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Solvent-free lipase-catalyzed synthesis of linear and thermally stable polyesters obtained from diacids and diols

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Abstract

Aliphatic polyesters are widely used in biomedical and environmental areas, and their use has grown due to environmental issues. The use of lipases as catalysts for the synthesis of polyesters is an environmentally benign alternative. In this work, the effect of monomer chain length on polyester synthesis was studied with seven diacids and six diols in a bulk system using immobilized Candida antarctica lipase B (Novozym®435). Firstly, the reaction temperature and the thermal stability of Novozym®435 (N435) were evaluated. The half-life of the commercial lipase was 24.8 h at 90 °C, and N435 maintained a residual activity of 38% after 96 h of incubation. The biocatalyst played an essential role in the reactions using monomers with longer alkylene chain length diacids (azelaic and sebacic acids) and diols (1,4-butanediol, 1,6-hexanediol, and 1,8-octanediol), giving a higher reactivity than reactions of shorter chain-length diacids (oxalic, malonic, succinic, glutaric and adipic acids) and diols (ethylene glycol and 1,3-propanediol). Polycondensation reactions carried out with 2,3-butanediol did not present a significative molecular weight. Otherwise, the reaction performed with 1,6-hexanediol resulted in polyesters with weight-average molecular weights (Mw) of 18,346 g mol−1 and 27,121 g mol−1 by reacting with azelaic and sebacic acids, respectively, at 90 °C using 5 wt.% of N435. The thermal properties of polyazelates and polysebactes were analyzed by DSC and TGA, which showed that aliphatic polyesters are practically stable at up to 380 °C, indicating their high thermal stability.

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Acknowledgements

The authors thank IFRJ, UERJ, Petrobras for funding, and LCPRB/IMA/UFRJ for GPC, TGA, and DSC analysis. The authors declare that they have no conflict of interest.

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  1. Analytical Chemistry Department, Chemistry Institute, Rio de Janeiro State University (UERJ), Rio de Janeiro, Brazil

    Ivone Sampaio Pereira Campisano, Erika de Queiros Eugenio, Cláudia de Oliveira Veloso & Marta Antunes Pereira Langone

  2. Faculty of Technology, Rio de Janeiro State University (UERJ), Rio de Janeiro, Brazil

    Erika de Queiros Eugenio

  3. Institute of Macromolecules Professor Eloisa Mano (IMA), Federal University of Rio de Janeiro (UFRJ), Rio de Janeiro, Brazil

    Marcos Lopes Dias

  4. Biotechnology Division, Research, and Development Center, Petrobras, Rio de Janeiro, Brazil

    Aline Machado de Castro

  5. Federal Institute of Education, Science, and Technology of Rio de Janeiro (IFRJ), Rio de Janeiro, Brazil

    Marta Antunes Pereira Langone

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43153_2021_137_MOESM1_ESM.tif

Supplementary Figure 1: Gel permeation chromatogram of poly(butylene azelate) obtained at 30 °C using tetrahydrofuran as the eluent. Reaction conditions: molar ratio of 1,4-BDO/azelaic acid equal to 1, t = 96 h, T = 90 °C, 5 wt.% of Novozym 435 (TIF 126 KB)

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Campisano, I.S.P., de Queiros Eugenio, E., de Oliveira Veloso, C. et al. Solvent-free lipase-catalyzed synthesis of linear and thermally stable polyesters obtained from diacids and diols. Braz. J. Chem. Eng. 38, 549–562 (2021). https://doi.org/10.1007/s43153-021-00137-y

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