Abstract
Lignin offers a number of attractive features as a starting material for chemical production, and the only large scale source of aromatic moieties in nature. It is highly abundant, comprising 15–25 wt% of lignocellulosic feedstocks, such as agricultural materials or forest resources, making it the second most available source of renewable carbon after cellulose.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Araujo JDP, Grande CA, Rodrigues AE (2010) Vanillin production from lignin oxidation in a batch reactor. Chem Eng Res Des 88:1024–1032
Auhorn WJ, Niemela K (2007) Process chemicals for the production of chemical pulp. Prof Papermaking 2:10–20
Barreca AM, Fabbrini M, Galli C, Gentili P, Ljunggren S (2003) Laccase/mediated oxidation of a lignin model for improved delignification procedures. J Mol Catal B 26:105–110
Bjorsvik HR (1999) Fine chemicals from lignosulfonates. 1. Synthesis of vanillin by oxidation of lignosulfonates. Org Proc Res Devel 3:330–340
Boerjan W, Ralph J, Baucher M (2003) Lignin biosynthesis. Ann Rev Plant Biol 54:519–546
Bohlin C, Persson P, Gorton L, Lundquist K, Jonsson LF (2005) Product profiles in enzymic and non-enzymic oxidations of the lignin model compound erythro-1-(3,4-dimethoxyphenyl)2-(2-methoxyphenoxy)-1,3-propanediol. J Mol Catal B 35:100–107
Bosch E, Rathore R, Kochi JK (1994) Novel catalysis of hydroquinone autoxidation with nitrogen-oxides. J Org Chem 59:2529–2536
Bozell JJ, Hames BR, Dimmel DR (1995) Cobalt-Schiff base complex-catalyzed oxidation of para-substituted phenolics—preparation of benzoquinones. J Org Chem 60:2398–2404
Bozell JJ, Hoberg JO, Dimmel DR (1998) Catalytic oxidation of para-substituted phenols with nitrogen dioxide and oxygen. Tetrahedron Lett 39:2261–2264
Bozell JJ, Holladay JE, Johnson D, White JF (2007) Top value added chemicals from biomass. Volume II—results of screening for potential candidates from Biorefinery Lignin. Pacific Northwest National Laboratory, Richland, WA
Bozell JJ, Black SK, Myers M, Cahill D, Miller WP, Park S (2011a) Solvent fractionation of renewable woody feedstocks: Organosolv generation of biorefinery process streams for the production of biobased chemicals. Biomass Bioenergy 35:4197–4208
Bozell JJ, O’Lenick CJ, Warwick S (2011b) Biomass fractionation for the biorefinery: heteronuclear multiple quantum coherence-nuclear magnetic resonance investigation of lignin isolated from solvent fractionation of switchgrass. J Agric Food Chem 59:9232–9242
Busch DH (1988) Synthetic dioxygen carriers for dioxygen transport. In: Martell AE, Sawyer DT (eds) Oxygen complexes and oxygen activation by transition metals. Plenum, New York
Cedeno D, Bozell JJ (2012) Catalytic oxidation of para-substituted phenols with cobalt-Schiff base complexes/O2-selective conversion of syringyl and guaiacyl lignin models to benzoquinones. Tetrahedron Lett 53:2380–2383
Collinson SR, Thielemans W (2010) The catalytic oxidation of biomass to new materials focusing on starch, cellulose and lignin. Coord Chem Rev 254:1854–1870
Creighton RHJ, McCarthy JL, Hibbert H (1941) Aromatic aldehydes from spruce and maple woods. J Am Chem Soc 63:312
Crestini C, Jurasek L, Argyropoulos DS (2003) On the mechanism of the laccase-mediator system in the oxidation of lignin. Chem Eur J 9:5371–5378
Crestini C, Pastorini A, Tagliatesta P (2004) Metalloporphyrins immobilized on motmorillonite as biomimetic catalysts in the oxidation of lignin model compounds. J Mol Catal A 208:195–202
Crestini C, Pro P, Neri V, Saladino R (2005) Methyltrioxorhenium: a new catalyst for the activation of hydrogen peroxide to the oxidation of lignin and lignin model compounds. Biorg Med Chem 13:2569–2578
Crestini C, Caponi MC, Argyropoulos DS, Saladino R (2006) Immobilized methyltrioxo rhenium (MTO)/H2O2 systems for the oxidation of lignin and lignin model compounds. Biorg Med Chem 14:5292–5302
