Abstract
Over the past few years, lignin is seen as the remaining part after paper production or biofuels extraction; the most common method to get rid of it by giving it a profitable use has been burning it in a recovery container for steam production which provides enough energy to power their processes. However, the increase in production has left a higher volume of residual lignin than energy demand. So this vast amount of lignin produced as a by-product has gained increasing interest and attention of researchers to use it as a bio-sourced to develop value-added materials. Lignin has a complex structure with phenolic and aliphatic hydroxyl groups, which make it a promising alternative for the production of several chemical compounds. Different chemical modifications have been applied to transform lignin into new materials, either by polymerization which uses lignin as a monomer in the synthesis of polymers or either by creating new reactive sites or by structural modification of the functional groups already existing in the lignin. In addition to that, depolymerization of lignin is another option which involves its fragmentation into smaller molecules having higher reactivity that can be utilized for the synthesis of biobased polymers and biofuels.
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References
Abas N, Kalair A, Khan N (2015) Review of fossil fuels and future energy technologies. Futures 69:31–49. https://doi.org/10.1016/J.FUTURES.2015.03.003
Abdel-Hamid AM, Solbiati JO, Cann IKO (2013) Insights into lignin degradation and its potential industrial applications. Adv Appl Microbiol 82:1–28. https://doi.org/10.1016/B978-0-12-407679-2.00001-6
Agarwal A, Rana M, Park JH (2018) Advancement in technologies for the depolymerization of lignin. Fuel Process Technol 181:115–132. https://doi.org/10.1016/j.fuproc.2018.09.017
Aki SNVK, Brennecke JF, Samanta A (2001) How polar are room-temperature ionic liquids? Chem Commun 413–414. https://doi.org/10.1039/b008039j
Aro T, Fatehi P (2017) Production and application of lignosulfonates and sulfonated lignin. ChemSuschem 10:1861–1877
Asada C, Basnet S, Otsuka M et al (2015) Epoxy resin synthesis using low molecular weight lignin separated from various lignocellulosic materials. Int J Biol Macromol 74:413–419. https://doi.org/10.1016/j.ijbiomac.2014.12.039
Beckham GT, Johnson CW, Karp EM et al (2016) Opportunities and challenges in biological lignin valorization. Curr Opin Biotechnol 42:40–53. https://doi.org/10.1016/j.copbio.2016.02.030
Belkheiri T, Andersson SI, Mattsson C et al (2018) Hydrothermal liquefaction of Kraft lignin in subcritical water: influence of phenol as capping agent. Energy Fuels 32:5923–5932. https://doi.org/10.1021/acs.energyfuels.8b00068
Bernardini J, Cinelli P, Anguillesi I et al (2015) Flexible polyurethane foams green production employing lignin or oxypropylated lignin. Eur Polym J 64:147–156. https://doi.org/10.1016/j.eurpolymj.2014.11.039
Bi Z, Li Z, Yan L (2018) Catalytic oxidation of lignin to dicarboxylic acid over the CuFeS2 nanoparticle catalyst. Green Process Synth 7:306–315. https://doi.org/10.1515/gps-2017-0056
Brown ME, Chang MCY (2014) Exploring bacterial lignin degradation. Curr Opin Chem Biol 19:1–7. https://doi.org/10.1016/j.cbpa.2013.11.015
Bu Q, Lei H, Wang L et al (2014) Bio-based phenols and fuel production from catalytic microwave pyrolysis of lignin by activated carbons. Bioresour Technol. 162:142–147. https://doi.org/10.1016/j.biortech.2014.03.103
Calvo-Flores FG, Dobado JA (2010) Lignin as renewable raw material. ChemSuschem 3:1227–1235. https://doi.org/10.1002/cssc.201000157
Cao C, Xu L, He Y et al (2017) High-efficiency gasification of wheat straw black liquor in supercritical water at high temperatures for hydrogen production. Energy Fuels 31:3970–3978. https://doi.org/10.1021/acs.energyfuels.6b03002
Capellán-Pérez I, Mediavilla M, de Castro C et al (2014) Fossil fuel depletion and socio-economic scenarios: an integrated approach. Energy 77:641–666. https://doi.org/10.1016/J.ENERGY.2014.09.063
Cardoso A, Ramirez Reina T, Suelves I et al (2018) Effect of carbon-based materials and CeO 2 on Ni catalysts for kraft lignin liquefaction in supercritical water. Green Chem 20:4308–4318. https://doi.org/10.1039/c8gc02210k
Cateto CA, Barreiro MF, Rodrigues AE, Belgacem MN (2009) Optimization study of lignin oxypropylation in view of the preparation of polyurethane rigid foams. Ind Eng Chem Res 48:2583–2589. https://doi.org/10.1021/ie801251r
Cateto CA, Barreiro MF, Ottati C et al (2014) Lignin-based rigid polyurethane foams with improved biodegradation. J Cell Plast 50:81–95. https://doi.org/10.1177/0021955X13504774
Çetinkol ÖP, Dibble DC, Cheng G et al (2010) Understanding the impact of ionic liquid pretreatment on eucalyptus. Biofuels 1:33–46. https://doi.org/10.4155/bfs.09.5
