(199d) Synthesis Of Renewable Chemicals From Oleic Acid

As petroleum prices continue to increase, alternative sources of fuels and chemicals traditionally derived from petroleum must be identified. Biomass is an attractive option because of its availability and low cost. In particular, lipids derived from biomass provide a renewable feedstock to synthesize a wide range of fuels and chemicals. Animals, plants, and microorganisms are biomass sources potentially rich in lipids. In fact, biodiesel, a renewable alternative to petroleum diesel, is produced primarily from soybean lipids. Individual lipid components must be considered as a source of chemicals. For example, many lipid sources contain unsaturated fatty acids, which can be oxidized to form a variety of products such as diacids and epoxides. These chemicals are valuable intermediates for the formulation of pharmaceuticals, herbicides, detergents, plasticizers, lubricants, paints, and other useful products.

Oleic acid is one of the most common unsaturated fatty acids found in biomass. In this paper, a kinetic analysis of oleic acid oxidation with t-butyl hydroperoxide was performed, and the results were compared to carrying out the reaction in sub- and supercritical carbon dioxide. The different solubility of the reaction products in the supercritical mixture can be employed to perform reaction and fractionation in one step. Furthermore, since carbon dioxide is already completely oxidized, reactions in supercritical carbon dioxide minimize the production of unwanted reaction by-products.