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Revision as of 12:09, 7 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (changes to verified and watched fields - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report errors← Previous edit Latest revision as of 00:11, 21 February 2024 edit undoAlhadis (talk | contribs)Extended confirmed users1,094 editsm PNG -> SVG 
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| Verifiedfields = changed | Verifiedfields = changed
| Watchedfields = changed | Watchedfields = changed
| verifiedrevid = 407465310 | verifiedrevid = 443497647
| Name = Caprolactone | Name = Caprolactone
| ImageFile = Caprolactone.png | ImageFileL1 = Caprolactone.svg
| ImageSize = 100px | ImageSizeL1 = 100px
| ImageAltL1 = Skeletal formula of caprolactone
| ImageName =
| ImageFileR1 = Caprolactone-from-xtal-2007-3D-balls.png
| IUPACName = 2-oxepanone
| ImageSizeR1 = 150
| OtherNames = epsilon-caprolactone<br />6-hexanolactone<br />hexano-6-lactone<br />1-oxa-2-oxocycloheptane
| ImageAltR1 = Ball-and-stick model of the caprolactone molecule
⚫ | Section1 = {{Chembox Identifiers
| PIN= Oxepan-2-one
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| OtherNames = Caprolactone<br />ε-Caprolactone<br />Hexano-6-lactone<br />6-Hexanolactone<br />Hexan-6-olide<br />1-Oxa-2-oxocycloheptane
⚫ |Section1={{Chembox Identifiers
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 9972 | ChemSpiderID = 9972
| PubChem = 10401
| KEGG_Ref = {{keggcite|changed|kegg}} | KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C01880 | KEGG = C01880
| InChI = 1/C6H10O2/c7-6-4-2-1-3-5-8-6/h1-5H2 | InChI = 1/C6H10O2/c7-6-4-2-1-3-5-8-6/h1-5H2
Line 24: Line 28:
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 502-44-3 | CASNo = 502-44-3
| ChEBI_Ref = {{ebicite|changed|EBI}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 56RE988L1R
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 17915 | ChEBI = 17915
| SMILES = C1CCC(=O)OCC1 | SMILES = C1CCC(=O)OCC1
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>6</sub>H<sub>10</sub>O<sub>2</sub> | Formula = C<sub>6</sub>H<sub>10</sub>O<sub>2</sub>
| MolarMass = 114.14 g/mol | MolarMass = 114.14 g/mol
| Density = 1.030 g/cm<sup>3</sup> | Density = 1.030 g/cm<sup>3</sup>
| Solubility = Miscible <ref name="OECD">{{cite web|title=ε-caprolactone SIDS Initial Assessment Report|publisher=OECD|url=http://www.chem.unep.ch/irptc/sids/OECDSIDS/502443.pdf|archive-url=https://web.archive.org/web/20110815130105/http://www.chem.unep.ch/irptc/sids/OECDSIDS/502443.pdf#|archive-date=2011-08-15|access-date=2017-10-12|url-status=dead}}</ref>
| MeltingPt = -1 °C
| MeltingPtC = -1
| BoilingPt = 253 °C <ref> OECD SIDS </ref>
| BoilingPtC = 241
| BoilingPt_ref = <ref>{{cite web|url=https://www.perstorp.com/-/media/files/perstorp/pds/capa%20monomer/pds_capa%20monomer_eng-6142.pdf|title=Capa Monomer product data sheet|publisher=Perstorp|date=2015-02-27|access-date=2017-10-11|archive-url=https://web.archive.org/web/20170202061130/https://www.perstorp.com/-/media/files/perstorp/pds/capa%20monomer/pds_capa%20monomer_eng-6142.pdf|archive-date=2017-02-02|url-status=dead}}</ref>
}} }}
}} }}
'''ε-Caprolactone''' or simply '''caprolactone''' is a cyclic ], a member of the ] family, with a seven-membered ring with the formula (CH<sub>2</sub>)<sub>5</sub>CO<sub>2</sub>. This colorless liquid is miscible with most organic solvents. It is produced on a very large scale as a precursor to ]. '''ε-Caprolactone''' or simply '''caprolactone''' is a ] (a cyclic ]) possessing a seven-membered ring. Its name is derived from ]. This colorless liquid is miscible with most organic solvents and water. It was once produced on a large scale as a precursor to ].<ref name="UllmannPolyesters"/>


==Production and uses== ==Production and uses==
⚫ Caprolactone is prepared industrially by ] of ] with ].
⚫ The great majority of caprolactone is consumed, often in situ, as a precursor to caprolactam.<ref>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}}</ref> It is also a monomer used in the manufacture of highly specialised ]s. ], for example, gives ].<ref>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}}</ref> Another polymer is ], used as suture material in surgery.<ref>http://www.curehunter.com/public/keywordSummaryC095495-glycolide-E-caprolactone-copolymer.do</ref>


