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Caprolactone

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Caprolactone
Skeletal formula of caprolactone
Ball-and-stick model of the caprolactone molecule
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
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.217 Edit this at Wikidata
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H10O2/c7-6-4-2-1-3-5-8-6/h1-5H2Key: PAPBSGBWRJIAAV-UHFFFAOYSA-N
  • InChI=1/C6H10O2/c7-6-4-2-1-3-5-8-6/h1-5H2Key: PAPBSGBWRJIAAV-UHFFFAOYAG
SMILES
  • C1CCC(=O)OCC1
Properties
Chemical formula C6H10O2
Molar mass 114.14 g/mol
Density 1.030 g/cm
Melting point −1 °C (30 °F; 272 K)
Boiling point 241 °C (466 °F; 514 K)
Solubility in water Miscible
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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.

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. Another polymer is polyglecaprone, used as suture material in surgery.

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, and is also produced by the Khapra beetle as a pheromone. δ-caprolactone is found in heated milk fat.

An ether of caprolactone is used as a binder for AP/AN/Al rocket propellant HTCE: Hydroxy-Terminated Caprolactone Ether

Safety

Caprolactone hydrolyses rapidly and the resulting hydroxycarboxylic acid displays unexceptional toxicity, as is common for the other hydroxycarboxylic acids. It is known to cause severe eye irritation. Exposure may result in corneal injury.

References

  1. ^ "ε-caprolactone SIDS Initial Assessment Report" (PDF). OECD. Archived from the original (PDF) on 2011-08-15. Retrieved 2017-10-12.
  2. "Capa Monomer product data sheet" (PDF). Perstorp. 2015-02-27. Archived from the original (PDF) on 2017-02-02. Retrieved 2017-10-11.
  3. ^ Köpnick, Horst; Schmidt, Manfred; Brügging, Wilhelm; Rüter, Jörn; Kaminsky, Walter (2002). "Polyesters". Ullmann's Encyclopedia of Industrial Chemistry (6th ed.). Weinheim: Wiley-VCH. doi:10.1002/14356007.a21_227.
  4. "glycolide E-caprolactone copolymer Summary Report". CureHunter. Retrieved 2017-10-11.
  5. Mosandl, A.; Günther, C. (1989). "Stereoisomeric flavor compounds: structure and properties of gamma-lactone enantiomers". Journal of Agricultural and Food Chemistry. 37: 413–418. doi:10.1021/jf00086a031.
  6. Nunez, M. Teresa; Martin, Victor S. (1990). "Efficient oxidation of phenyl groups to carboxylic acids with ruthenium tetraoxide. A simple synthesis of (R)-gamma-caprolactone, the pheromone of Trogoderma granarium". Journal of Organic Chemistry. 55 (6): 1928–1932. doi:10.1021/jo00293a044.
  7. Parliament, Thomas H.; Nawar, Wassef W.; Fagerson, Irving S. (1965). "Delta-Caprolactone in Heated Milk Fat". Journal of Dairy Science. 48 (5): 615–616. doi:10.3168/jds.S0022-0302(65)88298-4.
  8. HTCE
  9. Miltenberger, Karlheinz (2002). "Hydroxycarboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry (6th ed.). Weinheim: Wiley-VCH. doi:10.1002/14356007.a13_507.
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