Abstract
Biomass pyrolysis oil has been reported as a potential renewable biofuel precursor. Although several review articles focusing on lignocellulose pyrolysis can be found, the one that particularly focus on lignin pyrolysis is still not available in literature. Lignin is the second most abundant biomass component and the primary renewable aromatic resource in nature. The pyrolysis chemistry and mechanism of lignin are significantly different from pyrolysis of cellulose or entire biomass. Therefore, different from other review articles in the field, this review particularly focuses on the recent developments in lignin pyrolysis chemistry, mechanism, catalysts, and the upgrading of the bio-oil from lignin pyrolysis. Although bio-oil production from pyrolysis of biomass has been proven on commercial scale and is a very promising option for production of renewable chemicals and fuels, there are still several drawbacks that have not been solved. The components of biomass pyrolysis oils are very complicated and related to the properties of bio-oil. In this review article, the details about pyrolysis oil components particularly those from lignin pyrolysis processes will be discussed first. Due to the poor physical and chemical property, the lignin pyrolysis oil has to be upgraded before usage. The most common method of upgrading bio-oil is hydrotreating. Catalysts have been widely used in petroleum industry for pyrolysis bio-oil upgrading. In this review paper, the mechanism of the hydrodeoxygenation reaction between the model compounds and catalysts will be discussed and the effects of the reaction condition will be summarized.
Similar content being viewed by others
Reference
Perlack RDW, L. L.; Turhollow, A. F.; Graham, R. L.; Stokes, B. J.; Erbach, D. C., (2005). Biomass as Feedstock for a bioenergy and bioproducts Industry: the technical feasibility of a billion-ton annual supply. Technical Report by ORNL, Apr 2005
Administration EI (June 2012) Monthly Energy Review. US Department of Energy
Administration-0384 EI (2011) Annual Energy Review 2010. Department of Energy
Franks JR, Hadingham B (2012) Reducing greenhouse gas emissions from agriculture: avoiding trivial solutions to a global problem. Land Use Policy 29(4):727–736
Iribarren D, Peters JF, Dufour J (2012) Life cycle assessment of transportation fuels from biomass pyrolysis. Fuel 97:812–821
van Oort PAJ, Timmermans BGH, van Swaaij ACPM (2012) Why farmers’ sowing dates hardly change when temperature rises. Eur J Agron 40:102–111
Lenzen M, Schaeffer R (2012) Historical and potential future contributions of power technologies to global warming. Clim Change 112(3):601–632
Biasutti M, Sobel A, Camargo S, Creyts T (2012) Projected changes in the physical climate of the Gulf Coast and Caribbean. Clim Change 112(3):819–845
Climate Change 2007: Synthesis Report (2007). Intergovernmental Panel on Climate Change
Zakzeski J, Bruijnincx PCA, Jongerius AL, Weckhuysen BM (2010) The catalytic valorization of lignin for the production of renewable chemicals. Chem Rev 110(6):3552–3599
Parikka M (2004) Global biomass fuel resources. Biomass Bioenergy 27(6):613–620
