Separation of C18 Fatty Acid Esters and Fatty Acids Derived from Vegetable Oils Using Nanometer-Sized Covalent Organic Frameworks Incorporated in Polyepoxy Membranes

Fatty acids (FAs) and FA methyl esters (FAMEs) are easily isolated from vegetable oil and are important starting materials for the chemical industry to produce commercial products that are green, biorenewable, and nontoxic. A challenge in these applications is that mixtures of five or more FAs and FAMEs are isolated from a vegetable oil source, and methods to separate these mixtures are decades old and have increasingly high costs associated with the production of high-purity single-component FAs or FAMEs. We developed a method to separate these mixtures using mixed matrix membranes containing nano-meter-sized covalent organic frameworks. The 2D, crystalline COFs possessed narrow distributions of pore sizes of 1.3, 1.8, 2.3, and 3.4 nm that separated FAs and FAMEs based on their degrees of unsaturation. The COFs were synthesized, characterized, and then encapsulated at 10 or 20% by weight into a prepolymer of epoxy that was then fully cured. For all mixed matrix membranes, as the degree of unsaturation increased, the FAs or FAMEs had a slower flux. The largest difference in flux was obtained for a COF/epoxy membrane with a pore size of 1.8 nm, and methyl stearate had a 5.9x faster flux than methyl linolenate. These are the first membranes that can separate the important C18 FAs and FAMEs found in vegetable oil.