疏水性低共熔溶剂氢键交互作用调控及萃取铜性能

doi:10.16085/j.issn.1000-6613.2022-0563

化工进展 ›› 2022, Vol. 41 ›› Issue (S1): 397-406.DOI: 10.16085/j.issn.1000-6613.2022-0563

疏水性低共熔溶剂氢键交互作用调控及萃取铜性能

叶玉玺¹(), 丁晓茜¹, 池华睿¹, 朱楷伦¹, 刘杨², 王凌云¹(), 郭庆杰¹^,³

^1.青岛科技大学化工学院，山东青岛 266042
^2.青岛科技大学环境学院，山东青岛 266042
^3.宁夏大学省部共建煤炭高效利用与绿色化工国家重点实验室，宁夏银川 750021

收稿日期:2022-04-04 修回日期:2022-04-28 出版日期:2022-10-20 发布日期:2022-11-10
通讯作者: 王凌云
作者简介:叶玉玺（1997—），男，硕士研究生，研究方向为传质与分离工程。E-mail：yyx3570634@163.com。
基金资助:
山东省生态化工协同创新中心开放课题(STHGYX2216);省部共建煤炭高效利用与绿色化工国家重点实验室开放课题(2022-K24)

Hydrophobic deep eutectic solvent hydrogen bond interaction regulation and extraction performance of copper

YE Yuxi¹(), DING Xiaoxi¹, CHI Huarui¹, ZHU Kailun¹, LIU Yang², WANG Lingyun¹(), GUO Qingjie¹^,³

^1.College of Chemical Engineering, Qingdao University of Science and Technology, Qingdao 266042, Shandong, China
^2.College of Environmental, Qingdao University of Science and Technology, Qingdao 266042, Shandong, China
^3.State Key Laboratory of High-efficiency Utilization of Coal and Green Chemical Engineering, Ningxia University, Yinchuan 750021, Ningxia, China

Received:2022-04-04 Revised:2022-04-28 Online:2022-10-20 Published:2022-11-10
Contact: WANG Lingyun

摘要/Abstract

摘要：

制备了以薄荷醇为氢键受体，不同碳链长度的羧酸为氢键供体的薄荷醇-羧酸类疏水性低共熔溶剂。探索了低共熔溶剂体系的密度、黏度理化特性随温度变化的规律，利用超额摩尔性质与格伦伯格-尼桑相互作用力公式计算了过量摩尔体积、黏度偏差与相互作用力参数，分析了低共熔溶剂组分间的相互作用。通过傅里叶红外光谱表征，确定了低共熔溶剂组分间的氢键作用。以该类低共熔溶剂作萃取剂，考察了pH、组分间氢键交互作用力（氢键供体碳链长度、低共熔溶剂受供体摩尔比）对提取铜性能的影响。结果表明，薄荷醇-羧酸类疏水性低共熔溶剂中氢键交互作用更强的体系，由于羧基中氢的解离更容易实现，对铜的萃取效率更高。此外，通过对薄荷醇-羧酸类疏水性低共熔溶剂体系结构性质与组分间氢键作用的关系对铜的萃取机理进行了探讨，为揭示疏水性低共熔溶剂的构效关系与高性能低共熔溶剂的设计优化提供理论基础。

关键词: 疏水性低共熔溶剂, 溶剂萃取, 环境, 分离, 物化性质, 氢键作用

Abstract:

A series of hydrophobic deep eutectic solvents (HDES) were synthesized with menthol as hydrogen bond acceptor and different kinds of carboxylic acids as hydrogen bond donor. The physicochemical properties of HDES system such as density and viscosity under different temperatures were investigated. The excess molar volume, viscosity deviation and interaction force parameters were calculated by using the excess molar property and the Glenberg-Nissan interaction force formula, and the interaction between components of HDES was analyzed. The hydrogen bonding between HDES components was determined by FTIR characterization. Solvent extraction of Cu²⁺ from aqueous phase was studied by the prepared HDES. The effects of pH, intercomponent interactions (carbon chain length of hydrogen bond donor, donor/acceptor molar ratio) on the extraction performance of copper were investigated. The results showed that the extraction efficiency of Cu²⁺ could be enhanced by the system with stronger hydrogen bond interaction among Men/Carboxylics-HDES, due to easier dissociation of hydrogen in carboxylic group. In addition, the extraction mechanism for copper was discussed through the relationship between the structure and properties of Men/Carboxylics-HDES system and the hydrogen bond interaction between components. The present work may provide a theoretical basis for revealing the structure-activity relationship of HDES and for further design of high-performance eutectic solvent.

