Lewis acid catalyzed cis (liquid) to trans (solid) isomerization of Jojoba oil in supercritical CO2

Authors: Liu, Zengshe - Kevin; SHAH, SHAILESH - The University Of Texas At Dallas; Vermillion, Karl; Cheng, Huai; Biswas, Atanu

Submitted to: Biocatalysis and Agricultural Biotechnology
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 10/19/2023
Publication Date: 10/20/2023
Citation: Liu, Z., Shah, S.N., Vermillion, K., Cheng, H.N., Biswas, A. 2023. Lewis acid catalyzed cis (liquid) to trans (solid) isomerization of Jojoba oil in supercritical CO2. Biocatalysis and Agricultural Biotechnology. 54. Article 102902. https://doi.org/10.1016/j.bcab.2023.102902.
DOI: https://doi.org/10.1016/j.bcab.2023.102902

Interpretive Summary: This research describes a new method to modify jojoba oil into a material suitable for cosmetic, food, fragrance, and pharmaceutical applications. Jojoba oil is obtained from the jojoba plant, which is native to the southwestern U.S. and northern Mexico. Naturally occurring jojoba oil is a liquid at room temperature and is not very stable. This research discovered a simple and effective single-step catalytic method to convert the oil into a solid with improved oxidative stability that melts around the same temperature as the human body. These attributes render the resulting solid more amenable to cosmetic and other applications than the unmodified jojoba oil. This research may ultimately expand markets for bio-based products from vegetable oils, thus reducing the environmental impact of and demand for petroleum-derived products while simultaneously enhancing rural economies by increasing the use of agricultural materials.

Technical Abstract: Isomerization of the olefin from cis to trans configuration is often a desirable reaction pathway that leads to products with different properties and chemical reactivities. In this work, we report a novel process involving the use of boron trifluoride diethyl etherate, BF3·O(C2H5)2 in supercritical CO2 that converts a compound with an isolated cis to a trans olefin in quantitative yield. No polymerization was observed. The utility of this reaction has been demonstrated by the conversion of jojoba oil (a natural wax ester, comprising a monoester of long-chain fatty acids with cis olefins) to its trans isomers. Jojoba oil is liquid at room temperature with a melting point of about 10°C; the reacted product is a solid with a melting point of 37.6°C (around the normal human body temperature). The simplicity of the reaction and the use of supercritical CO2 are the attractive features of this reaction.