Understanding the degree of condensation of phenolic and etherified C-9 units of in situ lignins

Journal of Agricultural and Food Chemistry

Volumn 59, Issue 23, 2011, Pages 12514-12519

  Nanayakkara, Bernadette ^a   Manley Harris, Merilyn ^a   Suckling, Ian D ^b  

^a UNIVERSITY OF WAIKATO   (New Zealand)

^b SCION   (New Zealand)

Author keywords

aryl ether linkages; 31P NMR spectroscopy; compression wood; degree of condensation; etherified C 9 units; in situ lignin; methylated wood; milled wood lignin; phenolic C 9 units; Pinus radiata; thioacidolysis

Indexed keywords

31P-NMR SPECTROSCOPY; ARYL ETHER; DEGREE OF CONDENSATION; ETHERIFIED C-9 UNITS; MILLED WOOD LIGNIN; PHENOLIC C-9 UNITS; PINUS RADIATA; THIOACIDOLYSIS;

CONDENSATION; ETHERS; LIGNIN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHENOLS;

WOOD;

ETHER DERIVATIVE; LIGNIN; PHENOL DERIVATIVE;

ARTICLE; CHEMISTRY; METHYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PINE; WOOD;

ETHERS; LIGNIN; MAGNETIC RESONANCE SPECTROSCOPY; METHYLATION; PHENOLS; PINUS; WOOD;

COMPRESSION WOOD; CONDENSATION; ETHERS; LIGNINS; NUCLEAR MAGNETIC RESONANCE; PHENOLS; PINUS RADIATA;

EID: 83055165683     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf203285r     Document Type: Article

References (53)