Ragauskas AJ, Williams CK, Davison BH, Britovsek G, Cairney J, Eckert CA, Frederick WJ Jr, Hallett JP, Leak DJ, Liotta CL, Mielenz JR, Murphy R, Templer R, Tschaplinski T (2006) The path forward for biofuels and biomaterials. Science 311(5760):484–489
Jones S, Elliott DC, Kinchin C, Valkenburg C, Holladay J, Czemik S, Walton C, Stevens D (2009) Design case summary—production of gasoline and diesel from biomass via fast pyrolysis, hydrotreating and hydrocracking. US Department of Energy
Mohan D, Pittman CU, Steele PH (2006) Pyrolysis of wood/biomass for bio-oil: a critical review. Energy Fuel 20(3):848–889
Anex RP, Aden A, Kazi FK, Fortman J, Swanson RM, Wright MM, Satrio JA, Brown RC, Daugaard DE, Platon A, Kothandaraman G, Hsu DD, Dutta A (2010) Techno-economic comparison of biomass-to-transportation fuels via pyrolysis, gasification, and biochemical pathways. Fuel 89 Suppl 1:S29–S35
Caballero JA, Font R, Marcilla A (1996) Study of the primary pyrolysis of Kraft lignin at high heating rates: yields and kinetics. J Anal Appl Pyrolysis 36(2):159–178
Caballero JA, Font R, Marcilla A (1997) Pyrolysis of Kraft lignin: yields and correlations. J Anal Appl Pyrolysis 39(2):161–183
Caballero JA, Font R, Marcilla A, García AN (1993) Flash pyrolysis of Klason lignin in a Pyroprobe 1000. J Anal Appl Pyrolysis 27(2):221–244
Ferdous D, Dalai AK, Bej SK, Thring RW (2002) Pyrolysis of lignins: experimental and kinetics studies. Energy Fuel 16(6):1405–1412
Ferdous D, Dalai AK, Bej SK, Thring RW, Bakhshi NN (2001) Production of H2 and medium Btu gas via pyrolysis of lignins in a fixed-bed reactor. Fuel Process Technol 70(1):9–26
Iatridis B, Gavalas GR (1979) Pyrolysis of a precipitated Kraft lignin. Ind Eng Chem Prod RD 18(2):127–130
Nunn TR, Howard JB, Longwell JP, Peters WA (1985) Product compositions and kinetics in the rapid pyrolysis of milled wood lignin. Ind Eng Chem Process Des Dev 24(3):844–852
Ben H, Ragauskas AJ (2012) Torrefaction of Loblolly pine. Green Chem 14(1):72–76
Sharma RK, Hajaligol MR (2003) Effect of pyrolysis conditions on the formation of polycyclic aromatic hydrocarbons (PAHs) from polyphenolic compounds. J Anal Appl Pyrolysis 66:123–144
Sharma RK, Wooten JB, Baliga VL, Lin X, Geoffrey Chan W, Hajaligol MR (2004) Characterization of chars from pyrolysis of lignin. Fuel 83(11–12):1469–1482
Hosoya T, Kawamoto H, Saka S (2009) Role of methoxyl group in char formation from lignin-related compounds. J Anal Appl Pyrolysis 84(1):79–83
Chu S, Subrahmanyam AV, Huber GW (2013) The pyrolysis chemistry of a [small beta]-O-4 type oligomeric lignin model compound. Green Chem 15(1):125–136
Asmadi M, Kawamoto H, Saka S (2011) Gas- and solid/liquid-phase reactions during pyrolysis of softwood and hardwood lignins. J Anal Appl Pyrolysis 92(2):417–425
Chen H-W, Song Q-H, Liao B, Guo Q-X (2011) Further separation, characterization, and upgrading for upper and bottom layers from phase separation of biomass pyrolysis oils. Energy Fuel 25(10):4655–4661
Hosoya T, Kawamoto H, Saka S (2009) Solid/liquid- and vapor-phase interactions between cellulose- and lignin-derived pyrolysis products. J Anal Appl Pyrolysis 85(1–2):237–246
