Understanding and Suppression of Side Reaction during Transesterification of Phenolic Hydroxyl Groups of Lignin with Vinyl Ester

A catalytic transesterification reaction on phenolic hydroxyl groups by a carboxylate-type ionic liquid, 1-ethyl-3-methylimidazolium p-anisate ([Emim][OAn]), was investigated using a model reaction with phenol and vinyl propionate. Undesirable contamination of the ester group formed on the phenol wi...

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Bibliographic Details
Published in:Chemistry letters 2020-08, Vol.49 (8), p.900-904
Main Authors: Suzuki, Shiori, Ishikuro, Akinari, Hamano, Yosuke, Hirose, Daisuke, Wada, Naoki, Takahashi, Kenji
Format: Article
Language:English
Subjects:
Esterification
Hydroxyl groups
Ionic liquids
Lignin
Phenols
Transesterification
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Summary:A catalytic transesterification reaction on phenolic hydroxyl groups by a carboxylate-type ionic liquid, 1-ethyl-3-methylimidazolium p-anisate ([Emim][OAn]), was investigated using a model reaction with phenol and vinyl propionate. Undesirable contamination of the ester group formed on the phenol with an acyl group derived from the acyl anion in the [Emim][OAn] was effectively suppressed. This catalytic reaction was applied to Kraft lignin, and the desired esterification was successfully promoted on the hydroxyl groups with a conversion of up to 94 mol %.
ISSN:0366-7022
1348-0715
DOI:10.1246/cl.200202