Metathesis and other efficient (catalytic) approaches to renewable monomers and polymers

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 renewable resources in a straightforward fashion taking full advantage of nature’s synthetic potential.[1,2] Here, new approaches for the synthesis of monomers[3,4,5] as well as polymers[6,7,8,9] from plant oils as renewable resources will be discussed.
Especially olefin cross-metathesis allows an efficient catalytic access to α,ω-difunctional fatty acid derivatives.[3,4,5] Moreover, thiol-ene click chemistry offers a complementary approach for the introduction of a large variety of functional groups to fatty acids in a straightforward and efficient manner. Both approaches are fully along the lines with the principles of green chemistry and offer the possibility to efficiently functionalize fatty acid derivatives. The thus obtained renewable platform chemicals are valuable starting materials for a variety of polyesters and polyamides.[6]
Additionally, acyclic diene metathesis (ADMET) can be used to directly obtain macromolecules from such starting materials.[7,8] Linear as well as highly branched polyesters with interesting application possibilities can be obtained from fatty acid derived monomers in that way. Moreover, we could recently show that this approach is also suitable for the direct polymerization of high oleic sunflower oil.[9]

References:

[1] M. A. R. Meier, Macromol. Chem. Phys. 2009, 210, 1073.
[2] A. Rybak, P. A. Fokou, M. A. R. Meier, Eur. J. Lipid Sci. Technol. 2008, 110, 797.
[3] A. Rybak, M. A. R. Meier, Green Chem. 2007, 9, 1356.
[4] T. T. T. Ho, M. A. R. Meier, ChemSusChem 2009, 2, 749.
[5] G. B. Djigoué, M. A. R. Meier, Appl. Catal., A 2009, 368, 158.
[6] H. Mutlu, M. A. R. Meier, Macromol. Chem. Phys. 2009, 210, 1019.
[7] A. Rybak, M. A. R. Meier, ChemSusChem 2008, 1, 542.
[8] P. A. Fokou, M. A. R. Meier, J. Am. Chem. Soc. 2009, 131, 1664.
[9] U. Biermann, J. O. Metzger, M. A. R. Meier, Macromol. Chem. Phys. 2010, accepted.