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Solubility modeling, solvent effect and mixing properties of 5-chloro-8-hydroxyquinoline (Form I) in twelve pure solvents at various temperatures
Journal of Molecular Liquids ( IF 6 ) Pub Date : 2020-03-30 , DOI: 10.1016/j.molliq.2020.112988
Yameng Wan , Haixia He , Renren Sun , Liyuan Li , Jiao Sha , Gaoliang Jiang , Yu Li , Xinding Yao , Tao Li , Baozeng Ren

Mole-fraction solubility of 5-chloro-8-hydroxyquinoline (cloxiquine) Form I in twelve neat solvents namely “methyl acetate (MtAC), ethyl acetate (EtAC), n-propyl acetate (n-PrAC), isopropyl acetate (IPrAC), methanol (MtOH), ethanol (EtOH), n-propyl alcohol (n-PrOH), isopropyl alcohol (IPrOH), 2-methoxyethanol, 2-ethoxyethanol, 1,4-dioxane and acetone (DMK)” was determined under 0.1 MPa in this research work. The results show that cloxiquine solubility is directly proportional to temperature in selected solvents. The general solubility order at 298.15 K is: 1,4-dioxane (0.0751) > 2-ethoxyethanol (0.0333) > n-PrAC (0.0297) > 2-methoxyethanol (0.0291) > EtAC (0.0269) > MtAC (0.0245) > IPrAC (0.0232) > DMK (0.0200) > n-PrOH (0.0076) > EtOH (0.0058) > IPrOH (0.0045) > MtOH (0.0042). Solvent effects on cloxiquine solubility were studied by Kamlet, Abboud and Taft linear solvation energy relationships (KAT-LSER) model, and the results showed that the sensitivity of solvent-solvent interaction (52.16%) was much higher than that of solute-solvent interaction (26.22%). Moreover, five activity coefficient functions (Margules, NRTL, Wilson, NRTL-SAC and UNIQUAC model) were applied for the correlation with solubility data. The average ARD (average relative deviation) is lower than 2.01% and average RMSD (root mean square deviation) lower than 5.87E−4. Five selected models provide good consistencies with experimental solubility values. Furthermore, mixing thermodynamic properties were calculated by Wilson model, the results of which suggested that the mixing of cloxiquine with selected solvents was spontaneous and entropy-driven process.



中文翻译:

5-氯-8-羟基喹啉(I型)在十二种纯溶剂中在不同温度下的溶解度模型,溶剂效应和混合性能

5-氯-8-羟基喹啉(cloxiquine)的摩尔分数的溶解度形式I在12种整齐溶剂即“乙酸甲酯(MTAC),乙酸乙酯(ETAC),Ñ丙基乙酸酯(Ñ -PrAC),乙酸异丙酯(奕博) ,甲醇(MtOH),乙醇(EtOH),ñ丙基醇(ñ的i-PrOH),异丙醇(iPrOH中),2-甲氧基乙醇,2-乙氧基乙醇,1,4-二恶烷和丙酮(DMK)”混合物在0.1确定MPa在这项研究工作中。结果表明,氯吡喹的溶解度与所选溶剂中的温度成正比。298.15 K时的一般溶解度顺序为:1,4-二恶烷(0.0751)> 2-乙氧基乙醇(0.0333)>  n-PrAC(0.0297)> 2-甲氧基乙醇(0.0291)> EtAC(0.0269)> MtAC(0.0245)> IPrAC(0.0232)> DMK(0.0200)>  n-PrOH(0.0076)> EtOH(0.0058)> IPrOH(0.0045)> MtOH(0.0042)。用Kamlet,Abboud和Taft线性溶剂化能量关系(KAT-LSER)模型研究了溶剂对氯喹喹溶解度的影响,结果表明,溶剂-溶剂相互作用的敏感性(52.16%)远高于溶质-溶剂相互作用的敏感性。 (26.22%)。此外,五个活度系数函数(Margules,NRTL,Wilson,NRTL-SAC和UNIQUAC模型)用于与溶解度数据的相关性。平均ARD(平均相对偏差)低于2.01%,平均RMSD(均方根偏差)低于5.87E-4。五个选定模型提供了与实验溶解度值的良好一致性。此外,通过Wilson模型计算混合热力学性质,

更新日期:2020-03-31
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