129:+ 1-Ethyl-3-methylimidazolium chloride. Type II eutectics are identical to Type I eutectic in composition yet include the hydrated form of the metal halide. Type III eutectics consist of hydrogen bond acceptors such as quaternary ammonium salts (e.g. choline chloride) and hydrogen bond donors (e.g urea, ethylene glycol) and include the class of metal-free deep eutectic solvents. Type III eutectics have been successfully used in metal processing applications such as electrodeposition, electropolishing, and metal extraction. Type IV eutectics are similar to type III yet replace the quaternary ammonium salt hydrogen bond acceptor with a metal halide hydrogen bond acceptor while still using an organic hydrogen bond donor such as urea. Type IV eutectics are of interest for electrodeposition as they produce cationic metal complexes, ensuring that the double layer close to the electrode surface has a high metal ion concentration.
34:. Deep eutectic solvents are highly tunable through varying the structure or relative ratio of parent components and thus have a wide variety of potential applications including catalytic, separation, and electrochemical processes. The parent components of deep eutectic solvents engage in a complex hydrogen bonding network which results in significant freezing point depression as compared to the parent compounds. The extent of freezing point depression observed in DESs is well illustrated by a mixture of
228:
dissolution of biological samples at atmospheric pressure. It is noteworthy that proton-conducting DES (e.g. the mixture of imidazolium methanesulfonate and 1H-1,2,4-triazole in a 1:3 mole ratio or the mixture of 1,2,4-triazolium methanesulfonate and 1H-1,2,4-triazole in a 1:3 mole ratio, wherein the Brønsted base may act as the hydrogen bond donor) have also found applications as proton conductors for fuel cells.
262:
has in recent years published several papers on this topic. He wrote about the use of the solvents for battery recycling from an applied point of view and he also published what may be the first ever serious study of solvent extraction of metals from DES. Foreman has also published two pure research
227:
They were also studied for their applicability in the production and purification of biodiesel, and their ability to extract metals for analysis. Incorporating microwave heating with deep eutectic solvent can efficiently increase the solubility power of DES and reduce the time required for complete
960:
46:
ratio. Choline chloride and urea are both solids at room temperature with melting points of 302 °C (decomposition point) and 133 °C respectively, yet the combination of the two in a 1:2 molar ratio forms a liquid with a freezing point of 12 °C. DESs share similar properties to ionic
1030:
Kareem, Mukhtar A.; Mjalli, Farouq S.; Hashim, Mohd Ali; Hadj-Kali, Mohamed K. O.; Ghareh Bagh, Fatemeh Saadat; Alnashef, Inas M. (1 October 2013). "Phase equilibria of toluene/heptane with deep eutectic solvents based on ethyltriphenylphosphonium iodide for the potential use in the separation of
132:
Wide spread practical use of DESs in industrial process or devices has thus far been hindered by relatively high viscosities and low ionic conductivities. Additionally, lack of understanding of the relationship between parent compound structure and solvent function has prevented development of
974:
Kareem, Mukhtar A.; Mjalli, Farouq S.; Hashim, Mohd Ali; Hadj-Kali, Mohamed K. O.; Bagh, Fatemeh Saadat Ghareh; Alnashef, Inas M. (15 November 2012). "Phase equilibria of toluene/heptane with tetrabutylphosphonium bromide based deep eutectic solvents for the potential use in the separation of
200:
To date, there are numerous applications that have been studied for DES. By varying the components of the DES and their molar ratios, new DES can be produced. For this reason, many new applications are presented in the literature every year. Some of the earliest applications of DES were the
1586:
Rahman, Shahriar Mufid; Mohd Said, Suhana Binti; Subramanian, Balamurugan; Long, Bui Duc; Kareem, Mukhtar A.; Soin, Norhayati (3 August 2016). "Synthesis and
Characterization of Polymer Electrolyte Using Deep Eutectic Solvents and Electrospun Poly(vinyl alcohol) Membrane".
