BioEnergy Research

, Volume 6, Issue 4, pp 1183–1204 | Cite as

Lignin Pyrolysis Components and Upgrading—Technology Review

Article

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.

Keywords

Lignin Pyrolysis Catalyst Oil upgrade Hydrodeoxygenation Biofuel 

Reference

  1. 1.
    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 2005Google Scholar
  2. 2.
    Administration EI (June 2012) Monthly Energy Review. US Department of EnergyGoogle Scholar
  3. 3.
    Administration-0384 EI (2011) Annual Energy Review 2010. Department of EnergyGoogle Scholar
  4. 4.
    Franks JR, Hadingham B (2012) Reducing greenhouse gas emissions from agriculture: avoiding trivial solutions to a global problem. Land Use Policy 29(4):727–736Google Scholar
  5. 5.
    Iribarren D, Peters JF, Dufour J (2012) Life cycle assessment of transportation fuels from biomass pyrolysis. Fuel 97:812–821Google Scholar
  6. 6.
    van Oort PAJ, Timmermans BGH, van Swaaij ACPM (2012) Why farmers’ sowing dates hardly change when temperature rises. Eur J Agron 40:102–111Google Scholar
  7. 7.
    Lenzen M, Schaeffer R (2012) Historical and potential future contributions of power technologies to global warming. Clim Change 112(3):601–632Google Scholar
  8. 8.
    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):819–845Google Scholar
  9. 9.
    Climate Change 2007: Synthesis Report (2007). Intergovernmental Panel on Climate ChangeGoogle Scholar
  10. 10.
    Zakzeski J, Bruijnincx PCA, Jongerius AL, Weckhuysen BM (2010) The catalytic valorization of lignin for the production of renewable chemicals. Chem Rev 110(6):3552–3599PubMedGoogle Scholar
  11. 11.
    Parikka M (2004) Global biomass fuel resources. Biomass Bioenergy 27(6):613–620Google Scholar
  12. 12.
    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):484–489PubMedGoogle Scholar
  13. 13.
    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 EnergyGoogle Scholar
  14. 14.
    Mohan D, Pittman CU, Steele PH (2006) Pyrolysis of wood/biomass for bio-oil: a critical review. Energy Fuel 20(3):848–889Google Scholar
  15. 15.
    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–S35Google Scholar
  16. 16.
    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):159–178Google Scholar
  17. 17.
    Caballero JA, Font R, Marcilla A (1997) Pyrolysis of Kraft lignin: yields and correlations. J Anal Appl Pyrolysis 39(2):161–183Google Scholar
  18. 18.
    Caballero JA, Font R, Marcilla A, García AN (1993) Flash pyrolysis of Klason lignin in a Pyroprobe 1000. J Anal Appl Pyrolysis 27(2):221–244Google Scholar
  19. 19.
    Ferdous D, Dalai AK, Bej SK, Thring RW (2002) Pyrolysis of lignins: experimental and kinetics studies. Energy Fuel 16(6):1405–1412Google Scholar
  20. 20.
    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):9–26Google Scholar
  21. 21.
    Iatridis B, Gavalas GR (1979) Pyrolysis of a precipitated Kraft lignin. Ind Eng Chem Prod RD 18(2):127–130Google Scholar
  22. 22.
    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):844–852Google Scholar
  23. 23.
    Ben H, Ragauskas AJ (2012) Torrefaction of Loblolly pine. Green Chem 14(1):72–76Google Scholar
  24. 24.
    Sharma RK, Hajaligol MR (2003) Effect of pyrolysis conditions on the formation of polycyclic aromatic hydrocarbons (PAHs) from polyphenolic compounds. J Anal Appl Pyrolysis 66:123–144Google Scholar
  25. 25.
    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):1469–1482Google Scholar
  26. 26.
    Hosoya T, Kawamoto H, Saka S (2009) Role of methoxyl group in char formation from lignin-related compounds. J Anal Appl Pyrolysis 84(1):79–83Google Scholar
  27. 27.
    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):125–136Google Scholar
  28. 28.
    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):417–425Google Scholar
  29. 29.
    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):4655–4661Google Scholar
  30. 30.
    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):237–246Google Scholar
  31. 31.
    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 1249:48–53PubMedGoogle Scholar
  32. 32.
    Jiang G, Nowakowski DJ, Bridgwater AV (2010) Effect of the temperature on the composition of lignin pyrolysis products. Energy Fuel 24(8):4470–4475Google Scholar
  33. 33.
    Lou R, S-b W, G-j L (2010) Effect of conditions on fast pyrolysis of bamboo lignin. J Anal Appl Pyrolysis 89(2):191–196Google Scholar
  34. 34.
    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):2184–2194Google Scholar
  35. 35.
