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Issue 83, 2017, Issue in Progress
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Esterification mechanism of lignin with different catalysts based on lignin model compounds by mechanical activation-assisted solid-phase synthesis

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Abstract

In order to learn about the esterification mechanism of lignin by mechanical activation-assisted solid-phase synthesis (MASPS) technology, lignin model compounds, p-hydroxy benzaldehyde (H), vanillin and vanillyl alcohol (G), and syringaldehyde (S), were used in the reaction with acetic anhydride, with 4-dimethyl amino pyridine (DMAP), sodium acetate, and sulfuric acid as catalysts. FTIR, NMR, and UV/vis analyses of the products showed that all of the catalysts could enhance the esterification. Both the phenolic hydroxyl and aliphatic hydroxyl participated in the esterification and the reactivity of the basic structural units of lignin had a descending order of H, G, and S. Oxidations could happen in the presence of unsaturated groups such as aldehyde in the lignin model compounds. The catalytic mechanism of the three kinds of catalyst was different, and the catalytic activity had a descending order of DMAP, sodium acetate, and sulfuric acid. The reactivity of phenolic hydroxyl was higher than that of aliphatic hydroxyl with DAMP as the catalyst, but the reactivity of aliphatic hydroxyl was higher than that of phenolic hydroxyl with sodium acetate or sulfuric acid as the catalyst. With sulfuric acid as the catalyst, some side reactions took place and resulted in the ring cleavage or cross-linking of the benzene ring. Consistency verification indicated that the use of lignin model compounds for studying the esterification mechanism of lignin was reasonable and feasible.

Graphical abstract: Esterification mechanism of lignin with different catalysts based on lignin model compounds by mechanical activation-assisted solid-phase synthesis

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Publication details

The article was received on 21 Sep 2017, accepted on 07 Nov 2017 and first published on 10 Nov 2017


Article type: Paper
DOI: 10.1039/C7RA10482K
Citation: RSC Adv., 2017,7, 52382-52390
  • Open access: Creative Commons BY-NC license
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    Esterification mechanism of lignin with different catalysts based on lignin model compounds by mechanical activation-assisted solid-phase synthesis

    X. Zhao, Y. Zhang, L. Wei, H. Hu, Z. Huang, M. Yang, A. Huang, J. Wu and Z. Feng, RSC Adv., 2017, 7, 52382
    DOI: 10.1039/C7RA10482K

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