Processes - Free Full-Text - Recovery of Rare Earth Elements (REEs) Using Ionic Solvents

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Recovery of Rare Earth Elements (REEs) Using Ionic

Solvents  Share
by

Guilhem Arrachart (https://sciprofiles.com/profile/487530) 1,*  (mailto:please_login)
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(https://orcid.org/0000-0002-5277-3967),
Julien Couturier (https://sciprofiles.com/profile/1839226) 1,2  (mailto:please_login),
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
Sandrine Dourdain (https://sciprofiles.com/profile/1733089) 1 
(mailto:please_login), Discuss in

Clément Levard (https://sciprofiles.com/profile/author/K0lyTGRkaXFhVDFmSmROQzdkaU
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2  (mailto:please_login) and (https://scipro

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Processes | Free Full-Text | Recovery of Rare Earth Elements (REEs) ... https://www.mdpi.com/2227-9717/9/7/1202
Stéphane Pellet-Rostaing (https://sciprofiles.com/profile/487773) 1 

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citation_id=115668758)
ICSM, Univ Montpellier, CEA, CNRS, ENSCM, 30207 Marcoule, France
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Aix-Marseille Univ, CNRS, IRD, INRAE, CEREGE, 13545 Aix-en-Provence, France


Author
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to whom correspondence should be addressed.

Processes 2021, 9(7), 1202; https://doi.org/10.3390/pr9071202 (https://doi.org/10.3390
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/pr9071202)

Received: 3 June 2021 / Revised: 21 June 2021 / Accepted: 5 July 2021 /
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Published: 12 July 2021
(This article belongs to the Special Issue Application of Ionic Liquids in Selective
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2 of 98 7/31/2023, 10:05 PM
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Abstract
Rare earth elements (REEs) are becoming more and more significant as they play crucial

Altmetric
roles in many advanced technologies. Therefore, the development of optimized processes for

their recovery, whether from primary resources or from secondary sources, has become
Share
necessary, including recovery from mine tailings, recycling of end-of-life products and urban

and industrial waste. Ionic solvents, including ionic liquids (ILs) and deep-eutectic solvents
(DESs),
Help have attracted much attention since they represent an alternative to conventional
processes for metal recovery. These systems are used as reactive agents in leaching and

extraction
Cite
processes. The most significant studies reported in the last decade regarding the
recovery of REEs are presented in this review.

Keywords:
Discuss in
rare earth elements (/search?q=rare+earth+elements); ionic liquid
(/search?q=ionic+liquid);
SciProfiles deep-eutectic solvent (/search?q=deep-eutectic+solvent);
leaching (/search?q=leaching); extraction (/search?q=extraction); separation
/discussion-
(/search?q=separation)
groups
/public
/10.3390
1. Use and Sourcing of Rare Earths Elements
/pr9071202)
Rare earth elements (REEs) as defined by the International Union of Pure and Applied

Chemistry (IUPAC) include metals characterized by similar properties, namely scandium (Sc),
Endorse
yttrium (Y) and all the lanthanides. The latter correspond to the chemical elements listed in
the periodic table of Mendeleev that have an atomic number ranging from 57 for lanthanum
(La)

to 71 for lutetium (Lu) [1]. REEs are often subdivided into “light rare earths elements”
Comment
(LREEs) and “heavy rare earths elements” (HREEs) according to their atomic numbers.
Yttrium is oftentimes associated with HREEs due to chemical similarities, including ionic radii.
In some cases, the elements from samarium to terbium are considered as the “middle rare
earth elements” (MREEs) [2].
With the increasing uses of these elements, global demand is growing and their access
is becoming crucial, leading to diversified sources of supply (Figure 1).
3 of 98 7/31/2023, 10:05 PM
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
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Share
 Help
 Cite
Figure 1. Use and sourcing of rare earth elements.


Discuss in
The properties of REEs are linked to their electronic configuration and in particular to the
SciProfiles
specificity of their electronic 4f sublayer, which allows numerous optical transitions and gives
them/discussion-
particular magnetic and catalytic properties [3]. REEs are mainly trivalent; however,
groups
different oxidation states can occur naturally for cerium and europium.
/public
Due to these remarkable properties, REEs are used in many high-tech applications [4,5],
/10.3390
such as lasers [6,7], permanent magnets [8,9] energy storage [10,11] and so on. REEs are
/pr9071202)
therefore part of the so-called “technological” metals, the supply of which has become

strategic, as it is threatened by the growth in world demand for these particular metals
[12,13].
Endorse REEs are also considered as “critical” elements by a number of institutions, such as
the EU, which has identified these elements as being of high economic importance with a
high 
risk associated with their supply. The latter includes geopolitical considerations, such as
Comment
the quasi-monopoly over the production of these elements maintained by China.

REEs are commonly mined as co-products or as by-products of other materials. Primary
sources of REEs include hard rock deposits of bastnaesite as well as alluvial deposits of
monazite and xenotime [14]. In addition to these ores, which contain the highest
concentrations of REEs, other mineral resources can be considered, such as phosphate or
apatites, which are admittedly poorer in REEs, but whose exploitation and processing in the
future may be cost-effective [15,16].
Due to the critical need for these materials, alternative sources need to be investigated,
particularly in the context of the circular economy [17,18]. Valorisation of secondary or
unconventional sources becomes more and more relevant, both from economic and
environmental perspectives [19].
REE recovery from industrial landfilled stocks containing lower REE concentrations
requires larger volumes. Among industrial wastes, bauxite residue (red mud) generated
during the production of alumina from bauxite (the Bayer process) represents a promising
source for REEs [20,21]. It is mainly composed of the metallic oxides aluminium, iron and
titanium, as well as up to 1000 ppm of REEs [22,23].
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Like bauxite residue, phosphogypsum, which is a waste generated by the fertilizer

(/)
industry, has been identified as a significant source of REEs due to presence of these
elements and the large volumes generated worldwide [24,25].

Other important secondary sources that are challenging for REE recovery are acid
Altmetric mine
drainages (AMDs) [26] and wastewater sludges [27]. AMD and mine water from operating

andShare
closed mining sites represent a potential secondary source for many elements of
economic interest, including REEs [28]. There is also significant potential for the recovery of

these elements from coal and coal combustion by-products (coal fly ash) and the feasibility
Help
and implementation of industrial processes are under study [29,30].

As REEs are also present in a large amount of technological equipment, recovery from
Cite
recycling of specific wastes, and in particular from waste electrical and electronic equipment
(WEEE), also called urban mines, represents an unconventional and alternative source with
high
 potential
Discuss in [18,31,32]. In this context, much research has recently been performed on end-
SciProfiles
of-life products containing high concentrations of REEs, such as magnets [33,34] or
fluorescent lamps [35,36].
/discussion-
The processes currently used to recover rare earths from these natural or industrial ores
groups
(conventional
/public and unconventional sources) consist in subjecting the ores, which have been
previously
/10.3390crushed, to chemical treatments (with acidic or basic reagents) in order to obtain
/pr9071202)
mineral concentrates. The chemical attack or leaching process is conventionally carried out
by means of one or more acid reagents, including nitric acid, sulphuric acid, phosphoric acid,

hydrochloric
Endorse
acid or a mixture of them (aqua regia). The so-called “pregnant leach solutions”
are then subjected to an extraction/separation step using solvent extraction, ion exchange

and/or precipitation [37].
Comment
Among such separation techniques, solvent extraction or liquid–liquid extraction is the
most commonly used process for the recovery of REEs from the different sources (primary
and secondary mining, waste streams, end-of-life materials and so on). The solvent
extraction process consists in bringing the aqueous phase constituted by the pregnant leach
solution into contact with an organic phase comprising one or more extractants, in order to
achieve an efficient and selective extraction of REEs. Although widely applied on an industrial
scale, liquid–liquid extraction suffers from certain limitations, such as the use of large
amounts of toxic solvents and/or flammable solvents, which are a potential threat to human
health and the environment [38]. For example, aliphatic diluents, such as isooctane, are
classified as highly flammable liquids and vapours with safety concerns (they may be fatal if
they are swallowed and enter the airways, very toxic to aquatic life, etc.), while n-dodecane is
classified as a combustible liquid and can be used as an alternative; however, it also presents
health risks. Another major issue associated with the use of organic solvents in
hydrometallurgy is their loss by evaporation. Besides the economic aspect, this leads to
ecological concerns. Elimination or replacement of hazardous solvents in terms of toxicity and
flammability, which has a clear impact on worker safety and environmental issues, is
therefore one of the main challenges for metallurgical processes.
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2. Description and Properties of Ionic Solvents

