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MOLECULES · 2019 ·Vol. 24 ·期 3 ·442 · IF 3.06

Comparison of the Partition Efficiencies of Multiple Phenolic Compounds Contained in Propolis in Different Modes of Acetonitrile–Water-Based Homogenous Liquid–Liquid Extraction

Wenbin Chen,Xijuan Tu,Dehui Wu,Zhaosheng Gao,Siyuan Wu,Shaokang Huang

Homogeneous liquid–liquid extraction (HLLE) has attracted considerable interest in the sample preparation of multi-analyte analysis. In this study, HLLEs of multiple phenolic compounds in propolis, a polyphenol-enriched resinous substance collected by honeybees, were performed for improving the understanding of the differences in partition efficiencies in four acetonitrile–water-based HLLE methods, including salting-out assisted liquid–liquid extraction (SALLE), sugaring-out assisted liquid–liquid extraction (SULLE), hydrophobic-solvent assisted liquid–liquid extraction (HSLLE), and subzero-temperature assisted liquid–liquid extraction (STLLE). Phenolic compounds were separated in reversed-phase HPLC, and the partition efficiencies in different experimental conditions were evaluated. Results showed that less-polar phenolic compounds (kaempferol and caffeic acid phenethyl ester) were highly efficiently partitioned into the upper acetonitrile (ACN) phase in all four HLLE methods. For more-polar phenolic compounds (caffeic acid,p-coumaric acid, isoferulic acid, dimethoxycinnamic acid, and cinnamic acid), increasing the concentration of ACN in the ACN–H2O mixture could dramatically improve the partition efficiency. Moreover, results indicated that NaCl-based SALLE, HSLLE, and STLLE with ACN concentrations of 50:50 (ACN:H2O,v/v) could be used for the selective extraction of low-polarity phenolic compounds. MgSO4-based SALLE in the 50:50 ACN–H2O mixture (ACN:H2O,v/v) and the NaCl-based SALLE, SULLE, and STLLE with ACN concentrations of 70:30 (ACN:H2O,v/v) could be used as general extraction methods for multiple phenolic compounds.Keywords:salting-out assisted liquid–liquid extraction;sugaring-out assisted liquid–liquid extraction;hydrophobic-solvent assisted liquid–liquid extraction;subzero-temperature assisted liquid–liquid extraction;phenolic compounds

研究领域: 分析化学 · 植物化学
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Chemical Engineering Journal Advances · 2025 · IF 7.1

Molecular Dynamics Simulation of Boric Acid Extraction by Isobutanol/Isooctanol Liquid-Liquid Extraction

Jisheng Li,Xu Zhao,Yuheng Fan,Changyu Sun,Yufeng Hu,Laiyong Zhang,Fayan Zhu,Jilong Han

Boric acid, a vital chemical in industries, agriculture, and high-tech fields, is primarily extracted from Salt Lake brines via liquid-liquid extraction. The efficiency differences between alcohols remain unclear. This study investigates boric acid extraction using isobutanol and isooctanol, combining experiments and theoretical calculations to reveal microscopic mechanisms. Experiments show that under low pH, multi-stage extraction significantly impacts efficiency, with isooctanol outperforming isobutanol. Computational results reveal that isooctanol’s hydroxyl oxygen has a more negative electrostatic potential, forming stronger, more stable hydrogen bonds with boric acid. Isooctanol also exhibits shorter interaction distances and higher interaction energy with boric acid compared to isobutanol. The study concludes that isooctanol’s superior performance is due to its ability to form more and longer-lived hydrogen bonds. This work provides new theoretical insights into boric acid extraction and aids in designing efficient extractants.

