Abstract
Increasing energy demand and depleting non-renewable energy resources have centred the researcher’s cognition to develop a sustainable technology that can exploit renewable energies. Renewable energies include solar energy, wind energy, tidal energy, hydropower, biomass but leaving a snag there that only biomass, as the renewable energy resource, could be the sustainable alternative for transportation fuels because it delivers sustainable carbon. Biomass comprises of three main units, i.e. cellulose, hemicellulose, and lignin. In the recent past, cellulose and hemicellulose have acquired much attention but, on the other hand, lignin scuffled to get proper consideration. However, earlier it has been used to produce a less effective heat and electricity by combustion. Currently, lignin is magnanimous amongst researchers because of its higher energy density, great source for phenolic fine chemicals, etc. Bio-oils derived from fast pyrolysis of lignocellulosic biomass comprise of more than 300 oxy-compounds which vitiate its quality in the form of low pH value, less stable, highly viscous, and low heating value for the application as transportation fuel. Therefore, it needs the proper upgradation technology to make it exploitable for transportation fuels. Here in this chapter, a succinct review is carried out for the lignin-derived bio-oil model compounds such as phenol, guaiacol, anisole, vanillin, and eugenol. Guaiacol component is one of the key components in phenolic fraction of bio-oil because its presence in bio-oil is often higher and, in addition, other higher molecular weight phenolic model compounds such as vanillin and eugenol reduce to guaiacol majorly. Furthermore, guaiacol component can successfully represent a higher fraction of lignin structure because of attachment of hydroxyl and methoxy groups in its molecular structure.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Abbreviations
- PHE:
-
Phenol
- BEN:
-
Benzene
- CYHA:
-
Cyclohexane
- CYHN:
-
Cyclohexanone
- CYHL:
-
Cyclohexanol
- CYHD:
-
Cyclohexan-2,4-dione
- ANI:
-
Anisole
- o-Cr:
-
o-cresol
- m-Cr:
-
m-cresol
- p-Cr:
-
p-cresol
- TOL:
-
Toluene
- MXCYHA:
-
Methoxycyclohexane
- GUA:
-
Guaiacol
- CAT:
-
Catechol
- MXCYHL:
-
2-methoxycyclohexanol
- MCAT:
-
Methylcatechol
- SAL:
-
Salicylaldehyde
- MXCYHDL:
-
6-methoxycyclohexa-1,5-dien-1-ol
- CYHDN:
-
Cyclohexan-1,2-dione
- CYHDDL:
-
Cyclohexa-2,6-dien-1,2-diol
- CYPTN:
-
Cyclopentanone
- DHBZD:
-
3,4-dihydroxybenzaldehyde
- VAN:
-
Vanillin
- p-HBZD:
-
4-hydroxybenzaldehyde
- MXBZD:
-
3-methoxybenzaldehyde
- m-HBZD:
-
3-hydroxybenzaldehyde
- EUG:
-
Eugenol
- ALCAT:
-
4-allylcatechol
- ALPHE:
-
4-allylphenol
- PLPHE:
-
4-propylphenol
- PLBEN:
-
Propylbenzene
- PLGUA:
-
4-propylguaiacol
- PLCAT:
-
4-propylcatechol
- ALANI:
-
3-allylanisole
- ALPHE:
-
3-allylphenol
References
Huber GW, Iborra S, Corma A (2006) Synthesis of transportation fuels from biomass: chemistry, catalysts, and engineering. Chem Rev 106:4044–4098
Wang Y, He T, Liu K, Wu J, Fang Y (2012) From biomass to advanced bio-fuel by catalytic pyrolysis/hydro-processing: hydrodeoxygenation of bio-oil derived from biomass catalytic pyrolysis. Bioresour Technol 108:280–284
Saidi M, Samimi F, Karimipourfard D, Nimmanwudipong T, Gates BC, Rahimpour MR (2014) Upgrading of lignin-derived bio-oils by catalytic hydrodeoxygenation. Energy Environ Sci 7:103–129
Klass DL (2004) Biomass for renewable energy and fuels. Encycl Energy 1:193–212
Alonso DM, Bond JQ, Dumesic JA (2010) Catalytic conversion of biomass to biofuels. Green Chem 12:1493–1513
Alonso DM, Wettstein SG, Dumesic JA (2012) Bimetallic catalysts for upgrading of biomass to fuels and chemicals. Chem Soc Rev 41:8075
Stöcker M (2008) Biofuels and biomass-to-liquid fuels in the biorefinery: catalytic conversion of lignocellulosic biomass using porous materials. Angew Chemie Int Ed 47:9200–9211
