Conversion of lignin: Chemical technologies and biotechnologies - oxidative strategies in lignin upgrade

Biorefinery: From Biomass to Chemicals and Fuels

Volumn , Issue , 2012, Pages 167-206

  Decina, Silvia ^a   Crestini, Claudia ^a  

^a Tor Vergaata University   (Italy)

Author keywords

[No Author keywords available]

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EID: 84919378767     PISSN: None     EISSN: None     Source Type: Book    
DOI: None     Document Type: Chapter

References (98)

1. Abadulla, E., Tzanov, T., Costa, S., Robra, K.H., Cavaco-Paulo, A., Guebitz, G.M. (2000). Decolorization and detoxification of textile dyes with a laccase from trametes hirsute, pl. Environ. Microb. 66: 3357-3362.
2. Aden, A. (2005). Lignocellulosic biomass to ethanol process design and economics utilizing co-current dilute acid prehydrolysis and enzymatic hydrolysis for corn stover. Bioresource Technology 96(6): 673-686.
3. Avellar, B.K., Glasser, W.G. (1998). Steam-assisted biomass fractionation. I. Process considerations and economic evaluation. Biomass Bioenerg. 14: 205.
4. Aziz, S., Tappi, J., Sarkanen, K. (1989). Organosolv pulping: A review. Tappi Journal 72(3): 169.
5. Beatson, R.P.C., Gancet, C., Heitner, J., Tappi, J. (1984). The topochemistry of black spruce sulfonation. Tappi 67: 82-85.
6. Bianchini, G., Crucianelli, M., Crestini, C., Saladino, R. (2006). Methyltrioxorhenium catalysis in nonconventional solvents: A great catalyst in a safe reaction medium. Top. Catal. 40: 221-227.
7. Boerjan, W.J., Ralph, J., Baucher, M. (2003). Cell-wall carbohydrates and their modification as a resource for biofuels. Annu. Rev. Plant Biol. 54: 519-546.
8. Bolzacchini, E., Canevali, C., Morazzoni, F., Orlandi, M., Rindone, B., Scotti, R. (1997). Spectromagnetic investigation of the active species in the oxidation of propenoidic phenols catalysed by N, N'-ethylenebis(salicylideneiminato) cobalt(II) [cosalen]. J. Chem. Soc., Dalton Trans. 4695-4699.
9. Bolzacchini, E., Chiavetto, L.B., Canevali, C., Morazzoni, F., Orlandi, M., Rindone, B. (1996). Oxidation of propenoidic phenols catalysed by N, N',-ethylenebis (salicylideneiminato) cobalt (II) [cosalen]: Reactivity and spetroscopic studies. J. Mol. Catal. 112: 347-351.
10. Bourbonnais, R., Paice, M.G. (1990). Oxidation of non-phenolic substrates: An expanded role for laccase in lignin biodegradation. FEBS Lett. 267: 99-102.
11. Bourbonnais, R., Paice, M.G. (1992). Demethylation and delignification of kraft pulp by Trametes versicolor laccase in the presence of 2,2'-azinobis-(3-ethylbenzthiazoline-6-sulphonate). Appl. Microbiol. Biotechnol. 36: 823-827.
12. Bourbonnais, R., Paice, M.G., Reid, I.D., Lanthier, P., Yaguchi, M. (1995). Lignin oxidation by laccase isozymes from Trametes versicolor and role of the mediator 2,2'-azinobis(3-ethylbenzthiazoline-6-sulfonate) in kraft lignin depolymerisation. Appl. Environ. Microbiol. 61: 1876-1880.
13. Bozell, J.J., Hames, B.R., Dimmel, D.R. (1995). ChemInform abstract: Cobalt-Schiffbase complex catalyzed oxidation of para-substituted phenolics. Preparation of benzoquinones. J. Org. Chem. 60:,2398.
14. Bozell, J.J., Hoberg, J.O., Dimmel, D.R. (1998). Tetrahedron letters, ChemInform abstract: Catalytic oxidation of para-substituted phenols with nitrogen dioxide and oxygen. 39: 2261.
15. Bozell, J.J., Hoberg, J.O., Dimmel, D.R. (2000). Heteropolyacid catalyzed oxidation of lignin and lignin models to benzoquinones. J. Wood Chem. Tech. 20: 19.
16. Brogdon, B.N., Dimmel, D.R.J. (1996). Fundamental study of relative delignification. Wood Chem. Technol. 16: 297.
