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Overcoming the low reactivity of biobased, secondary diols in polyester synthesis

Author

Listed:
  • Daniel H. Weinland

    (University of Amsterdam)

  • Kevin van der Maas

    (University of Amsterdam)

  • Yue Wang

    (University of Amsterdam)

  • Bruno Bottega Pergher

    (University of Amsterdam)

  • Robert-Jan van Putten

    (University of Amsterdam
    Avantium Chemicals BV, Zekeringstraat 29)

  • Bing Wang

    (Avantium Chemicals BV, Zekeringstraat 29)

  • Gert-Jan M. Gruter

    (University of Amsterdam
    Avantium Chemicals BV, Zekeringstraat 29)

Abstract

Shifting away from fossil- to biobased feedstocks is an important step towards a more sustainable materials sector. Isosorbide is a rigid, glucose-derived secondary diol, which has been shown to impart favourable material properties, but its low reactivity has hampered its use in polyester synthesis. Here we report a simple, yet innovative, synthesis strategy to overcome the inherently low reactivity of secondary diols in polyester synthesis. It enables the synthesis of fully biobased polyesters from secondary diols, such as poly(isosorbide succinate), with very high molecular weights (Mn up to 42.8 kg/mol). The addition of an aryl alcohol to diol and diacid monomers was found to lead to the in-situ formation of reactive aryl esters during esterification, which facilitated chain growth during polycondensation to obtain high molecular weight polyesters. This synthesis method is broadly applicable for aliphatic polyesters based on isosorbide and isomannide and could be an important step towards the more general commercial adaption of fully biobased, rigid polyesters.

Suggested Citation

  • Daniel H. Weinland & Kevin van der Maas & Yue Wang & Bruno Bottega Pergher & Robert-Jan van Putten & Bing Wang & Gert-Jan M. Gruter, 2022. "Overcoming the low reactivity of biobased, secondary diols in polyester synthesis," Nature Communications, Nature, vol. 13(1), pages 1-12, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-34840-2
    DOI: 10.1038/s41467-022-34840-2
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    References listed on IDEAS

    as
    1. Yunqing Zhu & Charles Romain & Charlotte K. Williams, 2016. "Sustainable polymers from renewable resources," Nature, Nature, vol. 540(7633), pages 354-362, December.
    2. Manuel Häußler & Marcel Eck & Dario Rothauer & Stefan Mecking, 2021. "Closed-loop recycling of polyethylene-like materials," Nature, Nature, vol. 590(7846), pages 423-427, February.
    3. Seul-A Park & Hyeonyeol Jeon & Hyungjun Kim & Sung-Ho Shin & Seunghwan Choy & Dong Soo Hwang & Jun Mo Koo & Jonggeon Jegal & Sung Yeon Hwang & Jeyoung Park & Dongyeop X. Oh, 2019. "Sustainable and recyclable super engineering thermoplastic from biorenewable monomer," Nature Communications, Nature, vol. 10(1), pages 1-11, December.
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