Solubilities of caffeic acid and tyrosol in two protic ionic liquids and one deep eutectic solvent

被引：7
作者：
Prinos, Nikolaos [1 ]
Boli, Elenitsa [1 ]
Louli, Vasiliki [1 ]
Pappa, Georgia [1 ]
Magoulas, Kostis [1 ]
Voutsas, Epaminondas [1 ]
机构：
[1] Natl Tech Univ Athens, Sch Chem Engn, Lab Thermodynam & Transport Phenomena, 9 Heroon Polytech Str,Zografou Campus, Athens 15780, Greece
来源：
FLUID PHASE EQUILIBRIA | 2022年 / 559卷
关键词：
Tyrosol; Caffeic acid; Ionic liquids; Deep eutectic solvent; Solubility; CHOLINE CHLORIDE; ANTIOXIDANT ACTIVITY; BIOACTIVE COMPOUNDS; OLIVE OIL; PHYSICAL-PROPERTIES; PHENOLIC-COMPOUNDS; AQUEOUS MIXTURES; HIV-1; INTEGRASE; CARBON-DIOXIDE; EXTRACTION;
D O I：
10.1016/j.fluid.2022.113462
中图分类号：
O414.1 [热力学];
学科分类号：
摘要：
The present work provides solubility measurements for two phenolic compounds, caffeic acid and tyrosol, in two protic ionic liquids, 2-hydroxyethylammonium formate (2HEAF) and 2-hydroxyethylammonium acetate (2HEAA), and in the Deep Eutectic Solvent (DES) choline chloride-urea (ChCl:urea (1:2)). Solubility measurements of tyrosol were also performed in ethanol and water. All measurements were conducted under atmospheric pressure and in the temperature range of 293.15-313.15 K. Moreover, densities of pure 2HEAF, 2HEAA and ChCl:urea (1:2) and the viscosity of ChCl:urea (1:2), were measured. ChCl:urea (1:2) showed the highest solvation capacity among all the solvents studied for both compounds, while tyrosol was found to be more soluble than caffeic acid in all solvents. In order to better understand the solubilization process, the van't Hoff equation was applied for calculating the apparent Gibbs energy, enthalpy and entropy of solution. Finally, correlation of the solubility data was achieved with UNIQUAC and NRTL activity coefficient models. (C) 2022 Elsevier B.V. All rights reserved.
引用
收藏
页数：9
相关论文
共 70 条
[1]   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
[2]   STATISTICAL THERMODYNAMICS OF LIQUID-MIXTURES - NEW EXPRESSION FOR EXCESS GIBBS ENERGY OF PARTLY OR COMPLETELY MISCIBLE SYSTEMS [J].
ABRAMS, DS ;
PRAUSNITZ, JM .
AICHE JOURNAL, 1975, 21 (01) :116-128
[3]  
Albuquerque BR, 2021, FOOD FUNCT, V12, P14, DOI [10.1039/d0fo02324h, 10.1039/D0FO02324H]
[4]   Solubilities of p-coumaric and caffeic acid in ionic liquids and organic solvents [J].
Alevizou, Efthimia I. ;
Voutsas, Epaminondas C. .
JOURNAL OF CHEMICAL THERMODYNAMICS, 2013, 62 :69-78
[5]   Thermophysical properties of binary mixtures of {ionic liquid 2-hydroxy ethylammonium acetate plus (water, methanol, or ethanol)} [J].
Alvarez, Victor H. ;
Mattedi, Silvana ;
Martin-Pastor, Manuel ;
Aznar, Martin ;
Iglesias, Miguel .
JOURNAL OF CHEMICAL THERMODYNAMICS, 2011, 43 (07) :997-1010
[6]   Parallel developments in aprotic and protic ionic liquids: Physical chemistry and applications [J].
Angell, C. Austen ;
Byrne, Nolene ;
Belieres, Jean-Philippe .
ACCOUNTS OF CHEMICAL RESEARCH, 2007, 40 (11) :1228-1236
[7]   Antioxidant activity of phenolics extracted from Olea europaea L-leaves [J].
Benavente-García, O ;
Castillo, J ;
Lorente, J ;
Ortuño, A ;
Del Rio, JA .
FOOD CHEMISTRY, 2000, 68 (04) :457-462
[8]   Convenient synthesis of hydroxytyrosol and its lipophilic derivatives from tyrosol or homovanillyl alcohol [J].
Bernini, Roberta ;
Mincione, Enrico ;
Barontini, Maurizio ;
Crisante, Fernanda .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2008, 56 (19) :8897-8904
[9]   Viscosities of pure protic ionic liquids and their binary and ternary mixtures with water and ethanol [J].
Boli, Elenitsa ;
Katsavrias, Thanos ;
Voutsas, Epaminondas .
FLUID PHASE EQUILIBRIA, 2020, 520
[10]   Ionic liquids as entrainers for the separation of azeotropic mixtures: Experimental measurements and COSMO-RS predictions [J].
Boli, Elenitsa ;
Voutsas, Epaminondas .
CHEMICAL ENGINEERING SCIENCE, 2020, 219
1234567