Levoglucosenone-derived synthesis of bio-based solvents and polyesters

TY - JOUR

T1 - Levoglucosenone-derived synthesis of bio-based solvents and polyesters

AU - Warne, Cicely M.

AU - Fadlallah, Sami

AU - Whitwood, Adrian C.

AU - Sherwood, James

AU - Mouterde, Louis M.M.

AU - Allais, Florent

AU - Guebitz, Georg M.

AU - McElroy, Con R.

AU - Pellis, Alessandro

N1 - Funding Information: This work is supported by European Union’s Horizon 2020 research and innovation programme under grant agreement No 953073, project UPLIFT (sUstainable PLastIcs for the Food and drink packaging indusTry). LMMM, SF and FA are grateful to Grand Reims, Département de la Marne and Région Grand Est for financial support. Thanks to Mr Karl Heaton of the Mass Spectrometry Service, Department of Chemistry, University of York for obtaining ESI data. Publisher Copyright: © 2022 The Author(s). Published by Informa UK Limited, trading as Taylor & Francis Group.

PY - 2022/12/30

Y1 - 2022/12/30

N2 - Polyesters are important materials with a wide range of applications, but there has been increasing concern over their sustainability. One example is the need for safer, bio-derived solvents to replace those currently in use for the polymer’s synthesis and processing. In this work, several variants of the bio-based cellulose/levoglucosenone derived solvent Cyrene, namely the ketal derivatives dioxolane Cygnet, dioxane Cygnet and dioxepane Cygnet were synthesized and tested as media for enzymatic polycondensation reactions using bio-based building blocks. Dioxolane Cygnet and dioxepane Cygnet were found to be suitable solvents for enzymatic polycondensation reactions, with dioxolane Cygnet being the preferred solvent, yielding polymers with a Mn >22 kDa. In addition, these solvents were tested in the biocatalyzed synthesis of levoglucosenone-based polyesters. The alternative solvents gave superior yields to those previously observed, demonstrating the versatility of these solvents in enzymatic polycondensation reactions, representing the first synthetic polymer-solvent system fully derived from cellulose.

AB - Polyesters are important materials with a wide range of applications, but there has been increasing concern over their sustainability. One example is the need for safer, bio-derived solvents to replace those currently in use for the polymer’s synthesis and processing. In this work, several variants of the bio-based cellulose/levoglucosenone derived solvent Cyrene, namely the ketal derivatives dioxolane Cygnet, dioxane Cygnet and dioxepane Cygnet were synthesized and tested as media for enzymatic polycondensation reactions using bio-based building blocks. Dioxolane Cygnet and dioxepane Cygnet were found to be suitable solvents for enzymatic polycondensation reactions, with dioxolane Cygnet being the preferred solvent, yielding polymers with a Mn >22 kDa. In addition, these solvents were tested in the biocatalyzed synthesis of levoglucosenone-based polyesters. The alternative solvents gave superior yields to those previously observed, demonstrating the versatility of these solvents in enzymatic polycondensation reactions, representing the first synthetic polymer-solvent system fully derived from cellulose.

KW - enzymatic catalysis

KW - green polymer chemistry

KW - green solvents

KW - Sustainable polyesters

UR - http://www.scopus.com/inward/record.url?scp=85148441625&partnerID=8YFLogxK

U2 - 10.1080/17518253.2022.2154573

DO - 10.1080/17518253.2022.2154573

M3 - Article

AN - SCOPUS:85148441625

SN - 1751-8253

VL - 16

JO - Green Chemistry Letters and Reviews

JF - Green Chemistry Letters and Reviews

IS - 1

M1 - 2154573

ER -