EXPLORING THE USE OF ACETIC AND LEVULINIC ACIDS IN SOLID-PHASE SYNTHESIS OF RENEWABLE FUEL PRECURSORS

摘要

Two successful methods for attachment of acetic and levulinic acids to Merrifield and Wang resins were developed. In the first method, the acids were converted to the corresponding sodium salts using NaHCO3. These salts were reacted with Merrifield resin in the presence of n-Bu4NBr resulting in the attachment of the acids to the resin through an ester bond. The second method utilized diisopropylcarbodiimide as a coupling agent and 4-dimethylaminopyridine as a catalyst to achieve attachment of the acid through an ester bond. The formation of the ester bond was proven by IR spectroscopy. An in situ NMR ester cleavage procedure with CF3CO2H was developed to estimate the yield of the resin-bound esters. The yields calculated using this method were in good correlation with the yields determined for isolated hydrolysis products. Attempts to extend the carbon chains of the formed esters by treatment with LDA and ethyl acetate were unsuccessful.