Chemo-enzymatic functionalization of gallic and vanillic acids: synthesis of bio-based epoxy resins prepolymers

• Published in: Green Chemistry
• Main Authors: Aouf, Chabinez, Lecomte, Jérôme, Villeneuve, Pierre, Dubreucq, Eric, Fulcrand, Hélène
• Format: Article in Journal/Newspaper
• Language: English
• Published: 2012
• Subjects: Q60 - Traitement des produits agricoles non alimentaires; 000 - Autres thèmes; Tannin; Acide vanillique; Candida; Biosynthèse; Composé époxy; Biocatalyseur; Composé phénolique; http://aims.fao.org/aos/agrovoc/c_7606; http://aims.fao.org/aos/agrovoc/c_34141; http://aims.fao.org/aos/agrovoc/c_1247; http://aims.fao.org/aos/agrovoc/c_928; http://aims.fao.org/aos/agrovoc/c_36773; http://aims.fao.org/aos/agrovoc/c_27460; http://aims.fao.org/aos/agrovoc/c_5772; Antarc*; Antarctica
• Online Access: http://agritrop.cirad.fr/564874/; http://agritrop.cirad.fr/564874/1/document_564874.pdf; https://doi.org/10.1039/c2gc35558b

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.