AMADEus Seminar - Prof. Michael Meier - Tuesday 17 December 2013, 04:00 pm - Amphi IECB

Abstract: In ages of depleting fossil reserves and an increasing emission of greenhouse gases, it is obvious that the utilization of renewable feedstocks is one necessary step towards a sustainable development of our future. Especially plant 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 as well as polymers from plant oils as renewable resources will be discussed.[1]

For instance, we could show that different chain length ?,?-diester monomers can be obtained from fatty acid esters via olefin cross-metathesis (CM) with methyl acrylate taking advantage of natures "synthetic pool" of fatty acids with different chain lengths and positions of the double bonds.[2] Similarly, we could show that the cross-metathesis with allyl chloride and other functional olefins allows for the synthesis of ?,?-difunctional compounds. Moreover, thiol-ene click chemistry offers a complementary approach for the introduction of different functional groups to fatty acids in a straightforward and efficient manner, as demonstrated for the functionalization of the castor oil derived methyl 10-undecenoate with a variety of thiols.[4] Moreover, palladium catalyzed C-H activation was used to obtain acetoxy ester functionalized fatty acid methyl esters. Furthermore, a sustainable access to nitrogen containing monomers for the sustainable synthesis of renewable polyamides and polyurethanes will be discussed. The thus obtained renewable platform chemicals are valuable starting materials for a large variety of polymers.[6-9]

The focus of the presentation will be divided between the mentioned efficient (catalytic) routes to renewable step-growth monomers and the synthesis and properties of selected thereof derived polymers. In summary, we will thus demonstrate the versatility of plant-oil derived platform chemicals for the synthesis of a large variety of renewable monomers and polymers.

References:

[1] M. A. R. Meier, J. O. Metzger, U. S. Schubert, Chem. Soc. Rev. 2007, 36, 1788.; [2] A. Rybak, M. A .R. Meier, Green Chem. 2007, 9, 1356; [3] O. Türünç, M. A. R. Meier, Macromol. Rapid Commun. 2010, 31, 1822; [4] A. Rybak, M. A. R. Meier, ChemSusChem 2008, 1, 542; [5] O. Kreye, S. Wald, M. A. R. Meier, Adv. Synth. Catal. 2013, 355, 81-86; [6] P. A. Fokou, M. A. R. Meier, J. Am. Chem. Soc. 2009, 131, 1664; [7] L. Montero de Espinosa, M. A. R. Meier, Chem. Commun. 2011, 47, 1908.; [8] O. Türünç, M. A. R. Meier, Green Chem. 2011, 13, 314.; [9] O. Kreye, T. Tóth, M. A. R. Meier, J. Am. Chem. Soc. 2011, 133, 1790.