Abstract
Lignin is a complex heterogeneous aromatic polymer consisting of up to 30 % of plant material. Its aromatic structure suggests that it is a possible renewable source for aromatic chemicals. However, the natural complexity and high stability of lignin makes its depolymerization a highly challenging task. Many efforts have been directed toward a better understanding of the structure and composition of lignin in order to design more efficient and greener deconstruction paths. This chapter aims at providing an overview of key advances in the field of lignin depolymerization, with special emphasis on chemical catalysis, ionic liquids, and biocatalysis. The various technologies are discussed and critically evaluated in terms of potential for further industrial implementation. Research gaps that still need to be addressed and the most promising approaches are highlighted.
This is a preview of subscription content, log in via an institution.
Buying options
Tax calculation will be finalised at checkout
Purchases are for personal use only
Learn about institutional subscriptionsReferences
Holladay J, White JF, Bozell JJ, Johnson D (2007) Top value-added chemicals from biomass. Vol. II: results of screening for potential candidates from biorefinery lignin; Report PNNL-16983. U.S. Department of Commerce: Springfield, VA, pp 1–79
Lora J (2008) Industrial commercial lignins: Sources, properties and application. In: Belgacem MN, Gandini A (eds) Monomers, polymers and composites from renewable resources. Elsevier, Amsterdam, pp 225–241
Gandini A, Belgacem MN (2008) Lignins as components of macromolecular materials. In: Belgacem MN, Gandini A (eds) Monomers, polymers and composites from renewable resources. Elsevier, Amsterdam, pp 243–271
Doherty WOS, Mousavioun P, Fellows CW (2011) Value-adding to cellulosic ethanol: lignin polymers. Ind Crop Prod 33:259–276
Hocking MB (1997) Vanillin: synthetic flavoring from spent sulfite liquor. J Chem Educ 74:1055–1059
Borregaard http://www.borregaard.com/Business-Areas/Other-Businesses/Borregaard-Ingredients/ (14 Dec 2015)
Xu C, Arancon RAD, Labidi J, Luque R (2014) Lignin depolymerisation strategies: towards valuable chemicals and fuels. Chem Soc Rev 43:7485–7500
Ragauskas AJ, Beckham GT, Biddy MJ, Chandra R, Chen F, Davis MF, Davison BH, Dixon RA, Gilna P, Keller M, Langan P, Naskar AK, Saddler JN, Tschaplinski TJ, Tuskan GA, Wyman CE (2014) Lignin valorization: improving lignin processing in the biorefinery. Science 344:1246843
Chatel G, Rogers RD (2014) Review: oxidation of lignin using ionic liquids-an innovative strategy to produce renewable chemicals. ACS Sustain Chem Eng 2:322–339
Li C, Zhao X, Wang A, Huber GW, Zhang T (2015) Catalytic transformation of lignin for the production of chemicals and fuels. Chem Rev 115:11559–11624
Zakzeski J, Bruijnincx PCA, Jongerius AL, Weckhuysen BM (2010) The catalytic valorization of lignin for the production of renewable chemicals. Chem Rev 110:3552–3599
Rodrigues Pinto PC, da Silva EAB, Rodrigues AE (2011) Insights into oxidative conversion of lignin to high-added-value phenolic aldehydes. Ind Eng Chem Res 50:741–748
Chakar FS, Ragauskas AJ (2004) Review of current and future softwood kraft lignin process chemistry. Ind Crop Prod 20:131–141
Capanema EA, Balakshin MY, Kadla JF (2005) Quantitative characterization of a hardwood milled wood lignin by nuclear magnetic resonance spectroscopy. J Agric Food Chem 53:9639–9649
Buranov AU, Mazza G (2008) Lignin in straw of herbaceous crops. Ind Crop Prod 28:237–259
Zhang AP, Lu FC, Sun RC, Ralph J (2009) Ferulate-coniferyl alcohol cross-coupled products formed by radical coupling reactions. Planta 229:1099–1108
Monteil-Rivera F, Phuong M, Ye M, Halasz A, Hawari J (2013) Isolation and characterization of herbaceous lignins for applications in biomaterials. Ind Crop Prod 41:356–364
Crestini C, Argyropoulos DS (1997) Structural analysis of wheat straw lignin by quantitative P-31 and 2D NMR spectroscopy. The occurrence of ester bonds and alpha-O-4 substructures. J Agric Food Chem 45:1212–1219
