Chemistry:Cyclohexene oxide

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Cyclohexene oxide
Cyclohexeenoxide.png
Names
IUPAC name
7-Oxabicyclo[4.1.0]heptane
Other names
Epoxycyclohexane
Identifiers
3D model (JSmol)
ChemSpider
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
Tracking categories (test):

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]

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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]

Synthesis of cyclohexene oxide

With this method, good yields up to 85 % can be reached.

Properties and reactions

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

References

  1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 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" (in de), Ullmann's Encyclopedia of Industrial Chemistry, doi:10.1002/14356007.a09_547.pub2, ISBN 3527306730 
  4. ↑ Siegfried Rebsdat; Dieter Mayer (2001), "Ethylene Oxide" (in de), Ullmann's Encyclopedia of Industrial Chemistry, doi:10.1002/14356007.a10_117, ISBN 3527306730 
  5. ↑ Morazzoni, Franca; Canevali, Carmen; d'Aprile, Fiorenza; Bianchi, Claudia L.; Tempesti, Ezio; Giuffrè, Luigi; Airoldi, Giuseppe (1995). "Spectroscopic investigation of the molybdenum active sites on MoVI heterogeneous catalysts for alkene epoxidation". Journal of the Chemical Society, Faraday Transactions 91 (21): 3969–3974. doi:10.1039/FT9959103969. 
  6. ↑ Ambili, V K; Dr.Sugunan, S (April 2011) (in de), Studies on Catalysis by Ordered Mesoporous SBA-15 Materials Modified with Transition Metals, Cochin University of Science and Technology, http://dyuthi.cusat.ac.in/purl/2787, retrieved 2014-07-27 
  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. ↑ Brougham, Paul; Cooper, Mark S.; Cummerson, David A.; Heaney, Harry; Thompson, Nicola (1987). "Oxidation Reactions Using Magnesium Monoperphthalate: A Comparison with m-Chloroperoxybenzoic Acid". Synthesis 1987 (11): 1015–1017. doi:10.1055/s-1987-28153. https://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-1987-28153. Retrieved 2020-07-31. 
  10. ↑ 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. Bibcode: 2006CPL...423..454I. 
  11. ↑ 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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