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Wood Research and Technology


Cellulose – Hemicelluloses – Lignin – Wood Extractives

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Kraft lignin reaction with paraformaldehyde

Hanna Paananen
  • Department of Chemistry, University of Eastern Finland, P.O. Box 111, FI-80101 Joensuu, Finland
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Tuula T. Pakkanen
  • Corresponding author
  • Department of Chemistry, University of Eastern Finland, P.O. Box 111, FI-80101 Joensuu, Finland
  • Email
  • Other articles by this author:
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Published Online: 2019-12-13 | DOI: https://doi.org/10.1515/hf-2019-0147


Lignin is the second most abundant biopolymer and will be an important source for carbon-containing compounds in the future. Based on their similar phenolic structures, lignin has great potential to become a valuable substitute for phenol in phenol-formaldehyde resin adhesives. To meet this aim, the sodium hydroxide (NaOH)-catalyzed reaction of kraft lignin with formaldehyde was studied by using paraformaldehyde (PFA) as a formaldehyde source. The advantage of using PFA, the solid polymer of formaldehyde, is the simple composition of the depolymerized solution. According to the results of differential scanning calorimetry (DSC), the lignin reaction was found to require a high NaOH concentration in order for the reaction with PFA to proceed at reasonably low temperatures compared to the curing temperature of phenol-formaldehyde resins (approximately 150°C). On the other hand, high alkalinity conditions are known to favor the disproportionation of formaldehyde to formic acid and methanol. Due to the moderate reactivity of lignin, the Cannizzaro reaction can compete with the methylolation reaction of lignin. Based on the results of 13C, 31P and 1H-13C heteronuclear single quantum correlation nuclear magnetic resonance (HSQC NMR), methylolation was found to be the main reaction occurring in the lignin-formaldehyde reaction.

Keywords: 1H-13C HSQC NMR; differential scanning calorimetry; methylolation of lignin; paraformaldehyde; softwood kraft lignin


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About the article

Received: 2019-05-17

Accepted: 2019-10-18

Published Online: 2019-12-13

Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

Research funding: The Finnish Funding Agency for Technology and Innovation (funder Id: http://dx.doi.org/10.13039/501100003406) and the European Union/European Regional Development Fund are gratefully acknowledged for their financial support within the EVIM project. Furthermore, a scholarship (H.P.) from the University of Eastern Finland (funder Id: http://dx.doi.org/10.13039/100007753) is acknowledged.

Employment or leadership: None declared.

Honorarium: None declared.

Citation Information: Holzforschung, 20190147, ISSN (Online) 1437-434X, ISSN (Print) 0018-3830, DOI: https://doi.org/10.1515/hf-2019-0147.

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