Synthesis of β-O-4-type artificial lignin polymers and their analysis by NMR spectroscopy

Kishimoto, Takao; Uraki, Yasumitsu; Ubukata, Makoto

doi:10.1039/b805460f

Cited by 51 publications

(62 citation statements)

References 15 publications

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“…The two compounds were synthesized by stepwise condensation of acetovanillone to form b-linked diketo ester (Supplemental Figs. S2 and S3) under reaction conditions similar to those reported by Kishimoto et al (2008aKishimoto et al ( , 2008b.…”

Section: Lignin Hydrodynamic Volume Model Compoundssupporting

confidence: 66%

Highly Decorated Lignins in Leaf Tissues of the Canary Island Date Palm Phoenix canariensis

et al. 2017

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Section: Lignin Hydrodynamic Volume Model Compoundssupporting

confidence: 66%

Highly Decorated Lignins in Leaf Tissues of the Canary Island Date Palm Phoenix canariensis

et al. 2017

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“…Three lignin model compounds 1–3 (Figure ), each containing only β‐O‐4 linkages ( 1 and 2 are trans ‐isomers (mixtures of (R,S)‐ and (S,R)‐absolute configurations for each β‐O‐4 linkage) while 3 is even a more complex mixture of diastereomers, containing both cis ‐ and trans ‐linkages), were used in this study – a trimer ( 1 ), a tetramer ( 2 ) and a polymer ( 3 ). The degree of polymerization (n; Figure ) of polymer 3 is about 20 . The synthetic procedures used to prepare 1, 2 and 3 have been described previously ,.…”

Section: Resultsmentioning

confidence: 98%

Initial Products and Reaction Mechanisms for Fast Pyrolysis of Synthetic G‐Lignin Oligomers with β‐O‐4 Linkages via On‐Line Mass Spectrometry and Quantum Chemical Calculations

et al. 2017

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The products of fast pyrolysis that first leave the hot pyrolysis surface were identified for three G‐lignin model compounds, a trimer, a tetramer and a synthetic polymer, all containing β‐O‐4 linkages, by using a very fast heating pyrolysis probe coupled with a linear quadrupole ion trap mass spectrometer or a linear quadrupole ion trap coupled with an orbitrap detector. High‐resolution measurements were used to determine the elemental compositions of the deprotonated pyrolysis products. Their structures were examined using collision‐activated dissociation experiments and via comparison to the dissociation reactions of ionized authentic compounds. The initial pyrolysis products for all model compounds range from monomers to tetramers. Even for the polymer, no products larger than tetramers were observed. None of the products were radicals. The observed trimers and tetramers were formed directly from the intact model compounds rather than from repolymerization of initially formed monomers. Both the observed product distributions and quantum chemical calculations suggest that the mechanism(s) of the major reactions occurring under the conditions employed here are Maccoll and/or retro‐ene eliminations rather than radical reactions. Based on a comparison of the behavior of the smaller β‐O‐4 model compounds to the synthetic β‐O‐4 lignin polymer, the smaller model compounds appear to be good surrogates for further studies of the mechanisms of fast pyrolysis of lignin.

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“…1. Coniferyl alcohol, dimers and polymers were synthesized as previously described 14–16. Sinapyl alcohol was purchased from Aldrich.…”

Section: Methodsmentioning

confidence: 99%

Application of TOF‐SIMS to the direct determination of syringyl to guaiacyl (S/G) ratio of lignin

Saito

Kishimoto

Matsushita

et al. 2011

Surface & Interface Analysis

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The lignin syringyl to guaiacyl (S/G) ratio, the composition of monomeric units, is an important parameter that is widely used to obtain information on the complex polymer structure of lignin present in plant cell walls. We assessed the reliability of time-of-flight secondary ion mass spectrometry (TOF-SIMS) for determining the S/G ratio using monomer, dimer and polymer model compounds of lignin. In the case of the monomer and dimer, the S/G ratios were much higher than the actual molar S/G ratios. In contrast, for the aryl ether 8-O-4 -linked polymers, the S/G ratios estimated were similar to the actual S/G molar ratios, suggesting that the ionization efficiencies of the characteristic ions of S and G units detected from the synthetic lignin polymer compounds were similar. The results suggest that TOF-SIMS is useful for rapid and convenient determination of the lignin S/G ratio in plants.

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Synthesis of β-O-4-type artificial lignin polymers and their analysis by NMR spectroscopy

Cited by 51 publications

References 15 publications

Highly Decorated Lignins in Leaf Tissues of the Canary Island Date Palm Phoenix canariensis

Highly Decorated Lignins in Leaf Tissues of the Canary Island Date Palm Phoenix canariensis

Initial Products and Reaction Mechanisms for Fast Pyrolysis of Synthetic G‐Lignin Oligomers with β‐O‐4 Linkages via On‐Line Mass Spectrometry and Quantum Chemical Calculations

Application of TOF‐SIMS to the direct determination of syringyl to guaiacyl (S/G) ratio of lignin

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