Scalbert A, Monties B, Lallemand J-Y, Guittet E, Rolando C (1985) Ether linkage between phenolic acids and lignin fractions from wheat straw. Phytochemistry 24:1359–1362
Ralph J, Marita J, Ralph S, Hatfield RD, Lu F, Ede RM, Peng J, Quideau S, Helm R, Grabber J, Kim H, Jimenez-Monteon G, Zhang Y, Jung H-JG, Landucci L, MacKay J, Sederoff R, Chapple C, Boudet A (1999) Solution-state NMR of lignins. In: Argyropoulos DS (ed) Advances in lignocellulosics characterization. Tappi Press, Atlanta, pp 55–108
Pu Y, Cao S, Ragauskas AJ (2011) Application of quantitative 31P NMR in biomass lignin and biofuel precursors characterization. Energy Environ Sci 4:3154–3166
Argyropoulos DS (1994) Quantitative phosphorus-31 NMR analysis of lignins, a new tool for the lignin chemist. J Wood Chem Technol 14:45–63
Cateto CA, Barreiro MF, Rodrigues AE, Brochier-Salon MC, Thielemans W, Belgacem MN (2008) Lignins as macromonomers for polyurethane synthesis: a comparative study on hydroxyl group determination. J Appl Polym Sci 109:3008–3017
Monteil-Rivera F, Paquet L (2015) Solvent-free catalyst-free microwave-assisted acylation of lignin. Ind Crop Prod 65:446–453
Yang Q, Wu SB, Lou R, Lv GJ (2011) Structural characterization of lignin from wheat straw. Wood Sci Technol 45:419–431
Hu G, Cateto C, Pu Y, Samuel R, Ragauskas AJ (2012) Structural characterization of switchgrass lignin after ethanol organosolv pretreatment. Energy Fuels 26:740–745
Hattalli S, Benaboura A, Ham-Pichavant F, Nourmamode A, Castellan A (2002) Adding value to Alfa grass (Stipa tenacissima L.) soda lignin as phenolic resins. 1. Lignin characterization. Polym Degrad Stab 75:259–264
Ahvazi B, Wojciechowicz O, Ton-That T-M, Hawari J (2011) Preparation of lignopolyols from wheat straw soda lignin. J Agric Food Chem 59:10505–10516
Moghaddam L, Zhang Z, Wellard RM, Bartley JP, Hara IMO, Doherty WOS (2014) Characterisation of lignins isolated from sugarcane bagasse pretreated with acidified ethylene glycol and ionic liquids. Biomass Bioenergy 70:498–512
Fengel D, Wegener G (1984) Chemical composition and analysis of wood. In: Fengel D, Wegener G (eds) Wood chemistry ultrastructure reactions. Walter de Gruyter, Berlin, pp 26–65
Jae J, Tompsett GA, Lin YC, Carlson TR, Shen J, Zhang T, Yang B, Wyman CE, Conner WC, Huber GW (2010) Depolymerization of lignocellulosic biomass to fuel precursors: maximizing carbon efficiency by combining hydrolysis with pyrolysis. Energy Environ Sci 3:358–365
Pandey MP, Kim CS (2011) Lignin depolymerization and conversion: a review of thermochemical methods. Chem Eng Technol 34:29–41
Wang K, Kim KH, Brown RC (2014) Catalytic pyrolysis of individual components of lignocellulosic biomass. Green Chem 16:727–735
Tarabanko VE, Petukhov DV, Selyutin GE (2004) New mechanism for the catalytic oxidation of lignin to vanillin. Kinet Catal 45:569–577
Wong Z, Chen K, Li J (2010) Formation of vanillin and syringaldehyde in an oxygen delignification process. Bioresoure 5:1509–1516
Araújo JDP, Grande CA, Rodrigues AE (2010) Vanillin production from lignin oxidation in a batch reactor. Chem Eng Res Des 88:1024–1032
Roberts VM, Stein V, Reiner T, Lemonidou A, Li X, Lercher JA (2011) Towards quantitative catalytic lignin depolymerization. Chem Eur J 17:5939–5948
Beauchet R, Monteil-Rivera F, Lavoie JM (2012) Conversion of lignin to aromatic-based chemicals (L-chems) and biofuels (L-fuels). Bioresour Technol 121:328–334
Gasson JR, Forchheim D, Sutter T, Hornung U, Kruse A, Barth T (2012) Modeling the lignin degradation kinetics in an ethanol/formic acid solvolysis approach. Part 1. Kinetic model development. Ind Eng Chem Res 51:10595–10606
Forchheim D, Gasson JR, Hornung U, Kruse A, Barth T (2012) Modeling the lignin degradation kinetics in an ethanol/formic acid solvolysis approach. Part 2. Validation and transfer to variable conditions. Ind Eng Chem Res 51:15053–15063
Toledano A, Serrano L, Labidi J (2012) Organosolv lignin depolymerisation with different base catalysts. J Chem Technol Biotechnol 87:1593–1599
Amen-Chen C, Pakdel H, Roy C (2001) Production of monomeric phenols by thermochemical conversion of biomass: a review. Bioresour Technol 79:277–299