Hyder M, Jönsson JÅ (2012) Hollow-fiber liquid phase microextraction for lignin pyrolysis acids in aerosol samples and gas chromatography–mass spectrometry analysis. J Chromatogr A 1249:48–53
Jiang G, Nowakowski DJ, Bridgwater AV (2010) Effect of the temperature on the composition of lignin pyrolysis products. Energy Fuel 24(8):4470–4475
Lou R, S-b W, G-j L (2010) Effect of conditions on fast pyrolysis of bamboo lignin. J Anal Appl Pyrolysis 89(2):191–196
Lou R, Wu S-B, Lv G-J, Guo D-L (2010) pyrolytic products from rice straw and enzymatic/mild acidolysis lignin. BioRes 5(4):2184–2194
Mullen CA, Boateng AA (2010) Catalytic pyrolysis-GC/MS of lignin from several sources. Fuel Process Technol 91(11):1446–1458
Patwardhan PR, Brown RC, Shanks BH (2011) Understanding the fast pyrolysis of lignin. ChemSusChem 4(11):1629–1636
Yang Q, Wu S, Lou R, Lv G (2010) Analysis of wheat straw lignin by thermogravimetry and pyrolysis–gas chromatography/mass spectrometry. J Anal Appl Pyrolysis 87(1):65–69
Bocchini P, Galletti GC, Camarero S, Martinez AT (1997) Absolute quantitation of lignin pyrolysis products using an internal standard. J Chromatogr A 773(1–2):227–232
Greenwood PF, van Heemst JDH, Guthrie EA, Hatcher PG (2002) Laser micropyrolysis GC–MS of lignin. J Anal Appl Pyrolysis 62(2):365–373
Ingram L, Mohan D, Bricka M, Steele P, Strobel D, Crocker D, Mitchell B, Mohammad J, Cantrell K, Pittman CU (2008) Pyrolysis of wood and bark in an auger reactor: physical properties and chemical analysis of the produced bio-oils. Energy Fuel 22(1):614–625
Jegers HE, Klein MT (1985) Primary and secondary lignin pyrolysis reaction pathways. Ind Eng Chem Proc RD 24(1):173–183
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(1):53–72
Scholze B, Meier D (2001) Characterization of the water-insoluble fraction from pyrolysis oil (pyrolytic lignin). Part I. PY–GC/MS, FTIR, and functional groups. J Anal Appl Pyrolysis 60(1):41–54
Saiz-Jimenez C, De Leeuw JW (1986) Lignin pyrolysis products: their structures and their significance as biomarkers. Org Geochem 10(4–6):869–876
Scholze B, Hanser C, Meier D (2001) Characterization of the water-insoluble fraction from fast pyrolysis liquids (pyrolytic lignin): part II. GPC, carbonyl goups, and 13C-NMR. J Anal Appl Pyrolysis 58–59:387–400
Kosa M, Ben H, Theliander H, Ragauskas AJ (2011) Pyrolysis oils from CO2 precipitated Kraft lignin. Green Chem 13(11):3196
Ben H, Ragauskas AJ (2011) NMR characterization of pyrolysis oils from Kraft lignin. Energy Fuel 25(5):2322–2332
Huang Y, Wei Z, Qiu Z, Yin X, Wu C (2012) Study on structure and pyrolysis behavior of lignin derived from corncob acid hydrolysis residue. J Anal Appl Pyrolysis 93:153–159
Ke J, Singh D, Yang X, Chen S (2011) Thermal characterization of softwood lignin modification by termite Coptotermes formosanus (Shiraki). Biomass Bioenergy 35(8):3617–3626
Liu Q, Wang S, Zheng Y, Luo Z, Cen K (2008) Mechanism study of wood lignin pyrolysis by using TG–FTIR analysis. J Anal Appl Pyrolysis 82(1):170–177
Liu Q, Zhong Z, Wang S, Luo Z (2011) Interactions of biomass components during pyrolysis: a TG-FTIR study. J Anal Appl Pyrolysis 90(2):213–218
Shen DK, Gu S, Luo KH, Wang SR, Fang MX (2010) The pyrolytic degradation of wood-derived lignin from pulping process. Bioresour Technol 101(15):6136–6146
