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Hydrothermal liquefaction of protein-containing biomass: study of model compounds for Maillard reactions

  • Y. Fan
  • U. Hornung
  • N. Dahmen
  • A. Kruse
Original Article
  • 30 Downloads

Abstract

The potential application of bio-oil production from nitrogen-containing biomass via hydrothermal liquefaction (HTL) may be limited due to high nitrogen content, making this product oil unsuitable for fuel-related uses. The Maillard reaction is expected to play a most significant role in the interaction between proteins and carbohydrates during the hydrothermal treatment. To evaluate the Maillard reaction network in this process, lactose, maltose, and lysine were employed as model substances and tested individually and in binary mixtures. HTL experiments were conducted at temperatures between 250 and 350 °C and at 20 min reaction time. When treated individually, conversion of lysine leads to higher bio-oil yields (5–17 wt.%) than the model carbohydrates (6–10 wt.%) during HTL. In mixtures with carbohydrates, the measured bio-oil yields exceeded those obtained from conversion of the single substances (10–39 wt.%). Both yields and the relative nitrogen content of the bio-oil, increase with rising reaction temperature. The composition of the bio-oils obtained through HTL experiments was investigated in more detail: cyclopentenes and furfurals were obtained from disaccharide decomposition, piperidines and quinolines in the bio-oil originate from lysine, pyrazine and its derivatives are obtained from the mixture of lysine and disaccharides. A reaction scheme based on key chemical compounds accompanied with functional groups identified by FT-IR and NMR was developed to provide a better understanding of the Maillard reaction and its impact during HTL of protein-containing biomass.

Keywords

Hydrothermal liquefaction Bio-oil Nitrogen Maillard reactions 

Notes

Acknowledgements

Armin Lautenbach, Birgit Rolli, Alexandra Böhm, Jessica Mayer, and Sonja Habicht are thanked gratefully for their skillful technical assistance. Thomas Tietz and Matthias Pagel are thanked for the mechanical support. David Steinbach, Frederico Gomes Fonseca, and Muhammad Jamal Alhnidi are appreciated for the instructive suggestions.

Funding information

The authors gratefully acknowlege the financial support from the China Scholarship Council.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflict of interest.

Supplementary material

13399_2018_340_MOESM1_ESM.docx (107 kb)
ESM 1 (DOCX 106 kb)

