Absorptive Desulfurization of Model Biogas Stream Using Choline Chloride-Based Deep Eutectic Solvents - Publication - Bridge of Knowledge

Search

Absorptive Desulfurization of Model Biogas Stream Using Choline Chloride-Based Deep Eutectic Solvents

Abstract

The paper presents a synthesis of deep eutectic solvents (DESs) based on choline chloride (ChCl) as hydrogen bond acceptor and phenol (Ph), glycol ethylene (EG), and levulinic acid (Lev) as hydrogen bond donors in 1:2 molar ratio. DESs were successfully used as absorption solvents for removal of dimethyl disulfide (DMDS) from model biogas steam. Several parameters affecting the absorption capacity and absorption rate have been optimized including kinds of DES, temperature, the volume of absorbent, model biogas flow rate, and initial concentration of DMDS. Furthermore, reusability and regeneration of DESs by means of adsorption and nitrogen barbotage followed by the mechanism of absorptive desulfurization by means of density functional theory (DFT) as well as FT-IR analysis were investigated. Experimental results indicate that the most promising DES for biogas purification is ChCl:Ph, due to high absorption capacity, relatively long absorption rate, and easy regeneration. The research on the absorption mechanism revealed that van der Waal interaction is the main driving force for DMDS removal from model biogas

Citations

  • 2 1

    CrossRef

  • 0

    Web of Science

  • 2 1

    Scopus

Cite as

Full text

download paper
downloaded 66 times
Publication version
Accepted or Published Version
License
Creative Commons: CC-BY open in new tab

