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Review of Biomass Conversion in High Pressure High Temperature Water (HHW) Including Recent Experimental Results (Isomerization and Carbonization)

  • Masaru WatanabeEmail author
  • Taku M. Aida
  • Richard Lee Smith
Chapter
Part of the Green Chemistry and Sustainable Technology book series (GCST)

Abstract

In this chapter, we briefly explain unique properties of high pressure high temperature water (HHW). In high pressure media, concentration of reactant can be controlled by changing temperature and pressure, and the reaction rate (also product distribution) can be controlled. In addition, in the presence of solvent (water is concerned here), the properties of the solvent can also be adjusted by pressure and temperature, and the control of solvent properties can help to improve the reaction rate and selectivity. Some of important reactions occurring in the high pressure high temperature water (HHW) media are summarized and the relationship between the reactions and the products is roughly categorized into gasification, liquefaction, and carbonization. Briefly, over 400 °C, radical reaction is dominant and thus gasification (small fragment formation) occurs. Between 200 and 400 °C, both ionic and radial reactions competitively occur and biomass conversion can be controlled widely by changing temperature and pressures. Therefore, production of chemical block for industries is performed in the temperature range. Below 200 °C, namely low temperature and high density of water (liquid phase of water), hydrolysis and dehydration are favored because ionic reactions are predominant. Through dehydration between molecules (high concentration condition is preferred), carbonization is also developed. Concerning each product category, our research topics are briefly overviewed. Finally, our recent experimental results for isomerization of glucose and carbonization of biomass are roughly introduced.

Keywords

Partial Oxidation Carbonaceous Material Supercritical Water Water Loading Biomass Conversion 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

