檸檬烯二環氧化物

化合物

檸檬烯二環氧化物(英語:Limonene diepoxide),又稱檸檬烯二氧化物(英語:Limonene dioxide[1],是一種有機化合物,化學式C10H16O2,可見於日本柳杉[2]菸草[3][4]等物種。工業上常用易得的檸檬烯原料氧化得到[1],如將檸檬烯利用氧化鋁過氧化氫作為催化劑進行氧化,可得到具有立體選擇性的檸檬烯二環氧化物[5],也可用過氧乙酸進行逐一氧化,先氧化環戊烯結構得到檸檬烯單環氧化物,後氧化異丙烯基支鏈得到[6]。檸檬烯二環氧化物可用於生產交聯劑、粘結劑以及環氧樹脂聚合物材料[1]

檸檬烯二環氧化物
IUPAC名
1-methyl-4-(2-methyloxiran-2-yl)-7-oxabicyclo[4.1.0]heptane
英文名 limonene diepoxide
別名 檸檬烯二氧化物
識別
CAS號 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
性質
化學式 C10H16O2
摩爾質量 168.23 g·mol−1
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。

參考資料

編輯
  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 (英語). 
  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.