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

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...

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Bibliographic Details
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
Description
Summary: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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