17. Buchholz, R.F., Neal, J.A., McCarthy, J.L. (1992). Some properties of paucidisperse gymnosperm lignin sulfonates of different molecular weights. J. Wood Chem. Tech. 12: 447.
18. Caldwell, E.S., Steelink, C. (1969). Phenoxy radical intermediates in the enzymatic degradation of lignin model compounds. Biochim. Biophys. Acta 189: 420-431.
19. Call, H.P., Mucke, I. (1997). History, overview and applications of mediated lignolytic systems, especially laccase-mediator-systems (Lignozym process). J. Biotechnol. 53: 163-202.
20. Canevali, C., Orlandi, M., Zoia, L., Scotti, R., Toppa, E.L., Sibila, J., et al. (2005). Radicalization of lignocellulosic fibers, related structural and morphological changes. Biomacromolecules 6: 1592-1601.
21. Capanema, E., Balakshin, A.M.Y., Kadla, J.F. (2004). On isolation of milled wood lignin from eucalyptus wood. J. Agric. Food Chem. 52: 1850-1860.
22. Carnevali, C., Orlandi, M., Pardi, L., Rindone, B., Scotti, R., Sibila, J., et al. (2002). Oxidative degradation of monomeric and dimeric phenylpropanoids: reactivity and mechanism investigation. J. Chem. Soc., Dalton Trans. 15: 3007-3014.
23. Cho, K., Bailey, J.E. (1979). Immobilization of enzymes on activated carbon: Selection and preparation of the carbon support., Biotechnol. Bioeng. 21: 461-476.
24. Cole, J.L., Clark, P.A., Solomon, E.J. (1990). Spectroscopic and chemical studies of the laccase trinuclear copper active site: Geometric and electronic structure. J. Am. Chem. Soc. 112: 9534-9548.
25. Crestini, C., Argyropoulos, D.S. (1998). The early oxidative biodegradation steps of residual kraft lignin models with laccase. Bioorg. Med. Chem. 6: 2161-2169.
26. Crestini, C., Caponi, M.C., Argyropoulos, D.S., Saladino, R. (2006). Immobilized methyltrioxo rhenium (MTO)/H2O2 systems for the oxidation of lignin and lignin model compounds. Bioorg. Med. Chem. 14: 5292-5302.
27. Crestini, C., Crucianelli, M., Orlandi, M., Saladino, R. (2010). Oxidative strategies in lignin chemistry: A new environmental friendly approach for the functionalisation of lignin and lignocellulosic fibers. Catalysis Today 156(1,2): 8-22.
28. Crestini, C., D'Annibale, A., Giovannozzi Sermanni, G., Saladino, R. (2000). The reactivity of phenolic and non-phenolic residual kraft lignin model compounds with Mn(II)-peroxidase from Lentinula edodes., Bioorg. Med. Chem. 8: 433-438.
29. Crestini, C., Jurasek, L., Argyropoulos, D.S. (2003). On the mechanism of the laccasemediator system in the oxidation of lignin. Chem. Eur. J. 9: 5371-5378.
30. Crestini, C., Pastorini, A., Tagliatesta, P. (2004)., Immobilized metalloporphyrins as biomimetic catalysts in the oxidation of lignin model compounds. J. Mol. Catal. A: Chem. 208: 195-202.
31. Crestini, C., Perazzini, R., Saladino, R. (2010). Oxidative functionalisation of lignin by layer-by-layer immobilised laccases and laccase microcapsules. Appl. Catal. A: Gen. 372: 115-123.
32. Crestini, C.R., Saladino, P., Tagliatesta, T., Boschi, T. (1999). Biomimetic degradation of lignin and lignin model compounds by synthetic anionic and cationic water soluble manganese and iron porphyrins., Bioorg. Med. Chem. 7: 1897-1905.
33. D'Annibale, A., Crestini, C., Di Mattia, E., Giovannozzi Sermanni, G. (1996). Veratryl alcohol oxidation by manganese-dependent peroxidase from Lentinus erode. J. Biotechnol. 48: 231-239.
34. DeBons, F.E., Whittington, L. E. (1992). Improved oil recovery surfactants based on lignin. J. Petroleum Sci. Eng. 7: 131-138.
35. Decher, G., Hong, J.D., Schmitt, J. (1992). Buildup of ultrathin multilayer films by a self-assembly process. III. Consecutively alternating adsorption of anionic and cationic poly-electrolytes on charged surfaces. Thin Solid Film 210/211: 831-835.
