1,3-specific lipolysis ofLesquerella fendlerioil by immobilized and reverse-micellar encapsulated enzymes

Three types of reaction systems, all batch-mode, were employed for production of hydroxy (lesquerolic and auricolic) fatty acidsvia1,3-specific lipolysis ofLesquerella fendlerioil: “Free”Rhizopus arrhizusor immobilizedRhizomucor mieheilipase (Lipozyme™) in reverse micelles (System 1), Lipozyme suspended in lesquerella oil/isooctane mixture (System 2) and a suspension of water and freeR. mieheilipase in lesquerella oil/isooctane (System 3). The objective was to find the system that best maximized yield (i.e., percent hydrolysis), the proportion of hydroxy acids among the free acids liberated (hydroxy acid “purity”), and recovery/reuse of lipase activity, and that could be easily adapted into a large-scale process. System 1 provided the largest percent hydrolysis (55%) and hydroxy acid purity (85%), but of the three systems would be the most difficult to scale up. Thus, System 1 would be the most desirable reaction system only when small batch sizes are to be processed. System 3 yielded 47.2% hydrolysis, but the hydroxy acid purity was at most 73%, making it the least desirable of the three systems to employ. System 2 yielded moderate extents of hydrolyses (30–40%) and large hydroxy acid purity initially (80–83%), but the purity decreased slightly in the latter stages of the reaction due to acyl migration. System 2 was the system most easily adaptable to a large-scale process, making it the method of choice. For System 2 reactions, only when the medium was initially saturated with water and water consumed by the reaction was continuously replaced could 30–40% hydrolysis be achieved. External mass transfer limitations for Lipozyme-catalyzed reactions were not present when the solution’s water content was not above saturation, and its kinematic viscosity, controlled by the temperature and the proportion of isooctane, was below 41 centistokes.