Liquid–liquid extraction of levulinic acid from aqueous solutions using hydrophobic tri-n-octylamine/alcohol-based deep eutectic solvent

doi:10.1016/j.cjche.2022.10.005

中国化学工程学报 ›› 2023, Vol. 54 ›› Issue (2): 248-256.DOI: 10.1016/j.cjche.2022.10.005

• Full Length Article • 上一篇下一篇

Liquid–liquid extraction of levulinic acid from aqueous solutions using hydrophobic tri-n-octylamine/alcohol-based deep eutectic solvent

Yinglin Mai¹, Xiaoling Xian¹, Lei Hu¹, Xiaodong Zhang¹, Xiaojie Zheng¹, Shunhui Tao¹, Xiaoqing Lin^1,2,3

1. School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou 510006, China;
2. Guangdong Provincial Key Laboratory of Plant Resources Biorefinery, Guangdong University of Technology, Guangzhou 510006, China;
3. Guangzhou Key Laboratory of Clean Transportation Energy Chemistry, Guangdong University of Technology, Guangzhou 510006, China

收稿日期:2022-05-27 修回日期:2022-10-15 出版日期:2023-02-28 发布日期:2023-05-11
通讯作者: Xiaoqing Lin,E-mail:linxiaoqing@gdut.edu.cn
基金资助:
This work was supported by the Key Area Research & Development Program of Guangdong Province (2020B0101070001), the National Natural Science Foundation of China (21978053, 51508547).

Liquid–liquid extraction of levulinic acid from aqueous solutions using hydrophobic tri-n-octylamine/alcohol-based deep eutectic solvent

Yinglin Mai¹, Xiaoling Xian¹, Lei Hu¹, Xiaodong Zhang¹, Xiaojie Zheng¹, Shunhui Tao¹, Xiaoqing Lin^1,2,3

1. School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou 510006, China;
2. Guangdong Provincial Key Laboratory of Plant Resources Biorefinery, Guangdong University of Technology, Guangzhou 510006, China;
3. Guangzhou Key Laboratory of Clean Transportation Energy Chemistry, Guangdong University of Technology, Guangzhou 510006, China

Received:2022-05-27 Revised:2022-10-15 Online:2023-02-28 Published:2023-05-11
Contact: Xiaoqing Lin,E-mail:linxiaoqing@gdut.edu.cn
Supported by:
This work was supported by the Key Area Research & Development Program of Guangdong Province (2020B0101070001), the National Natural Science Foundation of China (21978053, 51508547).

摘要/Abstract

摘要： Levulinic acid (LA) is one of the top-12 most promising biomass-based platform chemicals, which has a wide range of applications in a variety of fields. However, separation and purification of LA from aqueous solution or actual hydrolysate continues to be a challenge. Among various downstream separation technologies, liquid–liquid extraction is a low-cost, effective, and simple process to separate LA. The key breakthrough lies in the development of extractants with high extraction efficiency, good hydrophobicity, and low cost. In this work, three hydrophobic deep eutectic solvents (DESs) based on tri-n-octylamine (TOA) as hydrogen bond acceptor (HBA) and alcohols (butanol, 2-octanol, and menthol) as hydrogen bond donors (HBDs) were developed to extract LA from aqueous solution. The molar ratios of HBD and HBA, extraction temperature, contact time, solution pH, and initial LA concentration, DES/water volume ratios were systematically investigated. Compared with 2-octanol–TOA and menthol–TOA DES, the butanol–TOA DES exhibited the superior extraction performance for LA, with a maximum extraction efficiency of 95.79 ±1.4%. Moreover, the solution pH had a great impact on the LA extraction efficiency of butanol–TOA (molar ratio = 3:1). It is worth noting that the extraction equilibrium time was less than 0.5 h. More importantly, the butanol–TOA (3:1) DES possesses good extraction abilities for low, medium, and high concentrations of LA.

