Submitted to: Green Chemistry
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 4/4/2003
Publication Date: 6/19/2003
Citation: LASZLO, J.A., COMPTON, D.L., ELLER, F.J., TAYLOR, S.L., ISBELL, T. PACKED-BED BIOREACTOR SYNTHESIS OF FERULOYLATED MONOACYL- AND DIACYLGLYCEROLS: CLEAN PRODUCTION OF A "GREEN" SUNSCREEN. GREEN CHEMISTRY. Vol 5, 382-386. 2003. Interpretive Summary: One approach to increase the value of commodity vegetable oils is to transform them by introducing novel functional groups into the oil, which will allow new uses to be found for vegetable oils. Incorporating a natural ultraviolet light-absorbing molecule into vegetable oil may allow this new material to be used as a sunscreen, particularly if this can be done by a process suitable for industrial production. We found a method that readily produces a sunscreen agent from vegetable oil and that can be efficiently scaled up for large volumes of the product. This process does not use hazardous chemicals or produce waste products.
Technical Abstract: Concerns have been raised about the potental adverse health and ecological effects of the commonly used sunscreen active ingredients. A sunscreen active ingredient can be derived from two natural plant components, ferulic acid and triglycerides. Transesterification of ferulic acid ethyl ester with vegetable oil produces a mixture of feruloylated monoacyl- and diacylglycerols that have a strong UVA/B absorbance. The reaction is catalyzed by the immobilized enzyme Candida antarctica lipase B. We examined the influence of operating conditions on the service life of the immobilized enzyme in packed beds and found that the enzyme had very good long-term stability. Unreacted ferulic acid ethyl ester and ethyl esters of fatty acids can be separated from the product using liquid carbon dioxide extraction or molecular distillation. The recovered materials can be converted to sunscreen product by a second round of reaction with the biocatalyst, demonstrating a synthesis of a plant-derived, environmentally benign sunscreen.