Abstract
The disclosure of deep eutectic solvents represents a landmark in green chemistry. These systems were reported only 17 years ago and yet resulted in a plethora of publications covering various research areas and diverse fields of application. Their economic and straightforward preparation using highly accessible and natural compounds together with their extremely great tunability were enough to consider them as alternatives to the conventional organic solvents. Besides, deep eutectic solvents hold interesting properties suggesting a promising contribution in multiple domains.
Herein, the classification of deep eutectic solvents and the reported preparation methods to date are presented. Further, their physicochemical properties, namely, their phase behavior, density, viscosity, ionic conductivity, surface tension, and polarity, are summarized. The stated properties are affected by various parameters such as the choice of the forming compounds, their molar ratio, the temperature, and the water content. Finally, in the last section, we entirely present the impact of water on both the physicochemical properties and the characteristic supramolecular network of deep eutectic solvents.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Similar content being viewed by others
Abbreviations
- BA :
-
Butyric acid
- CA :
-
Caprylic acid
- ChCl :
-
Choline chloride
- DEG :
-
Diethylene glycol
- DES :
-
Deep eutectic solvents
- DSC :
-
Differential scanning calorimetry
- EG:
-
Ethylene glycol
- G :
-
Glycerol
- HBA :
-
Hydrogen bond acceptor
- HBD :
-
Hydrogen bond donor
- LA :
-
Lactic acid
- Lev :
-
Levulinic acid
- MA :
-
Malonic acid
- MD :
-
Molecular dynamics
- NADES :
-
Natural deep eutectic solvents
- NMR :
-
Nuclear magnetic resonance
- PEG :
-
Polyethylene glycol
- RAMEB:
-
Randomly methylated β-cyclodextrin
- TBABr :
-
Tetrabutylammonium bromide
- TBACl :
-
Tetrabutylammonium chloride
- TEG :
-
Triethylene glycol
- THEDES:
-
Therapeutic deep eutectic solvents
- U :
-
Urea
- VA :
-
Valeric acid
References
Abbott AP, Capper G, Davies DL, Munro HL, Rasheed RK, Tambyrajah V (2001) Preparation of novel, moisture-stable, Lewis-acidic ionic liquids containing quaternary ammonium salts with functional side chains. Chem Commun (19):2010–2011. https://doi.org/10.1039/B106357J
Abbott AP, Capper G, Davies DL, Rasheed RK, Tambyrajah V (2003) Novel solvent properties of choline chloride/urea mixtures. Chem Commun 1:70–71. https://doi.org/10.1039/B210714G
Abbott AP, Boothby D, Capper G, Davies DL, Rasheed RK (2004a) Deep eutectic solvents formed between choline chloride and carboxylic acids: versatile alternatives to ionic liquids. J Am Chem Soc 126(29):9142–9147. https://doi.org/10.1021/ja048266j
Abbott AP, Capper G, Davies DL, Rasheed RK (2004b) Ionic liquid analogues formed from hydrated metal salts. Chem Eur J 10(15):3769–3774. https://doi.org/10.1002/chem.200400127
Abbott AP, Capper G, Gray S (2006) Design of improved deep eutectic solvents using hole theory. ChemPhysChem 7(4):803–806. https://doi.org/10.1002/cphc.200500489
Abbott AP, Barron JC, Ryder KS, Wilson D (2007a) Eutectic-based ionic liquids with metal-containing anions and cations. Chem Eur J 13(22):6495–6501. https://doi.org/10.1002/chem.200601738
Abbott AP, Harris RC, Ryder KS (2007b) Application of hole theory to define ionic liquids by their transport properties †. J Phys Chem B 111(18):4910–4913. https://doi.org/10.1021/jp0671998
Abbott AP, Harris RC, Ryder KS, D’Agostino C, Gladden LF, Mantle MD (2011) Glycerol eutectics as sustainable solvent systems. Green Chem 13(1):82–90. https://doi.org/10.1039/C0GC00395F
