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Recent Developments in Lignin Chemistry

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Naturstoffe

Part of the book series: Fortschritte der Chemischen Forschung ((TOPCURRCHEM,volume 6))

Abstract

Work on lignin has now been going on for one-and-a-quarter centuries, and consequently the amount of information available on this natural material is now immense. The powerful new techniques of organic and physical chemistry and biochemistry introduced since the second world war that have brought so much progress in every other field of science have made their mark in lignin research too. For economic and academic reasons that will become apparent below, interest in lignin has been increasing of late; several hundred articles related directly or indirectly to lignin and involving almost every discipline of science appear annually in general or specialized scientific journals throughout the world.

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References

  1. Adler, E.: Recent Studies on the Structural Elements and the Reactions of Lignin. In (10), pp. 73-83.

    Google Scholar 

  2. Adler, E.: Studies on the Structural Elements of Lignin. Paperi ja Puu 43, 634–643 (1961).

    Google Scholar 

  3. Marton, J., and E. Adler: The Reactions of Lignin with Methanolic Hydrochloric Acid. A Discussion of Some Structural Questions. Tappi 46, 92–98 (1963).

    CAS  Google Scholar 

  4. Adler, E.: Über den Stand der Ligninforschung. Das Papier 15, 604–609 (1961).

    CAS  Google Scholar 

  5. Adler, E., K. J. Bjorkquist, S. Häggroth u. L. Ellmer: Coniferylaldehydgruppen im Holz und in isolierten Ligninpräparaten. Acta Chem. Scand. 2, 93-94, 839–840 (1948).

    Article  Google Scholar 

  6. Adler, E. and K. Lundquist: Spectrochemical Estimations of Phenylcoumaran Elements in Lignin. Acta Chem. Scand. 17, 13–26 (1963).

    Article  CAS  Google Scholar 

  7. Adler, E. and J. Marton: Carbonyl Groups in Lignin. Acta Chem. Scand. 13, 75–96 (1959).

    Article  CAS  Google Scholar 

  8. Adler, E. and J. Marton: Carbonyl Groups in Lignin. Acta Chem. Scand. 15, 357–392 (1961).

    Article  CAS  Google Scholar 

  9. Adler, E. and J. Marton, I. Falkehag, H. Halvarson, and B. Wesslen: The Behavior of Lignin in Alkaline Pulping. Acta Chem. Scand. 18, 1311–1316 (1964).

    Article  CAS  Google Scholar 

  10. Adler, E. H.-D. Becker, T. Ishihara u. A. Stamvik: Über die Benzylalkoholgruppen des Fichtenlignins. Holzforschung 20, 3–11 (1966).

    Article  CAS  Google Scholar 

  11. Adler, E. H.-D. Becker, T. Ishihara u. A. Stamvik: Cf. Acta Chem. Scand. 15, 218, 849 (1961).

    Google Scholar 

  12. Allen, C. F. H., and J. R. Byers: A Synthesis of Coniferyl Alcohol. J. Amer. chem. Soc. 71, 2683–2684 (1949).

    Article  CAS  Google Scholar 

  13. Anon.: Chemicals from the Other Half of the Tree. Chem. Engng. News 41, No. 6, 83-89 (1963).

    Google Scholar 

  14. Anon. (Editor): Chimie et Biochimie de la Lignine, de la Cellulose et des Hemicelluloses. Actes du Symposium International de Grenoble. Les Imprimeries Réunies de Chambéry, 1965.

    Google Scholar 

  15. Aulin-Erdtman, G., and L. Hegbom: Spectrographic Contributions to Lignin Chemistry. Svensk Pappertid. 61, 187–210 (1958).

    CAS  Google Scholar 

  16. Aulin-Erdtman, G., and L. Hegbom: Spectrographic Contributions to Lignin Chemistry. Svensk Pappertid. 60, 671–681 (1957).

    CAS  Google Scholar 

  17. Aulin-Erdtman, G., and L. Hegbom: Spectrographic Contributions to Lignin Chemistry. Svensk Pappertid. 59, 363–371 (1956).

    CAS  Google Scholar 

  18. Aulin-Erdtman, G., and L. Hegbom: Spectrographic Contributions to Lignin Chemistry. Svensk Pappertid. 56, 91, 287 (1953).

    CAS  Google Scholar 

  19. Aulin-Erdtman, G., and L. Hegbom: Spectrographic Contributions to Lignin Chemistry. Svensk Pappertid. 55, 745 (1952).

    CAS  Google Scholar 

  20. Aulin-Erdtman, G., Y. Tomita, and S. Forsén: The Configuration of Dehydrodiisoeugenol. Acta Chem. Scand. 17, 535–536 (1963).

    Article  CAS  Google Scholar 

  21. Bailey, A. J.: Lignin in Douglas Fir. The Pentosan Content of the Middle Lamella. Ind. Engng. Chem. Anal. Edit. 52, 389–391 (1936).

    Article  Google Scholar 

  22. Barnoud, F.: Sur la Lignine Elaboré par les Tissus d’Arbres Cultivés in vitro. C. R. hebd. Séances Acad Sci. (France) 253, 1848–1851 (1961).

    Google Scholar 

  23. Bland, D.E., and S. Sternhell: Aromatic Protons in Methanol Lignins. Austral. J. Chem. 18, 401 (1965).

    Article  CAS  Google Scholar 

  24. Berry, J. W., A. Ho, and C. Steelink: Constituents of the Saguaro. Proximate Analysis of the Woody Tissues. J. Org. Chem. 25, 1267–1268 (1960).

