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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.005.462
UNII
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).
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]

Properties and reactions

Cyclohexene has been studied extensively by analytical methods.[9] Cyclohexene oxide can be polymerized in solution, catalyzed by a solid acid catalyst.[10]

Application

One of the known uses is in the synthesis of bromadoline.

References
  1. Record of Epoxycyclohexane in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 1 February 2014.
  2. M. Quenard; V. Bonmarin; G. Gelbard (1987). "Epoxidation of olefins by hydrogen peroxide catalyzed by phosphonotungstic complexes". Tetrahedron Letters. 28 (20): 2237–2238. doi:10.1016/S0040-4039(00)96089-1.
  3. Ha Q. Pham; Maurice J. Marks (2005), "Epoxy Resins", Ullmann's Encyclopedia of Industrial Chemistry (in German), doi:10.1002/14356007.a09_547.pub2, ISBN 3527306730
  4. Siegfried Rebsdat; Dieter Mayer (2001), "Ethylene Oxide", Ullmann's Encyclopedia of Industrial Chemistry (in German), doi:10.1002/14356007.a10_117, ISBN 3527306730
  5. "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.
  6. Ambili, V K; Dr.Sugunan, S, Faculty of Sciences (ed.), Studies on Catalysis by Ordered Mesoporous SBA-15 Materials Modified with Transition Metals (in German), retrieved 2014-07-27CS1 maint: multiple names: authors list (link)
  7. 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.
  8. 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.
  9. RM Ibberson; O. Yamamuro; I. Tsukushi (2006). "The crystal structures and phase behaviour of cyclohexene oxide". Chemical Physics Letters. 423 (4–6): 454–458. Bibcode:2006CPL...423..454I. doi:10.1016/j.cplett.2006.04.004.
  10. 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.
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