Cross-metathesis reactions of allyl chloride with fatty acid methyl esters: Efficient synthesis of α,ω-difunctional chemical intermediates from renewable raw materials

The synthesis of α,ω-difunctional chemical intermediates from renewable resources via the cross-metathesis reactions with allyl chloride is described. Different ruthenium metathesis catalysts were investigated and the reaction conditions were optimized for high conversions in combination with high cross-metathesis selectivity. New building blocks and chemical intermediates from fatty acid derivates were thus obtained in catalytic reactions with low catalyst loadings under bulk conditions. Therefore, a new potential use of renewable raw materials for the synthesis of intermediates for Nylon-11 and Nylon-12 was demonstrated.

Graphical abstractThe cross-metathesis of fatty acid methyl esters with allyl chloride under bulk conditions was investigated with second generation ruthenium olefin metathesis catalysts revealing that important α,ω-difunctional chemical intermediates can thus be obtained from renewable resources in an efficient catalytic reaction.Figure optionsDownload full-size imageDownload as PowerPoint slide