Cumene hydroperoxide

Cumene hydroperoxide
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: FlammableGHS05: CorrosiveGHS06: ToxicGHS08: Health hazardGHS09: 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).
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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. 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:

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

Dicumyl peroxide is a side product.

Applications

Cumene hydroperoxide is an intermediate in the cumene process for producing phenol and acetone from benzene and propylene.

Overview of the cumene process

Cumene hydroperoxide is a radical initiator for production of acrylates.

Cumene hydroperoxide is involved as an organic peroxide in the production of propylene oxide by the oxidation of propylene. This technology was commercialized by Sumitomo Chemical.

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

CH
3CHCH
2 + C
6H
5C(CH
3)
2OOH → CH
3CHCH
2O + C
6H
5C(CH
3)
2OH

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.

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". Retrieved 2007-09-18.{{cite web}}: CS1 maint: deprecated archival service (link)
  7. ↑ PubChem. "Cumene hydroperoxide". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-04-25.