Solubility of tridecanedioic acid in pure solvent systems: An experimental and computational study

Tang, Weiwei; Dai, Heng; Feng, Yi; Wu, Songgu; Bao, Ying; Wang, Jingkang

doi:10.1016/j.jct.2015.05.026

Cited by 42 publications

(12 citation statements)

References 40 publications

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“…As the value of acceptor propensity of acetone and ethyl acetate is larger than others, in this case, capacity to form hydrogen bonds of acetone and ethyl acetate with benzoin should be stronger. Furthermore, the degree of solvent–solvent association is one of the factors that influence the solubility, which could be represented by cohesive energy density. , In the binary solvent mixture of ethyl acetate + methanol or ethanol, when mole fraction of methanol is 0.1 (0.2 for ethanol) the solubility of benzoin reaches maximum. This phenomenon was found and reported several years ago by Gordon et al, Acree, and Smith et al − In a solute-free solvent, the interaction between solvent molecules reaches internal equilibrium, while when solute is added, original bonds must be broken and replaced by new bonds between solvent and solute.…”

Section: Resultsmentioning

confidence: 99%

Solubility of Benzoin in Six Monosolvents and in Some Binary Solvent Mixtures at Various Temperatures

Yang

Tang

et al. 2017

J. Chem. Eng. Data

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The solubility of benzoin in monosolvents (acetone, ethyl acetate, methanol, ethanol, 1-propanol, and 1-butanol) and binary solvent mixtures (ethyl acetate + methanol, ethyl acetate + ethanol) was measured using UV–vis spectroscopy at temperatures ranging from 283.15 K to 323.15 K. It can be seen from the data that the solubility of benzoin increases expectedly as temperature increases in a given solvent or solvent mixture, the solubility in acetone is maximum among six monosolvents which could be well explained by the existence of strong H-bonds, rather than the “like dissolves like” rule. In binary solvent mixtures, the solubility reaches maximum when the mole fraction of methanol is 0.1 in ethyl acetate + methanol mixed solvents, while the maximum exhibits at 0.2 of mole fraction of ethanol in ethyl acetate + ethanol. The solubility parameter was interpreted as the cosolvency of benzoin solubility in binary solvent mixtures. The solubility data were correlated by modified Apelbalt equation, CNIBS/R-K equation, λh equation, Jouyban–Acree model, and Van’t–JA equation. Mixing thermodynamic properties were further calculated and discussed regarding their roles in dissolution and solubility.

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Section: Resultsmentioning

confidence: 99%

Solubility of Benzoin in Six Monosolvents and in Some Binary Solvent Mixtures at Various Temperatures

Yang

Tang

et al. 2017

J. Chem. Eng. Data

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“…The solubilities of metastable form II diacids were determined by the dynamic method using the laser monitoring observation technique. Other necessary data relating to equilibrium solubility were obtained from previous work (Tang et al, 2015;Zhang et al, 2014) by the same measurement method. Details of the experimental apparatus and process of gravimetric analysis (Shi et al, 2019) are given in the supporting information and the solubility data are given in Table S1.…”

Section: Solubility Measurementmentioning

confidence: 99%

Probing the structural pathway of conformational polymorph nucleation by comparing a series of α,ω-alkanedicarboxylic acids

Shi

et al. 2020

IUCrJ

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Herein the nucleation pathway of conformational polymorphs was revealed by studying the relationships and distinctions among a series of α,ω-alkanedicarboxylic acids [HOOC–(CH2) n−2–COOH, named DAn, where n = 5, 7, 9, 11, 13, 15] in the solid state and in solution. Their polymorphic outcomes, with the exception of DA5, show solvent dependence: form I with conformation I crystallizes from solvents with hydrogen-bond donating (HBD) ability, whereas form II with conformation II crystallizes preferentially from solvents with no HBD ability. In contrast, form II of DA5 does not crystallize in any of the solvents used. Quantum mechanical computation showed that there is no direct conformational link between the solvents and the resultant polymorphic outcomes. Surprisingly, solute aggregates were found in no-HBD solvents by Fourier transform infrared spectroscopy, and only monomers could be detected in HBD solvents, suggesting stronger solvation. Furthermore, it was found that all six compounds including DA5 followed the same pattern in solution. Moreover, crystal-packing efficiency calculations and stability tests stated that dimorphs of DA5 bear a greater stability difference than others. These suggest that the rearrangement from conformation II to I could not be limited by hard desolvation in HBD solvents, where form I was also obtained. In other systems, metastable II was produced in the same solvents, probably as a result of the rearrangement being limited by hard desolvation. In this work, a comparative study uncovers the proposed nucleation pathway: difficulty in desolvation has a remarkable effect on the result of rearrangement and nucleation outcome.

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“…Afterwards, all‐atom MD simulations were performed on the solvents studied (five pure solvents and one solvent mixture) at T = 298.15 K, p = 0.1 MPa. The force field selected was the condensed‐phase optimized molecular potentials for atomistic simulation studies (COMPASS) , . The cubical boxes were created using Amorphous Cell tools.…”

Section: Methodsmentioning

confidence: 82%

“…On the other hand, detailed information on the intermolecular interactions during the solvation process remains unknown. The continuous growth in computational technologies such as molecular dynamics (MD) simulation allows calculation of a molecular system with structural and conformational changes, which is a key issue for interpreting the solvation mechanism . MD simulation is an attractive tool for further discovering the dissolution behavior.…”

Section: Introductionmentioning

confidence: 95%

Experimental Assessment and Modeling of the Solubility of Malonic Acid in Different Solvents

Wang

et al. 2018

Chem Eng & Technol

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Malonic acid is widely applied in the pharmaceutical industry as a drug intermediate and for acidity control in drug production. Its solubility in five pure solvents and one binary solvent mixture was measured. The results reveal that, in the solvents studied, the solubility increases with increasing temperature. Different thermodynamic models were applied to correlate the solubility data in the pure and binary solvents and were found to match well with the experimental data. Computational investigations performed using molecular dynamics simulations showed that, in the pure alcohol solvents, both the solute‐solvent interaction and the solvent‐solvent interaction affect the solubility behavior, while in the case of the pure solvents acetone and acetonitrile, the solute‐solvent interaction is the key factor.

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Solubility of tridecanedioic acid in pure solvent systems: An experimental and computational study

Cited by 42 publications

References 40 publications

Solubility of Benzoin in Six Monosolvents and in Some Binary Solvent Mixtures at Various Temperatures

Solubility of Benzoin in Six Monosolvents and in Some Binary Solvent Mixtures at Various Temperatures

Probing the structural pathway of conformational polymorph nucleation by comparing a series of α,ω-alkanedicarboxylic acids

Experimental Assessment and Modeling of the Solubility of Malonic Acid in Different Solvents

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