Keywords

Details

Category:
Articles
Type:
artykuły w czasopismach
Published in:
Sustainability no. 12, pages 1 - 16,
ISSN:
Language:
English
Publication year:
2020
Bibliographic description:
Słupek E., Makoś P.: Absorptive Desulfurization of Model Biogas Stream Using Choline Chloride-Based Deep Eutectic Solvents// Sustainability -Vol. 12,iss. 4 (2020), s.1-16
DOI:
Digital Object Identifier (open in new tab) 10.3390/su12041619
Bibliography: test
  1. Guo, X.M.; Trably, E.; Latrille, E.; Carrre, H.; Steyer, J.P. Hydrogen production from agricultural waste by dark fermentation: A review. Int. J. Hydrogen Energy 2010, 35, 10660-10673. [CrossRef] open in new tab
  2. Słupek, E.; Makoś, P.; Kucharska, K.; Gębicki, J. Mesophilic and thermophilic dark fermentation course analysis using sensor matrices and chromatographic techniques. Chem. Pap. 2019, in press. open in new tab
  3. Bastidas-Oyanedel, J.R.; Bonk, F.; Thomsen, M.H.; Schmidt, J.E. Dark fermentation biorefinery in the present and future (bio)chemical industry. Rev. Environ. Sci. Biotechnol. 2015, 14, 473-498. [CrossRef] open in new tab
  4. Persson, M.; Jonsson, O.; Wellinger, A. Biogas Upgrading To Vehicle Fuel Standards and Grid;
  5. ISBN IEA Bioenergy Task 37; IEA Bioenergy: London, UK, 2007. open in new tab
  6. Andrés, C.; Guardia, A.D.; Couvert, A.; Wolbert, D.; Le, S.; Soutrel, I.; Nunes, G. Odor concentration (OC) prediction based on odor activity values (OAVs) during composting of solid wastes and digestates. Atmos. Environ. 2019, 201, 1-12.
  7. Papurello, D.; Soukoulis, C.; Schuhfried, E.; Cappellin, L.; Gasperi, F.; Silvestri, S.; Santarelli, M.; Biasioli, F. Monitoring of volatile compound emissions during dry anaerobic digestion of the Organic Fraction of Municipal Solid Waste by Proton Transfer Reaction Time-of-Flight Mass Spectrometry. Bioresour. Technol. 2012, 126, 254-265. [CrossRef] [PubMed] open in new tab
  8. Salazar Gómez, J.I.; Lohmann, H.; Krassowski, J. Determination of volatile organic compounds from biowaste and co-fermentation biogas plants by single-sorbent adsorption. Chemosphere 2016, 153, 48-57. [CrossRef] open in new tab
  9. Boczkaj, G.; Makoś, P.; Fernandes, A.; Przyjazny, A. New procedure for the control of the treatment of industrial effluents to remove volatile organosulfur compounds. J. Sep. Sci. 2016, 39. [CrossRef] open in new tab
  10. Makoś, P.; Boczkaj, G. Deep eutectic solvents based highly efficient extractive desulfurization of fuels-Eco-friendly approach. J. Mol. Liq. 2019, 111916. [CrossRef] open in new tab
  11. Andersson, F.A.T.; Karlsson, A.; Svensson, B.H.; Ejlertsson, J. Occurrence and abatement of volatile sulfur compounds during biogas production. J. Air Waste Manag. Assoc. 2004, 54, 855-861. [CrossRef] open in new tab
  12. Sarmad, S.; Mikkola, J.-P.; Ji, X. CO 2 capture with Ionic liquids (ILs) and Deep Eutectic Solvents (DESs): A new generation of sorbents. ChemSusChem 2016, 10, 324-352. [CrossRef] open in new tab
  13. Sevimoglu, O.; Tansel, B. Effect of persistent trace compounds in landfill gas on engine performance during energy recovery: A case study. Waste Manag. 2013, 33, 74-80. [CrossRef] [PubMed] open in new tab
  14. Sun, Q.; Li, H.; Yan, J.; Liu, L.; Yu, Z.; Yu, X. Selection of appropriate biogas upgrading technology-a review of biogas cleaning, upgrading and utilisation. Renew. Sustain. Energy Rev. 2015, 51, 521-532. [CrossRef] open in new tab
  15. Allegue, L.B.; Hinge, J. Biogas upgrading Evaluation of methods for H 2 S removal. Dan. Technol. Inst. 2014, 31.
  16. Mahmood, Q.; Zheng, P.; Cai, J.; Hayat, Y.; Hassan, M.J.; Wu, D.L.; Hu, B.L. Sources of sulfide in waste streams and current biotechnologies for its removal. J. Zhejiang Univ. Sci. A 2007, 8, 1126-1140. [CrossRef] open in new tab
  17. Burgess, J.E.; Parsons, S.A.; Stuetz, R.M. Developments in odour control and waste gas treatment biotechnology: A review. Biotechnol. Adv. 2001, 19, 35-63. [CrossRef] open in new tab
  18. Ryckebosch, E.; Drouillon, M.; Vervaeren, H. Techniques for transformation of biogas to biomethane. Biomass Bioenergy 2011, 35, 1633-1645. [CrossRef] open in new tab
  19. Nordlander, E.; Holgersson, J.; Thorin, E.; Thomassen, M.; Yan, J. Energy Efficiency Evaluation of two Biogas Plants. Int. Conf. Appl. Energy 2011, 1661-1675.
  20. Rossi, F.; Nicolini, A. A cylindrical Small Size Molten Carbonate Fuel Cell: Experimental Investigation on Materials and Improving Performance Solutions. Fuel Cells 2009, 9, 170-177. [CrossRef] open in new tab