36. Dimmel, D.R., Bozell, J.J., von Oepen, D.G., Savidakis, M.C. (2002). Advances in chemical modification, properties and usage of lignin. New York: Kluwer Academic.
37. Di Serio, M., Maturo, C., De Alteriis, E., Parascandola, P., Tesser, R., Santacesaria, E. (2003). Lactose hydrolysis by immobilized b-galactosidase: The effect of the supports and the kinetics. Catal. Today 79/80: 333-339.
38. Elegir, G., Daina, S., Zoia, L., Bestetti, G., Orlandi, M. (2005). Laccase mediator system: Oxidation of recalcitrant lignin model structures present in residual kraft lignin. EnzymeMicrob. Technol. 37: 340-346.
39. Ferm, R., Kringstad, K.P., Cowling, E.B. (1972). Formation of free radicals in milled wood lignin and syringaldehyde by phenol-oxidizing enzymes. Sven. Pappestidn. 75: 85.
40. Fredheim, G., Braaten, S.M., Christensen, B.E. (2002). Comparison of molecular weight and molecular weight distributions of softwood and hardwood lignosulfonates. J. Chromatog. 942: 191.
41. Freheim, G.E., Braaten, S.M., Christensen, B.E. (2003). Top value-added chemicals from biomass. J. Wood Chem. Tech. 23: 197.
42. Genin, H.S., Lawler, K.A., Hoffmann, R., Herrmann, W.A., Fischer, R.W., Scherer, W. (1995). Polymeric methyltrioxorhenium: Some models for its electronic structure. J. Am. Chem. Soc. 117: 3244-3252.
43. Gierer, J. (1985). Chemistry of delignification. J. Wood Sci. Technol. 19: 289-312.
44. Glasser, W.G., Northey, R.A., Schultz, T.P. (1999). Lignin: Historical, biological and materials perspectives. ACS Symposium Series 742. Washington, DC: American Chemical Society.
45. Glasser, W.G., Sarkanen S. (1988). Lignin properties and materials. ACS Symposium Series 397. Washington, DC: American Chemical Society.
46. Glenn, J.K., Morgan, M.A., Mayfield, M.B., Kuwahara, M., Gold, M.M. (1983). An extracellular H2O2-requiring enzyme preparation involved in lignin biodegradation by the white rot basidiomycete Phanerochaete chrysosporium. Biochem. Biophys. Res. Commun. 114: 1077-1083.
47. Guerra, A., Filpponen, I., Lucia, L.A., Argyropoulos, D.S. (2006). Comparative evaluation of three lignin isolation protocols for various wood species. J. Agric. Food Chem. 54: 9696-9705.
48. Haikarailen, A., Sipila, J., Pietikainen, P., Pajunen, A., Mutikainen, I. (2001). J. Chem. Soc., Dalton Trans. 991-995.
49. Heikkinen, S., Toikka, M.M., Karhunen, P. T., Kilpelainen, I. (2003). Quantitative 2D HSQC (Q-HSQC) via suppression of J-dependence of polarization transfer in NMR spectroscopy: Application to wood lignin. J. Am. Chem. Soc. 125: 4362-4367.
50. Held, C., Kandelbauer, A., Schroeder, M., Cavaco-Paulo, A., Gubitz, Environ., G.M. (2005). environmentally friendly bleaching of cotton using laccases. Chem. Lett. 3: 74-77.
51. Hermann, W.A., Fischer, R.W., Scherer, W., Rauch, M.U. (1993). Methyltrioxorhenium-Catalyze C - H insertion reactions of hydrogen peroxide. Angew. Chem. Int. Ed. Engl. 32: 1157-1160.
52. Herrmann, W.A., Fischer, R.W. (1995). Multiple bonds between main-group elements and transition metals. 136. "Polymerization" of an organometal oxide: The unusual behavior of methyltrioxorhenium(VII) in water. J. Am. Chem. Soc. 117: 3223-3230.
53. Heytz, M., Capek-Ménard, E., Koeberle, P.G., Gagné, J., Chornet, E. (1991). Fractionation of populus tremuloides at the pilot plant scale: Optimization of steam pretreatment conditions using the STAKE II technology. Bioresource technol. 35: 23.
54. Higuchi, T. (1990). Lignin biochemistry: Biosynthesis and biodegradation. Wood Sci. Technol. 24: 23-63.
