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  • Author: H. Önnerud x
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Summary

The chemical structure of lignin in normal and compression wood of spruce has been studied. Thioacidolysis using both methanethiol and ethanethiol as nucleophiles was used for degradation. The results showed that these nucleophiles work equally well in thioacidolysis, but that methanethiol gives a somewhat higher yield than ethanethiol. In spruce compression wood, several of the monomeric, dimeric and trimeric products were structurally elucidated using gas chromatography-mass spectrometry analysis of the desulphurated thioacidolysis products. Some of the oligomeric structures contained a p-hydroxyphenyl unit, but most of the material seemed to be present in non-condensed β-O-4 structures. A catechol structure was found and the results also indicated the presence of β-5 stilbene structures in native spruce lignin.

Summary

Thioacidolysis, periodate oxidation and size exclusion chromatography (SEC) were used for the analysis of spruce lignin samples. The standard thioacidolysis method was modified by including a pre-swelling of the lignocellulosic sample before the reaction, and this gave a higher yield of monomer products. Middle lamella and compression wood lignin was found to contain a larger amount of oligomers after thioacidolysis than normal wood lignin. Analysis by thioacidolysis of a thermomechanical pulp (TMP) revealed that approximately 10% of the β-O-4 structures in the lignin were cleaved due to the mechanical grinding effect. From kraft pulp, the mixture of thioacidolysis products contains a major fraction having a considerably larger molecular mass than the products from spruce wood and TMP. The structure of this material is still unknown.

Summary

Bauer-McNett fractions of an aspen chemi-thermomechanical pulp showed a significant variation with respect to lignin content and sugar composition, and two of the fractions were found to be particularly rich in middle lamella and secondary wall material, respectively. The secondary wall lignin of aspen was found to contain larger amounts of non-condensed β-O-4 aryl ether structures than the middle lamella lignin and the difference was attributed to a larger amount of syringyl structures as revealed by thioacidolysis. Size exclusion chromatography of the thioacidolysis products from birch and spruce wood showed a larger part of lignin oligomers being present in the degraded spruce lignin. Moreover, birch lignin had a lower phenolic content than both aspen and spruce lignin. Thioacidolysis followed by Raney-nickel desulphuration was used for the analysis of hardwood lignin trimers.

Summary

Electrospray ionisation Fourier transform ion cyclotron resonance mass spectrometry (MS) and size exclusion chromatography (SEC) was utilised for analysis of milled wood lignin (MWL) and lignin model compounds degraded by thioacidolysis. MS and SEC showed that thioacidolysis was an efficient method for degradation of the β-O-4 bond in lignin. Moreover, the molecular weight of thioacidolysed pinoresinol and MWL were analysed using matrix assisted laser desorption ionisation time-of-flight mass spectrometry. Tandem MS was successfully applied for the structural determination of thioacidolysed pinoresinol with and without acetylation of the product. The MS results of thioacidolysis on MWL resulted in the identification of a tetrameric lignin structure containing a 5-O-4, 5-5, β-1 linkage pattern.