Abranches DO, Martins MAR, Silva LP, Schaeffer N, Pinho SP, Coutinho JAP (2019) Phenolic hydrogen bond donors in the formation of non-ionic deep eutectic solvents: the quest for type V DES. Chem Commun 55(69):10253–10256. https://doi.org/10.1039/C9CC04846D
Agieienko V, Buchner R (2019) Densities, viscosities, and electrical conductivities of pure anhydrous reline and its mixtures with water in the temperature range (293.15 to 338.15) K. J Chem Eng Data 64(11):4763–4774. https://doi.org/10.1021/acs.jced.9b00145
Ahmadi R, Hemmateenejad B, Safavi A, Shojaeifard Z, Shahsavar A, Mohajeri A, Dokoohaki MH, Zolghadr AR (2018) Deep eutectic–water binary solvent associations investigated by vibrational spectroscopy and chemometrics. Phys Chem Chem Phys 20(27):18463–18473. https://doi.org/10.1039/C8CP00409A
Alcalde R, Gutiérrez A, Atilhan M, Aparicio S (2019) An experimental and theoretical investigation of the physicochemical properties on choline chloride – lactic acid based natural deep eutectic solvent (NADES). J Mol Liq 290:110916. https://doi.org/10.1016/j.molliq.2019.110916
Aroso IM, Paiva A, Reis RL, Duarte ARC (2017) Natural deep eutectic solvents from choline chloride and betaine – physicochemical properties. J Mol Liq 241:654–661. https://doi.org/10.1016/j.molliq.2017.06.051
Celebi AT, Vlugt TJH, Moultos OA (2019) Structural, thermodynamic, and transport properties of aqueous reline and ethaline solutions from molecular dynamics simulations. J Phys Chem B 123(51):11014–11025. https://doi.org/10.1021/acs.jpcb.9b09729
Chen Z, Ludwig M, Warr GG, Atkin R (2017) Effect of cation alkyl chain length on surface forces and physical properties in deep eutectic solvents. J Colloid Interface Sci 494:373–379. https://doi.org/10.1016/j.jcis.2017.01.109
Chen W, Bai X, Xue Z, Mou H, Chen J, Liu Z, Mu T (2019a) The formation and physicochemical properties of PEGylated deep eutectic solvents. New J Chem 43(22):8804–8810. https://doi.org/10.1039/C9NJ02196E
Chen Y, Yu D, Chen W, Fu L, Mu T (2019b) Water absorption by deep eutectic solvents. Phys Chem Chem Phys 21(5):2601–2610. https://doi.org/10.1039/C8CP07383J
Choi YH, van Spronsen J, Dai Y, Verberne M, Hollmann F, Arends IWCE, Witkamp G-J, Verpoorte R (2011) Are natural deep eutectic solvents the missing link in understanding cellular metabolism and physiology? Plant Physiol 156(4):1701–1705. https://doi.org/10.1104/pp.111.178426
Coutinho JAP, Pinho SP (2017) Special issue on deep eutectic solvents: a foreword. Fluid Phase Equilib 448:1. https://doi.org/10.1016/j.fluid.2017.06.011
Cui Y, Li C, Yin J, Li S, Jia Y, Bao M (2017) Design, synthesis and properties of acidic deep eutectic solvents based on choline chloride. J Mol Liq 236:338–343. https://doi.org/10.1016/j.molliq.2017.04.052
D’Agostino C, Harris RC, Abbott AP, Gladden LF, Mantle MD (2011) Molecular motion and ion diffusion in choline chloride based deep eutectic solvents studied by 1H pulsed field gradient NMR spectroscopy. Phys Chem Chem Phys 13(48):21383. https://doi.org/10.1039/c1cp22554e
D’Agostino C, Gladden LF, Mantle MD, Abbott AP, Ahmed EI, Al-Murshedi AYM, Harris RC (2015) Molecular and ionic diffusion in aqueous – deep eutectic solvent mixtures: Probing inter-molecular interactions using PFG NMR. Phys Chem Chem Phys 17(23):15297–15304. https://doi.org/10.1039/C5CP01493J
Dai Y, van Spronsen J, Witkamp G-J, Verpoorte R, Choi YH (2013) Natural deep eutectic solvents as new potential media for green technology. Anal Chim Acta 766:61–68. https://doi.org/10.1016/j.aca.2012.12.019
Dai Y, Witkamp G-J, Verpoorte R, Choi YH (2015) Tailoring properties of natural deep eutectic solvents with water to facilitate their applications. Food Chem 187:14–19. https://doi.org/10.1016/j.foodchem.2015.03.123
