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Issue 10, 2008
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Cross-metathesis of oleyl alcohol with methyl acrylate: optimization of reaction conditions and comparison of their environmental impact

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Abstract

The synthesis of α,ω-difunctional monomers from the renewable resource oleyl alcohol via a cross-metathesis reaction with methyl acrylate is described. The reaction conditions were optimized for high conversions in combination with high cross-metathesis selectivity. The introduction of a protecting group for the alcohol functionality of oleyl alcohol was found to be a necessary step in order to significantly reduce the amount of metathesis catalyst required to obtain full conversions and good selectivities. All reaction conditions were compared to each other in a quantitative fashion with the program EATOS (environmental assessment tool for organic syntheses) revealing the environmentally most benign approach for the synthesis of the desired α,ω-difunctional monomers. These calculations also clearly revealed that the introduction of the protecting group was a necessary step in order to minimize the amount of the produced waste and to use the raw materials more efficiently.

Graphical abstract: Cross-metathesis of oleyl alcohol with methyl acrylate: optimization of reaction conditions and comparison of their environmental impact

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Publication details

The article was received on 29 May 2008, accepted on 23 Jul 2008 and first published on 12 Sep 2008


Article type: Paper
DOI: 10.1039/B808930B
Citation: Green Chem., 2008,10, 1099-1104
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    Cross-metathesis of oleyl alcohol with methyl acrylate: optimization of reaction conditions and comparison of their environmental impact

    A. Rybak and M. A. R. Meier, Green Chem., 2008, 10, 1099
    DOI: 10.1039/B808930B

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