Cyclohexene oxide
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| Names | |
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| IUPAC name
7-Oxabicyclo[4.1.0]heptane
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| Other names
Epoxycyclohexane
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C6H10O | |
| Molar mass | 98.145 g·mol−1 |
| Appearance | Colorless liquid[1] |
| Density | 0.97 g·cm−3[1] |
| Melting point | ca. −40 °C[1] |
| Boiling point | ca. 130 °C[1] |
| Practically insoluble[1] | |
| Vapor pressure | 12 mbar (at 20 °C)[1] |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Cyclohexene oxide is a cycloaliphatic epoxide. It can react in cationic polymerization to poly(cyclohexene oxide). As cyclohexene is monovalent, poly(cyclohexene oxide) is a thermoplastic.
Production
[edit | edit source]Cyclohexene oxide is produced in epoxidation reaction from cyclohexene. The epoxidation can take place either in a homogeneous reaction by peracids[2] or heterogeneous catalysis (e.g. silver and molecular oxygen).[3][4][5]
In industrial production the heterogeneously catalyzed synthesis is preferred because of better atom economy, a simpler separation of the product and easier recycling of catalyst. A short overview and an investigation of the oxidation of cyclohexene by hydrogen peroxide is given in the literature.[6] In recent times the catalytic oxidation of cyclohexene by (immobilized) metalloporphyrin complexes has been found to be an efficient way.[7][8]
In laboratory, cyclohexene oxide can also be prepared by reacting cyclohexene with magnesium monoperoxyphthalate (MMPP) in a mixture of isopropanol and water as solvent at room temperature.[9]
With this method, good yields up to 85 % can be reached.
Properties and reactions
[edit | edit source]Cyclohexene oxide has been studied extensively by analytical methods.[10] Cyclohexene oxide can be polymerized in solution, catalyzed by a solid acid catalyst.[11]
References
[edit | edit source]- ^ a b c d e f Record of Epoxycyclohexane in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 1 February 2014.
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