关键词: Extraction, Separation, Levulinic acid, Deep eutectic solvents, Hydrophobic, Aqueous solution

Abstract: Levulinic acid (LA) is one of the top-12 most promising biomass-based platform chemicals, which has a wide range of applications in a variety of fields. However, separation and purification of LA from aqueous solution or actual hydrolysate continues to be a challenge. Among various downstream separation technologies, liquid–liquid extraction is a low-cost, effective, and simple process to separate LA. The key breakthrough lies in the development of extractants with high extraction efficiency, good hydrophobicity, and low cost. In this work, three hydrophobic deep eutectic solvents (DESs) based on tri-n-octylamine (TOA) as hydrogen bond acceptor (HBA) and alcohols (butanol, 2-octanol, and menthol) as hydrogen bond donors (HBDs) were developed to extract LA from aqueous solution. The molar ratios of HBD and HBA, extraction temperature, contact time, solution pH, and initial LA concentration, DES/water volume ratios were systematically investigated. Compared with 2-octanol–TOA and menthol–TOA DES, the butanol–TOA DES exhibited the superior extraction performance for LA, with a maximum extraction efficiency of 95.79 ±1.4%. Moreover, the solution pH had a great impact on the LA extraction efficiency of butanol–TOA (molar ratio = 3:1). It is worth noting that the extraction equilibrium time was less than 0.5 h. More importantly, the butanol–TOA (3:1) DES possesses good extraction abilities for low, medium, and high concentrations of LA.

Key words: Extraction, Separation, Levulinic acid, Deep eutectic solvents, Hydrophobic, Aqueous solution

Yinglin Mai, Xiaoling Xian, Lei Hu, Xiaodong Zhang, Xiaojie Zheng, Shunhui Tao, Xiaoqing Lin. Liquid–liquid extraction of levulinic acid from aqueous solutions using hydrophobic tri-n-octylamine/alcohol-based deep eutectic solvent[J]. 中国化学工程学报, 2023, 54(2): 248-256.

