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Caprolactone



Caprolactone
IUPAC name 2-oxepanone
Other names ε-caprolactone
epsilon-caprolactone
6-hexanolactone
Identifiers
CAS number 502-44-3
SMILES O=C1OCCCCC1
Properties
Molecular formula C6H10O2
Molar mass 114.14 g/mol
Density 1.030 g/cm3
Melting point

-1 °C

Boiling point

253 °C

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox 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.

Additional recommended knowledge

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.

The are three manufacturers in the world, BASF in the USA, Daicel in Japan and the largest Solvay in the UK. Solvay announced in October 2007 that its production unit has been acquired by Perstorp AB of Sweden.

Caprolactone is known to cause severe eye irritation. Exposure may result in corneal injury.

References

     
    This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Caprolactone". A list of authors is available in Wikipedia.
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