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A Succinct Review on Upgrading of Lignin-Derived Bio-oil Model Components

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Sustainable Energy Technology and Policies

Part of the book series: Green Energy and Technology ((GREEN))

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.

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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

  1. Huber GW, Iborra S, Corma A (2006) Synthesis of transportation fuels from biomass: chemistry, catalysts, and engineering. Chem Rev 106:4044–4098

    Article  Google Scholar 

  2. 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

    Article  Google Scholar 

  3. 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

    Article  Google Scholar 

  4. Klass DL (2004) Biomass for renewable energy and fuels. Encycl Energy 1:193–212

    Google Scholar 

  5. Alonso DM, Bond JQ, Dumesic JA (2010) Catalytic conversion of biomass to biofuels. Green Chem 12:1493–1513

    Article  Google Scholar 

  6. Alonso DM, Wettstein SG, Dumesic JA (2012) Bimetallic catalysts for upgrading of biomass to fuels and chemicals. Chem Soc Rev 41:8075

    Article  Google Scholar 

  7. 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

    Article  Google Scholar 

  8. Mu W, Ben H, Ragauskas A, Deng Y (2013) Lignin pyrolysis components and upgrading—technology review. BioEnergy Res 6:1183–1204

    Article  Google Scholar 

  9. Pandey MP, Kim CS (2011) Lignin depolymerization and conversion: a review of thermochemical methods. Chem Eng Technol 34:29–41

    Article  Google Scholar 

  10. 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

    Article  Google Scholar 

  11. 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

    Article  Google Scholar 

  12. 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

    Article  Google Scholar 

  13. 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

    Article  Google Scholar 

  14. Jiang G, Nowakowski DJ, Bridgwater AV (2010) Effect of the temperature on the composition of lignin pyrolysis products. Energy Fuels 24:4470–4475

    Article  Google Scholar 

  15. Corma A (2003) State of the art and future challenges of zeolites as catalysts. J Catal 216:298–312

    Article  Google Scholar 

  16. Furimsky E (1983) Chemistry of catalytic hydrodeoxygenation. Catal Rev 25:421–458

    Article  Google Scholar 

  17. Furimsky E (2000) Catalytic hydrodeoxygenation. Appl Catal A Gen 199:147–190

    Article  Google Scholar 

  18. 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

    Article  Google Scholar 

  19. Shin EJ, Keane MA (2000) Gas-phase hydrogenation/hydrogenolysis of phenol over supported nickel catalysts. Ind Eng Chem Res 39:883–892

    Article  Google Scholar 

  20. 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

    Article  Google Scholar 

  21. 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

    Article  Google Scholar 

  22. 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

    Article  Google Scholar 

  23. 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

    Article  Google Scholar 

  24. 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

    Article  Google Scholar 

  25. Li K, Wang R, Chen J (2011) Hydrodeoxygenation of anisole over silica-supported Ni2P, MoP, and NiMoP catalysts. Energy Fuels 25:854–863

    Article  Google Scholar 

  26. Huuska MK (1986) Effect of catalyst composition on the hydrogenolysis of anisole. Polyhedron 5:233–236

    Article  Google Scholar 

  27. Huuska M, Rintala J (1985) Effect of catalyst acidity on the hydrogenolysis of anisole. J Catal 94:230–238

    Article  Google Scholar 

  28. 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

    Article  Google Scholar 

  29. Gao D, Xiao Y, Varma A (2015) Guaiacol hydrodeoxygenation over platinum catalyst: reaction pathways and kinetics. Ind Eng Chem Res 54:10638–10644

    Article  Google Scholar 

  30. Elliott DC, Hart TR (2009) Catalytic hydroprocessing of chemical models for bio-oil. Energy Fuels 23:631–637

    Article  Google Scholar 

  31. 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

    Article  Google Scholar 

  32. 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

    Article  Google Scholar 

  33. 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

    Article  Google Scholar 

  34. 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

    Article  Google Scholar 

  35. Chiu C, Genest A, Borgna A, Rösch N (2014) Hydrodeoxygenation of guaiacol over Ru(0001): a DFT study. ACS Catal 4:4178–4188

    Article  Google Scholar 

  36. 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

    Article  Google Scholar 

  37. Bindwal AB, Vaidya PD (2014) Reaction kinetics of vanillin hydrogenation in aqueous solutions using a Ru/C catalyst. Energy Fuels 28:3357–3362

    Article  Google Scholar 

  38. Verma AM, Kishore N (2017) Molecular modelling approach to elucidate the thermal decomposition routes of vanillin. New J Chem 41:8845–8859

    Article  Google Scholar 

  39. Peng J, Chen P, Lou H, Zheng X (2008) Upgrading of bio-oil over aluminum silicate in supercritical ethanol. Energy Fuels 22:3489–3492

    Article  Google Scholar 

  40. 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

    Article  Google Scholar 

  41. Walton NJ, Mayer MJ, Narbad A (2003) Vanillin. Phytochemistry 63:505–515

    Article  Google Scholar 

  42. 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

    Article  Google Scholar 

  43. 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

    Article  Google Scholar 

  44. 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

    Article  Google Scholar 

  45. 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

    Article  Google Scholar 

  46. 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

    Article  Google Scholar 

  47. 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

    Article  Google Scholar 

  48. Verma AM, Kishore N (2017) Gas phase conversion of eugenol into various hydrocarbons and platform chemicals. RSC Adv 7:2527–2543

    Article  Google Scholar 

  49. 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

    Article  Google Scholar 

  50. 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

    Article  Google Scholar 

  51. Deepa AK, Dhepe PL (2014) Function of metals and supports on the hydrodeoxygenation of phenolic compounds. ChemPlusChem 79:1573–1583

    Article  Google Scholar 

  52. 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

    Article  Google Scholar 

  53. Dutta S, Wu KC-W, Saha B (2014) Emerging strategies for breaking the 3D amorphous network of lignin. Catal Sci Technol 4:3785–3799

    Article  Google Scholar 

  54. 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

    Article  Google Scholar 

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Correspondence to Nanda Kishore .

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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

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