Choline derivative ionic liquids-based aqueous two-phase systems: Phase diagrams and partition of purine alkaloids

Jiao, Ren; Li, Zhiyong; Liu, Jing; Pei, Yuanchao; Wang, Jianji

doi:10.1016/j.jct.2017.10.017

Cited by 30 publications

(7 citation statements)

References 62 publications

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“…Furthermore, these solvents have been categorized as nontoxic . CAAILs have been successfully employed in ATPSs, a type of liquid–liquid extraction, to isolate bioactive molecules, pollutants (such as naphthalene, pyrene, or caffeine , ), or triazine-based herbicides . Other cholinium-based ILs have also been employed in partition studies: three pollutants (o-cresol, o-xylene, and acetonitrile) were extracted from aqueous mixtures using the IL [choline][NTf 2 ], and an ATPS containing choline chloride proved to be suitable for the removal and concentration of two commonly used drugs (ibuprofen and diclofenac) …”

Section: Introductionmentioning

confidence: 99%

Removal of Acetaminophen (Paracetamol) from Water Using Aqueous Two-Phase Systems (ATPSs) Composed of Choline-Amino Acid Ionic Liquids

Barroca,

Velho,

Macedo

2023

J. Chem. Eng. Data

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Emerging contaminants, such as pharmaceutical compounds, are often bioaccumulative and can have toxic effects on the environment; therefore, there is a need to find efficient techniques to extract these hazardous species from water bodies. In this work, five aqueous two-phase systems (ATPSs) composed of choline-amino acid ionic liquids (CAAILs) and phosphate salts were studied to remove acetaminophen (a common active pharmaceutical ingredient, API), constituting a sustainable extraction approach. The CAAILs cholinium L-alaninate ([Ch][Ala]), cholinium glycinate ([Ch][Gly]), cholinium leucinate ([Ch][Leu]), and cholinium Lserinate ([Ch][Ser]) were successfully synthesized, and their chemical structures were confirmed by infrared spectroscopy and density measurements. Partitions of acetaminophen were performed in the systems {[Ch][Ala] or [Ch][Gly] or [Ch][Ser] (1) + K 2 HPO 4 (2) + water (3)} and {[Ch][Ala] or [Ch][Leu] (1) + K 3 PO 4 (2) + water (3)}, at 298.15 K and 0.1 MPa. Of these, four ATPSs showed good results in the extraction of acetaminophen: {[Ch][Ala] or [Ch][Gly] (1) + K 2 HPO 4 (2) + water (3)} and {[Ch][Ala] or [Ch][Leu] (1) + K 3 PO 4 (2) + water (3)}. Acetaminophen migrated preferentially to the top (IL-rich) phase, obtaining partition coefficients (K) higher than unity and extraction efficiencies (E) larger than 90%. The most promising extraction efficiencies (E) were attained for the largest tie-line lengths (TLLs) of {[Ch][Ala] or [Ch][Gly] (1) + K 2 HPO 4 (2) + water (3)}, with E = 97.5% for TLL = 82.18 m % and E = 79.3% for TLL = 85.05 m %, respectively, while {[Ch][Ala] or [Ch][Leu] (1) + K 3 PO 4 (2) + water (3)} only obtained E = 97.9% for TLL = 75.35 m % and E = 97.50% for TLL = 85.23 m %, respectively.

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Section: Introductionmentioning

confidence: 99%

Removal of Acetaminophen (Paracetamol) from Water Using Aqueous Two-Phase Systems (ATPSs) Composed of Choline-Amino Acid Ionic Liquids

Barroca,

Velho,

Macedo

2023

J. Chem. Eng. Data

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“…The azobenzene-based ILs were synthesized using the procedures described in our previous work, and their chemical structures (Figure ) were confirmed by 1 H NMR (Supporting Information). Then, binodal curves of each azobenzene-based IL surfactant + inorganic salt (K 2 CO 3 , K 3 PO 4 , K 2 HPO 4 , or KOH) + water system were determined before and after UV irradiation by the cloud point titration method according to the procedures described in the literature, , and the results are shown in Figures and S2, and S3. The binodal data for the ATPSs are given in Tables S2–S9 (Supporting Information).…”

