| Methodology for the synthesis of aliphatic and aromatic polyols, polyacids from vegetable oils and its derivatives have been described. First generation aliphatic polyols containing terminal hydroxyl functionalities were produced via ozonolysis of canola oil followed by catalytic hydrogenation of the ozonolysis product. The polyols are comprised of saturated triacylglycerols (TAGs), mono-ols, diols and triols, which were separated and purified by flash chromatography and identified by IR, 1H-NMR, 13C-NMR, and Mass Spectroscopy. An HPLC-ELSD method was developed to separate and quantify the four components in the polyols. Second generation polyols containing a significantly higher triol content and higher hydroxyl value were synthesized from canola oil by utilizing a milder solvent (ethyl acetate) and a more efficient reductive reagent (zinc) compared to the previous synthetic procedure.;Hexasubstituted benzene derivatives such as aromatic triols and triacids have been synthesized from oleic and erucic acid derivatives via a cyclotrimerization step catalyzed by palladium-on-carbon (Pd/C) and chlorotrimethylsilane (TMSC1). The asymmetric isomer, which is the main product, was isolated from its symmetric isomer by silica flash chromatography. All the products were fully characterized by IR, 1H-NMR, 13C-NMR and Mass Spectroscopy. These aromatic products are potentially useful monomers for the production of polyurethanes, polyesters and polyamides. It has been confirmed that the same pure fatty alkyne as derived from pure oleic acid, which is the precursor to the final hexasubstituted benzene derivatives, can be obtained from the mixture of fatty acids derived from the saponification of canola oil. Therefore, it is predicted that the same aromatic triol and triacid products can be obtained from canola oil as from pure oleic acid. |
