Understanding glycidylation reaction for the formation of pure mono, diglycidyl and dual monomers as glycidyl methacrylate of vanillyl alcohol

Abstract

The mono epoxy methacrylate and the diepoxy of vanillyl alcohol (DGEVA) are products already known and reported in literature. However, their respective synthesis processes lead to mixtures of products and side-products. Hence, the final reaction yields are low, mainly due to the purification steps. The mixture of by-products obtained is due to the presence of phenol and methylol in raw vanillin. In this article, we have proposed selective synthesis methods avoiding the formation of these by-products, which allows to consider the industrialization of these synthetic routes. Thanks to the difference in reactivity and the basicity of the catalysts used, we were able either to propose a twostep synthesis of the mono-epoxy vanilin, or to epoxidize the two hydroxyl groups to obtain the diepoxy in a single step. Finally, a toxicology study of pure vanillyl alcohol and pure DGEVA was carried out to demonstrate the interest of vanillyl alcohol as a potential substituent of bisphenol A.