Chadwick SS (1988) Ullmann’s encyclopedia of industrial chemistry. Wiley
Chen MQ, Wang J, Zhang MX et al (2008) Catalytic effects of eight inorganic additives on pyrolysis of pine wood sawdust by microwave heating. J Anal Appl Pyrolysis 82:145–150. https://doi.org/10.1016/j.jaap.2008.03.001
Cheng S, Yuan Z, Anderson M et al (2012) Synthesis of biobased phenolic resins/adhesives with methylolated wood-derived bio-oil. J Appl Polym Sci 126:E431–E441. https://doi.org/10.1002/app.35655
Chio C, Sain M, Qin W (2019) Lignin utilization: a review of lignin depolymerization from various aspects. Renew Sustain Energy Rev 107:232–249. https://doi.org/10.1016/j.rser.2019.03.008
Ciuta S, Tsiamis D, Castaldi MJ (2018) Fundamentals of gasification and pyrolysis. In: Ciuta S, Tsiamis D, Castaldi MJ (eds) Gasification of waste materials. Academic Press, pp 13–36
Cotana F, Cavalaglio G, Nicolini A et al (2014) Lignin as co-product of second generation bioethanol production from ligno-cellulosic biomass. Energy Procedia 45:52–60. https://doi.org/10.1016/j.egypro.2014.01.007
Cronin DJ, Dunn K, Zhang X, Doherty WOS (2017a) Relating dicarboxylic acid yield to residual lignin structural features. ACS Sustain Chem Eng 5:11695–11705. https://doi.org/10.1021/acssuschemeng.7b03164
Cronin DJ, Zhang X, Bartley J, Doherty WOS (2017b) Lignin depolymerization to dicarboxylic acids with sodium percarbonate. ACS Sustain Chem Eng 5:6253–6260. https://doi.org/10.1021/acssuschemeng.7b01208
D’Souza J, George B, Camargo R, Yan N (2015) Synthesis and characterization of bio-polyols through the oxypropylation of bark and alkaline extracts of bark. Ind Crops Prod 76:1–11. https://doi.org/10.1016/j.indcrop.2015.06.037
Das L, Xu S, Shi J (2017) Catalytic oxidation and depolymerization of lignin in aqueous ionic liquid. Front Energy Res 5:1–12. https://doi.org/10.3389/fenrg.2017.00021
Dehne L, Vila Babarro C, Saake B, Schwarz KU (2016) Influence of lignin source and esterification on properties of lignin-polyethylene blends. Ind Crops Prod 86:320–328. https://doi.org/10.1016/j.indcrop.2016.04.005
Dhar P, Vinu R (2017) Understanding lignin depolymerization to phenols via microwave-assisted solvolysis process. J Environ Chem Eng 5:4759–4768. https://doi.org/10.1016/j.jece.2017.08.031
Dias AA, Freitas GS, Marques GSM et al (2010) Enzymatic saccharification of biologically pre-treated wheat straw with white-rot fungi. Bioresour Technol 101:6045–6050. https://doi.org/10.1016/j.biortech.2010.02.110
Ding N, Wang X, Tian Y, et al (2014) A renewable agricultural waste material for the syntehsis of the novel thermal stability epoxy resins. Polym Eng Sci 2777–2784. https://doi.org/10.1002/pen.23838
Dong C, Feng C, Liu Q et al (2014) Mechanism on microwave-assisted acidic solvolysis of black-liquor lignin. Bioresour Technol 162:136–141. https://doi.org/10.1016/j.biortech.2014.03.060
Du X, Li J, Lindström ME (2014) Modification of industrial softwood kraft lignin using Mannich reaction with and without phenolation pretreatment. Ind Crops Prod 52:729–735. https://doi.org/10.1016/j.indcrop.2013.11.035
Duan D, Ruan R, Lei H et al (2018a) Microwave-assisted co-pyrolysis of pretreated lignin and soapstock for upgrading liquid oil: effect of pretreatment parameters on pyrolysis behavior. Bioresour Technol 258:98–104. https://doi.org/10.1016/j.biortech.2018.02.119
Duan D, Ruan R, Wang Y et al (2018b) Microwave-assisted acid pretreatment of alkali lignin: effect on characteristics and pyrolysis behavior. Bioresour Technol 251:57–62. https://doi.org/10.1016/j.biortech.2017.12.022
Duan D, Wang Y, Ruan R et al (2018c) Comparative study on various alcohols solvolysis of organosolv lignin using microwave energy: physicochemical and morphological properties. Chem Eng Process Process Intensif 126:38–44. https://doi.org/10.1016/j.cep.2017.10.023
Duval A, Lawoko M (2014) A review on lignin-based polymeric, micro- and nano-structured materials. React Funct Polym 85:78–96. https://doi.org/10.1016/j.reactfunctpolym.2014.09.017
El Mansouri N-E, Pizzi A, Salvado J (2007) Lignin-based polycondensation resins for wood adhesives. J Appl Polym Sci 103:1690–1699. https://doi.org/10.1002/app.25098
El Mansouri N-E, Yuan Q, Huang F (2011a) Study of chemical modification of alkaline lignin by the glyoxalation reaction. BioResources 6:4523–4536
El Mansouri N-E, Yuan Q, Huang F (2011b) Synthesis and characterization of kraft lignin-based epoxy resins. BioResources 6:2492–2503
Espinoza-Acosta JL, Torres-Chávez PI, Olmedo-MartÃnez JL et al (2018) Lignin in storage and renewable energy applications: a review. J Energy Chem 27:1422–1438. https://doi.org/10.1016/J.JECHEM.2018.02.015
