Cyclohexene oxide
 | |
| Names | |
|---|---|
| IUPAC name
7-Oxabicyclo[4.1.0]heptane | |
| Other names
Epoxycyclohexane | |
| Identifiers | |
| 286-20-4 | |
| 3D model (Jmol) | Interactive image |
| ECHA InfoCard | 100.005.462 |
| PubChem | 9246 |
| |
| |
| Properties | |
| C6H10O | |
| Molar mass | 98.15 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). | |
| 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.
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 the (consumed) 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]
Chemical analysis
Cyclohexene has been studied extensively by analytical methods. A good overview is given in literature.[9] 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.[10]
References
- 1 2 3 4 5 6 Record of Epoxycyclohexane in the GESTIS Substance Database of the IFA, accessed on 1 February 2014.
- ↑ M. Quenard; V. Bonmarin; G. Gelbard. "Epoxidation of olefins by hydrogen peroxide catalyzed by phosphonotungstic complexes". doi:10.1016/S0040-4039(00)96089-1.
- ↑ Ha Q. Pham; Maurice J. Marks (in German), Epoxy Resins, doi:10.1002/14356007.a09_547.pub2
- ↑ Siegfried Rebsdat; Dieter Mayer (in German), Ethylene Oxide, doi:10.1002/14356007.a10_117
- ↑ "Spectroscopic investigation of the molybdenum active sites on MoVI heterogeneous catalysts for alkene epoxidation". Journal of the Chemical Society, Faraday Transactions. 1995. doi:10.1039/FT9959103969.
- ↑ Ambili, V K; Dr.Sugunan, S, Faculty of Sciences, ed. (in German), Studies on Catalysis by Ordered Mesoporous SBA-15 Materials Modified with Transition Metals
- ↑ Costa, Andréia A. Ghesti; Grace F. de Macedo; Julio L. Braga; Valdeilson S. Santos; Marcello M. Dias; José A. Dias; Sílvia C.L. (2008). "Immobilization of Fe, Mn and Co tetraphenylporphyrin complexes in MCM-41 and their catalytic activity in cyclohexene oxidation reaction by hydrogen peroxide". Journal of Molecular Catalysis A: Chemical. 282 (1–2): 149–157. doi:10.1016/j.molcata.2007.12.024.
- ↑ Xian-Tai Zhou; Hong-Bing Ji; Jian-Chang Xu; Li-Xia Pei; Le-Fu Wang; Xing-Dong Yao (2007). "Enzymatic-like mediated olefins epoxidation by molecular oxygen under mild conditions". Tetrahedron Letters. 48 (15): 2691–2695. doi:10.1016/j.tetlet.2007.02.066.
- ↑ RM Ibberson; O. Yamamuro; I. Tsukushi (2006). "The crystal structures and phase behaviour of cyclohexene oxide". Chemical physics letters. 423 (4–6): 454–458. doi:10.1016/j.cplett.2006.04.004.
- ↑ Ahmed Yahiaoui; Mohammed Belbachir; Jeanne Claude Soutif; Laurent Fontaine (2005). "Synthesis and structural analyses of poly(1,2-cyclohexene oxide) over solid acid catalyst". Materials Letters. 59 (7): 759–767. doi:10.1016/j.matlet.2004.11.017.