Issue 10, 2008

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

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

Article information

Article type
Paper
Submitted
29 May 2008
Accepted
23 Jul 2008
First published
12 Sep 2008

Green Chem., 2008,10, 1099-1104

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements