Wood Science and Technology

, Volume 13, Issue 3, pp 165–178 | Cite as

The structure of lignins in pulps

Part 4: Comparative evaluation of five lignin depolymerization techniques
  • N. Morohoshi
  • W. G. Glasser
Article
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Summary

Five potential lignin depolymerization techniques were evaluated with regard to their analytical value in combination with oxidation by permanganate and hydrogen peroxide. The methods included involved alkaline solutions of cupric oxide and nitrobenzene, acetolysis with thioacetic acid, derivatization with thioglycolic acid followed by alkaline hydrolysis, and reductive aminolysis with sodium in liquid ammonia. Gas and gel permeation chromatography served for the separation of product mixtures, and milled wood lignins of Loblolly pine and red alder were the lignin substrates. Whereas thioacetolysis proved most efficient in terms of lignin depolymerization, the side chains of its product mixtures were insufficiently oxygenated to warrant effective conversion into polycarboxy aromatic acids by permanganate. Cupric oxide and alkali were deemed most effective because of greatest overall yields of five prominent permanganate oxidation products combined with mildness (measured in terms of ratio of condensed to uncondensed degradation products). Suitable depolymerization conditions were found to be five hours reaction time at 174°C. The results were in general agreement with data reported by Pepper et al. and Miksche et al.

Keywords

Lignin Nitrobenzene Permanganate Cupric Oxide Product Mixture 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.
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References

  1. Brink, D. L., Wu, Y. T., Naveau, H. P., Bicho, J. G., Merriman, M. M. 1972. Tappi 55: 719Google Scholar
  2. Chang, H.-M., Allan, G. G. 1971. In: Sarkanen, K. V., Ludwig, C. H. Eds.:: Lignins—occurrence, formation, structure and reactions. New York:Wiley InterscienceGoogle Scholar
  3. Connors, W. J., Lorenz, L. F., Kirk, T. K. 1978. Holzforschung 32: 106Google Scholar
  4. Erickson, M., Larsson, S., Miksche, G. E. 1973a. Acta Chem. Scand. 27: 127Google Scholar
  5. Erickson, M., Larsson, S., Miksche, G. E. 1973b. Acta Chem. Scand. 27: 903Google Scholar
  6. Fischer, W. E., Lenz, B. L., Hider, S. A. 1972. Tappi 55: 234Google Scholar
  7. Freudenberg, K., Lautsch, W., Engler, K. 1940. Chem. Ber. 73: 167Google Scholar
  8. Freudenberg, K., Neish, A. C. 1968. Constitution and biosynthesis of lignin. New York: SpringerGoogle Scholar
  9. Freudenberg, K., Seib, K., Dall, K. 1959. Chem. Ber. 92: 807Google Scholar
  10. Holmberg, B. 1930. Svensk Papperstidn. 33: 679Google Scholar
  11. Larsson, S., Miksche, G. E. 1967. Acta Chem. Scand. 21: 1970Google Scholar
  12. Larsson, S., Miksche, G. E. 1971. Acta Chem. Scand. 25: 647Google Scholar
  13. Leopold, B. 1950. Acta Chem. Scand. 4: 1523Google Scholar
  14. Mogharab, I., Glasser, W. G. 1976. Tappi 59: 110Google Scholar
  15. Naveau, H. P., Wu, Y. T., Brink, D. L., Merriman, M. M., Bicho, J. G. 1972. Tappi 55: 1356Google Scholar
  16. Nimz, H. H. 1969. Chem. Ber. 102: 799 and 102: 3803Google Scholar
  17. Nimz, H. H., Das, K. 1971. Chem. Ber. 104: 2359Google Scholar
  18. Nimz, H., Das, K., Minemura, N. 1971. Chem. Ber. 104: 1871Google Scholar
  19. Pearl, I. A. 1942. J. Amer. Chem. Soc. 64: 1429Google Scholar
  20. Pepper, J. M., Casselman, B. W., Karapally, J. C. 1967. Can. J. Chem. 45: 3009Google Scholar
  21. Pepper, J. M., Karapally, J. C. 1972. Pulp Pap. Mag. Can. 73: T 232Google Scholar
  22. Pernemalm, P.-A., Dence, C. W. 1974: Acta Chem. Scand. 28B: 453Google Scholar
  23. Sarkanen, K. V., Ludwig, C. H., Eds. 1971: Lignins—occurrence, formation, structure and reactions. New York: Wiley InterscienceGoogle Scholar
  24. Shorygina, N. N. et al. Khim Ispol'z. Lignina 1974, 321; and Izv. Akad. Nauk SSSR, Otd. Khim. Nauk 4: 715 (1963); and Izv. Akad. Nauk SSSR, Ser Khim. 1: 187 (1971); through Abstr. Bull. of Inst. Pap. Chem. 46: 11185 (1976); ibid. 43: 10077 (1972); and ibid. 43: 10062 (1972)Google Scholar
  25. Yamaguchi, A. 1973. Mokuzai Gakkaishi 19: 95Google Scholar
  26. Yamaguchi, A. 1975. Mokuzai Gakkaishi 21: 422Google Scholar
  27. Yamaguchi, A., Miyazaki, H., Sakakibara, A. 1973. Mokuzai Gakkaishi 19: 23Google Scholar

Copyright information

© Springer-Verlag 1979

Authors and Affiliations

  • N. Morohoshi
    • 1
    • 2
    • 3
  • W. G. Glasser
    • 1
    • 2
  1. 1.Department of Forestry and Forest ProductsVirginia Polytechnic Institute and State UniversityBlacksburgVirginia
  2. 2.Department of Chemical EngineeringVirginia Polytechnic Institute and State UniversityBlacksburgVirginia
  3. 3.Wood Chemical Technology Department of Forest Products Faculty of AgricultureTokyo University of Agriculture and TechnologyFuchu, TokyoJapan

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