Loading AI tools
Chemical compound From Wikipedia, the free encyclopedia
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.
Names | |
---|---|
IUPAC name
7-Oxabicyclo[4.1.0]heptane | |
Other names
Epoxycyclohexane | |
Identifiers | |
3D model (JSmol) |
|
ChemSpider | |
ECHA InfoCard | 100.005.462 |
PubChem CID |
|
UNII | |
CompTox Dashboard (EPA) |
|
| |
| |
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).
|
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.
Cyclohexene oxide has been studied extensively by analytical methods.[10] Cyclohexene oxide can be polymerized in solution, catalyzed by a solid acid catalyst.[11]
Seamless Wikipedia browsing. On steroids.
Every time you click a link to Wikipedia, Wiktionary or Wikiquote in your browser's search results, it will show the modern Wikiwand interface.
Wikiwand extension is a five stars, simple, with minimum permission required to keep your browsing private, safe and transparent.