CAS / MDL: 108-88-3 78-83-1
研究领域: 化学工程 · 理论计算
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JOURNAL OF CHEMICAL THERMODYNAMICS · 2015 · IF 2.679

(Liquid + liquid) extraction of methanol from alkanes using dialkylphosphate-based ionic liquids as solvents

Fufeng Cai,Guomin Xiao

In this work, the feasibility of ionic liquids (ILs), 1,3-dimethylimidazolium dimethylphosphate ([MMIM][DMP]), 1-ethyl-3-methylimidazolium diethylphosphate ([EMIM][DEP]), and 1-butyl-3-methylimidazolium dibutylphosphate ([BMIM][DBP]), as solvents for the extraction of methanol from its mixtures with hexane and heptane was analyzed. The knowledge of (liquid   +   liquid) equilibria (LLE) of these mixtures is necessary for the design of the extraction separation process. Hence, the LLE data for the ternary systems, {methanol   +   hexane   +   ([MMIM][DMP], or [EMIM][DEP], or [BMIM][DBP])}, and {methanol   +   heptane   +   ([MMIM][DMP], or [EMIM][DEP], or [BMIM][DBP])}, were measured at T   =   298.2   K and atmospheric pressure. The experimental results were correlated with the thermodynamic nonrandom two-liquid (NRTL) model. The solute distribution ratios of methanol and methanol/alkane selectivities, derived from the experimental LLE data, were calculated and analyzed to evaluate the capability of the studied ILs to accomplish the separation target. Meanwhile, these capabilities were also compared with that of other ILs obtained from the literature.

CAS / MDL: 142-82-5 71-23-8
研究领域: 化学工程 · 材料科学
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Journal of Materials Chemistry C · 2019 ·Vol. 8 ·期 3 ·989-995 · IF 6.641

Liquid–liquid extraction: a universal method to synthesize liquid colloidal photonic crystals

Chuan Wang,Xin Zhang,Huimin Zhu,Qianqian Fu,Jianping Ge

The liquid colloidal photonic crystal (PC) is a new kind of photonic structure with attractive properties, such as fluidity, structural metastability, and reversibility in colloidal assembly. However, its controllable synthesis is a big challenge, because it is very difficult to keep all the particles well-dispersed in a highly concentrated colloidal system, and then assemble them into colloidal crystals. In this work, a liquid–liquid extraction (LLE) method has been developed to produce liquid PCs via simple mixing and liquid phase separation at room temperature. Single- and two-component extractants are used to extract part of the solvent from a diluted colloidal solution, which effectively concentrates the colloidal solution without inducing any aggregation and produce highly crystalline liquid PCs by spontaneous precipitation. Compared to the conventional methods, this new LLE process provides a quick, convenient, scalable and universal synthesis of liquid PCs composed of different colloidal particles and solvents, which lays a solid basis for its application in structural-color displays, sensors, and coatings.

研究领域: 材料科学 · 光学
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SEPARATION SCIENCE AND TECHNOLOGY · 2018 · IF 1.2

Separation of Pt(IV), Pd(II), Ru(III), and Rh(III) from chloride medium using liquid–liquid extraction with mixed imidazolium-based ionic liquids

Yan Yan,Qi Wang,Zeyang Xiang,Yanzhao Yang

A reasonable project was presented for the extraction and separation of Pt(IV), Pd(II), Ru(III), and Rh(III) from the mixed imidazolium-based ionic liquids (ILs) [C6mim]Cl, [C6mim][NTf2], and [C6mim][DDTC]. Pt(IV) was first separated from other three platinum group metals with a mixture of [C6mim]Cl and [C6mim][NTf2]. Then, separation of Pd(II) and Ru(III) from Rh(III) was realized by changing the concentration of [C6mim][DDTC]. Back-extraction of Pt(IV), Pd(II), and Ru(III) from loaded hydrophobic phase and the recovery of Rh(III) in aqueous phase were also investigated. Mechanisms between Pd(II)/Ru(III) and [C6mim][DDTC] were further explored using ultraviolet spectrophotometry (UV-Vis), infrared spectrophotometry (FTIR), the method of continuous variations, ab initio quantum chemical studies, and X-ray crystallographic analysis. The results afford more directions for extracting and separating metals by introducing devisable functionalized group into ILs.

