Abstract
Cyclodextrins (CDs) and deep eutectic solvents (DESs) are emerging absorbent materials for the removal of volatile organic compounds (VOCs). In this study, we have used combination of modified CDs and levulinic acid to form four DESs analogs, referred to as supramolecular low-melting mixtures (LMMs), to study their absorption characteristics towards five VOCs, namely acetaldehyde, butanone, dichloromethane, thiophene, and toluene. The supramolecular LMMs showed up to 250-fold reduction in the vapor-liquid partition coefficients compared to water. The overall absorption capacity found to be synergistic and seemed to be dictated by the hydrophobicity of the VOCs. Toluene and dichloromethane were absorbed at 99 and 95% by the supramolecular LMMs, respectively, even at higher concentrations, with a linear relationship between the concentration and absorption capacity. The LMMs also retained their absorption capacities even after five absorption/desorption cycles.
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References
Abbott AP, Capper G, Davies DL, Rasheed RK, Tambyrajah V (2003) Novel solvent properties of choline chloride/urea mixtures. Chem Commun 70–71. https://doi.org/10.1039/b210714g
Berenjian A, Chan N, Malmiri HJ (2012) Volatile organic compounds removal methods: a review. Am J Biochem Biotechnol 8:220–229. https://doi.org/10.3844/ajbbsp.2012.220.229
Blach P, Fourmentin S, Landy D, Cazier F, Surpateanu G (2008) Cyclodextrins: a new efficient absorbent to treat waste gas streams. Chemosphere 70:374–380. https://doi.org/10.1016/j.chemosphere.2007.07.018
Chen C-C, Huang Y-H, Hung S-M, Chen C, Lin CW, Yang HH (2021) Hydrophobic deep eutectic solvents as attractive media for low-concentration hydrophobic VOC capture. Chem Eng J 424:130420. https://doi.org/10.1016/j.cej.2021.130420
Crini G (2014) Review : a history of cyclodextrins. Chem Rev 114:10940–10975. https://doi.org/10.1021/cr500081p
Decock G, Landy D, Surpateanu G, Fourmentin S (2008) Study of the retention of aroma components by cyclodextrins by static headspace gas chromatography. J Incl Phenom Macrocycl Chem 62:297–302. https://doi.org/10.1007/s10847-008-9471-z
Di Pietro ME, Colombo Dugoni G, Ferro M et al (2019) Do cyclodextrins encapsulate volatiles in deep eutectic systems? ACS Sustain Chem Eng 7:17397–17405. https://doi.org/10.1021/acssuschemeng.9b04526
El Achkar T, Fourmentin S, Greige-gerges H (2019) Deep eutectic solvents : an overview on their interactions with water and biochemical compounds. J Mol Liq 288:111028. https://doi.org/10.1016/j.molliq.2019.111028
El Achkar T, Moufawad T, Ruellan S et al (2020a) Cyclodextrins: from solute to solvent. Chem Commun 56:3385–3388. https://doi.org/10.1039/d0cc00460j
El Achkar T, Moura L, Moufawad T et al (2020b) New generation of supramolecular mixtures: characterization and solubilization studies. Int J Pharm 584:119443. https://doi.org/10.1016/j.ijpharm.2020.119443
Fahri F, Bacha K, Chiki FF, Mbakidi JP, Panda S, Bouquillon S, Fourmentin S (2020) Air pollution: new bio-based ionic liquids absorb both hydrophobic and hydrophilic volatile organic compounds with high efficiency. Environ Chem Lett 18:1403–1411. https://doi.org/10.1007/s10311-020-01007-8
Fourmentin S, Ciobanu A, Landy D, Wenz G (2013) Space filling of β-cyclodextrin and β-cyclodextrin derivatives by volatile hydrophobic guests. Beilstein J Org Chem 9:1185–1191. https://doi.org/10.3762/bjoc.9.133
Fourmentin S, Outirite M, Blach P, Landy D, Ponchel A, Monflier E, Surpateanu G (2007) Solubilisation of chlorinated solvents by cyclodextrin derivatives. A study by static headspace gas chromatography and molecular modelling. J Hazard Mater 141:92–97. https://doi.org/10.1016/j.jhazmat.2006.06.090
