Cumene hydroperoxide explained

Cumene hydroperoxide is the organic compound with the formula C6H5C(CH3)2OOH. An oily liquid, it is classified as an organic hydroperoxide.[1] Products of decomposition of cumene hydroperoxide are methylstyrene, acetophenone, and 2-phenyl-2-propanol.[2]

It is produced by treatment of cumene with oxygen, an autoxidation. At temperatures >100 °C, oxygen is passed through liquid cumene:[3]

+ O2Dicumyl 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 free radical initiator for production of acrylates.[4]

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.[5]

The oxidation by cumene hydroperoxide of propylene affords propylene oxide and the byproduct 2-phenyl-2-propanol. 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.[6]

Related terms

External links

Notes and References

  1. Richard J. Lewis, Richard J. Lewis (Sr.), Hazardous chemicals desk reference, Publisher Wiley-Interscience, 2008,,, 1953 pages (page 799)
  2. https://www.organic-chemistry.org/chemicals/oxidations/cumene-hydroperoxide-cmhp.shtm Cumene Hydroperoxide
  3. Book: Syntheses and Uses of Hydroperoxides and Dialkylperoxides . Saul . Patai . Roger A. Sheldon . 1983 . John Wiley & Sons . 10.1002/9780470771730.ch6. PATAI'S Chemistry of Functional Groups.
  4. Web site: April 2003 . Hazardous substance fact sheet: Cumene Hydroperoxide . New Jersey Government.
  5. Web site: Summary of Sumitomo process from Nexant Reports. 2007-09-18. dead. https://archive.today/20060117092104/http://nexant.ecnext.com/coms2/gi_0255-227/Developments-in-Propylene-Oxide-Technology.html. 2006-01-17.
  6. Web site: PubChem . Cumene hydroperoxide . 2022-04-25 . pubchem.ncbi.nlm.nih.gov . en.