    Article  Google Scholar 

  25. Björkman, A.: Studies on Finely Divided Wood. Svensk Papperstid. 59, 477–485 (1956).

    Google Scholar 

  26. Björkman, A.: Studies on Finely Divided Wood. Svensk Papperstid. 60, 158-161, 243-251, 285-292, 329–335 (1957).

    Google Scholar 

  27. Björkman, A.: Cf.Nature [London] 174, 1057 (1954).

    Article  Google Scholar 

  28. Björkman, A.: On the Mechanism and Macrokinetics of the Sulfite Cook. In (10), pp. 317-326.

    Google Scholar 

  29. Bolker, H. I.: A Lignin-Carbohydrate Bond as Revealed by Infrared Spectroscopy. Nature 197, 489–490 (1963).

    Article  CAS  Google Scholar 

  30. Brauns, F. E.: The Chemistry of Lignin. Academic Press, New York, 1952.

    Google Scholar 

  31. Brauns, F. E. and D. A. Brauns: The Chemistry of Lignin. Supplementary Volume. Academic Press, New York, 1960.

    Google Scholar 

  32. Britt, K. W.: Handbook of Pulp and Paper Technology. Reinhold, New York, 1964.

    Google Scholar 

  33. Brown, S. A.: Lignin and Tannin Biosynthesis. In (70), pp.361-398.

    Google Scholar 

  34. Brown, S. A.: Chemistry of Lignification. Science [Washington] 134, 305–313 (1961).

    Article  CAS  Google Scholar 

  35. Brown, S. A.: Aspects of the Biosynthesis of Lignin Monomers. In (10), pp. 247 to 254.

    Google Scholar 

  36. Brown, S. A. and A. C. Neish: Shikimic Acid as a Precursor in Lignin Biosynthesis. Nature [London] 175, 688–689 (1955).

    Article  CAS  Google Scholar 

  37. Brown, S. A. and A. C. Neish: Cf. Can. J. Biochem. Physiol. 33, 948–962 (1955).

    Article  CAS  Google Scholar 

  38. Casey, J. P.: Pulp and Paper Chemistry and Chemical Technology. Interscience, New York, 1960.

    Google Scholar 

  39. Casperson, G.: Zur Anatomie des Reaktionsholzes. Svensk Papperstid. 68, 534–544 (1965).

    CAS  Google Scholar 

  40. Chen, C.-L., unpublished results.

    Google Scholar 

  41. Conn, E. E.: Enzymology of Phenolic Biosynthesis. In (70), pp. 399 to 435.

    Google Scholar 

  42. Coscia, C. J., M. I. Ramirez, W. J. Schubert, and F. F. Nord: Studies on the Utilization of Pyruvate in Lignification. Biochem. 1, 447–451 (1962).

    Article  CAS  Google Scholar 

  43. Côté, W. A. (Editor): Cellular Ultrastructure of Woody Plants. Syracuse University Press, 1965.

    Google Scholar 

  44. Cousin, H., and H. Hérissey: Oxidation de l’Isoeugenol. Sur la Dehydrodiisoeugenol. C. R. hebd. Séances Acad. Sci. (France) 147, 247 (1908).

    CAS  Google Scholar 

  45. Cousin, H., and H. Hérissey: Bull. Soc. Chim. France 3, 1070 (1908).

    Google Scholar 

  46. Cousin, H., and H. Hérissey: J. Pharmac. Chim. 28, 93 (1908).

    Google Scholar 

  47. Davis, B. D.: Intermediates in Amino Acid Biosynthesis. Adv. Enzymol. 16, 247 (1955).

    CAS  Google Scholar 

  48. Davis, B. D.: Arch. Biochem. Biophys. 78, 497–509 (1958).

    Article  CAS  Google Scholar 

  49. DeStevens, G., and F. F. Nord: Fortschr. chem. Forsch. 3, 95–107 (1954).

    Google Scholar 

  50. Eberhardt, G., and W. J. Shubert: Investigations on Lignin and Lignification XVII. Evidence for the Mediation of Shikimic Acid in the Biogenesis of Lignin Building Stones. J. Amer. chem. Soc. 78, 2835–2837 (1956).

    Article  CAS  Google Scholar 

  51. Enkvist, T.: What Shall We Make from Lignin? Tek. Forum 1961, 543-6.

    Google Scholar 

  52. Enkvist, T.: Suomen Kemistilehti 36 A, 51 (1963).

    Google Scholar 

  53. El-Basyouni, S.Z., A. C. Neish, and G. H. N. Towers: The Phenolic Acids in Wheat III. Insoluble Derivatives of Phenolic Cinnamic Acids as Natural Intermediates in Lignin Biosynthesis. Phytochem. 3, 627–640 (1964).

    Article  CAS  Google Scholar 

  54. Erdtman, H.: Dehydrierungen in der Coniferylreihe. Biochem. Z. 258, 172–180 (1933).

    CAS  Google Scholar 

  55. Erdtman, H.: Liebigs Ann. Chem. 503, 283–294 (1933).

    CAS  Google Scholar 

  56. Fåhraeus, G., V. Tullander, and H. Ljunggren: Production of High Laccase Yields in Cultures of Fungi. Physiologia Plantarum 11, 631 to 643 (1958).

    Google Scholar 

  57. Flaig, W.: Zur Umwandlung von Lignin in Humusstoffe. Freiberger Forschungsh. A 254, 39–56 (1962).

    Google Scholar 

  58. Flaig, W.: Chemische Untersuchungen an Humusstoffen. Z. Chem. 4, 253–265 (1964).

    Article  CAS  Google Scholar 

  59. Flaig, W. and H. Haider: Die Verwertung phenolischer Verbindungen durch Weißfäulepilze. Archiv. Mikrobiol. 40, 212–223 (1962).

