Linear and cyclic ester Oligomers of succinic acid and 1,4-butanediol: Biocatalytic synthesis and characterization

• Published in: Biocatalysis and Biotransformation
• Main Authors: Habeych Narvaez, D.I., Eggink, G., Boeriu, C.G.
• Format: Article in Journal/Newspaper
• Language: English
• Published: 2011
• Subjects: aliphatic polyesters; diethylene glycol; enzyme-catalyzed synthesis; epsilon-caprolactone; equilibrium; organic media; poly(butylene succinate); polyesterification; ring-opening polymerization; Antarc*; Antarctica
• Online Access: https://research.wur.nl/en/publications/linear-and-cyclic-ester-oligomers-of-succinic-acid-and-14-butaned; https://doi.org/10.3109/10242422.2011.632478

The lipase-catalyzed synthesis of cyclic ester oligomers from non-activated succinic acid (A) and 1,4-butanediol (B) in the presence of immobilized Candida antarctica lipase B was investigated. Batch and pulse fed-batch systems were implemented to increase the formation of cyclic ester products. The substrate conversions after 24 h were 86% and 95% under batch and fed-batch operation, respectively and the product of the reaction was, for both systems, a mixture of cyclic (CEOs) and linear (LEOs) ester oligomers. Fed-batch operation afforded a product containing 71% cyclic ester oligomers (CEOs) as compared with only 52% CEOs in batch operation. Cyclic ester oligomers accumulated as the reaction progressed, with the dimer CEO1 the most predominant product (i.e. 50% of the total products formed in fed-batch operation). The pulse fed-batch operation system was superior to the batch operation not only because higher substrate conversion and more CEOs were obtained, but also because it resulted in products with a higher degree of polymerization (DP up to 7). Cyclic ester oligomers are produced from the early stage of the reaction simultaneously with the linear ester oligomers by a ring-closure reaction on the active site of the enzyme, and not as a result of ring-chain equilibria