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

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

doi:10.1039/C6OB01915C

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

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

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	10023-10030
Number of pages	8
Journal	Organic & Biomolecular Chemistry
Volume	14
Issue number	42
Early online date	22 Sept 2016
DOIs	https://doi.org/10.1039/C6OB01915C
Publication status	Published - 14 Nov 2016

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10.1039/C6OB01915C

Westwood_2016_OBC_Synthesis_AAM
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
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Cite this

@article{f3d6769d7ab2406ea11585cacb8ae880,

title = "The synthesis and analysis of lignin-bound Hibbert ketone structures in technical lignins",

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.",

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

note = "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).",

year = "2016",

month = nov,

day = "14",

doi = "10.1039/C6OB01915C",

language = "English",

volume = "14",

pages = "10023--10030",

journal = "Organic & Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

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T1 - The synthesis and analysis of lignin-bound Hibbert ketone structures in technical lignins

AU - Miles-Barrett, Daniel

AU - Neal, Andrew

AU - Hand, Calum

AU - Montgomery, James

AU - Panovic, Isabella

AU - Ojo, Oluwarotimi Stephen

AU - Lancefield, Christopher Stuart

AU - Cordes, David B.

AU - Slawin, Alexandra M. Z.

AU - Lebl, Tomas

AU - Westwood, Nicholas J.

N1 - 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).

PY - 2016/11/14

Y1 - 2016/11/14

N2 - 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.

AB - 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.

UR - http://www.rsc.org/suppdata/c6/ob/c6ob01915c/c6ob01915c1.pdf

U2 - 10.1039/C6OB01915C

DO - 10.1039/C6OB01915C

M3 - Article

SN - 1477-0520

VL - 14

SP - 10023

EP - 10030

JO - Organic & Biomolecular Chemistry

JF - Organic & Biomolecular Chemistry

IS - 42

ER -

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

Abstract

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CRITICAT CDT: Critical Resource Catalysis - CRITICAT

Clean catalysis for sustainable develop: Clean catalysis for sustainable development

GLOBAL: GLOBAL Joining forces in sustainable catalysis and energy based on renewables

Exploiting Site-Selective Reactivity in the Processing of Lignin (thesis data)

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

Cite this

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

Abstract

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Other files and links

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Projects

CRITICAT CDT: Critical Resource Catalysis - CRITICAT

Clean catalysis for sustainable develop: Clean catalysis for sustainable development

GLOBAL: GLOBAL Joining forces in sustainable catalysis and energy based on renewables

Datasets

Exploiting Site-Selective Reactivity in the Processing of Lignin (thesis data)

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

Cite this