Iranian Journal of Chemistry

Iranian Journal of Chemistry

An overview on the introduction, properties, and applications of deep eutectic solvents

Document Type : Original Article

Authors
Shahrbanoo Saraee 1
Fatemeh Moosavi 2
1 Department of Chemistry, Faculty of Sciences, Ferdowsi University of Mashhad, 9177948974, Mashhad, Iran
2 Department of Chemistry, Faculty of Science, Ferdowsi University of Mashahd
10.22036/cr.2024.423948.1223
Abstract
Deep eutectic solvents (DESs) are of great interest due to their unique properties and wide applications in medical, health, and industrial fields. Growing use of this class of green solvents, access to a deep insight into the characteristics, mechanism of action, and DESs behavior is important. Considering different experimental and theoretical approaches such as classical molecular dynamics simulation, the diffusion coefficient and density of DESs based on hydrogen bond acceptor (HBA) and hydrogen bond donor (HBD) are discussed. The effects caused by changing the HBD component, temperature, interactions related to the formation of hydrogen bond (HB), and presence of water in the vicinity of DESs on dynamic properties and density are evaluated. Various factors including structural factors may change physicochemical and transfer properties. In this regard, factors such as temperature, molar ratio of components, and the way HB is formed between HBD and HBA play an important role in determining the properties of the solvent. Considering that DESs are widely used as safe and environmentally friendly solvents in various fields such as water resources health, medicine, and industry, they are often of interest to researchers. Mainly, these DES properties control the application and mode of action in the face of other compounds and various processes. Considering the positive effect of the DESs properties on their mechanism of action, knowing the characteristics and different aspects of the performance of these systems can be associated with positive prospects and in the direction improving the use of these solvents took a big step.

Graphical Abstract

An overview on the introduction, properties, and applications of deep eutectic solvents
Keywords
application
classification
deep eutectic solvent
density
diffusion coefficient

Subjects

  1. [1] Zainal-Abidin, M. H., Hayyan, M., Ngoh, G. C., Wong, W. F., and Looi, C. Y., Journal of Controlled

    Release, 316 (2019) 168-195.

    [2] Liu, Y., Friesen, J. B., McAlpine, J. B., Lankin, D. C., Chen, S.-N., and Pauli, G. F., Journal of Natural

    Products, 81 (2018) 679-690.

    [3] D'Agostino, C., Harris, R. C., Abbott, A. P., Gladden, L. F., and Mantle, M. D., Physical Chemistry

    Chemical Physics, 13 (2011) 21383-21391.

    [4] Florindo, C., Oliveira, F. S., Rebelo, L. P. N., Fernandes, A. M., and Marrucho, I. M., ACS

    Sustainable Chemistry & Engineering, 2 (2014) 2416-2425.

    [5] Smith, E. L., Abbott, A. P., and Ryder, K. S., Chemical Reviews, 114 (2014) 11060-11082.

    [6] Bonab, P. J., Esrafili, M. D., Ebrahimzadeh, A. R., and Sardroodi, J. J., Journal of Molecular Graphics and Modelling, 106 (2021) 107908.

    [7] Kovács, A., Neyts, E. C., Cornet, I., Wijnants, M., and Billen, P., ChemSusChem, 13 (2020) 3789-3804.

    [8] Yang, Z., Natural deep eutectic solvents and their applications in biotechnology. Application of ionic

    liquids in biotechnology.2019.

    [9] Lomba, L., Ribate, M. P., Sangüesa, E., Concha, J., Garralaga, M. P., Errazquin, D., García, C. B., and

    Giner, B., Applied Sciences, 11 (2021) 10061.

    [10] Abbott, A. P., Capper, G., Davies, D. L., McKenzie, K. J., and Obi, S. U., Journal of Chemical & Engineering Data, 51 (2006) 1280-1282.

    [11] Abo-Hamad, A., Hayyan, M., AlSaadi, M. A., and Hashim, M. A., Chemical Engineering Journal, 273

    (2015) 551-567.

    [12] Zhekenov, T., Toksanbayev, N., Kazakbayeva, Z., Shah, D., and Mjalli, F. S., Fluid Phase Equilibria, 441 (2017) 43-48.

