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Cumene hydroperoxide

Aromatic organic chemical compound From Wikipedia, the free encyclopedia

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]

Quick Facts Names, Identifiers ...
Cumene hydroperoxide[1]
Thumb
Names
Preferred IUPAC name
2-Phenylpropane-2-peroxol
Other names
Cumyl hydroperoxide
CHP
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.001.141
UNII
  • 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
  • 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)
ThumbHealth 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 YN ?)
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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.

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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]

References

Related terms

External links

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