Fache M, Auvergne R, Boutevin B, Caillol S (2015) New vanillin-derived diepoxy monomers for the synthesis of biobased thermosets. Eur Polym J 67:527–538. https://doi.org/10.1016/j.eurpolymj.2014.10.011
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. https://doi.org/10.1021/acssuschemeng.5b01344
Fahmy TYA, Fahmy Y, Mobarak F, et al (2020) Biomass pyrolysis: past, present, and future. Environ Dev Sustain 22:17–32. https://doi.org/10.1007/s10668-018-0200-5
Fang Z, Smith RL (eds) (2016) Production of Biofuels and Chemicals from Lignin. Springer Singapore, Singapore
Fang Z, Smith RL Jr, Xinhua Qi (2015) Production of biofuels and chemicals with microwave. Springer, Dordrecht
Fernández-RodrÃguez J, Erdocia X, Sánchez C et al (2017) Lignin depolymerization for phenolic monomers production by sustainable processes. J Energy Chem 26:622–631. https://doi.org/10.1016/j.jechem.2017.02.007
Figueiredo P, Lintinen K, Hirvonen JT et al (2018) Properties and chemical modifications of lignin: towards lignin-based nanomaterials for biomedical applications. Prog Mater Sci 93:233–269. https://doi.org/10.1016/j.pmatsci.2017.12.001
Foyer G, Chanfi BH, Boutevin B et al (2016) New method for the synthesis of formaldehyde-free phenolic resins from lignin-based aldehyde precursors. Eur Polym J 74:296–309. https://doi.org/10.1016/j.eurpolymj.2015.11.036
Fu D, Farag S, Chaouki J, Jessop PG (2014) Extraction of phenols from lignin microwave-pyrolysis oil using a switchable hydrophilicity solvent. Bioresour Technol 154:101–108. https://doi.org/10.1016/j.biortech.2013.11.091
Funkenbusch LLT, Mullins ME, Vamling L et al (2019) Technoeconomic assessment of hydrothermal liquefaction oil from lignin with catalytic upgrading for renewable fuel and chemical production. WIREs Energy Environ 8:e319 8. https://doi.org/10.1002/wene.319
Gang H, Lee D, Choi K-Y et al (2017) Development of High performance polyurethane elastomers using vanillin-based green polyol chain extender originating from lignocellulosic biomass. ACS Sustain Chem Eng 5:4582–4588. https://doi.org/10.1021/acssuschemeng.6b02960
Goldmann WM, Anthonykutty JM, Ahola J et al (2019) Effect of process variables on the solvolysis depolymerization of pine kraft lignin. Waste Biomass Valorization. https://doi.org/10.1007/s12649-019-00701-1
Gordobil O, Herrera R, Llano-Ponte R, Labidi J (2017) Esterified organosolv lignin as hydrophobic agent for use on wood products. Prog Org Coat 103:143–151. https://doi.org/10.1016/J.PORGCOAT.2016.10.030
Güvenatam B (2015) Catalytic pathways for lignin depolymerization. Technische Universiteit Eindhoven, Eindhoven
Güvenatam B, Heeres EHJ, Pidko EA, Hensen EJM (2016) Lewis-acid catalyzed depolymerization of protobind lignin in supercritical water and ethanol. Catal Today 259:460–466. https://doi.org/10.1016/J.CATTOD.2015.03.041
Hayati AN, Evans DAC, Laycock B et al (2018) A simple methodology for improving the performance and sustainability of rigid polyurethane foam by incorporating industrial lignin. Ind Crops Prod 117:149–158. https://doi.org/10.1016/j.indcrop.2018.03.006
Hong Y, Dashtban M (2015) Lignin in paper mill sludge is degraded by white-rot fungi in submerged fermentation. J Microb Biochem Technol 07:04
Höök M, Tang X (2013) Depletion of fossil fuels and anthropogenic climate change—a review. Energy Policy 52:797–809. https://doi.org/10.1016/J.ENPOL.2012.10.046
Hu L, Pan H, Zhou Y, Zhang M (2011) Methods to improve lignin’s reactivity as a phenol substitute and as replacement for other phenolic compounds: a brief review. BioResources 6:3515–3525. https://doi.org/10.15376/biores.6.3.3515-3525
Hu S, Luo X, Li Y (2014) Polyols and polyurethanes from the liquefaction of lignocellulosic biomass. ChemSuschem 7:66–72. https://doi.org/10.1002/cssc.201300760
Huang YF, Kuan WH, Lo SL, Lin CF (2008) Total recovery of resources and energy from rice straw using microwave-induced pyrolysis. Bioresour Technol 99:8252–8258. https://doi.org/10.1016/J.BIORTECH.2008.03.026
Huang Y-F, Chiueh P-T, Lo S-L (2016) A review on microwave pyrolysis of lignocellulosic biomass. Sustain Environ Res 26:103–109. https://doi.org/10.1016/J.SERJ.2016.04.012
Jablonskis A, Arshanitsa A, Arnautov A et al (2018) Evaluation of Ligno BoostTM softwood kraft lignin epoxidation as an approach for its application in cured epoxy resins. Ind Crops Prod 112:225–235. https://doi.org/10.1016/j.indcrop.2017.12.003
Jiang Y, Loos K (2016) Enzymatic synthesis of biobased polyesters and polyamides. Polymers 8:243. https://doi.org/10.3390/polym8070243
Jiang X, Liu J, Du X et al (2018) Phenolation to improve lignin reactivity toward thermosets application. ACS Sustain Chem Eng 6:5504–5512. https://doi.org/10.1021/acssuschemeng.8b00369
Jiao GJ, Peng P, Sun SL et al (2019) Amination of biorefinery technical lignin by Mannich reaction for preparing highly efficient nitrogen fertilizer. Int J Biol Macromol 127:544–554. https://doi.org/10.1016/j.ijbiomac.2019.01.076