(/)
Due(https://www.altmetric.com
to their quasi non-flammability [39] and non-volatility [40,41], ionic solvents,
including ionic liquids (ILs) and deep-eutectic solvents (DESs), are increasingly being used as

Altmetric
alternative diluents or extractants to conventional volatile organic compounds in extraction

processes [42,43]. Recently, the term ‘‘ionometallurgy’’ was introduced by Abbott et al. for
metallurgical
Share
processes using ionic solvents [44]. One of the interesting features of using
ionic solvents is that an electrochemical process for the dissolution and the purification of

metallic
Help species can be implemented thanks to their large electrochemical window [45].
Ionic solvents can be considered as salts with melting points lower than 100 °C [46,47]

and modular physical and chemical properties. Two categories can be considered: the
Cite
“conventional” ILs composed of a discrete cation and anion, and DES systems formed from

an eutectic mixture of Lewis or Brønsted acids and bases, which can contain a diversity of
Discuss in
ionic species (anionic and/or cationic) [48,49,50].
SciProfiles
ILs exhibit a wide variety of chemical structures, but share some common characteristics,
/discussion-
such as bulky organic cations (ammonium, phosphonium, imidazolium, pyridinium,
groups
pyrrolidinium, piperidinium, triazolium) combined with smaller inorganic (chloride,
/public
hexafluorophosphate, tetrafluoroborate, etc.) or organic (acetate, triflate,
/10.3390
bis(trifluoromethyl)sulfonyl imide, etc.) anions (Figure 2).
/pr9071202)

Endorse

Comment
Figure 2. Structures of common cations and anions used in ILs.
Appropriate combinations of the cation and anion allow adjustment of the
6 of 98 7/31/2023, 10:05 PM
physicochemical properties of the ILs (viscosity, density, hydrophilicity and solubility). The
(/)
multiple possibilities make it possible to consider them as “designer solvents” that are
attractive potential alternatives for organic molecular solvents [51].
  to
In conventional approaches applied for metal extraction, ILs are usually hydrophobic
Altmetric
avoid their miscibility in the aqueous phases. Their hydrophobicity is governed by the length

of the
Sharealkyl chain carried by the cation, as well as by the shape, symmetry and the nature of
the anion associated. Typically the applied organic cations present long carbon chains, and

the anions are usually hydrophobic anions such as hexafluorophosphate [PF6−] or
Help
bis(trifluoromethyl)sulfonyl imide [NTf2−]. IL density and viscosity are essential parameters to

take into account in the implementation of an extraction process, as they affect the transport
Cite
properties, such as diffusion [52]. Longer alkyl chain lengths result in lower density and higher
viscosity while, for different anions, these parameters may evolve independently from their

hydrophobicity
Discuss in [53]. Viscosity behaviours have also been assigned to the molecular structure
SciProfiles
of ionic liquids and to the presence of hydrogen bonding and van der Waals interactions [54].
In addition, for an identical cation, ILs based on a weak or non-coordinating anion have a
/discussion-
lower viscosity than those composed of a complexing anion.
groups
Eutectic mixtures are usually considered a new class of ILs and they gained attention
/public
because some of them can be prepared from natural sources, which tends to make them
/10.3390
/pr9071202)
more biodegradable, biocompatible and sustainable [55,56]. In this case, they are defined as
natural DESs (NADESs) [57,58]. DESs usually result from a mixture of compounds that

interact
Endorse
through hydrogen bonding, which leads to charge delocalization resulting in a
depression of the melting point of the mixture [49,59,60,61,62].

A four-group
Comment
classification has been proposed by Abbott et al. based on their
constituents [48,49].
Types I to III DESs can be defined by the general formula Cat+X−·Y−, where:
- Cat+ is usually a quaternary ammonium or phosphonium salt;

- X is the anionic moiety (generally a halide anion);
- Y is a metal chloride for type I, a metal chloride hydrate for type II and a hydrogen bond
donor for type III.
Type IV DESs involve a metal chloride hydrate and hydrogen bond donor.
Most common DESs imply a hydrogen bond donor (HBD) and an ionic hydrogen bond
acceptor (HBA), leading to type III DESs as defined by Abbott et al. [48]. DESs are mainly
hydrophilic mixtures as they are based on at least one ionic species and strong hydrogen
bonding interactions. Most popular DESs are based on quaternary ammonium salts and
choline chloride [63] for their HBA part, and on urea, carboxylic acids, alcohols and glycols for
their HBD. The most common structures of the HBA and HBD are illustrated in Figure 3. As
for the ILs, judicious choices for each component allow the control of parameters such as
density, viscosity, acidity or basicity, hydrophobicity, polarity, volatility and the extractability
7 of 98 7/31/2023, 10:05 PM
properties of the DES.

(/)

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Share
 Help
 Cite

Discuss in
SciProfiles
Figure 3. Structures of some hydrogen bond acceptors (halide salts) and hydrogen
bond donors (amines, alcohols, carboxylic acids) used in the formation of deep-eutectic
/discussion-
solvents.
groups
/public
Among these properties, the acidic character of DESs, also called acidic deep-eutectic
/10.3390
solvents (ADESs), has been highlighted for applications in dissolution, extraction and metal
/pr9071202)
electrodeposition [60]. The acidity of ADESs can be controlled with the acidity of the HBD and

these DESs are often divided into two classes: Brønsted and Lewis DESs.
Endorse
Also, since 2015, with the concept of hydrophobic deep-eutectic solvents (HDESs)

proposed by van Osch et al. [64], interest in the synthesis and application of HDESs is
Comment
strongly increasing [65,66,67]. It is assumed that the hydrophobic character depends on the
hydrophobicity of the components forming the DES. HDESs are mainly type III, involving
bulky quaternary ammonium or phosphonium halide ILs as HBAs and hydrophobic carboxylic
acids as HBDs. This trend for hydrophobic eutectic mixtures was recently investigated for
mixtures solely composed of non-ionic species [68,69]. A fifth class of DES has therefore
been proposed to complete the Abbott classification so that it includes such fully organic
hydrophobic eutectic solvents involving strong interaction between a hydrogen bond donor
and a hydrogen bond acceptor [70]. These type V non-ionic DESs represent a relatively new
class of eutectics which have strong potential for the recovery of REEs through solvent
extraction.
3. Use of ILs and DESs for the Recovery of REEs
3.1. Leaching Processes

Conventional leaching processes are based on the use of strong mineral acids
(sulphuric, nitric or hydrochloric) as well as alkali media (such as ammonia or sodium
hydroxide), despite their poor selectivity and adverse effects for the environment and health.
8 of 98 7/31/2023, 10:05 PM
In this regard, ionometallurgy appears as an interesting alternative that deserves to be further

(/)
explored. In particular, DESs and ILs have been shown to be good solvents for metal oxides
[71,72,73,74,75]. Few examples of DES and IL systems have been proposed for the

dissolution
Altmetric of materials that incorporate REEs (Table 1).
The solubility of metal oxides, including rare earth oxides (REOs), has been studied

using
ShareILs such as betaine bis(trifluoromethylsulfonyl)imide ([Hbet] [NTf2]). [Hbet] [NTf2] is a
weak Brønsted acidic ionic liquid due to the carboxyl group attached to its cation. The

formation of a carboxylate complex between the carboxylic acid group of the ionic liquid and
Help
the metal oxides allows the dissolution of metal oxides, which is favoured by the presence of

water in the IL phase [76].
Cite
Such an [Hbet] [NTf2] ionic liquid has been applied for the leaching of bauxite residue in
order to perform a selective dissolution of REEs against iron [77]. In aqueous solution, the

betainium
Discuss in cation exhibits the necessary acidity (higher acidity (pKa = 1.83) than acetic acid
SciProfiles
(pKa = 4.75)) for the metals’ dissolution, as well as complexing properties for the metals’
complexation.
/discussion-It has been found that the temperature is a key parameter: the efficiency is
much more pronounced when dissolution is carried out at temperatures above 100 °C.
groups
Another application of [Hbet] [NTf2] highlighted is its role as part of the selective leaching
/public
for /10.3390
the recovery of REEs from iron in NdFeB permanent magnets [78]. The useful effect of the
/pr9071202)
roasting of NdFeB permanent magnets, which makes it possible to avoid the formation of the
insoluble ternary NdFeO3 phase, was supported by leaching with an aqueous solution

