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Application of Hydrothermal Reactions to Biomass Conversion pp 61–82Cite as

Hydrothermal Conversion of Lignin and Its Model Compounds into Formic Acid and Acetic Acid

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Part of the book series: Green Chemistry and Sustainable Technology ((GCST))

Abstract

With the fast depletion of fossil fuels, the development of effective approach for the production of value-added chemicals from renewable resources is strongly desired. Lignin is a main constituent of lignocellulosic biomass, which accounts for 15–30 % by weight and 40 % by energy. Therefore, lignin conversion has significant potential as a source for the sustainable production of chemicals and fuels. However, lignin has received little attention because of its highly crosslinked macromolecule structure and chemical properties. Hydrothermal technology has received much attention in the treatment of organic wastes and biomass conversion because of the unique inherent properties of high temperature water. Here, some recent studies on hydrothermal conversion of lignin and its model compounds into value-added chemicals such as formic acid and acetic acid are presented. Phenol and syringol are mainly introduced as lignin model compounds. It will be useful in exploring the potential approaches for the lignin conversion into useful chemicals and fuels.

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References

  1. Zakzeski J, Bruijnincx PC, Jongerius AL, Weckhuysen BM (2010) The catalytic valorization of lignin for the production of renewable chemicals. Chem Rev 110:3552–3599

    Article  Google Scholar 

  2. Kunkes EL, Simonetti DA, West RM, Serrano-Ruiz JC, Gartner CA, Dumesic JA (2008) Catalytic conversion of biomass to monofunctional hydrocarbons and targeted liquid-fuel classes. Science 322:417–421

    Article  Google Scholar 

  3. Chheda JN, Huber GW, Dumesic JA (2007) Liquid-phase catalytic processing of biomass-derived oxygenated hydrocarbons to fuels and chemicals. Angew Chem Int Ed 46:7164–7183

    Article  Google Scholar 

  4. Huber GW, Chheda J, Barrett CB, Dumesic JA (2005) Production of liquid alkanes by aqueous-phase processing of biomass-derived carbohydrates. Science 308:1446–1450

    Article  Google Scholar 

  5. Chheda JN, Huber GW, Dumesic JA (2004) Renewable alkanes by aqueous-phase reforming of biomass derived oxygenates. Angew Chem Int Ed 43:1549–1551

    Article  Google Scholar 

  6. Bond JQ, Alonso DM, Wang D, West RM, Dumesic JA (2010) Integrated catalytic conversion of g-valerolactone to liquid alkenes for transportation fuels. Science 327:1110–1114

    Article  Google Scholar 

  7. Garlson TP, Vispute TP, Huber GW (2008) Green gasoline by catalytic fast pyrolysis of solid biomass derived compounds. ChemSusChem 1:397–400

    Article  Google Scholar 

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

    Article  Google Scholar 

  9. Hendriks AT, Zeeman G (2007) Pretreatments to enhance the digestibility of lignocellulosic biomass. Bioresour Technol 100:10–18

    Article  Google Scholar 

  10. Effendi A, Gerhauser H, Bridgwater AV (2008) Production of renewable phenolic resins by thermochemical conversion of biomass: a review. Renew Sustain Energ Rev 12(8):2092–2116

    Article  Google Scholar 

  11. Lin SY, Dence CW (1992) Methods in lignin chemistry. Springer, Berlin

    Book  Google Scholar 

  12. Barbie J, Charon N, Dupassieux N (2012) Supercritical water biomass gasification process as a successful solution. Biomass Bioenergy 46:479–491

    Article  Google Scholar 

  13. Adler E (1977) Lignin—past, present and future. Wood Sci Technol 11:169–218

    Article  Google Scholar 

  14. Shaw RW, Brill YB, Clifford AA (1991) Supercritical water, a medium for chemistry. Chem Eng News 23:26–39

    Google Scholar 

  15. 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

    Google Scholar 

  16. Jin FM, Kishita A, Enomoto H (1999) Oxidation of garbage in supercritical water. Haikibutsu Gakkaishi 10:257–266 Japanese

    Article  Google Scholar 

  17. Girisuta A, Janssen LP, Heeres HJ (2006) A kinetic study on the conversion of glucose to levulinic acid. IChemE 84:339–349

    Article  Google Scholar 

  18. Akiya N, Savage PE (2002) Roles of water for chemical reaction in high-temperature water. Chem Rev 102:2725–2750

    Article  Google Scholar 

  19. Quintanilla A, Menéndez N, Tornero J, Casas JA, Rodríguez JJ (2008) Surface modification of carbon-supported iron catalyst during the wet air oxidation of phenol: influence on activity, selectivity and stability. Appl Catal B 81:105–114