55. Holtman, H., Chang, M., Jameel, H., Kadla, J. F. (2003). Quantitative 13C NMR characterization of milled wood lignins isolated by different milling techniques. J. Agric. Food Chem. 51: 3535-3540.
56. Johnson, D. K. (2002). Lignin, a source of bioethanol co-products. Environmental Science and Technology 36(8): 1665-1670.
57. Kandelbauer, A., Maute, O., Erlacher, A., Carvaco Pauolo, A., Gubitz, G. (2004). Study of dye decolorization in an immobilized laccase enzyme-reactor using online spectroscopy. Biotechnol. Bioeng. 87: 552-563.
58. Kangaz, H., Salmi, J., Kleen, M. (2002). Surface chemistry and morphology of thermome-chanical pulp. In Proceedings of 7th European Workshop of Lignocellulosic and Pulp Turku, p. 115.
59. Kawai, S., Umezawa, T., Higuchi, T. (1988). Degradation mechanisms of phenolic [beta]-1 lignin substructure model compounds by laccase of Coriolus versicolor. Arch. Biochem. Biophys. 262: 99-110.
60. Kim, H., Ralph, J., Akiyama, T. (2008). Solution-state 2D NMR of ball-milled plant cell wall gels in DMSO-d6. Bioen. Res. 1: 56-66.
61. Kirk, T.K., Chang, H.-M. (1990). Biotechnology in pulp and paper manufacture. Stoneham: Butterworths.
62. Koljonen, K., Osterberg, M., Johansson, L.S., Stenius, P. (2003). Colloids and surfaces: A physicochemical and engineering aspects. Physicochem. Eng. Aspects 228: 143-158.
63. Krajewska, B. (2004). Application of chitin-and chitosan-based materials for enzyme immobilizations: A review. Enzyme Microb. Technol. 35: 126-139.
64. Lapierre, C., Pollet, B., Monties, B. (1995). Proceedings of the 8th International Symposium on Wood and Pulping Chemistry, Helsinki, Finland, p. 131.
65. Lebo, S. E. Jr., Gargulak, J.D., McNally, T. J. (2001). Lignin. In Kirk-Othmer encyclopedia of chemical technology, 4th ed. New York: John Wiley & Sons.
66. Lin, S. Y., Lin, I.S. (1990). Ullmann's encyclopedia of industrial chemistry, 5th ed., Vol. 15. Weinheim, Germany: VCH.
67. Lundquist, K., Kristersson, P. (1985). Exhaustive laccase-catalysed oxidation of a lignin model compound (vanillyl glycol) produces methanol and polymeric quinoid products. Biochem. J. 229: 277-279.
68. McDonough, T.J., Tappi J. (1993). The chemistry of organosolv delignification. Tappi Journal 76(8): 186.
69. Morozova, O.V., Shumakovich, G.P., Shleev, S.V., Yaropolov, Ya. I. (2007). Laccase-mediator systems and their applications: A review. Appl. Biochem. Microbiol. 43(4): 523.
70. Nayak, P.L. (1999). Biodegradable polymers: Opportunities and challenges. Macrom. Chem. Phys. C 39: 481-505.
71. Paice, M.G., Bourbonnaise, R., Reid, I.D., Archibald, F.S., Jurasek, L. (1995). Oxidative bleaching enzymes: A review. J. Pulp Paper Sci. 2: 280-284.
72. Peng, F., Simonsen, R., Westermark, U. (1992). Cell wall sulfur distribution in chemithermo-mechanical pulping of spruce. Nord. Pulp Paper Res. J. 7: 140-143.
73. Peyratout, C.L., Dähne, A. (2004). Tailor-made polyelectrolyte microcapsules: From multilayers to smart containers. Chem. Int. Ed. 43: 3762-3783.
74. Potthast, A., Koch, H., Fisher, K. (1997). Oxidation of 1-hydroxybenzotriazole by laccase and lignin peroxidase. Proc. Int. Symp. Wood Pulping Chem.
75. Ralph, J. K., Lundquist, G., Brunow, F., Lu, H., Kim, P. F., Schatz, J. M., Marita, R. D., Hatfield, S. A., Christensen, J.H., Boerjan, W. (2004). Lignin biosynthesis and structure. Phytochem. Rev. 3: 29-60.
76. Reid, I.D., Paice, M.G. (1994). Effects of a fungal treatment on the brightiness and strength properties of a mechanical pulp from Douglas-fir. FEMS Microb. Rev. 13: 369-376.
77. Reinhammer, B., Malstrom, B. (1981). Copper proteins. New York: Wiley-Interscience.
