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CHEMICAL ENGINEERING RESEARCH & DESIGN · 2017 · IF 2.538

Ether-functionalized ionic liquids: Highly efficient extractants for hordenine

Yunchang Fan,Xiaojing Li,Lei Zhang,Peigao Duan,Feifei Li,Dan Zhao,Yuan Wang,Hongwei Wu

The application of ether-functionalized ionic liquids (ILs) as alternatives to conventional organic solvents in liquid-liquid extraction of hordenine was investigated. The parameters affecting the extraction ability of ILs such as the pH of the aqueous phase, the chemical structures of the IL cation and anion, the phase volume ratio and the hordenine concentration were evaluated. Experimental results indicate that the ether-functionalized ILs possess stronger extraction ability than the dialkylimidazolium-based ones. The extraction efficiency is highly dependent on the pH of the aqueous phase. Driving forces underlying the extraction processes include hydrogen-bonding interaction, hydrophobic interaction and steric hindrance effect. The recovery of hordenine from the IL phase and the recycling of the IL phase can be realized by using the pH swing effect. These results suggest that the ether-functionalized ILs are ideal alternatives to the conventional organic solvents for the extraction of hordenine from aqueous phases.

CAS / MDL: 109-65-9 67-56-1
研究领域: 化学工程 · 药物化学 · 分离科学
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JOURNAL OF MOLECULAR LIQUIDS · 2021 · IF 6.165

Study of apparent molar volumes of ether functionalized ionic liquids with three ether solvents

Qingshan Liu,Jiamin Chu,Xiaoxi Yang,Yulu Huang,Mingxing Zhao,Qige Zheng,Yanxia Qi

The density of two functionalized ionic liquids (FILs) 1-methoxyethyl-3-methylimidazolium bis[(trifluoromethyl)sulfonyl]imide ([MOEmim][NTf 2 ] and 1-methoxyethyl-2,3-dimethylimidazolium bis[(trifluoromethyl)sulfonyl]imide [MOEmmim][NTf 2 ]) have been measured with ether solvents proprylene glycol monomethyl ether (PEGMME), diethylene glycol dimethyl ether (DEGDME), tetraethylene glycol dimethyl ether (TEGDME) at diluted concentration range. The determined temperature range is from 293.15 to 328.15 K at atmospheric pressure. The measured densities are used for the calculation of apparent molar volumes, V ϕ /m 3 ·mol −1 , at the temperature range. The effects of the ether ( O ) and methyl ( CH 3 ) introduction on imidazolium cation are discussed for the density and apparent molar volume in deeply. The Redlich-Rosenfeld-Meyer (RRM) equation was used for the fitting of apparent molar volumes, V ϕ /m 3 ·mol −1 , for the six studied dilute solutions. The infinite dilution apparent molar volumes, V ϕ /m 3 ·mol −1 , and limiting apparent molar expansibility, E Φ 0 / c m 3 · m o l - 1 · K - 1 EΦ0/cm3·mol-1·K-1 , have been obtained and discussed from the RRM equation and polynomial equation. The thermal expansion coefficients, α/K −1 , have also been calculated and discussed from density for the studied dilute solutions in the temperature range.

研究领域: 物理化学 · 材料科学
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JOURNAL OF PHYSICAL CHEMISTRY B · 2015 · IF 3.302

Formation of Ether-Functionalized Ionic-Liquid-Based Aqueous Two-Phase Systems and Their Application in Separation of Protein and Saccharides

Zhijun Wang,Yuanchao Pei,Jing Zhao,Zhiyong Li,Yujuan Chen,Kelei Zhuo

Ionic-liquid (IL)-based aqueous two-phase systems (ATPSs) have attracted much attention in the separation technology. In this work, we synthesized five novel ether-functionalized ILs and studied their applications in ATPS formation. The phase diagrams for several systems were determined at 298.15 K. An as-prepared IL (1-(2-butoxy-ethyl)-3-methylimidazolium chloride) was chosen as a representative to construct ATPSs for separation of bovine serum albumin (BSA) from aqueous saccharide solutions. Results showed that 76.1–94.3% of BSA was enriched into the IL-rich top phase and almost all the saccharides were extracted into the salt-rich bottom phase in a one-step separation process. The main factors affecting the separation process, such as kinds of saccharides and the amount of inorganic salts, were discussed. Furthermore, the size distributions of aggregates in the IL-rich top phase were determined by dynamic light scattering (DLS), and accordingly the possible mechanism for the separation was investigated.

研究领域: 生物化学 · 分离技术
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JOURNAL OF MOLECULAR LIQUIDS · 2023 · IF 6

Novel class of crown ether functionalized ionic liquids with multiple binding sites for efficient separation of lithium isotopes