Delso I, Lafuente C, Muñoz-Embid J, Artal M (2019) NMR study of choline chloride-based deep eutectic solvents. J Mol Liq 290:111236. https://doi.org/10.1016/j.molliq.2019.111236
Du C, Zhao B, Chen X-B, Birbilis N, Yang H (2016) Effect of water presence on choline chloride-2urea ionic liquid and coating platings from the hydrated ionic liquid. Sci Rep 6(1). https://doi.org/10.1038/srep29225
Duarte ARC, Ferreira ASD, Barreiros S, Cabrita E, Reis RL, Paiva A (2017) A comparison between pure active pharmaceutical ingredients and therapeutic deep eutectic solvents: solubility and permeability studies. Eur J Pharm Biopharm 114:296–304. https://doi.org/10.1016/j.ejpb.2017.02.003
Dwamena AK, Raynie DE (2020) Solvatochromic parameters of deep eutectic solvents: effect of different carboxylic acids as hydrogen bond donor. J Chem Eng Data 65(2):640–646. https://doi.org/10.1021/acs.jced.9b00872
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, Landy D, Greige-Gerges H, Fourmentin S (2020a) Cyclodextrins: from solute to solvent. Chem Commun 56:3385−3388. https://doi.org/10.1039/D0CC00460J
El Achkar T, Moura L, Moufawad T, Ruellan S, Panda S, Longuemart S, Legrand F-X, Costa Gomes M, Landy D, Greige-Gerges H, Fourmentin S (2020b) New generation of supramolecular mixtures: characterization and solubilization studies. Int J Pharm:119443. https://doi.org/10.1016/j.ijpharm.2020.119443
Fahri F, Bacha K, Chiki FF, Mbakidi J-P, 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
Fetisov EO, Harwood DB, Kuo I-FW, Warrag SEE, Kroon MC, Peters CJ, Siepmann JI (2018) First-principles molecular dynamics study of a deep eutectic solvent: choline chloride/urea and its mixture with water. J Phys Chem B 122(3):1245–1254. https://doi.org/10.1021/acs.jpcb.7b10422
Florindo C, Oliveira FS, Rebelo LPN, Fernandes AM, Marrucho IM (2014) Insights into the synthesis and properties of deep eutectic solvents based on Cholinium chloride and carboxylic acids. ACS Sustain Chem Eng 2(10):2416–2425. https://doi.org/10.1021/sc500439w
Florindo C, McIntosh AJS, Welton T, Branco LC, Marrucho MI (2018) A closer look into deep eutectic solvents: Exploring intermolecular interactions using solvatochromic probes. Phys Chem Chem Phys 20(1):206–213. https://doi.org/10.1039/C7CP06471C
Florindo C, Branco LC, Marrucho IM (2019) Quest for green-solvent design: from hydrophilic to hydrophobic (deep) eutectic solvents. ChemSusChem 12(8):1549–1559. https://doi.org/10.1002/cssc.201900147
Francisco M, van den Bruinhorst A, Kroon MC (2012) New natural and renewable low transition temperature mixtures (LTTMs): screening as solvents for lignocellulosic biomass processing. Green Chem 14(8):2153–2157. https://doi.org/10.1039/C2GC35660K
Gabriele F, Chiarini M, Germani R, Tiecco M, Spreti N (2019) Effect of water addition on choline chloride/glycol deep eutectic solvents: characterization of their structural and physicochemical properties. J Mol Liq 291:111301. https://doi.org/10.1016/j.molliq.2019.111301
Gao Q, Zhu Y, Ji X, Zhu W, Lu L, Lu X (2018) Effect of water concentration on the microstructures of choline chloride/urea (1:2) /water mixture. Fluid Phase Equilib 470:134–139. https://doi.org/10.1016/j.fluid.2018.01.031
García G, Aparicio S, Ullah R, Atilhan M (2015) Deep eutectic solvents: physicochemical properties and gas separation applications. Energy Fuel 29(4):2616–2644. https://doi.org/10.1021/ef5028873
Germani R, Orlandini M, Tiecco M, Del Giacco T (2017) Novel low viscous, green and amphiphilic N-oxides/phenylacetic acid based deep eutectic solvents. J Mol Liq 240:233–239. https://doi.org/10.1016/j.molliq.2017.05.084