  21. Rossi, F. A new geometry high performance small power MCFC. J. Fuel Cell Sci. Technol. 2004, 1-6. [CrossRef] open in new tab
  22. Tippayawong, N.; Thanompongchart, P. Biogas quality upgrade by simultaneous removal of CO 2 and H 2 S in a packed column reactor. Energy 2010, 35, 4531-4535. [CrossRef] open in new tab
  23. Noorain, R.; Kindaichi, T.; Ozaki, N.; Aoi, Y.; Ohashi, A. Biogas purification performance of new water scrubber packed with sponge carriers. J. Clean. Prod. 2019, 214, 103-111. [CrossRef] open in new tab
  24. Farooq, M.; Chaudhry, I.A.; Hussain, S.; Ramzan, N.; Ahmed, M. Biogas Up Gradation for Power Generation Applications in Pakistan. J. Qual. Technol. Manag. Vol. Viiiissue Ii 2012, VIII, 107-118.
  25. Wilk, A.; Więcław-Solny, L.; Tatarczuk, A.; Krótki, A.; Spietz, T.; Chwoła, T. Solvent selection for CO 2 capture from gases with high carbon dioxide concentration. Korean J. Chem. Eng. 2017, 34, 2275-2283. [CrossRef] open in new tab
  26. Xu, H.J.; Zhang, C.F.; Zheng, Z.S. Solubility of hydrogen sulfide and carbon dioxide in a solution of methyldiethanolamine mixed with ethylene glycol. Ind. Eng. Chem. Res. 2002, 41, 6175-6180. [CrossRef] open in new tab
  27. Romero, A.; Santos, A.; Tojo, J.; Rodríguez, A. Toxicity and biodegradability of imidazolium ionic liquids. J. Hazard. Mater. 2008, 151, 268-273. [CrossRef] [PubMed] open in new tab
  28. Makoś, P.; Słupek, E.; Gębicki, J. Hydrophobic deep eutectic solvents in microextraction techniques-A review. Microchem. J. 2020, 152, 104384. [CrossRef] open in new tab
  29. Zhang, Q.; De Oliveira Vigier, K.; Royer, S.; Jérôme, F. Deep eutectic solvents: Syntheses, properties and applications. Chem. Soc. Rev. 2012, 41, 7108-7146. [CrossRef] open in new tab
  30. Smink, D.; Kersten, S.R.A.; Schuur, B. Recovery of lignin from deep eutectic solvents by liquid-liquid extraction. Sep. Purif. Technol. 2019, 235, 116127. [CrossRef] open in new tab
  31. Florindo, C.; Branco, L.C.; Marrucho, I.M. Development of hydrophobic deep eutectic solvents for extraction of pesticides from aqueous environments. Fluid Phase Equilibria 2017, 448, 135-142. [CrossRef] open in new tab
  32. Zubeir, L.F.; Van Osch, D.J.G.P.; Rocha, M.A.A.; Banat, F.; Kroon, M.C. Carbon Dioxide Solubilities in Decanoic Acid-Based Hydrophobic Deep Eutectic Solvents. J. Chem. Eng. Data 2018, 63, 913-919. [CrossRef] open in new tab
  33. Pätzold, M.; Siebenhaller, S.; Kara, S.; Liese, A.; Syldatk, C.; Holtmann, D. Deep Eutectic Solvents as Efficient Solvents in Biocatalysis. Trends Biotechnol. 2019, 37, 943-959. [CrossRef] [PubMed] open in new tab
  34. Makoś, P.; Fernandes, A.; Przyjazny, A.; Boczkaj, G. Sample preparation procedure using extraction and derivatization of carboxylic acids from aqueous samples by means of deep eutectic solvents for gas chromatographic-mass spectrometric analysis. J. Chromatogr. A 2018, 1555, 10-19. [CrossRef] [PubMed] open in new tab
  35. Makoś, P.; Przyjazny, A.; Boczkaj, G. Hydrophobic deep eutectic solvents as "green" extraction media for polycyclic aromatic hydrocarbons in aqueous samples. J. Chromatogr. A 2018, 1570, 28-37. [CrossRef] [PubMed] open in new tab
  36. Sun, S.; Niu, Y.; Xu, Q.; Sun, Z.; Wei, X. Efficient SO 2 absorptions by four kinds of deep eutectic solvents based on choline chloride. Ind. Eng. Chem. Res. 2015, 54, 8019-8024. [CrossRef] open in new tab
  37. Yang, D.; Han, Y.; Qi, H.; Wang, Y.; Dai, S. Efficient Absorption of SO 2 by EmimCl-EG Deep Eutectic Solvents. ACS Sustain. Chem. Eng. 2017, 5, 6382-6386. [CrossRef] open in new tab
  38. Florindo, C.; Lima, F.; Branco, L.C.; Marrucho, I.M. Hydrophobic Deep Eutectic Solvents: A Circular Approach to Purify Water Contaminated with Ciprofloxacin. ACS Sustain. Chem. Eng. 2019, 7, 14739-14746. [CrossRef] open in new tab
  39. Moura, L.; Moufawad, T.; Ferreira, M.; Bricout, H.; Tilloy, S.; Monflier, E.; Costa Gomes, M.F.; Landy, D.; Fourmentin, S. Deep eutectic solvents as green absorbents of volatile organic pollutants. Environ. Chem. Lett. 2017, 15, 747-753. [CrossRef] open in new tab
  40. Słupek, E.; Makoś, P.; Gȩbicki, J.; Rogala, A. Purification of model biogas from toluene using deep eutectic solvents. E3s Web Conf. 2019, 116, 00078. open in new tab
