Cumene

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Not to be confused with cumin or cumulene.
Cumene
Skeletal formula of cumene Ball-and-stick model of cumene
Identifiers
CAS number 98-82-8 YesY
PubChem 7406
ChemSpider 7128 YesY
UNII 8Q54S3XE7K YesY
KEGG C14396 YesY
ChEBI CHEBI:34656 YesY
RTECS number GR8575000
Jmol-3D images Image 1
Properties
Molecular formula C9H12
Molar mass 120.19 g mol−1
Appearance colorless liquid
Odor sharp, gasoline-like
Density 0.862 g cm−3, liquid
Melting point −96 °C (−141 °F; 177 K)
Boiling point 152 °C (306 °F; 425 K)
Solubility in water negligible
Solubility soluble in acetone, ether, ethanol
Refractive index (nD) 1.4915 (20 °C)
Viscosity 0.777 cP (21 °C)
Hazards
R-phrases R10,R37,R51/53,R65
S-phrases S24,S37,S61,S62
Main hazards flammable
NFPA 704
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g., gasoline) Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g., calcium Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 43 °C (109 °F; 316 K)
Explosive limits 0.9-6.5%
Related compounds
Related compounds ethylbenzene
toluene
benzene
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Cumene is the common name for isopropylbenzene, an organic compound that is based on an aromatic hydrocarbon with an aliphatic substitution. It is a constituent of crude oil and refined fuels. It is a flammable colorless liquid that has a boiling point of 152 °C. Nearly all the cumene that is produced as a pure compound on an industrial scale is converted to cumene hydroperoxide, which is an intermediate in the synthesis of other industrially important chemicals, primarily phenol and acetone.

Production[edit]

Cumene-formation-2D-skeletal.png

Commercial production of cumene is by Friedel–Crafts alkylation of benzene with propylene. Cumene producers account for approximately 20% of the global demand for benzene.[1] Previously, solid phosphoric acid (SPA) supported on alumina was used as the catalyst. Since the mid-1990s, commercial production has switched to zeolite-based catalysts.[2]

Isopropylbenzene is stable, but may form peroxides in storage if in contact with the air. It is important to test for the presence of peroxides before heating or distilling. The chemical is also flammable and incompatible with strong oxidizing agents. Environmental laboratories commonly test isopropylbenzene using a Gas chromatography–mass spectrometry (GCMS) instrument.[3]

See also[edit]

References[edit]

  1. ^ Market Study Benzene, published by Ceresana, July 2011 [1]
  2. ^ The Innovation Group website, page accessed 15/11/07
  3. ^ http://www.caslab.com/Isopropylbenzene.php5

External links[edit]