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Received October 26, 2024
Revised November 16, 2024
Accepted December 18, 2024
Available online May 1, 2025
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This is an Open-Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License (http://creativecommons.org/licenses/bync/3.0) which permits
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Liquid-Liquid Extractive De-aromatization of Toluene from n-hexane by Using Three Deep Eutectic Solvents (DES) in Two Different T- junction Geometries
Department of Chemical Engineering, MNNIT Allahabad 1Department of Chemical Engineering, Chandigarh University
msalam@mnnit.ac.in
Korean Chemical Engineering Research, May 2025, 63(2), 105108
https://doi.org/10.9713/kcer.2025.63.2.105108
https://doi.org/10.9713/kcer.2025.63.2.105108
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Abstract
In the present study, the extractive de-aromatization of hydrocarbons (i.e., toluene in n-hexane) was investigated using different deep eutectic solvents (DESs) in a multidimensional T-junction microchannel with diameters of 0.5 mm and 1 mm, respectively. Three different DESs were synthesized using ethylene glycol, triethylene glycol, and propionic acid as hydrogen bond donors (HBD) in combination with choline chloride, methyl triphenyl phosphonium bromide (MTPB), and tetrabutylammonium bromide (TBAB) as hydrogen bond acceptors (HBA). The effects of flow rate and channel diameter variation on slug volume were studied. The percentage removal of aromatics, slug volume, specific interfacial area, and volumetric mass transfer coefficient were investigated for the three different synthesized DESs. For the slug flow, the maximum slug length was in the range of 0.96-1.53 mm in the 1 mm T-junction and 0.481.02 mm in the 0.5 mm T-junction microchannel, obtained for a corresponding flow rate of 3.0-12.0 mL/min. The maximum interfacial area was in the range of 7315-7898 m2/m3 for the 0.5 mm T-junction and 2714-3053 m2/m3 for the 1 mm T-junction channel. The extraction efficiencies in slug flow ranged from 30.82% to 74.32%. Similarly, the volumetric mass transfer coefficients (kl,a) were estimated to be in the range of 0.018 to 0.113 s1. Comparing the various results obtained during the experimentation, it was found that better performance in both T-junction microchannels was achieved by the MTPB and TEG synthesized DES with a molar ratio of 1:6.
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30. Osundare, O. S., Falcone, G., Lao, L. Y. and Elliott, A., “Liquid– liquid Flow Pattern Prediction using Relevant Dimensionless Parameter Groups,” Energies, 13(17), 4355(2020).
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Eng. Process. Process. Intensif., 160, 108297(2021).
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33. Khatoon, B., Hasan, S. U. and Alam, M. S., “CO2 Capturing in Cross T-junction Microchannel using Numerical and Experimental Approach,” Chemical Papers, 77(10), 6319-6340(2023).
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38. Wasim, K., Chandra, A. K., Sachan, S. and Alam, M. S., “Effects of Channel Hydraulic Diameters and Flow Ratios of Two‐Phase Flow in Y-Junction Microchannels,” Chemical Engineering & Technology, 45(3), 535-542(2022).
39. Chen, Y. P., Liu, X. D. and Shi, M. H., “Hydrodynamics of Double Emulsion Droplet in Shear Flow,” Appl. Phys. Lett., 102(5), 051609(2013).
40. Liu, X. D., Wang, C. Y., Zhao, Y. J. and Chen, Y. P., “Passingover Motion During Binary Collision between Double Emulsion Droplets Under Shear,” Chem. Eng. Sci., 183, 215-222(2018).
41. Singh S. and Kumar, U. K. A., “Hydrodynamics and Mass Transfer Studies of Liquid-liquid Two-phase Flow in Parallel Microchannels,” International Journal of Multiphase Flow, 157, 104248 (2022).
42. Zhao, Y., Chen G. and Yuan, Q., “Liquid–Liquid Two-Phase Mass Transfer in the T-Junction Microchannels,”Wiley InterSc (2007).
43. Kumar, U. K. A. and Mohan, R., “Liquid-Liquid Extraction of Aromatic from Hydrocarbon Mixtures in Capillaries,” Brazilian Journal of Chemical Engineering, 35(2), (2018).