  41. Ma, Y.; Wang, Q.; Zhu, T. Comparison of hydrophilic and hydrophobic deep eutectic solvents for pretreatment determination of sulfonamides from aqueous environments. Anal. Methods 2019, 11, 5901-5909. [CrossRef] open in new tab
  42. Florindo, C.; Oliveira, F.S.; Rebelo, L.P.N.; Fernandes, A.M.; Marrucho, I.M. Insights into the synthesis and properties of deep eutectic solvents based on cholinium chloride and carboxylic acids. ACS Sustain. Chem. Eng. 2014, 2, 2416-2425. [CrossRef] open in new tab
  43. Kalhor, P.; Ghandi, K. Deep eutectic solvents for pretreatment, extraction, and catalysis of biomass and food waste. Molecules 2019, 24, 4012. [CrossRef] [PubMed] open in new tab
  44. Simon, S.; Duran, M.; Dannenberg, J.J. How does basis set superposition error change the potential surfaces for hydrogen-bonded dimers? J. Chem. Phys. 1996, 105, 11024-11031. [CrossRef] open in new tab
  45. Johnson, E.R.; Keinan, S.; Mori-Sánchez, P.; Contreras-García, J.; Cohen, A.J.; Yang, W. Revealing noncovalent interactions. J. Am. Chem. Soc. 2010, 132, 6498-6506. [CrossRef] [PubMed] open in new tab
  46. Lu, T.; Chen, F. Quantitative analysis of molecular surface based on improved Marching Tetrahedra algorithm. J. Mol. Graph. Model. 2012, 38, 314-323. [CrossRef] [PubMed] open in new tab
  47. Lu, T.; Chen, F. Multiwfn: A multifunctional wavefunction analyzer. J. Comput. Chem. 2012, 33, 580-592. [CrossRef] [PubMed] open in new tab
  48. Noyola, A.; Morgan-sagastume, J.M.; Lo, J.E.; Ingenierı, I.D.; Escolar, C.; Universitaria, C.; Me, D.F. Treatment of biogas produced in anaerobic reactors for domestic wastewater: Odor control and energy/resource recovery. Rev. Environ. Sci. Bio. Technol. 2006, 51, 93-114. [CrossRef] open in new tab
  49. Ducom, G.; Radu-tirnoveanu, D.; Pascual, C.; Benadda, B.; Germain, P. Biogas-Municipal solid waste incinerator bottom ash interactions: Sulphur compounds removal. J. Hazard. Mater. 2009, 166, 1102-1108. [CrossRef] open in new tab
  50. Arespacochaga, N.D.; Valderrama, C.; Mesa, C.; Bouchy, L.; Cortina, J.L. Biogas deep clean-up based on adsorption technologies for Solid Oxide Fuel Cell applications. Chem. Eng. J. 2020, 255, 593-603. [CrossRef] open in new tab
  51. Privalova, E.; Rasi, S.; Mäki-Arvela, P.; Eränen, K.; Rintala, J.; Murzin, D.Y.; Mikkola, J.P. CO 2 capture from biogas: Absorbent selection. RSC Adv. 2013, 3, 2979-2994. [CrossRef] open in new tab
  52. Hsu, C.H.; Chu, H.; Cho, C.M. Absorption and reaction kinetics of amines and ammonia solutions with carbon dioxide in flue gas. J. Air Waste Manag. Assoc. 2003, 53, 246-252. [CrossRef] open in new tab
  53. Guo, Y.; Niu, Z.; Lin, W. Comparison of removal efficiencies of carbon dioxide between aqueous ammonia and NaOH solution in a fine spray column. Energy Procedia 2011, 4, 512-518.
  54. Gonzalez-Garza, D.; Rivera-Tinoco, R.; Bouallou, C. Comparison of ammonia, monoethanolamine, diethanolamine and methyldiethanolamine solvents to reduce CO 2 greenhouse gas emissions. Chem. Eng. Trans. 2009, 18, 279-284.
  55. Zhang, K.; Ren, S.; Yang, X.; Hou, Y.; Wu, W.; Bao, Y. Efficient absorption of low-concentration SO 2 in simulated flue gas by functional deep eutectic solvents based on imidazole and its derivatives. Chem. Eng. J. 2017, 327, 128-134. [CrossRef] open in new tab
  56. Lemus, J.; Bedia, J.; Moya, C.; Alonso-Morales, N.; Gilarranz, M.A.; Palomar, J.; Rodriguez, J.J. Ammonia capture from the gas phase by encapsulated ionic liquids (ENILs). RSC Adv. 2016, 6, 61650-61660. [CrossRef] open in new tab
  57. Meyer, M. Infrared, raman, microwave and ab initio study of dimethyl disulfide: Structure and force field. J. Mol. Struct. 1992, 273, 99-121. [CrossRef] open in new tab
  58. Biswal, H.S.; Chakraborty, S.; Wategaonkar, S. Experimental evidence of O-H-S hydrogen bonding in supersonic jet. J. Chem. Phys. 2008, 129. [CrossRef] open in new tab
  59. Biswal, H.S.; Wategaonkar, S. Sulfur, not too far behind O, N, and C: SH· · · π hydrogen bond. J. Phys. Chem. A 2009, 113, 12774-12782. [CrossRef] open in new tab
  60. Bhattacharyya, S.; Bhattacherjee, A.; Shirhatti, P.R.; Wategaonkar, S. O-H· · · S hydrogen bonds conform to the acid-base formalism. J. Phys. Chem. A 2013, 117, 8238-8250. [CrossRef] open in new tab
  61. Minch, M.J. An Introduction to Hydrogen Bonding (Jeffrey, George A.). J. Chem. Educ. 1999, 76, 759. [CrossRef] open in new tab
Verified by:
Gdańsk University of Technology

seen 263 times

Recommended for you

Meta Tags