Fats and Oils as Renewable Feedstock for the Chemical ... - abiosus
Fats and Oils as Renewable Feedstock for the Chemical ... - abiosus
Fats and Oils as Renewable Feedstock for the Chemical ... - abiosus
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P6Cross-Meta<strong>the</strong>sis of Unsaturated Fatty Acid EstersAn<strong>as</strong>t<strong>as</strong>iya Rybak, Michael A. R. Meier*University of Applied Sciences Oldenburg/Ostfriesl<strong>and</strong>/WilhelmshavenJunior research group renewable raw materials, Faculty of Technology,Constantiaplatz 4, 26723 Emden, Germany*E-mail: michael.meier@fh-oow.de; Internet: http://www.meier-michael.comIn view of <strong>the</strong> continuous decre<strong>as</strong>e of fossil resources <strong>and</strong> incre<strong>as</strong>ing ecological damages,<strong>the</strong> <strong>as</strong>pects of a sustainable use of renewable raw materials have to be more <strong>and</strong> moretaken into consideration. 1,2 Especially <strong>for</strong> <strong>the</strong> conversion of <strong>the</strong>se resources into innovativenew materials <strong>as</strong> well <strong>as</strong> already existing chemical intermediates new <strong>and</strong> improvedchemical approaches are required.Olefin meta<strong>the</strong>sis h<strong>as</strong> emerged <strong>as</strong> a powerful tool <strong>for</strong> syn<strong>the</strong>tic organic <strong>as</strong> well <strong>as</strong> polymerchemistry. 3 As all o<strong>the</strong>r meta<strong>the</strong>sis reactions, olefin meta<strong>the</strong>sis is a process involving <strong>the</strong>exchange of a bond (or bonds) between similar interacting chemical species so that <strong>the</strong>bonding affiliations in <strong>the</strong> products are identical (or closely similar) to those in <strong>the</strong>reactants. 4 Practically, this results in <strong>the</strong> exchange of substituents of two reacting doublebonds, a transalkylidenation. In particular, <strong>the</strong> meta<strong>the</strong>sis of fatty acid derivatives, obtainedfrom plant oils, is a promising catalytic route that can be used <strong>for</strong> <strong>the</strong> syn<strong>the</strong>sis of chemicalintermediates from renewable raw materials. 5,6Our research applies <strong>the</strong> ru<strong>the</strong>nium-catalyzed cross meta<strong>the</strong>sis reaction of unsaturatedfatty acid esters (e.g. methyl oleate, methyl erucate or methyl 10-undecenoate) withvarious substituted olefins (e.g. 2-butene-1,4-diol, styrene, or methyl acrylate). Theresulting functionalized esters are promising monomers <strong>for</strong> <strong>the</strong> syn<strong>the</strong>sis of (novel)polymeric materials from renewable resources. Within this contribution, we will focus ourdiscussion on <strong>the</strong> syn<strong>the</strong>sis of <strong>the</strong> mentioned monomers describing in detail <strong>the</strong> use ofdifferent meta<strong>the</strong>sis catalysts <strong>and</strong> reactions conditions.Financial support from <strong>the</strong> German Federal Ministry of Food, Agriculture <strong>and</strong> Consumer Protection <strong>and</strong> <strong>the</strong>Fachagentur Nachwachsende Rohstoffe is kindly acknowledged.[1] The Summary of Fourth Assessment Report of Intergovernmental Panel on Climate Change (IPCC).Paris, 02.02.2007[2] United Nations Environment Programme (UNEP) 2006 Annual Report. Internet:http://www.unep.org/pdf/annualreport/UNEP_AR_2006_English.pdf[3] T. M. Trnka, R. H. Grubbs, Acc. Chem. Res. 2001, 34, 18-29[4] IUPAC Gold Book, Compendium of <strong>Chemical</strong> Terminology IUPAC Publications; Internet:http://goldbook.iupac.org/M03878.html[5] S. Warwel, H.-G Jägers, S. Thom<strong>as</strong>, Fat Sci. Technol. 1992, 94, 323-328[6] J. C. Mol, Green Chem. 2002, 4, 5-13.33
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