Gomez FJV, Espino M, Fernández MA, Silva MF (2018) A greener approach to prepare natural deep eutectic solvents. Chem Select 3(22):6122–6125. https://doi.org/10.1002/slct.201800713
González CG, Mustafa NR, Wilson EG, Verpoorte R, Choi YH (2018) Application of natural deep eutectic solvents for the “green”extraction of vanillin from vanilla pods. Flavour Fragr J 33(1):91–96. https://doi.org/10.1002/ffj.3425
Gutiérrez MC, Ferrer ML, Mateo CR, del Monte F (2009) Freeze-drying of aqueous solutions of deep eutectic solvents: a suitable approach to deep eutectic suspensions of self-assembled structures. Langmuir 25(10):5509–5515. https://doi.org/10.1021/la900552b
Hadj-Kali MK, Al-khidir KE, Wazeer I, El-blidi L, Mulyono S, AlNashef IM (2015) Application of deep eutectic solvents and their individual constituents as surfactants for enhanced oil recovery. Colloids Surf A Physicochem Eng Asp 487:221–231. https://doi.org/10.1016/j.colsurfa.2015.10.005
Häkkinen R, Willberg-Keyriläinen P, Ropponen J, Virtanen T (2019) Effect of composition and water content on physicochemical properties of choline chloride-boric acid low-melting mixtures. J Mol Liq 280:104–110. https://doi.org/10.1016/j.molliq.2019.02.011
Hammond OS, Bowron DT, Edler KJ (2017a) The effect of water upon deep eutectic solvent nanostructure: an unusual transition from ionic mixture to aqueous solution. Angew Chem Int Ed 56(33):9782–9785. https://doi.org/10.1002/anie.201702486
Hammond OS, Bowron DT, Jackson AJ, Arnold T, Sanchez-Fernandez A, Tsapatsaris N, Garcia Sakai V, Edler KJ (2017b) Resilience of malic acid natural deep eutectic solvent nanostructure to solidification and hydration. J Phys Chem B 121(31):7473–7483. https://doi.org/10.1021/acs.jpcb.7b05454
Haraźna K, Walas K, Urbańska P, Witko T, Snoch W, Siemek A, Jachimska B, Krzan M, Napruszewska BD, Witko M, Bednarz S, Guzik M (2019) Polyhydroxyalkanoate-derived hydrogen-bond donors for the synthesis of new deep eutectic solvents. Green Chem 21(11):3116–3126. https://doi.org/10.1039/C9GC00387H
Hayyan A, Mjalli FS, AlNashef IM, Al-Wahaibi T, Al-Wahaibi YM, Hashim MA (2012) Fruit sugar-based deep eutectic solvents and their physical properties. Thermochim Acta 541:70–75. https://doi.org/10.1016/j.tca.2012.04.030
Hayyan A, Mjalli FS, AlNashef IM, Al-Wahaibi YM, Al-Wahaibi T, Hashim MA (2013) Glucose-based deep eutectic solvents: physical properties. J Mol Liq 178:137–141. https://doi.org/10.1016/j.molliq.2012.11.025
Ibrahim RK, Hayyan M, AlSaadi MA, Ibrahim S, Hayyan A, Hashim MA (2019) Physical properties of ethylene glycol-based deep eutectic solvents. J Mol Liq 276:794–800. https://doi.org/10.1016/j.molliq.2018.12.032
Jani A, Sohier T, Morineau D (2020) Phase behavior of aqueous solutions of ethaline deep eutectic solvent. J Mol Liq 304:112701. https://doi.org/10.1016/j.molliq.2020.112701
Kamlet MJ, Taft RW (1976) The solvatochromic comparison method. I. the .Beta.-scale of solvent hydrogen-bond acceptor (HBA) basicities. J Am Chem Soc 98(2):377–383. https://doi.org/10.1021/ja00418a009
Kamlet MJ, Abboud JL, Taft RW (1977) The solvatochromic comparison method. 6. The .Pi.* scale of solvent polarities. J Am Chem Soc 99(18):6027–6038. https://doi.org/10.1021/ja00460a031
Kareem MA, Mjalli FS, Hashim MA, AlNashef IM (2010) Phosphonium-based ionic liquids analogues and their physical properties. J Chem Eng Data 55(11):4632–4637. https://doi.org/10.1021/je100104v
Kaur S, Gupta A, Kashyap HK (2020) How hydration affects the microscopic structural morphology in a deep eutectic solvent. J Phys Chem B 124(11):2230–2237. https://doi.org/10.1021/acs.jpcb.9b11753