containing
Endorse
the ionic liquid [Hbet] [NTf2] [79]. The same research group showed that the use of
protic ionic liquids, such as pyridine hydrochloride (PyHCl), at high temperature (165 °C)

allows the leaching of NdFeB magnets and then the recovery of the REEs by solvent
Comment
extraction [80].
DES also have excellent dissolution properties due to their capacity to accept/donate
protons or electrons to form hydrogen bonds [49,59]. The leaching behaviour of bastnaesite-
type deposits, which are the main source of rare earths, was investigated using choline–
chloride-based deep-eutectic solvents [81]. For this purpose, single-salt and multicomponent
mineral mixtures of REEs (Y, La, Ce, Nd and Sm) in their carbonate form were studied.
Dissolution experiments have shown that the DESs based on [choline chloride
(ChCl):malonic acid (MA)] and [choline chloride (ChCl):urea + malonic acid mixture (UMA)]
display higher performances in dissolving REEs. Bastnaesite ore was therefore subjected to
a dissolution step using [ChCl:UMA], highlighting a potential DES system for selective
dissolution of heavy REEs in comparison to light REEs and competitive elements resulting
from the gangue minerals, such as Ca, Mg and Fe.
Dissolution of REOs has been investigated using a series of Brønsted acidic DESs
based on polyols and organic acids [82]. Among the DESs studied, the [ethylene glycol
(EG):maleic acid (Maleic) (4:1)] system was highlighted as the optimal solvent due to its
strong acidity and low viscosity. Notable differences in the solubilities of REOs have been
observed, with considerable solubilization ability identified for the LREEs (except for CeO2)
9 of 98 7/31/2023, 10:05 PM
and MREEs in comparison to the HREEs, which allows the consideration of their separation.
(/)
Thesolubility and separation of REE oxides and salts were also recently demonstrated by
(https://www.altmetric.com
Söldner et al. [75,83] for various DESs.

 Ithas
NdFeB magnet leachates have also been studied with a deep-eutectic solvent.
Altmetric
been shown that the complete dissolution of NdFeB magnets can be performed with [choline

chloride
Share (ChCl):lactic acid (LAC) (molar ratio 1:2)], while the dissolution is not observed in the
case of [ChCl:urea] or [ChCl:ethylene glycol] [84].


It was assumed that the protons present in the lactic acid could react with the metal
Help
oxides to dissolve them, and that the coordinating abilities of lactic acid and of choline may

have favoured this dissolution. After the complete dissolution, liquid–liquid extraction was
Cite
applied to separate the REEs from Fe, Co and B and to separate Dy from Nd in a second
step.

In a similar approach, a recovery process for simulated NdFeB permanent magnets was
Discuss in
SciProfiles
proposed using [guanidine hydrochloride (GUC):lactic acid (LAC)]. Such DESs exhibit a high
selectivity for the dissolution of Nd in comparison to Fe. Starting from a mixture of Nd2O3 and
/discussion-
Fe2groups
O3 with a mole ratio of 1:7, it was found that 95% of Nd can be dissolved while less than
1%/public
could be for Fe [85]. The particular interest of this application has also been
demonstrated
/10.3390 through a patent which is based on the use of the choline chloride/lactic acid
/pr9071202)
system, thus showing the maturity of such a process for the recovery of REEs from NdFeB
magnets [86].

Beyond permanent magnets, other end-of-life products, such as fluorescent lamps, have
Endorse
been studied using chloride-based DESs and [Hbet] [NTf2] ionic liquid. In this case, a [choline

chloride:levulinic acid (LevA) (1:3)] system was found to be appropriate for the solubility of the
Comment
phase containing the REEs, such as red phosphor Y2O3:Eu3+ (YOX) against halophosphate
phosphor (Sr,Ca)10(PO4)(Cl,F)2:Sb3+, Mn2+ (HALO), which does not contain any REEs [87].
Extraction of REEs from the loaded lixiviant DES phase was also examined and showed that
metal recovery was possible via solvent extraction, thus allowing the recycling of the DES.
The [Hbet] [NTf2] efficiency for the oxide dissolution was valued for lamp phosphor waste with
the selective dissolution of YOX without dissolving the other phosphors, such as the green
phosphor LaPO4:Ce3+, Tb3+ (LAP), the blue phosphor BaMgAl10O17:Eu2+ (BAM) or
halophosphate phosphor (HALO) [88]. Also, as an alternative to conventional sulphuric acid
leach, the recovery of REEs from waste phosphor can be performed after their leaching in
1-methylimidazolium hydrogen sulphate [C1Him] [HSO4] and by oxalic acid precipitation [89].
Coal and coal combustion by-products have been studied as potential sources of REEs.
The dissolution of coal in ILs has been recently reviewed [90] and the possibility of recovering
REEs has been investigated using an IL and a DES, respectively 1-butyl-3-methylimidazolium
chloride [C1C4im] [Cl] and a mixture of choline chloride:urea (molar ratio 1:2) [91].
Due to the low melting points of these ionic solvents, they can be used as undiluted or
low-dilution leaching agents, which is very different from conventional mineral acid solutions.
It implies new mechanisms that are, for now, still not well understood or mastered.
10 of 98 7/31/2023, 10:05 PM
Irrespective of the hydrophobic or hydrophilic character of the ionic solvent, water content
(/)
seems to be a critical point for all the systems, influencing the viscosity, the dissolution rate,
the selectivity and even the triggering or the inhibiting of the mechanisms, depending on the
Moreover, these low water content ionic systems change the nature of the  
situation.
Altmetric pregnant
leach solution, which therefore strongly affects the following steps of the metal recovery

compared
Share to conventional processes [80,84,87].
 Help
Table 1. Overview of ionic solvent for REE leaching.
 Cite

Discuss in
SciProfiles
3.2.(https://sciprofiles.com
Solvent Extraction Processes
/discussion-
As mentioned before, solvent extraction or liquid–liquid extraction is the most commonly
groups
used process for the recovery of rare earth elements after the leaching step.
/public
Since the pioneering work of Dai et al. [92] highlighting the potential of ILs for solvent
/10.3390
extraction in the context of metal recovery, many studies have been developed showing their
/pr9071202)
potential in terms of efficiency in comparison to classical organic solvents [93].

As already mentioned, solvent extraction exploits the different distribution of a solute
Endorse
between two immiscible liquids. In most cases, the pregnant leach solutions, which contain

the REEs to be extracted, are in an aqueous phase that makes contact with the hydrophobic
Comment
ILs, leading to the formation of biphasic systems [94].
Some hydrophobic ILs that are immiscible with nonpolar organic solvents can also be
engaged in triphasic extraction systems and are named water/organic solvents/ILs [95].
Moreover, water-miscible ILs can also form two-phase systems with aqueous solutions in the
presence of kosmotropic ions, which contribute to the stability and structure of water–water
interactions, such as K3PO4, K2CO3 and Na2S2O3 in the aqueous solution. The hydrophilic
ILs can thus be separated from the aqueous phase and be further re-used [96].
Ionic liquid-based aqueous biphasic systems (IL-ABSs) are also encountered as systems
for the extraction and separation of different metal species but much more marginally
compared to triblock copolymer-based ABSs [97].
In conventional solvent extraction, as the hydrated metallic cations tend to stay in the
aqueous solution, extractants are usually required in the organic phase to form complexes
with the metal and increase its hydrophobicity. This therefore favours the transfer of the
metallic ions from the aqueous phase to the hydrophobic IL phase.
It has been highlighted that, in some cases, the solvation of extractant–metal complexes
is more thermodynamically favoured in ILs than in conventional organic solvents. [92] This
property is a major advantage of using ILs for metal ion extractions since in many cases they
11 of 98 7/31/2023, 10:05 PM
exhibit significantly higher extraction performance and improved metal selectivity than
(/)
conventional solvents [98]. Consequently, IL-based extraction systems have been prepared
using several extractants or synergistic systems diluted in ILs, or by using task-specific ionic
 orthe
liquids
Altmetric(TSILs), which refer to ILs that incorporate the extracting moieties into the cation
anion of the ionic liquid.