Cui F, Dolphin D (1995) Iron porphyrin catalyzed oxidation of lignin model compounds: Oxidation of phenylpropane and phenylpropene model compounds. Can J Chem 73:2153–2157
da Silva EAB, Zabkova M, Araujo JD, Cateto CA, Barreiro MF, Belgacem MN, Rodriques AE (2009) An integrated process to produce vanillin and lignin-based polyurethanes from kraft lignin. Chem Eng Res Des 87:1276–1292
Dence CW, Reeve DW (1996) Pulp bleaching—principles and practice. TAPPI, Atlanta
Dicosimo R, Szabo HC (1988) Oxidation of lignin model compounds using single-electron-transfer catalysts. J Org Chem 53:1673–1679
Dimmel DR, Bozell JJ (1991) Pulping catalysts from lignin. Tappi J 74:239–241
Dimmel DR, Karim MR, Savidakis MC, Bozell JJ (1996) Pulping catalysts from lignin. 5. Nitrogen dioxide oxidation of lignin models to benzoquinones. J Wood Chem Technol 16:169–189
Dimmel DR, Althen E, Savidakis M, Courchene C, Bozell JJ (1999) New quinone-based pulping catalysts. Tappi J 82:83–89
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. Enzyme Microb Technol 37:340–346
Evtuguin DV, Daniel AID, Silvestre AJD, Amado FML, Neto CP (2000) Lignin aerobic oxidation promoted by molybdovanadophosphate polyanion PMo7V5O40 (8−). Study on the oxidative cleavage of beta-O-4 aryl ether structures using model compounds. J Mol Catal A 154:217–224
Fengel D, Wegener G (1984) Wood. Chemistry, ultrastructure, reactions. Walter de Gruyter, Berlin
Goncalves AR, Schuchardt U (1999) Oxidation of organosolv lignins in acetic acid—Influence of oxygen pressure. Appl Biochem Biotechnol 77–9:127–132
Hanson SK, Wu R, Silks LAP (2012) C–C or C–O bond cleavage in a phenolic lignin model compound: selectivity depends on vanadium catalyst. Angew Chem Int Ed 51:3410–3413
Hocking MB (1997) Vanillin: synthetic flavoring from spent sulfite liquor. J Chem Educ 74:1055–1059
Lahtinen M, Kruus K, Boer H, Kemell M, Andberg M, Viikari L, Sipila J (2009) The effect of lignin model compound structure on the rate of oxidation catalyzed by two different fungal laccases. J Mol Catal B 57:204–210
Li KC, Xu F, Eriksson KEL (1999) Comparison of fungal laccases and redox mediators in oxidation of a nonphenolic lignin model compound. Appl Environ Microbiol 65:2654–2660
Li JB, Gellerstedt G, Toven K (2009) Steam explosion lignins; their extraction, structure and potential as feedstock for biodiesel and chemicals. Bioresour Technol 100:2556–2561
Mathias AL, Rodrigues AE (1995) Production of vanillin by oxidation of pine kraft lignins with oxygen. Holzforschung 49:273–278
Mathias AL, Lopretti MI, Rodrigues AE (1995) Chemical and biological oxidation of pinus-pinaster lignin for the production of vanillin. J Chem Technol Biotechnol 64:225–234
Nichols JM, Bishop LM, Bergman RG, Ellman JA (2010) Catalytic C–O bond cleavage of 2-aryloxy-1-arylethanols and its application to the depolymerization of lignin-related polymers. J Am Chem Soc 132:12554–12555
Nishinaga A, Tomita H, Nishizawa K, Matsuura T, Ooi S, Hirotsu K (1981) Regioselective formation of peroxyquinolatocobalt(III) complexes in the oxygenation of 2,6-di-tert-butylphenols with cobalt(II) Schiff-base complexes. J Chem Soc Dalton, pp 1504–1514
Partenheimer W (2009) The aerobic oxidative cleavage of lignin to produce hydroxyaromatic benzaldehydes and carboxylic acids via metal/bromide catalysts in acetic acid/water mixtures. Adv Synth Catal 351:456–466
Pearl IA (1942) Vanillin from lignin materials. J Am Chem Soc 64:1429–1431
Perng YS, Oloman CW, Watson PA, James BR (1994) Catalytic oxygen bleaching of wood pulp with metal porphyrin and phthalocyanine complexes. Tappi J 77:119–125
Rappoport Z (2003) The chemistry of phenols. Wiley, Hoboken