78. Rodriguez Couto, S., Osmaa, J.F., Saraviab, V., Gubitz, G.M., Toca Herrera, J.L. (2007). Appl. Catal. 329: 156-160.
79. Ryan, S., Schnitzhofer, W., Tzanov, T., Cavaco-Paulo, A., Guebitz, G.M. (2003). An acid-stable laccase from sclerotium rolfsii with potential for wool dye decolorization. Enzyme Microb. Technol. 33: 766-774.
80. Sakakibara, A. (1980). New opportunities for lignin conversion in the biorefinery. Wood Sci. Technol. 14: 89.
81. Schiene, R. (2002). Chemical modification and usage of lignin. New York: Kluwer Academic-Press.
82. Schroeter, M.C., Tappi, J. (1991). Possible lignin reactions in the Organocell pulping process. Tappi Journal 74(10): 197.
83. Shevchenko, S. M., Beatson, R. P., Saddler, J. N. (1999). The nature of lignin from steam explosion/enzymatic hydrolysis of softwood: Structural features and possible uses: Scientific note. Appl. Biochem. Biotech. 77-79: 867.
84. Shimada, M., Habe, T., Higuchi, T., Okamoto, T., Panijpan, B. (1977). Incorporation of dioxygen into hydroxylated product during the C-C single bond cleavage. Holzforshung 41: 277.
85. Shleev, S., Christenson, A., Serezhenkov, V., Burbaev, D., Yaropolov, A., Gorton, L., Ruzgas, T. (2005). Electrochemical redox transformations of T1 and T2 copper sites in native Trametes hirsuta laccase at gold electrode. Biochem. J. 385: 745-754.
86. Sjostrom, E., et al. (1962). Changes in cooking liquor composition during sulphite pulping. Svensk Papperstidn. 65: 855.
87. Smith, B. R., Rice, R. W., Ince, P. J. (2000). Pulp capacity in the United States. USDA Forest Service, General Technical Report FPL-GTR-139.
88. Solomon, E.I., Lowery, M.D. (1993). Electronic structure contributions to function in bioinorganic chemistry. Science 259: 1575-1581.
89. Sun, Y., Cheng, J. (2002). Hydrolysis of lignocellulosic materials for ethanol production: A review. J. Biores. Tech. 83: 1.
90. Torget, R. W., Kim, J. S., Lee, Y. (2000). Kinetics of glucose decomposition during dilute-acid hydrolysis of lignocellulosic biomass. Ind. Eng. Chem. Res. 39: 2817.
91. Tuor, H., Wariishi, H., Shoemaker, M.H., Gold. (1992). Oxidation of phenolic arylglycerol β -aryl ether lignin model compounds by manganese peroxidase from Phanerochaete chrysosporium: Oxidative cleavage of an α -carbonyl model compound. Biochem. 31: 4986-4995.
92. Varshney, A.K., Patel, D.J. (1988). Hydrogenation of benzene to cyclohexene over polymer-supported ruthenium catalysts. Sci. Ind. Res. 47(6): 315.
93. Wariishi, H., Akileswaran, L., Gold, M.H. (1988). Manganese peroxidase from the basidiomycete Phanerochaete chrysosporium: Spectral characterization of the oxidized states and the catalytic cycle. Biochem. 27: 5365-5370.
94. Wariishi, H., Valli, K., Gold, M.H. (1989). Oxidative cleavage of a phenolic diarylpropane lignin model dimer by manganese peroxidase from Phanerochaete chrysosporium. Biochem. 28: 6017-6023.
95. Werpy, T.G., Peterson, G. (2004). Top value added chemicals from biomass: Results of screening for potential candidate from sugars and synthesis gas. Volume I. Department of Energy.
96. Yean, W. Q., Goring, D. (1955). Evidence for the formation of lignin-hexenuronic acid-xylan complexes during modified kraft pulping processes. Svensk Papperstidn. 55: 563.
97. Zhang, F.G., Gellerstedt, J., Ralph, F., Lu, J., Ralph, J.K. (2006). NMR studies on the occurrence of spirodienone structures in lignins. J. Wood Chem. Technol. 26: 65-79.
98. Zoia, L., Canevali, C., Orlandi, M., Tolppa, E.-L., Sipila, J., Morazzoni, F. (2008). Radical formation on TMP fibers and related lignin chemical changes. Bioresources 3(1): 21-33.