References

  1. 1.
    Watanabe M, Kato S, Ishizeki S, Inomata H, Smith RL Jr (2010) Heavy oil upgrading in the presence of high density water: Basic study. J Supercrit Fluids 53:48–52CrossRefGoogle Scholar
  2. 2.
    Savage PE (1999) Organic chemical reactions in supercritical water. Chem Rev 99:603–622CrossRefGoogle Scholar
  3. 3.
    Adschiri T, Shibata R, Sato T, Watanabe M, Arai K (1998) Catalytichydrodesulphurization of dibenzothiophene through partial oxidation and a water-gas shift reaction in supercritical water. Ind Eng Chem Res 37:2634–2638CrossRefGoogle Scholar
  4. 4.
    Arai K, Adschiri T, Watanabe M (2000) Hydrogenation of Hydrocarbons through Partial Oxidation in Supercritical Water. Ind Eng Chem Res 39:4697–4701CrossRefGoogle Scholar
  5. 5.
    Akiya N, Savage PE (2002) Roles of water for chemical reactions in high-temperature water. Chem Rev 102:2725–2750CrossRefGoogle Scholar
  6. 6.
    Uematsu M, Franck EU (1980) J Phys Chem Ref Data 9:1291–1306CrossRefGoogle Scholar
  7. 7.
    Marrone PA, Arias TA, Peters WA, Tester JW (1998) Solvation effects on kinetics of methylene chloride reactions in sub- and supercritical water: theory, experiment, and Ab initio calculations. Phys Chem. A 102:7013–7028CrossRefGoogle Scholar
  8. 8.
    Salvatierra D, Taylor JD, Marrone PA, Tester JW (1999) Kinetic study of hydrolysis of methylene chloride from 100 to 500 °C. Ind Eng Chem Res 38:4169–4174CrossRefGoogle Scholar
  9. 9.
    Sasaki M, Kabyemela B, Malaluan R, Hirose S, Takeda N, Adschiri T, Arai K (1998) Cellulose hydrolysis in subcritical and supercritical water. J. Supercrit. Fluid 13:261–268CrossRefGoogle Scholar
  10. 10.
    Marshall WL, Franck EU (1981) J Phys Chem Ref Data 10:295–304CrossRefGoogle Scholar
  11. 11.
    Tomita K, Oshima Y (2004) Enhancement of the catalytic activity by an ion product of sub and supercritical water in the catalytic hydration of propylene with metal oxide. Ind Eng Chem Res 43:2345–2348CrossRefGoogle Scholar
  12. 12.
    Tomita K, Koda S, Oshima Y (2002) Catalytic hydration of propylene with MoO3/Al2O3 in supercritical water. Ind Eng Chem Res 41:3341–3344CrossRefGoogle Scholar
  13. 13.
    Watanabe M, Aizawa Y, Iida T, Aida TM, Levy C, Sue K, Inomata H (2005) Glucose reactions with acid and base catalysts in hot compressed water at 473 K. Carbohydr Res 340:1925–1930CrossRefGoogle Scholar
  14. 14.
    Qi X, Watanabe M, Aida TM, Smith RL Jr (2008) Catalytical conversion of fructose and glucose into 5-hydroxymethylfurfural in hot compressed water by microwave heating. Catal Commun 9:2244–2249CrossRefGoogle Scholar
  15. 15.
    Nakajima K, Baba Y, Noma R, Kitano M, Kondo JN, Hayashi S, Hara M (2011) Nb2O5·nH2O as a heterogeneous catalyst with water-tolerant lewis acid sites. J Am Chem Soc 133:4224–4227CrossRefGoogle Scholar
  16. 16.
    Bühler W, Dinjus E, Ederer EJ, Kruse A, Mas C (2002) Ionic reactions and pyrolysis of glycerol as competing reaction pathways in near- and supercritical water. J Supercrit Fluids 22:37–53CrossRefGoogle Scholar
  17. 17.
    Watanabe M, Inomata H, Osada M, Sato T, Adschiri T, Arai K (2003) Catalytic effects of NaOH and ZrO2 for partial oxidative gasification of n-hexadecane and lignin in supercritical water. Fuel 82:545–552CrossRefGoogle Scholar
  18. 18.
    Yoshida T, Oshima Y (2004) Partial oxidative and catalytic biomass gasification in supercritical water: a promising flow reactor system. Ind Eng Chem Res 43:4097–4104CrossRefGoogle Scholar
  19. 19.
  20. 20.
    Ohira H, Torii N, Aida TM, Watanabe M, Smith RL Jr (2009) Rapid separation of shikimic acid from Chinese star anise (Illicium verum Hook. f.) with hot water extraction. Sep Purif Technol 69:102–108CrossRefGoogle Scholar
  21. 21.
    Titirici MM, Thomas A, Antonietti M (2007) Back in the black: hydrothermal carbonization of plant material as an efficient chemical process to treat the CO2 problem? New J Chem 31:787–789CrossRefGoogle Scholar
  22. 22.
    Hu B, Wang K, Wu L, Yu SH, Antonietti M, Titirici MM (2010) Engineering carbon materials from the hydrothermal carbonization process of biomass. Adv Mater 22:813–828Google Scholar
  23. 23.
    Wang Q, Li H, Chen L, Huang X (2001) Monodispersed hard spherules with uniform nanopores. Carbon 39:2211–2214CrossRefGoogle Scholar
  24. 24.
    Yao C, Shin Y, Wang LQ, Windisch W Jr, Samuels WD, Arey BW, Wang C, Risen WM Jr, Exarhos GJ (2007) Hydrothermal dehydration of aqueous fructose solutions in a closed system. J Phys Chem C 111:15141–15145CrossRefGoogle Scholar