Zakzeski J, Jongerius AL, Bruijnincx PCA, Weckhuysen BM (2012) Catalytic lignin valorization process for the production of aromatic chemicals and hydrogen. ChemSusChem 5:1602–1609
Bozell J (2014) Approaches to the selective catalytic conversion of lignin: a grand challenge for biorefinery development. In: Nicholas KM (ed) Selective catalysis for renewable feedstocks and chemicals. Springer, Berlin, pp 229–255
Harris EE, D’Ianni J, Adkins H (1938) Reaction of hardwood lignin with hydrogen. J Am Chem Soc 60:1467–1470
Kashima K, Maeda Y, Oshima M (1964) Method for liquefying lignin. Canadian Patent 700210
Engel DJ, Steigleder KZ (1987) Hydrocracking process for liquefaction of lignin. U.S. Patent 4,647,704
Urban P, Engel DJ (1988) Process for liquefaction of lignin U.S. Patent 4,731,491
Ratcliff MA, Johnson DK, Posey FL, Chum HL (1988) Hydrodeoxygenation of lignins and model compounds—scientific note. Appl Biochem Biotechnol 17:151–160
Meier D, Berns J, Faix O, Balfanz U, Baldauf W (1994) Hydrocracking of organocell lignin for phenol production. Biomass Bioenergy 7:99–105
Meier D, Ante R, Faix O (1992) Catalytic hydropyrolysis of lignin: influence of reaction conditions on the formation and composition of liquid products. Bioresour Technol 40:171–177
Oasmaa A, Alen R, Meier D (1993) Catalytic hydrotreatment of some technical lignins. Bioresour Technol 45:189–194
Oasmaa A, Johansson A (1993) Catalytic hydrotreating of lignin with water-soluble molybdenum catalyst. Energy Fuels 7:426–429
Torr KM, van de Pas DJ, Cazeils E, Suckling ID (2011) Mild hydrogenolysis of in-situ and isolated Pinus radiate lignins. Bioresour Technol 102:7608–7611
Horácek J, Homola F, Kubicková I, Kubicka D (2012) Lignin to liquids over sulfide catalysts. Catal Today 179:191–198
Song Q, Wang F, Xu J (2012) Hydrogenolysis of lignosulfonate into phenols over heterogeneous nickel catalysts. Chem Commun 48:7019–7021
Zhang JG, Asakura H, van Rijn J, Yang J, Duchesne P, Zhang B, Chen X, Zhang P, Saeys M, Yan N (2014) Highly efficient, NiAu-catalyzed hydrogenolysis of lignin into phenolic chemicals. Green Chem 16:2432–2437
Zhang JG, Teo J, Chen X, Asakura H, Tanaka T, Teramura K, Yan N (2014) A series of NiM (M = Ru, Rh, and Pd) bimetallic catalysts for effective lignin hydrogenolysis in water. ACS Catal 4:1574–1583
Ma XL, Tian Y, Hao WY, Ma R, Li YD (2014) Production of phenols from catalytic conversion of lignin over a tungsten phosphide catalyst. Appl Catal A 481:64–70
Xu W, Miller SJ, Agrawal PK, Jones CW (2012) Depolymerization and hydrodeoxygenation of switchgrass lignin with formic acid. ChemSusChem 5:667–675
Barta K, Warner GR, Beach ES, Anastas PT (2014) Depolymerization of organosolv lignin to aromatic compounds over Cu-doped porous metal oxides. Green Chem 16:191–196
Toledano A, Serrano L, Balu AM, Luque R, Pineda A, Labidi J (2013) Fractionation of organosolv lignin from olive tree clippings and its valorization to simple phenolic compounds. ChemSusChem 6:529–536
Toledano A, Serrano L, Pineda A, Romero AA, Luque R, Labidi J (2014) Microwave-assisted depolymerisation of organosolv lignin via mild hydrogen-free hydrogenolysis: catalyst screening. Appl Catal B Environ 145:43–55
Song Q, Wang F, Cai J, Wang Y, Zhang J, Yua W, Xu J (2013) Lignin depolymerization (LDP) in alcohol over nickel-based catalysts via a fragmentation–hydrogenolysis process. Energy Environ Sci 6:994–1007
Parsell T, Yohe S, Degenstein J, Jarrell T, Klein I, Gencer E, Hewetson B, Hurt M, Kim JI, ChoudhariH Saha B, Meilan R, Mosier N, Ribeiro F, Delgass WN, Chapple C, KenttamaaHI Agrawal R, Abu-Omar MM (2015) A synergistic biorefinery based on catalytic conversion of lignin prior to cellulose starting from lignocellulosic biomass. Green Chem 17:1492–1499
Vuori A, Bredenberg JB-S (1988) Liquefaction of Kraft lignin: 1. Primary reactions under mild thermolysis conditions. Holzforshung 42:155–161
Kleinert M, Barth T (2008) Phenols from lignin. Chem Eng Technol 31:736–745
Kleinert M, Barth T (2008) Towards a lignincellulosic biorefinery: direct one-step conversion of lignin to hydrogen-enriched biofuel. Energy Fuels 22:1371–1379
