Cumene

Not to be confused with cumin or cumulene.

Cumene
IUPAC name (1-methylethyl)benzene
Other names isopropylbenzene 2-phenylpropane
Identifiers
CAS number	98-82-8 Y
PubChem	7406
ChemSpider	7128 Y
UNII	8Q54S3XE7K Y
KEGG	C14396 Y
ChEBI	CHEBI:34656 Y
RTECS number	GR8575000
Jmol-3D images	Image 1
SMILES CC(C)c1ccccc1
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
Properties
Molecular formula	C9H12
Molar mass	120.19 g mol−1
Appearance	colorless liquid
Density	0.862 g cm−3, liquid
Melting point	−96 °C, 177 K, -141 °F
Boiling point	152 °C, 425 K, 306 °F
Solubility in water	insoluble
Viscosity	0.777 cP at 21 °C
Hazards
R-phrases	R10,R37,R51/53,R65
S-phrases	S24,S37,S61,S62
Main hazards	flammable
Flash point	43 °C
Related compounds
Related compounds	ethylbenzene toluene benzene
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Cumene is the common name for isopropylbenzene, an organic compound that is an aromatic hydrocarbon. 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. 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.

See also

• Cumene process

External links

• National Pollutant Inventory - Cumene fact sheet