  25. 25.
    Mi Y, Hu W, Dan Y, Liu Y (2008) Synthesis of carbon micro-spheres by a glucose hydrothermal method. Mater Lett 62:1194–1196CrossRefGoogle Scholar
  26. 26.
    Baccile N, Laurent G, Babonneau F, Fayon F, Titirici MM, Antonietti M (2009) Structural characterization of hydrothermal carbon spheres by advanced solid-state MAS 13C NMR investigation. J Phys Chem C 113:9644–9654CrossRefGoogle Scholar
  27. 27.
    Sevilla M, Fuertes AB (2009) Chemical and structural properties of carbonaceous products obtained by hydrothermal carbonization of saccharides. Chem Eur J 15:4195–4203CrossRefGoogle Scholar
  28. 28.
    Shin Y, Wang LQ, Bae IT, Arey BW, Exarhos GJ (2008) Hydrothermal syntheses of colloidal carbon spheres from cyclodextrins. J Phys Chem C 112:14236–14240CrossRefGoogle Scholar
  29. 29.
    Sevilla M, Fuertes AB (2009) The production of carbon materials by hydrothermal carbonization of cellulose. Carbon 47:2281–2289CrossRefGoogle Scholar
  30. 30.
    Titirici MM, Thomas A, Yu SH, Mueller JO, Antonietti M (2007) A direct synthesis of mesoporous carbons with bicontinuous pore morphology from crude plant material by hydrothermal carbonization. Chem Mater 19:4205–4212CrossRefGoogle Scholar
  31. 31.
    Heilmann SM, Jader LR, Sadowsky MJ, Schendel FJ, von Keitz MG, Valentas KJ (2011) Hydrothermal carbonization of distiller’s grains. Biomass Bioenerg 35:2526–2533CrossRefGoogle Scholar
  32. 32.
    Falco C, Caballero FP, Babonneau F, Gervais C, Laurent G, Titirici MM, Baccile N (2011) Hydrothermal carbon from biomass: structural differences between hydrothermal and pyrolyzed carbon via 13C solid state NMR. Langmuir 27:14460–14471Google Scholar
  33. 33.
    Heilmann SM, Davis HT, Jader LR, Lefebvre PA, Sadowsky MJ, Schendel FJ, von Keitz MG, Valentas KJ (2010) Hydrothermal carbonization of microalgae. Biomass Bioenerg 34:875–882CrossRefGoogle Scholar
  34. 34.
    Sevilla M, Macia-Agullo JA, Fuertes AB (2011) Hydrothermal carbonization of biomass as a route for sequenstration of CO2: chemical and structural properties of the carbonized products. Biomass Bioenerg 35:3152–3159CrossRefGoogle Scholar
  35. 35.
    Paraknowitsch JP, Thomas A, Antonietti M (2009) Carbon colloids prepared by hydrothermal carbonization as efficient fuels for indirect carbon fuel cells. Chem Mater 21:1170–1172CrossRefGoogle Scholar
  36. 36.
    Demir-Cakan R, Baccile N, Antonietti M, Titirici MM (2009) Carboxylate-rich carbonaceous materials via one-step hydrothermal carbonization of glucose in the presence of acrylic acid. Chem Mater 21:484–490CrossRefGoogle Scholar
  37. 37.
    Demir-Cakan R, Makowski P, Antonietti M, Goettmann F, Titirici MM (2010) Hydrothermal synthesis of imidazole functionalized carbon spheres and their application in catalyst. Catal Today 150:115–118CrossRefGoogle Scholar
  38. 38.
    Xiao H, Guo Y, Liang X, Qi C (2010) One-step synthesis of novel biacidic carbon via hydrothermal carbonization. J Solid State Chem 183:1721–1725CrossRefGoogle Scholar
  39. 39.
    Sun X, Li Y (2004) Colloidal spheres and their core/shell structures with noble-metal nanoparticles. Angew Chem Int Ed 43:597–601CrossRefGoogle Scholar
  40. 40.
    Yu SH, Cui X, Li L, Li K, Yu B, Antonietti M, Coelfen H (2004) From starch to metal/carbon hybrid nanostructures: hydrothermal metal-catalyzed carbonization. Adv Mater 16:1636–1640CrossRefGoogle Scholar
  41. 41.
    Qian HS, Yu SH, Luo LB, Gong JY, Fei LF, Liu XM (2006) Synthesis of uniform Te@carbon –rich composite nanocables with photoluminescence properties and carbonaceous nanofibers by the hydrothermal carbonization of glucose. Chem Mater 18:2102–2108CrossRefGoogle Scholar
  42. 42.
    Cui X, Antonietti M, Yu SH (2006) Structural effects of iron oxide nanoparticles and iron ions on the hydrothermal carbonization of starch and rice carbohydrates. Small 2:756–759CrossRefGoogle Scholar
  43. 43.
    Titirici MM, Antonietti M, Thomas A (2006) A generalized synthesis of metal oxide hollow spheres using hydrothermal approach. Chem Mater 18:3808–3812CrossRefGoogle Scholar
  44. 44.
    Yu J, Yu X (2008) Hydrothermal synthesis and photocatalytic activity of zinc oxide hollow spheres. Environ Sci Technol 42:4902–4907CrossRefGoogle Scholar
  45. 45.
  46. 46.
  47. 47.
  48. 48.