1343:
223:
For this reason, DES were applied as extraction solvents for such material from their complex matrices. DES as extraction solvents in the separation of aromatic hydrocarbons from naphtha was also studied and promising results were published in 2012 and 2013.
1002:
Kareem, Mukhtar A.; Mjalli, Farouq S.; Hashim, Mohd Ali; AlNashef, Inas M. (25 January 2012). "Liquid–liquid equilibria for the ternary system (phosphonium based deep eutectic solvent–benzene–hexane) at different temperatures: A new solvent introduced".
1149:
Ghanemi, Kamal; Navidi, Mohammad-Amin; Fallah-Mehrjardi, Mehdi; Dadolahi-Sohrab, Ali (2014). "Ultra-fast microwave-assisted digestion in choline chloride–oxalic acid deep eutectic solvent for determining Cu, Fe, Ni and Zn in marine biological samples".
1432:
Albler, Franziska-Jane; Bica, Katharina; Foreman, Mark R. StJ.; Holgersson, Stellan; Tyumentsev, Mikhail S. (20 November 2017). "A comparison of two methods of recovering cobalt from a deep eutectic solvent: Implications for battery recycling".
1113:
Habibi, Emadaldin; Ghanemi, Kamal; Fallah-Mehrjardi, Mehdi; Dadolahi-Sohrab, Ali (January 2013). "A novel digestion method based on a choline chloride–oxalic acid deep eutectic solvent for determining Cu, Fe, and Zn in fish samples".
533:
Wilkes, John S.; Levisky, Joseph A.; Wilson, Robert A.; Hussey, Charles L. (March 1982). "Dialkylimidazolium chloroaluminate melts: a new class of room-temperature ionic liquids for electrochemistry, spectroscopy and synthesis".
659:
Dai, Yuntao; van
Spronsen, Jaap; Witkamp, Geert-Jan; Verpoorte, Robert; Choi, Young Hae (22 November 2013). "Ionic Liquids and Deep Eutectic Solvents in Natural Products Research: Mixtures of Solids as Extraction Solvents".
623:
Abbott, Andrew P.; Boothby, David; Capper, Glen; Davies, David L.; Rasheed, Raymond K. (July 2004). "Deep
Eutectic Solvents Formed between Choline Chloride and Carboxylic Acids: Versatile Alternatives to Ionic Liquids".
47:
liquids such as tunability and lack of flammability yet are distinct in that ionic liquids are neat salts composed exclusively of discrete ions. In contrast to ordinary solvents, such as
Volatile Organic Compounds (
1085:
Hayyan, Adeeb; Hashim, Mohd Ali; Hayyan, Maan; Mjalli, Farouq S.; AlNashef, Inas M. (April 2013). "A novel ammonium based eutectic solvent for the treatment of free fatty acid and synthesis of biodiesel fuel".
1255:
Pal, Mahi; Rai, Rewa; Yadav, Anita; Khanna, Rajesh; Baker, Gary A.; Pandey, Siddharth (11 November 2014). "Self-Aggregation of Sodium
Dodecyl Sulfate within (Choline Chloride + Urea) Deep Eutectic Solvent".
1501:
Foreman, Mark R. St J.; Holgersson, Stellan; McPhee, Conor; Tyumentsev, Mikhail S. (29 January 2018). "Activity coefficients in deep eutectic solvents: implications for the solvent extraction of metals".
275:. Lastly, DES involvement in thermoelectrical field was researched through the incorporation of DES in thermoelectric polymer for the synthesis of improved thermoelectric polymer films.
1058:
Hayyan, Maan; Mjalli, Farouq S.; Hashim, Mohd Ali; AlNashef, Inas M. (January 2010). "A novel technique for separating glycerine from palm oil-based biodiesel using ionic liquids".
765:
Dai, Yuntao; van
Spronsen, Jaap; Witkamp, Geert-Jan; Verpoorte, Robert; Choi, Young Hae (March 2013). "Natural deep eutectic solvents as new potential media for green technology".