研究领域: 化学工程 · 分析化学
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PLoS One · 2017 ·Vol. 12 ·期 9 ·e0185302 · IF 2.806

Simultaneous determination of trace rare-earth elements in simulated water samples using ICP-OES with TODGA extraction/back-extraction

FuKai Li,AiJun Gong,LiNa Qiu,WeiWei Zhang,JingRui Li,Yu Liu,YuNing Liu,HuiTing Yuan

The determination of trace rare-earth elements (REEs) can be used for the assessment of environmental pollution, and is of great significance to the study of toxicity and toxicology in animals and plants. N, N, N′, N′-tetraoctyl diglycolamide (TODGA) is an environmental friendly extractant that is highly selective to REEs. In this study, an analytical method was developed for the simultaneous determination of 16 trace REEs in simulated water samples by inductively coupled plasma optical emission spectroscopy (ICP-OES). With this method, TODGA was used as the extractant to perform the liquid-liquid extraction (LLE) sample pretreatment procedure. All 16 REEs were extracted from a 3 M nitric acid medium into an organic phase by a 0.025 M TODGA petroleum ether solution. A 0.03 M ethylenediaminetetraacetic acid disodium salt (EDTA) solution was used for back-extraction to strip the REEs from the organic phase into the aqueous phase. The aqueous phase was concentrated using a vacuum rotary evaporator and the concentration of the 16 REEs was detected by ICP-OES. Under the optimum experimental conditions, the limits of detection (3σ, n = 7) for the REEs ranged from 0.0405 ng mL -1 (Nd) to 0.5038 ng mL -1 (Ho). The relative standard deviations (c = 100 ng mL -1 , n = 7) were from 0.5% (Eu) to 4.0% (Tm) with a linear range of 4–1000 ng mL -1 (R 2 > 0.999). The recoveries of 16 REEs ranged from 95% to 106%. The LLE-ICP-OES method established in this study has the advantages of simple operation, low detection limits, fast analysis speed and the ability to simultaneously determine 16 REEs, thereby acting as a viable alternative for the simultaneous detection of trace amounts of REEs in water samples.

研究领域: 分析化学 · 环境科学
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JOURNAL OF RADIOANALYTICAL AND NUCLEAR CHEMISTRY · 2020 ·Vol. 325 ·期 2 ·673-682 · IF 1.137

Lithium isotope effect in extraction of lithium chloride by 4-Aminobenzo-15-crown-5 in water-anisole ionic liquid double solvent system

Liu Bing,Jia Yongzhong,Jing Yan,Zhang Quanyou,Shao Fei,Yao Ying

Abstract The lithium isotope separation (LIS) plays a vital role in development of nuclear industry. The liquid–liquid extraction technologies open up new possibilities for LIS. This work presents preliminary results of the study on the extractions and separation of 6 Li/ 7 Li by mixed system, comprising amino-derivatives of benzo-15-crown-5 (4AB), ionic liquid and anisole. 4AB was used as an extractant. The eparation factor ( α ) is 1.031 ± 0.001, and abundance of 6 Li in loaded organic phase is 7.76%. Meanwhile, the reason why 4AB has better separation efficiency than B15C5 was explored brief by Fourier transform infrared (FT-IR) spectrum and quantum chemical calculations. Graphic abstract

研究领域: 核工业 · 化学工程
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INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH · 2019 · IF 3.375

Efficient Liquid–Liquid Extraction of Benzene from Its Mixture with Cyclohexane by Utilizing Hyperbranched Polymeric Ammoniums Salts

Zhiwei Wang,Xuan Yuan,Guoxing Yang,Weidong Zhang,Lijia Liu,Hongxing Dong,Chunhong Zhang,Jianwei Bai,Linghui Meng

