Study of the O-glycidylation of natural phenolic compounds. The relationship between the phenolic structure and the reaction mechanism

The O-alkylation reaction by epichlorohydrin of some natural phenolic compounds such as 4-methylcatechol, gallic acid, protocatechuic acid, pyrogallol and resorcinol was investigated. Phenolic compounds reacted first with epichlorohydrin in the presence of benzyltriethylammonium chloride as phase transfer catalyst. Then, an aqueous solution of sodium hydroxide was added.It was demonstrated that the two competitive mechanisms involved in the O-alkylation reaction were highly dependent of the starting material. The O-alkylated products obtained in this reaction could be further used as bisphenol A substitutes in the synthesis of epoxy resins pre-polymers.

In the aim to synthetize bio-based epoxy resin pre-polymers, the O-glycidylation reaction of several natural phenolic compounds has been achieved, in the presence of phase transfer catalyst. It has been shown that the reactivity of these phenolic compounds is highly influenced by their chemical structure.