New Syntheses with Soybean Oil As Renewable Feedstock Chemical Industry

New Syntheses with Soybean Oil as Renewable Feedstock for the Chemical Industry

Jürgen O. Metzger,x Ursula Biermann,x Sandra Fürmeier,x Marcel S.F. Lie Ken Jiexx

x Carl von Ossietzky Universität Oldenburg, Fachbereich Chemie, Carl-von-Ossitzky-Str. 9-11, 26111 Oldenburg

xx Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, SAR, China

Sustainable development had become the key ideal of the 20th century. In the search for sustainable chemistry, considerable importance is being attached to renewable raw materials which exploit the synthetic capabilities of nature.1 Oils and fats of vegetable and animal origin make up the greatest proportion of the current consumption of renewable raw materials in the chemical industry, since they offer to chemistry a large number of possibilities for applications which can be rarely met by petrochemistry. The chemical possibilties of renewable oils and fats are still very far from being fully exploited. During the last few years modern synthetic methods have been applied extensively to fatty compounds for the selective functionalisation of the alkyl chain.2 We have been performing radical, pericyclic and electrophilic additions to the C,C-double bond of unsaturated fatty compounds and obtained a large number of novel fatty compounds from which interesting properties are expected.

We are reporting here our results on chemical transformations of soybean oil. By means of simple industrial reaction, soybean oil is epoxidized. The epoxidized soybean oil was easily transesterified to give epoxidized methyl linoleate (methyl cis-9,10;cis-12,13-diepoxyoctadecanoate 1).

Epoxidized compounds are reactive substrates for a number of interesting follow up processes. We synthesized i.e. methyl cis-9,10;cis-12,13-diepithiooctadecanoate 2 substituting the epoxy functionality of compound 1 by the respective epithio functionality.3 Compound 2 is an interesting intermediate in the synthesis of heterocyclic and highly functionalized fatty compounds. The respective methyl cis-9,10;cis-12,13-diepiminooctadecanoate 3 was obtained in two reaction steps.4 The compound 3 showed remarkable cytotoxic and antitumor-promoting activity and a good neuroprotective effect.

Methyl linoleate was reacted with formaldehyde and higher aldehydes in the presence of Lewis acids i.e. aluminium chloride to form alkyl-substituted 4-chlorotetrahydropyrans in good yield and high selectivity.

1M. Eissen, J. O. Metzger, E. Schmidt, U. Schneidewind, Angew. Chem. Int. Ed. 2002, 414-436.

2U. Biermann, W. Friedt, S. Lang, W. Lühs, G. Machmüller, J. O. Metzger, Mark Rüsch gen. Klaas, H. Schäfer and M. P. Schneider, Angew. Chem. Int. Ed. 2000, 39, 2206-2224.

3M.S.F. Lie Ken Jie, Y.F. Zheng, Chem. Phys. Lipids 1988, 49, 167-178.

4J.O. Metzger, S. Fürmeier, Eur. J. Org. Chem. 1999, 661-664.