In conventional diluents, solvent extraction mechanisms are based on the molecular and
Share
supramolecular interaction properties of the extractant molecule aggregates due to their


amphiphilic nature. This aptitude has also been demonstrated for the IL-based organic phase
Help
[99].

Usually, the extraction mechanisms in an IL differ considerably from those in traditional
Cite
organic diluents [100,101]. ILs are capable of solubilizing neutral or charged complexes, while
only neutral species (or neutral ion pairs) are extracted in conventional solvents. These

extraction
Discuss in modes and mechanisms are based on the principle of electroneutrality. Therefore,
SciProfiles
if charged species are extracted in the IL phase, they have to be counterbalanced in the
aqueous phase. Depending on the aqueous leach solutions, the nature of the extractant and
/discussion-
of groups
the IL involved in the extraction systems, various mechanisms can therefore be
encountered,
/public such as ion exchange, when the cations or anions of ILs might be transferred
into/10.3390
the aqueous phase during extraction; neutral extraction; or neutral coextraction
/pr9071202)
[102,103]. Three main kinds of molecular mechanisms have been identified when ionic liquids
are used as extraction diluents. Taking as an example an extractant in an imidazolium-type
ionic  liquid, these mechanisms are illustrated within the Figure 4 and can be described as
Endorse
follows:

Comment
Figure 4. Schematic representation of mechanisms encountered in IL-based extraction

systems.
- Neutral extraction mechanism: A neutral complex is formed and extracted in the IL phase.
This mechanism is similar to those encountered in conventional solvents; however, the
detailed mechanisms are often different. In this extraction mode, the IL acts as a polar non-
aqueous solvent [104];
- Cation exchange: This extraction mode is specific to IL systems. The IL acts as a liquid ion
exchanger with cationic complexes extracted from the aqueous phase into the IL phase.
Consequently, an IL cation has to be transferred to the aqueous phase while, in exchange, a
12 of 98 7/31/2023, 10:05 PM
metallic cation is transferred to the IL phase to respect electroneutrality [105];

(/)
- Anion exchange: This extraction mode is also specific to IL systems. An anionic extractant
forms over-neutralized anionic complexes that can be transferred to the IL phase, in
isless
exchange
Altmetric for the transfer of an IL anion to the aqueous phase [106]. Anion exchange
common than cation exchange.
Share
In comparison with the extraction behaviours of conventional organic systems, the

mechanism in IL-based extraction systems exhibits high complexity. In some cases, the IL-
based
Help
systems involve polyvalent metals and cationic or anionic extractants or polyvalent ILs
can be encountered, which leads to mixed extraction mechanisms.

Ion-exchange mechanisms are the main drawback of the IL-based extraction systems,
Cite
since a part of the IL is lost in the aqueous phase and can be considered as sacrificial. The

main factor influencing this exchange mechanism is the solubility in the aqueous phase of the
Discuss in
IL SciProfiles
component. It has been shown that hydrophobic cations can moderate these exchanges,
whereas the phenomenon is increased with hydrophilic anions [107,108]. The increase of the
/discussion-
hydrophobicity, such as the alkyl chain length of the IL cation, can lead to a switchover of the
groups
mechanism from ion exchange to neutral complex extraction [109]. Aqueous phase acidity
/public
has also been shown to play a role in the ion-exchange mechanisms of some systems [110].
/10.3390
3.3./pr9071202)
IL-Based Extraction Systems for REE Recovery
Many systems, including cation exchangers (Table 2) and neutral extractants (Table 3),

as well as synergistic systems (Table 4), have been studied for the recovery of REEs and
Endorse
have shown their potential in common solvents. This is why the feasibility of using these

various
Comment
systems has been implemented within the framework of IL-based extraction for the
recovery of REEs [111,112]. Applications of mixtures of ILs and molecular extractants in metal
solvent extraction technology have been recently reviewed by Wang et al. [113].
3.3.1. Ionic Exchangers
The cationic exchangers may exhibit a function with an acidic character (possessing a
labile proton), such as carboxylic (diglycolamic acid), phosphoric (HDEHP: bis (2-
ethylhexyl)phosphoric acid), phosphonic (PC-88A: 2-ethylhexylphosphonic acid mono-2-
ethylhexyl ester) and phosphinic (Cyanex-272: bis(2,4,4-trimethylpentyl) acids), or they may
function as chelating extractants, such as beta-diketone (HTTA: 2-thenoyltrifluoro acetone,
HBA: benzoylacetone). In these cases, metal ions are complexed by the conjugate bases.
Among these extractants, numerous studies have been dedicated to the use of the beta-
diketone HTTA in imidazolium-based IL ([C1Cnim] [NTf2]) [114,115,116,117,118]. Since the
work of Jensen et al. with HTTA in ILs showing the presence of anionic lanthanide complexes
in [C1C4im] [NTf2] [106], comprehensive investigations of REE extraction have suggested the
unusual extraction mechanisms of such ionic exchangers. Anionic lanthanide complexes are
made possible by the exchange of the ionic liquid anions into the aqueous phase for the
lanthanide complex at high HTTA concentrations, while at lower concentrations, Ln3+ was
13 of 98 7/31/2023, 10:05 PM
extracted as a neutral Ln(TTA)3 complex.

(/)
Eu(https://www.altmetric.com
3+ chelation with HTTA into [C C im] [NTf ] has been investigated with time-resolved
1 n 2
laser-induced fluorescence spectroscopy (TRLFS) and highlighted that a mixture of neutral
  of
Eu(TTA) −
Altmetric
3 and anionic Eu(TTA)4 complexes can be encountered [114]. The stoichiometry
extracted complexes, such as the Ln(TTA)4− anionic complex, was confirmed by emission

profiles
Share and spectrophotometric titration respectively for Eu3+/HTTA and Nd3+/HTTA
complexes [115]. The role of the IL anion with regard to Ln chelates and the extraction

mechanism has been evidenced for the bis(trifluoromethanesulfonyl)imide anion (NTf2) [116],
Help
as well as nonafluoro-1-butanesulfonate (CF3(CF2)3SO3−) [117]. The efficiency of HTTA has

thus been demonstrated for various REEs [118];
Cite
other beta-diketones, such as
benzoylacetone (HBA), also show the interest of this type of extractant. This aptitude for REE
extraction has also been studied within the implementation of synergistic systems in

combination
Discuss in with neutral extractants.
SciProfiles
The feasibility for the selective recovery of REEs using [C1C8im] [NTf2] with DODGAA as
extractant has been demonstrated with sulphuric and nitric acid solutions [119,120].
/discussion-
The extraction performance of DODGAA in [C1C4im] [NTf2] for REEs (Y, La, Ce, Eu and
groups
Tb)/public
with an acidic leach solution of phosphor powders coming from waste fluorescent lamps
was/10.3390
examined and demonstrated selective extraction toward metal impurities such as Fe, Al
and/pr9071202)
Zn for both leaching nitric and sulphuric acid solutions [121].
Recently, solvent impregnated resins (SIRs) based on DODGAA and [C1C4im] [NTf2]
have  been developed for extraction chromatography of lanthanides [122], as well as for the
Endorse
recovery of REEs from leach solutions of thin film phosphors [123]. Another diglycolamic acid

(HDEHDGA) has been studied by Rout et al., confirming the potential of this type of
Comment
extractant in ionic liquid media such as tetraoctylammonium dodecyl sulphate, [N8888] [DS]
[124] or methyltrioctylammonium bis (trifluoromethanesulfonyl)imide ([N1888] [NTf2]) [125].
Despite Cyanex-272 and HDEHP being widely used as metal extractants, there are only
a few studies reporting their use in the context of IL-based extraction systems for REE
recovery. Cocalia et al. [104] have studied these extractants and described identical
extraction behaviour and coordination of f-element cations using 1-decyl-3-methylimidazolium
bis(trifluoromethanesulfonyl)imide ([C1C10im] [NTf2]) and n-dodecane. Other studies have
shown their potential in various ionic liquid diluents, such as [C1Cnim] [NTf2] and [C1Cnim]
[BETI] (n = 4–10) [126], or compared to diglycolamic acid extractant [124,125]. In some cases
the conjugate bases of acidic and chelating extractants have been used to replace the IL
anion in order to develop TSIL (see below).
Stripping from the extraction phase is an important aspect to take into consideration.
REE extraction efficiency often depends on acid feed concentration, which usually allows the
stripping of some REEs by playing with the pH. The stripping can be attributed partly to a lack
of dissociation of the chelating extractant or protonation of the acidic extractant. Indeed, for
acidic extractants, the extraction ability usually decreases for high acidic concentrations in the
feed solution. REEs can therefore be stripped from the ionic phase by strongly acidic
14 of 98 7/31/2023, 10:05 PM
solutions. The stripping percentage can be gradually increased by increasing the acidity of
(/)
the stripping phase.
The efficiency of the stripping is also related to the affinity of the extracting phase for the
cases,

metal. Indeed, with greater affinities, the back-extraction will be more difficult. In some
Altmetric
complex-forming agents, such as ethylenediaminetetraacetic acid (EDTA) and


diethylenetriaminepentaacetic
Share acid (DTPA), need to be added to the aqueous stripping phase.
With regard to the reuse of the ionic phase, it must generally undergo an additional

clean-up step (a scrubbing step with a base, for example) in order to deprotonate the acidic
Help
extractant engaged in the ionic based-extraction system.