References

  1. 1.
    Kruse A, Dahmen N (2015) Water—a magic solvent for biomass conversion. J Supercrit Fluids 96:36–45.  https://doi.org/10.1016/j.supflu.2014.09.038 CrossRefGoogle Scholar
  2. 2.
    Dimitriadis A, Bezergianni S (2017) Hydrothermal liquefaction of various biomass and waste feedstocks for biocrude production: a state of the art review. Renew Sust Energ Rev 68(Part 1):113–125.  https://doi.org/10.1016/j.rser.2016.09.120 CrossRefGoogle Scholar
  3. 3.
    Steinbach D, Kruse A, Sauer J (2017) Pretreatment technologies of lignocellulosic biomass in water in view of furfural and 5-hydroxymethylfurfural production- a review. Biomass Conversion Biorefinery 7(2):247–274.  https://doi.org/10.1007/s13399-017-0243-0 CrossRefGoogle Scholar
  4. 4.
    Kruse A, Dahmen N (2018) Hydrothermal biomass conversion: quo vadis? J Supercrit Fluids 134:114–123.  https://doi.org/10.1016/j.supflu.2017.12.035 CrossRefGoogle Scholar
  5. 5.
    Schuler J, Hornung U, Kruse A, Dahmen N, Sauer J (2017) Hydrothermal liquefaction of lignin. J Biomater Nanobiotechnol 08(01):96–108.  https://doi.org/10.4236/jbnb.2017.81007 CrossRefGoogle Scholar
  6. 6.
    Breunig M, Gebhart P, Hornung U, Kruse A, Dinjus E (2018) Direct liquefaction of lignin and lignin rich biomasses by heterogenic catalytic hydrogenolysis. Biomass Bioenergy 111:352–360.  https://doi.org/10.1016/j.biombioe.2017.06.001 CrossRefGoogle Scholar
  7. 7.
    López Barreiro D, Beck M, Hornung U, Ronsse F, Kruse A, Prins W (2015) Suitability of hydrothermal liquefaction as a conversion route to produce biofuels from macroalgae. Algal Res 11:234–241.  https://doi.org/10.1016/j.algal.2015.06.023 CrossRefGoogle Scholar
  8. 8.
    Ross AB, Biller P, Kubacki ML, Li H, Lea-Langton A, Jones JM (2010) Hydrothermal processing of microalgae using alkali and organic acids. Fuel 89(9):2234–2243.  https://doi.org/10.1016/j.fuel.2010.01.025 CrossRefGoogle Scholar
  9. 9.
    López Barreiro D, Gómez BR, Ronsse F, Hornung U, Kruse A, Prins W (2016) Heterogeneous catalytic upgrading of biocrude oil produced by hydrothermal liquefaction of microalgae: state of the art and own experiments. Fuel Process Technol 148:117–127.  https://doi.org/10.1016/j.fuproc.2016.02.034 CrossRefGoogle Scholar
  10. 10.
    Manara P, Zabaniotou A (2012) Towards sewage sludge based biofuels via thermochemical conversion – a review. Renew Sust Energ Rev 16(5):2566–2582.  https://doi.org/10.1016/j.rser.2012.01.074 CrossRefGoogle Scholar
  11. 11.
    Gong M, Zhu W, Xu ZR, Zhang HW, Yang HP (2014) Influence of sludge properties on the direct gasification of dewatered sewage sludge in supercritical water. Renew Energy 66:605–611.  https://doi.org/10.1016/j.renene.2014.01.006 CrossRefGoogle Scholar
  12. 12.
    Fan YJ, Zhu W, Gong M, Su Y, Zhang HW, Zeng JN (2016) Catalytic gasification of dewatered sewage sludge in supercritical water: influences of formic acid on hydrogen production. Int J Hydrog Energy 41(7):4366–4373.  https://doi.org/10.1016/j.ijhydene.2015.11.071 CrossRefGoogle Scholar
  13. 13.
    Pavlovič I, Knez Ž, Škerget M (2013) Hydrothermal reactions of agricultural and food processing wastes in sub- and supercritical water: a review of fundamentals, mechanisms, and state of research. J Agric Food Chem 61(34):8003–8025.  https://doi.org/10.1021/jf401008a CrossRefGoogle Scholar
  14. 14.
    Elliott DC, Biller P, Ross AB, Schmidt AJ, Jones SB (2015) Hydrothermal liquefaction of biomass: developments from batch to continuous process. Bioresour Technol 178:147–156.  https://doi.org/10.1016/j.biortech.2014.09.132 CrossRefGoogle Scholar
  15. 15.
    Amrullah A, Matsumura Y (2017) Supercritical water gasification of sewage sludge in continuous reactor. Bioresour Technol 249:276–283.  https://doi.org/10.1016/j.biortech.2017.10.002 CrossRefGoogle Scholar
  16. 16.
    Shanmugam SR, Adhikari S, Shakya R (2017) Nutrient removal and energy production from aqueous phase of bio-oil generated via hydrothermal liquefaction of algae. Bioresour Technol 230:43–48.  https://doi.org/10.1016/j.biortech.2017.01.031 CrossRefGoogle Scholar
  17. 17.
    Edmundson S, Huesemann M, Kruk R, Lemmon T, Billing J, Schmidt A, Anderson D (2017) Phosphorus and nitrogen recycle following algal bio-crude production via continuous hydrothermal liquefaction. Algal Res 26:415–421.  https://doi.org/10.1016/j.algal.2017.07.016 CrossRefGoogle Scholar