1. Brunow, G.; Lundquist, K. Functional groups and bonding patterns in lignin (including the lignin carbohydrate complexes). In Lignin and Lignans Advances in Chemistry; Heitner, C., Dimmel, D. R., Schmidt, J. A., Eds.; CRC Press: Boca Raton, FL, 2010; pp 267-299.
2. Chakar, F. S.; Ragauskas, A. J. Review of current and future softwood kraft lignin process chemistry Ind. Crop Prod. 2004, 20, 131-141
3. Dimmel, D. R.; Gellerstedt, G. Chemistry of alkaline pulping. In Lignins and Lignans Advances in Chemistry; Heitner, C.; Dimmel, D. R.; Schmidt, J. A., Eds.; CRC Press: Boco Raton, FL, 2010; pp 349-391.
4. Bose, S. K.; Wilson, K. L.; Francis, R. C.; Aoyama, M. Lignin analysis by permanganate oxidation. 1. Native spruce lignin Holzforschung 1998, 52 (3) 297-303
5. Lai, Y.-Z.; Guo, X.-P. Variation of the phenolic hydroxyl group content in wood lignins Wood Sci. Technol. 1991, 25, 467-472
6. Gierer, J. Chemistry of delignification. Part 2: Reactions of lignins during bleaching Wood Sci. Technol. 1986, 20 (1) 1-33
7. Lai, Y.-Z.; Guo, X.-P. The effect of wood species in sulfonation Holzforschung 1992, 46 (6) 477-480
8. Heitner, C. The photochemistry of lignin. In Lignins and Lignans Advances in Chemistry; Heitner, C.; Dimmel, D. R.; Schmidt, J. A., Eds.; CRC Press: Boca Raton, FL, 2010; pp 555-584.
9. Björkman, A. Studies on finely divided wood. Part 1. Extraction of lignin with neutral solvents Svensk Papperstidn. 1956, 59, 477-485
10. Lundquist, K. Isolation and purification. In Methods in Lignin Chemistry; Lin, S. Y.; Dence, C. W., Eds.; Springer-Verlag: Berlin, Germany, 1992; pp 65-70.
11. Guerra, A.; Filpponen, I.; Lucia, L. A.; Argyropoulos, D. S. Comparative evaluation of three lignin isolation protocols for various wood species J. Agric. Food Chem. 2006, 54 (26) 9696-9705
12. Wu, S.; Argyropoulos, D. S. An improved method for isolating lignin in high yield and purity J. Pulp Pap. Sci. 2003, 29 (7) 235-240
13. Marlin, N.; Lachenal, D.; Magnin, L.; Brochier-Salon, M. C. Study of the oxygen effect on mechanical pulp lignin using an improved lignin isolation method Holzforschung 2005, 59 (2) 116-123
14. Bland, D. E.; Sternhell, S. Estimation of aromatic protons in methanol lignins of Pinus radiata and Eucalyptus regnans from proton magnetic resonance spectra Aust. J. Chem. 1965, 18, 401-410
15. Capanema, E. A.; Balakshin, M. Y.; Kadla, J. F. A comprehensive approach for quantitative lignin characterization by NMR spectroscopy J. Agric. Food Chem. 2004, 52, 1850-1860
16. Nimz, H. H.; Robert, D.; Faix, O.; Nemr, M. Carbon-13 NMR spectra of lignins, part 8 Holzforschung 1981, 35, 16-26
17. Lai, Y.-Z.; Sarkanen, K. V. Isolation and structural studies. In Lignins, Occurrence, Formation, Structure and Reactions; Sarkanen, K. V.; Ludwig, C. H., Eds.; Wiley-Interscience: New York, 1971; pp 165-240.
18. Rolando, C.; Monties, B.; Lapierre, C. Thioacidolysis. In Methods in Lignin Chemistry; Dence, C. W.; Lin, S. Y., Eds.; Springer-Verlag: Berlin, Germany, 1992; pp 334-349.
19. Lu, F.; Ralph, J. Derivatization followed by reductive cleavage (DFRC method), a new method for lignin analysis: protocol for analysis of DFRC monomers J. Agric. Food Chem. 1997, 45, 2590-2592
20. Chen, C.-L. Nitrobenzene and cupric oxide oxidation. In Methods in Lignin Chemistry; Lin, S. Y.; Dence, C. W., Eds.; Springer-Verlag: Berlin, Germany, 1992; pp 301-319.
21. Funaoka, M.; Abe, I.; Chiang, V. L. Nucleus exchange reaction. In Methods in Lignin Chemistry; Lin, S. Y.; Dence, C. W., Eds.; Springer-Verlag: Berlin, Germany, 1992; pp 369-386.
22. Gellerstedt, G. Chemical degradation methods: permanganate oxidation. In Methods in Lignin Chemistry; Lin, S. Y.; Dence, C. W., Eds.; Springer-Verlag: Berlin, Germany, 1992; pp 322-349.
23. Chen, C.-L. Characterisation of lignin by oxidative degradation: use of gas chromatography-mass spectrometry technique Methods Enzymol. 1988, 161, 110-136
24. Önnerud, H.; Palmbald, M.; Gellerstedt, G. Investigation of lignin oligomers using electrospray ionisation mass spectrometry Holzforschung 2003, 57 (1) 37-43
25. Lapierre, C.; Pollet, B.; Monties, B.; Rolando, C. Thioacidolysis of spruce lignin: GC-MS analysis of the main dimers recovered after Raney nickel desulfurization Holzforschung 1991, 45, 61-668
