Caprolactone
<templatestyles src="Chembox/styles.css"/>
Template:Chembox AllOtherNamesTemplate:Chembox headerbarTemplate:Chembox IndexlistTemplate:Chembox JmolTemplate:Chembox ChEMBLTemplate:Chembox ECHATemplate:Chembox E numberTemplate:Chembox IUPHAR ligandTemplate:Chembox UNIITemplate:Chembox CompToxTemplate:Chembox headerbarTemplate:Chembox SolubilityInWaterTemplate:Chembox Datapage checkTemplate:Chembox Footer| Template:Chembox image sbs cell | |
| Template:Longitem | Template:Unbulleted list |
| ChEBI | Template:Unbulleted list |
| ChemSpider | Template:Unbulleted list |
| DrugBank | Template:Unbulleted list |
| EC Number | Template:Unbulleted list |
| KEGG | Template:Unbulleted list |
| Template:Longitem | Template:Unbulleted list |
| RTECS number | Template:Unbulleted list |
| Script error: No such module "collapsible list". | |
| Script error: No such module "collapsible list". | |
| Template:Longitem | C6H10O2 |
| Molar mass | 114.14 g/mol |
| Density | 1.030 g/cm3 |
| Melting point | Template:Chembox CalcTemperatures |
| Boiling point | Template:Chembox CalcTemperatures |
Template:Chembox Footer/trackingScript error: No such module "TemplatePar".Template:Short description
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.[2]
Production and uses
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.[2] Another polymer is polyglecaprone, used as suture material in surgery.[3]
Reactions
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:
- (CH2)5CO2 + NH3 → (CH2)5C(O)NH + H2O
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.
Related compounds
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,[4] and is also produced by the Khapra beetle as a pheromone.[5] δ-caprolactone is found in heated milk fat.[6]
An ether of caprolactone is used as a binder for AP/AN/Al rocket propellant HTCE: Hydroxy-Terminated Caprolactone Ether [7]
Safety
Caprolactone hydrolyses rapidly and the resulting hydroxycarboxylic acid displays unexceptional toxicity, as is common for the other hydroxycarboxylic acids.[8] It is known to cause severe eye irritation. Exposure may result in corneal injury.[1]
References
<templatestyles src="Reflist/styles.css" />
- ↑ a b Script error: No such module "citation/CS1".
- ↑ a b Script error: No such module "citation/CS1".
- ↑ Script error: No such module "citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ Script error: No such module "Citation/CS1".
- ↑ HTCE
- ↑ Script error: No such module "citation/CS1".
Script error: No such module "Check for unknown parameters".