    [13] Jahanbakhsh Bonab, P., Rastkar Ebrahimzadeh, A., and Jahanbin Sardroodi, J., Scientific Reports, 11 (2021) 1-18.

    [14] Abbott, A. P., Boothby, D., Capper, G., Davies, D. L., and Rasheed, R. K., Journal of the American

    Chemical Society, 126 (2004) 9142-9147.

    [15] Long, G., Yang, C., Yang, X., Zhao, T., Liu, F., and Cao, J., ACS Sustainable Chemistry & Engineering, 8

    (2020) 2608-2613.

    [16] Long, G., Yang, C., Yang, X., Zhao, T., and Xu, M., Journal of Molecular Liquids, 302 (2020) 112538.

    [17] Li, C., Cai, Z., Ma, Y., Cao, Y., Huang, K., and Jiang, L., The Journal of Chemical Thermodynamics,

    167 (2022) 106713.

    [18] Shahbaz, K., Mjalli, F. S., Hashim, M. A., and AlNashef, I. M., Thermochimica Acta, 515 (2011) 67

    1.  

    [19] Płotka-Wasylka, J., De la Guardia, M., Andruch, V., and Vilková, M., Microchemical Journal, 159 (2020) 105539.

    [20] Xu, J., Zhou, Q., Wang, X., Lu, X., and Zhang, S., Fundamentals of Ionic Liquids, in Production of

    Biofuels and Chemicals with Ionic Liquids, Z. Fang, J.R.L. Smith, and X. Qi, Editors, (2014) 3-28.

    [21] Şahin, S., Journal of Pharmaceutical and Biomedical Analysis, 174 (2019) 324-329.

    [22] Duan, L., Dou, L.-L., Guo, L., Li, P., and Liu, E. H., ACS Sustainable Chemistry & Engineering, 4

    (2016) 2405-2411.

    [23] Mbous, Y. P., Hayyan, M., Hayyan, A., Wong, W. F., Hashim, M. A., and Looi, C. Y., Biotechnology

    Advances, 35 (2017) 105-134.

    [24] El Achkar, T., Fourmentin, S., and Greige-Gerges, H., Journal of Molecular Liquids, 288 (2019) 111028.

    [25] Ruesgas-Ramón, M., Figueroa-Espinoza, M. C., and Durand, E., Journal of Agricultural and Food

    Chemistry, 65 (2017) 3591-3601.

    [26] Nam, M. W., Zhao, J., Lee, M. S., Jeong, J. H., and Lee, J., Green Chemistry, 17 (2015) 1718-1727.

    [27] Gutiérrez, M. C., Ferrer, M. L., Mateo, C. R., and del Monte, F., Langmuir, 25 (2009) 5509-5515.

    [28] Hayyan, A., Hashim, M. A., Mjalli, F. S., Hayyan, M., and AlNashef, I. M., Chemical Engineering Science, 92 (2013) 81-88.

    [29] Hayyan, A., Hashim, M. A., Hayyan, M., Mjalli, F. S., and AlNashef, I. M., Journal of Cleaner Production, 65 (2014) 246-251.

    [30] Gutiérrez, A., Atilhan, M., and Aparicio, S., Physical Chemistry Chemical Physics, 20 (2018)

    27464-27473.

    [31] Gutiérrez, A., Atilhan, M., and Aparicio, S., The Journal of Physical Chemistry B, 124 (2020) 1794

    1.  

    [32] Gutiérrez, A., Atilhan, M., and Aparicio, S., Journal of Chemical & Engineering Data, 65 (2020) 4669-4683.

    [33] Sailau, Z., Almas, N., Aldongarov, A., and Toshtay, K., Journal of Molecular Modeling, 28 (2022) 235.

    [34] Indra, S., Subramanian, R., and Daschakraborty, S., The Journal of Physical Chemistry B, 126 (2022) 3705-3716.

    [35] Huang, Y., Ho, S. S. H., Lu, Y., Niu, R., Xu, L., Cao, J., and Lee, S., Molecules, 21 (2016) 56.

    [36] Buss, W. and Mašek, O., Environmental Science and Pollution Research, 23 (2016) 19580-19589.

    [37] Dumont, E., Darracq, G., Couvert, A., Couriol, C., Amrane, A., Thomas, D., Andrès, Y., and Le Cloirec, P., Chemical Engineering Journal, 168 (2011) 241-248.