参考文献

[1] F.D. Pileidis, M.M. Titirici, Levulinic acid biorefineries: New challenges for efficient utilization of biomass, ChemSusChem 9 (6) (2016) 562–582.
[2] T. Brouwer, M. Blahusiak, K. Babic, B. Schuur, Reactive extraction and recovery of levulinic acid, formic acid and furfural from aqueous solutions containing sulphuric acid, Sep. Purif. Technol. 185 (2017) 186–195.
[3] S. Dutta, I.K.M. Yu, J.J. Fan, J.H. Clark, D.C.W. Tsang, Critical factors for levulinic acid production from starch-rich food waste: Solvent effects, reaction pressure, and phase separation, Green Chem. 24 (1) (2022) 163–175.
[4] L.H. Qian, G.J. Lan, X.Y. Liu, Z.Q. Li, Y. Li, Aqueous-phase hydrogenation of levulinic acid over carbon layer protected silica-supported cobalt–ruthenium catalysts, Chin. J. Chem. Eng. 38 (2021) 114–122.
[5] F.H. Isikgor, C.R. Becer, Lignocellulosic biomass: A sustainable platform for the production of bio-based chemicals and polymers, Polym. Chem. 6 (25) (2015) 4497–4559.
[6] C.S. Zhou, X.J. Yu, H.L. Ma, R.H. He, S. Vittayapadung, Optimization on the conversion of bamboo shoot shell to levulinic acid with environmentally benign acidic ionic liquid and response surface analysis, Chin. J. Chem. Eng. 21 (5) (2013) 544–550.
[7] Prescient and Strategic Intelligence Private Limited, Levulinic Acid Market Size Poised to Surpass 34.5 USD million by 2024, https://www.globenewswire.com/news-release/2019/11/07/1942798/0/en/Levulinic-Acid-Market-Size-Poised-to-Surpass-345-Million-by-2024-P-S-Intelligence.html.
[8] Prescient and Strategic Intelligence Private Limited, Levulinic Acid Market, https://www.psmarketresearch.com/market-analysis/levulinic-acid-market.
[9] D.W. Rackemann, W.O. Doherty, The conversion of lignocellulosics to levulinic acid, Biofuel. Bioprod. Bior. 5 (2) (2011) 198–214.
[10] M. Sajid, U. Farooq, G. Bary, M.M. Azim, X.B. Zhao, Sustainable production of levulinic acid and its derivatives for fuel additives and chemicals: Progress, challenges, and prospects, Green Chem. 23 (23) (2021) 9198–9238.
[11] C. Chang, X.J. Ma, P.L. Cen, Kinetic studies on wheat straw hydrolysis to levulinic acid, Chin. J. Chem. Eng. 17 (5) (2009) 835–839.
[12] C. Chang, X.J. Ma, P.L. Cen, Kinetics of levulinic acid formation from glucose decomposition at high temperature, Chin. J. Chem. Eng. 14 (5) (2006) 708–712.
[13] E. Valentin, H.G. Nam, P.H. Kim, H.W. Joo, H.J. Shim, Y.K. Chang, S. Mun, Application of a Dowex-50WX8 chromatographic process to the preparative-scale separation of galactose, levulinic acid, and 5-hydroxymethylfurfural in acid hydrolysate of agarose, Sep. Purif. Technol. 133 (2014) 297–302.
[14] A. Senol, Extraction equilibria of formic and levulinic acids using Alamine 308/diluent and conventional solvent systems, Sep. Purif. Technol. 21 (1–2) (2000) 165–179.
[15] H. Park, J.W. Kim, K.B. Lee, S. Mun, Comparison of the process performances of a tandem 4-zone SMB and a single-cascade 5-zone SMB for separation of galactose, levulinic acid, and 5-hydroxymethylfurfural in agarose hydrolyzate, Sep. Purif. Technol. 237 (2020) 116357.
[16] Z.Q. Zhang, Y.F. Wu, L.J. Gao, G.M. Xiao, Pervaporation separation of levulinic acid aqueous solution by ZSM-5/PDMS composite membrane, J. Appl. Polym. Sci. 138 (1) (2021) 49611.
[17] H. Uslu, D. Datta, D. Santos, M. Öztürk, Separation of levulinic acid using polymeric resin, Amberlite IRA-67, J. Chem. Eng. Data 64 (7) (2019) 3044–3049.
[18] A. Kumar, D. Shende, K. Wasewar, Central composite design approach for optimization of levulinic acid separation by reactive components, Ind. Eng. Chem. Res. 60 (37) (2021) 13692–13700.
[19] J.F. Leal Silva, R. Maciel Filho, M.R. Wolf Maciel, Process design and technoeconomic assessment of the extraction of levulinic acid from biomass hydrolysate using n-butyl acetate, hexane, and 2-methyltetrahydrofuran, Ind. Eng. Chem. Res. 59 (23) (2020) 11031–11041.