Kai D, Zhang K, Jiang L et al (2017) Sustainable and antioxidant lignin-polyester copolymers and nanofibers for potential healthcare applications. ACS Sustain Chem Eng 5:6016–6025. https://doi.org/10.1021/acssuschemeng.7b00850
Kalami S, Arefmanesh M, Master E, Nejad M (2017) Replacing 100% of phenol in phenolic adhesive formulations with lignin. J Appl Polym Sci 134:45124. https://doi.org/10.1002/app.45124
Kalami S, Chen N, Borazjani H, Nejad M (2018) Comparative analysis of different lignins as phenol replacement in phenolic adhesive formulations. Ind Crops Prod 125:520–528. https://doi.org/10.1016/j.indcrop.2018.09.037
Kang K, Azargohar R, Dalai AK, Wang H (2015) Noncatalytic gasification of lignin in supercritical water using a batch reactor for hydrogen production: an experimental and modeling study. Energy Fuels 29:1776–1784. https://doi.org/10.1021/ef5027345
Karak N (2016) Biopolymers for paints and surface coatings. In: Pacheco-Torgal F, Ivanov V, Niranjan K, Jonkers H (eds) Biopolymers and biotech admixtures for eco-efficient construction materials. Woodhead Publishing, pp 333–368
Kawamoto H (2017) Lignin pyrolysis reactions. J Wood Sci 63:117–132. https://doi.org/10.1007/s10086-016-1606-z
Kawamoto H, Horigoshi S, Saka S (2007) Pyrolysis reactions of various lignin model dimers. J Wood Sci 53:168–174. https://doi.org/10.1007/s10086-006-0834-z
Kevin S, Martha M, Emily S, Heather R-G (2018) The economic benefits of the U.S. Polyurethane Industry
Khabarov YG, Kuzyakov NY, Veshnyakov VA et al (2016) Nitration of sulfate lignin under homogeneous conditions studied by electron spectroscopy. Russ Chem Bull 65:2925–2931. https://doi.org/10.1007/s11172-016-1679-2
Kim JY, Lee JH, Park J et al (2015) Catalytic pyrolysis of lignin over HZSM-5 catalysts: effect of various parameters on the production of aromatic hydrocarbon. J Anal Appl Pyrolysis 114:273–280. https://doi.org/10.1016/j.jaap.2015.06.007
Kleinert M, Barth T (2008) Phenols from lignin. Chem Eng Technol 31:736–745. https://doi.org/10.1002/ceat.200800073
Koh SCL, Maguire S, Koh SCL, Maguire S (2011) WTE-Technology. In: Rogoff MJ, Screve F (eds) Waste-to-energy: technologies and project implementation. Second, IGI Global, pp 266–284
Lambertz C, Ece S, Fischer R, Commandeur U (2016) Progress and obstacles in the production and application of recombinant lignin-degrading peroxidases. Bioengineered 7:145–154. https://doi.org/10.1080/21655979.2016.1191705
Laurichesse S, Avérous L (2014) chemical modification of lignins: towards biobased polymers. Prog Polym Sci 39:1266–1290. https://doi.org/10.1016/j.progpolymsci.2013.11.004
Lee A, Deng Y (2015) Green polyurethane from lignin and soybean oil through non-isocyanate reactions. Eur Polym J 63:67–73. https://doi.org/10.1016/j.eurpolymj.2014.11.023
Lee Y, Park CH, Lee EY (2017) Chemical modification of methanol-insoluble kraft lignin using oxypropylation under mild conditions for the preparation of bio-polyester. J Wood Chem Technol 37:334–342. https://doi.org/10.1080/02773813.2017.1303512
Lei H, Ren S, Julson J (2009) The effects of reaction temperature and time and particle size of corn stover on microwave pyrolysis. Energy Fuels 23:3254–3261. https://doi.org/10.1021/ef9000264
Liu Y, Li K (2006) Preparation and characterization of demethylated lignin-polyethylenimine adhesives. J Adhes 82:593–605. https://doi.org/10.1080/00218460600766632
Liu Q, Li P, Liu N, Shen D (2017) Lignin depolymerization to aromatic monomers and oligomers in isopropanol assisted by microwave heating. Polym Degrad Stab 135:54–60. https://doi.org/10.1016/j.polymdegradstab.2016.11.016
Lu Y, Jin H, Zhang R (2019) Evaluation of stability and catalytic activity of Ni catalysts for hydrogen production by biomass gasification in supercritical water. Carbon Resour Convers 2:95–101. https://doi.org/10.1016/j.crcon.2019.03.001
Luo S, Cao J, McDonald AG (2017) Esterification of industrial lignin and its effect on the resulting poly(3-hydroxybutyrate-co-3-hydroxyvalerate) or polypropylene blends. Ind Crops Prod 97:281–291. https://doi.org/10.1016/j.indcrop.2016.12.024
Luo S, Cao J, McDonald AG (2018a) Cross-linking of technical lignin via esterification and thermally initiated free radical reaction. Ind Crops Prod 121:169–179. https://doi.org/10.1016/J.INDCROP.2018.05.007
Luo X, Xiao Y, Wu Q, Zeng J (2018b) Development of high-performance biodegradable rigid polyurethane foams using all bioresource-based polyols: lignin and soy oil-derived polyols. Int J Biol Macromol 115:786–791. https://doi.org/10.1016/j.ijbiomac.2018.04.126
Luong ND, Binh NTT, Duong LD et al (2012) An eco-friendly and efficient route of lignin extraction from black liquor and a lignin-based copolyester synthesis. Polym Bull 68:879–890. https://doi.org/10.1007/s00289-011-0658-x