    [38] Darracq, G., Couvert, A., Couriol, C., Amrane, A., Thomas, D., Dumont, E., Andres, Y., and Le Cloirec, P., Journal of Chemical Technology & Biotechnology, 85 (2010) 309-313.

    [39] Heymes, F., Manno-Demoustier, P., Charbit, F., Fanlo, J. L., and Moulin, P., Chemical Engineering

    Journal, 115 (2006) 225-231.

    [40] Fahri, F., Bacha, K., Chiki, F. F., Mbakidi, J.-P., Panda, S., Bouquillon, S., and Fourmentin, S.,

    Environmental Chemistry Letters, 18 (2020) 1403-1411.

    [41] Romero, A., Santos, A., Tojo, J., and Rodríguez, A., Journal of Hazardous Materials, 151 (2008) 268-

    1.  

    [42] Kudłak, B., Owczarek, K., and Namieśnik, J., Environmental Science and Pollution Research, 22

    (2015) 11975-11992.

    [43] Paiva, A., Craveiro, R., Aroso, I., Martins, M., Reis, R. L., and Duarte, A. R. C., ACS Sustainable Chemistry & Engineering, 2 (2014) 1063-1071.

    [44] Gill, I. and Vulfson, E., Trends in Biotechnology, 12 (1994) 118-122.

    [45] López‐Fandiño, R., Gill, I., and Vulfson, E. N., Biotechnology and Bioengineering, 43 (1994) 1024

    1.  

    [46] Ghobadi, R. and Divsalar, A., Journal of Molecular Liquids, 310 (2020) 113207.

    [47] Wang, Y., Cheng, H., He, J.-R., Yao, Q.-X., Li, L.L., Liang, Z.-H., and Li, X., Catalysis Letters, 152

    (2022) 1215-1223.

    [48] Davey, R., Garside, J., Hilton, A., McEwan, D., and Morrison, J., Nature, 375 (1995) 664-666.

    [49] Álvarez, M. S. and Zhang, Y., Journal of Controlled Release, 311 (2019) 225-232.

    [50] Kim, J., Shi, Y., Kwon, C. J., Gao, Y., and Mitragotri, S., Advanced Healthcare Materials, 10

    (2021) 2100585.

    [51] Golgoun, S., Mokhtarpour, M., and Shekaari, H., Pharmaceutical Sciences, 27 (2020) 86-101.

    [52] Mustafa, N. R., Spelbos, V. S., Witkamp, G.-J., Verpoorte, R., and Choi, Y. H., Molecules, 26 (2021)

    1.  

    [53] Li, X. and Row, K. H., Journal of Separation Science, 39 (2016) 3505-3520.

    [54] Wen, Q., Chen, J.-X., Tang, Y.-L., Wang, J., and Yang, Z., Chemosphere, 132 (2015) 63-69.

    [55] Schaeffer, N., Abranches, D. O., Silva, L. P., Martins, M. A., Carvalho, P. J., Russina, O., Triolo, A.,

    Paccou, L., Guinet, Y., and Hedoux, A., ACS Sustainable Chemistry & Engineering, 9 (2021) 2203

    1.  

    [56] Martins, M. A., Silva, L. P., Schaeffer, N., Abranches, D. O., Maximo, G. J., Pinho, S. P., and

    Coutinho, J. A., ACS Sustainable Chemistry & Engineering, 7 (2019) 17414-17423.

    [57] Kaul, M. J., Qadah, D., Mandella, V., and Dietz, M. L., RSC Advances, 9 (2019) 15798-15804.

    [58] Schaeffer, N., Conceição, J. H., Martins, M. A., Neves, M. C., Pérez-Sánchez, G., Gomes, J. R.,

    Papaiconomou, N., and Coutinho, J. A., Green Chemistry, 22 (2020) 2810-2820.

    [59] Silva, N. H., Morais, E. S., Freire, C. S., Freire, M. G., and Silvestre, A. J., Molecules, 25 (2020) 210.

    [60] Abranches, D. O., Martins, M. A., Silva, L. P., Schaeffer, N., Pinho, S. P., and Coutinho, J. A.,

    Chemical Communications, 55 (2019) 10253-10256.