  18. 18.
    Saber M, Nakhshiniev B, Yoshikawa K (2016) A review of production and upgrading of algal bio-oil. Renew Sust Energ Rev 58:918–930.  https://doi.org/10.1016/j.rser.2015.12.342 CrossRefGoogle Scholar
  19. 19.
    Tang X, Zhang C, Li Z, Yang X (2016) Element and chemical compounds transfer in bio-crude from hydrothermal liquefaction of microalgae. Bioresour Technol 202:8–14.  https://doi.org/10.1016/j.biortech.2015.11.076 CrossRefGoogle Scholar
  20. 20.
    Jazrawi C, Biller P, He Y, Montoya A, Ross AB, Maschmeyer T, Haynes BS (2015) Two-stage hydrothermal liquefaction of a high-protein microalga. Algal Res 8:15–22.  https://doi.org/10.1016/j.algal.2014.12.010 CrossRefGoogle Scholar
  21. 21.
    Huang Y, Chen Y, Xie J, Liu H, Yin X, Wu C (2016) Bio-oil production from hydrothermal liquefaction of high-protein high-ash microalgae including wild Cyanobacteria sp. and cultivated Bacillariophyta sp. Fuel 183:9–19.  https://doi.org/10.1016/j.fuel.2016.06.013 CrossRefGoogle Scholar
  22. 22.
    Wang K, Brown RC (2013) Catalytic pyrolysis of microalgae for production of aromatics and ammonia. Green Chem 15(3):675.  https://doi.org/10.1039/c3gc00031a CrossRefGoogle Scholar
  23. 23.
    Dote Y, Hayashi T, Suzuki A, Ogi T (1992) Analysis of oil derived from liquefaction of sewage-sludge. Fuel 71(9):1071–1073.  https://doi.org/10.1016/0016-2361(92)90116-6 CrossRefGoogle Scholar
  24. 24.
    Inoue S, Sawayama S, Dote Y, Ogi T (1997) Behaviour of nitrogen during liquefaction of dewatered sewage sludge. Biomass Bioenergy 12(6):473–475.  https://doi.org/10.1016/S0961-9534(97)00017-2 CrossRefGoogle Scholar
  25. 25.
    Dote Y, Inoue S, Ogi T, S-y Y (1996) Studies on the direct liquefaction of protein-contained biomass: the distribution of nitrogen in the products. Biomass Bioenergy 11(6):491–498.  https://doi.org/10.1016/S0961-9534(96)00045-1 CrossRefGoogle Scholar
  26. 26.
    Dote Y, Inoue S, Ogi T, Yokoyama S-Y (1998) Distribution of nitrogen to oil products from liquefaction of amino acids. Bioresour Technol 64(2):157–160.  https://doi.org/10.1016/S0960-8524(97)00079-5 CrossRefGoogle Scholar
  27. 27.
    Kruse A, Krupka A, Schwarzkopf V, Gamard C, Henningsen T (2005) Influence of proteins on the hydrothermal gasification and liquefaction of biomass. 1. Comparison of different feedstocks. Ind Eng Chem Res 44(9):3013–3020.  https://doi.org/10.1021/ie049129y CrossRefGoogle Scholar
  28. 28.
    Kruse A, Maniam P, Spieler F (2007) Influence of proteins on the hydrothermal gasification and liquefaction of biomass. 2. Model compounds. Ind Eng Chem Res 46(1):87–96.  https://doi.org/10.1021/ie061047h CrossRefGoogle Scholar
  29. 29.
    Biller P, Johannsen I, dos Passos JS, Ottosen LDM (2018) Primary sewage sludge filtration using biomass filter aids and subsequent hydrothermal co-liquefaction. Water Res 130:58–68.  https://doi.org/10.1016/j.watres.2017.11.048 CrossRefGoogle Scholar
  30. 30.
    Brilman DWF, Drabik N, Wądrzyk M (2017) Hydrothermal co-liquefaction of microalgae, wood, and sugar beet pulp. Biomass Conversion Biorefinery 7(4):445–454.  https://doi.org/10.1007/s13399-017-0241-2 CrossRefGoogle Scholar
  31. 31.
    Zhang C, Tang X, Sheng L, Yang X (2016) Enhancing the performance of Co-hydrothermal liquefaction for mixed algae strains by the Maillard reaction. Green Chem 18(8):2542–2553.  https://doi.org/10.1039/c5gc02953h CrossRefGoogle Scholar
  32. 32.
    Ashoor SH, Zent JB (1984) Maillard browning of common amino acids and sugars. J Food Sci 49(4):1206–1207.  https://doi.org/10.1111/j.1365-2621.1984.tb10432.x CrossRefGoogle Scholar
  33. 33.
    Leiva GE, Naranjo GB, Malec LS (2017) A study of different indicators of Maillard reaction with whey proteins and different carbohydrates under adverse storage conditions. Food Chem 215:410–416.  https://doi.org/10.1016/j.foodchem.2016.08.003 CrossRefGoogle Scholar
  34. 34.
    Inoue S, Noguchi M, Hanaoka T, Minowa T (2004) Organic compounds formed by thermochemical degradation of glucose-glycine melanoidins using hot compressed water. J Chem Eng Jpn 37(7):915–919.  https://doi.org/10.1252/jcej.37.915 CrossRefGoogle Scholar
