cyclohexanol

Also known as Anol, Cyclohexyl alcohol, Hexahydrophenol, Hexalin, Hydralin, Hydroxycyclohexane, Hydrophenol, 1-Cyclohexanol

Cyclohexanol is the organic compound with the formula HOCH(CH2)5 or C6H11OH. The molecule is related to cyclohexane by replacement of one hydrogen atom by a hydroxyl group. This compound exists as a deliquescent colorless solid with a camphor-like odor, which, when very pure, melts near room temperature. Millions of tonnes are produced annually, mainly as a precursor to nylon.

Chemical data

Formula: C6H12O
Molecular weight: 100.16 g/mol
IUPAC name: cyclohexanol
SMILES: C1CCC(CC1)O
InChIKey: HPXRVTGHNJAIIH-UHFFFAOYSA-N
XLogP: 1.2
Polar surface area: 20.2 Å²
H-bond donors: 1
H-bond acceptors: 1
Formal charge: 0

via PubChem

Wikidata facts

Mass: 100.089

Show 13 more facts

Commons category: Cyclohexanol
boiling point: 322
canonical SMILES: C1CCC(CC1)O
vapor pressure: 1
NIOSH Pocket Guide ID: 0165
density: 0.96
immediately dangerous to life or health: 1640
melting point: 25.46
flash point: 154
solubility: 4
ionization energy: 9.75
time-weighted average exposure limit: 200
chemical formula: C₆H₁₂O

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Article

6 sections

Contents

Production
Basic reactions
Structure
Applications
Safety
References

==Production== Cyclohexanol is produced by the oxidation of cyclohexane in air, typically using cobalt catalysts: 2 C6H12 + O2 → 2 C6H11OH This process coforms cyclohexanone, and this mixture ("KA oil" for ketone-alcohol oil) is the main feedstock for the production of adipic acid. The oxidation involves radicals and the intermediacy of the hydroperoxide C6H11O2H. Alternatively, cyclohexanol can be produced by the hydrogenation of phenol: C6H5OH + 3 H2 → C6H11OH This process can also be adjusted to favor the formation of cyclohexanone.