    [61] Lu, W. and Chen, H., Journal of Molecular Liquids, 349 (2022) 118105.

    [62] Zhang, K., Liu, C., Li, S., and Fan, J., Journal of Chromatography A, 1589 (2019) 39-46.

    [63] Wang, L.-T., Yang, Q., Cui, Q., Fan, X.-H., Dong, M.-Z., Gao, M.-Z., Lv, M.-J., An, J.-Y., Meng, D., and

    Zhao, X.-H., Journal of Cleaner Production, 244 (2020) 118648.

    [64] Musarurwa, H. and Tavengwa, N. T., Talanta, 223 (2021) 121507.

    [65] Shishov, A., Pochivalov, A., Nugbienyo, L., Andruch, V., and Bulatov, A., TrAC Trends in

    Analytical Chemistry, 129 (2020) 115956.

    [66] van Osch, D. J., Zubeir, L. F., van den Bruinhorst, A., Rocha, M. A., and Kroon, M. C., Green Chemistry, 17 (2015) 4518-4521.

    [67] Cao, J. and Su, E., Journal of Cleaner Production, 314 (2021) 127965.

    [68] Chabib, C. M., Ali, J. K., Abi Jaoude, M., Alhseinat, E., Adeyemi, I. A., and Al Nashef, I. M.,

    Journal of Water Process Engineering, 47 (2022) 102663.

    [69] Makoś, P., Słupek, E., and Gębicki, J., Microchemical Journal, 152 (2020) 104384.

    [70] Schaeffer, N., Martins, M. A., Neves, C. M., Pinho, S. P., and Coutinho, J. A., Chemical Communications, 54 (2018) 8104-8107.

    [71] Abbott, A. P., Capper, G., Davies, D. L., Munro, H. L., Rasheed, R. K., and Tambyrajah, V., Chemical

    Communications, (2001) 2010-2011.

    [72] Abbott, A. P., Capper, G., Davies, D. L., Rasheed, R. K., and Tambyrajah, V., Chemical communications, (2003) 70-71.

    [73] Alizadeh, V., Malberg, F., Pádua, A. A. H., and Kirchner, B., The Journal of Physical Chemistry B, 124

    (2020) 7433-7443.

    [74] Zhang, H., Lu, X., González-Aguilera, L., Ferrer, M. L., Del Monte, F., and Gutiérrez, M. C., The Journal

    of Chemical Physics, 154 (2021) 184501.

    [75] Juneidi, I., Hayyan, M., and Hashim, M. A., RSC Advances, 5 (2015) 83636-83647.

    [76] Hayyan, M., Looi, C. Y., Hayyan, A., Wong, W. F., and Hashim, M. A., PloS one, 10 (2015) e0117934.

    [77] Hayyan, M., Hashim, M. A., Al-Saadi, M. A., Hayyan, A., AlNashef, I. M., and Mirghani, M. E.,

    Chemosphere, 93 (2013) 455-459.

    [78] Hayyan, M., Hashim, M. A., Hayyan, A., Al-Saadi, M. A., AlNashef, I. M., Mirghani, M. E., and Saheed, O. K., Chemosphere, 90 (2013) 2193-2195.

    [79] Mitar, A., Panić, M., Prlić Kardum, J., Halambek, J., Sander, A., Zagajski Kučan, K., Radojčić

    Redovniković, I., and Radošević, K., Chemical and Biochemical Engineering Quarterly, 33 (2019) 1-18.

    [80] Zhao, B.-Y., Xu, P., Yang, F.-X., Wu, H., Zong, M.-H., and Lou, W.-Y., ACS Sustainable Chemistry &

    Engineering, 3 (2015) 2746-2755.

    [81] Radošević, K., Bubalo, M. C., Srček, V. G., Grgas, D., Dragičević, T. L., and Redovniković, I. R.,

    Ecotoxicology and Environmental Safety, 112 (2015) 46-53.

    [82] Marchel, M., Cieśliński, H., and Boczkaj, G., Journal of Hazardous Materials, 425 (2022) 127963.

    [83] Zhang, Q., Vigier, K. D. O., Royer, S., and Jérôme, F., Chemical Society Reviews, 41 (2012) 7108-7146.

    [84] Ma, C., Laaksonen, A., Liu, C., Lu, X., and Ji, X., Chemical Society Reviews, 47 (2018) 8685-8720.