  35. 35.
    Peterson AA, Lachance RP, Tester JW (2010) Kinetic evidence of the Maillard reaction in hydrothermal biomass processing: glucose−glycine interactions in high-temperature, high-pressure water. Ind Eng Chem Res 49(5):2107–2117.  https://doi.org/10.1021/ie9014809 CrossRefGoogle Scholar
  36. 36.
    Teri G, Luo L, Savage PE (2014) Hydrothermal treatment of protein, polysaccharide, and lipids alone and in mixtures. Energy Fuel 28(12):7501–7509.  https://doi.org/10.1021/ef501760d CrossRefGoogle Scholar
  37. 37.
    Posmanik R, Cantero DA, Malkani A, Sills DL, Tester JW (2017) Biomass conversion to bio-oil using sub-critical water: study of model compounds for food processing waste. J Supercrit Fluids 119:26–35.  https://doi.org/10.1016/j.supflu.2016.09.004 CrossRefGoogle Scholar
  38. 38.
    Titirici M-M, Antonietti M, Baccile N (2008) Hydrothermal carbon from biomass: a comparison of the local structure from poly- to monosaccharides and pentoses/hexoses. Green Chem 10(11):1204–1212.  https://doi.org/10.1039/B807009A CrossRefGoogle Scholar
  39. 39.
    Minowa T, Inoue S, Hanaoka T, Matsumura Y (2004) Hydrothermal reaction of glucose and glycine as model compounds of biomass. J Jpn Inst Energy 83(10):794–798.  https://doi.org/10.3775/jie.83.794 CrossRefGoogle Scholar
  40. 40.
    Déniel M, Haarlemmer G, Roubaud A, Weiss-Hortala E, Fages J (2016) Energy valorisation of food processing residues and model compounds by hydrothermal liquefaction. Renew Sust Energ Rev 54(Supplement C):1632–1652.  https://doi.org/10.1016/j.rser.2015.10.017 CrossRefGoogle Scholar
  41. 41.
    Yaylayan VA (2003) Recent advances in the chemistry of Strecker degradation and Amadori rearrangement: implications to aroma and color formation. Food Sci Technol Res 9(1):1–6.  https://doi.org/10.3136/fstr.9.1 CrossRefGoogle Scholar
  42. 42.
    Van Lancker F, Adams A, De Kimpe N (2010) Formation of pyrazines in Maillard model systems of lysine-containing dipeptides. J Agric Food Chem 58(4):2470–2478.  https://doi.org/10.1021/jf903898t CrossRefGoogle Scholar
  43. 43.
    Remón J, Laseca M, García L, Arauzo J (2016) Hydrogen production from cheese whey by catalytic steam reforming: preliminary study using lactose as a model compound. Energy Convers Manag 114:122–141.  https://doi.org/10.1016/j.enconman.2016.02.009 CrossRefGoogle Scholar
  44. 44.
    Sınaǧ A, Kruse A, Schwarzkopf V (2003) Key compounds of the hydropyrolysis of glucose in supercritical water in the presence of K2CO3. Ind Eng Chem Res 42(15):3516–3521.  https://doi.org/10.1021/ie030079r CrossRefGoogle Scholar
  45. 45.
    Sınaǧ A, Kruse A, Rathert J (2004) Influence of the heating rate and the type of catalyst on the formation of key intermediates and on the generation of gases during hydropyrolysis of glucose in supercritical water in a batch reactor. Ind Eng Chem Res 43(2):502–508.  https://doi.org/10.1021/ie030475+ CrossRefGoogle Scholar
  46. 46.
    Ren D, Song Z, Li L, Liu Y, Jin F, Huo Z (2016) Production of 2,5-hexanedione and 3-methyl-2-cyclopenten-1-one from 5-hydroxymethylfurfural. Green Chem 18(10):3075–3081.  https://doi.org/10.1039/c5gc02493e CrossRefGoogle Scholar
  47. 47.
    Sheehan JD, Savage PE (2017) Molecular and lumped products from hydrothermal liquefaction of bovine serum albumin. ACS Sustain Chem Eng 5(11):10967–10975.  https://doi.org/10.1021/acssuschemeng.7b02854 CrossRefGoogle Scholar
  48. 48.
    Hwang H-I, Hartman TG, Rosen RT, Lech J, Ho C-T (1994) Formation of pyrazines from the Maillard reaction of glucose and lysine-.alpha.-amine-15N. J Agric Food Chem 42(4):1000–1004.  https://doi.org/10.1021/jf00040a031 CrossRefGoogle Scholar
  49. 49.
    Koehler PE, Odell GV (1970) Factors affecting the formation of pyrazine compounds in sugar-amine reactions. J Agric Food Chem 18(5):895–898.  https://doi.org/10.1021/jf60171a041 CrossRefGoogle Scholar

Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Karlsruhe Institute of Technology, Institute of Catalysis Research and Technology (IKFT)KarlsruheGermany
  2. 2.Conversion Technologies of Biobased Resources, Institute of Agricultural EngineeringUniversity of HohenheimStuttgartGermany

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