Wang X, Rinaldi R (2013) A route for lignin and bio-oil conversion: dehydroxylation of phenols into arenes by catalytic tandem reactions. Angew Chem Int Ed 52:11499–11503
Jongerius AL, Bruijnincx PCA, Weckhuysen BM (2013) Liquid-phase reforming and hydrodeoxygenation as a two-step route to aromatics from lignin. Green Chem 15:3049–3056
Yan N, Zhao C, Dyson PJ, Wang C, L-t Liu, Kou Y (2008) Selective degradation of wood lignin over noble-metal catalysts in a two-step process. ChemSusChem 1:626–629
Van den Bosch S, Schutyser W, Vanholme R, Driessen T, Koelewijn S-K, Renders T, De Meester B, Huijgen WJJ, Dehaen W, Courtin CM, Lagrain B, Boerjan W, Sels BF (2015) Reductive lignocellulose fractionation into soluble lignin-derived phenolic monomers and dimers and processable carbohydrate pulps. Energy Environ Sci 8:1748–1763
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. Bioorg Med Chem 13:2569–2578
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
Xiang Q, Lee YY (2001) Production of oxychemicals from precipitated hardwood lignin. Appl Biochem Biotechnol 91–93:71–80
Wu G, Heitz M (1995) Catalytic mechanism of Cu2+ and Fe3+ in alkaline O2 oxidation of lignin. J Wood Chem Technol 15:189–202
Bjørsvik H-R, Minisci F (1999) Fine chemicals from lignosulfonates. 1. Synthesis of vanillin by oxidation of lignosulfonates. Org Proc Res Dev 3:330–340
Azarpira A, Ralph J, Lu FC (2014) Catalytic alkaline oxidation of lignin and its model compounds: a pathway to aromatic biochemicals. BioEnergy Res 7:78–86
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
Sales FG, Maranhão LCA, Lima Filho NM, Abreu CAM (2007) Experimental evaluation and continuous catalytic process for fine aldehyde production from lignin. Chem Eng Sci 62:5386–5391
Deng HB, Lin L, Sun Y, Pang CS, Zhuang JP, Ouyang PK, Li ZJ, Liu SJ (2008) Perovskite-type oxide LaMnO3: an efficient and recyclable heterogeneous catalyst for the wet aerobic oxidation of lignin to aromatic aldehydes. Catal Lett 126:106–111
Zhou XF (2014) Selective oxidation of Kraft lignin over zeolite-encapsulated Co(II) [H4]salen and [H2]salen complexes. J Appl Polym Sci 131:40809(1-9)
Rahimi A, Azarpira A, Kim H, Ralph J, Stahl SS (2013) Chemoselective metal-free aerobic oxidation in lignin. J Am Chem Soc 135:6415–6418
Rahimi A, Ulbrich A, Coon JJ, Stahl SS (2014) Formic-acid-induced depolymerization of oxidized lignin to aromatics. Nature 515:249–252
Borges da Silva EA, Zabkova M, Araújo JD, Cateto CA, Belgacem MF, Barreiro MN, Rodrigues AE (2009) An integrated process to produce vanillin and lignin-based polyurethanes from Kraft lignin. Chem Eng Res Des 87:1276–1292
Wong JT (2012) Technological, commercial, organizational, and social uncertainties of a novel process for vanillin production from lignin. MBA Project, Simon Fraser University
Fache M, Boutevin B, Caillol S (2016) Vanillin production from lignin and its use as a renewable chemical. ACS Sustain Chem Eng 4:35–46
Fox MA, Dulay MT (1993) Heterogeneous photocatalysis. Chem Rev 93:341–357
Lathasree S, Nageswara R, Sivasankar B, Sadasivam V, Rengaraj K (2004) Heterogeneous photocatalytic mineralization of phenols in aqueous solutions. J Mol Catal A Chem 223:101–105
Kobayakawa K, Sato Y, Nakamura S, Fujishima A (1989) Photodecomposition of kraft lignin catalyzed by TiO2. Bull Chem Soc Jpn 62:3433–3436
Tanaka K, Calanag CR, Hisanaga T (1999) Photocatalyzed degradation of lignin on TiO2. J Mol Catal A Chem 138:287–294
Ksibi M, Ben Amor S, Cherif S, Elaloui E, Houas A, Elaloui M (2003) Photodegradation of lignin from black liquor using a UV/TiO2 system. J Photochem Photobiol A 154:211–218
Yuan RS, Guan RB, Liu P, Zheng JT (2007) Photocatalytic treatment of wastewater from paper mill by TiO2 loaded on activated carbon fibers. Colloids Surf A 293:80–86
Ma YS, Chang CN, Chiang YP, Sung HF, Chao AC (2008) Photocatalytic degradation of lignin using Pt/TiO2 as the catalyst. Chemosphere 71:998–1004
Ugurlu M, Karaoglu MH (2009) Removal of AOX, total nitrogen and chlorinated lignin from bleached Kraft mill effluents by UV oxidation in the presence of hydrogen peroxide utilizing TiO2 as photocatalyst. Environ Sci Pollut Res 16:265–273
