An approach to renewable Nylon-11 and Nylon-12 via olefin cross-metathesis

An approach to renewable Nylon-11 and Nylon-12 via olefin cross-metathesis

Tina Jacobs, Michael A. R. Meier*

University of Applied Sciences Oldenburg/Ostfriesland/Wilhelmshaven, Constantiaplatz 4, Emden, Germany; *:E-mail: michael.meier@fh-oow.de; Internet: www.meier-michael.com

In ages of depleting fossil reserves and increasing emission of green house gases it is obvious that the utilization of renewable feedstocks is one necessary step towards a sustainable development of our future. Especially plant derived oils bear a large potential for the substitution of currently used petrochemicals, since a variety of value added chemical intermediates can be derived from these resources in a straightforward fashion taking full advantage of nature’s synthetic potential.
Here, new approaches for the synthesis of monomers from plant oils as renewable resources[1] via olefin metathesis[2,3] will be discussed. In particular, the synthesis of α,ω-difunctional chemical intermediates from renewable resources via the cross-metathesis reaction of fatty acid methyl esters with allyl chloride is described.[4] 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.

References:

[1] M. A. R. Meier, J. O. Metzger, U. S. Schubert, Chem. Soc. Rev. 2007, 36, 1788.
[2] R. H. Grubbs, Angew. Chem. Int. Ed. 2006, 45, 3760.
[3] A. Rybak, P. A. Fokou, M. A. R. Meier, Eur. J. Lipid Sci. Technol. 2008, 110, 797.
[4] T. Jacobs, A. Rybak, M. A. R. Meier, Appl. Catal., A 2009, 353 32.