[20] M.D. Pereira Santana, R. Belém Lavrador, P. de Alcântara Pessoa Filho, Solvent screening for liquid–liquid extraction of levulinic acid from aqueous medium, Sep. Sci. Technol. 57 (10) (2022) 1575–1584.
[21] P. Lenihan, A. Orozco, E. O’Neill, M.N.M. Ahmad, D.W. Rooney, G.M. Walker, Dilute acid hydrolysis of lignocellulosic biomass, Chem. Eng. J. 156 (2) (2010) 395–403.
[22] X.C. Liang, J.Y. Wang, Y.K. Guo, Z.G. Huang, H.T. Liu, High-efficiency recovery, regeneration and recycling of 1-ethyl-3-methylimidazolium hydrogen sulfate for levulinic acid production from sugarcane bagasse with membrane-based techniques, Bioresour. Technol. 330 (2021) 124984.
[23] J.H. Kim, J.G. Na, J.W. Yang, Y.K. Chang, Separation of galactose, 5-hydroxymethylfurfural and levulinic acid in acid hydrolysate of agarose by nanofiltration and electrodialysis, Bioresour. Technol. 140 (2013) 64–72.
[24] D. Unlu, O. Ilgen, N. Durmaz Hilmioglu, Reactive separation system for effective upgrade of levulinic acid into ethyl levulinate, Chem. Eng. Res. Des. 118 (2017) 248–258.
[25] J.Y. Zheng, X.D. He, C.L. Cai, J.X. Xiao, Y. Liu, Z. Chen, B.Y. Pan, X.Q. Lin, Adsorption isotherm, kinetics simulation and breakthrough analysis of 5-hydroxymethylfurfural adsorption/desorption behavior of a novel polar-modified post-cross-linked poly (divinylbenzene-co-ethyleneglycoldimethacrylate) resin, Chemosphere 239 (2020) 124732.
[26] X.Q. Lin, Q.L. Huang, G.X. Qi, L. Xiong, C. Huang, X.F. Chen, H.L. Li, X.D. Chen, Adsorption behavior of levulinic acid onto microporous hyper-cross-linked polymers in aqueous solution: Equilibrium, thermodynamic, kinetic simulation and fixed-bed column studies, Chemosphere 171 (2017) 231–239.
[27] X.Q. Lin, Q.L. Huang, G.X. Qi, S.L. Shi, L. Xiong, C. Huang, X.F. Chen, H.L. Li, X.D. Chen, Estimation of fixed-bed column parameters and mathematical modeling of breakthrough behaviors for adsorption of levulinic acid from aqueous solution using SY-01 resin, Sep. Purif. Technol. 174 (2017) 222–231.
[28] J.Y. Zheng, B.Y. Pan, J.X. Xiao, X.D. He, Z. Chen, Q.L. Huang, X.Q. Lin, Experimental and mathematical simulation of noncompetitive and competitive adsorption dynamic of formic acid–levulinic acid–5-hydroxymethylfurfural from single, binary, and ternary systems in a fixed-bed column of SY-01 resin, Ind. Eng. Chem. Res. 57 (25) (2018) 8518–8528.
[29] X.Q. Lin, L. Xiong, G.X. Qi, S.L. Shi, C. Huang, X.F. Chen, X.D. Chen, Using butanol fermentation wastewater for biobutanol production after removal of inhibitory compounds by micro/mesoporous hyper-cross-linked polymeric adsorbent, ACS Sustain. Chem. Eng. 3 (4) (2015) 702–709.
[30] H.M. Ijmker, M. Gramblička, S.R.A. Kersten, A.G.J. van der Ham, B. Schuur, Acetic acid extraction from aqueous solutions using fatty acids, Sep. Purif. Technol. 125 (2014) 256–263.
[31] L.M.J. Sprakel, B. Schuur, Solvent developments for liquid–liquid extraction of carboxylic acids in perspective, Sep. Purif. Technol. 211 (2019) 935–957.
[32] H. Qin, X.T. Hu, J.W. Wang, H.Y. Cheng, L.F. Chen, Z.W. Qi, Overview of acidic deep eutectic solvents on synthesis, properties and applications, Green Energy Environ. 5 (1) (2020) 8–21.
[33] Q. Zhang, K. de Oliveira Vigier, S. Royer, F. Jérôme, Deep eutectic solvents: Syntheses, properties and applications, Chem. Soc. Rev. 41 (21) (2012) 7108–7146.
[34] Y.J. Xie, H.F. Dong, S.J. Zhang, X.H. Lu, X.Y. Ji, Solubilities of CO₂, CH₄, H₂, CO and N₂ in choline chloride/urea, Green Energy Environ. 1 (3) (2016) 195–200.
[35] N.R. Rodriguez, B.S. Molina, M.C. Kroon, Aliphatic + ethanol separation via liquid–liquid extraction using low transition temperature mixtures as extracting agents, Fluid Phase Equilibria 394 (2015) 71–82.
[36] C. Florindo, L.C. Branco, I.M. Marrucho, Quest for green-solvent design: From hydrophilic to hydrophobic (deep) eutectic solvents, ChemSusChem 12 (8) (2019) 1549–1559.