Ugurlu M, Karaoglu MH (2011) TiO2 supported on sepiolite: preparation, structural and thermal characterization and catalytic behaviour in photocatalytic treatment of phenol and lignin from olive mill wastewater. Chem Eng J 166:859–867
Ugurlu M, Karaoglu MH, Vaizogullar AI (2013) Decolourization and removal of phenol compounds from olive mill wastewater byO2/UV/NaBO2H2O2-SH2O. Fresenius Environ Bull 22:752–763
Portjanskaja E, Stepanova K, Klauson D, Preis S (2009) The influence of titanium dioxide modifications on photocatalytic oxidation of lignin and humic acids. Catal Today 144:26–30
Portjanskaja E, Preis S (2007) Aqueous photocatalytic oxidation of lignin: the influence of mineral admixtures. Int J Photoenergy 76730:1–7
Rangel R, Mercado GJL, Bartolo-Perez P, Garcia R (2012) Nanostructured-[CeO2, La2O3, C]/TiO2catalysts for lignin photodegradation. Sci Adv Mater 4:573–578
Kansal SK, Singh M, Sud D (2008) Studies on TiO2/ZnO photocatalysed degradation of lignin. J Hazard Mater 153:412–417
Kamwilaisak K, Wright PC (2012) Investigating laccase and titanium dioxide for lignin degradation. Energy Fuels 26:2400–2406
Tonucci L, Coccia F, Bressan M, Alessandro N (2012) Mild photocatalysed and catalysed green oxidation of lignin: A useful pathway to low-molecular-weight derivatives. Waste Biomass Valorization 3:165–174
Bailey A, Brooks HM (1946) Electrolytic oxidation of lignin. J Am Chem Soc 68:445–446
Moodley B, Mulholland DA, Brookes HC (2011) The electrooxidation of lignin in Sappi Saiccor dissolving pulp mill effluent. Water SA 37:33–40
Tolba R, Tian M, Wen J, Jiang Z-H, Chen A (2010) Electrochemical oxidation of lignin at IrO 2-based oxide electrodes. J Electroanal Chem 649:9–15
Shao D, Liang JD, Cui XM, Xu H, Yan W (2014) Electrochemical oxidation of lignin by two typical electrodes: Ti/Sb-SnO2 and Ti/PbO2. Chem Eng J 244:288–295
Zhu HB, Chen YM, Qin TF, Wang L, Tang Y, SunYZ Wan PY (2014) Lignin depolymerization via an integrated approach of anode oxidation and electro-generated H2O2 oxidation. RSC Adv 4:6232–6238
Constant S, Robitzer M, Quignard F, Di Renzo F (2012) Vanillin oligomerization as a model of side reactions in lignin fragmentation. Catal Today 189:123–128
Parpot P, Bettencourt AP, Carvalho AM, Belgsir EM (2000) Biomass conversion: attempted electrooxidation of lignin for vanillin production. J Appl Electrochem 30:727–731
Tian M, Wen J, MacDonald D, Asmussen RM, Chen A (2010) A novel approach for lignin modification and degradation. Electrochem Commun 12:527–530
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
Wasserscheid P, Stark A (eds) (2010) Handbook of green chemistry: green solvents, vol 6—ionic liquids, Wiley-VCH
Peleteiro S, Rivas S, Alonso JL, Santos V, Parajo JC (2015) Utilization of ionic liquids in lignocellulose biorefineries as agents for separation, derivatization, fractionation, or pretreatment. J Agric Food Chem 63:8093–8102
Olivier-Bourbigou H, Magna L, Morvan D (2010) Ionic liquids and catalysis: Recent progress from knowledge to applications. Appl Catal A 373:1–56
Stark A (2011) Ionic liquids in the biorefinery: a critical assessment of their potential. Energy Environ Sci 4:19–32
Hossain MM, Aldous L (2012) Ionic liquids for lignin processing: dissolution, isolation, and conversion. Aust J Chem 65:1465–1477
Plechkova NV, Seddon KR (2008) Applications of ionic liquids in the chemical industry. Chem Soc Rev 37:123–150
Parvulescu VI, Hardacre C (2007) Catalysis in ionic liquids. Chem Rev 107:2615–2665
Swatloski RP, Spear SK, Holbrey JD, Rogers RD (2002) Dissolution of cellulose with ionic liquids. J Am Chem Soc 124:4974–4975
Sun N, Rahman M, Qin Y, Maxim ML, Rodriguez H, Rogers RD (2009) Complete dissolution and partial delignification of wood in the ionic liquid 1-ethyl-3-methylimidazolium acetate. Green Chem 11:646–655
Lee SH, Doherty TV, Linhardt JS (2009) Ionic liquid-mediated selective extraction of lignin from wood leading to enhanced enzymatic cellulose hydrolysis. Biotechnol Bioeng 102:1368–1376
