Cumene hydroperoxide

Cumene hydroperoxide[1]
Names
Preferred IUPAC name
2-Phenylpropane-2-peroxol
Other names
Cumyl hydroperoxide
CHP
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.001.141 Edit this at Wikidata
UNII
  • InChI=1S/C9H12O2/c1-9(2,11-10)8-6-4-3-5-7-8/h3-7,10H,1-2H3 checkY
    Key: YQHLDYVWEZKEOX-UHFFFAOYSA-N checkY
  • InChI=1/C9H12O2/c1-9(2,11-10)8-6-4-3-5-7-8/h3-7,10H,1-2H3
    Key: YQHLDYVWEZKEOX-UHFFFAOYAJ
  • OOC(c1ccccc1)(C)C
Properties
C9H12O2
Molar mass 152.193 g·mol−1
Appearance Colorless to pale yellow liquid
Density 1.02 g/cm3
Melting point −9 °C (16 °F; 264 K)
Boiling point 153 °C (307 °F; 426 K)
1.5 g/100 mL
Vapor pressure 14 mmHg, at 20 °C
Hazards
GHS labelling:
GHS02: Flammable GHS05: Corrosive GHS06: Toxic GHS08: Health hazard GHS09: Environmental hazard
Danger
H242, H302, H312, H314, H331, H373, H411
P220, P261, P273, P280, P305+P351+P338, P310
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 4: Readily capable of detonation or explosive decomposition at normal temperatures and pressures. E.g. nitroglycerinSpecial hazards (white): no code
1
2
4
Flash point 57 °C (135 °F; 330 K)
Safety data sheet (SDS) sigmaaldrich.com
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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.