The DFRC Method for Lignin Analysis. 2. Monomers from Isolated Lignins

Journal of Agricultural and Food Chemistry

Volumn 46, Issue 2, 1998, Pages 547-552

  Lu, Fachuang ^b   Ralph, John ^a  

^a U S DAIRY FORAGE RESEARCH CENTER   (United States)

^b NONE

Author keywords

Acetyl bromide; DFRC; Lignin; Quantitative analysis; Reductive elimination; Thioacidolysis; aryl ether; bromoether

Indexed keywords

DICOTYLEDONEAE; POACEAE;

EID: 0001657363     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf970676m     Document Type: Article

References (34)

1. Adler, E. Lignin chemistry-past, present and future. Wood Sci. Technol. 1977, 11, 169-218.
2. Bagby, M. O.; Cunningham, R. L.; Maloney, R. L. Ultraviolet spectral determination of lignin. Tappi 1973, 56, 162-163.
3. Björkman, A. Isolation of lignin from finely divided wood with neutral solvents. Nature 1954, 174, 1057-1058.
4. Dence, C. W. The determination of lignin. In Methods in Lignin Chemistry; Lin, S. Y., Dence, C. W., Eds.; Springer-Verlag: Heidelberg, 1992; pp 33-61.
5. Ede, R. M.; Ralph, J. Assignment of 2D TOCSY spectra of lignins: the role of lignin model compounds. Magn. Reson. Chem. 1996, 34, 261-268.
6. Fukagawa, N.; Meshitsuka, G.; Ishizu, A. 2D NMR study of residual lignin in Beech Kraft pulp combined with selective cleavage with pivaloyl iodide. J. Wood Chem. Technol. 1992, 12, 425-445.
7. Harkin, J. M. Lignin. In Chemistry and Biochemistry of Herbage; Butler, G. W., Ed.; Academic Press: London, 1973; pp 323-373.
8. Iiyama, K.; Wallis, A. F. A. An improved acetyl bromide procedure for determining lignin in woods and wood pulps. Wood Sci. Technol. 1988, 22, 271-280.
9. Johnson, D. B.; Moore, W. E.; Zank, L. C. The spectrophotometric determination of lignin in small wood samples. Tappi 1961, 44, 793-789.
10. Kilpeläinen, I.; Sipilä, J.; Brunow, G.; Lundquist, K.; Ede, R. M. Application of two-dimensional NMR spectroscopy to wood lignin determination; Identification of some minor structural units of hard- and softwood lignins. J. Agric. Food Chem. 1994, 42, 2790-2794.
11. 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.
12. Lapierre, C.; Rolando, C.; Monties, B. Characterization of poplar lignins acidolysis products: capillary gas-liquid and liquid-liquid chromatography of monomeric compounds. Holzforschung 1983, 37, 189-198.
13. Lapierre, C.; Monties, B.; Rolando, C. Thioacidolysis of lignin: comparison with acidolysis. J. Wood Chem. Technol. 1985, 5, 277-292.
14. Lapierre, C.; Monties, B.; Rolando, C. Thioacidolysis of poplar lignins: identification of monomeric syringyl products and characterization of guaiacyl-syringyl lignin fractions. Holzforschung 1986, 40, 113-118.
15. Lapierre, C.; Tollier, M. T.; Monties, B. A new type of constitutive unit in lignins from the corn bm3 mutant. C. R. Acad. Sci., Ser. 3 1988, 307, 723-728.
16. Lapierre, C.; Pollet, B.; Monties, B. Thioacidolysis of spruce lignin: gas chromatography-mass spectroscopy analysis of the main dimers recovered after Raney nickel desulfurization. Holzforschung 1991, 45, 61-68.
17. 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. 1997a, 45, 2590-2592.
18. Lu, F.; Ralph, J. The DFRC method for lignin analysis. Part 1. A new method for β-aryl ether cleavage: lignin model studies. J. Agric. Food Chem. 1997b, 45, 4655-4660.
19. Lu, F.; Ralph, J. Efficient ether cleavage in lignins: the "DFRC" method as a basis for new analytical methods. In Lignin and Lignan Biosynthesis; Lewis, N. G., Sarkanen, S., Eds.; American Chemical Society: Washington, DC, 1998; in press.
20. Lundquist, K. Acidolysis. In Methods in Lignin Chemistry; Lin, S. Y., Dence, C. W., Eds.; Springer-Verlag: Heidelberg, 1992; pp 287-300.
21. Makino, S.; Meshitsuka, G.; Ishizu, A. Selective Cleavage of ether bonds in lignin by trimethylsilyl iodide. Mokuzai Gakkaishi 1990, 36, 460-465.
22. Martin, J. Determination of lignin in small pulp and paper samples using the acetyl bromide method. Tappi 1987, 50, 335-337.
23. Meshitsuka, G.; Kondo, T.; Nakano, J. Cleavage of β-aryl ether bonds in lignin by trimethylsilyl iodide. J. Wood Chem. Technol. 1987, 7, 161-178.
24. Morrison, I. M. Improvements in the acetyl bromide technique to determine lignin and digestibility and its application to legumes. J. Sci. Food Agric. 1972, 23, 1463-1469.
25. Nimz, H. Cleavage of ether compounds by neighboring mercapto-groups. Model experiments of lignin degradation with thioacetic acid. Chem. Ber. 1969, 102, 3803-3817.
26. Nimz, H. Beech lignin-proposal of a constitutional scheme. Angew. Chem., Int. Ed. Engl. 1974, 13, 313-321.
27. Quideau, S.; Ralph, J. Facile large-scale synthesis of coniferyl, sinapyl, and p-coumaryl alcohol. J. Agric. Food Chem. 1992, 40, 1108-1110.
28. Ralph, J. An unusual lignin from kenaf. J. Nat. Prod. 1996, 59, 341-342.
29. Ralph, J.; Hatfield, R. D. Pyrolysis-GC-MS characterization of forage materials. J. Agric. Food Chem. 1991, 39, 1426-1437.
30. Ralph, J.; Hatfield, R. D.; Quideau, S.; Helm, R. F.; Grabber, J. H.; Jung, H.-J. G. Pathway of p-coumaric acid incorporation into maize lignin as revealed by NMR. J. Am. Chem. Soc. 1994, 116, 9448-9456.
31. Ralph, J.; Hatfield, R. D.; Lu, F.; Grabber, J. H.; Jung, H. G.; Han, J. S.; Ralph, S. A. Eighth International Symposium on Wood and Pulping Chemistry, Helsinki, Finland; KCL: 1995; Vol. II, pp 125-128.
32. Rolando, C.; Monties, B.; Lapierre, C. Thioacidolysis. In Methods in Lignin Chemistry; Dence, C. W., Lin, S. Y., Eds.; Springer-Verlag: Berlin, 1992; pp 334-349.
33. Sakakibara, A. Chemistry of lignin. In Wood and Cellulosic Chemistry; David, N.-S. H., Nobuo, S., Eds.; Dekker: New York, 1991; pp 113-175.
34. Shevchenko, S. M.; Akim, L. G.; Pranovich, A. V.; Zarubin, M. Y. Dry hydrogen iodide as a mild cleaving reagent for lignins, Tappi 1991, 257-262.