Study of the Reactivity of Lignin Model Compounds to Fluorobenzylation Using 13C and 19F NMR: Application to Lignin Phenolic Hydroxyl Group Quantification by 19F NMR.

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Esakkiammal Sudha EsakkimuthuGérard Mortha

Abstract

Lignin is an aromatic biopolymer derived from lignocellulosic biomass. Providing a comprehensive structural analysis of lignin is the primary motivation for the quantification of various functional groups, with a view to valorizing lignin in a wide range of applications. This study investigated the lignin fluorobenzylation reaction and performed a subsequent 19F-NMR analysis to quantify hydroxyl groups, based on a work developed two decades ago by Barrelle et al. The objectives were to check the assignments proposed in this previous study and to examine the reactivity of various types of lignin hydroxyls with the derivatization agent. Selected lignin model compounds containing phenolic and aliphatic hydroxyls were subjected to the fluorobenzylation reaction, and the obtained reaction medium was analyzed by 13C and 19F NMR spectroscopy. The model compound results showed that phenolic hydroxyls were totally derivatized, whereas aliphatic hydroxyls underwent minimal conversion. They also confirmed that 19F NMR chemical shifts from -115 ppm to -117.3 ppm corresponded to phenolic groups. Then, a 19F NMR analysis was successfully applied to Organosolv commercial lignin after fluorobenzylation in order to quantify its phenolic group c...Continue Reading

References

Aug 22, 2001·Journal of Agricultural and Food Chemistry·Z XiaD S Argyropoulos
Oct 20, 2015·Chemical Reviews·Changzhi LiTao Zhang
Aug 9, 2019·Nature Protocols·Xianzhi MengDimitris S Argyropoulos

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Citations

Dec 19, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Beata PodkościelnaKamil Dziuba

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Methods Mentioned

BETA
chemical modification
acetylation
NMR

Software Mentioned

LINUX TopSpin

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