Wang S, Wang K, Liu Q, Gu Y, Luo Z, Cen K, Fransson T (2009) Comparison of the pyrolysis behavior of lignins from different tree species. Biotechnol Adv 27(5):562–567
Mullen CA, Strahan GD, Boateng AA (2009) Characterization of various fast-pyrolysis bio-oils by NMR spectroscopy. Energy Fuel 23(5):2707–2718
Luo Z, Wang S, Guo X (2012) Selective pyrolysis of Organosolv lignin over zeolites with product analysis by TG-FTIR. J Anal Appl Pyrolysis 95:112–117
Joseph J, Baker C, Mukkamala S, Beis SH, Wheeler MC, DeSisto WJ, Jensen BL, Frederick BG (2010) Chemical shifts and lifetimes for nuclear magnetic resonance (NMR) analysis of biofuels. Energy Fuel 24(9):5153–5162
Gr G, Li J, Eide I, Kleinert M, Barth T (2008) Chemical structures present in biofuel obtained from lignin. Energy Fuel 22(6):4240–4244
DeSisto WJ, Hill N, Beis SH, Mukkamala S, Joseph J, Baker C, Ong T-H, Stemmler EA, Wheeler MC, Frederick BG, van Heiningen A (2010) Fast pyrolysis of pine sawdust in a fluidized-bed reactor. Energy Fuel 24(4):2642–2651
David K, Kosa M, Williams A, Mayor R, Realff M, Muzzy J, Ragauskas A (2010) 31P-NMR analysis of bio-oils obtained from the pyrolysis of biomass. Biofuels 1(6):839–845
David K, Ben H, Muzzy J, Feik C, Iisa K, Ragauskas A (2012) Chemical characterization and water content determination of bio-oils obtained from various biomass species using 31P NMR spectroscopy. Biofuels 3(2):123–128
Ben H, Ragauskas AJ (2011) Pyrolysis of Kraft lignin with additives. Energy Fuel 25(10):4662–4668
Ben H, Ragauskas AJ (2011) Heteronuclear single-quantum correlation–nuclear magnetic resonance (HSQC–NMR) fingerprint analysis of pyrolysis oils. Energy Fuel 25(12):5791–5801
Beis SH, Mukkamala S, Hill N, Joseph J, Baker C, Jensen B, Stemmler EA, Wheeler MC, Frederick BG, van Heiningen A, Berg AG, DeSisto WJ (2010) Fast pyrolysis of lignins. BioRes 5(3):1408–1424
Runnebaum RC, Nimmanwudipong T, Block DE, Gates BC (2012) Catalytic conversion of compounds representative of lignin-derived bio-oils: a reaction network for guaiacol, anisole, 4-methylanisole, and cyclohexanone conversion catalysed by Pt/γ-Al2O3. Cat Sci Tec 2(1):113
Mortensen PM, Grunwaldt JD, Jensen PA, Knudsen KG, Jensen AD (2011) A review of catalytic upgrading of bio-oil to engine fuels. Appl Catal, A 407(1–2):1–19
Huber GW, Iborra S, Corma A (2006) Synthesis of transportation fuels from biomass: chemistry, catalysts, and engineering. Chem Rev 106(9):4044–4098
Czernik S, Bridgwater AV (2004) Overview of applications of biomass fast pyrolysis oil. Energy Fuels 18(2):590–598
Wang Y, Fang Y, He T, Hu H, Wu J (2011) Hydrodeoxygenation of dibenzofuran over noble metal supported on mesoporous zeolite. Catal Commun 12(13):1201–1205
Chantal PD, Kaliaguine S, Grandmaison JL (1985) Reactions of phenolic compounds over HZSM-5. Appl Catal 18(1):133–145
Gayubo AG, Aguayo AT, Atutxa A, Aguado R, Bilbao J (2004) Transformation of oxygenate components of biomass pyrolysis oil on a HZSM-5 zeolite. Alcohols and phenols. Ind Eng Chem Res 43(11):2610–2618
Zhu X, Mallinson RG, Resasco DE (2010) Role of transalkylation reactions in the conversion of anisole over HZSM-5. Appl Catal A 379(1–2):172–181