Key words: hydrophobic deep eutectic solvents, solvent extraction, environment, separation, physicochemical property, hydrogen bond interaction

中图分类号:

TQ413

叶玉玺, 丁晓茜, 池华睿, 朱楷伦, 刘杨, 王凌云, 郭庆杰. 疏水性低共熔溶剂氢键交互作用调控及萃取铜性能[J]. 化工进展, 2022, 41(S1): 397-406.

YE Yuxi, DING Xiaoxi, CHI Huarui, ZHU Kailun, LIU Yang, WANG Lingyun, GUO Qingjie. Hydrophobic deep eutectic solvent hydrogen bond interaction regulation and extraction performance of copper[J]. Chemical Industry and Engineering Progress, 2022, 41(S1): 397-406.

图/表 13

参考文献 26

1	易兰, 李文英, 冯杰. 离子液体/低共熔溶剂在煤基液体分离中的应用[J]. 化工进展, 2020, 345(6): 2066-2078.
	Yi Lan, Li Wenying, Feng Jie. Application of ionic liquids and deep eutectic solvents in the separation of coal-based liquids[J]. Chemical Industry and Engineering Progress, 2020, 345(6):2066-2078.
2	TERESHATOV E E, BOLTOEVA M Y, FOLDEN C M. First Evidence of metal transfer into hydrophobic deep eutectic and low-transition-temperature mixtures: indium extraction from hydrochloric and oxalic acids[J]. Green Chemistry, 2016, 18: 4616-4622.
3	ABBOTT Andrew P, BOOTHBY David, CAPPER Glen, et al. Deep eutectic solvents formed between choline chloride and carboxylic acids: versatile alternatives to ionic liquids[J]. Journal of the American Chemical Society, 2004, 126: 9142-9147.
4	成洪业, 漆志文. 低共熔溶剂用于萃取分离的研究进展[J]. 化工进展, 2020, 39(12): 4896-4907.
	CHENG Hongye, QI Zhiwen. Research progress of deep eutectic solvent for extractive separation[J]. Chemical Industry and Engineering Progress, 2020, 39(12): 4896-4907.
5	VAN OSCH Dannie J G P, PARMENTIER Dries, DIETZ Carin H J T, et. al . Removal of alkali and transition metal ions from water with hydrophobic deep eutectic solvents[J]. Chemical Communications, 2016, 52: 11987.
6	Ebru KURTULBAŞ, PEKEL Ayse Gizem, İrem TOPRAKÇi, et. al . Hydrophobic carboxylic acid based deep eutectic solvent for the removal of diclofenac[J]. Biomass Conversion and Biorefinery, 2020. DOI:10.1007/s13399-020-00721-1 .
7	RIVERIRO Elisa, GONZALEZ Begona, DOMINGUEZ Angeles. Extraction of adipic, levulinic and succinic acids from water using TOPO-based deep eutectic solvents[J]. Separation and Purification Technology, 2020, 241: 116692.
8	CAO Jun, YANG Meng, CAO Fuliang, et. al . Well-designed hydrophobic deep eutectic solvents as green and efficient media for the extraction of artemisinin from artemisia annua leaves[J]. ACS Sustainable Chemistry & Engineering, 2017, 5: 3270-3278.
9	GILMORE Mark, MCCOURT Eadaoin N, CONNOLLY Francis, et al. Hydrophobic deep eutectic solvents incorporating trioctylphosphine oxide: advanced liquid extractants[J]. ACS Sustainable Chemistry & Engineering, 2018, 6: 17323-17332.
10	PHELPS Tim, BHAWAWET Nakara, BAKER Gary, et al. Efficient and selective extraction of ⁹⁹mTcO₄ ^- from aqueous media using hydrophobic deep eutectic solvents[J]. ACS Sustainable Chemistry & Engineering, 2018, 6: 13656-13661.
11	SCHAEFFER Nicolas, CONCEIÇÃO Joao H F, MARTINS Monia A R, et al. Non-ionic hydrophobic eutectics-versatile solvents for tailored metal separation and valorisation[J]. Green Chemistry, 2020, 22(9): 2810-2820.
12	SMITH EmmA L, ABBOTT Andrew P, RYDER Karl S. Deep eutectic solvents (DESs) and their applications[J]. American Chemical Society, 2014, 114: 11060-11082.
