Abstract
In a context of dwindling oil reserves and environmental pressures, the chemical industry needs to innovate by developing new processes for producing bioproducts from raw plant materials. Unsaturated fatty acids from vegetable oils constitute a highly promising renewable resource that can be used to diversify productions, decreasing reliance on petroleum. A starting material rich in oleic acid has been obtained through the selection of high-oleic sunflower varieties and enzymatic hydrolysis of the oil they produce. The double bonds of this unsaturated raw material have been cleaved in green oxidizing conditions involving a biphasic lipophilic-aqueous system including hydrogen peroxide as an oxidant and a peroxo-tungsten complex Q3 {PO2 [WO(O2 )2 ]4 } as a phase-transfer catalyst (PTC) and co-oxidant. This PTC efficiently transferred oxygen to the substrate in the lipophilic phase. A mono-acid (pelargonic acid) and a di-acid (azelaic acid), with shorter, unusual hydrocarbon chains not present in the natural state, were synthesized and purified through an intensive process. Pelargonic acid was then formulated as an environmentally friendly biocontrol agent for weeds. We extended this green process of oxidative scission to other fatty acids and derivatives, to obtain other short-chain acids with diverse potential applications. This production chain (crops, reaction and purification processes, products, applications) is based on a sustainable development strategy.
Highlights
Unlike petrochemical feedstocks, oilseeds from cultivated plants can provide oxygen-containing molecules without damage to the ecosystem or human health
We focused on the oxidative cleavage of unsaturated fatty acids to yield unusual short-chain monocarboxylic and dicarboxylic acids that are rare in nature and are currently produced from fossil resources for industrial applications (Fig. 3)
This paper illustrates the steps of eco-conception in the design of processes for generating functional products, such as pelargonic acid (PA) and azelaic acid (AA)
Summary
Oilseeds from cultivated plants can provide oxygen-containing molecules (e.g. triglycerides) without damage to the ecosystem or human health. Plant breeders have modified the unsaturated fatty acid contents of oilseed crops, to develop new industrial markets for both food and other products. This diversification has included the development of high-oleic sunflower, which has a number of industrial applications, through chemical transformations into bio-based products. ARTERRIS (France) has developed a number of sunflower varieties with a “high oleic” acid content (87–88%), OLEIS with a “very high” oleic acid content (90–92%) and LINOLEIS which is enriched in linoleic acid (72%) The oils from these varieties are innovative high added-value products reducing the reliance of the processing industry on imported oils. We describe here one example of the development of a non-food application for high-oleic sunflower oil (Fig. 1), revealing the potential of unsaturated fatty acids in commercial oils for the generation of other platform molecules as valuable intermediates for the preparation of end-products
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