Wildschut J, Iqbal M, Mahfud FH, Cabrera IM, Venderbosch RH, Heeres HJ (2010) Insights in the hydrotreatment of fast pyrolysis oil using a ruthenium on carbon catalyst. Energy Environ Sci 3(7):962
Furimsky E (1983) Chemistry of catalytic hydrodeoxygenation. Catal Rev-Sci Eng 25(3):421–458
Furimsky E (2000) Catalytic hydrodeoxygenation. Appl Catal A 199(2):147–190
Elliott DC (2007) Historical developments in hydroprocessing bio-oils. Energy Fuel 21(3):1792–1815
Choudhary TV, Phillips CB (2011) Renewable fuels via catalytic hydrodeoxygenation. Appl Catal A 397(1–2):1–12
Bu Q, Lei H, Zacher AH, Wang L, Ren S, Liang J, Wei Y, Liu Y, Tang J, Zhang Q, Ruan R (2012) A review of catalytic hydrodeoxygenation of lignin-derived phenols from biomass pyrolysis. Bioresour Technol 124:470–477
IEA Energy Technology Essentials (2007). Hydrogen Production and Distribution. http://www.iea.org/techno/essentials5.pdf. Accessed Feb 18, 2013
Pan C, Chen A, Liu Z, Chen P, Lou H, Zheng X (2012) Aqueous-phase reforming of the low-boiling fraction of rice husk pyrolyzed bio-oil in the presence of platinum catalyst for hydrogen production. Bioresour Technol 125:335–339
Wright MM, Román-Leshkov Y, Green WH (2012) Investigating the techno-economic trade-offs of hydrogen source using a response surface model of drop-in biofuel production via bio-oil upgrading. Biofuels, Bioprod Biorefin 6(5):503–520
Wright MM, Satrio JA, Brown RC, Daugaard DE, Hsu DD (2010) Techno-economic analysis of biomass fast pyrolysis to transportation fuels. Technical Report by NREL.
Jones S, Holladay J, Valkenburg C, Stevens D, Walton C, Kinchin C, Elliott D, Czernik S (2009) Production of gasoline and diesel from biomass via fast pyrolysis, hydrotreating and hydrocracking: a design case. PNNL-18284.
Odebunmi EO, Ollis DF (1983) Catalytic hydrodeoxygenation: I. Conversions of o-, p-, and m-cresols. J Catal 80(1):56–64
Odebunmi EO, Ollis DF (1983) Catalytic hydrodeoxygenation: II. Interactions between catalytic hydrodeoxygenation of m-cresol and hydrodesulfurization of benzothiophene and dibenzothiophene. J Catal 80(1):65–75
Gevert BS, Otterstedt JE, Massoth FE (1987) Kinetics of the HDO of methyl-substituted phenols. Appl Catal 31(1):119–131
Elliott DC, Beckman D, Bridgwater AV, Diebold JP, Gevert SB, Solantausta Y (1991) Developments in direct thermochemical liquefaction of biomass: 1983–1990. Energy Fuel 5(3):399–410
Viljava TR, Komulainen RS, Krause AOI (2000) Effect of H2S on the stability of CoMo/Al2O3 catalysts during hydrodeoxygenation. Catal Today 60(1–2):83–92
Furimsky E, Massoth FE (1999) Deactivation of hydroprocessing catalysts. Catal Today 52(4):381–495
Laurent E, Delmon B (1994) Influence of water in the deactivation of a sulfided NiMoγ-Al2O3 catalyst during hydrodeoxygenation. J Catal 146(1):281–291
Centeno A, Laurent E, Delmon B (1995) Influence of the support of CoMo sulfide catalysts and of the addition of potassium and platinum on the catalytic performances for the hydrodeoxygenation of carbonyl, carboxyl, and guaiacol-type molecules. J Catal 154(2):288–298
Honkela ML, Björk J, Persson M (2012) Computational study of the adsorption and dissociation of phenol on Pt and Rh surfaces. PCCP 14(16):5849