Francisco M, van den Bruinhorst A, Kroon MC et al (2013) Low-transition-temperature mixtures (LTTMs): a new generation of designer solvents. Angew Chem Int Ed 52:3074–3085. https://doi.org/10.1002/anie.201207548
He C, Zhuo M, Hou J (2021) Efficient purification of toluene gas by anoxic denitrification. Environ Sci Pollut Res 28:11683–11688. https://doi.org/10.1007/s11356-020-12311-9
Kfoury M, Landy D, Fourmentin S (2018) Characterization of cyclodextrin/volatile inclusion complexes: a review. Molecules 23:1204. https://doi.org/10.3390/molecules23051204
Khan FI, Ghoshal AK (2000) Removal of volatile organic compounds from polluted air. J Loss Prev Process Ind 13:527–545. https://doi.org/10.1016/S0950-4230(00)00007-3
Kolb B, Ettre LS (2006) Chromatography: theory and Practice, 2nd edn. Wiley
Kumari P, Singh P, Singhal AA (2020) Cyclodextrin-based nanostructured materials for sustainable water remediation applications. Environ Sci Pollut Res 27:32432–32448. https://doi.org/10.1007/s11356-020-09519-0
Landy D, Mallard I, Ponchel A, Monflier E, Fourmentin S (2012) Remediation technologies using cyclodextrins: an overview. Environ Chem Lett 10:225–237. https://doi.org/10.1007/s10311-011-0351-1
Lannoy A, Kania N, Bleta R, Fourmentin S, Machut-Binkowski C, Monflier E, Ponchel A (2016) Photocatalysis of volatile organic compounds in water: towards a deeper understanding of the role of cyclodextrins in the photodegradation of toluene over titanium dioxide. J Colloid Interface Sci 461:317–325. https://doi.org/10.1016/j.jcis.2015.09.022
Lee Y-E, Chung W-C, Chang M-B (2019) Photocatalytic oxidation of toluene and isopropanol by LaFeO3/black-TiO2. Environ Sci Pollut Res 26:20908–20919. https://doi.org/10.1007/s11356-019-05436-z
Li Y, Chang H, Yan H, Tian S, Jessop PG (2021) Reversible absorption of volatile organic compounds by switchable-hydrophilicity solvents: a case study of toluene with N,N-dimethylcyclohexylamine. ACS Omega 6:253–264. https://doi.org/10.1021/acsomega.0c04443
Morin-Crini N, Fourmentin M, Fourmentin S, Torri G, Crini G (2019) Synthesis of silica materials containing cyclodextrin and their applications in wastewater treatment. Environ Chem Lett 17:683–696. https://doi.org/10.1007/s10311-018-00818-0
Moufawad T, Moura L, Ferreira M, Bricout H, Tilloy S, Monflier E, Costa Gomes M, Landy D, Fourmentin S (2019) First evidence of cyclodextrin inclusion complexes in a deep eutectic solvent. ACS Sustain Chem Eng 7:6345–6351. https://doi.org/10.1021/acssuschemeng.9b00044
Moura L, Moufawad T, Ferreira M, Bricout H, Tilloy S, Monflier E, Costa Gomes MF, Landy D, Fourmentin S (2017) Deep eutectic solvents as green absorbents of volatile organic pollutants. Environ Chem Lett 15:747–753. https://doi.org/10.1007/s10311-017-0654-y
Paiva A, Craveiro R, Aroso I, Martins M, Reis RL, Duarte ARC (2014) Natural deep eutectic solvents - solvents for the 21st century. ACS Sustain Chem Eng 2:1063–1071. https://doi.org/10.1021/sc500096j
Parmar GR, Rao NN (2009) Emerging control technologies for volatile organic compounds. Crit Rev Environ Sci Technol 39:41–78. https://doi.org/10.1080/10643380701413658
Quijano G, Couvert A, Amrane A, Darracq G, Couriol C, le Cloirec P, Paquin L, Carrié D (2011) Potential of ionic liquids for VOC absorption and biodegradation in multiphase systems. Chem Eng Sci 66:2707–2712. https://doi.org/10.1016/j.ces.2011.01.047
