Cyclohexene oxide
 | |
| Names | |
|---|---|
| IUPAC name
7-Oxabicyclo[4.1.0]heptane | |
| Other names
Epoxycyclohexane | |
| Identifiers | |
| 286-20-4 | |
| Jmol interactive 3D | Image |
| 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, http://dyuthi.cusat.ac.in/purl/2787. Retrieved 2014-07-27
- ↑ 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.