Editorial

The oleochemical feedstock wish list

As a new associate editor (and previous guest editor) of the European Journal of Lipid

Science and Technology, I would like to share some thoughts about ideal feedstock requirements

with you. My group is involved in the utilization of renewable raw materials, especially

plant oils, for the synthesis of monomers and polymers that might be able to replace

existing materials based on fossil resources. Inspired by our daily work with all its ups

and downs, I thought it might be interesting to communicate a wish list of oleochemical

feedstock requirements to the community. Who knows, maybe somebody already has some

answers?

Oleochemistry is a long established branch of industrial chemistry that has its roots in

soap making for centuries and was also influenced by the invention of catalytic plant oil

hydrogenation by Wilhelm Norman and its fast implementation on industrial scale during

the early 20th century. Nowadays, the products of oleochemistry are manifold and range

from basic starting materials (e.g., fatty alcohols and fatty acids) to detergents, lubricants,

paints, coatings, and many others. In order to establish new industrial uses of

plant oil derivatives, a continuous effort on basic research on new oleochemicals is

necessary [1]. In a chemist’s point of view, and in order to invent new processes that

are sustainable and along the lines of ‘‘green’’ chemistry, new feedstocks with the highest

possible content of only one fatty acid would be very beneficial. In this respect, high oleic

sunflower oil and castor oil, which are available on a large scale and have oleic and ricinoleic

acid contents exceeding 90%, respectively, are prime feedstocks for the synthesis of

oleochemicals. Especially castor oil has a well-developed industrial chemistry with countless

application possibilities of its derivatives [2]. However, these are only two examples and

further breeding and/or genetic engineering is necessary in order to develop more oils with

such characteristics.

Coming back to the chemist’s point of view, a wish list for an oleochemical feedstock

might include (but is not limited to) (i) oils with content of a certain fatty acid exceeding 90%,

(ii) availability of fatty acids with free choice of the amount and position of the double bond(s),

(iii) functional group containing fatty acids, and especially (iv) v-functionalized fatty acids

of various chain lengths. Some of the associated advantages would be: (i) no need of pre-

purification or component enrichment associated with higher yield and less waste;

(ii) easy introduction of established double bond follow up chemistry, but resulting in

new and desired and required products (e.g., moving the double bond position in oleic acid

from D-9 selectively to any other position and subsequent ozonolysis or cross-metathesis

would make different chain length diacids for polycondensation chemistry available);

(iii) no need for additional chemical or biotechnological conversion; (iv) availability of

polycondensation monomers for renewable polyesters and polyamides. Such engineered oils

might not only come from plant oils, but possibly also from algae or micro-organisms [3].

In any case, the selective and sustainable chemical transformation in combination

with biotechnology (e.g., enzymatic conversions, fermentation, genetic engineering, . . .)will be a key for the development of new oleochemical products. An excellent current example

in the field of chemistry is the selective synthesis of v-functionalized fatty acids via an

isomerizing methoxycarbonylation of methyl oleate [4] (or methyl linoleate and linolenate)

and methyl erucate and the subsequent polycondensation of the resulting a,v-diesters

to materials that have the potential to substitute polyethylene [5]. An equally

important breakthrough was achieved via biotechnology, when a Candida tropicalis

strain was engineered to produce commercially viable yields of v-hydroxyfatty acids [6].

More of such outstanding examples of chemistry and biotechnology, in combination with the

Michael Meier

Eur. J. Lipid Sci. Technol. 2011, 113, 1297–1298 DOI: 10.1002/ejlt.201100359 Editorial 1297

� 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim www.ejlst.com

mentioned optimal feedstocks, will be needed in order to meet the future challenges, not only

in oleochemistry, but in our society.

Michael Meier

Karlsruhe Institute of Technology, Karlsruhe, Germany

References

[1] Biermann, U., Bornscheuer, U., Meier, M. A. R., Metzger, J. O., Schafer, H. J., Oils and fats asrenewable raw materials in chemistry. Angew. Chem., Int. Ed. 2011, 50, 3854–3871.

[2] Mutlu, H., Meier, M. A. R., Castor oil as a renewable resource for the chemical industry. Eur. J.Lipid Sci. Technol. 2010, 112, 10–30.

[3] Bornscheuer, U., Can synthetic biology/metabolic engineering contribute to the microbial pro-duction of lipids and oleochemicals? Eur. J. Lipid Sci. Technol. 2011, 113, 1075–1076.

[4] Jimenez-Rodriguez, C., Eastham, G. R., Cole-Hamilton, D. J., Dicarboxylic acid esters from thecarbonylation of unsaturated esters under mild conditions. Inorg. Chem. Commun. 2005, 8, 878–881.

[5] Quinzler, D., Mecking, S., Linear semicrystalline polyesters from fatty acids by complete feed-stock molecule utilization. Angew. Chem., Int. Ed. 2010, 49, 4306–4308.

[6] Lu, W., Ness, J. E., Xie, W., Zhang, X. et al., Biosynthesis of monomers for plastics fromrenewable oils. J. Am. Chem. Soc. 2010, 132, 15451–15455.

1298 M. Meier Eur. J. Lipid Sci. Technol. 2011, 113, 1297–1298

� 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim www.ejlst.com