44. Naik, P. K., Kumar, N., Paul, N. and Banerjee, T., “Deep Eutectic Solvents in Liquid-Liquid Extraction,” Correlation and Molecular Dynamics Simulation (1st ed.). CRC Press (2022).
45. Bahia, P. V. B., Brandão, B. R. L. and Machado, M. E., “Deep Eutectic Solvent for the Extraction of Polycyclic Aromatic Compounds in Fuel, Food and Environmental Samples,” Talanta, 277, (2024).
2. Antony, R., Nandagopal, M. S. G., Sreekumar, N., Rangabhashiyam, S. and Selvaraju, N., “Liquid-liquid Slug Flow in a Microchannel Reactor and its Mass Transfer Properties - A Review,” Bulletin of Chem. Reaction Eng. & Cat., 9, 207-223(2014).
3. Assmann, N. and von Rohr, P. R., “Extraction in Microreactors: Intensification by Adding an Inert Gas Phase,” Chem. Eng. Process., 50, 822-827(2011).
4. Anastas, P. T. and Warner, J. C., “Green Chemistry: Theory and Practice”, Oxford University Press, New York (1998).
5. Rayaroth, M. P., Marchel, M. and Boczkaj, G., “Advanced Oxidation Processes for the Removal of Mono and Polycyclic Aromatic Hydrocarbons–A Review,”Science of The Total Environment,
857, 159043(2023).
6. Ayuso, M., Mateo, S., Belinchón, A., Navarro, P., Palomar, J., García, J. and Rodríguez, F., “Cyclic Carbonates as Solvents in the Dearomatization of Refinery Streams: Experimental Liquid– liquid Equilibria, Modelling, and Simulation,” Journal of Molecular Liquids, 380, 121710(2023).
7. Ofem, M. I., Ayi, C. A., Louis, H., Gber, T. E. and Ayi, A. A., “Influence of Anionic Species on the Molecular Structure, Nature of Bonding, Reactivity, and Stability of Ionic Liquids-based on 1butyl-3-methylimidazolium,” Journal of Molecular Liquids, 387, 122657(2023).
8. Navarro, P., de Dios-García, I., Larriba, M., Delgado-Mellado, N., Ayuso, M., Moreno, D., Palomar, J., García, J. and Rodríguez, F., “Dearomatization of Pyrolysis Gasoline by Extractive Distillation with 1-ethyl-3-Methylimidazolium Tricyanomethanide,” Fuel Processing Technology, 195, 106156(2019).
9. Navarro, P., Larriba, M., Delgado-Mellado, N., Ayuso, M., Romero, M., Garcia, J. and Rodriguez, F., “Experimental Screening Towards Developing Ionic Liquid-based Extractive Distillation in the Dearomatization of Refinery Streams”, Separation and Purification Technology, 201, 268-275(2018).
10. Kumar, N. and Banerjee, T., “Dearomatization Insights with Phosphonium-based Deep Eutectic Solvent: Liquid–liquid Equilibria Experiments and Predictions,” Journal of Chemical &
Engineering Data, 66(9), 3432-3442(2021).
11. Larriba, M., Navarro, P., González, E. J., García, J. and Rodríguez, F., “Dearomatization of pyrolysis gasolines from mild and severe cracking by liquid–liquid extraction using a binary mixture of [4empy] [Tf2N] and [emim][DCA] ionic liquids,” Fuel
Processing Technology, 137, 269-282(2015).
12. Bushra, K., Hasan, S. U. and Alam, M. S., “A Review of Frictional Pressure Drop Characteristics of Single Phase Microchannels Having Different Shapes of Cross Sections,” Chemical Product and Process Modelling 18(5), 701-739(2023).
13. Bushra, K., Hasan, S. U. and Alam, M. S., “Study of Mass Transfer Coefficient of CO2 Capture in Different Solvents using Microchannel: A Comparative Study,” In Computer Aided Chemical Engineering, 49, 691-696(2022).
