Determination of the Hydroxy and Carboxylic Acid Groups in Natural Complex Mixtures of Hydroxy Fatty Acids by (1)H Nuclear Magnetic Resonance Spectroscopy

Abstract

The use of trichloroacetyl isocyanate (TAI) to mark both hydroxyl and carboxyl groups borne by the hydrolysis or methanolysis of suberin fragments (a complex mixture of hydroxy fatty acids), allowed the quantitative assessment of the ratio between carboxyl and hydroxy groups, as well as the ratio between primary and secondary hydroxy groups, to be carried out reliably by (1)H nuclear magnetic resonance (NMR) spectroscopy. All the samples thus analyzed displayed an excess of CO(2)H (or CO(2)CH(3)) functions with respect to the OH counterparts, albeit to a variable extent, depending on the procedure adopted to isolate the suberin fragments. The precise knowledge of the molar ratio of these two reactive moieties is fundamental for the correct utilization of suberin monomers in polymerization reactions leading to aliphatic polyesters.