1381:
Jenkin, Gawen R.T.; Al-Bassam, Ahmed Z.M.; Harris, Robert C.; Abbott, Andrew P.; Smith, Daniel J.; Holwell, David A.; Chapman, Robert J.; Stanley, Christopher J. (March 2016).
434:
Abbott, Andrew P.; Capper, Glen; Davies, David L.; Rasheed, Raymond K.; Tambyrajah, Vasuki (19 December 2003). "Novel solvent properties of choline chloride/urea mixtures".
231:
Owing to their unique composition, DES are promising solvating environments, affecting the structure and self-assembly of solutes. For example, the self-assembly of
716:
Choi, Young Hae; van
Spronsen, Jaap; Dai, Yuntao; Verberne, Marianne; Hollmann, Frank; Arends, Isabel W.C.E.; Witkamp, Geert-Jan; Verpoorte, Robert (August 2011).
818:
Clarke, Coby J.; Tu, Wei-Chien; Levers, Oliver; Bröhl, Andreas; Hallett, Jason P. (24 January 2018). "Green and
Sustainable Solvents in Chemical Processes".
922:
Abbott, Andrew P.; McKenzie, Katy J.; Ryder, Karl S. (2007). "Electropolishing and
Electroplating of Metals Using Ionic Liquids Based on Choline Chloride".
498:
Abbott, Andrew P.; Barron, John C.; Ryder, Karl S.; Wilson, David (27 July 2007). "Eutectic-Based Ionic
Liquids with Metal-Containing Anions and Cations".
235:(SDS) in DES has recently been studied, implying DES can form microemulsions different from those in water. In another case, the solvation of the polymer
141:
Natural deep eutectic solvents (NADES) are bio-based deep eutectic solvents which are composed of two or more compounds that are generally plant based
254:
DES have also been studied for their potential use as more environmentally sustainable solvents for extracting gold and other precious metals from
939:
239:(PVP) in DES is distinct from water, whereby the DES appear to be a better solvent for the polymer. It has been also shown that depending on
1224:
Luo, Jiangshui; Hu, Jin; Saak, Wolfgang; Beckhaus, RĂĽdiger; Wittstock, Gunther; Vankelecom, Ivo F. J.; Agert, Carsten; Conrad, Olaf (2011).
1344:"Nanoscale Clustering of Alcoholic Solutes in Deep Eutectic Solvents Studied by Nuclear Magnetic Resonance and Dynamic Light Scattering"
1291:
Sapir, Liel; Stanley, Christopher B.; Harries, Daniel (19 May 2016). "Properties of Polyvinylpyrrolidone in a Deep Eutectic Solvent".
564:
Abbott, Andrew P.; Al-Barzinjy, Azeez A.; Abbott, Paul D.; Frisch, Gero; Harris, Robert C.; Hartley, Jennifer; Ryder, Karl S. (2014).
1226:"Protic ionic liquid and ionic melts prepared from methanesulfonic acid and 1H-1,2,4-triazole as high temperature PEMFC electrolytes"
259:
267:
issues in DES, in the first he pointed out that activity coefficients in DES do appear to deviate wildly away from their values in
1383:"The application of deep eutectic solvent ionic liquids for environmentally-friendly dissolution and recovery of precious metals"
125:
ionic solvents which were widely studied in the 1980s, such as imidazolium chloroaluminates which are based on mixtures of AlCl
193:, which share many characteristics but are ionic compounds and not ionic mixtures, DES are cheaper to make and sometimes
1462:"Progress towards a process for the recycling of nickel metal hydride electric cells using a deep eutectic solvent"
958:, Richard F. Miller, "Deep eutectic solvents and applications", published 2010, issued Sep 20, 2011
271:
solution while in his later paper he provides a mathematical model for the activity coefficients in DES using the
48:
405:
1624:
718:"Are Natural Deep Eutectic Solvents the Missing Link in Understanding Cellular Metabolism and Physiology?"
