Enzymatic Synthesis of Thioesters in Non-conventional Solvents

The feasibility of enzymatic thioesterification between oleic acid and butanethiol in n-hexane, with the immobilised lipase (Lipozyme) from Mucor miehei, has been demonstrated. The immobilised enzyme quantity (100 mg), temperature (40°C), pH range (6–9) and water content (10%) were studied and their optimum values were determined. A preliminary kinetic study indicated a low butanethiol affinity for the enzyme (K_m = 1·85 mol dm⁻³). Even when butanethiol was used without solvent, no substrate inhibition was observed. The possibility of carrying out this reaction in a natural solvent, supercritical carbon dioxide (SCCO₂), was successfully verified. After 8 h reaction, a conversion yield of oleic acid of about 33% was obtained. © 1997 SCI.