oxidations/cumene-hydroperoxide-cmhp.shtm ↩
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. /wiki/Doi_(identifier) ↩
"Hazardous substance fact sheet: Cumene Hydroperoxide" (PDF). New Jersey Government. April 2003. https://www.nj.gov/health/eoh/rtkweb/documents/fs/0543.pdf ↩
"Summary of Sumitomo process from Nexant Reports". Archived from the original on 2006-01-17. Retrieved 2007-09-18. https://archive.today/20060117092104/http://nexant.ecnext.com/coms2/gi_0255-227/Developments-in-Propylene-Oxide-Technology.html ↩
PubChem. "Cumene hydroperoxide". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-04-25. https://pubchem.ncbi.nlm.nih.gov/compound/6629 ↩