Fu D, Mazza G, Tamaki Y (2010) Lignin extraction from straw by ionic liquids and enzymatic hydrolysis of the cellulosic residues. J Agric Food Chem 58:2915–2922
Zhu S, Wu Y, Chen Q, Yu Z, Wang C, Jin S, Ding Y, Wu G (2006) Dissolution of cellulose with ionic liquids and its application: a mini-review. Green Chem 8:325–327
Pinkert A, Marsh KN, Pang SS, Staiger MP (2009) Ionic liquids and their interaction with cellulose. Chem Rev 109:6712–6728
Maki-Arvela P, Anugwom I, Virtanen P, Sjoholm R, Mikkola JP (2010) Dissolution of lignocellulosic materials and its constituents using ionic liquids—a review. Ind Crop Prod 32:175–201
Mora-Pale M, Meli L, Doherty TV, Linhardt RJ, Dordick JS (2011) Room temperature ionic liquids as emerging solvents for the pretreatment of lignocellulosic biomass. Biotechnol Bioeng 108:1229–1245
Wang H, Gurau G, Rogers RD (2012) Ionic liquid processing of cellulose. Chem Soc Rev 41:1519–1537
Kim J-Y, Shin E-J, Eoma I-Y, Wonb K, Kim YH, Choi D, Choi IG, Choi JW (2011) Structural features of lignin macromolecules extracted with ionic liquid from poplar wood. Bioresour Technol 102:9020–9025
Li W, Sun N, Stoner B, Jiang X, Lu X, Rogers RD (2011) Rapid dissolution of lignocellulosic biomass in ionic liquids using temperatures above the glass transition of lignin. Green Chem 13:2038–2047
Brandt A, Grasvik J, Hallett JP, Welton T (2013) Deconstruction of lignocellulosic biomass with ionic liquids. Green Chem 15:550–583
Zavrel M, Bross D, Funke M, Buchs J, Spiess AC (2009) High-throughput screening for ionic liquids dissolving (ligno-)cellulose. Bioresour Technol 100:2580–2587
Tan SSY, MacFarlane DR (2009) Ionic liquids in biomass processing. Top Curr Chem 290:311–339
Tan SSY, MacFarlane DR, Upfal J, Edye LA, Doherty WOS, Patti AF, Pringle JM, Scott JL (2009) Extraction of lignin from lignocellulose at atmospheric pressure using alkylbenzenesulfonate ionic liquid. Green Chem 11:339–345
Pinkert A, Goeke DF, Marsh KN, Pang S (2011) Extracting wood lignin without dissolving or degrading cellulose: investigations on the use of food additive-derived ionic liquids. Green Chem 13:3124–3136
Pu Y, Jiang N, Ragauskas AJ (2007) Ionic liquid as a green solvent for lignin. J Wood Chem Technol 27:23–33
Wang Y, Wei L, Li K, Ma Y, Ma N, Ding S, Wang L, Zhao D, Yan B, Wan W, Zhang Q, Wang X, Wang J, Li H (2014) Lignin dissolution in dialkylimidazolium-based ionic liquid–water mixtures. Bioresour Technol 170:499–505
Lateef H, Grimes S, Kewcharoenwong P, Feinberg B (2009) Separation and recovery of cellulose and lignin using ionic liquids: a process for recovery from paper-based waste. J Chem Technol Biotechnol 84:1818–1827
Diop A, Bouazza AH, Daneault C, Montplaisir D (2013) New ionic liquid for the dissolution of lignin. Bioresoure 8:4270–4282
Kilpelainen I, Xie H, King A, Granstrom M, Heikkinen S, Argyropoulos DS (2007) Dissolution of wood in ionic liquids. J Agric Food Chem 55:9142–9148
George A, Tran K, Morgan TJ, Benke PI, Berrueco C, Lorente E, Wu BC, Keasling JD, Simmons BA, Holmes BM (2011) The effect of ionic liquid cation and anion combinations on the macromolecular structure of lignins. Green Chem 13:3375–3385
Li B, Filpponen I, Argyropoulos DS (2010) Acidolysis of wood in ionic liquids. Ind Eng Chem Res 49:3126–3136
Cox BJ, Ekerdt JG (2012) Depolymerization of oak wood lignin under mild conditions using the acidic ionic liquid 1-H-3-methylimidazolium chloride as both solvent and catalyst. Bioresour Technol 118:584–588
Stärk K, Taccardi N, Bösmann A, Wasserscheid P (2010) Oxidative depolymerization of lignin in ionic liquids. ChemSusChem 3:719–723
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
Zakzeski J, Bruijnincx PCA, Weckhuysen BM (2011) In situ spectroscopic investigation of the cobalt-catalyzed oxidation of lignin model compounds in ionic liquids. Green Chem 13:671–680
Liu S, Shi ZL, Li L, Yu ST, Xie C, Song Z (2013) Process of lignin oxidation in an ionic liquid coupled with separation. RSC Adv 3:5789–5793
Sena-Martins G, Almeida-Vara E, Duarte JC (2008) Eco-friendly new products from enzymatically modified industrial lignins. Ind Crop Prod 27:189–195
