柠檬烯二环氧化物

柠檬烯二环氧化物
	IUPAC名; 1-methyl-4-(2-methyloxiran-2-yl)-7-oxabicyclo[4.1.0]heptane
英文名	limonene diepoxide
别名	柠檬烯二氧化物
识别
CAS号	96-08-2
PubChem	232703
ChemSpider	202849
SMILES	CC12CCC(CC1O2)C3(CO3)C;
InChI	InChI=1S/C10H16O2/c1-9-4-3-7(5-8(9)12-9)10(2)6-11-10/h7-8H,3-6H2,1-2H3;
InChIKey	RBHIUNHSNSQJNG-UHFFFAOYSA-N
性质
化学式	C10H16O2
摩尔质量	168.23 g·mol−1
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

柠檬烯二环氧化物（英语：Limonene diepoxide），又称柠檬烯二氧化物（英语：Limonene dioxide）^[1]，是一种有机化合物，化学式C₁₀H₁₆O₂，可见于日本柳杉^[2]、烟草^[3]、姜^[4]等物种。工业上常用易得的柠檬烯原料氧化得到^[1]，如将柠檬烯利用氧化铝和过氧化氢作为催化剂进行氧化，可得到具有立体选择性的柠檬烯二环氧化物^[5]，也可用过氧乙酸进行逐一氧化，先氧化环戊烯结构得到柠檬烯单环氧化物，后氧化异丙烯基支链得到^[6]。柠檬烯二环氧化物可用于生产交联剂、粘结剂以及环氧树脂等聚合物材料^[1]。

参考资料

^ ^1.0 ^1.1 ^1.2 Luc Charbonneau, Xavier Foster, Dongyuan Zhao, Serge Kaliaguine. Catalyst-Free Epoxidation of Limonene to Limonene Dioxide. ACS Sustainable Chemistry & Engineering. 2018, 6 (4): 5115–5. doi:10.1021/acssuschemeng.7b04782.
^ Gaston Vernin; Jacques Metzger; Jean-Pierre Mondon; Jean-Claude Pieribattesti. GC/MS Analysis of the Leaf Oil of Cryptomeria japonica D. Don from Reunion Island. Journal of Essential Oil Research. 2012-04, 3 (4). doi:10.1080/10412905.1991.9697930.
^ Xianzhong Zhang; Hongjian Gao; Lifen Zhang; Donghong Liu; Xingqian Ye. Extraction of essential oil from discarded tobacco leaves by solvent extraction and steam distillation, and identification of its chemical composition. Industrial Crops and Products. 2012-03, 39. doi:10.1016/J.INDCROP.2012.02.029.
^ Fan Gong; Ying-Sing Fung; Yi-Zeng Liang. Determination of volatile components in ginger using gas chromatography-mass spectrometry with resolution improved by data processing techniques. Journal of Agricultural and Food Chemistry. 2004-10, 52 (21). doi:10.1021/JF040102Z （英语）.
^ Anderson J. Bonon, Juliana O. Bahú, Bruno C. Klein, Dalmo Mandelli, Rubens Maciel Filho. Green production of limonene diepoxide for potential biomedical applications. Catalysis Today. 2022,. 388-389: 288-300. doi:10.1016/j.cattod.2020.06.030.
^ James V. Crivello, Bo Yang. Studies of synthesis and cationic photopolymerization of three isomeric monoterpene diepoxides. Journal of Polymer Science Part A: Polymer Chemistry. 1995, 33 (11): 1881-1890. doi:10.1002/pola.1995.080331116.

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[:0-1] 1.0 ^1.1 ^1.2 Luc Charbonneau, Xavier Foster, Dongyuan Zhao, Serge Kaliaguine. Catalyst-Free Epoxidation of Limonene to Limonene Dioxide. ACS Sustainable Chemistry & Engineering. 2018, 6 (4): 5115–5. doi:10.1021/acssuschemeng.7b04782.

[2] Gaston Vernin; Jacques Metzger; Jean-Pierre Mondon; Jean-Claude Pieribattesti. GC/MS Analysis of the Leaf Oil of Cryptomeria japonica D. Don from Reunion Island. Journal of Essential Oil Research. 2012-04, 3 (4). doi:10.1080/10412905.1991.9697930.

[3] Xianzhong Zhang; Hongjian Gao; Lifen Zhang; Donghong Liu; Xingqian Ye. Extraction of essential oil from discarded tobacco leaves by solvent extraction and steam distillation, and identification of its chemical composition. Industrial Crops and Products. 2012-03, 39. doi:10.1016/J.INDCROP.2012.02.029.

[4] Fan Gong; Ying-Sing Fung; Yi-Zeng Liang. Determination of volatile components in ginger using gas chromatography-mass spectrometry with resolution improved by data processing techniques. Journal of Agricultural and Food Chemistry. 2004-10, 52 (21). doi:10.1021/JF040102Z （英语）.

[5] Anderson J. Bonon, Juliana O. Bahú, Bruno C. Klein, Dalmo Mandelli, Rubens Maciel Filho. Green production of limonene diepoxide for potential biomedical applications. Catalysis Today. 2022,. 388-389: 288-300. doi:10.1016/j.cattod.2020.06.030.

[6] James V. Crivello, Bo Yang. Studies of synthesis and cationic photopolymerization of three isomeric monoterpene diepoxides. Journal of Polymer Science Part A: Polymer Chemistry. 1995, 33 (11): 1881-1890. doi:10.1002/pola.1995.080331116.

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