Jojoba Oil Olefin Metathesis: A Valuable Source for Bio-Renewable Materials

Jojoba oil is a diene composed of two monounsaturated hydrocarbon chains linked by an ester moiety. Ruthenium catalysed cross-metathesis reactions (CM) of the oil produced ADMET oligomers and hydrocarbon by-products under various conditions.¹ Both the polyester oligomers and the hydrocarbon distillates were analysed by several analytical techniques. The oligomers were also hydrolysed under basic conditions to assess potential degradability. Oligomerisation of the starting material by an alternative thiol-ene ‘click’ reaction was also probed. A high atom economy is expected for this catalytic process given that all products obtained may be used either as sources for bio-fuel (hydrocarbons), or as potential renewable and degradable materials (polyester chains). In addition, a novel methodology for a concise preparation of synthetic jojoba oil will be presented.

Cyclic alkyl amino carbene (CAAC) ligands are a class of σ-donor ligands which was introduced first by Bertrand et al. in 2005.² Ruthenium catalysts bearing this type of ligands showed high reactivity towards ethenolysis³ (TON = 340,000) and CM⁴ (TON = 315,000) reactions. Reactions of Jojoba oil and CAAC bearing ruthenium catalysts were conducted in different conditions in order to make the reaction more efficient and achieve better materials. Results will be presented.

Reference

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