Kim SH, Park S, Yu H, Kim JH, Kim HJ, Yang Y-H, Kim YH, Kim KJ, Kan E, Lee SH (2016) Effect of deep eutectic solvent mixtures on lipase activity and stability. J Mol Catal B Enzym 128:65–72. https://doi.org/10.1016/j.molcatb.2016.03.012
Kumari P, Shobhna, Kaur S, Kashyap HK (2018) Influence of hydration on the structure of reline deep eutectic solvent: a molecular dynamics study. ACS Omega 3(11):15246–15255. https://doi.org/10.1021/acsomega.8b02447
Lapeña D, Lomba L, Artal M, Lafuente C, Giner B (2019) The NADES glyceline as a potential green solvent: a comprehensive study of its thermophysical properties and effect of water inclusion. J Chem Thermodyn 128:164–172. https://doi.org/10.1016/j.jct.2018.07.031
López-Salas N, Vicent-Luna JM, Imberti S, Posada E, Roldán MJ, Anta JA, Balestra SRG, Madero Castro RM, Calero S, Jiménez-Riobóo RJ, Gutiérrez MC, Ferrer ML, del Monte F (2019) Looking at the “water-in-deep-eutectic-solvent” system: a dilution range for high performance eutectics. ACS Sustain Chem Eng 7(21):17565–17573. https://doi.org/10.1021/acssuschemeng.9b05096
Martins MAR, Crespo EA, Pontes PVA, Silva LP, Bülow M, Maximo GJ, Batista EAC, Held C, Pinho SP, Coutinho JAP (2018) Tunable hydrophobic eutectic solvents based on terpenes and monocarboxylic acids. ACS Sustain Chem Eng 6(7):8836–8846. https://doi.org/10.1021/acssuschemeng.8b01203
Martins MAR, Pinho SP, Coutinho JAP (2019) Insights into the nature of eutectic and deep eutectic mixtures. J Solut Chem 48(7):962–982. https://doi.org/10.1007/s10953-018-0793-1
Meng X, Ballerat-Busserolles K, Husson P, Andanson J-M (2016) Impact of water on the melting temperature of urea + choline chloride deep eutectic solvent. New J Chem 40(5):4492–4499. https://doi.org/10.1039/C5NJ02677F
Mitar A, Panić M, Prlić Kardum J, Halambek J, Sander A, Zagajski Kučan K, Radojčić Redovniković I, Radošević K (2019) Physicochemical properties, cytotoxicity, and antioxidative activity of natural deep eutectic solvents containing organic acid. Chem Biochem Eng Q 33(1):1–18. https://doi.org/10.15255/CABEQ.2018.1454
Mjalli FS (2016) Mass connectivity index-based density prediction of deep eutectic solvents. Fluid Phase Equilib 409:312–317. https://doi.org/10.1016/j.fluid.2015.09.053
Mjalli FS, Shahbaz K, AlNashef IM (2015) Modified Rackett equation for modelling the molar volume of deep eutectic solvents. Thermochim Acta 614:185–190. https://doi.org/10.1016/j.tca.2015.06.026
Mulia K, Fauzia F, Krisanti EA (2019) Polyalcohols as hydrogen-bonding donors in choline chloride-based deep eutectic solvents for extraction of Xanthones from the pericarp of Garcinia mangostana L. Molecules 24(3):636. https://doi.org/10.3390/molecules24030636
Nunes RJ, Saramago B, Marrucho IM (2019) Surface tension of dl-menthol:octanoic acid eutectic mixtures. J Chem Eng Data 64(11):4915–4923. https://doi.org/10.1021/acs.jced.9b00424
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(5):1063–1071. https://doi.org/10.1021/sc500096j
Pandey A, Pandey S (2014) Solvatochromic probe behavior within choline chloride-based deep eutectic solvents: effect of temperature and water. J Phys Chem B 118(50):14652–14661. https://doi.org/10.1021/jp510420h
Pandey A, Rai R, Pal M, Pandey S (2013) How polar are choline chloride-based deep eutectic solvents? Phys Chem Chem Phys 16(4):1559–1568. https://doi.org/10.1039/C3CP53456A
Posada E, López-Salas N, Riobóo RJJ, Ferrer ML, Gutiérrez MC, Monte F d (2017) Reline aqueous solutions behaving as liquid mixtures of H-bonded co-solvents: microphase segregation and formation of co-continuous structures as indicated by Brillouin and 1H NMR spectroscopies. Phys Chem Chem Phys 19(26):17103–17110. https://doi.org/10.1039/C7CP02180A