    Article  Google Scholar 

  60. Flaig, W. and H. Haider: Planta Medica 9, 124–139 (1961).

    Article  Google Scholar 

  61. Forss, K., and K. E. Fremer: The Repeating Unit in Spruce Lignin. Paperi ja Puu 47, 443–454 (1965).

    CAS  Google Scholar 

  62. Freudenberg, K.: Analytical and Biochemical Background of a Constitutional Scheme of Lignin. Advances in Chemistry Series 1966, in the press.

    Google Scholar 

  63. Freudenberg, K.: Contribution à l’Etude de la Chimie et de la Biogenese de la Lignine. In (10), pp. 39-50.

    Google Scholar 

  64. Freudenberg, K.: Lignin: its Constitution and Formation from p-Hydroxycinnamyl Alcohols. Science [Washington] 148, 595–600 (1964).

    Article  Google Scholar 

  65. Freudenberg, K.: Entwurf eines Konstitutionsschemas für das Lignin der Fichte. Holzforschung 18, 3–9 (1964).

    Article  CAS  Google Scholar 

  66. Freudenberg, K.: Neuere Ergebnisse auf dem Gebiet des Lignins und der Verholzung. Fortschritte der Chem. org. Naturstoffe 11, 43–82 (1954).

    CAS  Google Scholar 

  67. Freudenberg, K.: Lignin. In K. Paech and M. V. Tracey (Editors): Modern Methods of Plant Analysis. Springer Verlag, Berlin-Göttingen-Heidelberg, 1955, Vol. III, pp. 499-516.

    Google Scholar 

  68. Freudenberg, K.: Forschungen am Lignin. Fortschritte der Chem. org. Naturstoffe 20, 41–72 (1962).

    CAS  Google Scholar 

  69. Freudenberg, K., C.-L. Chen, and G. Cardinale: Die Oxydation des methylierten natürlichen und künstlichen Lignins. Chem. Ber. 95, 2814–2828 (1962).

    Article  CAS  Google Scholar 

  70. Freudenberg, K.: Die Oxydation des methylierten natürlichen und künstlichen Lignins. Chem. Ber. 93, 2533–2539 (1960).

    Article  CAS  Google Scholar 

  71. Freudenberg, K., C.-L. Chen, J. M. Harkin, H. Nimz, and H. Renner: Observations on Lignin. Chem. Commun. 1965, 224-225.

    Google Scholar 

  72. Freudenberg, K. and M. Friedmann: Oligomere Zwischenprodukte der Ligninbildung. Chem. Ber. 93, 2138–2148 (1960).

    Article  CAS  Google Scholar 

  73. Freudenberg, K. and W. Fuchs: Anwendung Radioaktiver Isotope bei der Erforschung des Lignins IV. Chem. Ber. 87, 1824–1834 (1954).

    Article  CAS  Google Scholar 

  74. Freudenberg, K. and H. Geiger: Pinoresinolid und anderer Zwischenprodukte der Ligninbildung. Chem. Ber. 96, 1265–1270 (1963).

    Article  CAS  Google Scholar 

  75. Freudenberg, K. and G. Grion: Beitrag zum Bildungsmechanismus des Lignins und der Lignin-Kohlenhydrat-Bindung. Chem. Ber. 92, 1355–1363 (1959).

    Article  CAS  Google Scholar 

  76. Freudenberg, K., and G. Grion and J. M. Harkin: Nachweis von Chinonmethiden bei der enzymatischen Bildung des Lignins. Angew. Chem. 70, 743 (1958).

    Article  CAS  Google Scholar 

  77. Freudenberg, K. and J. M. Harkin: Modelle für die Bindung des Lignins an die Kohlenhydrate. Chem. Ber. 93, 2814–2819 (1960).

    Article  CAS  Google Scholar 

  78. Freudenberg, K. and J. M. Harkin: The Glucosides of Cambial Sap of Spruce. Phytochem. 2, 189–193 (1963).

    Article  CAS  Google Scholar 

  79. Freudenberg, K. and J. M. Harkin: Ergänzung des Konstitutionsschemas für das Lignin der Fichte. Holzforschung 18, 166–168 (1964).

    Article  CAS  Google Scholar 

  80. Freudenberg, K. and J. M. Harkin, M. Reichert, and T. Fukuzumi: Die an der Verholzung beteiligten Enzyme. Die Dehydrierung des Sinapinalkohols. Chem. Ber. 91, 581 to 590 (1958).

    Google Scholar 

  81. Freudenberg, K. and J. M. Harkin and H.-K. Werner: Das Vorkommen von Benzylaryläthern im Lignin. Naturwiss. 50, 476–477 (1963).

    Article  CAS  Google Scholar 

  82. Freudenberg, K. and J. M. Harkin and H.-K. Werner: Chem. Ber. 97, 909–920 (1964).

    Article  CAS  Google Scholar 

  83. Freudenberg, K., K. Jones u. H. Renner: Radioaktive Isotope und Lignin, IX. Künstliches Lignin aus markiertem Coniferylalkohol. Chem. Ber. 96, 1844–18 (1963).

    Article  CAS  Google Scholar 

  84. Freudenberg, K. and V. Jovanovic: Weitere Versuche mit deuteriertem Coniferylalkohol. Chem. Ber. 96, 2178–2181 (1963).

    Article  CAS  Google Scholar 

  85. Freudenberg, K. and V. Jovanovic: Weitere Versuche mit deuteriertem Coniferylalkohol. Chem. Ber. 94, 3227–3238 (1961).