14. Karande, R., Schmid, A. and Buehler, K., “Applications of Multiphasic Microreactors for Biocatalytic Reactions,”Org. Process Res.
Dev., 20(2), 361-370(2016).
15. Šalic, A, Tusék, A. and Zelic, B., “Application of Microreactors in Medicine and Biomedicine,” J. Appl. Biomed., 10(3), 137-153 (2012).
16. Gardeniers, H. J. G. E., Luttge, R., Berenschot, E. J. W., de Boer, M. J., Yeshurun, S. Y., Hefetz, M., van’t Oever, R. and van Den Berg, A., “Silicon Micromachined Hollow Microneedles for Transdermal Liquid Transport,” J. Microelectromechanical Syst., 12(6), 855862(2003).
17. Zanfir, M., Baldea, M. and Daoutidis, P., “Optimizing the Catalyst Distribution for Countercurrent Methane Steam Reforming in Plate Reactors,” AIChE J., 57(9), 2518-2528(2011).
18. Qian, J. Y., Li, X. J., Wu, Z., Jin, Z. J. and Sunden, B., “A Comprehensive Review on Liquid–liquid Two-phase Flow in Microchannel: Flow Pattern and Mass Transfer,”Microfluid. Nanofluid, 23(10), 1-30(2019).
19. Tsaoulidis, D., Dore, V., Angeli, P., Plechkova, N. V. and Seddon, K. R., “Dioxouranium [VI] Extraction in Microchannels using Ionic Liquids,” Chem. Eng. J., 227, 151-157(2013).
20. Taarji, N., Vodo, S., Bouhoute, M., Khalid, N., Hafidi, A., Kobayashi, I., Neves, M. A., Isoda, H. and Nakajima, M., “Preparation of Monodisperse O/W Emulsions using a Crude Surface-active Extract from Argan by-products in Microchannel Emulsification,” Colloids Surf. A Physicochem. Eng. Aspects, 585, 124050(2020).
21. Fan, C. X., Ma, R., Wang, Y. B. and Luo, J. H., “Demulsification of Oil-in-water Emulsions in a Novel Rotating Microchannel,” Ind. Eng. Chem. Res., 59(17), 8335-8345(2020).
22. Cheng, D. and Chen, F. E., “Experimental and Numerical Studies of the Phase-transfercatalyzed Wittig Reaction in Liquid–liquid Slug-flow Microchannels,” Ind. Eng.Chem. Res., 59(10), 43974410(2020).
23. Raimondi, N. D. M. and Prat, L., “Numerical Study of the Coupling between Reaction and Mass Transfer for Liquid–liquid Slug Flow in Square Microchannels,” AIChE J., 57(7), 1719-1732(2011).
24. Li, Y. H., Yamane, D. G., Li, S. N., Biswas, S., Reddy, R. K., Goettert, J. S., Nandakumar, K. and Kumar, C. S. S. R., “Geometric Optimization of Liquid–liquid Slug Flow in a Flowfocusing Millifluidic Device for Synthesis of Nanomaterials,” Chem.
Eng. J., 217, 447-459(2013).
25. Gómez-Pastora, J., González-Fernández, C., Fallanza, M., Bringas, E. and Ortiz, I., “Flow Patterns and Mass Transfer Performance of Miscible Liquid–liquid Flows in Various Microchannels: Numerical and Experimental Studies,” Chem. Eng. J., 344, 487497(2018).
26. Plouffe, P., Roberge, D. M., Sieber, J., Bittel, M. and Macchi, A., “Liquid–liquid Mass Transfer in a Serpentine Micro-reactor using Various Solvents,” Chem. Eng. J., 285, 605-615(2016).
27. Raimondi, N. D. M., Prat, L., Gourdon, C. and Tasselli, J., “Experiments of Mass Transfer with Liquid–liquid Slug Flow in Square Microchannels,” Chem. Eng. Sci., 105, 169-178(2014).
28. Kanizawa, F. T. and Ribatski, G., “Two-phase Flow Patterns and Pressure Drop Inside Horizontal Tubes Containing Twisted-tape Inserts,” Int. J. Multiph. Flow, 47, 50-65(2012).