    Article  Google Scholar 

  20. Wu Q, Hu X, Yue P (2003) Kinetics study on catalytic wet air oxidation of phenol. Chem Eng Sci 58:923–928

    Article  Google Scholar 

  21. Jin FM, Cao JX, Kishida H, Moriya T, Enomoto H (2007) Impact of phenolic compounds on hydrothermal oxidation of cellulose. Carbohydr Res 342:1129–1132

    Article  Google Scholar 

  22. Kolaczkowski ST, Beltran FJ, Mclurgh DB, Rivas FJ (1997) Wet air oxidation of phenol. Trans IChemE 75:257–265

    Article  Google Scholar 

  23. Wahyudiono A, Sasaki M, Goto M (2009) Conversion of biomass model compound under hydrothermal conditions using batch reactor. Fuel 88:1656–1664

    Article  Google Scholar 

  24. Lawson JR, Klein MT (1985) Influence of water on guaiacol pyrolysis. Ind Eng Chem Res 24:203–208

    Google Scholar 

  25. Gonzalez G, Salvado J, Montane D (2004) Reactions of vanillic acid in sub and supercritical water. J Supercrit Fluids 31:57–66

    Article  Google Scholar 

  26. Penninger JM, Kersten RJ, Baur HC (1999) Reactions of diphenylether in supercritical water e mechanism and kinetics. J Supercrit Fluids 16:119–132

    Article  Google Scholar 

  27. Jin FM, Zhou Z, Kishita A, Enomoto H, Kishida H, Moriya T (2007) A new hydrothermal process for producing acetic acid from biomass waste. Chem Eng Res Des 85(2):201–206

    Article  Google Scholar 

  28. Jin FM, Zhou Z, Moriya T, Kishida H, Higashijima H, Enomoto H (2005) Controlling hydrothermal reaction pathways to improve acetic acid production from carbohydrate biomass. Environ Sci Technol 39(6):1893–1902

    Article  Google Scholar 

  29. Jin FM, Kishita A, Moriya T, Enomoto H (2000) Kinetics of oxidation of food wastes with H2O2 in supercritical water. J Supercrit Fluids 19:251–262

    Article  Google Scholar 

  30. Jin FM, Yun J, Li GM, Kishita A, Tohji K, Enomoto H (2008) Hydrothermal conversion of carbohydrate biomass into formic acid at mild temperatures. Green Chem 10:612–615

    Article  Google Scholar 

  31. Jin FM, Cao JX, Kishida H, Moriya T, Enomoto H (2004) Effect of lignin on acetic acid production in wet oxidation of lignocellulosic wastes. Chem Lett 33(7):910–911

    Article  Google Scholar 

  32. Bang SS, Johnston D (1998) Environment effects of sodium acetate/formate deicer. Environ Contam Toxicol 35:580–587

    Article  Google Scholar 

  33. Palmer DA (1987) Formiates as alternatives deicers. Transp Res Rec 1127:34–36

    Google Scholar 

  34. Yu J, Savage PE (1998) Decomposition of formic acid under hydrothermal conditions. Ind Eng Chem Res 37:2–10

    Article  Google Scholar 

  35. Akiya N, Savage PE (1998) Role of water in formic acid decomposition. AIChE J 44:405–415

    Article  Google Scholar 

  36. Weber M, Wang JT, Wasmus S, Savinell RF (1996) Formic acid oxidation in a polymer electrolyte fuel cell. J Electrochem Soc 143:158–160

    Article  Google Scholar 

  37. Uhm S, Chung ST, Lee J (2008) Characterization of direct formic acid fuel cells by impedance studies. J Power Sources 178:34–43

    Article  Google Scholar 

  38. Rice C, Ha S, Masel RI, Waszczuk P, Wieckowski A, Barnard T (2002) Direct formic acid fuel cells. J Power Sources 111:83–89

    Article  Google Scholar 

  39. Jin FM, Kishita A, Moriya T, Enomoto H, Sato N (2002) A new process for producing Ca/Mg acetate deicer with Ca/Mg waste and acetic acid produced by wet oxidation of organic waste. Chem Lett 31(1):88–89

    Article  Google Scholar 

  40. Jin FM, Zhou Z, Moriya T, Kishda H, Higashijima H, Enomoto H (2005) Controlling hydrothermal reaction pathways to improve acetic acid production from carbohydrate biomass. Environ Sci Technol 39:1893–1902

