Structure via PubChem · Public domain (PubChem)
cumene
Sign in to saveAlso known as Cumol, Isopropyl benzene, 2-Phenyl propane, (1-Methylethyl)benzene, Polyphenyl residue, Isopropylbenzene [UN1918] [Flammable liquid], 1-Methylethyl-Benzene, Isopropylbenzol
Cumene (isopropylbenzene) is an organic compound that contains a benzene ring with an isopropyl substituent. 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 (known as the cumene process).
Chemical data
- Formula
- C9H12
- Molecular weight
- 120.19 g/mol
- IUPAC name
- cumene
- SMILES
- CC(C)C1=CC=CC=C1
- InChIKey
- RWGFKTVRMDUZSP-UHFFFAOYSA-N
- XLogP
- 3.7
- Polar surface area
- 0 Ų
- H-bond donors
- 0
- H-bond acceptors
- 0
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 120.094
- Autonomy
- 420
Show 16 more facts
- NIOSH Pocket Guide ID
- 0159
- Commons category
- Cumene
- canonical SMILES
- CC(C)C1=CC=CC=C1
- density
- 0.864
- immediately dangerous to life or health
- 4428
- melting point
- -96.01
- boiling point
- 152.41
- vapor pressure
- 5.3
- flash point
- 31
- lower flammable limit
- 0.9
- upper flammable limit
- 6.5
- ionization energy
- 8.73
- time-weighted average exposure limit
- 245
- chemical formula
- C₉H₁₂
- median lethal dose (LD50)
- 1400
- electric dipole moment
- 0.79
via Wikidata · CC0
~3 min read
Article
6 sectionsContents
- Production
- Autoxidation
- Applications
- See also
- References
- External links
Cumene (isopropylbenzene) is an organic compound that contains a benzene ring with an isopropyl substituent. 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 (known as the cumene process).
==Production== Commercial production of cumene is by Friedel–Crafts alkylation of benzene with propylene. The original route for manufacturing of cumene was by alkylation of benzene in the liquid phase using sulfuric acid as a catalyst, but because of the complicated neutralization and recycling steps required, together with corrosion problems, this process has been largely replaced. As an alternative, solid phosphoric acid (SPA) supported on alumina has been used as the catalyst.