Saturday, April 9, 2011

e-caprolactone

ε-Caprolactone (epsilon-caprolactone) is a cyclic ester, a member of the lactone family, with a seven-membered ring with the formula (CH2)5CO2 and IUPAC name of 2-oxepanone. It is a colorless, miscible liquid with most organic solvents and it is produced on a very large scale as a precursor to caprolactam
The physical properties of caprolactone are as follows:
- molecular weight: 114.14g/mole
- melting pt.: -1*C
- boiling pt.: 253*C
- density: 1.030g/cm^3
- solubility: > 1000mg/L (20*C)

Caprolactone is often used as a precursor to caprolactam. It is also a monomer used in the manufacture of highly specialized polymers. An example of a polymer is polyglecaprone, used as suture material in surgery. Caprolactone is prepared industrially by Baeyer-Villiger oxidation of cyclohexanone with peracetic acid.

The dominant reaction of caprolactone which is the conversion to caprolactam, involves treatment with hydroxylamine followed by sulfuric acid to give the desired lactam as shown below in a multi-step synthesis.

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