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Häkkinen, Riina; Alshammari, Odeh; Timmermann, Vanessa; D’Agostino, Carmine; Abbott, Andrew (2019).
566:"Speciation, physical and electrolytic properties of eutectic mixtures based on CrCl3·6H2O and urea"
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Svigelj, Rossella; Dossi, Nicolò; Grazioli, Cristian; Toniolo, Rosanna (January 2021).
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352:"Metal-Free Deep Eutectic Solvents: Preparation, Physical Properties, and Significance"
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Cen, Peng; Spahiu, Kastriot; Tyumentsev, Mikhail S.; Foreman, Mark R. St. J. (2020).
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467:"Deep Eutectic Solvents: Physicochemical Properties and Gas Separation Applications"
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209:(solubility 0.82 mol/L) have great solubility in DES, and this even includes
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general design rules. Work to understand structure-function relation is on-going.
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GarcĂa, Gregorio; Aparicio, Santiago; Ullah, Ruh; Atilhan, Mert (16 April 2015).
258:. Some solvent extraction work has been done using DES solvents, Mark Foreman at
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197:. Therefore, DES can be used as safe, efficient, simple, and low–cost solvents.
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865:"Deep Eutectic Solvents (DESs) and Their Application in Biosensor Development"
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1531:"Metal extraction from a deep eutectic solvent, an insight into activities"
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Luo, Jiangshui; Tan, Tran Van; Conrad, Olaf; Vankelecom, Ivo F. J. (2012).
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51:), DESs are non-flammable, and possess low vapour pressures and toxicity.
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Smith, Emma L.; Abbott, Andrew P.; Ryder, Karl S. (12 November 2014).
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Gurkan, Burcu; Squire, Henry; Pentzer, Emily (19 December 2019).
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The first generation eutectic solvents were based on mixtures of
39:
1179:"1H-1,2,4-Triazole as solvent for imidazolium methanesulfonate"
214:
255:
173:, being strongly retained in the liquid and which cannot be
73:. DESs are classified into four types based on composition:
926:. ACS Symposium Series. Vol. 975. pp. 186–197.
559:
557:
298:"Deep Eutectic Solvents (DESs) and Their Applications"
201:
electrofinishing of metals using DES as electrolytes.
169:. showed that water can be present as part of the
95:Quaternary ammonium salt + metal chloride hydrate
1589:Industrial & Engineering Chemistry Research
105:Quaternary ammonium salt + hydrogen bond donor
16:Solutions of Lewis or Brønsted acids and bases
115:Metal chloride hydrate + hydrogen bond donor
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1348:ACS Sustainable Chemistry & Engineering
85:Quaternary ammonium salt + metal chloride
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1460:Foreman, Mark R.StJ. (31 December 2016).
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356:The Journal of Physical Chemistry Letters
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121:Type I eutectics include a wide range of
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570:Physical Chemistry Chemical Physics
189:based on discrete anions, such as
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1230:Journal of Materials Chemistry
165:. Work done by Choi, Spronsen
137:Natural deep eutectic solvents
20:Deep eutectic solvents or DESs
1:
1479:10.1080/23312009.2016.1139289
1447:10.1016/j.jclepro.2017.08.135
1435:Journal of Cleaner Production
1360:10.1021/acssuschemeng.9b03771
1100:10.1016/j.indcrop.2013.01.033
1088:Industrial Crops and Products
500:Chemistry: A European Journal
1408:10.1016/j.mineng.2015.09.026
1072:10.1016/j.fuproc.2009.09.002
1017:10.1016/j.fluid.2011.10.024
989:10.1016/j.fluid.2012.07.020
832:10.1021/acs.chemrev.7b00571
662:Journal of Natural Products
368:10.1021/acs.jpclett.9b01980
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1060:Fuel Processing Technology
932:10.1021/bk-2007-0975.ch013
1128:10.1016/j.aca.2012.11.054
1045:10.1016/j.jct.2013.05.046
1031:aromatics from naphtha".
975:aromatics from naphtha".
