Catalytic access to bifunctional products from plant oil derivatives

Plant oils constitute a class of renewable raw materials which can produce a large variety of chemicals useful for industry. The cross-metathesis of unsaturated fatty esters, derived from seed oils, with functionalized olefins has potential to generate bifunctional compounds, as it has been shown by reactions with acrylates[1]. The objective of our presentation will be to describe, with some practical aspects, the cross-metathesis reactions of both terminal and internal double bond containing esters, arising from seed oils, with acrylonitrile. This metathesis was performed using ruthenium catalysts and led to bifunctional nitrile-esters with high conversions [2]. TON improvement was achieved by slow addition of catalyst.

It will be shown that the metathesis catalyst residue can be used as a hydrogenation catalyst in a sequential cross-metathesis/hydrogenation process leading to saturated nitrile-esters.
The prepared bifunctional nitrile-esters are precursors of amino acid monomers for the production of polyamides from renewable resources.

[1] A. Rybak, M. A. R. Meier, Green Chem., 2007, 9, 1356; Green Chem., 2008, 10, 1099.
[2] For initial study see: R. Malacea, C. Fischmeister, C. Bruneau, J-L. Dubois, J-L. Couturier, P. H. Dixneuf, Green Chem., 2009, in press.