Section: Resultsmentioning

confidence: 99%

“…Binodal curves of the azobenzene-based ILs + inorganic salts + water systems were determined by the cloud point titration method according to the procedures described in the literature. , Briefly, a known concentration of an aqueous azobenzene-based IL solution was added in a test tube at 25.0 °C, and a salt solution of a known mass fraction was then added dropwise until the mixture became turbid, then a known mass of water was added to make the mixture clear again. This procedure was repeated to obtain sufficient data for the building of a liquid–liquid equilibrium binodal curve.…”

Section: Experimental Sectionmentioning

confidence: 99%

Light-Triggered Switchable Ionic Liquid Aqueous Two-Phase Systems

Li¹,

Feng²,

Liu

et al. 2020

ACS Sustainable Chem. Eng.

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Aqueous two-phase systems (ATPSs) consist of two immiscible aqueous phases where the mole fraction of water in both upper and bottom phases is higher than 0.8. ATPS has been widely used in many different fields since its discovery in 1896. However, easy control of phase transition is highly desired in many cases, which is still a challenge. Herein, we report the first work for the reversible switching of transition between two-phase ATPSs and single phase solution by light irradiation. It was found that azobenzene-based ionic liquids and inorganic salts in water systems could be reversibly switched between two-phase ATPS and homogeneous solution at ambient conditions by alternatively UV and visible light irradiation.Mechanism studies reveal that cationic isomerization of the azobenzene-based ionic liquids and size change of their micelles by UV and visible light irradiation is the main driving force for such reversible phase transition of ATPSs. This unique phase behavior has bridged the gap between ATPSs and chemical reactions, which is useful to create new chemistry in ATPSs. As an example of applications, highly efficient and selective aza-Michael reactions were performed in this novel kind of switchable ATPSs, which was well integrated with heterogeneous product 2 separation, and the phase components could be easily reused. This work opens a new way to conduct reactions efficiently with easy separation process.

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“…On the one hand, the hydrophilic and hydrophobic properties of ILs affect their phase forming ability. For example, Ren et al used five ILs to construct ATPS with K 3 PO 4 , K 3 C 6 H 5 O 7 , and K 2 CO 3 [ 86 ]. The results showed that phase forming ability of ILs increased with the increase in their hydrophobicity.…”

Section: Mechanism Of Phase Separationmentioning

confidence: 99%

Phase Behavior of Ionic Liquid-Based Aqueous Two-Phase Systems

Zheng

Yao

et al. 2022

IJMS

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As an environmentally friendly separation medium, the ionic liquid (IL)-based aqueous two-phase system (ATPS) is attracting long-term attention from a growing number of scientists and engineers. Phase equilibrium data of IL-based ATPSs are an important basis for the design and optimization of chemical reactions and separation processes involving ILs. This article provides the recent significant progress that has been made in the field and highlights the possible directions of future developments. The effects of each component (such as salting-out agents and ILs) on the phase behavior of IL-based ATPSs are summarized and discussed in detail. We mainly focus on the phase behavior of ATPSs by using ILs, expecting to provide meaningful and valuable information that may promote further research and application.

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Choline derivative ionic liquids-based aqueous two-phase systems: Phase diagrams and partition of purine alkaloids

Cited by 30 publications

References 62 publications

Removal of Acetaminophen (Paracetamol) from Water Using Aqueous Two-Phase Systems (ATPSs) Composed of Choline-Amino Acid Ionic Liquids

Removal of Acetaminophen (Paracetamol) from Water Using Aqueous Two-Phase Systems (ATPSs) Composed of Choline-Amino Acid Ionic Liquids

Light-Triggered Switchable Ionic Liquid Aqueous Two-Phase Systems

Phase Behavior of Ionic Liquid-Based Aqueous Two-Phase Systems

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