Revisiting alkaline nitrobenzene oxidation: quantitative evaluation of biphenyl structures in cedar wood lignin (Cryptomeria japonica) by a modified nitrobenzene oxidation method
-
Akari Tamai
and
Yuji Matsumoto
Abstract
A modified alkaline nitrobenzene oxidation (NBO) method was developed to enable the analysis of the biphenyl structures of cedar wood lignin. The most essential point of the process is a modified work-up process in pyridine and a prolonged gas chromatography analysis of the silylated products. By applying this mean to cedar wood meal, a novel biphenyl product, dehydrovanillin-vanillic acid (1-carboxy-1′-formyl-4,4′-dihydroxy-3,3′-dimethoxy-5,5′-biphenyl), was detected together with known products, dehydrodivanillin and dehydrodivanillic acid. The highest total yield of biphenyl products was detected when NBO was carried out for 2–4 h at 170°C. The work-up procedure was slightly modified so that the biphenyl products can be quantified. The NBO conversion rates of biphenyl linkages of lignin were also examined with a biphenyl-type lignin model compound, and this gave rise to 75% biphenyl-type NBO degradation products. Under the same condition, the total yield of vanillin and vanillic acid (VA) from a non-condensed-type β-O-4 model compound was 89%. Because the latter did not exhibit any peak of the biphenyl products, it can be concluded that all the biphenyl products obtained by NBO (0.17 mmol g-1) were from the lignin of the native wood. It was calculated that at least 6.7 of 100 phenylpropanoid units of cedar lignin were involved in biphenyl structures even if the NBO conversion rate was not taken into consideration. The synthesis and analytical data of 11 lignin model compounds is described.
Acknowledgments
The authors gratefully acknowledge the funding from the Japan Science and Technology Agency, PRESTO. Funding: Japan Science and Technology Agency (Grant/Award Number: ‘PRESTO’).
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©2015 by De Gruyter
Articles in the same Issue
- Frontmatter
- Original Articles
- Extraction and amplification of DNA from aged and archaeological Populus euphratica wood for species identification
- Experimental data and kinetic models in terms of methanol formation during oxygen delignification processes of alkaline pulps
- Purification and characterization of kraft lignin
- Revisiting alkaline nitrobenzene oxidation: quantitative evaluation of biphenyl structures in cedar wood lignin (Cryptomeria japonica) by a modified nitrobenzene oxidation method
- Tensile strength of handsheets prepared with macerated fibres from solid wood modified with cross-linking agents
- Investigation of bamboo pulp fiber-reinforced unsaturated polyester composites
- Mechanical imaging of bamboo fiber cell walls and their composites by means of peakforce quantitative nanomechanics (PQNM) technique
- Wood modification with tricine
- Optimizing cellulose fibrillation for the production of cellulose nanofibrils by a disk grinder
- Surface modification of natural fibers by plasma for improving strength properties of paper sheets
- Comparison of ZnO nanorod array coatings on wood and their UV prevention effects obtained by microwave-assisted hydrothermal and conventional hydrothermal synthesis
- Damage evolution in wood: synchrotron radiation micro-computed tomography (SRμCT) as a complementary tool for interpreting acoustic emission (AE) behavior
- Reinforced hybrid wood-aluminum composites with excellent fire performance
- Corrigendum
- Corrigendum to: Changes of wettability of medium density fiberboard (MDF) treated with He-DBD plasma
Articles in the same Issue
- Frontmatter
- Original Articles
- Extraction and amplification of DNA from aged and archaeological Populus euphratica wood for species identification
- Experimental data and kinetic models in terms of methanol formation during oxygen delignification processes of alkaline pulps
- Purification and characterization of kraft lignin
- Revisiting alkaline nitrobenzene oxidation: quantitative evaluation of biphenyl structures in cedar wood lignin (Cryptomeria japonica) by a modified nitrobenzene oxidation method
- Tensile strength of handsheets prepared with macerated fibres from solid wood modified with cross-linking agents
- Investigation of bamboo pulp fiber-reinforced unsaturated polyester composites
- Mechanical imaging of bamboo fiber cell walls and their composites by means of peakforce quantitative nanomechanics (PQNM) technique
- Wood modification with tricine
- Optimizing cellulose fibrillation for the production of cellulose nanofibrils by a disk grinder
- Surface modification of natural fibers by plasma for improving strength properties of paper sheets
- Comparison of ZnO nanorod array coatings on wood and their UV prevention effects obtained by microwave-assisted hydrothermal and conventional hydrothermal synthesis
- Damage evolution in wood: synchrotron radiation micro-computed tomography (SRμCT) as a complementary tool for interpreting acoustic emission (AE) behavior
- Reinforced hybrid wood-aluminum composites with excellent fire performance
- Corrigendum
- Corrigendum to: Changes of wettability of medium density fiberboard (MDF) treated with He-DBD plasma
