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ARS Home » Midwest Area » Peoria, Illinois » National Center for Agricultural Utilization Research » Bio-oils Research » Research » Publications at this Location » Publication #413466

Research Project: New High-Value Biobased Materials with Applications Across Industry

Location: Bio-oils Research

Title: Cis (liquid) to trans (solid) isomerization of Jojoba oil in supercritical CO2 catalyzed by Lewis acid

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

Submitted to: American Chemical Society Abstracts
Publication Type: Abstract Only
Publication Acceptance Date: 5/21/2024
Publication Date: N/A
Citation: N/A

Interpretive Summary:

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 carbon dioxide 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 mono-ester of long-chain fatty acids with cis olefins to its trans isomers). Jojoba oil is a non-edible oil and 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.