A novel hyperbranched polymeric quaternary ammonium salt (HPQAS) with benzene rings in the structure (PVBC-TMA) was synthesized by self-condensing vinyl polymerization followed with quaternary amination reaction. Meanwhile, a hyperbranched polyamidoamine (PAMAM) was separately neutralized with different acids to produce the HPQASs without benzene rings. These HPQASs were dissolved in DMSO and used to extract benzene from its mixture with cyclohexane. The liquid–liquid equilibrium (LLE) data indicate that the HPQAS/DMSO mixture showed a higher selectivity coefficient (19.92) than DMSO (<15). PVBC-TMA having benzene rings showed higher extraction performance than the PAMAM salts without benzene rings, especially when the composition of benzene/cyclohexane is close to the azeotrope state. The cation−π and π–π interactions between the ammonium ion and the benzene ring in the HPQAS with benzene in the benzene/cyclohexane mixture were thought to be the mass transfer impetus for extracting benzene from its mixture with cyclohexane by utilizing the HPQASs. This was the first example of applying the hyperbranched polymeric ammonium in the separation of benzene/cyclohexane.

研究领域: 化学工程 · 材料科学
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JOURNAL OF CHEMICAL AND ENGINEERING DATA · 2017 · IF 2.323

Modeling Multiple Chemical Equilibrium in Single-Stage Extraction of Atenolol Enantiomers with Tartrate and Boric Acid as Chiral Selector

Panliang Zhang,Shichuan Wang,Weifeng Xu,Kewen Tang

Enantioselective liquid–liquid extraction (ELLE) was adopted to separate atenolol (AT) enantiomers, where tartrate and boric acid (BA) were used as the chiral selector. Influence of process variables on extraction efficiency were studied, including type of tartaric acid derivatives, type of the organic solvent, pH of aqueous phase, molality of BA and tartaric acid derivatives, as well as temperature. A theoretical model was developed based on the mechanism research on reactive extraction of AT enantiomers by n-hexyl (L)-tartrate (LT) and BA. Important parameters of this model were determined. By modeling and experiment, the optimal conditions identified involve the LT molality of 0.0796 mol·kg–1, BA molality of 0.1 mol·kg–1, AT molality of 1.592 mmol·kg–1, and pH value of 9.00 at 278 K, where the obtained enantioselectivity (α) is 1.8951 and performance factor (pf) is 0.0608.

CAS / MDL: 147-71-7 87-69-4
研究领域: 化学工程 · 药物化学 · 分析化学
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JOURNAL OF MOLECULAR LIQUIDS · 2021 · IF 6.165

Lithium isotope separation effect of N-phenylaza-15-crown-5

Qian Zhang,Yongzhong Jia,Jinhe Sun,Pengrui Zhang,Chaochi Huang,Mingyong Wang,Zixuan Xue,Ciming Wang,Fei Shao,Fengtai Tong,Yilin Xiao,Yan Jing

Azacrown ethers contain multiple coordination sites, which show specific complexation to alkali metal ions . In this research, a neoteric liquid-liquid extraction system was investigated for the selective separation of lithium isotope using N -phenylaza-15-crown-5 (Ph-N15C5) as chelating agent and [BMIm][NTf 2 ] and anisole as extraction solvent. The effects of the counter anions of lithium salt , concentrations of crown ether , temperature, extraction equilibrium time and concentrations of lithium salt solution on the separation of lithium isotope with Ph-N15C5 were studied. The maximum extraction efficiency of lithium ions was 41.54% and the maximum single-stage separation factor (α) of 6 Li/ 7 Li obtained in the present study was 1.025, indicating that the lighter isotope 6 Li was enriched in organic phase while the heavier isotope 7 Li was concentrated in the aqueous phase. The complexation ratio of the lithium crown ether complex was determined as 1:1 by the slope analysis method. The lithium ions in the aqueous phase were extracted into the organic phase to form [Li(Ph-N15C5)] + complex. The thermodynamic data obtained at different temperatures demonstrated that lithium isotope exchange was a spontaneous exothermic process , and lowering the temperature was beneficial to increase the separation factor. In addition, the system reached the extraction equilibrium after 60 min. This high efficiency and green liquid-liquid extraction system has potential application in lithium isotope separation.