    Article  CAS  Google Scholar 

  86. Freudenberg, K., W. Lautsch, and K. Engler: Die Bildung von Vanillin aus Fichtenlignin, Ber. dtsch. chem. Ges. 73, 167–171 (1940).

    Google Scholar 

  87. Freudenberg, K. and B. Lehmann: Aldehydische Zwischenprodukte der Ligninbildung. Chem. Ber. 93, 1354–1366 (1960).

    Article  CAS  Google Scholar 

  88. Freudenberg, K. and K. C. Renner: Biphenyle und Diaryläther unter den Vorstufen des Lignins. Chem. Ber. 98, 1879–1892 (1965).

    Article  CAS  Google Scholar 

  89. Freudenberg, K. and F. Niedercorn: Umwandlung von Phenylalanin in Coniferin und Fichtenlignin. Chem. Ber. 91, 591–597 (1958).

    Article  CAS  Google Scholar 

  90. Freudenberg, K., H. Reznik, W. Fuchs, and M. Reichert: Untersuchungen über die Entstehung des Lignins. Naturwiss. 42, 29–35 (1955).

    Article  CAS  Google Scholar 

  91. Freudenberg, K. and H. Richtzenhain: Enzymatische Versuche zur Entstehung des Lignins. Ber. dtsch. chem. Ges. 76 B, 997–1006 (1943).

    Article  Google Scholar 

  92. Freudenberg, K. and A. Sakakibara: Dehydrodipinoresinol. Weitere Zwischenprodukte der Bildung des Lignins. Liebigs Ann. Chem. 623, 129–137 (1959).

    Article  CAS  Google Scholar 

  93. Freudenberg, K. and H. Schlüter: Weitere Zwischenprodukte der Ligninbildung. Chem. Ber. 88, 617–625 (1955).

    Article  CAS  Google Scholar 

  94. Freudenberg, K. and G. S. Sidhu: Die absolute Konfiguration des Sesamins und Pinoresinols. Tetrahedron Letters 1960, No. 20, 3-6; Chem. Ber. 94, 851–862 (1961).

    CAS  Google Scholar 

  95. Freudenberg, K. and H.-K. Werner: Die Polymerisation der Chinonmethide. Chem. Ber. 97, 579–587 (1964).

    Article  CAS  Google Scholar 

  96. Frey-Wyssling, A.: Die pflanzliche Zellwand, Springer-Verlag, Berlin-Göttingen-Heidelberg, 1959.

    Google Scholar 

  97. Freudenberg, K.: Ultraviolet and Fluorescence Optics of Lignified Cell Walls. In (153), pp. 153-167.

    Google Scholar 

  98. Fukuzumi, T.: Enzymic Degradation of Lignins. Bull. Agric. Chem. Soc. Japan 24, 728–736 (1960).

    Article  CAS  Google Scholar 

  99. Fukuzumi, T., and T. Shibamoto: Enzymatic Degradation of Lignin IV. Splitting of Veratrylglycerol-β-guaiacyl Ether by Enzyme of Poria subacida. Nippon Mokuzai Gakkaishi. (J. Japan Wood Research Soc.) 11, 248–252 (1965).

    CAS  Google Scholar 

  100. Gierer, J., and H.-F. Huber: The Reactions of Lignin during Bleaching. Acta Chem. Scand. 18, 1237–1243 (1964).

    Article  CAS  Google Scholar 

  101. Freudenberg, K., et al.: Reactions of Lignin during Sulfate Cooking. Svensk Pappertid. 68, 334–338 (1965).

    Google Scholar 

  102. Freudenberg, K., et al.: Acta Chem. Scand. 19, 1103–1112, 1502-1503 (1965).

    Article  Google Scholar 

  103. Freudenberg, K., et al.: Acta Chem. Scand. 18, 1469 (1964).

    Article  Google Scholar 

  104. Goheen, D. W.: Hydrogenation of Lignin by the Noguchi Process. Abstract E 15, 150th Meeting Amer. Chem. Soc. 1965, p. 8E.

    Google Scholar 

  105. Goldschmidt, O., and H. L. Hergert: Examination of Western Hemlock for Lignin Precursors. Tappi 44, 858–870 (1961).

    Google Scholar 

  106. Hall, L.: Lignosulfonate as a Dispersing Agent. Svensk Papperstid. 60, 199–210 (1957).

    CAS  Google Scholar 

  107. Harborne, J. B. (Editor): Biochemistry of Phenolic Compounds. Academic Press, London-New York, 1964.

    Google Scholar 

  108. Harkin, J. M.: Unpublished results.

    Google Scholar 

  109. Harris, E. E., J. D’Ianni, and H. Adkins: Reaction of Hardwood Lignin with Hydrogen. J. Amer. chem. Soc. 60, 1467–1470 (1938).

    Article  CAS  Google Scholar 

  110. Hartler, N.: Increased Yields during Sulfate Cooking. Svensk Pappertid. 68, 369–377 (1965).

    CAS  Google Scholar 

  111. Freudenberg, K.: Sulfate Cooking with the Addition of Reducing Agents. Svensk Papperstid. 62, 467–470 (1959).

    Google Scholar 

  112. Freudenberg, K.: Sulfate Cooking with the Addition of Reducing Agents. Svensk Papperstid. 65, 513–520 (1962).

    Google Scholar 

  113. Hasegawa, M., and T. Higuchi: Formation of Lignin from Glucose in Eucalyptus. J. Jap. Forest. Soc. 42, 305–308 (1960).

    CAS  Google Scholar 

  114. Hearon, W. M., W. S. MacGregor, and D. W. Goheen: Sulfur Chemicals from Lignin. Tappi 45, 28 A, 30 A, 34 A, 36 A (1962).

