Novel mannitol based non-ionic surfactants from biocatalysis: Part two: improved synthesis

The 1-O-lauroyl-d-mannitol, a non-ionic surfactant, was synthesised via a chemo-enzymatic pathway starting from the 1,2:4,5-di-O-isopropylidene-d-mannitol and vinyl laurate as acylation agent. The high hydrophobicity of the substrates allowed the enzymatic reaction to occur both in n-hexane and in solvent free conditions. The immobilised Candida antarctica lipase B was used as the catalyst of the enzymatic step. This enzyme acts differently depending on the position of the hydroxyls with respect to the isopropylidene groups. The acid selective hydrolysis of the isopropylidene groups gave the non-ionic surfactant without the presence of isomers.