New Syntheses with Oils and Fats as Renewable Raw Materials for the Chemical Industry

• Published in: Angewandte Chemie International Edition Vol. 39; no. 13; pp. 2206 - 2224
• Main Authors: Biermann, Ursula, Friedt, Wolfgang, Lang, Siegmund, Lühs, Wilfried, Machmüller, Guido, Metzger, Jürgen O., Rüsch gen. Klaas, Mark, Schäfer, Hans J., Schneider, Manfred P.
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag GmbH 03.07.2000; WILEY‐VCH Verlag GmbH
• Subjects: additions; enzyme catalysis; fatty acids; gene technology; renewable resources
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/1521-3773(20000703)39:13<2206::AID-ANIE2206>3.0.CO;2-P

Oils and fats are the most important renewable raw materials for the chemical industry. Hitherto, industrial oleochemistry has concentrated predominantly on the carboxy functionality of fatty acids but, more recently, modern synthetic methods have been applied extensively to fatty compounds for the selective functionalization of the alkyl chain. Radical, electrophilic, nucleophilic, and pericyclic as well as transition metal catalyzed additions to the C−C double bond of, for example, oleic acid as the prototype of a readily accessible, unsaturated fatty acid have led to a large number of novel fatty compounds from which interesting properties are expected. Functionalization of C−H bonds in the alkyl chain is also feasible with remarkable selectivity. Effective and highly versatile catalysts for the metathesis of esters of unsaturated fatty acids have been developed, which lead to new and interesting ω‐unsaturated fatty acids. The epoxidation of unsaturated fatty acids has been developed extensively. Enzymatic reactions allow syntheses with high selectivity and yield of mono‐ and diglycerides and esters of carbohydrates with a variety of surfactant properties. Regio‐ and enantioselective microbial hydrations and hydroxylations widen the spectrum of selective reactions. Of considerable significance is that, with the use of gene technology, natural oils and fats have been improved significantly and will be improved still further, insofar as they show a more uniform and often unusual fatty acid spectrum. Numerous fatty acids are now available in a purity which makes them attractive for synthesis and as raw materials for the chemical industry. Chemical raw materials from the farmer? Thanks to modern plant breeding and gene technology, oils and fats are so chemically pure—the “new sunflower” produces 83 % oleic acid—that they have become attractive for synthesis. In recent years, through the use of modern synthetic methods including enzymatic and microbiological methods, hundreds of novel fatty compounds with potentially interesting properties have been made available.