Bugg TDH, Ahmad M, Hardiman EM, Rahmanpour R (2011) Pathways for degradation of lignin in bacteria and fungi. Nat Prod Rep 28:1883–1896
Kirk TK, Farrell RL (1987) Enzymatic ‘‘combustion’’: the microbial degradation of lignin. Annu Rev Microbiol 41:465–505
Ten Have R, Teunissen PJM (2001) Oxidative mechanisms involved in lignin degradation by white-rot fungi. Chem Rev 101:3397–3413
Ahmad M, Taylor CR, Pink D, Burton K, Eastwood D, Bending GD, Bugg TDH (2010) Development of novel assays for lignin degradation: comparative analysis of bacterial and fungal lignin degraders. Mol BioSyst 6:815–821
Hatakka A, Hammel KE (2010) Fungal biodegradation of lignocelluloses. In: The Mycota. Industrial Applications, 10, pp 319–340
Vicuna R (1988) Bacterial degradation of lignin. Enzyme Microb Technol 10:646–655
Zimmermann W (1990) Degradation of lignin by bacteria. J Biotechnol 13:119–130
Bugg TDH, Ahmad M, Hardiman EM, Singh R (2011) The emerging role for bacteria in lignin degradation and bio-product formation. Curr Opin Biotechnol 22:394–400
Bandounas L, Wierckx NJP, de Winde JH, Ruijssenaars HJ (2011) Isolation and characterization of novel bacterial strains exhibiting ligninolytic potential. BMC Biotechnol 11:94
Brown ME, Chang MCY (2014) Exploring bacterial lignin degradation. Curr Opin Chem Biol 19:1–7
Dey S, Maiti TK, Bhattacharyya BC (1994) Production of some extracellular enzymes by a lignin peroxidase-producing brown rot fungus, Polyporus ostreiformis, and its comparative abilities for lignin degradation and dye decolorization. Appl Environ Microbiol 60:4216–4218
Paliwal R, Rawat AP, Rawat M, Rai JPN (2012) Bioligninolysis: recent updates for biotechnological solution. Appl Biochem Biotechnol 167:1865–1889
DeAngelis KM, Allgaier M, Chavarria Y, Fortney JL, Hugenholtz P, Simmons B, Sublette K, Silver WL, Hazen TC (2011) Characterization of trapped lignin-degrading microbes in tropical forest soil. PLoS ONE 6:e19306
Taylor CR, Hardiman EM, Ahmad M, Sainsbury PD, Norris PR, Bugg TDH (2012) Isolation of bacterial strains able to metabolize lignin from screening of environmental samples. J Appl Microbiol 113:521–530
Huang X-F, Santhanam N, Badri DV, Hunter WJ, Manter DK, Decker SR, Vivanco JM, Reardon KF (2013) Isolation and characterization of lignin-degrading bacteria from rainforest soils. Biotechnol Bioeng 110:1616–1626
Pasti MB, Pometto AL, Nuti MP, Crawford DL (1990) Lignin-solubilizing ability of actinomycetes isolated from termite (Termitidae) gut. Appl Environ Microbiol 56:2213–2218
Kato K, Kosaki S, Sakuranaga M (1998) Degradation of lignin compounds by bacteria from termite guts. Biotechnol Lett 20:459–462
Pollegioni L, Tonin F, Rosini E (2015) Lignin-degrading enzymes. FEBS J 282:1190–1213
Haemmerli SD, Leisola MSA, Fiechter A (1986) Polymerisation of lignins by ligninases from Phanerochaete chrysosporium. FEMS Microbiol Lett 35:33–36
Hammel KE, Jensen KA, Mozuch MD, Landucci LL, Tien M, Pease EA (1993) Ligninolysis by a purified lignin peroxidase. J Biol Chem 268:12274–12281
Conesa A, Punt PJ, van den Hondel CAMJJ (2002) Fungal peroxidases: molecular aspects and applications. J Biotechnol 93:143–158
Munk L, Sitarz AK, Kalyani DC, Mikkelsen JD, Meyer AS (2015) Can laccases catalyze bond cleavage in lignin? Biotechnol Adv 33:13–24
Rochefort D, Leech D, Bourbonnais R (2004) Electron transfer mediator systems for bleaching of paper pulp. Green Chem 6:14–24
Reiter J, Strittmatter H, Wiemann LO, Schieder D, Sieber V (2013) Enzymatic cleavage of lignin beta-O-4-aryl ether bonds via net internal hydrogen transfer. Green Chem 15:1373–1381
Otsuka Y, Sonoki T, Ikeda S, Kajita S, Nakamura M, Katayama Y (2003) Detection and characterization of a novel extracellular fungal enzyme that catalyzes the specific and hydrolytic cleavage of lignin guaiacyl glycerol beta-aryl ether linkages. Eur J Biochem 270:2353–2362
Masai E, Ichimura A, Sato Y, Miyauchi K, Katayama Y, Fukuda M (2003) Roles of the enantioselective glutathione S-transferases in cleavage of β-aryl ether. J Bacteriol 185:1768–1775
Allocati N, Federici L, Masulli M, DiIlio C (2009) Glutathione transferases in bacteria. FEBS J 276:58–75
