Chemo-enzymatic functionalization of gallic and vanillic acids: synthesis of bio-based epoxy resins prepolymers
2012
Aouf, Chahinez | Lecomte, Jérôme | Villeneuve, Pierre | Dubreucq, Eric | Fulcrand, Hélène
The chemo-enzymatic epoxidation of allylated gallic and vanillic acids with lipase B from Candida antarctica and aqueous hydrogen peroxide in the presence of caprylic acid was investigated. The use of 1 molar eq of caprylic acid and 1.8–2 molar eq of H₂O₂ per allylic double bond led to a high degree of conversion to epoxides (89% yield for allylated gallic acid and 87% yield for allylated vanillic acid) comparatively to the hazardous peracid mCPBA (1.5–3.2 molar eq per double bond allowed 75–85% yield). The epoxidized products obtained could be used in the formulation of novel bio-based epoxy resins.
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