Raza N, Kim KH, Agbe H, Kailasa SK, Szulejko JE, Brown RJC (2017) Recent advances in titania-based composites for photocatalytic degradation of indoor volatile organic compounds. Asian J Atmos Environ 11:217–234. https://doi.org/10.5572/ajae.2017.11.4.217
Rodriguez Castillo AS, Biard PF, Guihéneuf S, Paquin L, Amrane A, Couvert A (2019) Assessment of VOC absorption in hydrophobic ionic liquids: measurement of partition and diffusion coefficients and simulation of a packed column. Chem Eng J 360:1416–1426. https://doi.org/10.1016/j.cej.2018.10.146
Rodriguez Rodriguez N, Van Den Bruinhorst A, Kollau LJBM et al (2019) Degradation of deep-eutectic solvents based on choline chloride and carboxylic acids. ACS Sustain Chem Eng 7:11521–11528. https://doi.org/10.1021/acssuschemeng.9b01378
Song Y, Chen S, Luo F, Sun L (2020) Absorption of toluene using deep eutectic solvents: quantum chemical calculations and experimental investigation. Ind Eng Chem Res 59:22605–22618. https://doi.org/10.1021/acs.iecr.0c04986
Supek E, Makoś P, Gȩbicki J, Rogala A (2019) Purification of model biogas from toluene using deep eutectic solvents. E3S Web Conf 116:00078. https://doi.org/10.1051/e3sconf/201911600078
Szaniszló N, Fenyvesi É, Balla J (2005) Structure-stability study of cyclodextrin complexes with selected volatile hydrocarbon contaminants of soils. J Incl Phenom 53:241–248. https://doi.org/10.1007/s10847-005-0245-6
Tandjaoui N, Wolbert D, Couvert A, Abouseoud M, Amrane A, Tassist A (2020) An effective toluene removal from waste-air by a simple process based on absorption in silicone oil (PDMS) and cross-linked Brassica rapa peroxidase (BRP-CLEAs) catalysis in organic medium: optimization with RSM. Environ Prog Sustain Energy 39:e13381. https://doi.org/10.1002/ep.13381
Xu R, Dai C, Mu M, Cheng J, Lei Z, Wu B, Liu N, Chen B, Yu G (2021) Highly efficient capture of odorous sulfur-based VOCs by ionic liquids. J Hazard Mater 402:123507. https://doi.org/10.1016/j.jhazmat.2020.123507
Yu G, Dai C, Gao H, Zhu R, du X, Lei Z (2018) Capturing condensable gases with ionic liquids. Ind Eng Chem Res 57:12202–12214. https://doi.org/10.1021/acs.iecr.8b02420
Yu G, Jiang Y, Cheng J, Lei Z (2019) Structural effect on the vapor-liquid equilibrium of toluene-ionic liquid systems. Chem Eng Sci 198:1–15. https://doi.org/10.1016/j.ces.2018.12.046
Yu G, Mu M, Li J, Wu B, Xu R, Liu N, Chen B, Dai C (2020) Imidazolium-based ionic liquids introduced into π-electron donors: highly efficient toluene capture. ACS Sustain Chem Eng 8:9058–9069. https://doi.org/10.1021/acssuschemeng.0c02273
Zhu L, Shen D, Luo KH (2020) A critical review on VOCs adsorption by different porous materials: species, mechanisms and modification methods. J Hazard Mater 389:122102
Acknowledgements
S.P. acknowledges the financial support from Université du Littoral-Côte d’Opale for his post-doctoral fellowship. Fatima Fahri and Tarek Moufawad are greatly acknowledged for their help in experiments.
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This research was supported by Université du Littoral Côte d’Opale.
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S.P.: Performed the experiments, analyzed and interpreted the data, and wrote the paper; S.F.: Conceived and designed the experiments, analyzed and interpreted the data, and wrote the paper.
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Panda, ., Fourmentin, S. Cyclodextrin-based supramolecular low melting mixtures: efficient absorbents for volatile organic compounds abatement. Environ Sci Pollut Res 29, 264–270 (2022). https://doi.org/10.1007/s11356-021-16279-y
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DOI: https://doi.org/10.1007/s11356-021-16279-y