Caprolactone
From Wikipedia, the free encyclopedia
| Caprolactone | |
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| Chemical name | 2-oxepanone |
| Other names | ε-caprolactone epsilon-caprolactone 6-hexanolactone |
| Chemical formula | C6H10O2 |
| Molecular mass | 114.14 g/mol |
| CAS number | [502-44-3] |
| Density | 1.030 g/cm3 |
| Melting point | -1 °C |
| Boiling point | 253 °C |
| SMILES | O=C1OCCCCC1 |
| Disclaimer and references | |
Caprolactone is a cyclic ester, known as a lactone, with a ring size of seven. It is a clear colorless liquid that is miscible with most organic solvents except aliphatic hydrocarbons. It reacts slowly with water to form 6-hydroxyhexanoic acid.
Caprolactone is prepared industrially by Baeyer-Villiger oxidation of cyclohexanone with peracetic acid.
The lactone ring is easily opened with nucleophiles including alcohols and water. Caprolactone is a monomer used in the manufacture of various polymers including polycaprolactone. It is also used in synthetic fibers, polyurethane elastomers, plastics, adhesive fabrics, and coatings.
Caprolactone is known to cause severe eye irritation. Exposure may result in corneal injury.