Ma R, Guo M, Zhang X (2014) Selective conversion of biorefinery lignin into dicarboxylic acids. Chemsuschem 7:412–415. https://doi.org/10.1002/cssc.201300964
Mai C, Elder T (2016) Wood: chemically modified. Ref Modul Mater Sci Mater Eng 1–6. https://doi.org/10.1016/B978-0-12-803581-8.03537-2
Mandal SC, Mandal V, Das AK (2015) Classification of extraction methods. In: Mandal SC, Mandal V, Das AK (eds) Essentials of botanical extraction. Academic Press, pp 83–136
Marcus Y (2016a) Low-melting ionic salts. Ionic liquid properties. Springer, Cham, Switzerland, pp 109–122
Marcus Y (2016b) Room temperature ionic liquids. Ionic liquid properties. Springer, Cham, Switzerland, pp 123–220
MartÃnez-Palou R (2010) Microwave-assisted synthesis using ionic liquids. Mol Divers 14:3–25. https://doi.org/10.1007/s11030-009-9159-3
Mašek O (2016) Biochar in thermal and thermochemical biorefineries-production of biochar as a coproduct. In: Luque R, Lin CSK, Wilson K, Clark JH (eds) Handbook of biofuels production: processes and technologies, 2nd edn. Woodhead Publishing, pp 655–671
Matsushita Y (2015) Conversion of technical lignins to functional materials with retained polymeric properties. J Wood Sci 61:230–250. https://doi.org/10.1007/s10086-015-1470-2
Matsushita Y, Yasuda S (2003) Reactivity of a condensed-type lignin model compound in the Mannich reaction and preparation of cationic surfactant from sulfuric acid lignin. J Wood Sci 49:166–171. https://doi.org/10.1007/s100860300026
Hong Y, Dashtban M, Chen S, Song R, Qin W (2015) Lignin in paper mill sludge is degraded by white-rot fungi in submerged fermentation. J Microb Biochem Technol 7:177–181. https://doi.org/10.4172/1948-5948.1000201
Meister JJ (2002) MODIFICATION OF LIGNIN*. J Macromol Sci Part C Polym Rev 42:235–289. https://doi.org/10.1081/MC-120004764
Miller JE, Evans L, Littlewolf A, Trudell DE (1999) Batch microreactor studies of lignin and lignin model compound depolymerization by bases in alcohol solvents. Fuel 78:1363–1366. https://doi.org/10.1016/S0016-2361(99)00072-1
Miller J, Evans L, Mudd JE, Brown KA (2002) Batch microreactor studies of lignin depolymerization by bases. 2. Aqueous Solvents. Sandia Natl Rep 1–52. https://doi.org/10.2172/800964
Mishra G, Saka S (2013) Effects of water in water/phenol mixtures on liquefaction of Japanese beech as treated under subcritical conditions. Holzforschung 67:241–247. https://doi.org/10.1515/hf-2012-0050
Mohanty AK, Misra M, Drzal LT (2005) Natural fibers, biopolymers, and biocomposites. Taylor & Francis
Mullen CA, Boateng AA (2010) Catalytic pyrolysis-GC/MS of lignin from several sources. Fuel Process Technol 91:1446–1458. https://doi.org/10.1016/j.fuproc.2010.05.022
Nikafshar S, Zabihi O, Moradi Y et al (2017) Catalyzed synthesis and characterization of a novel lignin-based curing agent for the curing of high-performance epoxy resin. Polymers (Basel) 9:1–16. https://doi.org/10.3390/polym9070266
Onwudili JA, Williams PT (2014) Catalytic depolymerization of alkali lignin in subcritical water: influence of formic acid and Pd/C catalyst on the yields of liquid monomeric aromatic products. Green Chem 16:4740–4748. https://doi.org/10.1039/C4GC00854E
Osada M, Sato T, Watanabe M et al (2004) Low-temperature catalytic gasification of lignin and cellulose with a ruthenium catalyst in supercritical water. Energy Fuels 18:327–333. https://doi.org/10.1021/ef034026y
Osada M, Sato O, Watanabe M et al (2006) Water density effect on lignin gasification over supported noble metal catalysts in supercritical water. Energy Fuels 20:930–935. https://doi.org/10.1021/ef050398q
Ouyang X, Ke L, Qiu X et al (2009) Sulfonation of alkali lignin and its potential use in dispersant for cement. J Dispers Sci Technol 30:1–6. https://doi.org/10.1080/01932690802473560
Oveissi F, Fatehi P (2015) Characterization of four different lignins as a first step toward the identification of suitable end-use applications. J Appl Polym Sci 132:42336. https://doi.org/10.1002/app.42336
Pan X, Saddler JN (2013) Effect of replacing polyol by organosolv and kraft lignin on the property and structure of rigid polyurethane foam. Biotechnol Biofuels 6:12. https://doi.org/10.1186/1754-6834-6-12
Pan J, Fu J, Deng S, Lu X (2014) microwave-assisted degradation of lignin model compounds in imidazolium-based ionic liquids. Energy Fuels 28:1380–1386. https://doi.org/10.1021/ef402062w
Pandey MP, Kim CS (2011) Lignin depolymerization and conversion: a review of thermochemical methods. Chem Eng Technol 34:29–41. https://doi.org/10.1002/ceat.201000270
Park J, Riaz A, Insyani R, Kim J (2018) Understanding the relationship between the structure and depolymerization behavior of lignin. Fuel 217:202–210. https://doi.org/10.1016/j.fuel.2017.12.079
