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.