Niquille-Röthlisberger A, Prins R (2006) Hydrodesulfurization of 4,6-dimethyldibenzothiophene and dibenzothiophene over alumina-supported Pt, Pd, and Pt-Pd catalysts. J Catal 242(1):207–216
Tang T, Yin C, Wang L, Ji Y, Xiao F-S (2007) Superior performance in deep saturation of bulky aromatic pyrene over acidic mesoporous beta zeolite-supported palladium catalyst. J Catal 249(1):111–115
Schuman S, Field S (1970) Hydrogenation of sulphite waste liquor. CA Patent 851709, 15 Sept 1970
Ryymin E-M, Honkela ML, Viljava T-R, Krause AOI (2010) Competitive reactions and mechanisms in the simultaneous HDO of phenol and methyl heptanoate over sulphided NiMo/γ-Al2O3. Appl Catal A 389(1–2):114–121
Lin Y-C, Li C-L, Wan H-P, Lee H-T, Liu C-F (2011) Catalytic hydrodeoxygenation of guaiacol on Rh-based and sulfided CoMo and NiMo catalysts. Energy Fuel 25(3):890–896
Jongerius AL, Jastrzebski R, Bruijnincx PCA, Weckhuysen BM (2012) CoMo sulfide-catalyzed hydrodeoxygenation of lignin model compounds: an extended reaction network for the conversion of monomeric and dimeric substrates. J Catal 285(1):315–323
Ruinart de Brimont M, Dupont C, Daudin A, Geantet C, Raybaud P (2012) Deoxygenation mechanisms on Ni-promoted MoS2 bulk catalysts: a combined experimental and theoretical study. J Catal 286:153–164
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 101(3–4):239–245
Romero Y, Richard F, Brunet S (2010) Hydrodeoxygenation of 2-ethylphenol as a model compound of bio-crude over sulfided Mo-based catalysts: promoting effect and reaction mechanism. Appl Catal, B 98(3–4):213–223
Badawi M, Paul JF, Cristol S, Payen E, Romero Y, Richard F, Brunet S, Lambert D, Portier X, Popov A, Kondratieva E, Goupil JM, El Fallah J, Gilson JP, Mariey L, Travert A, Maugé F (2011) Effect of water on the stability of Mo and CoMo hydrodeoxygenation catalysts: a combined experimental and DFT study. J Catal 282(1):155–164
Do PTM, Foster AJ, Chen J, Lobo RF (2012) Bimetallic effects in the hydrodeoxygenation of meta-cresol on γ-Al2O3 supported Pt–Ni and Pt–Co catalysts. Green Chem 14(5):1388
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(7):1038
Lee CR, Yoon JS, Suh Y-W, Choi J-W, Ha J-M, Suh DJ, Park Y-K (2012) Catalytic roles of metals and supports on hydrodeoxygenation of lignin monomer guaiacol. Catal Commun 17:54–58
Zhu X, Lobban LL, Mallinson RG, Resasco DE (2011) Bifunctional transalkylation and hydrodeoxygenation of anisole over a Pt/HBeta catalyst. J Catal 281(1):21–29
Pham TT, Lobban LL, Resasco DE, Mallinson RG (2009) Hydrogenation and hydrodeoxygenation of 2-methyl-2-pentenal on supported metal catalysts. J Catal 266(1):9–14
Ohta H, Kobayashi H, Hara K, Fukuoka A (2011) Hydrodeoxygenation of phenols as lignin models under acid-free conditions with carbon-supported platinum catalysts. Chem Commun 47(44):12209
Li N, Tompsett GA, Zhang T, Shi J, Wyman CE, Huber GW (2011) Renewable gasoline from aqueous phase hydrodeoxygenation of aqueous sugar solutions prepared by hydrolysis of maple wood. Green Chem 13(1):91
Gutierrez A, Kaila RK, Honkela ML, Slioor R, Krause AOI (2009) Hydrodeoxygenation of guaiacol on noble metal catalysts. Catal Today 147(3–4):239–246
