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The synthesis and analysis of lignin-bound Hibbert ketone structures in technical lignins

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Daniel Miles-Barrett, Andrew Neal, Calum Hand, James Montgomery, Isabella Panovic, Oluwarotimi Stephen Ojo, Christopher Stuart Lancefield, David B. Cordes, Alexandra M. Z. Slawin, Tomas Lebl, Nicholas J. Westwood

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Abstract

Understanding the structure of technical lignins resulting from acid-catalysed treatment of lignocellulosic biomass is important for their future applications. Here we report an investigation into the fate of lignin under acidic aqueous organosolv conditions. In particular we examine in detail the formation and reactivity of non-native Hibbert ketone structures found in isolated organosolv lignins from both Douglas fir and beech woods. Through the use of model compounds combined with HSQC, HMBC and HSQC-TOCSY NMR experiments we demonstrate that, depending on the lignin source, both S and G lignin-bound Hibbert ketone units can be present. We also show that these units can serve as a source of novel mono-aromatic compounds following an additional lignin depolymerisation reaction.
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Original languageEnglish
Pages (from-to)10023-10030
Number of pages8
JournalOrganic & Biomolecular Chemistry
Volume14
Issue number42
Early online date22 Sep 2016
DOIs
StatePublished - 14 Nov 2016

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