Cumene hydroperoxide
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| Names | |
|---|---|
| Preferred IUPAC name
2-Phenylpropane-2-peroxol | |
| Other names
Cumyl hydroperoxide
CHP | |
| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.001.141 
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PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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| 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 | |
| Safety data sheet | sigmaaldrich.com |
| GHS pictograms |     
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| GHS Signal word | Danger |
GHS hazard statements
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H242, H302, H312, H314, H331, H373, H411 |
| P220, P261, P273, P280, P305+351+338, P310 | |
| NFPA 704 (fire diamond) | 
1
2
4 |
| Flash point | 57 °C (135 °F; 330 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
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| Infobox references | |
Cumene hydroperoxide is the organic compound with the formula C6H5CMe2OOH (Me = CH3). An oily liquid, it is classified as an organic hydroperoxide.[2] Products of decomposition of cumene hydroperoxide are methylstyrene, acetophenone, and .[3] Its formula is C6H5C(CH3)2OOH.
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
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.
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.[5]
The oxidation by cumene hydroperoxide of propylene affords propylene oxide and the byproduct cumyl alcohol. 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 as well as a skin-irritant.
References[]
- ^ 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.
- ^ 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)
- ^ Cumene Hydroperoxide at the Organic Chemistry Portal
- ^ 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.
- ^ "Summary of Sumitomo process from Nexant Reports". Archived from the original on 2006-01-17. Retrieved 2007-09-18.
Related terms[]
External links[]
- Cumene hydroperoxide at International Chemical Safety Cards
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- Hydroperoxides