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Identification and quantification of lignin monomers and oligomers from reductive catalytic fractionation of pine wood with GC × GC – FID/MS

(2022) GREEN CHEMISTRY. 24(1). p.191-206
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Abstract
Comprehensive HT-GC × GC FID/MS enables reliable detection and quantification of RCF lignin monomers, dimers and, trimers.
Thorough lignin characterization is vital to understand the physicochemical properties of lignin and to evaluate lignocellulose biorefinery processes. In this study, an in-depth characterization of lignin oil, obtained from reductive catalytic fractionation (RCF) of pine wood, was performed with quantitative GC x GC - FID analysis and qualitative GC x GC - MS. By utilizing high-temperature resistant column sets in the GC x GC system and by applying a derivatization step, unambiguous detection of lignin monomers, dimers, and trimers is enabled. In addition to confirm the identity of eleven monomers, corresponding to 34 wt% of the RCF lignin oil, thirty-six dimers (16 wt%) and twenty-one trimers (7 wt%) were comprehensively identified by analysis of their mass spectra and quantified by a FID, encompassing the identity of an additional 23 wt% of the RCF lignin oil. The proposed structures reveal the interlinkages present in the dimeric and trimeric oligomers, containing beta-5, beta-1, beta-beta, 5-5, and a minor fraction of beta-O-4 and 4-O-5 bonds. Furthermore, aliphatic end-units in the dimeric and trimeric molecules were identified, consisting of various substituents at the C4 position, that have been previously observed in the RCF-derived lignin monomers. To reduce complexity for analysis, the RCF oil was separated into six fractions, prior to analysis. The structural motifs (inter-unit linkages and end-units) that are found in the different fractions vary significantly, such that the lignin fractions extracted in more polar solvents contained higher molecular weight fragments and more hydroxyl containing structural motifs. The identified structures of individual dimer and trimer molecules by GC x GC align well with and further complement the recent findings from H-1-C-13 HSQC NMR spectroscopy, demonstrating complementarity between both 2D techniques to obtain a holistic view on both the molecular structures and the distribution of bonds and end-units in RCF oil. The combination of these two techniques provides a powerful tool for future RCF and other lignin depolymerization research.
Keywords
Pollution, Environmental Chemistry, 2-DIMENSIONAL GAS-CHROMATOGRAPHY, TANDEM MASS-SPECTROMETRY, KRAFT LIGNIN, BIO-OILS, LIGNOCELLULOSE FRACTIONATION, FAST PYROLYSIS, RESPONSE FACTORS, SOLUBLE LIGNIN, DIMERS, DEPOLYMERIZATION

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MLA
Dao Thi, Hang, et al. “Identification and Quantification of Lignin Monomers and Oligomers from Reductive Catalytic Fractionation of Pine Wood with GC × GC – FID/MS.” GREEN CHEMISTRY, vol. 24, no. 1, 2022, pp. 191–206, doi:10.1039/d1gc03822b.
APA
Dao Thi, H., Van Aelst, K., Van den Bosch, S., Katahira, R., Beckham, G. T., Sels, B. F., & Van Geem, K. (2022). Identification and quantification of lignin monomers and oligomers from reductive catalytic fractionation of pine wood with GC × GC – FID/MS. GREEN CHEMISTRY, 24(1), 191–206. https://doi.org/10.1039/d1gc03822b
Chicago author-date
Dao Thi, Hang, Korneel Van Aelst, Sander Van den Bosch, Rui Katahira, Gregg T. Beckham, Bert F. Sels, and Kevin Van Geem. 2022. “Identification and Quantification of Lignin Monomers and Oligomers from Reductive Catalytic Fractionation of Pine Wood with GC × GC – FID/MS.” GREEN CHEMISTRY 24 (1): 191–206. https://doi.org/10.1039/d1gc03822b.
Chicago author-date (all authors)
Dao Thi, Hang, Korneel Van Aelst, Sander Van den Bosch, Rui Katahira, Gregg T. Beckham, Bert F. Sels, and Kevin Van Geem. 2022. “Identification and Quantification of Lignin Monomers and Oligomers from Reductive Catalytic Fractionation of Pine Wood with GC × GC – FID/MS.” GREEN CHEMISTRY 24 (1): 191–206. doi:10.1039/d1gc03822b.
Vancouver
1.
Dao Thi H, Van Aelst K, Van den Bosch S, Katahira R, Beckham GT, Sels BF, et al. Identification and quantification of lignin monomers and oligomers from reductive catalytic fractionation of pine wood with GC × GC – FID/MS. GREEN CHEMISTRY. 2022;24(1):191–206.
IEEE
[1]
H. Dao Thi et al., “Identification and quantification of lignin monomers and oligomers from reductive catalytic fractionation of pine wood with GC × GC – FID/MS,” GREEN CHEMISTRY, vol. 24, no. 1, pp. 191–206, 2022.
@article{8741605,
  abstract     = {{Comprehensive HT-GC × GC FID/MS enables reliable detection and quantification of RCF lignin monomers, dimers and, trimers.}},
  author       = {{Dao Thi, Hang and Van Aelst, Korneel and Van den Bosch, Sander and Katahira, Rui and Beckham, Gregg T. and Sels, Bert F. and Van Geem, Kevin}},
  issn         = {{1463-9262}},
  journal      = {{GREEN CHEMISTRY}},
  keywords     = {{Pollution,Environmental Chemistry,2-DIMENSIONAL GAS-CHROMATOGRAPHY,TANDEM MASS-SPECTROMETRY,KRAFT LIGNIN,BIO-OILS,LIGNOCELLULOSE FRACTIONATION,FAST PYROLYSIS,RESPONSE FACTORS,SOLUBLE LIGNIN,DIMERS,DEPOLYMERIZATION}},
  language     = {{eng}},
  number       = {{1}},
  pages        = {{191--206}},
  title        = {{Identification and quantification of lignin monomers and oligomers from reductive catalytic fractionation of pine wood with GC × GC – FID/MS}},
  url          = {{http://dx.doi.org/10.1039/d1gc03822b}},
  volume       = {{24}},
  year         = {{2022}},
}

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