Cumene hydroperoxide

Cumene hydroperoxide is the organic compound with the formula C₆H₅C(CH₃)₂OOH; this oily liquid is classified as an organic hydroperoxide.^[2] Products of decomposition of cumene hydroperoxide are methylstyrene, acetophenone, and 2-phenylpropan-2-ol.^[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
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 propene.

Cumene hydroperoxide is a radical initiator for production of acrylates.^[5]

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.^[6]

The oxidation by cumene hydroperoxide of propene 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.^[7]