Rathore R, Bosch E, Kochi JK (1994) Selective nitration versus oxidative dealkylation of hydroquinone ethers with nitrogen-dioxide. Tetrahedron 50:6727–6758
Reichert E, Wintringer R, Volmer DA, Hempelmann R (2012) Electro-catalytic oxidative cleavage of lignin in a protic ionic liquid. Phys Chem Chem Phys 14:5214–5221
Rochefort D, Bourbonnais R, Leech D, Paice MG (2002) Oxidation of lignin model compounds by organic and transition metal-based electron transfer mediators. Chem Commun pp 1182–1183
Rochefort D, Leech D, Bourbonnais R (2004) Electron transfer mediator systems for bleaching of paper pulp. Green Chem 6:14–24
Samuel R, Pu YQ, Raman B, Ragauskas AJ (2010) Structural characterization and comparison of switchgrass ball-milled lignin before and after dilute acid pretreatment. Appl Biochem Biotechnol 162:62–74
Sergeev AG, Hartwig JF (2011) Selective, nickel-catalyzed hydrogenolysis of aryl ethers. Science 332:439–443
Sippola VO, Krause AOI (2005) Bis(o-phenanthroline)copper-catalysed oxidation of lignin model compounds for oxygen bleaching of pulp. Catal Today 100:237–242
Son S, Toste FD (2010) Non-oxidative vanadium-catalyzed C–O bond cleavage: application to degradation of lignin model compounds. Angew Chem Int Ed 49:3791–3794
Tolba R, Tian M, Wen JL, Jiang ZH, Chen AC (2010) Electrochemical oxidation of lignin at IrO2-based oxide electrodes. J Electroanal Chem 649:9–15
Vanholme R, Demedts B, Morreel K, Ralph J, Boerjan W (2010) Lignin biosynthesis and structure. Plant Physiol 153:895–905
Villar JC, Caperos A, Garcia-Ochoa F (2001) Oxidation of hardwood kraft-lignin to phenolic derivatives with oxygen as oxidant. Wood Sci Technol 35:245–255
Voitl T, von Rohr PR (2008) Oxidation of lignin using aqueous polyoxometalates in the presence of alcohols. ChemSusChem 1:763–769
Voitl T, von Rohr PR (2010) Demonstration of a process for the conversion of kraft lignin into vanillin and methyl vanillate by acidic oxidation in aqueous methanol. Ind Eng Chem Res 49:520–525
Weinstock IA, Atalla RH, Reiner RS, Moen MA, Hammel KE, Houtman CJ, Hill CL (1996) A new environmentally benign technology and approach to bleaching kraft pulp. Polyoxometalates for selective delignification and waste mineralization. New J Chem 20:269–275
Weinstock IA, Atalla RH, Reiner RS, Moen MA, Hammel KE, Houtman CJ, Hill CL, Harrup MK (1997) A new environmentally benign technology for transforming wood pulp into paper—Engineering polyoxometalates as catalysts for multiple processes. J Mol Catal A 116:59–84
Zakzeski J, Jongerius AL, Weckhuysen BM (2010) Transition metal catalyzed oxidation of Alcell lignin, soda lignin, and lignin model compounds in ionic liquids. Green Chem 12:1225–1236
Zhu WM, Ford WT (1993) Oxidation of lignin model compounds in water with dioxygen and hydrogen-peroxide catalyzed by metallophthalocyanines. J Mol Catal 78:367–378
Acknowledgments
This work was supported as part of the Center for Direct Catalytic Conversion of Biomass to Biofuels (C3Bio), an Energy Frontier Research Center funded by the US Department of Energy, Office of Science, Office of Basic Energy Sciences under Award Number DE-SC0000997, and U. S. Department of Energy Office of Industrial Technologies.
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2014 Springer Science+Business Media New York
About this chapter
Cite this chapter
Bozell, J.J. (2014). Catalytic Oxidation of Lignin for the Production of Low Molecular Weight Aromatics. In: McCann, M., Buckeridge, M., Carpita, N. (eds) Plants and BioEnergy. Advances in Plant Biology, vol 4. Springer, New York, NY. https://doi.org/10.1007/978-1-4614-9329-7_17
Download citation
DOI: https://doi.org/10.1007/978-1-4614-9329-7_17
Published:
Publisher Name: Springer, New York, NY
Print ISBN: 978-1-4614-9328-0
Online ISBN: 978-1-4614-9329-7
eBook Packages: Biomedical and Life SciencesBiomedical and Life Sciences (R0)