Gall DL, Kim H, Lu F, Donohoe TJ, Noguera DR, Ralph J (2014) Stereochemical features of glutathione-dependent enzymes in the Sphingobium sp. strain SYK-6 β-aryl etherase pathway. J Biol Chem 289:8656–8667
Picart P, Müller C, Mottweiler J, Wiermans L, Bolm C, Dominguez de Maria P, Schallmey A (2014) From gene towards selective biomass valorization: bacterial β-etherases with catalytic activity on lignin-like polymers. ChemSusChem 7:3164–3171
Masai E, Sasaki M, Minakawa Y, Abe T, Sonoki T, Miyauchi K, Katayama Y, Fukuda M (2004) A novel tetrahydrofolate-dependent O-demethylase gene is essential for growth of Sphingomonas paucimobilis SYK-6 with syringate. J Bacteriol 186:2757–2765
Bugg TDH, Rahmanpour R (2015) Enzymatic conversion of lignin into renewable chemicals. Curr Opin Chem Biol 29:10–17
Chen CL, Chang HM, Kirk TK (1983) Carboxylic acids produced through oxidative cleavage of aromatic rings during degradation of lignin in spruce wood by Phanerochaete chrysosporium. J Wood Chem Technol 3:35–57
Sainsbury PD, Hardiman EM, Ahmad M, Otani H, Seghezzi N, Eltis LD, Bugg TDH (2013) Breaking down lignin to high-value chemicals: the conversion of lignocellulose to vanillin in a gene deletion mutant of Rhodococcus jostii RHA1. ACS Chem Biol 8:2151–2156
Vardon DR, Franden MA, Johnson CW, Karp EM, Guarneri MT, Linger JG, Salm MJ, Strathman TJ, Beckham GT (2015) Adipic acid production from lignin. Energy Environ Sci 8:617–628
Kiiskinen LL, Saloheimo M (2004) Molecular cloning and expression in Saccharomyces cerevisiae of a laccase gene from the ascomycete Melanocarpus albomyces. Appl Environ Microbiol 70:137–144
Kim S, Chmely SC, Nimos MR, Bomble YJ, Foust TD, Paton RS, Beckham GT (2011) Computational study of bond dissociation enthalpies for a large range of native and modified lignins. J Phys Chem Lett 2:2846–2852
Parthasarathi R, Romero RA, Redondo A, Gnanakaran S (2011) Theoretical study of the remarkably diverse linkages in lignin. J Phys Chem Lett 2:2660–2666
Beste A, Buchanan AC III (2009) Computational study of bond dissociation enthalpies for lignin model compounds. Substituent effects in phenethyl phenyl ethers. J Org Chem 74:2837–2841
Younker JM, Beste A, Buchanan AC III (2011) Computational study of bond dissociation enthalpies for substituted β-O-4 lignin model compounds. ChemPhysChem 12:3556–3565
Beste A, Buchanan AC III (2011) Kinetic analysis of the phenyl-shift reaction in β-O-4 lignin model compounds: a computational study. J Org Chem 76:2195–2203
Beste A, Buchanan AC III (2012) Role of carbon–carbon phenyl migration in the pyrolysis mechanism of β-O-4 lignin model compounds: phenethyl phenyl ether and α-hydroxy phenethyl phenyl ether. J Phys Chem A 116:12242–12248
Beste A, Buchanan AC III, Harrison RJ (2008) Computational prediction of α/β selectivities in the pyrolysis of oxygen-substituted phenethyl phenyl ethers. J Phys Chem A 112:4982–4988
Beste A, Buchanan AC III (2012) Kinetic simulation of the thermal degradation of phenethyl phenyl ether, a model compound for the β-O-4 linkage in lignin. Chem Phys Lett 550:19–24
Beste A, Buchanan AC III (2013) Computational investigation of the pyrolysis product selectivity for α-hydroxy phenethyl phenyl ether and phenethyl phenyl ether: analysis of substituent effects and reactant conformer selection. J Phys Chem A 117:3235–3242
Mar BD, Qi HW, Liu F, Kulik HJ (2015) Ab initio screening approach for the discovery of lignin polymer breaking pathways. J Phys Chem A 119:6551–6562
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2016 Springer-Verlag GmbH Germany
About this chapter
Cite this chapter
Monteil-Rivera, F. (2016). Green Processes for Lignin Conversion. In: C.K. Lau, P. (eds) Quality Living Through Chemurgy and Green Chemistry. Green Chemistry and Sustainable Technology. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-662-53704-6_10
Download citation
DOI: https://doi.org/10.1007/978-3-662-53704-6_10
Published:
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-662-53702-2
Online ISBN: 978-3-662-53704-6
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)