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Valorisation of organosolv lignin in dynamic boronate ester gels by ethanol/water tandem batch depolymerization and exploiting glycerol carbonate functionalization

Bram Jacobs (UGent) , Matteo Deroma (UGent) , Ine Van Nieuwenhove (UGent) , Pablo Reyes Isaacura (UGent) , Dagmar D'hooge (UGent) , Geert-Jan Graulus, Katrien V. Bernaerts and An Verberckmoes (UGent)
(2026) REACTIVE & FUNCTIONAL POLYMERS. 222.
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Abstract
In this study, a tandem process combining depolymerization and oxyalkylation was applied to beech organosolv lignin (MW approximate to 8300 g mol-1) to synthesize an optimal 1,2-diol rich bio-based substrate for boronate ester gels. A 70/30 vol% ethanol/water solvent system was selected as depolymerization medium due to its optimal lignin solubility and depolymerization degree. The depolymerization was conducted at 250 degrees C for 8 h and yielded lignin products with tuneable molecular weights (MW approximate to 2100-5900 g mol-1), influenced by the presence of Pd-catalyst and/or formic acid. The phenolic OH content increased across all samples through cleavage of beta-O-4 linkages to similar values of approximate to 4.0-4.5 mmol g- 1, particularly in condensed phenolic OHs due to the high S/G ratio. The aliphatic OH content decreased by acid-catalysed depolymerization while the addition of the Pd-catalyst mitigated this effect via in-situ H2 generation. Subsequent oxyalkylation with glycerol carbonate at 175 degrees C for 30 min, catalysed by K2CO3, converted phenolic OHs into 1,2-diols. The increase in alOH content is affected by the initial ratio of different OH functionalities and by the unwanted internal transesterification that led to discrepancies between theoretical values and experimental results. Finally, boronate ester gels with stoichiometric diol/ boronic acid ratio were made and 1,2-diol quantification via 13C NMR proved more accurate than 31P NMR, which overestimated the 1,2-diol content, leading to excessive crosslinker addition and consequently diol capping. Despite a lower 1,2-diol content, gels from depolymerized lignin exhibited higher storage and loss moduli, attributed to the increased effective crosslink density.
Keywords
Lignin, Reductive depolymerization, Oxyalkylation, 2-diols, Boronate ester gels

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MLA
Jacobs, Bram, et al. “Valorisation of Organosolv Lignin in Dynamic Boronate Ester Gels by Ethanol/Water Tandem Batch Depolymerization and Exploiting Glycerol Carbonate Functionalization.” REACTIVE & FUNCTIONAL POLYMERS, vol. 222, 2026, doi:10.1016/j.reactfunctpolym.2026.106685.
APA
Jacobs, B., Deroma, M., Van Nieuwenhove, I., Reyes Isaacura, P., D’hooge, D., Graulus, G.-J., … Verberckmoes, A. (2026). Valorisation of organosolv lignin in dynamic boronate ester gels by ethanol/water tandem batch depolymerization and exploiting glycerol carbonate functionalization. REACTIVE & FUNCTIONAL POLYMERS, 222. https://doi.org/10.1016/j.reactfunctpolym.2026.106685
Chicago author-date
Jacobs, Bram, Matteo Deroma, Ine Van Nieuwenhove, Pablo Reyes Isaacura, Dagmar D’hooge, Geert-Jan Graulus, Katrien V. Bernaerts, and An Verberckmoes. 2026. “Valorisation of Organosolv Lignin in Dynamic Boronate Ester Gels by Ethanol/Water Tandem Batch Depolymerization and Exploiting Glycerol Carbonate Functionalization.” REACTIVE & FUNCTIONAL POLYMERS 222. https://doi.org/10.1016/j.reactfunctpolym.2026.106685.
Chicago author-date (all authors)
Jacobs, Bram, Matteo Deroma, Ine Van Nieuwenhove, Pablo Reyes Isaacura, Dagmar D’hooge, Geert-Jan Graulus, Katrien V. Bernaerts, and An Verberckmoes. 2026. “Valorisation of Organosolv Lignin in Dynamic Boronate Ester Gels by Ethanol/Water Tandem Batch Depolymerization and Exploiting Glycerol Carbonate Functionalization.” REACTIVE & FUNCTIONAL POLYMERS 222. doi:10.1016/j.reactfunctpolym.2026.106685.
Vancouver
1.
Jacobs B, Deroma M, Van Nieuwenhove I, Reyes Isaacura P, D’hooge D, Graulus G-J, et al. Valorisation of organosolv lignin in dynamic boronate ester gels by ethanol/water tandem batch depolymerization and exploiting glycerol carbonate functionalization. REACTIVE & FUNCTIONAL POLYMERS. 2026;222.
IEEE
[1]
B. Jacobs et al., “Valorisation of organosolv lignin in dynamic boronate ester gels by ethanol/water tandem batch depolymerization and exploiting glycerol carbonate functionalization,” REACTIVE & FUNCTIONAL POLYMERS, vol. 222, 2026.
@article{01KH75BVN7CFZ5GRJVRKNGVZ5M,
  abstract     = {{In this study, a tandem process combining depolymerization and oxyalkylation was applied to beech organosolv lignin (MW approximate to 8300 g mol-1) to synthesize an optimal 1,2-diol rich bio-based substrate for boronate ester gels. A 70/30 vol% ethanol/water solvent system was selected as depolymerization medium due to its optimal lignin solubility and depolymerization degree. The depolymerization was conducted at 250 degrees C for 8 h and yielded lignin products with tuneable molecular weights (MW approximate to 2100-5900 g mol-1), influenced by the presence of Pd-catalyst and/or formic acid. The phenolic OH content increased across all samples through cleavage of beta-O-4 linkages to similar values of approximate to 4.0-4.5 mmol g- 1, particularly in condensed phenolic OHs due to the high S/G ratio. The aliphatic OH content decreased by acid-catalysed depolymerization while the addition of the Pd-catalyst mitigated this effect via in-situ H2 generation. Subsequent oxyalkylation with glycerol carbonate at 175 degrees C for 30 min, catalysed by K2CO3, converted phenolic OHs into 1,2-diols. The increase in alOH content is affected by the initial ratio of different OH functionalities and by the unwanted internal transesterification that led to discrepancies between theoretical values and experimental results. Finally, boronate ester gels with stoichiometric diol/ boronic acid ratio were made and 1,2-diol quantification via 13C NMR proved more accurate than 31P NMR, which overestimated the 1,2-diol content, leading to excessive crosslinker addition and consequently diol capping. Despite a lower 1,2-diol content, gels from depolymerized lignin exhibited higher storage and loss moduli, attributed to the increased effective crosslink density.}},
  articleno    = {{106685}},
  author       = {{Jacobs, Bram and Deroma, Matteo and Van Nieuwenhove, Ine and Reyes Isaacura, Pablo and D'hooge, Dagmar and Graulus, Geert-Jan and Bernaerts, Katrien V. and Verberckmoes, An}},
  issn         = {{1381-5148}},
  journal      = {{REACTIVE & FUNCTIONAL POLYMERS}},
  keywords     = {{Lignin,Reductive depolymerization,Oxyalkylation,2-diols,Boronate ester gels}},
  language     = {{eng}},
  pages        = {{12}},
  title        = {{Valorisation of organosolv lignin in dynamic boronate ester gels by ethanol/water tandem batch depolymerization and exploiting glycerol carbonate functionalization}},
  url          = {{http://doi.org/10.1016/j.reactfunctpolym.2026.106685}},
  volume       = {{222}},
  year         = {{2026}},
}
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