Table 2. Examples of acidic and chelating extractants in ILs for the recovery of REEs.
Cite

Discuss in
SciProfiles
/discussion-
groups
/public
3.3.2. Neutral Extractants
/10.3390
A typical neutral extractant has donor groups (O, S, P, N) without labile hydrogen. The
/pr9071202)
extractant (a hydrophobic Lewis base) acts through its donor power, giving rise to interactions

of the acceptor–donor type with the neutral metal species of the aqueous phase. The
Endorse
extracted species is solvated in an electrically neutral molecular form.

The most widely used solvating compounds are the neutral organophosphorus
Comment
derivatives, including phosphines, phosphine oxides, phosphinates, phosphonates and
phosphates. The extraction of neutral metal complexes by solvation is performed through
their O-donor character [127]. This ability for the extraction and separation of REEs has also
been examined in ILs.
Tri-n-octylphosphine oxide (TOPO) was engaged with [C1Cnim] [NTf2] (n = 4, 8) for the
extraction of REEs from a nitrate medium, showing the importance of the cation of the IL in
the extraction mechanism. REEs were extracted through the exchange of the metal ion and
the imidazolium cations of the IL. In addition, for the IL-based TOPO extraction systems, an
inversion of selectivity for the REEs was observed in comparison to an organic solvent such
as n-dodecane, which can be explained by the difference in the coordination sphere [128].
Cyanex 923, which is a mixture of four trialkylphosphine oxides, exhibits extraction
properties similar to TOPO. Cyanex 923 has been used in ionic liquid phases for the
extraction of REEs from nitric acid medium using ILs containing a
bis(trifluoromethylsulfonyl)imide anion ([C1C4im] [NTf2], [N1444] [NTf2] and [P66614] [NTf2])
[129], while nitrate ILs, such as trioctylmethylammonium nitrate ([N1888] [NO3]) and
trihexyl(tetradecyl)phosphonium ([P66614] [NO3]), were employed for concentrated chloride
aqueous solutions [130].
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Acquisition of these results led to the implementation of a process in continuous mode

(/)
for the (https://www.altmetric.com
separation of Dy and Nd from chloride media using Cyanex 923 diluted in [P66614]
[SCN] [131].
  in
Tri-n-butyl phosphate (TBP) is widely used for metal recovery. It has been employed
Altmetric
[N1888] [NO3] for the recovery of REEs from an aqueous nitrate phase from spent Nd-Fe-B

magnets
Share [132].
This possibility has also been investigated for Pr(III), Nd(III) and Dy(III) in aqueous phase

containing a bis(trifluoromethyl-sulfonyl)amide anion with the aim of undertaking
Help
electrodeposition after their extraction by TBP in triethyl-pentyl-phosphonium [P2225] [NTf2]. A

combination ion-pair and cation-exchange mechanism was observed and the direct
Cite
electrodeposition of the extracted [Nd(TBP)3]3+ in the TBP IL-based system was
demonstrated [133].

The efficiency and selectivity of REE(III) extraction from chloride media has also been
Discuss in
SciProfiles
demonstrated using the neutral extractant octyl(phenyl)-N,N-diisobutyl-
carbamoylmethylphosphine
/discussion- oxide (CMPO) in [C1C4im] [NTf2] [134,135]. A CMPO IL-based
system ([C1C4im] [PF6]) has been previously used for the recovery of REEs from nitrate
groups
aqueous
/public solution with an enhancement in the efficiency in comparison to conventional
organic solvents [136].
/10.3390
/pr9071202)
Moreover, the usual neutral organophosphorus derivatives, phosphoryl-containing
podands, have been also investigated for REE recovery from a nitric acid, such as

triphosphine
Endorse
trioxide (TPO) [137] in N-butyl, N-octyl-N-ethylpiperidinium
bis(trifluoromethylsulfonyl)imide [C2C4Pip] [NTf2] or [C2C8Pip] [NTf2], or diethyl 2-

[(diphenylphosphoryl)methoxy]-5-ethylphenylphosphonate [138] in [C1C4im] [NTf2].
Comment
Diglycolamides (DGAs), with their tridentate O-donating ligands, have the ability to form
stable complexes with lanthanides and actinides. Therefore, diglycolamide-based systems in
IL have been investigated for the recovery of such metals [139]. It was found that N,N,N′
,N′-tetraoctyl diglycolamide (TODGA) allows the enhancement of the extraction performance
for REEs when it is diluted in [C1C4im] [NTf2] in comparison to an isooctane system.
Significant differences were observed in the extraction mechanisms, since a cation-exchange
mechanism is involved for the TODGA-ILs systems while it is ion pair extraction in isooctane.
Also, a difference in the selectivity was noticed, with a preference for MREEs in the ILs
systems and HREEs in the isooctane system [140]. A kinetics study of metal transfer (Eu3+)
from a nitric solution to a TODGA- [C1C4im] [NTf2] phase showed that it depends on the nitric
acid and TODGA concentrations [141].
The possibility of transferring REEs from a Cl− aqueous phase was investigated using
the systems TODGA- [C1C4im] [NTf2] [135] and TODGA- [N1114] [NTf2], or TODGA-
[C1C4Pyro] [NTf2], by studying the solvation of REEs with electronic absorption spectroscopy
[142]. Murakami et al. [143] studied the possibility of using a TODGA- [P2225] [NTf2] system
to recover REEs from an aqueous phase containing a bis(trifluoromethyl-sulfonyl)amide anion
with a similar approach as in their study with TBP- [P2225] [NTf2] [133].
16 of 98 7/31/2023, 10:05 PM
Other studies have focused on REE complexation by diglycolamides in [C1C8im] [NTf2],

(/)
showing that DGA ligands are bonded with the metal ion in a tridentate fashion via 2 carbonyl
O/details.php?domain=www.mdpi.com&
atoms and one etheric O atom, as observed in organic solvent [144]. Also, a high loading
 with
of Altmetric
metals is possible without third phase formation, contrary to what can be observed
molecular diluents [145]. Similarly, other DGAs have been used, such as N,N′-dimethyl-

N,N′-dioctyl-3-oxadiglycolamide
Share (DMDODGA) in [C1C4im] [NTf2] [146]. The use of DGAs has
been studied by taking advantage of their preorganization on macrocyclic platforms, such as

calix [4]arene. As demonstrated in other studies, DGA-based extraction systems result in
Help
different behaviours in ILs with regard to the efficiency and selectivity for REEs [147].

There are on-going studies investigating the use of malonamide as part of an IL-based
Cite
extracting system for the recovery of REEs, with a focus on the molecular and
supramolecular mechanisms involved in such systems [148,149].