Liu C, Shao Z, Xiao Z, Williams CT, Liang C (2012) Hydrodeoxygenation of benzofuran over silica–alumina-supported Pt, Pd, and Pt–Pd catalysts. Energy Fuel 26(7):4205–4211
Beccat P, Bertolini JC, Gauthier Y, Massardier J, Ruiz P (1990) Crotonaldehyde and methylcrotonaldehyde hydrogenation over Pt(111) and Pt80Fe20(111) single crystals. J Catal 126(2):451–456
Birchem T, Pradier CM, Berthier Y, Cordier G (1994) Reactivity of 3-methyl-crotonaldehyde on Pt(111). J Catal 146(2):503–510
Jiang H, Yang H, Hawkins R, Ring Z (2007) Effect of palladium on sulfur resistance in Pt–Pd bimetallic catalysts. Catal Today 125(3–4):282–290
Bonalumi N, Vargas A, Ferri D, Baiker A (2006) Theoretical and spectroscopic study of the effect of ring substitution on the adsorption of anisole on platinum. J Phys Chem B 110(20):9956–9965
Lu S, Lonergan WW, Bosco JP, Wang S, Zhu Y, Xie Y, Chen JG (2008) Low temperature hydrogenation of benzene and cyclohexene: a comparative study between γ-Al2O3 supported PtCo and PtNi bimetallic catalysts. J Catal 259(2):260–268
Lu S, Menning CA, Zhu Y, Chen JG (2009) Correlating benzene hydrogenation activity with binding energies of hydrogen and benzene on Co-based bimetallic catalysts. ChemPhysChem 10(11):1763–1765
Lonergan WW, Vlachos DG, Chen JG (2010) Correlating extent of Pt–Ni bond formation with low-temperature hydrogenation of benzene and 1,3-butadiene over supported Pt/Ni bimetallic catalysts. J Catal 271(2):239–250
Zhao C, He J, Lemonidou AA, Li X, Lercher JA (2011) Aqueous-phase hydrodeoxygenation of bio-derived phenols to cycloalkanes. J Catal 280(1):8–16
Zhao C, Kou Y, Lemonidou AA, Li X, Lercher JA (2009) Highly selective catalytic conversion of phenolic bio-oil to alkanes. Angew Chem Int Ed 48(22):3987–3990
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(1):64–68
Velu S, Kapoor MP, Inagaki S, Suzuki K (2003) Vapor phase hydrogenation of phenol over palladium supported on mesoporous CeO2 and ZrO2. Appl Catal A 245(2):317–331
Chen YZ, Liaw CW, Lee LI (1999) Selective hydrogenation of phenol to cyclohexanone over palladium supported on calcined Mg/Al hydrotalcite. Appl Catal A 177(1):1–8
Neri G, Visco AM, Donato A, Milone C, Malentacchi M, Gubitosa G (1994) Hydrogenation of phenol to cyclohexanone over palladium and alkali-doped palladium catalysts. Appl Catal A 110(1):49–59
Talukdar AK, Bhattacharyya KG, Sivasanker S (1993) Hydrogenation of phenol over supported platinum and palladium catalysts. Appl Catal A 96(2):229–239
Orita H, Itoh N (2004) Simulation of phenol formation from benzene with a Pd membrane reactor: a b initio periodic density functional study. Appl Catal A 258(1):17–23
Ihm H, White JM (2000) Stepwise dissociation of thermally activated phenol on Pt(111). J Phys Chem B 104(26):6202–6211
Xu X, Friend CM (1989) The role of coverage in determining adsorbate stability: phenol reactivity on rhodium(111). J Phys Chem 93(24):8072–8080
Kluson P, Cerveny L (1996) Hydrogenation of substituted aromatic compounds over a ruthenium catalyst. J Mol Catal A Chem 108(2):107–112
Guo J, Ruan R, Zhang Y (2012) Hydrotreating of phenolic compounds separated from bio-oil to alcohols. Ind Eng Chem Res 51(19):6599–6604
