Cyclohexene oxide

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

Names
IUPAC name 7-Oxabicyclo[4.1.0]heptane
Other names Epoxycyclohexane
Identifiers
CAS Number	286-20-4 Y
3D model (JSmol)	Interactive image
ChemSpider	8890
ECHA InfoCard	100.005.462
PubChem CID	9246
UNII	1XYE04C550 Y
CompTox Dashboard (EPA)	DTXSID6024880
InChI InChI=1S/C6H10O/c1-2-4-6-5(3-1)7-6/h5-6H,1-4H2 Key: ZWAJLVLEBYIOTI-UHFFFAOYSA-N
SMILES C1CCC2C(C1)O2
Properties
Chemical formula	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]
Solubility in water	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). Infobox references

Production

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

Cyclohexene oxide has been studied extensively by analytical methods.^[10] Cyclohexene oxide can be polymerized in solution, catalyzed by a solid acid catalyst.^[11]