Within the framework of enzymatic biosurfactant synthesis, the development of reaction processes leading to a selective and efficient production is of crucial interest. In this work, we proposed an enzymatic method for producing 1(3)-monooleoyl-rac-glycerol using a commercial immobilized lipase, the Lipozyme®. To avoid the blockage of the enzyme by the presence of insoluble glycerol, the latter was adsorbed onto dried silica gel. The selective monoester production (83%) was obtained using 2-methyl-2-butanol amended n-hexane (90:10, vol/vol) as reaction medium. The observed decrease in the substrate conversion, in a medium containing 2-methyl-2-butanol, was countered by coupling to the reaction an inline selective recovery method for the produced monoester by adsorption onto a silica gel column located at the outflow of the reaction vessel. This process leads to an efficient monooleoyl glycerol production with a high oleic acid conversion (71%) and to the recovery of a 100% pure monooleoyl glycerol.