Mu W, Ben H, Ragauskas A, Deng Y (2013) Lignin pyrolysis components and upgrading—technology review. BioEnergy Res 6:1183–1204
Pandey MP, Kim CS (2011) Lignin depolymerization and conversion: a review of thermochemical methods. Chem Eng Technol 34:29–41
Kanaujia PK, Sharma YK, Garg MO, Tripathi D, Singh R (2014) Review of analytical strategies in the production and upgrading of bio-oils derived from lignocellulosic biomass. J Anal Appl Pyrolysis 105:55–74
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. Catal Today 156:8–22
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
Azadi P, Inderwildi OR, Farnood R, King DA (2013) Liquid fuels, hydrogen and chemicals from lignin: a critical review. Renew Sustain Energy Rev 21:506–523
Jiang G, Nowakowski DJ, Bridgwater AV (2010) Effect of the temperature on the composition of lignin pyrolysis products. Energy Fuels 24:4470–4475
Corma A (2003) State of the art and future challenges of zeolites as catalysts. J Catal 216:298–312
Furimsky E (1983) Chemistry of catalytic hydrodeoxygenation. Catal Rev 25:421–458
Furimsky E (2000) Catalytic hydrodeoxygenation. Appl Catal A Gen 199:147–190
Şenol Oİ, Ryymin E-M, Viljava T-R, Krause AOI (2007) Effect of hydrogen sulphide on the hydrodeoxygenation of aromatic and aliphatic oxygenates on sulphided catalysts. J Mol Catal A Chem 277:107–112
Shin EJ, Keane MA (2000) Gas-phase hydrogenation/hydrogenolysis of phenol over supported nickel catalysts. Ind Eng Chem Res 39:883–892
Zhao C, Lercher JA (2012) Selective hydrodeoxygenation of lignin-derived phenolic monomers and dimers to cycloalkanes on Pd/C and HZSM-5 catalysts. ChemCatChem 4:64–68
Hong D-Y, Miller SJ, Agrawal PK, Jones CW (2010) Hydrodeoxygenation and coupling of aqueous phenolics over bifunctional zeolite-supported metal catalysts. Chem Commun 46:1038–1040
Verma AM, Kishore N (2016) DFT analyses of reaction pathways and temperature effects on various guaiacol conversion reactions in gas phase environment. ChemistrySelect 1:6196–6205
Zhu X, Lobban LL, Mallinson RG, Resasco DE (2011) Bifunctional transalkylation and hydrodeoxygenation of anisole over a Pt/HBeta catalyst. J Catal 281:21–29
Hurff SJ, Klein MT (1983) Reaction pathway analysis of thermal and catalytic lignin fragmentation by use of model compounds. Ind Eng Chem Fundam 22:426–430
Li K, Wang R, Chen J (2011) Hydrodeoxygenation of anisole over silica-supported Ni2P, MoP, and NiMoP catalysts. Energy Fuels 25:854–863
Huuska MK (1986) Effect of catalyst composition on the hydrogenolysis of anisole. Polyhedron 5:233–236
Huuska M, Rintala J (1985) Effect of catalyst acidity on the hydrogenolysis of anisole. J Catal 94:230–238
Olcese RN, Bettahar M, Petitjean D, Malaman B, Giovanella F, Dufour A (2012) Gas-phase hydrodeoxygenation of guaiacol over Fe/SiO2 catalyst. Appl Catal B Environ 115–116:63–73
Gao D, Xiao Y, Varma A (2015) Guaiacol hydrodeoxygenation over platinum catalyst: reaction pathways and kinetics. Ind Eng Chem Res 54:10638–10644
Elliott DC, Hart TR (2009) Catalytic hydroprocessing of chemical models for bio-oil. Energy Fuels 23:631–637
Bykova MV, Ermakov DY, Kaichev VV, Bulavchenko OA, Saraev AA, Lebedev MY, Yakovlev V (2012) Ni-based sol-gel catalysts as promising systems for crude bio-oil upgrading: guaiacol hydrodeoxygenation study. Appl Catal B Environ 113–114:296–307
Bui VN, Laurenti D, Afanasiev P, Geantet C (2011) Hydrodeoxygenation of guaiacol with CoMo catalysts. Part I: promoting effect of cobalt on HDO selectivity and activity. Appl Catal B Environ 101:239–245
Lee K, Gu GH, Mullen C, Boateng A, Vlachos DG (2015) Guaiacol hydrodeoxygenation mechanism on Pt(111): insights from density functional theory and linear free energy relations. ChemSuschem 8:315–322
Lu J, Behtash S, Mamun O, Heyden A (2015) Theoretical investigation of the reaction mechanism of the guaiacol hydrogenation over a Pt(111) catalyst. ACS Catal 5:2423–2435
