glycidylation

Glycidylation is a chemical process by which a glycidyl group, the epoxypropyl moiety, is introduced into a molecule. Common glycidyl donors include glycidyl chloride and epichlorohydrin, which are used to convert alcohols, phenols, and amines into glycidyl ethers or N-glycidyl derivatives.

In typical glycidylation reactions, a nucleophile such as an alkoxide, phenoxide, or amine attacks the electrophilic carbon of the glycidyl reagent in an SN2-type reaction. The epoxy (epoxide) ring is usually preserved during this bond-forming step, providing a reactive three-membered ring in the product. Glycidylation of alcohols or phenols yields glycidyl ethers, while amines give N-glycidyl derivatives. The resulting compounds contain an epoxy group that can participate in subsequent chemistry, such as ring opening or crosslinking.

Applications of glycidylated compounds are broad. They are key intermediates in the production of epoxy resins, coatings, and adhesives, where the glycidyl (epoxy) functionality enables curing with hardeners or acids. Glycidylated natural products and biomolecules are studied to introduce epoxy sites for polymer conjugation or material-functionalization. Glycidylation also serves in polymer chemistry to tailor reactivity and crosslinking density.

Considerations for glycidylation include the nucleophile’s strength and sterics, the choice of glycidyl donor, solvent, and temperature, all of which influence yield and selectivity. Safety concerns arise from the reactive epoxide group and from handling glycidyl reagents, which can be hazardous and irritant.