Efficient Conversion of Renewable Unsaturated Fatty Acid Methyl Esters by Cross-Metathesis with Eugenol

Overview

Journal ACS Omega

Publisher American Chemical Society

Specialty Chemistry

Date 2019 Aug 29

PMID 31459214

Citations 4

Authors

Duy Le

Chanatip Samart

Ken Tsutsumi

Kotohiro Nomura

Suwadee Kongparakul

Affiliations

Soon will be listed here.

Abstract

Cross-metathesis of unsaturated fatty acid methyl esters (methyl oleate (MO), methyl petroselinate (MP), and methyl erucate (ME), obtained from vegetable oils) with eugenol (obtained from clove oil) proceeded under green, mild conditions (in 2-propanol or ethanol at 50 °C) in the presence of a ruthenium-carbene catalyst (called a second-generation Grubbs catalyst). These metathesis reactions proceeded with both high conversion (>90% of MO, MP) and selectivity (>98%) even with low catalyst loading (0.1 mol % Ru).

Citing Articles

Synthesis of new polyesters by acyclic diene metathesis polymerization of bio-based α,ω-dienes prepared from eugenol and castor oil (undecenoate).

Le D, Samart C, Kongparakul S, Nomura K RSC Adv. 2022; 9(18):10245-10252.

PMID: 35520893 PMC: 9062397. DOI: 10.1039/c9ra01065c.

Structural Transformation and Creativity Induced by Biological Agents during Fermentation of Edible Nuts from .

Odutayo O, Adegboye B, Omonigbehin E, Olawole T, Ogunlana O, Afolabi I Molecules. 2021; 26(19).

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Combining enyne metathesis with long-established organic transformations: a powerful strategy for the sustainable synthesis of bioactive molecules.

Dragutan V, Dragutan I, Demonceau A, Delaude L Beilstein J Org Chem. 2020; 16:738-755.

PMID: 32362948 PMC: 7176922. DOI: 10.3762/bjoc.16.68.

Looking for the Noncyclic(amino)(alkyl)carbene Ruthenium Catalyst for Ethenolysis of Ethyl Oleate: Selectivity Is on Target.

Wyrebek P, Malecki P, Sytniczuk A, Kosnik W, Gawin A, Kostrzewa J ACS Omega. 2019; 3(12):18481-18488.

PMID: 31458420 PMC: 6643780. DOI: 10.1021/acsomega.8b03119.

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