Posada E, Roldán-Ruiz MJ, Jiménez Riobóo RJ, Gutiérrez MC, Ferrer ML, del Monte F (2019) Nanophase separation in aqueous dilutions of a ternary DES as revealed by Brillouin and NMR spectroscopy. J Mol Liq 276:196–203. https://doi.org/10.1016/j.molliq.2018.11.139
Reichardt C (1994) Solvatochromic dyes as solvent polarity indicators. Chem Rev 94(8):2319–2358. https://doi.org/10.1021/cr00032a005
Ribeiro BD, Florindo C, Iff LC, Coelho MAZ, Marrucho IM (2015) Menthol-based eutectic mixtures: hydrophobic low viscosity solvents. ACS Sustain Chem Eng 3(10):2469–2477. https://doi.org/10.1021/acssuschemeng.5b00532
Rodriguez Rodriguez N, van den Bruinhorst A, Kollau LJBM, Kroon MC, Binnemans K (2019) Degradation of deep-eutectic solvents based on choline chloride and carboxylic acids. ACS Sustain Chem Eng 7(13):11521–11528. https://doi.org/10.1021/acssuschemeng.9b01378
Roldán-Ruiz MJ, Jiménez-Riobóo RJ, Gutiérrez MC, Ferrer ML, del Monte F (2019) Brillouin and NMR spectroscopic studies of aqueous dilutions of malicine: determining the dilution range for transition from a “water-in-DES” system to a “DES-in-water” one. J Mol Liq 284:175–181. https://doi.org/10.1016/j.molliq.2019.03.133
Rublova Y, Kityk A, Danilov F, Protsenko V (2020) Mechanistic study on surface tension of binary and ternary mixtures containing choline chloride, ethylene glycol and water (components of aqueous solutions of a deep eutectic solvent, ethaline). Z Phys Chem 234(3):399–413. https://doi.org/10.1515/zpch-2019-1492
Sanchez-Fernandez A, Hammond OS, Jackson AJ, Arnold T, Doutch J, Edler KJ (2017) Surfactant–solvent interaction effects on the micellization of cationic surfactants in a carboxylic acid-based deep eutectic solvent. Langmuir 33(50):14304–14314. https://doi.org/10.1021/acs.langmuir.7b03254
Santana APR, Mora-Vargas JA, Guimarães TGS, Amaral CDB, Oliveira A, Gonzalez MH (2019) Sustainable synthesis of natural deep eutectic solvents (NADES) by different methods. J Mol Liq 293:111452. https://doi.org/10.1016/j.molliq.2019.111452
Savi LK, Carpiné D, Waszczynskyj N, Ribani RH, Haminiuk CWI (2019a) Influence of temperature, water content and type of organic acid on the formation, stability and properties of functional natural deep eutectic solvents. Fluid Phase Equilib 488:40–47. https://doi.org/10.1016/j.fluid.2019.01.025
Savi LK, Dias MCGC, Carpine D, Waszczynskyj N, Ribani RH, Haminiuk CWI (2019b) Natural deep eutectic solvents (NADES) based on citric acid and sucrose as a potential green technology: a comprehensive study of water inclusion and its effect on thermal, physical and rheological properties. Int J Food Sci Technol 54(3):898–907. https://doi.org/10.1111/ijfs.14013
Scientific opinion on safety and efficacy of choline chloride as a feed additive for all animal species (2011) EFSA J 9(9):2353. https://doi.org/10.2903/j.efsa.2011.2353
Shah D, Mjalli FS (2014) Effect of water on the thermo-physical properties of reline: an experimental and molecular simulation based approach. Phys Chem Chem Phys 16(43):23900–23907. https://doi.org/10.1039/C4CP02600D
Shahbaz K, Mjalli FS, Hashim MA, AlNashef IM (2011a) Prediction of deep eutectic solvents densities at different temperatures. Thermochim Acta 515(1):67–72. https://doi.org/10.1016/j.tca.2010.12.022
Shahbaz K, Mjalli FS, Hashim MA, AlNashef IM (2011b) Using deep eutectic solvents based on methyl triphenyl phosphunium bromide for the removal of glycerol from palm-oil-based biodiesel. Energy Fuel 25(6):2671–2678. https://doi.org/10.1021/ef2004943
Shahbaz K, Baroutian S, Mjalli FS, Hashim MA, AlNashef IM (2012a) Densities of ammonium and phosphonium based deep eutectic solvents: prediction using artificial intelligence and group contribution techniques. Thermochim Acta 527:59–66. https://doi.org/10.1016/j.tca.2011.10.010