As already discussed, stripping is an important step to consider for the recovery of REEs
Discuss in
SciProfiles
and the reusability of the ionic phase. As neutral extractants are able to extract acids,
stripping can be performed by using a high acidic stripping phase. Promoting the extraction of
/discussion-
acidgroups
in the ionic phase allows the release of metals extracted from this phase.
The mechanism of the stripping reaction is attributed to exchange of REE ions with
/public
protons in the ionic phase. However, the presence of acid in the ionic phase can have a
/10.3390
impact; for systems with an NTf2− anion, this leads to the formation of triflimide
/pr9071202)
negative
(HNTf2), which is partially lost in the aqueous stripping phase due to its high solubility in
water.
Endorse

Comment
Table 3. Examples of neutral extractants in ILs for the recovery of REEs.
3.3.3. Combination of Extractant and Synergistic Systems

As mentioned above, many studies have demonstrated remarkable favourable changes,
in terms of extraction mechanisms, efficiency and selectivity, for a variety of IL-based systems
[150]. These extractants can also be used in combination to achieve, under certain
conditions, synergistic systems in which the interactions of the two extractants produce a
better effect than the sum of their individual effects. In some cases, the term “synergism” is
used when the extractants are engaged in a simple combination to improve their efficiency or
selectivity in cooperative ways. Synergistic mixtures of extractants, for which improvements of
extraction efficiency have been demonstrated in organic solvents, have been studied in IL-
based systems.
Taking into account the efficiency of beta-diketone (HTTA) and benzoylacetone (HBA),
17 of 98 7/31/2023, 10:05 PM
these extractants have been combined or engaged in synergistic systems with different
(/)
neutral extractants, such as TOPO or CMPO.
Accordingly, we can notably cite the systems HTTA-TOPO [151,152,153,154], HBA-
  in
TOPO
Altmetric[154,155], HTTA-CMPO [156] and HBA-CMPO [157], which have all been diluted
various [C1Cnim] [NTf2].


A combination of neutral extractants has also been investigated and demonstrated that
Share
the addition of TBP to a TODGA- [C1C8im] [NTf2] system makes it possible to increase the

efficiency for REE extraction [145], while a TODGA-CMPO mixture in [C1Cnim] [NTf2] phases
Help
highlighted antagonism behaviour in the transfer of REEs (Ce, Eu and Lu) from Cl− aqueous

solutions [135]. Recently, the selective separation of Gd(III) from Sm(III) in a nitric acid
Cite
solution was described in the presence of a mixture of organophosphorus extractants (TBP-
Cyanex 272 or TBP-HDEHP) in the [C1C6im] [PF6] [158].

Discuss in
Table 4. Examples of combinations of extractants in ILs for the recovery of REEs.

SciProfiles
/discussion-
groups
/public
/10.3390
/pr9071202)

3.3.4. Task-Specific Ionic Liquids (TSILs)
Endorse
As they refer to ILs that incorporate a chelating site, TSILs combine the properties of

ionic liquids with those of conventional extracting compounds [159]. TSILs can therefore act
Comment
both as the organic phase as well as the extracting agent, avoiding the difficulties that can be
encountered through extractant/solvent miscibility. Extraction experiments have thus been
performed using undiluted TSILs or diluted in an IL. The incorporation of functional groups,
which act as complexation sites for the REEs, can be undertaken on the anionic or cationic
parts of the IL.
• TSILs with functionalized anion (Table 5)
TSILs with functionalized anions usually exhibit an anionic chelation site, which has
strong coordinating properties for the REEs. REEs can be coordinated by anions with
complexation abilities, such as thiocyanate [SCN−] or nitrate [NO3−], as demonstrated by
various studies from Binnemans’ research group. These studies are mainly focused on
recycling processes, such as the recovery of REEs from magnets [160,161], batteries [162]
and fluorescent lamp waste [163]. Also, the conventional IL anion can be replaced by an
anionic extractant.
HDEHP is certainly one of the most useful and efficient acidic extractants. However
despite the ability of ILs to solubilize a wide range of solutes, it appears that HDEHP is poorly
soluble in these media [164].
18 of 98 7/31/2023, 10:05 PM
To overcome such a drawback, the extractant has been engaged as an anion in various
(/)
systems.
TSIL The extraction behaviour of neodymium(III) from a nitrate medium was studied
using 1-hexyl-3-methylimidazolium bis(2-ethylhexyl)phosphate ([C1C6im] [DEHP]), 1-hexyl-

[DEHP])  
1-methylpyrrolidinium
Altmetric bis(2-ethylhexyl)phosphate ([C1C6pyr] and
tetrabutylammonium bis(2-ethylhexyl)phosphate ([N4444] [DEHP]), diluted in their

corresponding
Share bis(trifluoromethylsulfonyl)imide IL [165]. Sun et al. studied various DEHP-type
ionic extractants with ammonium (tetrabutylammonium [N4444], tetraoctylammonium [N8888])

or phosphonium (trihexyl(tetradecyl)phosphonium [P66614]) cations diluted in [C1Cnim] [NTf2]
Help
or [C1Cnim] [BETI]. Higher REE extraction performances were obtained in ILs with better

solubilities and stabilities for REE complexes in comparison to organic solvents
Cite
[166,167,168]. It has been highlighted that the driving force of DEHP-based TSIL extraction
systems is mainly ion interaction rather than ion exchange. Also, DEHP-based TSILs have
been
 used
Discuss in in a synergistic extraction using Cyanex 923 as molecular extractant, which made
SciProfiles
it possible to increase the efficiency of the separation of middle to heavy REEs (Eu3+, Dy3+,
Er3+) from light REEs (La3+) [169].
/discussion-
Recently, more and more studies have described the use of Cyphos® IL 104 as an
groups
extracting
/public phase. This phosphonium-based ionic liquid [P66614] uses Cyanex 272 as part of
the /10.3390
anion of the IL.
/pr9071202)
Solvent extractions of Y from chloride and nitrate solutions were investigated with this
TSIL and compared to ammonium-based ionic liquids [N1888] with Cyanex 272 as an anion

[170]. Other studies have shown the efficiency of such systems for various REEs from various
Endorse
feed solutions [171,172]. Also, it has been shown that Cyphos® IL 104 can be used for the

separation of rare earths, with an ionic liquid [C1C2im] [Cl] phase allowing an ionic liquid–ionic
Comment
liquid extraction system, for the recycling of valuable metals from nickel metal hydride (NiMH)
batteries [173].
Other phosphorous acidic extractants have been considered as anionic species for the
development of TSILs, such as 2-ethylhexyl phosphoric acid mono(2-ethylhexyl) ester, which
is named P507 or PC-88A. As an example, the extraction of mid-heavy REEs from H2SO4
media has been highlighted using [N1888] [P507] [174]. In some cases, the TSIL is used as
an extractant that can be diluted in organic solvent. This was proposed by Dutta et al. [175]
for the liquid–liquid extraction of gadolinium from a nitric acid medium to an organic phase
consisting of [N1888] [P507] extractant dissolved in n-dodecane.
As shown in different studies, beta-diketones are also widely used for the recovery of
REEs. They have been studied as anions for the implementation of TSIL-based extraction
systems [176,177]. This extractant was used for the application of a homogeneous liquid–
liquid extraction process involving a hexafluoroacetylacetone [hfac] as anion in an IL-based
system involving [Ch] [hfac] and [Ch] [NTf2]. Extraction of Nd(III) was performed by taking
advantage of [Ch] [NTf2] thermomorphic behaviour in water and of the formation of an anionic
tetrakis(hexafluoroacetylacetonato)Nd(III) complex, with a choline cation as counter ion. It
was accompanied by an ion exchange of three choline ions from the IL phase to the aqueous
19 of 98 7/31/2023, 10:05 PM
phase [177].
(/)
Other coordinating anions have also been considered, such as diglycolamate or
carboxylate anions. A TSIL based on trioctylmethylammonium dioctyl diglycolamate [N1888]


[DGA]
Altmetricdiluted in [N
1888] [NO3] was proposed for the recovery of Nd(III), and it showed good
extraction properties from nitrate media in comparison to chloride media [178]. Undiluted

tetraoctylphosphonium
Share oleate [P8888] [oleate] was used as a bifunctional extractant for the
recovery of metals from an aqueous chloride feed solution [179]. The separation of transition

metals from REEs was considered by adjusting the chloride concentration and pH.
Help
In addition, the potential of ionic liquids exhibiting a carboxylic acid group on their anion

has been shown in various studies. Sec-Octylphenoxy acetic acid (CA-12) and sec-
Cite
nonylphenoxy acetic acid (CA-100) have been applied in combination with
trioctylmethylammonium as the bifunctional ionic liquid extractants [N1888] [CA-12] and

