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
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- Category:
- Articles
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- artykuły w czasopismach
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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
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- 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
- 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
- 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
- Persson, M.; Jonsson, O.; Wellinger, A. Biogas Upgrading To Vehicle Fuel Standards and Grid;
- ISBN IEA Bioenergy Task 37; IEA Bioenergy: London, UK, 2007. open in new tab
- 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.
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- Allegue, L.B.; Hinge, J. Biogas upgrading Evaluation of methods for H 2 S removal. Dan. Technol. Inst. 2014, 31.
- 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
- 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
- Ryckebosch, E.; Drouillon, M.; Vervaeren, H. Techniques for transformation of biogas to biomethane. Biomass Bioenergy 2011, 35, 1633-1645. [CrossRef] open in new tab
- Nordlander, E.; Holgersson, J.; Thorin, E.; Thomassen, M.; Yan, J. Energy Efficiency Evaluation of two Biogas Plants. Int. Conf. Appl. Energy 2011, 1661-1675.
- 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
- Rossi, F. A new geometry high performance small power MCFC. J. Fuel Cell Sci. Technol. 2004, 1-6. [CrossRef] open in new tab
- 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
- 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
- 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.
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- 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
- Lu, T.; Chen, F. Multiwfn: A multifunctional wavefunction analyzer. J. Comput. Chem. 2012, 33, 580-592. [CrossRef] [PubMed] open in new tab
- 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
- 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
- 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
- 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
- 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
- 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.
- 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.
- 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
- 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
- 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
- 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
- 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
- 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
- Minch, M.J. An Introduction to Hydrogen Bonding (Jeffrey, George A.). J. Chem. Educ. 1999, 76, 759. [CrossRef] open in new tab
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