13	VAN OSCH Dannie J G P, DIETZ Carin H J T, WARRAG Samah E E, et al. The curious case of hydrophobic deep eutectic solvents: a story on the discovery, design and applications[J]. ACS Sustainable Chemistry & Engineering, 2020, 8(29): 10591-10612.
14	VANDA Henni, DAI Yuntao, WILSON Erica G, et al. Green solvents from ionic liquids and deep eutectic solvents to natural deep eutectic solvents[J]. Comptes Rendus Chimie, 2018, 21(6): 628-638.
15	MARTINS Monia A R, CRESPO Emanuel A, PONTES Pontes V A, et al. Tunable hydrophobic eutectic solvents based on terpenes and monocarboxylic acids[J]. ACS Sustainable Chemistry & Engineering, 2018, 6(7): 8836-8846.
16	SCHAEFFER Nicolas, MARTINS Monia A R, NEVES Catarina M S S, et al. Sustainable hydrophobic terpene-based eutectic solvents for the extraction and separation of metals[J]. Chemical Communications, 2018, 54(58): 8104-8107.
17	BOUNSIAR Razika, Ignacio GASCÓN, AMIRECHE Fouzia, et. al . Volumetric properties of three pyridinium-based ionic liquids with a common cation or anion[J]. Fluid Phase Equilibria, 2020, 521: 112732.
18	LIU Baoyou, LIU Yaru. Properties for binary mixtures of (acetamide + KSCN) eutectic ionic liquid with ethanol at several temperatures[J]. The Journal of Chemical Thermodynamics, 2016, 92: 1–7.
19	HOSSEINI Sayed Mostafa, ALAVIANMEHR Mohammad Mehdi, MOGHADASI Jalill. Transport properties of pure and mixture of ionic liquids from new rough hard-sphere-based model[J]. Fluid Phase Equilibria, 2016, 429: 266-274.
20	MA Chunyan, LAAKSONEN Aatto, LIU Chang, et. al . The peculiar effect of water on ionic liquids and deep eutectic solvents[J]. Chemical Society Reviews, 2018, 47: 8685.
21	唐静, 金利华, 李淑妮, 等.溴代烷基咪唑类离子液体水溶液二元体系的物化性质研究[J].化学与生物工程, 2019, 36(8): 37-42, 48.
	TANG Jing, JIN Lihua, LI Shu’ni, et al. Physicochemical properties of alkyl imidazolium bromide ionic liquid aqueous solution binary system[J]. Chemistry & Bioengineering, 2019, 36(8): 37-42, 48.
22	NGUYEN Thi Thuy Nhi, NGUYEN Viet Nhan Hoa, LIU Yang, et al. Analysis of the interaction in the mixture of organophosphorus acids and Aliquat 336 through the measurement of dielectric constant and viscosity[J]. Journal of Molecular Liquids, 2020, 315.DOI:10.1016/j.molliq.2020.113738 .
23	LIU Yang, LEE Man Seung. Determination of viscosity and dielectric constant for studying the interactions in binary mixtures of organophosphorus acid andtertiary amine[J]. Journal of Molecular Liquids, 2016, 222: 233-238.
24	ZHU Siwen, LI Hongping, ZHU Wenshuai, et al. Vibrational analysis and formation mechanism of typical deep eutectic solvents: an experimental and theoretical study[J]. Journal of Molecular Graphics & Modelling, 2016, 68: 158.
25	ADJEL F, BARKAT D. Synergistic extraction of copper(Ⅱ) from sulfate medium with capric acid and tri-n-octylphosphine oxide in chloroform[J]. Journal of Coordination Chemistry, 2011, 64(4): 574-582.
26	IRANNAJAD Mehdi, HAGHIGHI Hossein Kamran, NASIRPOUR Zeinab. New solvent extraction process of nickel and copper by D2EHPA in the presence of carboxylates[J]. Transactions of the Indian Institute of Metals, 2020, 73(4): 1053-1063.

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疏水性低共熔溶剂氢键交互作用调控及萃取铜性能

Hydrophobic deep eutectic solvent hydrogen bond interaction regulation and extraction performance of copper

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