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Abstract
The diep-oxy monomer, C13H16O4 {DGE-Eu; systematic name: 2-[3-meth-oxy-4-(oxiran-2-ylmeth-oxy)benz-yl]oxirane}, was synthesized from eugenol by a three-step reaction. It consists of a 1,2,4-tris-ubstituted benzene ring substituted by diglycidyl ether, a meth-oxy group and a methyl-oxirane group. The three-membered oxirane rings are inclined to the benzene ring by 61.0 (3) and 27.9 (3)°. The methyl-ene 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, mol-ecules are linked by C-H⋯O hydrogen bonds, forming layers parallel to the ab plane. The layers are linked by C-H⋯π inter-actions, forming a three-dimensional network.
Highlights
In the specific domain of epoxy thermosets, numerous studies have been conducted in order to find alternatives to the diglycidyl ether of bisphenol A (BADGE), which is the main building-block used for formulation resins (Auvergne et al, 2014)
The synthetic approach is based on the functionalization of bio-sourced molecules by the grafting of glycidyl ether groups. In this context and in our ongoing studies on the chemical modification of bio-based building blocks for material applications (Mhanna et al, 2014; Bigot et al, 2016; François et al, 2016), we report on the synthesis and crystal structure of the diglycidyl ether of eugenol (DGE-Eu), prepared from eugenol in a three-step synthesis (Qin et al, 2014)
It is composed of a benzene ring with three oxygenated functional groups: (i) 2-[(1oxidanyl)methyl]oxirane, (ii) methoxy and (iii) 2-methyloxirane
Summary
The past two decades have witnessed an increasing interest in the environmental quest for the replacement of petroleumbased chemicals by monomers from renewable resources. Advances in particular in the catalytic conversion of biomass have led to a wide range of useful platform molecules (Besson et al, 2014) This sustainable approach is strongly considered in the field of polymer synthesis (Gandini et al., 2016). The synthetic approach is based on the functionalization of bio-sourced molecules by the grafting of glycidyl ether groups. In this context and in our ongoing studies on the chemical modification of bio-based building blocks for material applications (Mhanna et al, 2014; Bigot et al, 2016; François et al, 2016), we report on the synthesis and crystal structure of the diglycidyl ether of eugenol (DGE-Eu), prepared from eugenol in a three-step synthesis (Qin et al, 2014).
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Schedule a callMore From: Acta crystallographica. Section E, Crystallographic communications
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