⚫ Caprolactone is a monomer used in the production of highly specialised ]s. ], for example, gives ].<ref name="UllmannPolyesters">{{cite encyclopedia|last1=Köpnick|first1=Horst|last2=Schmidt|first2=Manfred|last3=Brügging|first3=Wilhelm|last4=Rüter|first4=Jörn|last5=Kaminsky|first5=Walter|title=Polyesters|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|edition=6th|date=2002|publisher=Wiley-VCH|location=Weinheim|doi=10.1002/14356007.a21_227}}</ref> Another polymer is ], used as suture material in surgery.<ref>{{cite web|url=http://www.curehunter.com/public/keywordSummaryC095495-glycolide-E-caprolactone-copolymer.do|title=glycolide E-caprolactone copolymer Summary Report|publisher=CureHunter|access-date=2017-10-11}}</ref>
⚫ Caprolactone is prepared industrially by ] of ] with ]. The three main manufacturers are BASF in the USA, Daicel in Japan and the largest Perstorp in the UK.


==Reactions== ==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: 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:
:(CH<sub>2</sub>)<sub>5</sub>CO<sub>2</sub> + NH<sub>3</sub> → (CH<sub>2</sub>)<sub>5</sub>C(O)NH + H<sub>2</sub>O :(CH<sub>2</sub>)<sub>5</sub>CO<sub>2</sub> + NH<sub>3</sub> → (CH<sub>2</sub>)<sub>5</sub>C(O)NH + H<sub>2</sub>O


] of caprolactone gives, after hydrolysis, ]. The lactone ring is easily opened with nucleophiles including alcohols and water to give polylactones and eventually the 6-hydroxyadipic acid. ] of caprolactone gives, after hydrolysis, ]. The lactone ring is easily opened with nucleophiles including alcohols and water to give polylactones and eventually the 6-hydroxyadipic acid.


==Related compounds== ==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 ] aromas and an ] ].<ref>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}}</ref> delta-Caprolactone is found in heated milk fat.<ref>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.</ref> Several other caprolactones are known, including α-, β-, γ-, and δ-caprolactones. All are chiral. (''R'')-γ-caprolactone is a component of ]s and of the aromas of some fruits and vegetables,<ref>{{cite journal|last1=Mosandl|first1=A.|last2=Günther|first2=C.|title=Stereoisomeric flavor compounds: structure and properties of gamma-lactone enantiomers|journal=Journal of Agricultural and Food Chemistry|volume=37|pages=413–418|date=1989|doi=10.1021/jf00086a031}}</ref> and is also produced by the ] as a ].<ref>{{cite journal|last1=Nunez|first1=M. Teresa|last2=Martin|first2=Victor S.|date=1990|title=Efficient oxidation of phenyl groups to carboxylic acids with ruthenium tetraoxide. A simple synthesis of (R)-gamma-caprolactone, the pheromone of ''Trogoderma granarium''|journal=Journal of Organic Chemistry|volume=55|issue=6|pages=1928–1932|doi=10.1021/jo00293a044}}</ref> δ-caprolactone is found in heated milk fat.<ref>{{cite journal|last1=Parliament|first1=Thomas H.|last2=Nawar|first2=Wassef W.|last3=Fagerson|first3=Irving S.|date=1965|title=Delta-Caprolactone in Heated Milk Fat|journal=Journal of Dairy Science|volume=48|number=5|pages=615–616|doi=10.3168/jds.S0022-0302(65)88298-4|doi-access=free}}</ref>

An ether of caprolactone is used as a binder for ]/]/] rocket propellant HTCE: Hydroxy-Terminated Caprolactone Ether <ref> </ref>


==Safety== ==Safety==
Caprolactone hydrolyses rapidly and the resulting hydroxycarboxylic acid displays unexceptional toxicity, as is common for the other hydroxycarboxylic acids.<ref name=Ullmann>Karlheinz Miltenberger "Hydroxycarboxylic Acids, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. {{DOI|10.1002/14356007.a13_507}}</ref> It is known to cause severe eye irritation. Exposure may result in corneal injury. Caprolactone hydrolyses rapidly and the resulting hydroxycarboxylic acid displays unexceptional toxicity, as is common for the other hydroxycarboxylic acids.<ref name="UllmannHCAAliph">
{{cite encyclopedia|last=Miltenberger|first=Karlheinz|title=Hydroxycarboxylic Acids, Aliphatic|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|edition=6th|date=2002|publisher=Wiley-VCH|location=Weinheim|doi=10.1002/14356007.a13_507}}</ref> It is known to cause severe eye irritation. Exposure may result in corneal injury.<ref name="OECD" />


== References == == References ==
{{reflist}} {{reflist}}


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