    Google Scholar 

  115. Helferich, B., and T. Kleinschmidt: Über die Hemmung der ß-D-Glucosidase aus Süßmandelemulsin durch Mistelextrakt. Z. Physiol. Chem. 315, 34–37 (1959).

    Article  CAS  Google Scholar 

  116. Higuchi, T.: Further Studies on the Phenol Oxidase Related to Lignin Biosynthesis. J. Biochem. 45, 515–528 (1958).

    CAS  Google Scholar 

  117. Hibbert, H. et al.: Studies on Lignin and Related Compounds. J. Amer. chem. Soc. 66, 37–44 (1944).

    Article  Google Scholar 

  118. Hibbert, H. et al.: Studies on Lignin and Related Compounds. J. Amer. chem. Soc. 63, 3045–3068 (1941).

    Article  Google Scholar 

  119. Hibbert, H. et al.: Studies on Lignin and Related Compounds. J. Amer. chem. Soc. 61, 509 to 520 (1939).

    Article  Google Scholar 

  120. Higuchi, T.: Studies of Lignin using Isotopic Carbon X [cf. (25)]. Formation of Lignin from Phenylpropanoids in Tissue Culture of White Pine. Canad. J. Biochem. Physiol. 40, 31–34 (1962).

    Article  CAS  Google Scholar 

  121. Freudenberg, K.: Biochemical Studies of Lignin Formation. Physiologia Plantarum 10. 633–648 (1957).

    Article  Google Scholar 

  122. Freudenberg, K. and F. Barnoud: Les Lignines dans les Tissus Végétaux Cultivés in vitro. In (10), pp. 255-274.

    Google Scholar 

  123. Freudenberg, K. Cf. C. R. hebd. Séances Acad. Sci. [France] 259, 3824–3825, 4339-4341 (1964).

    Google Scholar 

  124. Freudenberg, K. and F. Barnoud and A. Robert: La Biosynthese des Lignines. Bulletin A.T.I.P. 18, 91–104 (1964).

    Google Scholar 

  125. Freudenberg, K. and I. Kawamura: Enzymes of Aromatic Biosynthesis. In Linskens, H. F. B.D. Sanwal, and M. V. Tracey (Editors): Modern Methods of Plant Analysis, Springer Verlag, Berlin-Göttingen-Heidelberg, 1964. Vol. 7, pp. 260–289.

    Google Scholar 

  126. Isherwood, F. A.: Biosynthesis of Lignin. In Pridham, J. B., and T. Swain (Editors): Biosynthetic Pathways in Higher Plants. Academic Press, London-New York, 1965.

    Google Scholar 

  127. Ishikawa, H., W. J. Schubert, and F. F. Nord: The Enzymatic Degradation of Softwood Lignin by White Rot Fungi. The Degradation by Polyporus versicolor and Fomes fomentarius of Aromatic Compounds Structurally Related to Softwood Lignin. Arch. Biochem. Biophys. 100, 131–149 (1963).

    Article  CAS  Google Scholar 

  128. Kawamura, I., and T. Higuchi: Comparative Studies of Milled Wood Lignins from Different Taxonomical Origins by Infrared Spectroscopy. In (10), pp. 439-456.

    Google Scholar 

  129. Kirk, K. T., and A. Kelman: Lignin Degradation as Related to the Phenol Oxidases of Selected Wood-Decaying Basidiomycetes. Phyto-pathol. 55, 739–745 (1965).

    CAS  Google Scholar 

  130. Klason, P.: Beiträge zur Konstitution des Fichtenlignins. Ber. dtsch. chem. Ges. 56, 300–308 (1923).

    Article  Google Scholar 

  131. Klason, P.: Beiträge zur Konstitution des Fichtenlignins. Ber. dtsch. chem. Ges. 62, 635-639, 2523–2526 (1929).

    Article  Google Scholar 

  132. Klason, P.: Cellulosechemie 13, 113 (1932).

    CAS  Google Scholar 

  133. Kleinert, T. N.: Alkaline Pulping Studies VI. Discussion of Results and the Principles of Rapid Delignification. Tappi 48, 477–451 (1965).

    Google Scholar 

  134. Koblitz, H.: Chemisch-physiologische Untersuchungen an pflanzlichen Zellwänden. Flora 154, 511–546 (1964).

    CAS  Google Scholar 

  135. Krazl, K.: On the Biosynthesis of Gymnospermae and Angiospermae Lignins. Tappi 43, 650–653 (1960).

    Google Scholar 

  136. Krazl, K.: Lignin — its Biochemistry and Structure. In (30), pp. 157-180.

    Google Scholar 

  137. Krazl, K.: Probleme der Holzchemie. Holzforschung und Holzverwertung 15, 23–30 (1963).

    Google Scholar 

  138. Krazl, K.: Zur Biogenese des Lignins. Holz als Roh-und Werkstoff 19, 219–232 (1961).

    Article  Google Scholar 

  139. Krazl, K.: Ligninverwertung. Österr. Chem.-Ztg. 62, 102–115 (1961).

    Google Scholar 

  140. Krazl, K. and G. Billek (Editors): Biochemistry of Wood. Pergamon Press, London (1959).

    Google Scholar 

  141. Krazl, K. and H. Czepel: Untersuchungen der Äthanolyseprodukte von Fichtenholzlignin mit Hilfe der Gaschromatographie. Monatsh. Chem. 95, 1609 to 1612 (1964).

    Google Scholar 

  142. Krazl, K. and H. Faigl: Einbau von d-Glucose in das Phenylpropangerüst von Fichtenlignin. Monatsh. Chem. 90, 768–770 (1959).

