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Synfacts 2010(3): 0366-0366  
DOI: 10.1055/s-0029-1219280
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Metathesis of Unsaturated Fatty Acid Esters with a Reusable Ruthenium Catalyst

Contributor(s): Yasuhiro Uozumi, Yoichi M. A. Yamada, Toshihiro Watanabe
Z. Yinghuai*, L. Kuijin, N. Huimin, L. Chuanzhao, L. P. Stubbs, C. F. Siong, T. Muihua, S. C. Peng
Institute of Chemical Engineering Science (ICES), Singapore Polytechnic and National University of Singapore, Singapore
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Publication History

Publication Date:
18 February 2010 (online)

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Significance

Metathesis of unsaturated fatty acid esters with a magnetic nanoparticle-supported Hoveyda-Grubbs catalyst 1 was described. Thus, self-metathesis of methyl oleate (2) was ­carried out in the presence of the immobilized Grubbs II catalyst 1 grafted onto magnetic nanoparticles (100 nm, matrix with starch) [2/1 (mol/mol) = 2008] to give dimethyl-9-octadecene-1,18-dioate (3) in 73% yield with 489 h-¹ TOF. Cross-metathesis of methyl oleate (2) and methyl acrylate (5) with 1 [2/1 (mol/mol) = 497] gave dimethyl undec-2-en-1,11-dioate (6) in 60% yield with 12 h-¹ TOF. Self-metathesis of a macro-monomer 8 using 1 [8/1 (mol/mol) = 98] ­afforded a polymer 9 in 90% yield with 29 h-¹ TOF.