Park I-K, Sun H, Kim S-H et al (2019) Solvent-free bulk polymerization of lignin-polycaprolactone (PCL) copolymer and its thermoplastic characteristics. Sci Rep 9:7033. https://doi.org/10.1038/s41598-019-43296-2
Podschun J, Saake B, Lehnen R (2015) Reactivity enhancement of organosolv lignin by phenolation for improved bio-based thermosets. Eur Polym J 67:1–11. https://doi.org/10.1016/j.eurpolymj.2015.03.029
Pohjanlehto H, Setälä HM, Kiely DE, McDonald AG (2014) Lignin-xylaric acid-polyurethane-based polymer network systems: preparation and characterization. J Appl Polym Sci 131:39714. https://doi.org/10.1002/app.39714
Rachel-Tang DY, Islam A, Taufiq-Yap YH (2017) Bio-oil production via catalytic solvolysis of biomass. RSC Adv 7:7820–7830. https://doi.org/10.1039/c6ra27824h
Rajasekhar Reddy B, Vinu R (2018) Microwave-assisted co-pyrolysis of high ash Indian coal and rice husk: product characterization and evidence of interactions. Fuel Process Technol 178:41–52. https://doi.org/10.1016/j.fuproc.2018.04.018
Ranzi E, Debiagi PEA, Frassoldati A (2017) Mathematical modeling of fast biomass pyrolysis and bio-oil formation. Note I: kinetic mechanism of biomass pyrolysis. ACS Sustain Chem Eng 5:2867–2881. https://doi.org/10.1021/acssuschemeng.6b03096
Rezzoug S-A, Capart R (2002) Liquefaction of wood in two successive steps: solvolysis in ethylene-glycol and catalytic hydrotreatment. Appl Energy 72:631–644. https://doi.org/10.1016/S0306-2619(02)00054-5
Cetin NS, Özmen N (2002) Use of organosolv lignin in phenol-formaldehyde resins for particleboard production: II. Particleboard production and properties. Int J Adhes Adhes 22:481–486. https://doi.org/10.1016/S0143-7496(02)00059-3
Rodriguez Correa C, Kruse A (2018) Supercritical water gasification of biomass for hydrogen production—review. J Supercrit Fluids 133:573–590
Rogers RD, Voth GA (2007) Ionic liquids. Accounsts Chem Res 40:1077–1078
Sáenz-Pérez M, Lizundia E, Laza JM et al (2016) Methylene diphenyl diisocyanate (MDI) and toluene diisocyanate (TDI) based polyurethanes: thermal, shape-memory and mechanical behavior. RSC Adv 6:69094–69102. https://doi.org/10.1039/C6RA13492K
Sainsbury PD, Hardiman EM, Ahmad M et al (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. https://doi.org/10.1021/cb400505a
Saito T, Perkins JH, Jackson DC et al (2013) Development of lignin-based polyurethane thermoplastics. RSC Adv 3:21832–21840. https://doi.org/10.1039/c3ra44794d
Salvachúa D, Karp EM, Nimlos CT et al (2015) Towards lignin consolidated bioprocessing: simultaneous lignin depolymerization and product generation by bacteria. Green Chem 17:4951–4967. https://doi.org/10.1039/c5gc01165e
Sanchez-Vazquez SA, Hailes HC, Evans JRG (2013) Hydrophobic polymers from food waste: resources and synthesis. Polym Rev 53:627–694. https://doi.org/10.1080/15583724.2013.834933
Santos JI, MartÃn-sampedro R, Fillat U et al (2015) Evaluating lignin-rich residues from biochemical ethanol production of wheat straw and olive tree pruning by FTIR and 2D-NMR. Int J Polym Sci 2015:1–11. https://doi.org/10.1155/2015/314891
Sato T, Furusawa T, Ishiyama Y et al (2006) Effect of water density on the gasification of lignin with magnesium oxide supported nickel catalysts in supercritical water. Ind Eng Chem Res 45:615–622. https://doi.org/10.1021/ie0510270
Schutyser W, Renders T, Van den Bosch S et al (2018) Chemicals from lignin: an interplay of lignocellulose fractionation, depolymerisation, and upgrading. Chem Soc Rev 47:852–908. https://doi.org/10.1039/C7CS00566K
Shen D, Zhao J, Xiao R, Gu S (2015) Production of aromatic monomers from catalytic pyrolysis of black-liquor lignin. J Anal Appl Pyrolysis 111:47–54. https://doi.org/10.1016/j.jaap.2014.12.013
Shi Y, Xia X, Li J et al (2016) Solvolysis kinetics of three components of biomass using polyhydric alcohols as solvents. Bioresour Technol 221:102–110. https://doi.org/10.1016/J.BIORTECH.2016.09.008
Sigoillot JC, Berrin JG, Bey M, et al (2012) Fungal strategies for lignin degradation. In: Advances in botanical research. Academic Press, pp 263–308
Sikarwar VS, Zhao M, Clough P et al (2016) An overview of advances in biomass gasification. Energy Environ Sci 9:2939–2977
Singh SK, Ekhe JD (2014) Solvent effect on HZSM-5 catalyzed solvolytic depolymerization of industrial waste lignin to phenols: superiority of the water–methanol system over methanol. RSC Adv 4:53220–53228. https://doi.org/10.1039/C4RA10240A
Singh SK, Nandeshwar K, Ekhe JD (2016) Thermochemical lignin depolymerization and conversion to aromatics in subcritical methanol: effects of catalytic conditions. New J Chem 40:3677–3685. https://doi.org/10.1039/c5nj02916c
Speight JG (2017) Industrial organic chemistry. Environ Org Chem Eng 87–151. https://doi.org/10.1016/B978-0-12-804492-6.00003-4
