Cumene hydroperoxide
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Names | |
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IUPAC name
2-hydroperoxypropan-2-ylbenzene
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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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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 an organic hydroperoxide intermediate in the cumene process for synthesizing phenol and acetone from benzene and propene. It is typically used as an oxidizing agent.[2] Products of decomposition of cumene hydroperoxide are methylstyrene, acetophenone, and cumyl alcohol.[3] Its formula is C6H5C(CH3)2OOH.
One of the key uses for the material is as a free radical initiator for acrylate and methacrylate monomers, and polyester resins.
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.[4] Oxidation of cumene affords cumene hydroperoxide
- C
6H
5(CH
3)
2CH + oxidation → C
6H
5(CH
3)
2COOH
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 recycle the cumene.
Public safety
Cumene hydroperoxide[5] is believed to be one of the chemicals of concern[6] at the Arkema facility in Crosby, Texas in the aftermath of Hurricane Harvey.
References
- ^ University, Safety Officer in Physical Chemistry at Oxford (2005). "Safety (MSDS) data for cumene hydroperoxide". 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
- ^ "Summary of Sumitomo process from Nexant Reports". Archived from the original on 2006-01-17. Retrieved 2007-09-18.
{{cite web}}
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suggested) (help) - ^ "The Rachel Maddow Show". MSNBC. 30 August 2017.
- ^ Bagg, Julia; Johnson, Alex; Cumming, Jason (31 August 2017). "Crosby, Texas, Chemical Plant Explodes Twice, Arkema Group Says". nbcnews.com. NBC News. Retrieved 31 August 2017.
Related terms
External links
- Cumene hydroperoxide at International Chemical Safety Cards