Shahbaz K, Mjalli FS, Hashim MA, AlNashef IM (2012b) Prediction of the surface tension of deep eutectic solvents. Fluid Phase Equilib 319:48–54. https://doi.org/10.1016/j.fluid.2012.01.025
Shahbaz K, Bagh FSG, Mjalli FS, AlNashef IM, Hashim MA (2013) Prediction of refractive index and density of deep eutectic solvents using atomic contributions. Fluid Phase Equilib 354:304–311. https://doi.org/10.1016/j.fluid.2013.06.050
Silva LP, Fernandez L, Conceição JHF, Martins MAR, Sosa A, Ortega J, Pinho SP, Coutinho JAP (2018) Design and characterization of sugar-based deep eutectic solvents using conductor-like screening model for real solvents. ACS Sustain Chem Eng. https://doi.org/10.1021/acssuschemeng.8b02042
Smith EL, Abbott AP, Ryder KS (2014) Deep eutectic solvents (DESs) and their applications. Chem Rev 114(21):11060–11082. https://doi.org/10.1021/cr300162p
Smith PJ, Arroyo CB, Hernandez FL, Goeltz JC (2019) Ternary deep eutectic solvent behavior of water and urea–choline chloride mixtures. J Phys Chem B. https://doi.org/10.1021/acs.jpcb.8b12322
Tang B, Row KH (2013) Recent developments in deep eutectic solvents in chemical sciences. Monatshefte Für Chem – Chem Month 144(10):1427–1454. https://doi.org/10.1007/s00706-013-1050-3
Teles ARR, Capela EV, Carmo RS, Coutinho JAP, Silvestre AJD, Freire MG (2017) Solvatochromic parameters of deep eutectic solvents formed by ammonium-based salts and carboxylic acids. Fluid Phase Equilib 448:15–21. https://doi.org/10.1016/j.fluid.2017.04.020
Valvi A, Dutta J, Tiwari S (2017) Temperature-dependent empirical parameters for polarity in choline chloride based deep eutectic solvents. J Phys Chem B 121(50):11356–11366. https://doi.org/10.1021/acs.jpcb.7b07754
van Osch DJGP, Zubeir LF, van den Bruinhorst A, Rocha MAA, Kroon MC (2015) Hydrophobic deep eutectic solvents as water-immiscible extractants. Green Chem 17(9):4518–4521. https://doi.org/10.1039/C5GC01451D
Weng L, Toner M (2018) Janus-faced role of water in defining nanostructure of choline chloride/glycerol deep eutectic solvent. Phys Chem Chem Phys 20(35):22455–22462. https://doi.org/10.1039/C8CP03882A
Yusof R, Abdulmalek E, Sirat K, Rahman MBA (2014) Tetrabutylammonium bromide (TBABr)-based deep eutectic solvents (DESs) and their physical properties. Molecules 19(6):8011–8026. https://doi.org/10.3390/molecules19068011
Zhang Q, De Oliveira Vigier K, Royer S, Jérôme F (2012) Deep eutectic solvents: syntheses, properties and applications. Chem Soc Rev 41(21):7108–7146. https://doi.org/10.1039/C2CS35178A
Zhekenov T, Toksanbayev N, Kazakbayeva Z, Shah D, Mjalli FS (2017) Formation of type III deep eutectic solvents and effect of water on their intermolecular interactions. Fluid Phase Equilib 441:43–48. https://doi.org/10.1016/j.fluid.2017.01.022
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2021 The Editor(s) (if applicable) and The Author(s), under exclusive license to Springer Nature Switzerland AG
About this chapter
Cite this chapter
El Achkar, T., Greige-Gerges, H., Fourmentin, S. (2021). Understanding the Basics and Properties of Deep Eutectic Solvents. In: Fourmentin, S., Costa Gomes, M., Lichtfouse, E. (eds) Deep Eutectic Solvents for Medicine, Gas Solubilization and Extraction of Natural Substances. Environmental Chemistry for a Sustainable World, vol 56. Springer, Cham. https://doi.org/10.1007/978-3-030-53069-3_1
Download citation
DOI: https://doi.org/10.1007/978-3-030-53069-3_1
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-030-53068-6
Online ISBN: 978-3-030-53069-3
eBook Packages: Earth and Environmental ScienceEarth and Environmental Science (R0)