Chiu C, Genest A, Borgna A, Rösch N (2014) Hydrodeoxygenation of guaiacol over Ru(0001): a DFT study. ACS Catal 4:4178–4188
Lu J, Behtash S, Mamun O, Heyden A (2015) Theoretical investigation of the reaction mechanism of the hydrodeoxygenation of guaiacol over a Ru(0001) model surface. J Catal 321:39–50
Bindwal AB, Vaidya PD (2014) Reaction kinetics of vanillin hydrogenation in aqueous solutions using a Ru/C catalyst. Energy Fuels 28:3357–3362
Verma AM, Kishore N (2017) Molecular modelling approach to elucidate the thermal decomposition routes of vanillin. New J Chem 41:8845–8859
Peng J, Chen P, Lou H, Zheng X (2008) Upgrading of bio-oil over aluminum silicate in supercritical ethanol. Energy Fuels 22:3489–3492
Shen DK, Gu S, Luo KH, Wang SR, Fang MX (2010) The pyrolytic degradation of wood-derived lignin from pulping process. Bioresour Technol 101:6136–6146
Walton NJ, Mayer MJ, Narbad A (2003) Vanillin. Phytochemistry 63:505–515
Jiang H, Yu X, Peng X, Zhang H, Nie R, Lu X, Zhou D, Xia Q (2016) Efficient aqueous hydrodeoxygenation of vanillin over a mesoporous carbon nitride-modified Pd nanocatalyst. RSC Adv 6:69045–69051
Shin EJ, Nimlos MR, Evans RJ (2001) A study of the mechanisms of vanillin pyrolysis by mass spectrometry and multivariate analysis. Fuel 80:1689–1696
Liu C, Deng Y, Wu S, Mou H, Liang J, Lei M (2016) Study on the pyrolysis mechanism of three guaiacyl-type lignin monomeric model compounds. J Anal Appl Pyrolysis 118:123–129
Horáček J, Šťávová G, Kelbichová V, Kubička D (2013) Zeolite-Beta-supported platinum catalysts for hydrogenation/hydrodeoxygenation of pyrolysis oil model compounds. Catal Today 204:38–45
Nimmanwudipong T, Runnebaum RC, Ebeler SE, Block DE, Gates BC (2012) Upgrading of lignin-derived compounds: reactions of eugenol catalyzed by HY zeolite and by Pt/γ-Al2O3. Catal Lett 142:151–160
Zhang C, Xing J, Song L, Xin H, Lin S, Xing L, Li X (2014) Aqueous-phase hydrodeoxygenation of lignin monomer eugenol: influence of Si/Al ratio of HZSM-5 on catalytic performances. Catal Today 234:145–152
Verma AM, Kishore N (2017) Gas phase conversion of eugenol into various hydrocarbons and platform chemicals. RSC Adv 7:2527–2543
Nowakowski DJ, Bridgwater AV, Elliott DC, Meier D, de Wild P (2010) Lignin fast pyrolysis: results from an international collaboration. J Anal Appl Pyrolysis 88:53–72
Chen M-Y, Huang Y-B, Pang H, Liu X-X, Fu Y (2015) Hydrodeoxygenation of lignin-derived phenols into alkanes over carbon nanotube supported Ru catalysts in biphasic systems. Green Chem 17:1710–1717
Deepa AK, Dhepe PL (2014) Function of metals and supports on the hydrodeoxygenation of phenolic compounds. ChemPlusChem 79:1573–1583
Ledesma EB, Hoang JN, Nguyen Q, Hernandez V, Nguyen MP, Batamo S, Fortune CK (2013) Unimolecular decomposition pathway for the vapor-phase cracking of eugenol, a biomass tar compound. Energy Fuels 27:6839–6846
Dutta S, Wu KC-W, Saha B (2014) Emerging strategies for breaking the 3D amorphous network of lignin. Catal Sci Technol 4:3785–3799
Wang H, Male J, Wang Y (2013) Recent advances in hydrotreating of pyrolysis bio-oil and its oxygen-containing model compounds. ACS Catal 3:1047–1070
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2018 Springer Nature Singapore Pte Ltd.
About this chapter
Cite this chapter
Verma, A.M., Kishore, N. (2018). A Succinct Review on Upgrading of Lignin-Derived Bio-oil Model Components. In: De, S., Bandyopadhyay, S., Assadi, M., Mukherjee, D. (eds) Sustainable Energy Technology and Policies. Green Energy and Technology. Springer, Singapore. https://doi.org/10.1007/978-981-10-7188-1_14
Download citation
DOI: https://doi.org/10.1007/978-981-10-7188-1_14
Published:
Publisher Name: Springer, Singapore
Print ISBN: 978-981-10-7187-4
Online ISBN: 978-981-10-7188-1
eBook Packages: EnergyEnergy (R0)