[NDiscuss
1888] in [CA-100] for the selective extraction of La(III) from REEs into a chloride medium
SciProfiles
[180].
The same system has been involved for the extraction of REEs from a nitrate medium
/discussion-
[181]. In a similar approach, the feasibility of a selective extraction of Y(III) from a chloride
groups
medium was demonstrated using a [N1888] [CA-12] system [182], with an improvement in the
/public
efficiency
/10.3390and phase separation when tri-n-butyl phosphate (TBP) was used as a phase
/pr9071202)
modifier [183]. Another example that can be cited is the use of benzoate anion in
phosphonium-based ionic liquid in the context of Nd(III) extraction from an aqueous solution

of NdCl
Endorse3
with and without hydrochloric acid (HCl) [184].
Synergistic extraction strategies have been proposed using TSILs with functionalized

anions, such as mixtures of [N1888] [CA-12] and Cyphos® IL 104 for HREE separation from
Comment
chloride solution [185].
Table 5. Examples of TSILs with functionalized anions for the recovery of REEs.
• TSILs with a functionalized cation (Table 6)
A great variety of functional groups have been incorporated onto the cation of ILs, mainly
hard base oxygen derivatives, since REEs are considered hard acids according to Pearson’s
HSAB concept.
TSILs bearing a carboxylic group have been proposed, such as hydrophobic [1-alkyl-
3-(1-carboxylpropyl)im] [PF6], which requires saponification to be considered for the
extraction of yttrium [186]. Chen et al. described a pH-controlled selective separation of
Nd(III) from Fe(III) by using carboxyl-functionalized imidazolium ionic liquids
20 of 98 7/31/2023, 10:05 PM
[C1(CH2)nCOOHim] [NTf2] (n = 3, 5, 7) as the solvent and complexing agent [187]. Taking

(/)
advantage of carboxylic acids for the extraction of REEs, a carboxyl-functionalized
phosphonium IL [P444C1COOH]Cl showed good extraction properties for scandium in an

aqueous
Altmetric biphasic system (ABS) [188]. Betaine incorporates a carboxylic acid.
This functional cation, which was originally developed for the dissolution of metal oxides

[76],Share
has been also used for the extraction and recovery of REEs. Many examples of IL-
based systems using [Hbet] [NTf2] can be cited [189,190,191]. Homogeneous liquid−liquid

extraction was implemented on the basis of the significant solubility in water and the
Help
thermomorphic behaviour of [Hbet] [NTf2]. The [Hbet] [NTf2]/water mixture exhibits an upper

critical solution temperature (UCST) of 55 °C [190]. The extraction efficiency of the
Cite
zwitterionic betaine has been highlighted for various REEs and applications [78,88,192,193].
Other Brønsted acids can be also encountered; Dupont et al. have reported the use of ILs

incorporating
Discuss in sulfonic acid (-SO3H) [194], alkylsulfuric acid (-OSO3H) [195] and N-alkylated
SciProfiles
sulfamic acid (NH–SO3) [196].
Neutral extractants have also been immobilized on ILs cations. Most TSILs containing
/discussion-
neutral extractants have been studied for the partitioning of actinides/lanthanides [197]. As
groups
mentioned
/public above, CMPO was used as the extractant in ILs for the extraction of REEs;
moreover,
/10.3390ILs with grafted CMPO moieties have been synthesized and used for the extraction
/pr9071202)
of Ln [198,199,200].
Phosphoryl-based TSILs, involving the introduction of coordinating P=O groups on the IL

cations,
Endorse
were found to help Nd(III) ion extraction [201].
Solvent extraction experiments have indicated the possibility of extracting Eu(III) with

diglycolamide-functionalized task-specific ionic liquids, as shown in a study of the Eu3+–DGA-
Comment
TSIL complex in [C1C4im] [NTf2] [202]. In contrast, Yun et al. indicated that no Ln can be
extracted by using a diglycolamide-grafted imidazolium IL in [C1C6im] [NTf2]. It has been
suggested that TSILs suppress the extraction of lanthanides because of the formation of
water-soluble complexes [203].
Table 6. Examples of TSILs with a functionalized cation for the recovery of REEs.
4. Outlook—Open Questions and Needed Research
Ionic solvents offer an interesting alternative to the various conventionally used organic
solvents and extractants and acid or alkali leaching solutions. Indeed, such systems can be
used independently as solvents for the solvent leaching and extracting phases in the recovery
21 of 98 7/31/2023, 10:05 PM
of metallic species; these methods are part of the so-called “ionometallurgy” process.
(/)
However, in the case of REE recovery, few studies report both leaching and extraction
steps using ionic solvents [80,84]. Indeed, changes in pregnant leach solution using DESs or

ILsAltmetric
affect extraction and separation possibilities and can lead to emerging non-aqueous
processes, introduced as “solvometallurgy” by Binnemans and Jones [204]. The following

sections
Share provide an overview of the potential of iono-/solvo-metallurgy for REE recovery,
including the identification of potential gaps that need to be further explored.

4.1. Help
Future of Leaching
Using ionic solvents during the leaching step often shows lower dissolution properties but
 selectivities
higher Cite toward targeted metals compared to the use of strong mineral acid
solutions that dissolve the entire matrix. Such solvents could particularly be appropriated for

low-grade REE resources, like mine tailings or industrial wastes, since complete leaching
Discuss in
requires large amounts of chemicals and energy in these cases. Moreover, partial
SciProfiles
decomposition of the matrix by ionic solvents should theoretically reduce the difficulty and/or
the /discussion-
number of steps during liquid–liquid extraction and then reduce the impact of recovery. In
groups
the best-case scenarios, we can imagine that the extraction step could be suppressed by
/public
efficient selective leaching. However, REE speciation in secondary sources is often
/10.3390
overlooked. A better consideration of chemical speciation of REEs coupled with a good
/pr9071202)
characterization of the hosting matrices would help in identifying the proper IL or DES system

for leaching selectivity.
Endorse
In addition, a concern to take into account in the context of the use of ionic solvents as
leaching agents is that some of them can remain in the leaching residues, which implies the
need

to clean the solid residue.
Comment
4.2. Future of Liquid–Liquid Extraction

The number of studies involving IL-based extracting systems for the recovery of REEs is
constantly increasing. Many studies have focused on imidazolium-based cations with
hydrophobic anions, including PF6− and NTf2−, but more recent studies involve other types of
cations, such as ammonium or phosphonium. Khazalpour et al. published a recent review
focused on phosphonium-based ionic liquid PILs for various applications, including ion
extraction and, therefore, REE recovery [205].
Recent studies rely on the use of ionic liquid-based aqueous biphasic systems (IL-ABS)
to avoid having to resort to hydrophobic ILs, which are mainly based on fluorinated anions
that are expensive and present a significant environmental impact. Currently, the use of this
type of IL-ABS system is not well-reported for the recovery of REEs [206], except for a few
examples [207,208].
In the majority of the studies for the recovery of REEs, DESs are involved in the leaching
process but not as extracting phases. Hydrophobic DESs (HDESs) demonstrated promising
results as extracting phases for the extraction and separation of metallic elements
22 of 98 7/31/2023, 10:05 PM
[209,210,211,212,213]. However, REE recovery has not been studied apart from a recent
(/)
 showing
study the potential of HDES for recovery of waste SmCo magnets [214]. Also, non-
ionic hydrophobic eutectics should be considered, as recent studies have proposed a

  of
hydrophobic
Altmetric eutectic solvent-based on TOPO as an extractant for liquid–liquid separation
uranyl nitrate from aqueous acid [215] or platinum group and transition metals in HCl media
[216].
Share
In addition, emphasis should be placed on intra-rare earth separation. A recent review


devoted to this issue showed that high selectivities can be obtained when separating LREEs
Help
from HREEs; however, the separation between adjacent REEs requires more attention [217].

4.3. Electrochemical Behaviour
Cite
Beyond their efficiency for the extraction of REEs, ionic solvents can also be used for the

electroleaching [218] or electrodeposition of metals from non-aqueous electrolytes [44,219].
Discuss in
Electrodeposition of REEs cannot be performed in aqueous solutions because the
SciProfiles
electropositivity of these metals is greater than that of hydrogen, but ILs can provide suitable
/discussion-
conditions for their electrodeposition [220]. Therefore, the electrochemical behaviour of
groups
various IL systems and REEs have been investigated [221,222,223,224]. Zhang et al. [225]
/public
recently described the application of non-haloaluminate ILs as solvents for low-temperature
/10.3390
electrodeposition of REEs.
/pr9071202)
Although electroleaching has been demonstrated for different metals using ionic

solvents, there are only a few studies focused on REEs. Further research on this topic should
Endorse
therefore be further considered.