    Article  Google Scholar 

  41. Lu M, Zeng X, Cao J, Huo Z, Jin FM (2011) Production of formic and acetic acids from phenol by hydrothermal oxidation. Res Chem Intermed 37:201–209

    Article  Google Scholar 

  42. Kojima Y, Fukuta T, Yamada T, Onyango MS, Bernardo EC, Matsuda H, Yagishita K (2005) Photolytic hydrogen peroxide oxidation of 2-chlorophenol waste water. Water Res 39:29–36

    Article  Google Scholar 

  43. Chang CJ, Li SS, Ko CM (1995) Catalytic wet oxidations of phenol- and p-chlorophenol-contaminated waters. J Chem Technol Biotechnol 64:245–252

    Article  Google Scholar 

  44. Martino CJ, Savage PE (1997) Reactions at supercritical conditions: applications and fundamentals. Ind Eng Chem Res 36:1391–1400

    Article  Google Scholar 

  45. Thornton TD, Savage PE (1990) Phenol oxidation in supercritical water. J Supercrit Fluids 3:240–248

    Article  Google Scholar 

  46. Joglekar HS, Samant SD, Joshi JB (1991) Kinetics of wet air oxidation of phenol and substituted phenols. Wat Res 25:135–145

    Article  Google Scholar 

  47. Portela JR, Nebot E, Delaossa EM (2001) Kinetic comparison between subcritical and supercritical water oxidation of phenol. Chem Eng J 81:287–299

    Article  Google Scholar 

  48. Suzuki H, Cao J, Jin FM, Kishita A, Enomoto H (2006) Wet oxidation of lignin model compounds and acetic acid production. J Mater Sci 41:1591–1597

    Article  Google Scholar 

  49. Zeng X, Jin FM, Cao JL, Yin GD, Zhang YL, Zhao JF (2010) Second international symposium on aqua science, water resource, and low carbon energy. AIP Conf Proc 1251:384–387

    Article  Google Scholar 

  50. Jin FM, Kishita A, Moriya T, Enomoto H (2000) Kinetics of oxidaiton of food wastes with H2O2 in supercritical water. J Supercrit Fluids 19:251–262

    Article  Google Scholar 

  51. Zeng X, Cao J, Jin FM, Huo ZB (2010) Production of formic acid and acetic acid from lignin by alkaline hydrothermal oxidation. In: The 2nd international solvothermal & hydrothermal association conference , 27 July 2010

    Google Scholar 

  52. Yan X, Jin FM, Enomoto H (2004) Use of biomass pyrolysis oils. In: 14th International Conference on the Properties of Water and Steam, pp 724–728

    Google Scholar 

  53. Shende RV, Levec J (2000) Subcritical aqueous-phase oxidation kinetics of acrylic, maleic, fumaric, and muconic acids. Ind Eng Chem Res 39:40–49

    Article  Google Scholar 

  54. Eftaxias J, Fonta A, Fortuny J, Giralt A, Fabregat F (2001) Kinetic modelling of catalytic wet air oxidation of phenol by simulated annealing. Appl Catal B 33:175–190

    Article  Google Scholar 

  55. Suzuki H, Cao J, Jin FM, Kishita A, Enomoto H (2004) Hydrothermal oxidation of lignin model compounds. In: Proceedings of 2nd international worship on water dynamics, Tohoku University, Sendai, Japan, pp 11–12

    Google Scholar 

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Acknowledgments

The authors gratefully acknowledge the financial support of the National Natural Science Foundation of China (No. 21277091 and No. 21077078), the National High Technology Research and Development Program of China (863 Program; No. 2009AA063903).

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Authors and Affiliations

  1. School of Environmental Science and Engineering, Shanghai Jiao Tong University, Shanghai, 200240, P.R. China

    Xu Zeng, Guodong Yao, Yuanqing Wang & Fangming Jin

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  1. Xu Zeng
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Correspondence to Fangming Jin .

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  1. School of Environmental Science & Engineering, Shanghai Jiao Tong University, Shanghai, China

    Fangming Jin

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Zeng, X., Yao, G., Wang, Y., Jin, F. (2014). Hydrothermal Conversion of Lignin and Its Model Compounds into Formic Acid and Acetic Acid. In: Jin, F. (eds) Application of Hydrothermal Reactions to Biomass Conversion. Green Chemistry and Sustainable Technology. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-54458-3_3

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  • DOI: https://doi.org/10.1007/978-3-642-54458-3_3

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  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-54457-6

  • Online ISBN: 978-3-642-54458-3

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