Organic Reactions i Organised Media

Doctoral thesis, 2007

A common problem in synthetic organic chemistry is reactant incompatibility between lipophilic organic compounds and inorganic salts. The thesis reports an investigation of some organic reactions, involving incompatible substrate and nucleophile, performed in liquid crystalline phases and also in slurries of mesoporous materials with different symmetry. In such media, the reaction occurs at the hydrophilic/lipophilic interface, and, because the interface is large, the reaction is fast. A considerable advantage with the use of slurries of mesoporous materials, as reaction media is that the workup procedure is extremely facile. After the reaction is completed, the solid is simply removed by filtering or centrifugation. The mesoporous materials, as well as the different self-assemblies, such as surfactant liquid crystals and microemulsions, can be seen as minireactors for organic reactions. Different mesoporous materials were also used as host for a lipase and the enzyme-loaded particles were employed as catalyst for esterification of caprylic acid using a mixture of glycerol and water as reaction medium. Mesoporous materials loaded with cross-linked lipase can be reused several times with only marginal loss of activity.