[37] M. Khajavian, V. Vatanpour, R. Castro-Muñoz, G. Boczkaj, Chitin and derivative chitosan-based structures—Preparation strategies aided by deep eutectic solvents: A review, Carbohydr. Polym. 275 (2022) 118702.
[38] R. Castro-Muñoz, A. Msahel, F. Galiano, M. Serocki, J. Ryl, S.B. Hamouda, A. Hafiane, G. Boczkaj, A. Figoli, Towards azeotropic MeOH–MTBE separation using pervaporation chitosan-based deep eutectic solvent membranes, Sep. Purif. Technol. 281 (2022) 119979.
[39] M. Momotko, J. Łuczak, A. Przyjazny, G. Boczkaj, First deep eutectic solvent-based (DES) stationary phase for gas chromatography and future perspectives for DES application in separation techniques, J. Chromatogr. A 1635 (2021) 461701.
[40] J. Cao, M. Yang, F.L. Cao, J.H. Wang, E.Z. Su, Tailor-made hydrophobic deep eutectic solvents for cleaner extraction of polyprenyl acetates from Ginkgo biloba leaves, J. Clean. Prod. 152 (2017) 399–405.
[41] H. Ul Haq, R. Bibi, M. Balal Arain, F. Safi, S. Ullah, R. Castro-Muñoz, G. Boczkaj, Deep eutectic solvent (DES) with silver nanoparticles (Ag-NPs) based assay for analysis of lead (II) in edible oils, Food Chem. 379 (2022) 132085.
[42] T. Hanada, M. Goto, Synergistic deep eutectic solvents for lithium extraction, ACS Sustain. Chem. Eng. 9 (5) (2021) 2152–2160.
[43] W. Chen, X.W. Li, L.L. Chen, G.L. Zhou, Q.Q. Lu, Y. Huang, Y.H. Chao, W.S. Zhu, Tailoring hydrophobic deep eutectic solvent for selective lithium recovery from the mother liquor of Li₂CO₃, Chem. Eng. J. 420 (2021) 127648.
[44] R. Abro, N. Kiran, S. Ahmed, A. Muhammad, A.S. Jatoi, S.A. Mazari, U. Salma, N.V. Plechkova, Extractive desulfurization of fuel oils using deep eutectic solvents—A comprehensive review, J. Environ. Chem. Eng. 10 (3) (2022) 107369.
[45] D.J.G.P. van Osch, L.F. Zubeir, A. van den Bruinhorst, M.A.A. Rocha, M.C. Kroon, Hydrophobic deep eutectic solvents as water-immiscible extractants, Green Chem. 17 (9) (2015) 4518–4521.
[46] A.S. Darwish, S.E.E. Warrag, T. Lemaoui, M.K. Alseiari, F.A. Hatab, R. Rafay, I. Alnashef, J. Rodríguez, N. Alamoodi, Green extraction of volatile fatty acids from fermented wastewater using hydrophobic deep eutectic solvents, Fermentation 7 (4) (2021) 226.
[47] J.Z. Liu, H.C. Lyu, Y.J. Fu, J.C. Jiang, Q. Cui, Simultaneous extraction of natural organic acid and flavonoid antioxidants from Hibiscus manihot L. flower by tailor-made deep eutectic solvent, LWT 163 (2022) 113533.
[48] A.P. Abbott, G. Capper, D.L. Davies, R.K. Rasheed, V. Tambyrajah, Novel solvent properties of choline chloride/urea mixtures, Chem. Commun. (1) (2003) 70–71.
[49] R. Verma, T. Banerjee, Liquid–liquid extraction of lower alcohols using menthol-based hydrophobic deep eutectic solvent: Experiments and COSMO-SAC predictions, Ind. Eng. Chem. Res. 57 (9) (2018) 3371–3381.
[50] M.H. Zainal-Abidin, M. Hayyan, W.F. Wong, Hydrophobic deep eutectic solvents: Current progress and future directions, J. Ind. Eng. Chem. 97 (2021) 142–162.
[51] P. Makoś, A. Przyjazny, G. Boczkaj, Hydrophobic deep eutectic solvents as “green” extraction media for polycyclic aromatic hydrocarbons in aqueous samples, J. Chromatogr. A 1570 (2018) 28–37.
[52] L.J. Liu, B.L. Su, Q.F. Wei, X.L. Ren, Selective separation of lactic, malic, and tartaric acids based on the hydrophobic deep eutectic solvents of terpenes and amides, Green Chem. 23 (16) (2021) 5866–5874.
[53] M. Marchel, H. Cieśliński, G. Boczkaj, Deep eutectic solvents microbial toxicity: Current state of art and critical evaluation of testing methods, J. Hazard. Mater. 425 (2022) 127963.
[54] E. Riveiro, B. González, Á. Domínguez, Extraction of adipic, levulinic and succinic acids from water using TOPO-based deep eutectic solvents, Sep. Purif. Technol. 241 (2020) 116692.
[55] T. Brouwer, B.C. Dielis, J.M. Bock, B. Schuur, Hydrophobic deep eutectic solvents for the recovery of bio-based chemicals: Solid–liquid equilibria and liquid–liquid extraction, Processes 9 (5) (2021) 796.