779:10.1016/j.aca.2012.12.019
415:. University of Leicester
1601:10.1021/acs.iecr.6b01754
1504:New Journal of Chemistry
1313:10.1021/acs.jpca.5b11927
406:"Deep Eutectic Solvents"
436:Chemical Communications
30:and bases which form a
1116:Analytica Chimica Acta
1005:Fluid Phase Equilibria
977:Fluid Phase Equilibria
767:Analytica Chimica Acta
512:10.1002/chem.200601738
233:sodium dodecyl sulfate
956:US Patent 8022014
734:10.1104/pp.111.178426
251:mixtures are formed.
1387:Minerals Engineering
237:polyvinylpyrrolidone
1547:2020PCCP...2211012C
1541:(19): 11012–11024.
1399:2016MiEng..87...18J
1305:2016JPCA..120.3253S
1264:(44): 13191–13198.
1195:2012PCCP...1411441L
1189:(32): 11441–11447.
881:2021Senso..21.4263S
582:2014PCCP...16.9047A
548:10.1021/ic00133a078
536:Inorganic Chemistry
308:(21): 11060–11082.
185:Compared to modern
143:primary metabolites
56:quaternary ammonium
1556:10.1039/C9CP05982B
1516:10.1039/C7NJ03736H
1354:(7): 15086–15092.
1242:10.1039/C0JM04306K
1203:10.1039/c2cp41098b
1164:10.1039/C3AY41843J
591:10.1039/c4cp00057a
471:Energy & Fuels
219:2017-03-04 at the
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1270:10.1021/la5035678
941:978-0-8412-7445-7
890:10.3390/s21134263
674:10.1021/np400051w
668:(11): 2162–2173.
638:10.1021/ja048266j
632:(29): 9142–9147.
576:(19): 9047–9055.
506:(22): 6495–6501.
484:10.1021/ef5028873
362:(24): 7956–7964.
315:10.1021/cr300162p
203:Organic compounds
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813:
788:1887/3193533
770:
766:
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683:1887/3193548
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629:
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573:
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273:SIT equation
253:
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207:benzoic acid
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53:
19:
18:
1441:: 806–814.
1094:: 392–398.
1039:: 138–149.
413:kuleuven.be
245:homogeneous
163:amino acids
1614:Categories
601:2381/37718
325:2381/37428
279:References
175:evaporated
1573:218504859
1393:: 18–24.
1368:201218446
1122:: 61–67.
1011:: 52–59.
983:: 47–54.
773:: 61–68.
392:208643425
211:cellulose
42:in a 1:2
1620:Solvents
1565:32367089
1488:21834215
1329:26963367
1278:25314953
1258:Langmuir
1211:22801556
1136:23327946
909:34206344
850:29300087
805:19255174
797:23427801
752:21677097
692:24188074
646:15264850
610:24695874
520:17477454
452:12610970
384:31804088
334:25300631
265:activity
260:Chalmers
217:Archived
205:such as
181:Research
155:alcohols
101:Type III
1543:Bibcode
1395:Bibcode
1321:1424493
1301:Bibcode
1191:Bibcode
900:8271379
877:Bibcode
869:Sensors
743:3149944
700:5813169
578:Bibcode
419:17 June
376:1608304
171:solvent
145:, i.e.
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81:Type I
67:amines
1569:S2CID
1484:S2CID
1364:S2CID
801:S2CID
696:S2CID
409:(PDF)
388:S2CID
167:et al
61:with
59:salts
24:Lewis
1561:PMID
1325:PMID
1317:OSTI
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1132:PMID
936:ISBN
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421:2014
380:PMID
372:OSTI
330:PMID
161:and
69:and
44:mole
40:urea
38:and
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1413:hdl
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1266:doi
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1160:doi
1124:doi
1120:762
1096:doi
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1013:doi
1009:314
985:doi
981:333
928:doi
895:PMC
885:doi
836:hdl
828:doi
824:118
783:hdl
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771:766
738:PMC
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678:hdl
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596:hdl
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