Cyclohexene oxide
{{Chembox
| ImageFile = File:Cyclohexeenoxide.png
| ImageSize = 180px
| ImageAlt =
| IUPACName = 7-Oxabicyclo[4.1.0]heptane
| OtherNames = Epoxycyclohexane
| Section1 = {{Chembox Identifiers
| CASNo = 286-20-4
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 1XYE04C550
| PubChem = 9246
| SMILES = C1CCC2C(C1)O2
| ChemSpiderID = 8890
| StdInChI = 1S/C6H10O/c1-2-4-6-5(3-1)7-6/h5-6H,1-4H2
| StdInChIKey = ZWAJLVLEBYIOTI-UHFFFAOYSA-N
}}
| Section2 = {{Chembox Properties
| C=6|H=10|O=1
| Appearance = Colorless liquid{{GESTIS|ZVG=39760|CAS=67-56-1|Name=Epoxycyclohexane |Date=1 February 2014}}
| VaporPressure = 12 mbar (at 20 °C)
| Solubility = Practically insoluble
}}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}
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{{cite journal |author1=M. Quenard |author2=V. Bonmarin |author3=G. Gelbard | year = 1987| title = Epoxidation of olefins by hydrogen peroxide catalyzed by phosphonotungstic complexes | journal = Tetrahedron Letters| volume = 28| issue = 20| pages = 2237–2238| doi =10.1016/S0040-4039(00)96089-1}} or heterogeneous catalysis (e.g. silver and molecular oxygen).{{citation|surname1=Ha Q. Pham|surname2=Maurice J. Marks|chapter=Epoxy Resins |language=de|doi=10.1002/14356007.a09_547.pub2|title=Ullmann's Encyclopedia of Industrial Chemistry|year=2005|isbn=3527306730}}{{citation|surname1=Siegfried Rebsdat|surname2=Dieter Mayer|chapter=Ethylene Oxide |language=de|doi=10.1002/14356007.a10_117|title=Ullmann's Encyclopedia of Industrial Chemistry|year=2001|isbn=3527306730}}{{cite journal | year = 1995 | title = Spectroscopic investigation of the molybdenum active sites on MoVI heterogeneous catalysts for alkene epoxidation | journal = Journal of the Chemical Society, Faraday Transactions | doi = 10.1039/FT9959103969| last1 = Morazzoni | first1 = Franca | last2 = Canevali | first2 = Carmen | last3 = d'Aprile | first3 = Fiorenza | last4 = Bianchi | first4 = Claudia L. | last5 = Tempesti | first5 = Ezio | last6 = Giuffrè | first6 = Luigi | last7 = Airoldi | first7 = Giuseppe | volume = 91 | issue = 21 | pages = 3969–3974 }}
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.{{citation|surname1=Ambili, V K; Dr.Sugunan, S|editor-surname1=Faculty of Sciences|title=Studies on Catalysis by Ordered Mesoporous SBA-15 Materials Modified with Transition Metals |date=April 2011 |publisher=Cochin University of Science and Technology |language=de|url=http://dyuthi.cusat.ac.in/purl/2787|access-date=2014-07-27}} In recent times the catalytic oxidation of cyclohexene by (immobilized) metalloporphyrin complexes has been found to be an efficient way.{{cite journal | author = Costa, Andréia A. Ghesti | author2 = Grace F. de Macedo | author3 = Julio L. Braga | author4 = Valdeilson S. Santos| author5 = Marcello M. Dias | author6 = José A. Dias | author7 = Sílvia C.L. | year = 2008 | title = Immobilization of Fe, Mn and Co tetraphenylporphyrin complexes in MCM-41 and their catalytic activity in cyclohexene oxidation reaction by hydrogen peroxide | journal = Journal of Molecular Catalysis A: Chemical | volume = 282 | issue = 1–2 | pages = 149–157 | doi =10.1016/j.molcata.2007.12.024}}{{cite journal |author1=Xian-Tai Zhou |author2=Hong-Bing Ji |author3=Jian-Chang Xu |author4=Li-Xia Pei |author5=Le-Fu Wang |author6=Xing-Dong Yao | year = 2007 | title = Enzymatic-like mediated olefins epoxidation by molecular oxygen under mild conditions | journal = Tetrahedron Letters | volume = 48 | issue = 15 | pages = 2691–2695 | doi =10.1016/j.tetlet.2007.02.066}}
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.{{cite journal |last1=Brougham |first1=Paul |last2=Cooper |first2=Mark S. |last3=Cummerson |first3=David A. |last4=Heaney |first4=Harry |last5=Thompson |first5=Nicola |date=1987 |title=Oxidation Reactions Using Magnesium Monoperphthalate: A Comparison with m-Chloroperoxybenzoic Acid |url=https://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-1987-28153 |journal=Synthesis |volume=1987 |issue=11 |pages=1015–1017 |doi=10.1055/s-1987-28153 |access-date=2020-07-31}}
:File:Synthesis of cyclohexene oxide.svg
With this method, good yields up to 85 % can be reached.
Properties and reactions
Cyclohexene oxide has been studied extensively by analytical methods.{{cite journal |author1=RM Ibberson |author2=O. Yamamuro |author3=I. Tsukushi | year = 2006 | title =The crystal structures and phase behaviour of cyclohexene oxide | journal = Chemical Physics Letters | volume = 423 | issue = 4–6 | pages = 454–458 | bibcode = 2006CPL...423..454I| doi =10.1016/j.cplett.2006.04.004}} Cyclohexene oxide can be polymerized in solution, catalyzed by a solid acid catalyst.{{cite journal |author1=Ahmed Yahiaoui |author2=Mohammed Belbachir |author3=Jeanne Claude Soutif |author4=Laurent Fontaine | year = 2005 | title =Synthesis and structural analyses of poly(1,2-cyclohexene oxide) over solid acid catalyst | journal = Materials Letters | volume = 59 | issue = 7 | pages = 759–767 | doi =10.1016/j.matlet.2004.11.017}}