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Caprolactone

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Caprolactone
Names
IUPAC name 2-oxepanone
Other names epsilon-caprolactone
6-hexanolactone
hexano-6-lactone
1-oxa-2-oxocycloheptane
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.217 Edit this at Wikidata
KEGG
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
Boiling point 253 °C
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 cyclic ester, a member of the lactone family, with a seven-membered ring with the formula (CH2)5CO2. This colorless liquid is miscible with most organic solvents. It is produced on a very large scale as a precursor to caprolactam.

Production and uses

The great majority of caprolactone is consumed, often in situ, as a precursor to caprolactam. It is also a monomer used in the manufacture of highly specialised polymers. Ring-opening polymerization, for example, gives polycaprolactone. Another polymer is polyglecaprone, used as suture material in surgery.

Caprolactone is prepared industrially by Baeyer-Villiger oxidation of cyclohexanone with peracetic acid. The three main manufacturers are BASF in the USA, Daicel in Japan and the largest Perstorp in the UK.

Reactions

The dominant reaction for caprolactone is its conversion to caprolactam, billions of kilograms of which are produced annually. 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, although none approaches the technological importance of ε-caprolactone. These isomers include alpha-, beta-, gamma-, delta-caprolactones. All are chiral. Gamma-caprolactone is component of flower aromas and an insect pheromone. delta-Caprolactone is found in heated milk fat.

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. OECD SIDS
  2. Josef Ritz, Hugo Fuchs, Heinz Kieczka, William C. Moran "Caprolactam" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a05_031
  3. Horst Köpnick, Manfred Schmidt, Wilhelm Brügging, Jörn Rüter, Walter Kaminsky "Polyesters" in Ullmann's Encyclopedia of Industrial Chemistry 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a21_227
  4. http://www.curehunter.com/public/keywordSummaryC095495-glycolide-E-caprolactone-copolymer.do
  5. Leading reference: M. Teresa Nunez, Victor S. Martin (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, 1990, Volume 55, Issue 6, pp 1928–1932. doi:10.1021/jo00293a044
  6. Thomas H. Parliament, Wassef W. Nawar and Irving S. Fagerson (1965), Delta-Caprolactone in Heated Milk Fat Journal of Dairy Science Vol. 48 No. 5 pages 615-616.
  7. Karlheinz Miltenberger "Hydroxycarboxylic Acids, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. doi:10.1002/14356007.a13_507
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