4.4. Mechanism and Predictive Models
Comment
Another open question concerns the mechanisms involved in ionic solvents, which are
not fully described in most of the studies on this topic. Comprehension and prediction of
solvent extraction in ionic solvents would help in identifying a priori which ionic solvent can be
used to transpose the extractant systems known in conventional solvents to ionic solvents.
Transposition from conventional diluents to ionic solvents would therefore become more
straightforward and less expensive for industrial actors.
Recent studies have been undertaken focused on supramolecular mechanisms and the
formation of aggregates [149]. In addition, the contributions of modelling and theoretical
chemistry are important to take into account in order to better understand these mechanisms
and acquire predictable models.
To render the application of ILs in solvent extraction predictable and reliable, it is
therefore of crucial importance to understand their impact in the solvent extraction
mechanisms. Specifically, it is also of prime industrial importance to use non-sacrificial ILs, for
which it is necessary to be able to predict why and with which ILs ion exchange may occur or
not.
4.5. Industrial Applications and Prospects
23 of 98 7/31/2023, 10:05 PM
Although the performances and expectations are significant, the feasibility of these
(/)
experiments when transferred from the laboratory scale to the pilot or even industrial levels is
not well addressed in the various studies. One of the often reported drawbacks for ILs is their
 The
cost. Their recyclability and non-volatility make it possible to reduce the cost of use.
Altmetric
recovery of the extracted REEs and the recycling of the ionic phase are important in industrial

separation
Share processes. However, this point is not always investigated in detail in most studies.
It is important to further investigate the stripping of REEs from the loaded ionic phase, as well

as, in some cases, the scrubbing of the ionic phase before reusing it in new extracting steps.
Help
The limitations of these processes should be taken into account, such as the loss of ionic

liquid through ionic exchange in some of the systems examined. This phenomenon can be
Cite
slightly mitigated by changing the pH [110] but, in practice, ion exchange is often attenuated
by increasing the hydrophobic character of the ILs: by acting on the anion nature or on the

length
Discuss ofin the cation chains. This latter possibility generally leads to an increase in viscosity.
SciProfiles
The viscosities of the ionic liquids used in the extraction processes are indeed relatively high
compared to the viscosities of water and traditional organic solvents, which may have an
/discussion-
impact
groupson the mixing, phase transfer and separation. They can also be reduced by using
suitable
/publicIL mixtures [226]. The industrial applications of some ILs [227] may also be limited
due/10.3390
to other characteristics, such as corrosiveness, hygroscopicity and, in some cases,
/pr9071202)
toxicity.
The industrial applications of ionic liquids are steadily increasing in many sectors [228]: a

pre-commercial
Endorse
permanent magnet recycling plant for REE recovery was opened in 2018 by
Seren Technologies Limited, based on patents from Nockemann’s group at Queen’s

University Belfast [229,230], and a pilot-scale plant for rare earth ore separation is currently
Comment
being built.
The rise of DESs is also moving in this direction since they involve lower viscosities and
cheaper precursors than the ILs, making technical considerations for the implementation of
industrial process less restrictive [231]. It appears that the application of DESs for the
recovery of REEs could address some of the existing challenges of ionic liquids.
4.6. Environmental Impact
The low pressure of ionic liquid vapours is often considered a major advantage of ionic
liquids from an environmental point of view, and these liquids are considered as
environmentally friendly alternatives to volatile organic solvents. However, the toxicity of
these ionic systems must be considered [232,233]. It has been shown that the overall toxicity
of ILs depends on both their cation—and particularly the cation alkyl chain length—and anion
parts [234,235]. It seems important to take into account these factors when implementing IL-
based extracting systems and choosing the cation and anion. Once again, this tends to
encourage the use of DESs and, more particularly, NADESs. Indeed, DESs are usually
known to be less toxic and more biodegradable than ILs [236]. However, statements about
DESs’ low toxicity are based on the low toxicities of their individual components; however,
24 of 98 7/31/2023, 10:05 PM
DESs are not necessarily as low in toxicity as their constituents. The toxicities of their
(/)
mixtures must be taken into account [237].
Given the importance of REEs in various advanced technologies and the potential of
solvent recovery processes highlighted in various studies, investigation of such  

ionic
Altmetric systems,
and particularly DES systems, should continue to grow.
Share
Funding

The
Help authors acknowledge the financial support from the CNRS through the MITI
interdisciplinary programs (PRIME 2020: ExtraMet project), the Agence Nationale de la

Recherche
Cite
through the RECALL project (ANR-20-CE04-0007), the SILEXE project (ANR-13-
CDII-0010) and the Labex Project CheMISyst (ANR-10-LABX-05-01).

Discuss in
Conflicts of Interest
SciProfiles
The authors declare no conflict of interest.
/discussion-
groups
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%0ARecovery%20of%20Rare%20Earth%20Elements%20%28REEs
%29%20Using%20Ionic%20Solvents%0A%0AAbstract
%3A%20Rare%20earth%20elements%20%28REEs
%29%20are%20becoming%20more%20and%20more%20significant%20as%20they%20
play%20crucial%20roles%20in%20many%20advanced%20technologies.%20Therefore
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Arrachart, G.; Couturier, J.; Dourdain, S.; Levard, C.; Pellet-Rostaing, S. Recovery of Rare
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Processes - Free Full-Text - Recovery of Rare Earth Elements (REEs) Using Ionic Solvents

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Recovery of Rare Earth Elements (REEs) Using Ionic

2  (mailto:please_login) and (https://scipro

Stéphane Pellet-Rostaing (https://sciprofiles.com/profile/487773) 1 

Aix-Marseille Univ, CNRS, IRD, INRAE, CEREGE, 13545 Aix-en-Provence, France

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Figure 1. Use and sourcing of rare earth elements.

the quasi-monopoly over the production of these elements maintained by China.

Like bauxite residue, phosphogypsum, which is a waste generated by the fertilizer

2. Description and Properties of Ionic Solvents

Figure 2. Structures of common cations and anions used in ILs.

Appropriate combinations of the cation and anion allow adjustment of the

- Cat+ is usually a quaternary ammonium or phosphonium salt;

properties of the DES.

3. Use of ILs and DESs for the Recovery of REEs

3.1. Leaching Processes

In this regard, ionometallurgy appears as an interesting alternative that deserves to be further

Söldner et al. [75,83] for various DESs.

case of [ChCl:urea] or [ChCl:ethylene glycol] [84].

anion of the ionic liquid.

supramolecular interaction properties of the extractant molecule aggregates due to their

Figure 4. Schematic representation of mechanisms encountered in IL-based extraction

metallic cation is transferred to the IL phase to respect electroneutrality [105];

extracted as a neutral Ln(TTA)3 complex.

complex-forming agents, such as ethylenediaminetetraacetic acid (EDTA) and

Acquisition of these results led to the implementation of a process in continuous mode

Other studies have focused on REE complexation by diglycolamides in [C1C8im] [NTf2],

3.3.3. Combination of Extractant and Synergistic Systems

various [C1Cnim] [NTf2].

Table 4. Examples of combinations of extractants in ILs for the recovery of REEs.

using 1-hexyl-3-methylimidazolium bis(2-ethylhexyl)phosphate ([C1C6im] [DEHP]), 1-hexyl-

carboxylate anions. A TSIL based on trioctylmethylammonium dioctyl diglycolamate [N1888]

• TSILs with a functionalized cation (Table 6)

[C1(CH2)nCOOHim] [NTf2] (n = 3, 5, 7) as the solvent and complexing agent [187]. Taking

4. Outlook—Open Questions and Needed Research

4.2. Future of Liquid–Liquid Extraction

ionic hydrophobic eutectics should be considered, as recent studies have proposed a

In addition, emphasis should be placed on intra-rare earth separation. A recent review

solvent recovery processes highlighted in various studies, investigation of such  

2. Rollinson, H.R. Using Geochemical Data: Evaluation, Presentation, Interpretation;

12. Alonso, (/)

16. Khan, (/)

20. Rivera, (/)

23. Evans, (/)

%E2%80%93331&doi=10.1007/s40831-016-0060-x)] [CrossRef (https://doi.org

26. León, (/)

30. Rybak, (/)

pages=142&doi=10.3390/met11010142)] [CrossRef (https://doi.org/10.3390

37. Gupta, (/)

49. Smith, (/)

61. Abbott, (/)

64. van Osch,