Vapor Pressures and Phase Changes Enthalpy and Gibbs Energy of Three Crystalline Monomethyl Benzenedicarboxylates

Monte, Manuel J.S.; Sousa, Carlos A. D.

doi:10.1021/je0503305

Cited by 10 publications

(7 citation statements)

References 13 publications

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“…And the molar enthalpies of fusion of DMT and MMT measured by DSC are 34.87 ± 0.30 kJ·mol –1 and 39.73 ± 0.38 kJ·mol –1 , respectively. These data are close to the values reported by Elliot and Chris (31.65 kJ·mol –1 for DMT), Dozen et al (32.9 kJ·mol –1 for DMT), and Monte and Sousa (37.68 kJ·mol –1 for MMT) …”

Section: Results and Discussionsupporting

confidence: 90%

Solubility of Dimethyl Terephthalate and Monomethyl Terephthalate in the Methanol Aqueous Solution and Its Application To Recycle Monomethyl Terephthalate from Crude Dimethyl Terephthalate

Zhang

Xia

Yang

et al. 2013

Ind. Eng. Chem. Res.

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The solubilities of dimethyl terephthalate (DMT) and monomethyl terephthalate (MMT) in methanol aqueous solutions were determined in the temperature range of 280−336 K. The solute-free mass fractions of methanol extended from 0.3 to 1.0. Both the solubilities of DMT and MMT in aqueous methanol solution increase with the temperature and the addition of methanol. The experimental data were correlated with the Wilson and the NRTL models. The root-mean-square deviations for the system of (DMT + methanol + water) were 1.30 and 1.33 K calculated by the Wilson and the NRTL models, respectively, while for the system of (MMT + methanol + water), the root-mean-square deviations were 0.55 and 0.82 K. The melting points and the enthalpy of fusion of DMT and MMT were detected by the differential scanning calorimetry (DSC). A simple purification and recycling process was designed to separate MMT from the esterification reaction product according to the solubility difference between DMT and MMT.

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Section: Results and Discussionsupporting

confidence: 90%

Solubility of Dimethyl Terephthalate and Monomethyl Terephthalate in the Methanol Aqueous Solution and Its Application To Recycle Monomethyl Terephthalate from Crude Dimethyl Terephthalate

Zhang

Xia

Yang

et al. 2013

Ind. Eng. Chem. Res.

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“…In previous works from our research group, correlations between enthalpies of sublimation and temperature of sublimation at a reference pressure were derived for families of several compounds (hydroxyquinolines, quinoxalines, carboxylic acids − ). Recently, similar correlations have been derived between Δ cr g H m o (298.15 K) and Δ cr g G m o (298.15 K) , for several substitued benzenedicarboxylates and for para -benzoic acids, and it was observed that the quality of such correlations is significantly enhanced when the temperature of fusion of the several para -benzoic acids was also considered as independent variable . Figure shows the graphic representation of Δ cr g G m o (298.15 K) = f {Δ cr g H m o (298.15 K)}.…”

Section: Resultssupporting

confidence: 57%

Thermodynamic Study on the Sublimation of Anthracene-Like Compounds

et al. 2010

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A Knudsen mass-loss effusion technique was used for measuring the vapor pressures at different temperatures of the following crystalline compounds: anthraquinone (CAS No. 84-65-1), between (377.06 and 395.03) K; anthrone (CAS No. 90-44-8), between (346.15 and 365.14) K; thianthrene (CAS No. 92-85-3), between (344.27 and 264.06) K; thioxanthone (CAS No. 492-22-8), between (369.12 and 387.20) K; and xanthone (CAS No. 90-47-1), between (342.22 and 362.22) K. From the temperature dependence of the vapor pressure of each crystalline compound, the standard (p o = 105 Pa) molar enthalpies and Gibbs energies of sublimation, at T = 298.15 K, were derived. The measured thermodynamic properties are compared with literature results for similar compounds, and correlations for estimation of the vapor pressures and enthalpy of sublimation for anthracene-like compounds are presented.

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“…Given that one would naturally expect a reasonable correlation between T Δ S and the molecular mass or number of rotatable bonds, it seems odd that the experimental terms do not reflect this. The average error margin for the T Δ S of sublimation quoted in the original literature source for the SUB-48 − data set is 0.79 kJ/mol (range 0.09–2.68 kJ/mol). The full SUB-48 data set and references to the original sources are given in Supporting Information Table S1.…”

Section: Resultsmentioning

confidence: 98%

“…These data could help greatly in the advancement of this field. We include our own data set in the Supporting Information, which has been curated from a wide variety of literature − for use in sublimation thermodynamics prediction.…”

Section: Discussionmentioning

confidence: 99%

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Are the Sublimation Thermodynamics of Organic Molecules Predictable?

McDonagh

Palmer

Mourik

et al. 2016

J. Chem. Inf. Model.

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We compare a range of computational methods for the prediction of sublimation thermodynamics (enthalpy, entropy and free energy of sublimation). These include a model from theoretical chemistry that utilizes crystal lattice energy minimization (with the DMACRYS program) and QSPR models generated by both machine learning (Random Forest and Support Vector Machines) and regression (Partial Least Squares) methods. Using these methods we investigate the predictability of the enthalpy, entropy and free energy of sublimation, with consideration of whether such a method may be able to improve solubility prediction schemes. Previous work has suggested that the major source of error in solubility prediction schemes involving a thermodynamic cycle via the solid state is in the modeling of the free energy change away from the solid state. Yet contrary to this conclusion other work has found that the inclusion of terms such as the enthalpy of sublimation in QSPR methods 2 does not improve the predictions of solubility. We suggest the use of theoretical chemistry terms, detailed explicitly in the methods section, as descriptors for the prediction of the enthalpy and free energy of sublimation. A dataset of 158 molecules with experimental sublimation thermodynamics values and some CSD refcodes has been collected from the literature and is provided with their original source references.

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Vapor Pressures and Phase Changes Enthalpy and Gibbs Energy of Three Crystalline Monomethyl Benzenedicarboxylates

Cited by 10 publications

References 13 publications

Solubility of Dimethyl Terephthalate and Monomethyl Terephthalate in the Methanol Aqueous Solution and Its Application To Recycle Monomethyl Terephthalate from Crude Dimethyl Terephthalate

Solubility of Dimethyl Terephthalate and Monomethyl Terephthalate in the Methanol Aqueous Solution and Its Application To Recycle Monomethyl Terephthalate from Crude Dimethyl Terephthalate

Thermodynamic Study on the Sublimation of Anthracene-Like Compounds

Are the Sublimation Thermodynamics of Organic Molecules Predictable?

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