    [85] Florindo, C., Branco, L., and Marrucho, I., Fluid Phase Equilibria, 448 (2017) 135-142.

    [86] Florindo, C., McIntosh, A., Welton, T., Branco, L., and Marrucho, I., Physical Chemistry Chemical Physics, 20 (2018) 206-213.

    [87] Pandey, A., Rai, R., Pal, M., and Pandey, S., Physical Chemistry Chemical Physics, 16 (2014) 1559

    1.  

    [88] Teles, A. R. R., Capela, E. V., Carmo, R. S., Coutinho, J. A., Silvestre, A. J., and Freire, M. G., Fluid

    Phase Equilibria, 448 (2017) 15-21.

    [89] Gautam, R. K. and Seth, D., Journal of Thermal Analysis and Calorimetry, 140 (2020) 2633-2640.

    [90] Shaabani, A., Hooshmand, S. E., Afshari, R., Shaabani, S., Ghasemi, V., Atharnezhad, M., and

    Akbari, M., Journal of Solid State Chemistry, 258 (2018) 536-542.

    [91] Ellahi, R., Zeeshan, A., Shehzad, N., and Alamri, S. Z., Journal of Molecular Liquids, 264 (2018) 607

    615.

    [92] Ge, R., Hardacre, C., Nancarrow, P., and Rooney, D. W., Journal of Chemical & Engineering Data, 52

    (2007) 1819-1823.

    [93] Gardas, R. L., Ge, R., Goodrich, P., Hardacre, C., Hussain, A., and Rooney, D. W., Journal of Chemical & Engineering Data, 55 (2010) 1505-1515.

    [94] Rodil, E., Arce Jr, A., Arce, A., and Soto, A., Thermochimica Acta, 664 (2018) 81-90.

    [95] Zhao, Y., Zhen, Y., Jelle, B. P., and Boström, T., Journal of Thermal Analysis and Calorimetry, 128

    (2017) 279-288.

    [96] Albayati, N., Kadhom, M., Abdullah, G., and Salih, S., Journal of Thermal Science, 30 (2021) 1960-1972.

    [97] Ibrahim, T. H., Sabri, M. A., Abdel Jabbar, N., Nancarrow, P., Mjalli, F. S., and AlNashef, I.,

    Molecules, 25 (2020) 3816.

    [98] Atilhan, M. and Aparicio, S., Journal of Thermal Analysis and Calorimetry, (2023) 1-12.

    [99] El Achkar, T., Greige-Gerges, H., and Fourmentin, S., Environmental Chemistry Letters, 19 (2021) 3397-3408.

    [100] Tang, B. and Row, K. H., Monatshefte für Chemie-Chemical Monthly, 144 (2023) 1427-1454.

    [101] Cui, Y., Li, C., Yin, J., Li, S., Jia, Y., and Bao, M., Journal of Molecular Liquids, 236 (2017) 338-343.

    [102] Ibrahim, R. K., Hayyan, M., AlSaadi, M. A., Ibrahim, S., Hayyan, A., and Hashim, M. A., Journal of

    Molecular Liquids, 276(2019) 794-800.

    [103] Perkins, S. L., Painter, P., and Colina, C. M., Journal of Chemical & Engineering Data, 59 (2014)

    3652-3662.

    [104] Perkins, S. L., Painter, P., and Colina, C. M., The Journal of Physical Chemistry B, 117 (2013) 10250

    1.  

    [105] Moradi, H. and Farzi, N., Journal of Molecular Liquids, 339 (2021) 116669.

    [106] Gutiérrez, A., Atilhan, M., and Aparicio, S., Journal of Molecular Liquids, 339 (2021) 116758.

    [107] Elhamarnah, Y. A., Nasser, M., Qiblawey, H., Benamor, A., Atilhan, M., and Aparicio, S., Journal of

    Molecular Liquids, 277 (2019) 932-958.

    [108] Gutiérrez, A., Alcalde, R., Atilhan, M., and Aparicio, S., Industrial & Engineering Chemistry

    Research, 59 (2020) 11880-11892.