[56] R.H. Liu, Y.Q. Geng, Z.J. Tian, N. Wang, M. Wang, G.J. Zhang, Y.Z. Yang, Extraction of platinum(IV) by hydrophobic deep eutectic solvents based on trioctylphosphine oxide, Hydrometallurgy 199 (2021) 105521.
[57] Y.H. Ji, Z.R. Meng, J. Zhao, H.Q. Zhao, L.S. Zhao, Eco-friendly ultrasonic assisted liquid–liquid microextraction method based on hydrophobic deep eutectic solvent for the determination of sulfonamides in fruit juices, J. Chromatogr. A 1609 (2020) 460520.
[58] D. Núñez, P. Oulego, S. Collado, F.A. Riera, M. Díaz, Recovery of organic acids from pre-treated Kraft black liquor using ultrafiltration and liquid–liquid extraction, Sep. Purif. Technol. 284 (2022) 120274.
[59] G.M. Teke, R.W.M. Pott, Design and evaluation of a continuous semipartition bioreactor for in situ liquid–liquid extractive fermentation, Biotechnol. Bioeng. 118 (1) (2021) 58–71.
[60] C. Florindo, L. Romero, I. Rintoul, L.C. Branco, I.M. Marrucho, From phase change materials to green solvents: Hydrophobic low viscous fatty acid-based deep eutectic solvents, ACS Sustain. Chem. Eng. 6 (3) (2018) 3888–3895.
[61] X.J. Zheng, X.L. Xian, L. Hu, S.H. Tao, X.D. Zhang, Y. Liu, X.Q. Lin, Efficient short-time hydrothermal depolymerization of sugarcane bagasse in one-pot for cellulosic ethanol production without solid–liquid separation, water washing, and detoxification, Bioresour. Technol. 339 (2021) 125575.
[62] X.Q. Lin, J.L. Wu, J.S. Fan, W.B. Qian, X.Q. Zhou, C. Qian, X.H. Jin, L.L. Wang, J.X. Bai, H.J. Ying, Adsorption of butanol from aqueous solution onto a new type of macroporous adsorption resin: Studies of adsorption isotherms and kinetics simulation, J. Chem. Technol. Biotechnol. 87 (7) (2012) 924–931.
[63] X.Q. Lin, J.L. Wu, X.H. Jin, J.S. Fan, R.J. Li, Q.S. Wen, W.B. Qian, D. Liu, X.C. Chen, Y. Chen, J.J. Xie, J.X. Bai, H.J. Ying, Selective separation of biobutanol from acetone–butanol–ethanol fermentation broth by means of sorption methodology based on a novel macroporous resin, Biotechnol. Prog. 28 (4) (2012) 962–972.
[64] M. Marchel, H. Cieśliński, G. Boczkaj, Thermal instability of choline chloride-based deep eutectic solvents and its influence on their toxicity—Important limitations of DESs as sustainable materials, Ind. Eng. Chem. Res. 61 (30) (2022) 11288–11300.
[65] W.J. Chen, Z.M. Xue, J.F. Wang, J.Y. Jiang, X.H. Zhao, T.C. Mu, Investigation on the thermal stability of deep eutectic solvents, Acta Phys. Chim. Sin. 34 (8) (2018) 904–911.
[66] D. Datta, M.E. Marti, H. Uslu, S. Kumar, Extraction of levulinic acid using tri-n-butyl phosphate and tri-n-octylamine in 1-octanol: Column design, J. Taiwan Inst. Chem. Eng. 66 (2016) 407–413.
[67] S. Eda, A. Borra, R. Parthasarathy, S. Bankupalli, S. Bhargava, P.K. Thella, Recovery of levulinic acid by reactive extraction using tri-n-octylamine in methyl isobutyl ketone: Equilibrium and thermodynamic studies and optimization using Taguchi multivariate approach, Sep. Purif. Technol. 197 (2018) 314–324.
[68] A. Farzaneh, M. Zhou, O.N. Antzutkin, Z. Bacsik, J. Hedlund, A. Holmgren, M. Grahn, Adsorption of butanol and water vapors in silicalite-1 films with a low defect density, Langmuir 32 (45) (2016) 11789–11798.
[69] X.R. Qiu, Z.D. Chang, H.L. Zhou, W.J. Li, B. Dong, Effect of hydroxyl on formation of viscoelastic scum during solvent extraction of sulfuric acid with trioctylamine, Sep. Purif. Technol. 86 (2012) 137–142.
[70] A. Mohanty, N. Devi, L.B. Sukla, N. Swain, Liquid–liquid extraction of Co(II) from nitrate solution using TOA, Mater. Today Proc. 30 (2020) 262–266.

Liquid–liquid extraction of levulinic acid from aqueous solutions using hydrophobic tri-n-octylamine/alcohol-based deep eutectic solvent

Liquid–liquid extraction of levulinic acid from aqueous solutions using hydrophobic tri-n-octylamine/alcohol-based deep eutectic solvent

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