Chemistry:Cumene hydroperoxide

From HandWiki
Short description: Aromatic organic chemical compound
Cumene hydroperoxide[1]
Names
Preferred IUPAC name
2-Phenylpropane-2-peroxol
Other names
Cumyl hydroperoxide
CHP
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
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 GHS02: Flammable GHS05: Corrosive GHS06: Toxic GHS08: Health hazard GHS09: Environmental hazard
GHS Signal word DANGER
H242, H302, H312, H314, H331, H373, H411
P220, P261, P273, P280, P305+351+338, P310
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondFlammability 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 checkY☒N ?)
Infobox references
Tracking categories (test):

Cumene hydroperoxide is the organic compound with the formula C6H5C(CH3)2OOH; this oily liquid is classified as an organic hydroperoxide.[2] Products of decomposition of cumene hydroperoxide are methylstyrene, acetophenone, and 2-phenylpropan-2-ol.[3]

It is produced by treatment of cumene with oxygen, an autoxidation. At temperatures >100 °C, oxygen is passed through liquid cumene:[4]

C6H5CH(CH3)2 + O2 → C6H5C(CH3)2OOH

Dicumyl peroxide is a side product.

Applications

Cumene hydroperoxide is an intermediate in the cumene process for producing phenol and acetone from benzene and propylene.

Overview of the cumene process

Cumene hydroperoxide is a radical initiator for production of acrylates.[5]

Cumene hydroperoxide is involved as an organic peroxide in the production 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-phenylpropan-2-ol. The reaction follows this stoichiometry:

CH3CHCH2 + C6H5C(CH3)2OOH → CH3CHCH2O + C6H5C(CH3)2OH

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

  1. ↑ University, Safety Officer in Physical Chemistry at Oxford (2005). "Safety (MSDS) data for cumene hydroperoxide". http://msds.chem.ox.ac.uk/CU/cumene_hydroperoxide.html. 
  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. ↑ 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. 
  5. ↑ "Hazardous substance fact sheet: Cumene Hydroperoxide". April 2003. https://www.nj.gov/health/eoh/rtkweb/documents/fs/0543.pdf. 
  6. ↑ "Summary of Sumitomo process from Nexant Reports". http://nexant.ecnext.com/coms2/gi_0255-227/Developments-in-Propylene-Oxide-Technology.html. 
  7. ↑ PubChem. "Cumene hydroperoxide" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/6629. 



Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Cumene_hydroperoxide&oldid=4531791"