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

• Published in: Green Chemistry
• Main Authors: Aouf, Chahinaz, Lecomte, Jerome, Villeneuve, Pierre, Dubreucq, Eric, Fulcrand-Hoh, Helene
• Other Authors: Sciences Pour l'Oenologie (SPO), Université Montpellier 1 (UM1)-Institut National de la Recherche Agronomique (INRA)-Université de Montpellier (UM)-Institut national d’études supérieures agronomiques de Montpellier (Montpellier SupAgro), Ingénierie des Agro-polymères et Technologies Émergentes (UMR IATE), Centre de Coopération Internationale en Recherche Agronomique pour le Développement (Cirad)-Institut National de la Recherche Agronomique (INRA)-Université Montpellier 2 - Sciences et Techniques (UM2)-Centre international d'études supérieures en sciences agronomiques (Montpellier SupAgro)-Université de Montpellier (UM)-Institut national d’études supérieures agronomiques de Montpellier (Montpellier SupAgro), department CEPIA (INRA, France)
• Format: Article in Journal/Newspaper
• Language: English
• Published: HAL CCSD 2012
• Subjects: ANTARCTICA LIPASE-B; BISPHENOL-A; PEROXYCARBOXYLIC ACIDS; ENGINEERING PLASTICS; CATALYZED SYNTHESIS; EPOXIDATION; OIL; EXPOSURE; LIGNIN; FEMALE; [SDV]Life Sciences [q-bio]; Antarc*; Antarctica
• Online Access: https://hal.science/hal-01506271; 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.