Cumene hydroperoxide
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Names | |
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Preferred IUPAC name 2-Phenylpropane-2-peroxol | |
Other names Cumyl hydroperoxide CHP | |
Identifiers | |
CAS Number |
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3D model (JSmol) |
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ChEBI |
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ChemSpider |
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ECHA InfoCard | 100.001.141 ![]() |
PubChem CID |
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UNII |
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CompTox Dashboard (EPA) |
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InChI
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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 | ![]() ![]() ![]() ![]() ![]() |
Danger | |
Hazard statements | H242, H302, H312, H314, H331, H373, H411 |
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). ![]() ![]() ![]() Infobox references |
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
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
- ^ 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
- Cumene process
- 2-hydroperoxypropan-2-ylbenzene
External links
- Cumene hydroperoxide at International Chemical Safety Cards