    Article  Google Scholar 

  143. Krazl, K. and H. Faigl: Z. Naturf. 15b, 4 (1960).

    Google Scholar 

  144. Krazl, K. and G. Puschmann: Präparative Trennungen mit Hilfe der Dünnschichtchromatographie. Holzforschung 14, 1–4 (1960).

    Article  Google Scholar 

  145. Krazl, K. and J. Zauner: Über den biologischen Einbau von Xylit in Holz und seine Konstituenten. Holzforschung und Holzverwertung 14, 108–111 (1962).

    Google Scholar 

  146. Kremers, R. E.: Cambial Chemistry. Tappi 47, 292–296 (1964).

    CAS  Google Scholar 

  147. Kremers, R. E.: Analysis of Stone Cells, Tappi 44, 747–748 (1961).

    Google Scholar 

  148. Kürschner, K.: Die Chemie des Holzes. Deutscher Verlag der Wissenschaften, Berlin 1962, pp. 91-116.

    Google Scholar 

  149. Kremers, R. E.: Betrachtungen zum gegenwärtigen Stand der Holzforschung. Holzforschung 18, 65–76 (1964).

    Article  Google Scholar 

  150. Lange, P. W.: Ultraviolet Absorption of Solid Lignin. Svensk Papperstid. 48, 241–245 (1945).

    CAS  Google Scholar 

  151. Lange, P. W.: Ultraviolet Absorption of Solid Lignin. Svensk Papperstid. 47, 262 (1944).

    CAS  Google Scholar 

  152. Lange, P. W.: Ultraviolet Absorption of Solid Lignin. Svensk Papperstid. 57, 235, 501, 525, 533, 563 (1954).

    CAS  Google Scholar 

  153. Leopold, B.: Studies on Lignin. Acta Chem. Scand. 6, 38–63 (1952).

    Article  Google Scholar 

  154. Levin, J. G., and D. B. Sprinson: Formation of 3-Enolpyruvyl Shikimate 5-Phosphate in Extracts of E. coli. Biochem. Biophys. Res. Commun. 3, 157 (1960).

    Article  CAS  Google Scholar 

  155. Libbey, C.E. Pulp and Paper Science and Technology. McGraw-Hill, New York 1962.

    Google Scholar 

  156. Ludwig, C. H., B. J. Nist, and J. L. McCarthy: High Resolution NMR Spectroscopy of Protons in Compounds Related to Lignin and in Acetylated Lignins. J. Amer. chem. Soc. 86, 1186–1202 (1964).

    Article  CAS  Google Scholar 

  157. Lundquist, K.: The Separation of Lignin Degradation Products. Acta Chem. Scand. 18, 1316–1317 (1964).

    Article  CAS  Google Scholar 

  158. Lundquist, K. and G. E. Miksche: Nachweis eines neuen Verknüpfungsprinzips von Guajacylpropaneinheiten im Fichtenlignin. Tetrahedron Letters 1965, 2131-2136.

    Google Scholar 

  159. Lyr, H.: Über den Nachweis von Oxydasen und Peroxydasen bei höheren Pilzen und die Bedeutung dieser Enzyme für die Bavendamm Reaction. Planta 50, 359–370 (1958).

    Article  CAS  Google Scholar 

  160. Lundquist, K. and W. Gillwald (Editors): Holz-Zerstörung durch Pilze. Akademie Verlag, Berlin 1963.

    Google Scholar 

  161. Marton, J., and T. Marton: The Structure and Molecular Weight of Kraft Lignin. Tappi 47, 713-719, 471–476 (1964).

    Google Scholar 

  162. Mason, H. S.: Mechanism of Oxygen Metabolism. Adv. Enzymol. 19, 79–233 (1957).

    CAS  Google Scholar 

  163. Mason, H. S.: Mechanism of Oxygen Metabolism. Adv. Enzymol. 16, 105 (1955).

    CAS  Google Scholar 

  164. Mason, H. S.: Oxidases. Ann. Revs. Biochem. 34, 595–634 (1965).

    Article  CAS  Google Scholar 

  165. Merewether, J. W. T.: The Lignin Carbohydrate Complex. Holzforschung 11, 65–80 (1957) and in (21), pp. 630 et seq.

    Article  Google Scholar 

  166. Nakano, J., S. Miyao, C. Takatsuka, and N. Migata: Polysulfide Cooking. Nippon Mokuzai Gakkaishi 10, 141–146 (1964).

    CAS  Google Scholar 

  167. Neish, A. C.: Major Pathways of Biosynthesis of Phenols. In (70), pp. 295-359.

    Google Scholar 

  168. Neish, A. C.: Cinnamic Acid Derivatives as Intermediates in the Biosynthesis of Lignin and Related Compounds. In (153), pp. 219-239.

    Google Scholar 

  169. Neish, A. C.: Ann. Revs. Plant Physiol. 11, 55 (1960).

    Article  CAS  Google Scholar 

  170. Nelson, C. D.: The Production and Translocation of Photosynthate-14C in Conifers. In (153), pp. 243-257.

    Google Scholar 

  171. Neperin, Y. N.: Chemie und Technologie der Zellstoffherstellung. Akademie Verlag, Berlin, 1960.

    Google Scholar 

  172. Nirnz, H.: Über die milde Hydrolyse des Buchenlignins. Chem. Ber. 98, 3153–3165 (1965).

    Article  Google Scholar 

  173. Nirnz, H.: Unpublished results.

    Google Scholar 

  174. Nord, F. F., and W. J. Schubert: The Biochemistry of Lignin Formation. In Florkin, M., and H. S. Mason: Comparative Biochemistry. Academic Press, New York-London 1962, Vol. 4, pp. 65–106.

