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Selective utilization of methoxy groups in lignin for N-methylation reaction of anilines

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Abstract

The utilization of lignin as a feedstock to produce valuable chemicals is of great importance. However, it is a great challenge to produce pure chemicals because of the complex structure of lignin. The selective utilization of specific groups on lignin molecules offers the possibility of preparing chemicals with high selectivity, but this strategy has not attracted attention. In this work, we propose a protocol to produce methyl-substituted amines by the selective reaction of the methoxy groups of lignin and aniline compounds. It was found that LiI in the ionic liquid 1-hexyl-3-methylimidazolium tetrafluoroborate could catalyze the reaction efficiently and the selectivity to the N-methylation product could be as high as 98%. Moreover, the lignin was not depolymerized in the reaction. As it was rich in hydroxyl groups, the residual material left over after the reaction was used as an efficient co-catalyst for the cycloaddition of epoxy propane with CO2, using KI as the catalyst.

Graphical abstract: Selective utilization of methoxy groups in lignin for N-methylation reaction of anilines

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Publication details

The article was received on 06 Jul 2018, accepted on 31 Oct 2018 and first published on 01 Nov 2018


Article type: Edge Article
DOI: 10.1039/C8SC03006E
Citation: Chem. Sci., 2019, Advance Article
  • Open access: Creative Commons BY-NC license
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    Selective utilization of methoxy groups in lignin for N-methylation reaction of anilines

    Q. Mei, X. Shen, H. Liu, H. Liu, J. Xiang and B. Han, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C8SC03006E

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