29. Salim, A., Fourar, M., Pironon, J. and Sausse, J., “Oil–water Twophase Flow in Microchannels: Flow Patterns and Pressure Drop Measurements,” Can. J. Chem. Eng., 86(6), 978-988(2008).
30. Osundare, O. S., Falcone, G., Lao, L. Y. and Elliott, A., “Liquid– liquid Flow Pattern Prediction using Relevant Dimensionless Parameter Groups,” Energies, 13(17), 4355(2020).
31. Matsuoka, A. and Mae, K., “Design Strategy of a Microchannel Device for Liquid–liquid Extraction Based on the Relationship Between Mass Transfer Rate and Two-phase Flow Pattern,” Chem.
Eng. Process. Process. Intensif., 160, 108297(2021).
32. Verma, R. K. and Ghosh, S., “Effect of Phase Properties on Liquid– liquid Two-phase Flow Patterns and Pressure Drop in Serpentine Mini Geometry,” Chem. Eng. J., 397, 125443(2020).
33. Khatoon, B., Hasan, S. U. and Alam, M. S., “CO2 Capturing in Cross T-junction Microchannel using Numerical and Experimental Approach,” Chemical Papers, 77(10), 6319-6340(2023).
34. Darekar, M., Singh, K. K., Mukhopadhyay, S. and Shenoy, K. T., “Liquid–Liquid Two Phase Flow Patterns in Y-junction Microchannels,” Ind. Eng. Chem. Res., 56(42), 12215-12226(2017).
35. Zhao, Y. C., Su, Y. H., Chen, G. W. and Yuan, Q., “Effect of Surface Properties on the Flow Characteristics and Mass Transfer Performance in Microchannels,” Chem. Eng. Sci., 65(5), 15631570(2010).
36. Plouffe, P., Roberge, D. M. and Macchi, A., “Liquid–liquid Flow Regimes and Mass Transfer in Various Micro-reactors,” Chem.
Eng. J., 300, 9-19 (2016).
37. Kashid, M. and Kiwi-Minsker, L., “Quantitative Prediction of Flow Patterns in Liquid–liquid Flow in Micro-capillaries,” Chem. Eng.
Process. Process. Intensif., 50(10), 972-978(2011).
38. Wasim, K., Chandra, A. K., Sachan, S. and Alam, M. S., “Effects of Channel Hydraulic Diameters and Flow Ratios of Two‐Phase Flow in Y-Junction Microchannels,” Chemical Engineering & Technology, 45(3), 535-542(2022).
39. Chen, Y. P., Liu, X. D. and Shi, M. H., “Hydrodynamics of Double Emulsion Droplet in Shear Flow,” Appl. Phys. Lett., 102(5), 051609(2013).
40. Liu, X. D., Wang, C. Y., Zhao, Y. J. and Chen, Y. P., “Passingover Motion During Binary Collision between Double Emulsion Droplets Under Shear,” Chem. Eng. Sci., 183, 215-222(2018).
41. Singh S. and Kumar, U. K. A., “Hydrodynamics and Mass Transfer Studies of Liquid-liquid Two-phase Flow in Parallel Microchannels,” International Journal of Multiphase Flow, 157, 104248 (2022).
42. Zhao, Y., Chen G. and Yuan, Q., “Liquid–Liquid Two-Phase Mass Transfer in the T-Junction Microchannels,”Wiley InterSc (2007).
43. Kumar, U. K. A. and Mohan, R., “Liquid-Liquid Extraction of Aromatic from Hydrocarbon Mixtures in Capillaries,” Brazilian Journal of Chemical Engineering, 35(2), (2018).
44. Naik, P. K., Kumar, N., Paul, N. and Banerjee, T., “Deep Eutectic Solvents in Liquid-Liquid Extraction,” Correlation and Molecular Dynamics Simulation (1st ed.). CRC Press (2022).
45. Bahia, P. V. B., Brandão, B. R. L. and Machado, M. E., “Deep Eutectic Solvent for the Extraction of Polycyclic Aromatic Compounds in Fuel, Food and Environmental Samples,” Talanta, 277, (2024).