    Mullen CA, Boateng AA (2010) Catalytic pyrolysis-GC/MS of lignin from several sources. Fuel Process Technol 91(11):1446–1458Google Scholar
  36. 36.
    Patwardhan PR, Brown RC, Shanks BH (2011) Understanding the fast pyrolysis of lignin. ChemSusChem 4(11):1629–1636PubMedGoogle Scholar
  37. 37.
    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):65–69Google Scholar
  38. 38.
    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):227–232Google Scholar
  39. 39.
    Greenwood PF, van Heemst JDH, Guthrie EA, Hatcher PG (2002) Laser micropyrolysis GC–MS of lignin. J Anal Appl Pyrolysis 62(2):365–373Google Scholar
  40. 40.
    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):614–625Google Scholar
  41. 41.
    Jegers HE, Klein MT (1985) Primary and secondary lignin pyrolysis reaction pathways. Ind Eng Chem Proc RD 24(1):173–183Google Scholar
  42. 42.
    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):53–72Google Scholar
  43. 43.
    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):41–54Google Scholar
  44. 44.
    Saiz-Jimenez C, De Leeuw JW (1986) Lignin pyrolysis products: their structures and their significance as biomarkers. Org Geochem 10(4–6):869–876Google Scholar
  45. 45.
    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 58–59:387–400Google Scholar
  46. 46.
    Kosa M, Ben H, Theliander H, Ragauskas AJ (2011) Pyrolysis oils from CO2 precipitated Kraft lignin. Green Chem 13(11):3196Google Scholar
  47. 47.
    Ben H, Ragauskas AJ (2011) NMR characterization of pyrolysis oils from Kraft lignin. Energy Fuel 25(5):2322–2332Google Scholar
  48. 48.
    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 93:153–159Google Scholar
  49. 49.
    Ke J, Singh D, Yang X, Chen S (2011) Thermal characterization of softwood lignin modification by termite Coptotermes formosanus (Shiraki). Biomass Bioenergy 35(8):3617–3626Google Scholar
  50. 50.
    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):170–177Google Scholar
  51. 51.
    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):213–218Google Scholar
  52. 52.
    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):6136–6146PubMedGoogle Scholar
  53. 53.
    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):562–567PubMedGoogle Scholar
  54. 54.
    Mullen CA, Strahan GD, Boateng AA (2009) Characterization of various fast-pyrolysis bio-oils by NMR spectroscopy. Energy Fuel 23(5):2707–2718Google Scholar
  55. 55.
    Luo Z, Wang S, Guo X (2012) Selective pyrolysis of Organosolv lignin over zeolites with product analysis by TG-FTIR. J Anal Appl Pyrolysis 95:112–117Google Scholar
  56. 56.
    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):5153–5162Google Scholar
  57. 57.
    Gr G, Li J, Eide I, Kleinert M, Barth T (2008) Chemical structures present in biofuel obtained from lignin. Energy Fuel 22(6):4240–4244Google Scholar
  58. 58.
    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):2642–2651Google Scholar
  59. 59.
    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):839–845Google Scholar
  60. 60.
    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):123–128Google Scholar
  61. 61.
    Ben H, Ragauskas AJ (2011) Pyrolysis of Kraft lignin with additives. Energy Fuel 25(10):4662–4668Google Scholar
  62. 62.
    Ben H, Ragauskas AJ (2011) Heteronuclear single-quantum correlation–nuclear magnetic resonance (HSQC–NMR) fingerprint analysis of pyrolysis oils. Energy Fuel 25(12):5791–5801Google Scholar
  63. 63.
    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):1408–1424Google Scholar
  64. 64.
    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):113Google Scholar
  65. 65.
    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):1–19Google Scholar
  66. 66.
    Huber GW, Iborra S, Corma A (2006) Synthesis of transportation fuels from biomass: chemistry, catalysts, and engineering. Chem Rev 106(9):4044–4098PubMedGoogle Scholar
  67. 67.
    Czernik S, Bridgwater AV (2004) Overview of applications of biomass fast pyrolysis oil. Energy Fuels 18(2):590–598Google Scholar
  68. 68.
    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):1201–1205Google Scholar
  69. 69.
    Chantal PD, Kaliaguine S, Grandmaison JL (1985) Reactions of phenolic compounds over HZSM-5. Appl Catal 18(1):133–145Google Scholar
  70. 70.
    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):2610–2618Google Scholar
  71. 71.
    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):172–181Google Scholar
  72. 72.
    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):962Google Scholar
  73. 73.
