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Reversible crosslinking of lignin via the furan-maleimide Diels-Alder reaction
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology. KTH, School of Chemical Science and Engineering (CHE), Centres, Wallenberg Wood Science Center. University of Rome, Italy.
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology. KTH, School of Chemical Science and Engineering (CHE), Centres, Wallenberg Wood Science Center.ORCID iD: 0000-0002-8614-6291
2015 (English)In: Green Chemistry, ISSN 1463-9262, E-ISSN 1463-9270, Vol. 17, no 11, 4991-5000 p.Article in journal (Refereed) Published
Abstract [en]

Two distinct functionalization schemes for Kraft lignin (KL) were developed to selectively incorporate furan and/or maleimide motifs as chain ends. The incorporation of furan functionalities was carried out by the selective and quantitative reaction of the lignin's phenolic OH groups with furfuryl glycidyl ether (FGE). Maleimide groups were introduced by esterifying the lignin's aliphatic and phenolic OH groups with 6 maleimidohexanoic acid (6-MHA), offering a high loading despite a somewhat incomplete conversion. Furan-and maleimide-functionalized lignins were subsequently combined to generate crosslinking via the Diels-Alder (DA) [4 + 2] cycloaddition reaction. The formation of the DA adduct was confirmed by H-1 NMR. Under appropriate conditions, the formation of a gel was apparent, which turned back into the liquid state after performing the corresponding retro-DA reaction upon heating to 120 degrees C. This study reveals the significant versatility and potential of the developed strategy for the utilization of lignin-based recyclable networks.

Place, publisher, year, edition, pages
2015. Vol. 17, no 11, 4991-5000 p.
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:kth:diva-177978DOI: 10.1039/c5gc01319dISI: 000364023500013Scopus ID: 2-s2.0-84946208124OAI: oai:DiVA.org:kth-177978DiVA: diva2:875994
Note

QC 20151202

Available from: 2015-12-02 Created: 2015-11-30 Last updated: 2017-12-01Bibliographically approved

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