Kraft lignin reaction with paraformaldehyde

Hanna Paananen; Tuula T. Pakkanen

doi:10.1515/hf-2019-0147

Article

Kraft lignin reaction with paraformaldehyde

Hanna Paananen and Tuula T. Pakkanen

Published/Copyright: December 13, 2019

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From the journal Holzforschung Volume 74 Issue 7

Abstract

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

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.

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Received: 2019-05-17

Accepted: 2019-10-18

Published Online: 2019-12-13

Published in Print: 2020-07-28

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https://doi.org/10.1515/hf-2019-0147

Keywords for this article

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