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

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.