Cumene

Not to be confused with cumin or cumulene.

Cumene

Names
IUPAC name (1-methylethyl)benzene
Systematic IUPAC name prop-2-ylbenzene 2-phenylpropane
Other names i-propylbenzene isopropylbenzene cumol
Identifiers
CAS Number	98-82-8 Y
ChEBI	CHEBI:34656 Y
ChemSpider	7128 Y
Jmol 3D model	Interactive image
KEGG	C14396 Y
PubChem	7406
RTECS number	GR8575000
UNII	8Q54S3XE7K Y
InChI InChI=1S/C9H12/c1-8(2)9-6-4-3-5-7-9/h3-8H,1-2H3 Y Key: RWGFKTVRMDUZSP-UHFFFAOYSA-N Y InChI=1/C9H12/c1-8(2)9-6-4-3-5-7-9/h3-8H,1-2H3 Key: RWGFKTVRMDUZSP-UHFFFAOYAJ
SMILES CC(C)c1ccccc1
Properties
Chemical formula	C9H12
Molar mass	120.20 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
Vapor pressure	8 mm (20°C)
Refractive index (nD)	1.4915 (20 °C)
Viscosity	0.777 cP (21 °C)
Vapor pressure	{{{value}}}
Related compounds
Related compounds	ethylbenzene toluene benzene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
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

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. 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.

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.

Health effects

A review by the US Department of Health and Human Services found that mice exposed to cumene fumes developed tumors in their lungs and livers. Cumene was anticipated to also be a human carcinogen and was added to the governmental organization's list of carcinogens in 2014.

See also

• Cumene process
• Pseudocumene

External links

• National Pollutant Inventory - Cumene fact sheet
• CDC - NIOSH Pocket Guide to Chemical Hazards
• Cumene Production from Benzene and Propylene Using Aluminum Chloride Catalyst