Gaschromatographische Analyse von Ligninoxydationsprodukten. III. Oxydativer Abbau von methyliertem Björkman-Lignin (Fichte).

Larsson, Sam; Miksche, Gerhard E.; Cowling, E.; Lin, Sunny S. J.; Chan, Rosalind P. K.; Craig, J. Cymerman

doi:10.3891/acta.chem.scand.23-3337

Cited by 34 publications

(22 citation statements)

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“…Only a trace of tri-O-methylgallic acid (VI) was detected. These data are in accord with a guaiacyl lignin Ludwig 1971, Larsson andMiksche 1969). The yield of veratric acid is too high relative to the yields of IV and V, but this is ascribed to a polyphenol contaminant in the lignin, whose presence was established by oxidative degradation of an ethylated sample.…”

Section: Characterization Ofligninssupporting

confidence: 71%

“…Oxidative degradation.-The procedures were adapted from those of Larsson and Miksche (1969), and entailed permanganate oxidation of methylated or ethylated samples (50 mg) at pH 9-10, followed by further oxidation with H2O2 at pH 12. Aromatic acid products were identified and estimated by gas chromatography of the methyl esters.…”

Section: Characterization Ofligninsmentioning

confidence: 99%

“…Degradation studies have shown that lignin from whole wood of beech and birch consists ci least in part of a copolymer of guaiacyl and syringyl phenylpropanoid units (Larsson andMiksche 1971, Nimz 1966). However, it has not been conclusively demonstrated whether angiosperm lignin is uniformly copolymeric or whether some cell types or morphological regions contain lignin with mainly guaiacyl units (guaiacyl lignin) while others contain lignin with predominantly syringyl units (syringyl lignin).…”

Section: Introductionmentioning

confidence: 99%

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Guaiacyl Lignin Associated with Vessels in Aspen Callus Cultures

Wolter

Harkin

Kirk

1974

Physiologia Plantarum

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Section: Characterization Ofligninssupporting

confidence: 71%

Section: Characterization Ofligninsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Guaiacyl Lignin Associated with Vessels in Aspen Callus Cultures

Wolter

Harkin

Kirk

1974

Physiologia Plantarum

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“…Potassium permanganate oxidation is a chemical degradation method for the determination of the type and frequency of bondings between the aromatic rings in lignins [35][36][37][38][39][40]. It leads to selective cleavage of aliphatic side chains and can produce up to 20 aromatic methyl esters of different carbonic acids.…”

Section: Kmno 4 -Oxidationmentioning

confidence: 99%

Characterization of the water-insoluble fraction from fast pyrolysis liquids (pyrolytic lignin). Part IV: Structure elucidation of oligomeric molecules

Bayerbach

Meier

2009

Journal of Analytical and Applied Pyrolysis

198

146

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“…1. The relative frequencies of these moieties have been determined by a variety of degradative techniques, i.e., oxidative degradation (3)(4)(5) and thioacidolysis-desulfuration (6). Amongst the nondegradative methods of analysis, advanced 13 C NMR spectroscopy may offer a quantitative estimate for some of these units (7).…”

Section: Introductionmentioning

confidence: 99%

Coupling P-31 NMR with the Mannich reaction for the quantitative analysis of lignin

Jiang¹,

Argyropoulos²

1998

Rev. Can. Chim.

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The reactivity of lignin model compounds under Mannich conditions with piperidine and formaldehyde was studied. The piperidinomethyl group was confirmed to be introduced quantitatively at sterically unhindered positions ortho to a phenolic hydroxyl when the substrate was allowed to react under ambient conditions. The sequential application of the Mannich reaction followed by quantitative 31 P NMR on a variety of lignin samples allowed the amounts of various aromatic groups bearing free phenolic hydroxyls to be determined. More specifically, the technique allowed the quantification of para-hydroxyl phenols, catechols, guaiacols, and phenols bearing C 5 or C 6 substituents. The quantitative reliability of the technique was also examined with a series of dissolved kraft lignins, isolated at various degrees of delignification. The data were found to favourably compare to those obtained by permanganate oxidation.Résumé : On a étudié la réactivité de composés modèles de la lignine dans la réaction de Mannich avec de la pipéridine et du formaldéhyde. Il a été confirmé que, lorsque le substrat réagit dans des conditions ambiantes, le groupe pipéridinométhyle s'introduit quantitativement dans les positions stériquement non empêchées en ortho de l'hydroxyle phénolique. L'application séquentielle de la réaction de Mannich sur divers échantillons de lignine, suivie d'une étude quantitative RMN du 31 P, permet de déterminer les quantités de divers groupes aromatiques portant des hydroxyles phénoliques. D'une façon plus spécifique, la technique permet de quantifier les para-hydroxyphénols, les catéchols, les guaïacols et les phénols portant des substituants en C 5 et en C 6 . On a aussi évalué la fiabilité quantitative de la technique avec une série de lignines kraft dissoutes, isolées à divers degrés de délignification. On a trouvé que les données se comparent favorablement à celles obtenues par oxydation avec le permanganate.Mots clés : lignine, composés modèles de la lignine, réaction de Mannich, résonance magnétique nucléaire (RMN), phénols, phosphore, pipéridine, analyse quantitative. [Traduit par la rédaction]Can.

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Gaschromatographische Analyse von Ligninoxydationsprodukten. III. Oxydativer Abbau von methyliertem Björkman-Lignin (Fichte).

Cited by 34 publications

References 0 publications

Guaiacyl Lignin Associated with Vessels in Aspen Callus Cultures

Guaiacyl Lignin Associated with Vessels in Aspen Callus Cultures

Characterization of the water-insoluble fraction from fast pyrolysis liquids (pyrolytic lignin). Part IV: Structure elucidation of oligomeric molecules

Coupling P-31 NMR with the Mannich reaction for the quantitative analysis of lignin

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