    [109] López-Salas, N., Vicent-Luna, J. M., Imberti, S., Posada, E., Roldán, M. J., Anta, J. A., Balestra, S. R. G., Madero Castro, R. M., Calero, S., Jiménez-Riobóo, R. J., Gutiérrez, M. C., Ferrer, M. L., and del Monte, F., ACS Sustainable Chemistry & Engineering, 7 (2019) 17565-17573.

    [110] Smith, P. J., Arroyo, C. B., Lopez Hernandez, F., and Goeltz, J. C., The Journal of Physical Chemistry B, 123 (2019) 5302-5306.

    [111] Dwamena, A. K., Separations, 6 (2019) 9. [112] Pour, S. B., Sardroodi, J. J., Ebrahimzadeh, A. R.,

    and pazuki, g. r., The effect of water on the interaction between species in Deep-Eutectic Solvents Based on Choline Chloride and Fatty Acids: insights from molecular dynamics simulation, (2022), Research

    Square.

     [115] McQuarrie, D. A., Statistical Mechanics. (1977).

     [117] Barani Pour, S., Jahanbin Sardroodi, J., and Rastkar Ebrahimzadeh, A., Journal of Molecular

    Liquids, 334 (2021) 115956.

    [118] Doherty, B. and Acevedo, O., The Journal of Physical Chemistry B, 122 (2018) 9982-9993.

    [119] Pour, S. B., Sardroodi, J. J., and Ebrahimzadeh, A. R., Fluid Phase Equilibria, 552 (2022) 113241.

    [120] Delso, I., Lafuente, C., Muñoz-Embid, J., and Artal, M., Journal of Molecular Liquids, 290 (2019)

    1.  

    [121] Yadav, A. and Pandey, S., Journal of Chemical & Engineering Data, 59 (2014) 2221-2229.

    [122] Qin, H., Hu, X., Wang, J., Cheng, H., Chen, L., and Qi, Z., Green Energy & Environment, 5 (2020) 8

    1.  

    [123] Glasser, L., Thermochimica Acta, 421 (2004) 87-93.

    [124] Paul, N., Naik, P. K., Ribeiro, B. D., Gooh Pattader, P. S., Marrucho, I. M., and Banerjee, T., The

    Journal of Physical Chemistry B, 124 (2020) 7405-7420.

    [125] Jahanbakhsh-Bonab, P., Esrafili, M. D., Rastkar Ebrahimzadeh, A., and Jahanbin Sardroodi, J., Journal of Molecular Liquids, 338 (2021) 116716.

    [126] Rozas, S., Alomari, N., Atilhan, M., and Aparicio, S., The Journal of Chemical Physics, 154 (2021)

    1.  

    [127] Abbott, A. P., Harris, R. C., and Ryder, K. S., The Journal of Physical Chemistry B, 111 (2007) 4910

    1.  

    [128] Gontrani, L., Plechkova, N. V., and Bonomo, M., ACS Sustainable Chemistry & Engineering, 7 (2019)

    12536-12543.

    [129] Crespo, E. A., Silva, L. P., Martins, M. A. R., Bülow, M., Ferreira, O., Sadowski, G., Held, C., Pinho,

    1. P., and Coutinho, J. A. P., Industrial & Engineering Chemistry Research, 57 (2018) 11195-11209.

    [130] Das, L., Mukherjee, S., Kumar Maity, D., and Adhikari, S., Journal of Molecular Liquids, 360 (2022)

    1. [131] Taysun, M. B., Sert, E., and Atalay, F. S., Journal of Chemical & Engineering Data, 62 (2017) 1173-1181.

    [132] AlOmar, M. K., Hayyan, M., Alsaadi, M. A., Akib, S., Hayyan, A., and Hashim, M. A., Journal of

    Molecular Liquids, 215 (2016) 98-103.

    [133] Mjalli, F. S., Murshid, G., Al-Zakwani, S., and Hayyan, A., Fluid Phase Equilibria, 448 (2017) 30-40.

    [134] Kareem, M. A., Mjalli, F. S., Hashim, M. A., and AlNashef, I. M., Journal of Chemical & Engineering

    Data, 55 (2010) 4632-4637.

     

Iranian Journal of Chemistry
Volume 6, Issue 2 - Serial Number 11
December 2023
Pages 111-135

  • Receive Date 26 November 2023
  • Revise Date 07 January 2024
  • Accept Date 20 January 2024