    Google Scholar 

  175. Nord, F. F.: The Biogenesis of Lignins. In P. Bernfeld: Biogenesis of Natural Compounds. Macmillan, New York, 1963, pp. 693–726.

    Google Scholar 

  176. Olcay, A.: Hydrogenation Products of Spruce Milled-Wood Lignin and of Related Model Compounds. Holzforschung 17, 105–110 (1963).

    Article  CAS  Google Scholar 

  177. Olcay, A.: J. Org. Chem. 27, 1783–1786 (1962).

    Article  CAS  Google Scholar 

  178. Pearl, I. A.: Annual Reviews of Lignin Chemistry. Forest Products J. 14, 435–445 (1964).

    CAS  Google Scholar 

  179. Pearl, I. A.: Annual Reviews of Lignin Chemistry. Forest Products J. 13, 373–385 (1963).

    CAS  Google Scholar 

  180. Pearl, I. A.: Annual Reviews of Lignin Chemistry. Forest Products J. 12, 141–150 (1962).

    CAS  Google Scholar 

  181. Pearl, I. A. and J. W. Rowe: Progress in the Chemical Conversion and Utilization of Lignin. Forest Prod. J. 11, 85–107 (1961).

    Google Scholar 

  182. Pearl, I. A. and J. W. Rowe: Progress in the Chemical Conversion and Utilization of Lignin. Forest Prod. J. 10, 91–112 (1960).

    CAS  Google Scholar 

  183. Peckham, J. R., and M. N. May: The Use of Polysulfides in the Kraft Pulping Process. Tappi 43, 45–48 (1960).

    CAS  Google Scholar 

  184. Pew, J. C.: Biphenyl Groups in Lignin. Nature [London] 193, 250–252 (1962).

    Article  CAS  Google Scholar 

  185. Pew, J. C.: J. Org. Chem. 28, 1048–1054 (1963).

    Article  CAS  Google Scholar 

  186. Pew, J. C., W. B. Conners, and A. Kunishi: Enzymatic Dehydrogenation of Lignin Model Phenols. In (10), pp. 229-245.

    Google Scholar 

  187. Robert, A., and F. Barnoud: Determination Quantitative de la Lignification dans les Cultures de Tissus Végétaux. C. R. hebd. Séances Acad. Sci. (France) 253, 1609–1610 (1961).

    CAS  Google Scholar 

  188. Robert, A., and F. Barnoud: Determination Quantitative de la Lignification dans les Cultures de Tissus Végétaux. C. R. hebd. Séances Acad. Sci. (France) 259, 3824-3825, 4339–4341 (1964).

    Google Scholar 

  189. Roelofsen, P. A.: The Plant Cell Wall. Verlag Gebrüder Borntraeger, Berlin, 1959.

    Google Scholar 

  190. Rüssel, J. D., M. E. K. Henderson, and V. C. Farmer: Metabolism of Lignin Model Compounds by Polystictüs versicolor. Biochem. Biophys. Acta 52, 565–570 (1961).

    Article  Google Scholar 

  191. Rydholm, S. A.: Pulping Processes. Interscience Publishers, New York-London-Sydney, 1964.

    Google Scholar 

  192. Sandermann, W.: Grundlagen der Chemie und Chemische Technologie des Holzes, Verlag Geest und Portig, Leipzig. 1956. Chemische Holzverwertung, München, 1963.

    Google Scholar 

  193. Sarkanen, K. V.: Wood Lignins. In Browning, B. L. (Editor): The Chemistry of Wood. Interscience Publishers, New York-London, 1963, pp. 249–311.

    Google Scholar 

  194. Sato, K., and H. Mikawa: The Mechanism of Pulp Bleaching. Bull. Chem. Soc. Japan. 35, 477–486 (1962).

    Article  CAS  Google Scholar 

  195. Sergeeva, V. N., and Z. N. Kreicberga: The Participation of Pentoses in the Formation of Lignin. Chem. Abstr. 52, 1070 (1958).

    Google Scholar 

  196. Schubert, W. J.: Lignin Biochemistry. Academic Press, New York-London, 1965.

    Google Scholar 

  197. Schubert, W. J. and S. N. Acerbo: Conversion of d-Glucose into Lignin in Norwegian Spruce. Arch. Biochem. Biophys. 83, 178–182 (1959).

    Article  CAS  Google Scholar 

  198. Schubert, W. J. and S. N. Acerbo: J. Amer. chem. Soc. 82, 735–739 (1960).

    Article  Google Scholar 

  199. Schuerch, C., M. P. Burdick, M. Mahdalik, and R. E. Pentoney: Liquid Ammonia-Solvent Combinations in Wood Plasticization. Abstracts E 28 and E 29, 150th Meeting Am. Chem. Soc. 1965, p. 13 E.

    Google Scholar 

  200. Schütz, F., P. Sarten, and H. Meyer: Lignin Problem and Complete Solution of Wood. Holzforschung 1, 2–20 (1947).

    Article  Google Scholar 

  201. Schütz, F., P. Sarten, and H. Meyer: Holzchemie III. Angew. Chem. 60, 115–125 (1948).

    Article  Google Scholar 

  202. Shorygina, N. N., and T. Y. Kefeli: Cleavage of Lignin with Metallic Sodium in Liquid Ammonia. Zhur. Obshch. Khim. 18, 528 (1948).