    Qi X, Watanabe M, Aida TM, Smith RL Jr (2008) Catalytic dehydration of fructose into 5-hydroxymethylfurfural byion-exchange resin in mixed-aqueous system by microwave heating. Green Chem 10:799–805CrossRefGoogle Scholar
  49. 49.
    Yan X, Jin F, Tohji K, Moriya T, Enomoto H (2007) Production of lactic acid from glucose by alkaline hydrothermal reaction. J Mater Sci 42:9995–9999CrossRefGoogle Scholar
  50. 50.
    Kishida H, Jin F, Zhou Z, Moriya T, Enomoto H (2005) Conversion of glycerin into lactic acid by alkaline hydrothermal reaction. Chem Lett 34:1560–1561CrossRefGoogle Scholar
  51. 51.
    Shen Z, Jin F, Zhang Y, Wu B, Kishita A, Tohji K, Kishida H (2009) Effect of alkaline catalysts on hydrothermal conversion of glycerin into lactic acid. Ind Eng Chem Res 48:8920–8925CrossRefGoogle Scholar
  52. 52.
    Jin F, Yun J, Li GM, Kishita A, Tohji K, Enomoto H (2008) Hydrothermal conversion of carbohydrate biomass into formic acid at mild temperatures. Green Chem 10:612–615CrossRefGoogle Scholar
  53. 53.
    Aida TM, Yamagata T, Watanabe M, Smith RL Jr (2010) Depolymerization of sodium alginate under hydrothermal conditions. Carbohydr Polym 80:296–302CrossRefGoogle Scholar
  54. 54.
    Aida TM, Yamagata T, Abe C, Kawanami H, Watanabe M, Smith RL Jr (2012) Production of organic acids from alginate in high temperature water. J Supercrit Fluids 65:39–44CrossRefGoogle Scholar
  55. 55.
    Watanabe M, Iida T, Aizawa Y, Aida TM, Inomata H (2007) Acrolein synthesis from glycerol in hot-compressed water. Bioresour Technol 98:1285–1290CrossRefGoogle Scholar
  56. 56.
    Saisu M, Sato T, Watanabe M, Adschiri T, Arai K (2003) Conversion of lignin with supercritical water-phenol mixtures. Energy Fuels 17:922–928CrossRefGoogle Scholar
  57. 57.
    Okuda K, Man X, Umetsu M, Takami S, Adschiri T (2004) Efficient conversion of lignin into single chemical species by solvothermal reaction in water-p-cresol solvent. J Phys: Condens Matter 16:S1325–S1330Google Scholar
  58. 58.
    Okuda K, Umetsu M, Takami S, Adschiri T (2004) Disassembly of lignin and chemical recovery—rapid depolymerization of lignin without char formation in water–phenol mixtures. Fuel Process Technol 85:803–813CrossRefGoogle Scholar
  59. 59.
    Peterson AP, Vogel F, Lachance RP, Froling M, Antal MJ Jr, Tester JW (2008) Thermochemical biofuel production in hydrothermal media: A review of sub- and supercritical water technologies. Energy Environ Sci 1:32–65CrossRefGoogle Scholar
  60. 60.
    Osada M, Sato T, Watanabe M, Shirai M, Arai K (2006) Catalytic gasification of wood biomass in subcritical and supercritical water. Combust Sci Tech 178:537–552CrossRefGoogle Scholar
  61. 61.
    Watanabe M, Aida TM, Smith RL Jr, Inomata H (2012) Hydrogen Formation from Biomass Model Compounds and Real Biomass by Partial Oxidation in High Temperature High Pressure Water. J Jpn Petrol Inst 55:219–228CrossRefGoogle Scholar
  62. 62.
    Watanabe M, Qi X, Aida TM, Smith RL Jr (2012) Microwave apparatus for kinetic studies and in situ observations in hydrothermalor high-pressure ionic liquid system. In: The Development and application of microwave heating, InTech, 2012. http://dx.doi.org/10.5772/45625
  63. 63.
    Lecomte J, Finiels A, Moreau C (2002) Kinetic study of the isomerization of glucose into fructose in the presence of anion-modified hydrotalcites. Starch 54 (2002):75–79Google Scholar
  64. 64.
    Souza ROL, Fabiano DP, Feche C, Rataboul F, Cardoso D, Essayem N (2012) Glucose–fructose isomerisation promoted by basic hybrid catalysts. Catal Today 195:114–119CrossRefGoogle Scholar
  65. 65.
    Dinjus E, Kruse A, Troger N (2011) Hydrothermal carbonization 1. Influence of lignin in lignocelluloses. Chem Eng Technol 34:2037–2043CrossRefGoogle Scholar
  66. 66.
    Titirici MM, White RJ, Falco C, Sevilla M (2012) Black perspectives for a green future: hydrothermal carbons for environment protection and energy storage. Energy Environ Sci 5:6796–6822CrossRefGoogle Scholar
  67. 67.
    Rahmani S, McCaffrey W, Elliott JA, Gray MR (2003) Liquid-phase behavior during the cracking of asphaltenes. Ind Eng Chem Res 42:4101–4108CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 2014

Authors and Affiliations

  • Masaru Watanabe
    • 1
    • 2
    Email author
  • Taku M. Aida
    • 2
  • Richard Lee Smith
    • 1
    • 2
  1. 1.Research Center of Supercritical Fluid TechnologyTohoku UniversitySendaiJapan
  2. 2.Department of Environmental StudyTohoku UniversitySendaiJapan

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