- Caprolactone
Chembox new
Name = Caprolactone
ImageFile = Caprolactone.png
ImageSize = 100px
ImageName =
IUPACName = 2-oxepanone
OtherNames = ε-caprolactone
epsilon-caprolactone
6-hexanolactone
Section1 = Chembox Identifiers
CASNo = 502-44-3
SMILES = O=C1OCCCCC1
Section2 = Chembox Properties
Formula = C6H10O2
MolarMass = 114.14 g/mol
Density = 1.030 g/cm3
MeltingPt = -1 °C
BoilingPt = 253 °CCaprolactone is a cyclic
ester , known as alactone , 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 ofcyclohexanone withperacetic acid .The lactone ring is easily opened with nucleophiles including alcohols and water. Caprolactone is a monomer used in the manufacture of various
polymer s includingpolycaprolactone . It is also used in synthetic fibers, polyurethane elastomers, plastics, adhesive fabrics, and coatings.There 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
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