Cumene hydroperoxide

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]

Cumene hydroperoxide^[1]

Names
Preferred IUPAC name 2-Phenylpropane-2-peroxol
Other names Cumyl hydroperoxide CHP
Identifiers
CAS Number	80-15-9 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:78673 N
ChemSpider	6377 Y
ECHA InfoCard	100.001.141
PubChem CID	6629
UNII	PG7JD54X4I Y
CompTox Dashboard (EPA)	DTXSID3024869
InChI InChI=1S/C9H12O2/c1-9(2,11-10)8-6-4-3-5-7-8/h3-7,10H,1-2H3 Y Key: YQHLDYVWEZKEOX-UHFFFAOYSA-N Y InChI=1/C9H12O2/c1-9(2,11-10)8-6-4-3-5-7-8/h3-7,10H,1-2H3 Key: YQHLDYVWEZKEOX-UHFFFAOYAJ
SMILES OOC(c1ccccc1)(C)C
Properties
Chemical formula	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)
Solubility in water	1.5 g/100 mL
Vapor pressure	14 mmHg, at 20 °C
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H242, H302, H312, H314, H331, H373, H411
Precautionary statements	P220, P261, P273, P280, P305+P351+P338, P310
NFPA 704 (fire diamond)	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 YN ?) Infobox references

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.

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

• Cumene process
• 2-hydroperoxypropan-2-ylbenzene

External links

• Cumene hydroperoxide at International Chemical Safety Cards