Investigation on solid–liquid equilibrium behavior of ethyl ((1R,2S,5R)-2-isopropyl-5-methylcyclohexane-1-carbonyl) glycinate in twelve mono solvents: Determination, correlation, molecular simulation and thermodynamic analysis

IF 2.2 3区工程技术 Q3 CHEMISTRY, PHYSICAL Journal of Chemical Thermodynamics Pub Date : 2024-08-06 DOI:10.1016/j.jct.2024.107363

Haifang Mao , Tingting Liu , Xinlei Li , Yanghao Huo , Qiang Zhang , Pin Yang , Mengjie Luo , Jibo Liu , Miaomiao Jin

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Abstract

Ethyl ((1R,2S,5R)-2-isopropyl-5-methylcyclohexane-1-carbonyl) glycinate (Cooling agent WS-5) is an important cooling menthane carboxamide. In this work, the solid–liquid equilibrium data of WS-5 in twelve mono solvents (namely methanol, ethanol, n-propanol, isopropanol, methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, acetone, acetonitrile and cyclohexanone) were measured by a laser dynamic method from 278.15 K to 313.15 K under 101.6 ± 1.2 kPa. In the studied temperature range, the solubility of WS-5 correlated positively with temperature. Subsequently, the solubility data were correlated with the van’t Hoff equation, modified Apelblat equation, λh equation, Wilson model, and NRTL model, respectively. It was found that the modified Apelblat equation showed the best fitting performance with the smallest average values of RAD (relative average deviation) and RMSD (root mean square deviation), and the average values of RAD and RMSD were 0.94 % and 0.19 %, respectively. In order to explain the dissolution behavior of WS-5 in different solvents, the intermolecular interactions were analyzed using Hirshfeld surface (HS) analysis and molecular electrostatic potential surface (MEPS). Then, the molecular dynamic (MD) calculation was carried out, and the radial distribution function (RDF) analysis was employed to explain the intermolecular interaction between WS-5 and solvent molecules. Besides, the solvent properties, including polarity, hydrogen bond, cohesive energy, density, and viscosity, were compared to analyze the solid–liquid equilibrium behavior of WS-5. In addition, the thermodynamic properties of dissolution ( ${Δ G}_{s o l}$ , ${Δ H}_{s o l}$ and ${Δ S}_{s o l}$ ) of WS-5 were calculated, and the results implied that the dissolution process of WS-5 was endothermic and entropy-driven.

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甘氨酸乙酯（(1R,2S,5R)-2-异丙基-5-甲基环己烷-1-甲酰基）在十二种单溶剂中的固液平衡行为研究：测定、相关性、分子模拟和热力学分析

((1R,2S,5R)-2-异丙基-5-甲基环己烷-1-甲酰)甘氨酸乙酯（冷却剂 WS-5）是一种重要的冷却薄荷烷羧酰胺。本研究采用激光动态法测定了 WS-5 在 12 种单溶剂（即甲醇、乙醇、正丙醇、异丙醇、醋酸甲酯、醋酸乙酯、醋酸正丙酯、醋酸异丙酯、醋酸正丁酯、丙酮、乙腈和环己酮）中的固液平衡数据，温度范围为 278.15 至 313.15，条件为 101.6 ± 1.2。在研究的温度范围内，WS-5 的溶解度与温度呈正相关。随后，溶解度数据分别与范特霍夫方程、修正的阿佩尔布拉特方程、方程、威尔逊模型和 NRTL 模型相关联。结果发现，修正的阿佩尔布拉特方程的拟合效果最好，其平均值（相对平均偏差）和（均方根偏差）最小，平均值和分别为 0.94 % 和 0.19 %。为了解释 WS-5 在不同溶剂中的溶解行为，利用 Hirshfeld 表面（HS）分析和分子静电位面（MEPS）分析了分子间的相互作用。然后，进行了分子动力学（MD）计算，并利用径向分布函数（RDF）分析解释了 WS-5 与溶剂分子之间的分子间相互作用。此外，还比较了溶剂的性质，包括极性、氢键、内聚能、密度和粘度，以分析 WS-5 的固液平衡行为。此外，还计算了 WS-5 的溶解热力学性质（、和），结果表明 WS-5 的溶解过程是内热和熵驱动的。

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来源期刊

Journal of Chemical Thermodynamics 工程技术-热力学

CiteScore

5.60

自引率

15.40%

发文量

199

审稿时长

79 days

期刊介绍： The Journal of Chemical Thermodynamics exists primarily for dissemination of significant new knowledge in experimental equilibrium thermodynamics and transport properties of chemical systems. The defining attributes of The Journal are the quality and relevance of the papers published. The Journal publishes work relating to gases, liquids, solids, polymers, mixtures, solutions and interfaces. Studies on systems with variability, such as biological or bio-based materials, gas hydrates, among others, will also be considered provided these are well characterized and reproducible where possible. Experimental methods should be described in sufficient detail to allow critical assessment of the accuracy claimed. Authors are encouraged to provide physical or chemical interpretations of the results. Articles can contain modelling sections providing representations of data or molecular insights into the properties or transformations studied. Theoretical papers on chemical thermodynamics using molecular theory or modelling are also considered. The Journal welcomes review articles in the field of chemical thermodynamics but prospective authors should first consult one of the Editors concerning the suitability of the proposed review. Contributions of a routine nature or reporting on uncharacterised materials are not accepted.