Chemo-enzymatic preparation of new bio-based bis-and trisphenols: new versatile building blocks for polymer chemistry

• Published in: RSC Advances
• Main Authors: Pion, Florian, F., Reano, Armando, Félix, A. F., Ducrot, Paul Henri, P. H., Allais, Florent, F.
• Other Authors: Institut Jean-Pierre Bourgin (IJPB), Institut National de la Recherche Agronomique (INRA)-AgroParisTech, Region Ile-de-France
• Format: Article in Journal/Newspaper
• Language: English
• Published: HAL CCSD 2013
• Subjects: LIPASE-CATALYZED SYNTHESIS; ORGANIC-SOLVENT MEDIA; PHENOLIC-ACIDS; FERULIC ACID; ANTIOXIDANT ACTIVITY; RENEWABLE RESOURCES; ENZYMATIC-SYNTHESIS; CANDIDA-ANTARCTICA; ESTERIFICATION; TRANSESTERIFICATION; [SDV.SA]Life Sciences [q-bio]/Agricultural sciences; Antarc*; Antarctica; antartic*
• Online Access: https://hal.science/hal-01004482; https://doi.org/10.1039/c3ra41247d

Immobilized Candida antartica lipase B (aka CAL-B) was used to perform solvent-free and in solvent transesterifications of a derivative from ferulic acid (1), ethyl dihydroferulate (2), with various bio-based polyols (isosorbide, 1,3-propanediol, 1,4-butanediol and glycerol). The use of 1.5 molar eq of ethyl dihydroferulate (2) per alcohol functionality and CAL-B (10% by weight relative to the total weight of polyol and 2) led to the corresponding poly-ferulates (3-6) in very good yields and high purity. These polyferulates were then efficiently transformed through one-step processes into the corresponding acrylates (7-10) and allyl ethers (11-14) to demonstrate their potential use as biorenewable macromonomers in a wide range of polymerization systems.