    Furimsky E (1983) Chemistry of catalytic hydrodeoxygenation. Catal Rev-Sci Eng 25(3):421–458Google Scholar
  74. 74.
    Furimsky E (2000) Catalytic hydrodeoxygenation. Appl Catal A 199(2):147–190Google Scholar
  75. 75.
    Elliott DC (2007) Historical developments in hydroprocessing bio-oils. Energy Fuel 21(3):1792–1815Google Scholar
  76. 76.
    Choudhary TV, Phillips CB (2011) Renewable fuels via catalytic hydrodeoxygenation. Appl Catal A 397(1–2):1–12Google Scholar
  77. 77.
    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 124:470–477PubMedGoogle Scholar
  78. 78.
    IEA Energy Technology Essentials (2007). Hydrogen Production and Distribution. http://www.iea.org/techno/essentials5.pdf. Accessed Feb 18, 2013
  79. 79.
    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 125:335–339PubMedGoogle Scholar
  80. 80.
    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):503–520Google Scholar
  81. 81.
    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.Google Scholar
  82. 82.
    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.Google Scholar
  83. 83.
    Odebunmi EO, Ollis DF (1983) Catalytic hydrodeoxygenation: I. Conversions of o-, p-, and m-cresols. J Catal 80(1):56–64Google Scholar
  84. 84.
    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):65–75Google Scholar
  85. 85.
    Gevert BS, Otterstedt JE, Massoth FE (1987) Kinetics of the HDO of methyl-substituted phenols. Appl Catal 31(1):119–131Google Scholar
  86. 86.
    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):399–410Google Scholar
  87. 87.
    Viljava TR, Komulainen RS, Krause AOI (2000) Effect of H2S on the stability of CoMo/Al2O3 catalysts during hydrodeoxygenation. Catal Today 60(1–2):83–92Google Scholar
  88. 88.
    Furimsky E, Massoth FE (1999) Deactivation of hydroprocessing catalysts. Catal Today 52(4):381–495Google Scholar
  89. 89.
    Laurent E, Delmon B (1994) Influence of water in the deactivation of a sulfided NiMoγ-Al2O3 catalyst during hydrodeoxygenation. J Catal 146(1):281–291Google Scholar
  90. 90.
    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):288–298Google Scholar
  91. 91.
    Honkela ML, Björk J, Persson M (2012) Computational study of the adsorption and dissociation of phenol on Pt and Rh surfaces. PCCP 14(16):5849PubMedGoogle Scholar
  92. 92.
    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):207–216Google Scholar
  93. 93.
    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):111–115Google Scholar
  94. 94.
    Schuman S, Field S (1970) Hydrogenation of sulphite waste liquor. CA Patent 851709, 15 Sept 1970Google Scholar
  95. 95.
    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):114–121Google Scholar
  96. 96.
    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):890–896Google Scholar
  97. 97.
    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):315–323Google Scholar
  98. 98.
    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 286:153–164Google Scholar
  99. 99.
    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):239–245Google Scholar
  100. 100.
    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):213–223Google Scholar
  101. 101.
    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):155–164Google Scholar
  102. 102.
    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):1388Google Scholar
  103. 103.
    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):1038Google Scholar
  104. 104.
    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 17:54–58Google Scholar
  105. 105.
    Zhu X, Lobban LL, Mallinson RG, Resasco DE (2011) Bifunctional transalkylation and hydrodeoxygenation of anisole over a Pt/HBeta catalyst. J Catal 281(1):21–29Google Scholar
  106. 106.
    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):9–14Google Scholar
  107. 107.
    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):12209Google Scholar
  108. 108.
    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):91Google Scholar
  109. 109.
    Gutierrez A, Kaila RK, Honkela ML, Slioor R, Krause AOI (2009) Hydrodeoxygenation of guaiacol on noble metal catalysts. Catal Today 147(3–4):239–246Google Scholar
  110. 110.
    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):4205–4211Google Scholar
  111. 111.
    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):451–456Google Scholar
  112. 112.
    Birchem T, Pradier CM, Berthier Y, Cordier G (1994) Reactivity of 3-methyl-crotonaldehyde on Pt(111). J Catal 146(2):503–510Google Scholar
  113. 113.
    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):282–290Google Scholar
  114. 114.
