Cumene hydroperoxide
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| Names | |
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| 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 |
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 | |
| GHS labelling: | |
    
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| Danger | |
| H242, H302, H312, H314, H331, H373, H411 | |
| P220, P261, P273, P280, P305+P351+P338, P310 | |
| NFPA 704 (fire diamond) | |
| 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. 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]
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
[edit]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
[edit]Cumene hydroperoxide, like all organic peroxides, is potentially explosive. It is also toxic, corrosive and flammable as well as a skin-irritant.[7]
References
[edit]- ^ 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.
- ^ "Hazardous substance fact sheet: Cumene Hydroperoxide" (PDF). New Jersey Government. April 2003.
- ^ "Summary of Sumitomo process from Nexant Reports". Archived from the original on 2006-01-17. Retrieved 2007-09-18.
- ^ PubChem. "Cumene hydroperoxide". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-04-25.
Related terms
[edit]- Cumene process
- 2-hydroperoxypropan-2-ylbenzene
External links
[edit]- Cumene hydroperoxide at International Chemical Safety Cards
| Authority control databases: National |
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