    CAS  Google Scholar 

  203. Shorygina, N. N., and T. Y. Kefeli: Cleavage of Lignin with Metallic Sodium in Liquid Ammonia. Zhur. Obshch. Khim. 19, 2558 (1949); 20, 1199 (1950).

    Google Scholar 

  204. Simionescu, C., and M. Grigoras: Über die Veränderung in der chemischen Zusammensetzung des Holzes verursacht durch Pflanzenkrebs. Paperi ja Puu 39, 283–284 (1957).

    CAS  Google Scholar 

  205. Smith, D. G., and A. C. Neish: Alkaline Oxidation of 14C-Labelled Protolignin Formed from Cinnamic Acid in Spruce and Aspen Twigs. Phytochem. 3, 609–616 (1964).

    Article  CAS  Google Scholar 

  206. Stamm, A. J., and E. E. Harris: Chemical Processing of Wood. Chemical Publishing Co., New York, 1953.

    Google Scholar 

  207. Steelink, C.: What is Humic Acid? J. Chem. Educ. 40, 379–384 (1963).

    Article  CAS  Google Scholar 

  208. Steelink, C., G. Tollin, and T. Reid: The Nature of the Free Radical Moiety in Lignin, J. Amer. chem. Soc. 85, 4048–4049 (1963).

    Article  CAS  Google Scholar 

  209. Steelink, C., G. Tollin, and T. Reid: Geochem. Cosmochim. Acta 28, 1615 (1964).

    Article  CAS  Google Scholar 

  210. Steelink, C., G. Tollin, and T. Reid: J. Amer. chem. Soc. 87, 2056–2057 (1965); Tetrahedron Letters 1966, 105-111.

    Article  CAS  Google Scholar 

  211. Stockman, L.: Yield and Quality — a Balance Problem. Svensk Pappertid. 68, 572–577 (1965).

    Google Scholar 

  212. Stone, J. E., S. A. Brown, and K. G. Tanner: Lignin Biosynthesis using Isotopic Carbon. Can. J. Chem. 31, 207-213, 755–760 (1953).

    Article  Google Scholar 

  213. Sundman, V., T. Kuusi, S. Kuhanen, and G. Carlberg: Microbial Decomposition of Lignins. Acta Agriculturae Scand. 14, 229–248 (1964).

    Article  CAS  Google Scholar 

  214. Torres-Serres, J.: Unpublished results.

    Google Scholar 

  215. Towers, G. H. N.: Metabolism of Phenolic Compounds in Plants. In (70), pp. 249-294.

    Google Scholar 

  216. Towers, G. H. N. and W. S. G. Maass: Phenolic Acids and Lignin in the Lycopodiales. Phytochem. 4, 57–66 (1965).

    Article  CAS  Google Scholar 

  217. Treiber, E.: Die Chemie der pflanzlichen Zellwand. Springer-Verlag, Berlin-Heidelberg-Göttingen, 1957.

    Google Scholar 

  218. Tschammler, H., K. Kratzl, R. Leutner, A. Steininger, and J. Kisser: Infrared Spectra of Microscopic Wood Sections and Certain Model Compounds. Mikroskopie 8, 238–246 (1953).

    Google Scholar 

  219. Wacek, A., O. Härtel, and S. Meralla: Über den Einfluß von Coniferenzusatz auf die Verholzung von Karottengewebe bei Kultur in vitro. Holzforschung 7, 58–62 (1953).

    Article  CAS  Google Scholar 

  220. Wacek, A., O. Härtel: Über den Einfluß von Coniferenzusatz auf die Verholzung von Karottengewebe bei Kultur in vitro. Holzforschung 8, 65–68 (1954).

    Article  CAS  Google Scholar 

  221. Wacek, A., O. Härtel: Über den Einfluß von Coniferenzusatz auf die Verholzung von Karottengewebe bei Kultur in vitro. Holzforschung 12, 33–36, 97-99 (1958).

    Article  Google Scholar 

  222. Wardrop, A. B.: The Structure and Formation of the Cell Wall in Xylem. In (153), pp. 87-134.

    Google Scholar 

  223. Wardrop, A. B.: Cellular Differentiation in Xylem. In (30), pp. 61-97.

    Google Scholar 

  224. Wardrop, A. B. and D. E. Bland: The Process of Lignification in Woody Plants. In (94), pp. 92-116.

    Google Scholar 

  225. Wenzl, H. F. J.: Entwicklung und Stand der Sulfitzellstoff-Erzeugung, Holzforschung 17, 33–53, 71-86, 111-121 (1963).

    Article  CAS  Google Scholar 

  226. Wenzl, H. F. J.: Entwicklung und Stand der Sulfatzellstoff-Erzeugung. Holzforschung 13, 97–112 (1959).

    Article  Google Scholar 

  227. Wenzl, H. F. J.: Entwicklung und Stand der Sulfatzellstoff-Erzeugung. Holzforschung 14, 4–21 (1960).

    Article  CAS  Google Scholar 

  228. Wise, L. E., and E. C. Jahn: Wood Chemistry. Reinhold, New York, 1952.

    Google Scholar 

  229. Zimmerman, M. H. (Editor): The Formation of Wood in Forest Trees. Academic Press, New York-London, 1964.

    Google Scholar 

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  1. Dr. John M. Harkin

    Present address: Division of Wood Chemistry, Forest Products Laboratory, Madison, Wisconsin, 53705, USA

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  1. Forschungsinstitut für die Chemie des Holzes und der Polysaccharide, Organisch-Chemisches Institut, Universität Heidelberg, Deutschland

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Harkin, J.M. (1996). Recent Developments in Lignin Chemistry. In: Naturstoffe. Fortschritte der Chemischen Forschung, vol 6. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-25280-2_4

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