Green Conversion of Eugenol to Isoeugenol
Mentor:Kimberley Cousins, Professor of Chemistry, California State University San Bernardino
The conversion of eugenol to isoeugenol is important in the flavor and fragrance industry, and is a model for bond migration reactions. This reaction can be made greener by substituting water for most of the ethylene glycol, and greatly reducing the amount of base used, with microwave heating. By using less hydrocarbon solvent and caustic base, we can ensure a green reaction with the least amount of waste possible that would cause harm to the environment. Experiments have shown that a maximum of 80% of the ethylene glycol can be replaced with water, and that a 2:1 ratio of base to eugenol (vs. the tradition 4:1 ratio) will afford reaction. The conversion and recovery of isoeugenol from the experiment is optimized by short reaction times at moderately high temperatures attained by using reaction pressure tube and mid-range microwave wattages. Both geometric isomers of isoeugenol (cis and trans) are formed in ratios that vary with reaction conditions.