Organic and bioorganic reactions in microemulsions

Abstract

During the last two decades reactions in microemulsions have developed into an emerging technology. In most instances oil-continuous microemulsions (w/o systems) have been used and the water droplets have proven useful as “minireactors” for various types of syntheses. This review discusses recent advances in the fields of organic and bioorganic reactions in microemulsions. In preparative organic synthesis microemulsions are of interest to overcome incompatibility problems between nonpolar organic compounds and inorganic salts. For this purpose, microemulsions can be regarded as an alternative to two-phase systems with added phase transfer reagents. Properly formulated microemulsions may also accelerate organic reactions, various mechanisms of such rate enhancements are discussed. Transition from a homogeneous solvent system to a microemulsion may also affect the regioselectivity of organic reactions due to orientation of reactants at the oil-water interface. In bioorganic synthesis, microemulsions are of interest as a reaction medium for several reasons: (i) nonpolar substrates can be dissolved in high concentrations, (ii) thermodynamic equilibria of condensation/hydrolysis reactions can be shifted by adjusting water content, (iii) enzymes are sometimes found to be more stable and more active than in aqueous buffer. Lipases are the most widely used enzymes and reactions have been performed in different types of microemulsion systems. This review presents general aspects of enzymatic catalysis in microemulsions followed by a discussion of recent advances in preparative work focusing on lipase catalyzed processes.