Greenfield H (1973) Studies in nuclear hydrogenation. Ann NY Acad Sci 214(1):233–242
Nimmanwudipong T, Runnebaum R, Block D, Gates B (2011) Catalytic reactions of guaiacol: reaction network and evidence of oxygen removal in reactions with hydrogen. Catal Lett 141(6):779–783
Runnebaum R, Nimmanwudipong T, Block D, Gates B (2011) Catalytic conversion of anisole: evidence of oxygen removal in reactions with hydrogen. Catal Lett 141(6):817–820
Sato S, Takahashi R, Sodesawa T, Matsumoto K, Kamimura Y (1999) Ortho-selective alkylation of phenol with 1-propanol catalyzed by CeO2–MgO. J Catal 184(1):180–188
Auroux A, Artizzu P, Ferino I, Solinas V, Leofanti G, Padovan M, Messina G, Mansani R (1995) Dehydration of 4-methylpentan-2-ol over zirconia catalysts. J Chem Soc Faraday Trans 91(18):3263–3267
Mahata N, Raghavan KV, Vishwanathan V, Park C, Keane MA (2001) Phenol hydrogenation over palladium supported on magnesia: relationship between catalyst structure and performance. PCCP 3(13):2712–2719
Shin E-J, Keane MA (2000) Gas-phase hydrogenation/hydrogenolysis of phenol over supported nickel catalysts. Ind Eng Chem Res 39(4):883–892
Aprile C, Abad A, Garcia H, Corma A (2005) Synthesis and catalytic activity of periodic mesoporous materials incorporating gold nanoparticles. J Mater Chem 15(41):4408–4413
Fournier RO, Rowe JJ (1977) The solubility of amorphous silica in water at high temperatures and high pressures. Am Mineral 62:1052–1056
Lefèvre G, Duc M, Lepeut P, Caplain R, Fédoroff M (2002) Hydration of γ-alumina in water and its effects on surface reactivity. Langmuir 18(20):7530–7537
Britt PF, Buchanan AC, Cooney MJ, Martineau DR (2000) Flash vacuum pyrolysis of methoxy-substituted lignin model compounds. J Org Chem 65(5):1376–1389
Britt PF, Buchanan AC, Malcolm EA (2000) Impact of restricted mass transport on pyrolysis pathways for aryl ether containing lignin model compounds. Energy Fuel 14(6):1314–1322
Britt PF, Kidder MK, Buchanan AC (2007) Oxygen substituent effects in the pyrolysis of phenethyl phenyl ethers. Energy Fuel 21(6):3102–3108
Kawamoto H, Nakamura T, Saka S (2008) Pyrolytic cleavage mechanisms of lignin–ether linkages: a study on p-substituted dimers and trimers. Holzforschung 62:50–56
Kawamoto H, Ryoritani M, Saka S (2008) Different pyrolytic cleavage mechanisms of β-ether bond depending on the side-chain structure of lignin dimers. J Anal Appl Pyrolysis 81(1):88–94
Kawamoto H, Saka S (2007) Role of side–chain hydroxyl groups in pyrolytic reaction of phenolic β–ether type of lignin dimer. J Wood Chem Technol 27(2):113–120
Kawamoto H, Horigoshi S, Saka S (2007) Pyrolysis reactions of various lignin model dimers. J Wood Sci 53(2):168–174
Beis SH, Mukkamala S, Hill N, Joseph J, Baker C, Jensen B, Stemmler EA, Wheeler MC, Frederick BG, Av H, Berg AG, DeSisto WJ (2010) Fast pyrolysis of lignins. BioRes 5:17
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Mu, W., Ben, H., Ragauskas, A. et al. Lignin Pyrolysis Components and Upgrading—Technology Review. Bioenerg. Res. 6, 1183–1204 (2013). https://doi.org/10.1007/s12155-013-9314-7
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12155-013-9314-7