Statista (2019) Polyurethane global demand 2022 | Statistic. In: Statista. https://www.statista.com/statistics/747004/polyurethane-demand-worldwide/. Accessed 5 Feb 2020
Suman SK, Dhawaria M, Tripathi D et al (2016) Investigation of lignin biodegradation by Trabulsiella sp. isolated from termite gut. Int Biodeterior Biodegrad 112:12–17. https://doi.org/10.1016/j.ibiod.2016.04.036
Sun Z, Fridrich B, De Santi A et al (2018) Bright side of lignin depolymerization: toward new platform chemicals. Chem Rev 118:614–678. https://doi.org/10.1021/acs.chemrev.7b00588
Tarabanko VE, Petukhov DV, Selyutin GE (2004) New mechanism for the catalytic oxidation of lignin to vanillin. Kinet Catal 45:569–577. https://doi.org/10.1023/B:KICA.0000038087.95130.a5
Tayier M, Duan D, Zhao Y et al (2018) Catalytic effects of various acids on microwave-assisted depolymerization of organosolv lignin. BioResources 13:412–424. https://doi.org/10.15376/biores.13.1.412-424
Thanh Binh NT, Luong ND, Kim DO et al (2009) Synthesis of lignin-based thermoplastic copolyester using kraft lignin as a macromonomer. Compos Interfaces 16:923–935. https://doi.org/10.1163/092764409X12477479344485
Thierry M, Majira A, Pégot B et al (2018) Imidazolium-based ionic liquids as efficient reagents for the C−O bond cleavage of lignin. Chemsuschem 11:439–448. https://doi.org/10.1002/cssc.201701668
Thring RW (1994) Alkaline degradation of Alcell lignin. Biomass Bioenerg 7:125–130. https://doi.org/10.1016/0961-9534(94)00051-T
Todd R, Baroutian S (2017) A techno-economic comparison of subcritical water, supercritical CO2 and organic solvent extraction of bioactives from grape marc. J Clean Prod 158:349–358. https://doi.org/10.1016/J.JCLEPRO.2017.05.043
Toledano A, Serrano L, Labidi J (2012) Organosolv lignin depolymerization with different base catalysts. J Chem Technol Biotechnol 87:1593–1599. https://doi.org/10.1002/jctb.3799
Toledano A, Serrano L, Labidi J (2014) Improving base catalyzed lignin depolymerization by avoiding lignin repolymerization. Fuel 116:617–624. https://doi.org/10.1016/j.fuel.2013.08.071
Upton BM, Kasko AM (2016) Strategies for the conversion of lignin to high-value polymeric materials: review and perspective. Chem Rev 116:2275–2306
Vázquez G, González J, Freire S, Antorrena G (1997) Effect of chemical modification of lignin on the gluebond performance of lignin-phenolic resins. Bioresour Technol 60:191–198. https://doi.org/10.1016/S0960-8524(97)00030-8
Venkatesagowda B (2019) Enzymatic demethylation of lignin for potential biobased polymer applications. Fungal Biol Rev. 33:190–224. https://doi.org/10.1016/j.fbr.2019.06.002
Venkatesagowda B, Dekker RFH (2019) A rapid method to detect and estimate the activity of the enzyme, alcohol oxidase by the use of two chemical complexes—acetylacetone (3,5-diacetyl-1,4-dihydrolutidine) and acetylacetanilide (3,5-di-N-phenylacetyl-1,4-dihydrolutidine). J Microbiol Methods 158:71–79. https://doi.org/10.1016/j.mimet.2019.01.021
Vithanage AE, Chowdhury E, Alejo LD et al (2017) Renewably sourced phenolic resins from lignin bio-oil. J Appl Polym Sci 134:44827. https://doi.org/10.1002/app.44827
Wang H, Sun X, Seib P (2001) Strengthening blends of poly (lactic acid) and starch with methylenediphenyl diisocyanate. J Appl Polym Sci 82:1761–1767. https://doi.org/10.1002/app.2018
Wang L, Lei H, Ren S et al (2012) Aromatics and phenols from catalytic pyrolysis of Douglas fir pellets in microwave with ZSM-5 as a catalyst. J Anal Appl Pyrolysis 98:194–200. https://doi.org/10.1016/j.jaap.2012.08.002
Wang H, Tucker M, Ji Y (2013) Recent development in chemical depolymerization of lignin: a review. J Appl Chem 2013:1–9. https://doi.org/10.1155/2013/838645
Wang B, Chen TY, Wang HM et al (2018) Amination of biorefinery technical lignins using Mannich reaction synergy with subcritical ethanol depolymerization. Int J Biol Macromol 107:426–435. https://doi.org/10.1016/j.ijbiomac.2017.09.012
Wasserscheid P (2003) Potential to apply ionic liquids in industry. In: Rogers RD, Seddon KR, Volkov S (eds) Green industrial applications of ionic liquids. Springer, Dordrecht, Dordrecht, pp 29–47
Watanabe M, Inomata H, Osada M et al (2003) Catalytic effects of NaOH and ZrO2 for partial oxidative gasification of n-hexadecane and lignin in supercritical water. Fuel 82:545–552. https://doi.org/10.1016/S0016-2361(02)00320-4
Wendisch VF, Kim Y, Lee J-H (2018) Chemicals from lignin: recent depolymerization techniques and upgrading extended pathways. Curr Opin Green Sustain Chem.14:33–39. https://doi.org/10.1016/j.cogsc.2018.05.006
Wikberg H, Ohra-aho T, Leppävuori J, Liitiä T, Kanerva H (2018) Method for producing reactive lignin. WO 2018/115592 A1, Teknologian Tutkimuskeskus Vtt OY
Wu Y-R, He J (2013) Characterization of anaerobic consortia coupled lignin depolymerization with biomethane generation. Bioresour Technol 139:5–12. https://doi.org/10.1016/J.BIORTECH.2013.03.103
