Physicochemical properties of choline chloride-based deep eutectic solvents and excess properties of their pseudo-binary mixtures with 1-butanol

被引:166
作者
Gajardo-Parra, Nicolas F. [1 ]
Lubben, Michael J. [2 ]
Winnert, Joshua M. [2 ]
Leiva, Angel [3 ]
Brennecke, Joan F. [2 ]
Canales, Roberto, I [1 ]
机构
[1] Pontificia Univ Catolica Chile, Dept Ingn Quim & Bioproc, Ave Vicuna Mackenna 4860, Santiago, Chile
[2] Univ Texas Austin, McKetta Dept Chem Engn, Austin, TX 78712 USA
[3] Pontificia Univ Catolica Chile, Fac Quim & Farm, Dept Quim Fis, Ave Vicuna Mackenna 4860, Santiago, Chile
关键词
Deep eutectic solvents; Excess enthalpy; Density; Viscosity; 1-Butanol; PLUS ETHYLENE-GLYCOL; IONIC LIQUIDS; VOLUMETRIC PROPERTIES; TEMPERATURE-RANGE; AQUEOUS MIXTURES; REFRACTIVE-INDEXES; SURFACE-TENSION; CARBON-DIOXIDE; LEVULINIC ACID; MOLAR ENTHALPY;
D O I
10.1016/j.jct.2019.02.010
中图分类号
O414.1 [热力学];
学科分类号
摘要
Ionic liquids and deep eutectic solvents have aroused interest as alternative solvents for separation processes due to their favourable properties. For instance, deep eutectic solvents are usually biodegradable, non-toxic, low cost and also share some properties with ionic liquids, such as their tuneability to be used in specific applications. Recently, deep eutectic solvents have been studied more extensively but their physicochemical characterization is still in the initial stages if the final objective is to select alternatives for industrial processes. Decomposition temperature, surface tension, density, and viscosity were measured for deep eutectic solvents based on choline chloride as the hydrogen bond acceptor and levulinic acid, ethylene glycol and phenol as hydrogen bond donors (in a 1:2 mol ratio). Density, viscosity and excess enthalpy were measured for pseudo-binary mixtures of the different deep eutectic solvents with 1-butanol. The excess properties were calculated to understand the behaviour of the deep eutectic solvents in the mixture. The results suggest that deep eutectic solvents are formed due to strong intermolecular forces between their constituents, with no reaction observed. This generates a higher thermal stability of the deep eutectic solvents compared to their constituent hydrogen bond donor. Also, with the addition of 1-butanol to the deep eutectic solvents, the mixture has a lower volume compared with the ideal case due to the creation of new networks of hydrogen bonds and interstitial site accommodations. Hence, the excess molar volumes and excess enthalpies have a negative deviation from the ideal behaviour. The viscosity deviation is related to the Arrhenius equation observing a negative deviation for the deep eutectic solvents containing levulinic acid and phenol, and a positive deviation for the one with ethylene glycol. Experimental data for the different properties allows a qualitative understanding of the magnitude of the interactions that occur when mixing deep eutectic solvents with 1-butanol. (C) 2019 Elsevier Ltd.
引用
收藏
页码:272 / 284
页数:13
相关论文
共 67 条
[1]   Thermodynamics of phase transfer for polar molecules from alkanes to deep eutectic solvents [J].
Abbott, Andrew P. ;
Al-Murshedi, Azhar Y. M. ;
Alshammari, Odeh A. O. ;
Harris, Robert C. ;
Kareem, Jalil H. ;
Qader, Idrees B. ;
Ryder, Karl S. .
FLUID PHASE EQUILIBRIA, 2017, 448 :99-104
[2]   Glycerol eutectics as sustainable solvent systems [J].
Abbott, Andrew P. ;
Harris, Robert C. ;
Ryder, Karl S. ;
D'Agostino, Carmine ;
Gladden, Lynn F. ;
Mantle, Mick D. .
GREEN CHEMISTRY, 2011, 13 (01) :82-90
[3]   Preparation of novel, moisture-stable, Lewis-acidic ionic liquids containing quaternary ammonium salts with functional side chains [J].
Abbott, AP ;
Capper, G ;
Davies, DL ;
Munro, HL ;
Rasheed, RK ;
Tambyrajah, V .
CHEMICAL COMMUNICATIONS, 2001, (19) :2010-2011
[4]   Deep eutectic solvents formed between choline chloride and carboxylic acids: Versatile alternatives to ionic liquids [J].
Abbott, AP ;
Boothby, D ;
Capper, G ;
Davies, DL ;
Rasheed, RK .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (29) :9142-9147
[5]  
Aissaoui T., 2015, Pharm Anal Acta, V6, P11, DOI DOI 10.4172/2153-2435.1000448
[6]   Surface tension of binary mixtures of ethanol plus ethylene glycol from 20 to 50 °C [J].
Azizian, S ;
Hemmati, M .
JOURNAL OF CHEMICAL AND ENGINEERING DATA, 2003, 48 (03) :662-663
[7]   Volumetric and Viscometric Study of Binary Systems of Ethyl Butyrate with Alcohols [J].
Bajic, Divna M. ;
Zivkovic, Emila M. ;
Serbanovic, Slobodan S. ;
Kijevcanin, Mirjana Lj. .
JOURNAL OF CHEMICAL AND ENGINEERING DATA, 2014, 59 (11) :3677-3690
[8]  
Buchner E. H., 1906, Z PHYS CHEM, P665
[9]   VISCOSITIES OF PURE POLYAROMATIC HYDROCARBONS [J].
BYERS, CH ;
WILLIAMS, DF .
JOURNAL OF CHEMICAL AND ENGINEERING DATA, 1987, 32 (03) :344-348
[10]   Green and Sustainable Solvents in Chemical Processes [J].
Clarke, Coby J. ;
Tu, Wei -Chien ;
Levers, Oliver ;
Brohl, Andreas ;
Hallett, Jason P. .
CHEMICAL REVIEWS, 2018, 118 (02) :747-800