Nucleophilic Cleavage of Lignin Model Compounds under Acidic Conditions in an Ionic Liquid: A Mechanistic Study. Issue 5 (6th April 2018)

• Record Type: Journal Article
• Authors: Hart, William E. S.; Aldous, Leigh; Harper, Jason B.
• Is Part Of: ChemPlusChem. Volume 83:Issue 5(2018)
• Page Start: 348
• Page End: 353
• Publication Date: 2018-04-06
• Subjects: biomass -- hydrogen bromide -- ionic liquids -- lignin model compounds -- solvent effects; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/cplu.201700486
• Languages: English
• ISSNs: 2192-6506

Abstract

Abstract: A range of lignin model compounds were examined for their reactivity with hydrogen bromide in the ionic liquid N ‐butylpyridinium triflate. It was found that the ionic liquid enabled rapid reaction at both the hydroxy and methyl ether sites of the model compounds at room temperature. Reactions at the phenyl ether moieties were more complex; rather than facilitating cleavage at these sites, alternate breakdown products that had not been seen in previous studies were observed; these products are consistent with functionalisation of the aromatic components of the model compounds. Abstract : It cuts both ways : The selective cleavage of lignin model compounds with hydrogen bromide was observed in an ionic liquid. Reaction at the phenyl ether site was notably slower and different to what has been observed previously. These processes have application in the functionalisation and fractionation of lignin.