Cumene hydroperoxide

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.

Cumene hydroperoxide[1]
Names
IUPAC name
2-hydroperoxypropan-2-ylbenzene
Other names
Cumyl Hydroperoxide
CHP
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.001.141
UNII
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
GHS Signal word Danger
GHS hazard statements
 H242, H302, H312, H314, H331, H373, H411
P220, P261, P273, P280, P305+351+338, P310
NFPA 704 (fire diamond)
Flammability code 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 fuelHealth code 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineReactivity code 4: Readily capable of detonation or explosive decomposition at normal temperatures and pressures. E.g. nitroglycerinSpecial hazards (white): no code
2
1
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).
N verify (what is YN ?)
Infobox references

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 recycles 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.

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References
  1. 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.
  2. 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)
  3. Cumene Hydroperoxide at the Organic Chemistry Portal
  4. "Summary of Sumitomo process from Nexant Reports". Archived from the original on 2006-01-17. Retrieved 2007-09-18.
  5. "The Rachel Maddow Show". MSNBC. 30 August 2017.
  6. 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.
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