Welcome to Chemistry and Industry of Forest Products,

Chemistry and Industry of Forest Products ›› 2021, Vol. 41 ›› Issue (3): 11-18.doi: 10.3969/j.issn.0253-2417.2021.03.002

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Effect Mechanism of Substrates on Cross-metathesis Reaction for Preparation of Long-chain Terminal Olefin Chemicals from Methyl Oleate

Hengyi SHU1,3, Zhifeng ZHENG3,4, Shouqing LIU1,3, Hongzhou HE2, Yuanbo HUANG2,3,*()   

  1. 1. School of Materials Science & Engineering, Southwest Forestry University, Kunming 650224, China
    2. School of Mechanical & Energy Engineering, Jimei University, Xiamen 361021, China
    3. National Local Joint Engineering Research Center for Efficient Utilization of Forestry Biomass Resources; Key Laboratory for Highly-efficient Utilization of Forest Biomass Resources in the Southwest China, National Forestry and Grassland Administration, Southwest Forestry University, Kunming 650224, China
    4. Xiamen Key Laboratory for High-valued Conversion Technology of Agricultural Biomass(Xiamen University); Fujian Provincial Engineering and Research Center of Clean and High-valued Technologies for Biomass; College of Energy, Xiamen University, Xiamen 361102, China
  • Received:2020-10-27 Online:2021-06-28 Published:2021-07-01
  • Contact: Yuanbo HUANG E-mail:youthshow@163.com


The long-chain terminal olefin compounds 1-decene(CM1) and methyl 9-decenoate(CM2) were prepared through olefin cross-metathesis of methyl oleate(MO) with low olefin substrate. The second-generation Hoveyda-Grubbs catalyst was screened out from 4 typical ruthenium-catalyst through the self-metathesis of methyl oleate. The catalytic mechanism was discussed with 4 substrates, then the proposed mechanism was verified by 6 substrates. The results suggested that the short-chain substrates containing electron-rich and bulk-large group like styrene, eugenol and allyl trimethylsilane were beneficial for the preparation of terminal olefin products, since the property of aromatic group, which could chelate with central metal and formed the key ring intermediate, so that it changed the route of reaction and prepared the highly-selectivity of the aim product yield.

Key words: methyl oleate, olefin cross-metathesis, ruthenium-complex catalyst, α-olefin, methyl 9-decenoate

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