研究领域: 化学 · 材料科学
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JOURNAL OF MOLECULAR LIQUIDS · 2024 · IF 5.3

A mixed solvent system of amino crown ether and ionic liquids for a high-efficient extraction of cesium

Jintao He,Junyuan Hua,Xiaohua Ma,Ranil Wickramasinghe,Jianxin Li

Efficient extraction of Cs + from aqueous solution was investigated by liquid–liquid extraction based on ionic liquids (ILs). In this study, Di(aminobenzo)-18-crown-6 (DAB18C6) was used as the extractant and three ILs (1-butyl-3-methylimidazolium hexafluorophosphate ([C 4 mim][PF 6 ]), 1-hexyl-3-methylimidazolium hexafluorophosphate ([C 6 mim][PF 6 ]), and 1-butyl-3-methylimidazolium bis-trifluoromethyl sulfonamide ([C 4 mim][NTf 2 ])) were employed as co-extractants in the construction of a liquid–liquid extraction system for efficient and selective extraction of Cs + from aqueous solutions. It was demonstrated that the DAB18C6-[C 4 mim][NTf 2 ] mixed solvent system at 0.12 mol/L DAB18C6, a mass ratio of ILs/CHCl 3 of 1:4 and a volumetric ratio of O/A of 1:1 exhibited a high % extraction of Cs + up to 99.94 %, with a higher selectivity for Cs + relative to coexisting ions such as K + ( β Cs/K  = 1216.7) and Rb + ( β Cs/Rb  = 139.03). The high selectivity of the extraction system for Cs + was attributed to the lower hydration binding energy of Cs + (−366.51 kJ/mol) and the stronger interaction between DAB18C6 and Cs + , g(r) = 12.7. Further, the hydrogen bonding interaction between the amino crown ether and ionic liquid increases the viscosity and surface tension of the extraction system, thus enhancing the stability of the system. Noteworthy, the most stable structure formed by DAB18C6-Cs + -[NTF 2 ] − is attributed to cation exchange. In summary, this study demonstrates the great potential for efficient separation and extraction of cesium from aqueous solutions.

研究领域: 化学工程 · 环境科学
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PROCESS BIOCHEMISTRY · 2018 · IF 2.616

A new method for comprehensive utilization of wood vinegar by distillation and liquid−liquid extraction

Zhanchao Li,Lening Zhang,Guanyu Chen,Lijie Wu,Boyang Liu,Yue Li,Shuang Sun,Hanqi Zhang,Zhiquan Zhang,Ziming Wang

To increase the added value and commercialization of wood vinegar (WV), a new method for comprehensive utilization of WV was developed. The primary distillation, liquid–liquid extraction and secondary distillation were used to isolate the different active fractions from WV in the new route. The antioxidant activities of all the fractions were expressed as vitamin C equivalent antioxidant capacities in mg/L using 1, 1-diphenyl-2-picrylhydrazyl scavenging assay, and the antimicrobial activities against Escherichia coli ( E. coli ) in vitro were represented by the absorbance at a wavelength of 600 nm. The results demonstrated that the isolation of the antioxidants (phenolic compounds) from the residue obtained from primary distillation was satisfactory when the EtOAc/ n -hexane (7/3, v/v) was used as extraction solvent and pH value was 4. Acetic acid has inhibition effect on the antioxidant activities of phenolic compounds. The fraction enriched with acetic acid exhibited high antimicrobial activity. Considering the low environmental risk of WV, the findings suggest that WV is potentially useful for the developments of antioxidant and antimicrobial agents in the field of medicine or food preservation and safety.

CAS / MDL: 765-70-8
研究领域: 生物化学 · 食品科学 · 医药学
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