Exploring the Dissolution Behavior of <i>m</i>-Hydroxybenzoic Acid in 14 Pure Solvents Using Thermodynamic, Molecular Simulation and Hansen Solubility Parameters

Liu, Wenju; Yang, Xiaolong; Shi, Paifeng; Wang, Shaofeng; Wang, Han; Shen, Yanmin

doi:10.1021/acs.jced.3c00462

Cited by 4 publications

(3 citation statements)

References 67 publications

(89 reference statements)

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“…Then, after loading the optimized structure into the Multiwfn application, MEPS analysis was completed. Finally, visual molecular dynamics (VMD) software was used to graphically present the computing results. , …”

Section: Methodsmentioning

confidence: 99%

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Solubility Behavior and Data Correlation of N-Acetyl-l-valine in 12 Individual Solvents at Multiple Temperatures

Wang,

Zhang,

Wang

et al. 2024

J. Chem. Eng. Data

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N-Acetyl-L-valine is a crucial pharmaceutical intermediate, and research on the solubility behavior of N-acetyl-L-valine in organic solvents is necessary for processes of crystallization and separation. The solubility data of N-acetyl-L-valine in 12 pure solvents (water, 2-butanone, dimethyl carbonate, n-propanol, isopropanol, n-butanol, isobutanol, acetone, acetonitrile, methyl acetate, ethyl acetate, and 1,4-dioxane) ranging from 283.15 to 323.15 K were measured by the static gravimetric method. Its solubility in all studied solvents increases with the increase of temperature. Moreover, the solubility sequence at 298.15 K is n-propanol > isopropanol > n-butanol > isobutanol > 1,4dioxane > acetone > 2-butanone > water > methyl acetate > ethyl acetate > acetonitrile > dimethyl carbonate. The solubility behavior is primarily determined by the solvent polarity (E T (30)), hydrogen bonding, and cohesive energy density. Hirshfeld surface analysis (HS) and molecular electrostatic potential surface (MEPS) analysis were used to determine the internal interactions within N-acetyl-L-valine solutions. Four solubility fitting models were used to correlate the experimental mole fraction solubility data, including the modified Apelblat model, the λh equation, the NRTL model, and the UNIQUAC model. Furthermore, the NRTL model was utilized to calculate the mixing thermodynamic characteristics of N-acetyl-L-valine in these solvents. The results indicated that the mixing process was entropydriven and spontaneous.

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Section: Methodsmentioning

confidence: 99%

“…Finally, visual molecular dynamics (VMD) software was used to graphically present the computing results. 19,20…”

Section: Characterizationmentioning

confidence: 99%

Solubility Behavior and Data Correlation of N-Acetyl-l-valine in 12 Individual Solvents at Multiple Temperatures

Wang,

Zhang,

Wang

et al. 2024

J. Chem. Eng. Data

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show abstract

“…The optimized structure is loaded into the Multiwfn program using the density functional theory (DFT) method at the B3LYP-/6-31G(d,p) level. The results of the calculations are then displayed graphically using the VMD (Visual Molecular Dynamics) software. ,, …”

Section: Experimental Sectionmentioning

confidence: 99%

Determination of 1,4-Diethoxybenzene Solubility in 12 Monosolvent Systems at Multiple Temperatures from 278.15 to 318.15 K

Zhao,

Xing,

Xiao

et al. 2024

J. Chem. Eng. Data

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1,4-Diethoxybenzene is an important organic synthesis intermediate used in the synthesis of pesticides, pharmaceuticals, fuels, and reagents. In the absence of relevant solubility data for 1,4-diethoxybenzene, it is necessary to study in detail its solubility behavior in various solvents. The solubility data for 1,4-diethoxybenzene in 12 pure solvents, including methanol, ethanol, acetone, 2-butanone, acetonitrile, dimethyl carbonate, ethyl lactate, methyl acetate, ethyl acetate, n-propyl acetate, and isobutyl acetate, was determined. Experiments showed that the solubilities of 1,4-diethoxybenzene molar fractions all increased with increasing temperature. The order of their solubility at 298.15 K is as follows: butyl acetate (0.212 mol/mol) > ethyl acetate (0.179 mol/mol) > 2-butanone (0.169 mol/mol) > n-propyl acetate (0.165 mol/mol) > methyl acetate (0.145 mol/mol) > acetone > isobutyl acetate (0.112 mol/mol) > dimethyl carbonate (0.099 mol/mol) > ethyl lactate (0.074 mol/mol) > acetonitrile (0.067 mol/ mol) > ethanol (0.015 mol/mol) > methanol (0.009 mol/mol). Modified Apelblat models, Margules models, UNIQUAC models, and NRTL models were used for correlation of solubility data. The results of ARD and RMSD obtained from the calculations show that each model correlates well with the experimental data. In particular, better solubility correlation results were obtained with the modified Apelblat model. Hirshfeld surface (HS) analysis and molecular electrostatic potential surfaces (MEPS) were utilized to analyze the interactions within 1,4-diethoxybenzene solutions. The Hansen solubility parameters (HSPs) were utilized to assess the solvents' capability and to elucidate its ability to dissolve 1,4-diethoxybenzene. The main factors influencing the solubility behavior include solvent polarity (E T (30)), hydrogen bond, cohesive energy density, and Hansen solubility parameters (HSPs). Furthermore, mixing thermodynamic characteristics of 1,4-diethoxybenzene in selected solvents were calculated by the NRTL model, which revealed that the mixing process was spontaneous and entropy driven. These experimental results can be used for the purification, crystallization, and industrial applications of 1,4-diethoxybenzene as well as similar substances. Therefore, it is necessary to study the solvation behavior of 1,4-diethoxybenzene in different monosolvents to provide sufficient data for the design of its crystallization process.

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Solubility of N-Acetyl-L-glutamine in twelve Mono-solvents: Characterization, Determination, Analysis, and model correlation

Liu,

Wang,

Zhang

et al. 2024

Journal of Molecular Liquids

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Exploring the Dissolution Behavior of m-Hydroxybenzoic Acid in 14 Pure Solvents Using Thermodynamic, Molecular Simulation and Hansen Solubility Parameters

Cited by 4 publications

References 67 publications

Solubility Behavior and Data Correlation of N-Acetyl-l-valine in 12 Individual Solvents at Multiple Temperatures

Solubility Behavior and Data Correlation of N-Acetyl-l-valine in 12 Individual Solvents at Multiple Temperatures

Determination of 1,4-Diethoxybenzene Solubility in 12 Monosolvent Systems at Multiple Temperatures from 278.15 to 318.15 K

Solubility of N-Acetyl-L-glutamine in twelve Mono-solvents: Characterization, Determination, Analysis, and model correlation

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