Solvent-free lipase-catalyzed synthesis of a novel hydroxyl-fatty acid derivative of kojic acid
•Lipase-catalyzed synthesis of a novel kojic acid derivative was investigated.•The optimization of the process was successfully performed.•The esterification of kojic acid greatly improved its lipophilicity.•KMR significantly improved the oxidative stability of rapeseed biodiesel.•Under optimal conditions the process was scaled up using a 5 L stirred tank reactor.
The aim of this work was the synthesis of a novel hydroxyl-fatty acid derivative of kojic acid rich in kojic acid monoricinoleate (KMR) which can be widely used in the cosmetic and food industry. The synthesis of KMR was carried out by lipase-catalysed esterification of ricinoleic and kojic acids in solvent-free system. Three immobilized lipases were tested and the best KMR yields were attained with Lipozyme TL IM and Novozym 435. Since Lipozyme TL IM is the cheapest, it was selected to optimize the reaction conditions. The optimal reaction conditions were 80 °C for the temperature, 1:1 for the alcohol/acid molar ratio, 600 rpm for stirring speed and 7.8% for the catalyst concentration. Under these conditions, the reaction was scaled up in a 5 × 10−3 m3 stirred tank reactor. 1H–13C HMBC-NMR showed that the primary hydroxyl group of kojic acid was regioselectively esterified. The KMR has more lipophilicity than kojic acid and showed antioxidant activity that improves the oxidation stability of biodiesel.
Journal: Enzyme and Microbial Technology - Volume 55, 5 February 2014, Pages 128–132