    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):9956–9965PubMedGoogle Scholar
  115. 115.
    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):260–268Google Scholar
  116. 116.
    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):1763–1765PubMedGoogle Scholar
  117. 117.
    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):239–250Google Scholar
  118. 118.
    Zhao C, He J, Lemonidou AA, Li X, Lercher JA (2011) Aqueous-phase hydrodeoxygenation of bio-derived phenols to cycloalkanes. J Catal 280(1):8–16Google Scholar
  119. 119.
    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):3987–3990Google Scholar
  120. 120.
    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):64–68Google Scholar
  121. 121.
    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):317–331Google Scholar
  122. 122.
    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):1–8Google Scholar
  123. 123.
    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):49–59Google Scholar
  124. 124.
    Talukdar AK, Bhattacharyya KG, Sivasanker S (1993) Hydrogenation of phenol over supported platinum and palladium catalysts. Appl Catal A 96(2):229–239Google Scholar
  125. 125.
    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):17–23Google Scholar
  126. 126.
    Ihm H, White JM (2000) Stepwise dissociation of thermally activated phenol on Pt(111). J Phys Chem B 104(26):6202–6211Google Scholar
  127. 127.
    Xu X, Friend CM (1989) The role of coverage in determining adsorbate stability: phenol reactivity on rhodium(111). J Phys Chem 93(24):8072–8080Google Scholar
  128. 128.
    Kluson P, Cerveny L (1996) Hydrogenation of substituted aromatic compounds over a ruthenium catalyst. J Mol Catal A Chem 108(2):107–112Google Scholar
  129. 129.
    Guo J, Ruan R, Zhang Y (2012) Hydrotreating of phenolic compounds separated from bio-oil to alcohols. Ind Eng Chem Res 51(19):6599–6604Google Scholar
  130. 130.
    Greenfield H (1973) Studies in nuclear hydrogenation. Ann NY Acad Sci 214(1):233–242PubMedGoogle Scholar
  131. 131.
    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):779–783Google Scholar
  132. 132.
    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):817–820Google Scholar
  133. 133.
    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):180–188Google Scholar
  134. 134.
    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):3263–3267Google Scholar
  135. 135.
    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):2712–2719Google Scholar
  136. 136.
    Shin E-J, Keane MA (2000) Gas-phase hydrogenation/hydrogenolysis of phenol over supported nickel catalysts. Ind Eng Chem Res 39(4):883–892Google Scholar
  137. 137.
    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):4408–4413Google Scholar
  138. 138.
    Fournier RO, Rowe JJ (1977) The solubility of amorphous silica in water at high temperatures and high pressures. Am Mineral 62:1052–1056Google Scholar
  139. 139.
    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):7530–7537Google Scholar
  140. 140.
    Britt PF, Buchanan AC, Cooney MJ, Martineau DR (2000) Flash vacuum pyrolysis of methoxy-substituted lignin model compounds. J Org Chem 65(5):1376–1389PubMedGoogle Scholar
  141. 141.
    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):1314–1322Google Scholar
  142. 142.
    Britt PF, Kidder MK, Buchanan AC (2007) Oxygen substituent effects in the pyrolysis of phenethyl phenyl ethers. Energy Fuel 21(6):3102–3108Google Scholar
  143. 143.
    Kawamoto H, Nakamura T, Saka S (2008) Pyrolytic cleavage mechanisms of lignin–ether linkages: a study on p-substituted dimers and trimers. Holzforschung 62:50–56Google Scholar
  144. 144.
    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):88–94Google Scholar
  145. 145.
    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):113–120Google Scholar
  146. 146.
    Kawamoto H, Horigoshi S, Saka S (2007) Pyrolysis reactions of various lignin model dimers. J Wood Sci 53(2):168–174Google Scholar
  147. 147.
    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 5:17Google Scholar

Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • Wei Mu
    • 1
    • 2
  • Haoxi Ben
    • 2
    • 3
  • Art Ragauskas
    • 2
    • 3
  • Yulin Deng
    • 1
    • 2
  1. 1.School of Chemical and Biomolecular EngineeringGeorgia Institute of TechnologyAtlantaUSA
  2. 2.Institute of Paper Science and TechnologyGeorgia Institute of TechnologyAtlantaUSA
  3. 3.School of Chemistry and BiochemistryGeorgia Institute of TechnologyAtlantaUSA

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