26. Sakakibara, A. Hydrogenolysis. In Methods in Lignin Chemistry; Lin, S. Y.; Dence, C. W., Eds.; Springer-Verlag: Berlin, Germany, 1992; pp 350-368.
27. Önnerud, H.; Gellerstedt, G. Inhomogeneities in the chemical structure of spruce lignins Holzforschung 2003, 57 (2) 165-170
28. Suckling, I. D.; Pasco, M. F.; Hortling, B.; Sundquist, J. Assessment of lignin condensation by GPC analysis of lignin thioacidolysis products Holzforschung 1994, 48 (6) 501-503
29. 31P NMR with the Mannich reaction toward quantitative analysis of lignins Can. J. Chem. 1998, 76 (5) 612-622
30. Mikawa, H.; Sato, K.; Takasaki, C.; Ibisawa, K. The cooking mechanism of wood. XV. Mannich reaction on lignin model compounds and the estimation of the amount of the simple guaiacyl nucleus in thiolignin Bull. Chem. Soc. Jpn. 1956, 29, 259-271
31. Adler, E.; Lundquist, K. Estimation of "uncondensed" phenolic units in spruce lignin Acta Chem. Scand. 1961, 15 (1) 233-234
32. Granata, A.; Argyropoulos, D. S. 2-Chloro-4,4,5,5-tetramethyl-1,3,2- dioxaphospholane, a reagent for the accurate determination of the uncondensed and condensed phenolic moieties in lignins J. Agric. Food Chem. 1995, 43, 1538-1544
33. Smit, R. A new method for determining condensed and uncondensed structures in lignin. Ph.D. thesis, University of Waikato, Hamilton, New Zealand, 2000.
34. 31P NMR with thioacidolysis J. Nat. Prod. 2008, 71, 836-841
35. 31P NMR J. Agric. Food Chem. 2001, 49, 536-542
36. Björkman, A.; Persson, B. Studies on finely divided wood. Part 4. Some reactions of the lignin extracted by neutral solvents from Picea abies Svensk Papperstidn. 1957, 60 (8) 285-292
37. Gierer, J.; Noren, I. On the course of delignification during kraft pulping Holzforschung 1980, 34, 197-200
38. Hardell, H.; Leary, G. J.; Stoll, M.; Westermark, U. Variations in lignin structure in defined morphological parts of spruce Svensk Papperstidn. 1980, 2, 44-49
39. Lapierre, C.; Monties, B. Thioacidolysis of diazomethane-methylated pine compression wood and wheat straw in in situ lignins Holzforschung 1988, 42, 409-411
40. Lapierre, C.; Rolando, C. Thiacidolysis of pre-methylated lignin samples from pine compression wood and poplar woods Holzforschung 1988, 42, 1-4
41. Ikeda, T.; Holtman, K. M.; Kadla, J. F.; Chang, H. M.; Jameel, H. Studies on the effect of ball milling on lignin structure using a modified DFRC method J. Agric. Food Chem. 2002, 50, 129-135
42. Timell, T. E. Opposite wood. In Compression Wood in Gymnosperms; Springer-Verlag: Berlin, Germany, 1986; Vol. 3, pp 1970-1998.
43. Petterson, R. C.; Schwandt, V. H. Wood sugar analysis by anion chromatography J. Wood Chem. Technol. 1991, 11 (4) 495-501
44. Lin, S. Y. Ultraviolet spectrophotometry. In Methods in Lignin Chemistry; Lin, S. Y.; Dence, C. W., Eds.; Springer-Verlag: Berlin, Germany, 1992; pp 215-232.
45. Pasco, M. F.; Suckling, I. D. Lignin removal during kraft pulping. An investigation by thioacidolysis Holzforschung 1994, 48 (6) 504-508
46. Chen, H.-T.; Funaoka, M.; Lai, Y.-Z. Attempts to understand the nature of phenolic and etherified components of wood lignin Wood Sci. Technol. 1997, 31, 433-440
47. Lai, Y.-Z. Determination of phenolic hydroxyl groups. In Methods in Lignin Chemistry; Dence, C. W.; Lin, S. Y., Eds.; Springer-Verlag: Berlin, Germany, 1991; pp 423-434.
48. Yasuda, S.; Sakakibara, A. The chemical composition of lignin from reaction wood Mokuzai Gakkaishi 1975, 21 (6) 363-369
49. Morohoshi, N.; Sakakibara, A. The chemical composition of reaction wood I Mokuzai Gakkaishi 1971, 17, 393-399
50. Nanayakkara, B.; Manley-Harris, M.; Suckling, I. D.; Donaldson, L. A. Quantitative chemical indicators to assess the gradation of compression wood Holzforschung 2009, 63, 431-439
51. Saito, K.; Fukushima, K. Distribution of lignin interunit bonds in the differentiating xylem of compression wood and normal woods of Pinus thunbergii J. Wood Sci. 2005, 51, 246-251
52. Fujimoto, A.; Matsumoto, Y.; Chang, H.-M.; Meshitsuka, G. Quantitative evaluation of milling effects on lignin structure during the isolation process of milled wood lignin J. Wood Sci. 2005, 51, 89-91
53. Holtman, K. M.; Chang, H. M.; Jameel, H.; Kadla, J. F. Elucidation of lignin structure through degradative methods: comparison of modified DFRC and thioacidolysis J. Agric. Food Chem. 2003, 51, 3535-3540