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Staff Publications

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    'Staff publications' is the digital repository of Wageningen University & Research

    'Staff publications' contains references to publications authored by Wageningen University staff from 1976 onward.

    Publications authored by the staff of the Research Institutes are available from 1995 onwards.

    Full text documents are added when available. The database is updated daily and currently holds about 240,000 items, of which 72,000 in open access.

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Record number 499632
Title Lipase-catalyzed synthesis of oligoesters of 2,5-furandicarboxylic acid with aliphatic diols
Author(s) Cruz-Izquierdo, Álvaro; Broek, Lambertus A.M. van den; Serra, Juan L.; Llama, María J.; Boeriu, Carmen G.
Source Pure and Applied Chemistry 87 (2015)1. - ISSN 0033-4545 - p. 59 - 69.
Department(s) FBR BP Biorefinery & Sustainable Value Chains
FBR Sustainable Chemistry & Technology
Publication type Refereed Article in a scientific journal
Publication year 2015
Keyword(s) 2,5-furandicarboxylic acid - Bioplastics - Enzymatic polymerization - Lipase - Oligoesters - POC-2014

2,5-Furandicarboxylic acid is a platform chemical for the production of biobased polymers and materials. This study reports the synthesis of furan oligoesters via polytransesterification of dimethyl furan-2,5-dicarboxylate and linear α, ω-aliphatic diols with chain length ranging from C2 to C12, using immobilized lipase B from Candida antarctica (Novozym 435) in dry organic solvents. Dimethyl furan-2,5-dicarboxylic acid (A) and 1,4-butanediol (B) were used as model substrates under different conditions producing a mixture of cyclic (CEOs) and linear (LEOs) ester oligomers up to decamers and dodecamers, respectively, with high yield. The size of the oligomers and distribution of the products is controlled by the initial concentration of substrates and temperature. While the shortest CEOs are the main cyclic compounds at 20 mM, the longest CEOs are formed at 175 mM. The chain length of the aliphatic diol co-monomers strongly influences the yield and the type of oligoesters formed. High substrate conversion of 90-95% was obtained for C4-C12 diols, while in the case of ethylene glycol and 1,3-propanediol the conversion was moderate (i.e., 75%). The product of the reaction between dimethyl furan-2,5-dicarboxylate and ethylene glycol (C2) and 1,3-propanediol (C3), respectively, consisted only of linear oligoesters. Longer oligoesters were obtained for alkyl chains higher than C4. The chain length and the abundance of oligoesters increases in the order: C2<C12<C10<C3<C8<C4 <C6. No substrate or product inhibition was observed in the production of furan-based oligoesters. The present biobased oligoesters are obtained via a green process and have potential application as macromonomers.

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