Li Cui,Yuheng Fan,Jin Kang,Caixia Yin,Weilu Ding,Hongyan He,Fangqin Cheng

Lithium isotopes ( 6 Li, 7 Li) separation is an industrially important but challenging process due to their very similar chemical and physical properties. Crown ethers (CEs) have great potential in the isotopes separation for their typical cavity structures. However, the low distribution of Li + has restricted their industrial   use. In this work, a novel class of functionalized ionic liquids with grafted crown ether-moieties (CE-FILs) for efficient separation of 6 Li and 7 Li are first reported. The enhanced distribution of Li + could be achieved by the synergistic effect of ion–dipole interaction, hydrogen bonding and coordination interaction. As a result, an exceptionally high distribution coefficient for Li + ( D Li , up to 136) is obtained using 0.3 M [C 6 (B15C5)mim][NTf 2 ] with a satisfied separation factor of 1.034 (at 273 K) for 6 Li/ 7 Li selectivity from an extremely hydrophilic chloride solutions, which strikes an excellent balance between Li distribution and 6 Li/ 7 Li separation. Theoretical calculations and spectroscopic characterization confirm that [C 6 (B15C5)mim][NTf 2 ] supplies as an ion pair receptor to bind Li + , forming a 1:1 ion-pair complex [C 6 (B15C5)mim][NTf 2 ]…Li + FeCl 4 - with double cations and anions. The separation performance of 6 Li/ 7 Li mainly depends on the weak interactions associated with Li + . The CE-FILs pave a new way for Li isotopes separation.

研究领域: 化学 · 材料科学
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JOURNAL OF CHROMATOGRAPHY A · 2011 · IF 4.194

Preparation and characterization of novel crown ether functionalized ionic liquid-based solid-phase microextraction coatings by sol–gel technology

Xin Zhou,Peng-fei Xie,Jiang Wang,Bei-bei Zhang,Ming-ming Liu,Han-lan Liu,Xiong-han Feng

A novel crown ether functionalized ionic liquid (IL), 1-allyl-3-(6′-oxo-benzo-15-crown-5 hexyl) imidazolium hexafluorophosphate was synthesized and used as selective stationary phase to prepare task-specific IL-based solid phase microextraction (SPME) fibers by sol–gel method and free radical cross-linking technology. The underlying mechanism of the sol–gel reaction was proposed and the successful chemical bonding of the crown ether functionalized IL to the formed hybrid organic–inorganic copolymer coating was confirmed by FT-IR spectroscopy. The performance of this in situ created crown ether functionalized IL-based SPME fibers, was investigated in detail. The coating has porous surface structure, stable performance in high temperature (to 340   °C) and in different solutions (water, organic solvent, acid and alkali), and good coating preparation reproducibility. In contrast to the sol–gel derived 1-allyl-3-methyl imidazolium hexafluorophosphate-based coating prepared in our previous work with the identical procedure, the extraction performance of this newly developed sol–gel crown ether functionalized IL-based coating was superior for alcohols, phthalate esters , phenolic environmental estrogens, fatty acids and aromatic amines due to the introduction of benzo-15-crown-5 functional group in IL structure. Moreover, it was shown to provide higher or comparable extraction efficiencies for most analytes studied than did the commercial PDMS , PDMS/DVB and PA fibers.

研究领域: 分析化学 · 材料科学
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ANALYTICA CHIMICA ACTA · 2013 · IF 4.387

Two highly stable and selective solid phase microextraction fibers coated with crown ether functionalized ionic liquids by different sol–gel reaction approaches

Jianjun Shu,Pengfei Xie,Danni Lin,Rongfeng Chen,Jiang Wang,Beibei Zhang,Mingming Liu,Hanlan Liu,Fan Liu

In this work, two novel crown ether functionalized ionic liquid (FIL)-based solid phase microextraction (SPME) fibers were prepared by sol–gel technology using the synthesized 1-(trimethoxysily)propyl 3-(6′-oxo-benzo-15-crown-5 hexyl) imidazolium bis(trifluoromethanesulphonyl)imide ([TMSP(Benzo15C5)HIM][N(SO 2 CF 3 ) 2 ]) and 1-allyl-3-(6′-oxo-benzo-15-crown-5 hexyl) imidazolium bis(trifluoromethanesulphonyl)imide ([A(Benzo15C5)HIM][N(SO 2 CF 3 ) 2 ]) as selective stationary phases. Owing to the introduction of trimethoxysilypropyl to the imidazole cation, the [TMSP(Benzo15C5)HIM][N(SO 2 CF 3 ) 2 ] could be chemically bonded to the formed sol–gel silica substrate through the hydrolysis and polycondensation reaction. Similarly, the [A(Benzo15C5)HIM][N(SO 2 CF 3 ) 2 ] was able to participate in the formation of the organic–inorganic copolymer coatings through the free radical crosslinking reaction. These two fibers were determined to have “bubble-like” surface characteristics analogous to a previously prepared [A(Benzo15C5)HIM][PF 6 ]-based fiber. Their thermal stabilities were much higher than that of the [A(Benzo15C5)HIM][PF 6 ]-based coating. They were capable of withstanding temperatures as high as 400   °C without evident loss of the crown ether FILs. They also had strong solvent, acid and alkali resistance, good coating preparation reproducibility and high selectivity for medium polar to polar compounds. The high selectivity of these two fibers could be attributed to the strong ion-dipole, hydrogen bonding and π–π interactions provided by the synergetic effect of ILs and benzo-15-crown-5 functionalities. Moreover, the selectivity of these two fibers was rather different although the structures of these two crown ether FILs were very similar. This is maybe because the relative contents of the crown ether FILs chemically bonded to the organic–inorganic copolymer coatings were quite different when prepared by different sol–gel reaction approaches.

研究领域: 分析化学 · 材料科学
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