Crystal structure of the diglycidyl ether of eugenol

Abstract

The diepoxy monomer, C13H16O4 {DGE-Eu; systematic name: 2-[3-methoxy-4-(oxiran-2-ylmethoxy)benzyl]oxirane}, was synthesized from eugenol by a three-step reaction. It consists of a 1,2,4-trisubstituted benzene ring substituted by diglycidyl ether, a methoxy group and a methyloxirane group. The three-membered oxirane rings are inclined to the benzene ring by 61.0 (3) and 27.9 (3)°. The methylene C atom of one of the two terminal epoxide rings is positionally disordered [refined occupancy ratio = 0.69 (1):0.31 (1)]. In the crystal, molecules are linked by C—H...O hydrogen bonds, forming layers parallel to the ab plane. The layers are linked by C—H...π interactions, forming a three-dimensional network.

Keywords

• crystal structure
• oxirane
• bio-based molecule
• eugenol derivative
• epoxy thermoset prepolymer
• hydrogen bonding