The synthesis and analysis of lignin-bound Hibbert ketone structures in technical lignins
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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.
Miles-Barrett , D , Neal , A , Hand , C , Montgomery , J , Panovic , I , Ojo , O S , Lancefield , C S , Cordes , D B , Slawin , A M Z , Lebl , T & Westwood , N J 2016 , ' The synthesis and analysis of lignin-bound Hibbert ketone structures in technical lignins ' Organic & Biomolecular Chemistry , vol 14 , no. 42 , pp. 10023-10030 . DOI: 10.1039/C6OB01915C
Organic & Biomolecular Chemistry
Copyright 2016 the Authors. This work is made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at https://dx.doi.org/10.1039/C6OB01915C
This work was supported by EPSRC Ph.D. studentships (EP/1518175 (DMB), EP/1517938 (AN)), the Industrial Biotechnology Innovation Centre (Ph.D. studentship to DMB), CRITICAT Centre for Doctoral Training (Ph.D. studentship to IP; EP/L016419/1), EPSRC grants EP/J018139/1 and EP/K00445X/1 (SOJO) and an EPSRC Doctoral Prize Fellowship (CSL).
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