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Names | |||
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Preferred IUPAC name
Oxepan-2-one | |||
Other names
Caprolactone
ε-Caprolactone Hexano-6-lactone 6-Hexanolactone Hexan-6-olide 1-Oxa-2-oxocycloheptane | |||
Identifiers | |||
3D model (
JSmol)
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ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard | 100.007.217 | ||
KEGG | |||
PubChem
CID
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UNII | |||
CompTox Dashboard (
EPA)
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Properties | |||
C6H10O2 | |||
Molar mass | 114.14 g/mol | ||
Density | 1.030 g/cm3 | ||
Melting point | −1 °C (30 °F; 272 K) | ||
Boiling point | 241 °C (466 °F; 514 K) [2] | ||
Miscible [1] | |||
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
ε-Caprolactone or simply caprolactone is a lactone (a cyclic ester) possessing a seven-membered ring. Its name is derived from caproic acid. This colorless liquid is miscible with most organic solvents and water. It was once produced on a large scale as a precursor to caprolactam. [3]
Caprolactone is prepared industrially by Baeyer-Villiger oxidation of cyclohexanone with peracetic acid.
Caprolactone is a monomer used in the production of highly specialised polymers. Ring-opening polymerization, for example, gives polycaprolactone. [3] Another polymer is polyglecaprone, used as suture material in surgery. [4]
Although no longer economical, caprolactone was once produced as a precursor to caprolactam. Caprolactone is treated with ammonia at elevated temperatures to give the lactam:
Carbonylation of caprolactone gives, after hydrolysis, pimelic acid. The lactone ring is easily opened with nucleophiles including alcohols and water to give polylactones and eventually the 6-hydroxyadipic acid.
Several other caprolactones are known, including α-, β-, γ-, and δ-caprolactones. All are chiral. (R)-γ-caprolactone is a component of floral scents and of the aromas of some fruits and vegetables, [5] and is also produced by the Khapra beetle as a pheromone. [6] δ-caprolactone is found in heated milk fat. [7]
An ether of caprolactone is used as a binder for AP/ AN/ Al rocket propellant HTCE: Hydroxy-Terminated Caprolactone Ether [8]
Caprolactone hydrolyses rapidly and the resulting hydroxycarboxylic acid displays unexceptional toxicity, as is common for the other hydroxycarboxylic acids. [9] It is known to cause severe eye irritation. Exposure may result in corneal injury. [1]
| |||
Names | |||
---|---|---|---|
Preferred IUPAC name
Oxepan-2-one | |||
Other names
Caprolactone
ε-Caprolactone Hexano-6-lactone 6-Hexanolactone Hexan-6-olide 1-Oxa-2-oxocycloheptane | |||
Identifiers | |||
3D model (
JSmol)
|
|||
ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard | 100.007.217 | ||
KEGG | |||
PubChem
CID
|
|||
UNII | |||
CompTox Dashboard (
EPA)
|
|||
| |||
| |||
Properties | |||
C6H10O2 | |||
Molar mass | 114.14 g/mol | ||
Density | 1.030 g/cm3 | ||
Melting point | −1 °C (30 °F; 272 K) | ||
Boiling point | 241 °C (466 °F; 514 K) [2] | ||
Miscible [1] | |||
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
|
ε-Caprolactone or simply caprolactone is a lactone (a cyclic ester) possessing a seven-membered ring. Its name is derived from caproic acid. This colorless liquid is miscible with most organic solvents and water. It was once produced on a large scale as a precursor to caprolactam. [3]
Caprolactone is prepared industrially by Baeyer-Villiger oxidation of cyclohexanone with peracetic acid.
Caprolactone is a monomer used in the production of highly specialised polymers. Ring-opening polymerization, for example, gives polycaprolactone. [3] Another polymer is polyglecaprone, used as suture material in surgery. [4]
Although no longer economical, caprolactone was once produced as a precursor to caprolactam. Caprolactone is treated with ammonia at elevated temperatures to give the lactam:
Carbonylation of caprolactone gives, after hydrolysis, pimelic acid. The lactone ring is easily opened with nucleophiles including alcohols and water to give polylactones and eventually the 6-hydroxyadipic acid.
Several other caprolactones are known, including α-, β-, γ-, and δ-caprolactones. All are chiral. (R)-γ-caprolactone is a component of floral scents and of the aromas of some fruits and vegetables, [5] and is also produced by the Khapra beetle as a pheromone. [6] δ-caprolactone is found in heated milk fat. [7]
An ether of caprolactone is used as a binder for AP/ AN/ Al rocket propellant HTCE: Hydroxy-Terminated Caprolactone Ether [8]
Caprolactone hydrolyses rapidly and the resulting hydroxycarboxylic acid displays unexceptional toxicity, as is common for the other hydroxycarboxylic acids. [9] It is known to cause severe eye irritation. Exposure may result in corneal injury. [1]