Xiao W, Han L, Zhao Y (2011) Comparative study of conventional and microwave-assisted liquefaction of corn stover in ethylene glycol. Ind Crops Prod 34:1602–1606. https://doi.org/10.1016/j.indcrop.2011.05.024
Xie J, Qi J, Hse C, Shupe TF (2015) Optimization for microwave-assisted direct liquefaction of bamboo residue in glycerol/methanol mixtures. J For Res 26:261–265. https://doi.org/10.1007/s11676-015-0032-1
Xu C, Ferdosian F (2017) Conversion of lignin into bio-based chemicals and materials. Springer, Germany
Xu J, Jiang J, Hse C, Shupe TF (2012) Renewable chemical feedstocks from integrated liquefaction processing of lignocellulosic materials using microwave energy. Green Chem 14:2821–2830. https://doi.org/10.1039/c2gc35805k
Xu R, Zhang K, Liu P et al (2018) Lignin depolymerization and utilization by bacteria. Bioresour Technol 269:557–566. https://doi.org/10.1016/j.biortech.2018.08.118
Yamaguchi A, Hiyoshi N, Sato O et al (2008) Lignin gasification over supported ruthenium trivalent salts in supercritical water. Energy Fuels 22:1485–1492. https://doi.org/10.1021/ef8001263
Yamaguchi A, Hiyoshi N, Sato O, Shirai M (2012) Gasification of organosolv-lignin over charcoal supported noble metal salt catalysts in supercritical water. Top Catal 55:889–896. https://doi.org/10.1007/s11244-012-9857-4
Yang Y, Fan H, Meng Q et al (2017) Ionic liquid [OMIm][OAc] directly inducing oxidation cleavage of the β-O-4 bond of lignin model compounds. Chem Commun 53:8850–8853. https://doi.org/10.1039/c7cc04209d
Yerrayya A, Suriapparao DV, Natarajan U, Vinu R (2018) Selective production of phenols from lignin via microwave pyrolysis using different carbonaceous susceptors. Bioresour Technol 270:519–528. https://doi.org/10.1016/j.biortech.2018.09.051
Yin G, Jin F, Yao G, Jing Z (2015) Hydrothermal conversion of catechol into four-carbon dicarboxylic acids. Ind Eng Chem Res 54:68–75. https://doi.org/10.1021/ie5036447
Yu Y, Li X, Su L et al (2012) The role of shape selectivity in catalytic fast pyrolysis of lignin with zeolite catalysts. Appl Catal A Gen 447–448:115–123. https://doi.org/10.1016/j.apcata.2012.09.012
Yue X, Chen F, Zhou X (2011) Improved interfacial bonding of pvc/wood-flour composites by lignin amine modification. BioResources 6:2022–2034. https://doi.org/10.15376/biores.6.2.2022-2044
Yunpu W, Leilei D, Liangliang F et al (2016) Review of microwave-assisted lignin conversion for renewable fuels and chemicals. J Anal Appl Pyrolysis 119:104–113. https://doi.org/10.1016/j.jaap.2016.03.011
Zhang L, Huang J (2001) Effects of nitrolignin on mechanical properties of polyurethane-nitrolignin films. J Appl Polym Sci 80:1213–1219. https://doi.org/10.1002/app.1206
Zhang S, Dong Q, Zhang L, Xiong Y (2015a) High quality syngas production from microwave pyrolysis of rice husk with char-supported metallic catalysts. Bioresour Technol 191:17–23. https://doi.org/10.1016/J.BIORTECH.2015.04.114
Zhang Z, Macquarrie DJ, De Bruyn M et al (2015b) Low-temperature microwave-assisted pyrolysis of waste office paper and the application of bio-oil as an Al adhesive. Green Chem 17:260–270. https://doi.org/10.1039/c4gc00768a
Zheng A, Zhao Z, Chang S et al (2014) Effect of crystal size of ZSM-5 on the aromatic yield and selectivity from catalytic fast pyrolysis of biomass. J Mol Catal A: Chem 383–384:23–30. https://doi.org/10.1016/j.molcata.2013.11.005
Zhi Z, Wang H (2014) White-rot fungal pretreatment of wheat straw with Phanerochaete chrysosporium for biohydrogen production: Simultaneous saccharification and fermentation. Bioprocess Biosyst Eng 37:1447–1458. https://doi.org/10.1007/s00449-013-1117-x
Zhou S, Garcia-Perez M, Pecha B et al (2013) Effect of the fast pyrolysis temperature on the primary and secondary products of lignin. Energy Fuels 27:5867–5877. https://doi.org/10.1021/ef4001677
Zhu X, Peng C, Chen H et al (2018) Opportunities of ionic liquids for lignin utilization from biorefinery. ChemistrySelect 3:7945–7962. https://doi.org/10.1002/slct.201801393
Zou L, Ross BM, Hutchison LJ et al (2015) Fungal demethylation of kraft lignin. Enzyme Microb Technol 73–74:44–50. https://doi.org/10.1016/J.ENZMICTEC.2015.04.001
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This book chapter was possible thanks to the financial support received from the National Council of Science and Technology (CONACyT, Mexico).
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Lopez-Camas, K., Arshad, M., Ullah, A. (2020). Chemical Modification of Lignin by Polymerization and Depolymerization. In: Sharma, S., Kumar, A. (eds) Lignin. Springer Series on Polymer and Composite Materials. Springer, Cham. https://doi.org/10.1007/978-3-030-40663-9_5
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