Cyclohexene oxide
 |
|
| Names | |
|---|---|
|
IUPAC name
7-Oxabicyclo[4.1.0]heptane
|
|
| Other names
Epoxycyclohexane
|
|
| Identifiers | |
|
3D model (JSmol)
|
|
| ChemSpider | |
| ECHA InfoCard | 100.005.462 |
|
PubChem CID
|
|
|
|
|
|
| Properties | |
| C6H10O | |
| Molar mass | 98.15 g·mol−1 |
| Appearance | Colorless liquid |
| Density | 0.97 g·cm−3 |
| Melting point | ca. -40 °C |
| Boiling point | ca. 130 °C |
| Practically insoluble | |
| Vapor pressure | 12 mbar (at 20 °C) |
|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
|
| Infobox references | |
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.
Cyclohexene oxide is produced in epoxidation reaction from cyclohexene. The epoxidation can take place either in a homogeneous reaction by peracids or heterogeneous catalysis (e.g. silver and molecular oxygen).
In industrial production the heterogeneously catalyzed synthesis is preferred because of better atom economy, a simpler separation of the product and easier recycling of the (consumed) catalyst. A short overview and an investigation of the oxidation of cyclohexene by hydrogen peroxide is given in the literature. In recent times the catalytic oxidation of cyclohexene by (immobilized) metalloporphyrin complexes has been found to be an efficient way.
Cyclohexene has been studied extensively by analytical methods. A good overview is given in literature. A study on the polymerization of cyclohexene oxide in solution catalyzed by a solid acid catalyst and the IR, 1H-NMR and MALDI-TOF spectra of the product together with the SEC chromatograms can be found in literature.
One of the known uses is in the synthesis of bromadoline.
...
Wikipedia