環氧環己烷

環氧環己烷
	IUPAC名; 7-Oxabicyclo[4.1.0]heptane
別名	氧化環己烯
識別
CAS號	286-20-4
PubChem	9246
ChemSpider	8890
SMILES	C1CCC2C(C1)O2;
性質
化學式	C6H10O
摩爾質量	98.14 g·mol−1
外觀	無色液體
密度	0.97 g·cm−3
熔點	ca. -40 °C
沸點	ca. 130 °C
溶解性（水）	部分溶解
蒸氣壓	12 mbar (at 20 °C)
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

環氧環己烷（英語：Cyclohexene oxide，Epoxycyclohexane）是一種環烷烴環氧化合物。其可作為單體經陽離子聚合成具有熱塑性的聚環氧環己烷。

合成

環氧環己烷可由環己烯經環氧化反應得到。反應體系可以與過氧酸進行均相反應得到^[2]，也可以利用催化劑（如銀與氧氣反應）進行非均相反應得到^[3]^[4]^[5]。

工業生產環氧環己烷更傾向於採用非均相催化反應，因為這樣有更好的原子經濟性，而且產物容易分類，催化劑可回收重複利用。採用的過氧酸常為過氧化氫^[6]。近年來也發現了採用固定化的金屬卟啉絡合物催化氧化有很高的效率^[7]^[8]。

在實驗中，常用環己烯與單過氧鄰苯二甲酸鎂（英語：Magnesium monoperoxyphthalate）(MMPP)的水-異丙醇溶液室溫下反應得到環氧環己烷，且反應產率可達到85%^[9]。

性質和反應

環氧環己烷的晶體結構已通過分析方法得到廣泛研究。環氧環己烷可在溶液中經固體酸催化劑的催化下聚合形成聚環氧環己烷^[10]。

參考文獻

^ ^1.0 ^1.1 ^1.2 ^1.3 ^1.4 ^1.5 Record of Epoxycyclohexane in the GESTIS Substance Database from the IFA（英語：Institute for Occupational Safety and Health）, accessed on 1 February 2014
^ M. Quenard; V. Bonmarin; G. Gelbard. Epoxidation of olefins by hydrogen peroxide catalyzed by phosphonotungstic complexes. Tetrahedron Letters. 1987, 28 (20): 2237–2238. doi:10.1016/S0040-4039(00)96089-1.
^ Ha Q. Pham; Maurice J. Marks, Epoxy Resins, Ullmann's Encyclopedia of Industrial Chemistry, 2005, ISBN 3527306730, doi:10.1002/14356007.a09_547.pub2 （德語）
^ Siegfried Rebsdat; Dieter Mayer, Ethylene Oxide, Ullmann's Encyclopedia of Industrial Chemistry, 2001, ISBN 3527306730, doi:10.1002/14356007.a10_117 （德語）
^ Morazzoni, Franca; Canevali, Carmen; d'Aprile, Fiorenza; Bianchi, Claudia L.; Tempesti, Ezio; Giuffrè, Luigi; Airoldi, Giuseppe. Spectroscopic investigation of the molybdenum active sites on Mo^VI heterogeneous catalysts for alkene epoxidation. Journal of the Chemical Society, Faraday Transactions. 1995, 91 (21): 3969–3974. doi:10.1039/FT9959103969.
^ Ambili, V K; Dr.Sugunan, S, Faculty of Sciences , 編, Studies on Catalysis by Ordered Mesoporous SBA-15 Materials Modified with Transition Metals, Cochin University of Science and Technology, April 2011 [2014-07-27], （原始內容存檔於2020-06-05）（德語）
^ Costa, Andréia A. Ghesti; Grace F. de Macedo; Julio L. Braga; Valdeilson S. Santos; Marcello M. Dias; José A. Dias; Sílvia C.L. 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. 2008, 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. Enzymatic-like mediated olefins epoxidation by molecular oxygen under mild conditions. Tetrahedron Letters. 2007, 48 (15): 2691–2695. doi:10.1016/j.tetlet.2007.02.066.
^ Brougham, Paul; Cooper, Mark S.; Cummerson, David A.; Heaney, Harry; Thompson, Nicola. Oxidation Reactions Using Magnesium Monoperphthalate: A Comparison with m-Chloroperoxybenzoic Acid. Synthesis. 1987, 1987 (11): 1015–1017 [2020-07-31]. doi:10.1055/s-1987-28153. （原始內容存檔於2024-04-15）.
^ Ahmed Yahiaoui; Mohammed Belbachir; Jeanne Claude Soutif; Laurent Fontaine. Synthesis and structural analyses of poly(1,2-cyclohexene oxide) over solid acid catalyst. Materials Letters. 2005, 59 (7): 759–767. doi:10.1016/j.matlet.2004.11.017.

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[GESTIS-1] 1.0 ^1.1 ^1.2 ^1.3 ^1.4 ^1.5 Record of Epoxycyclohexane in the GESTIS Substance Database from the IFA（英語：Institute for Occupational Safety and Health）, accessed on 1 February 2014

[2] M. Quenard; V. Bonmarin; G. Gelbard. Epoxidation of olefins by hydrogen peroxide catalyzed by phosphonotungstic complexes. Tetrahedron Letters. 1987, 28 (20): 2237–2238. doi:10.1016/S0040-4039(00)96089-1.

[3] Ha Q. Pham; Maurice J. Marks, Epoxy Resins, Ullmann's Encyclopedia of Industrial Chemistry, 2005, ISBN 3527306730, doi:10.1002/14356007.a09_547.pub2 （德語）

[4] Siegfried Rebsdat; Dieter Mayer, Ethylene Oxide, Ullmann's Encyclopedia of Industrial Chemistry, 2001, ISBN 3527306730, doi:10.1002/14356007.a10_117 （德語）

[5] Morazzoni, Franca; Canevali, Carmen; d'Aprile, Fiorenza; Bianchi, Claudia L.; Tempesti, Ezio; Giuffrè, Luigi; Airoldi, Giuseppe. Spectroscopic investigation of the molybdenum active sites on Mo^VI heterogeneous catalysts for alkene epoxidation. Journal of the Chemical Society, Faraday Transactions. 1995, 91 (21): 3969–3974. doi:10.1039/FT9959103969.

[6] Ambili, V K; Dr.Sugunan, S, Faculty of Sciences , 編, Studies on Catalysis by Ordered Mesoporous SBA-15 Materials Modified with Transition Metals, Cochin University of Science and Technology, April 2011 [2014-07-27], （原始內容存檔於2020-06-05）（德語）

[7] Costa, Andréia A. Ghesti; Grace F. de Macedo; Julio L. Braga; Valdeilson S. Santos; Marcello M. Dias; José A. Dias; Sílvia C.L. 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. 2008, 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. Enzymatic-like mediated olefins epoxidation by molecular oxygen under mild conditions. Tetrahedron Letters. 2007, 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. Oxidation Reactions Using Magnesium Monoperphthalate: A Comparison with m-Chloroperoxybenzoic Acid. Synthesis. 1987, 1987 (11): 1015–1017 [2020-07-31]. doi:10.1055/s-1987-28153. （原始內容存檔於2024-04-15）.

[10] Ahmed Yahiaoui; Mohammed Belbachir; Jeanne Claude Soutif; Laurent Fontaine. Synthesis and structural analyses of poly(1,2-cyclohexene oxide) over solid acid catalyst. Materials Letters. 2005, 59 (7): 759–767. doi:10.1016/j.matlet.2004.11.017.

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