Solubility of Terephthaldialdehyde in N-Methyl-2-pyrrolidone and Solid–Liquid Phase Equilibrium for Ternary Systems of Terephthalic Acid + Terephthaldialdehyde + N,N-Dimethylformamide/N-Methyl-2-pyrrolidone

Li, Xinbao; Liu, Yu; Xu, An; Ma, Zhiyuan; Wang, Jian; Zhao, Hongkun

doi:10.1021/acs.jced.8b00091

Cited by 7 publications

(20 citation statements)

References 21 publications

(61 reference statements)

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“…Solubility x of terephthalic acid: ■, tetrahydrofuran measured in this work; □, tetrahydrofuran in ref . ●, cyclohexanone measured in this work; ○, cyclohexanone in ref ; ▲, N , N -dimethylformamide measured in this work; △, N , N -dimethylformamide in refs and ; ▼, ref ; ▽, ref ; ★, ref .…”

Section: Methodsmentioning

confidence: 83%

“… a Standard uncertainties u are u ( T ) = 0.13 K, u r ( p ) = 0.05, and u r ( x ) = 0.05. b x represents the experimental molar fraction of solubility. c RD is the relative deviation between the experimental solubility data and the literature data. − ,− d ARD is the averaged relative deviation. …”

Section: Methodsmentioning

confidence: 99%

“… c RD is the relative deviation between the experimental solubility data and the literature data. − ,− …”

Section: Methodsmentioning

confidence: 99%

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Measurement and Correlation of Solubilities of 4-Methylbenzoic Acid and Terephthalic Acid in Eight Organic Solvents

et al. 2021

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In this study, the solubility of 4-methylbenzoic acid and terephthalic acid in N-methylformamide, 1,3-dimethyl-2-imidazolidinone, N-methylformanilide, 2-ethyl-1-hexanol, tetrahydrofuran, cyclohexanone, acetophenone, and ethylene glycol diethyl ether was measured using the laser dynamic method under 101.3 kPa at the temperature ranging from 293.65 to 344.35 K. The measured results showed that the solubility of 4-methylbenzoic acid and terephthalic acid increased with the increasing temperature. The solubility of 4methylbenzoic acid is greater than that of terephthalic acid in the same solvents. The modified Apelblat model and the modified nonrandom two-liquid (NRTL) activity coefficient model were utilized to correlate the solubility of 4-methylbenzoic acid and terephthalic acid in each solvent. The calculated solubility agreed satisfactorily with the measured results with 1.67/1.91% averaged relative deviation (ARD) for terephthalic acid and 0.62/0.69% for 4-methylbenzoic acid in the modified NRTL/Apelblat model, respectively. The result of the Akaike Information Criterion (AIC) analysis showed that the modified Apelblat model was better at correlating the solubility of 4-methylbenzoic acid in 1,3-dimethyl-2-imidazolidinone, ethylene glycol diethyl ether, tetrahydrofuran, acetophenone, N-methylformamide, acetophenone, and terephthalic acid in 1,3dimethyl-2-imidazolidinone; the modified NRTL model performs better in correlating the solubility of 4-methylbenzoic acid in Nmethylformanilide, N-methylformamide, 2-ethyl-1-hexanol, and terephthalic acid in 2-ethyl-1-hexanol, 2-ethyl-1-hexanol, and cyclohexanone N-methylformanilide.

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Section: Methodsmentioning

confidence: 83%

Section: Methodsmentioning

confidence: 99%

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Measurement and Correlation of Solubilities of 4-Methylbenzoic Acid and Terephthalic Acid in Eight Organic Solvents

et al. 2021

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“…Supposing that the dependence of model parameters in relation to interaction energy upon the reciprocal of temperature is a linear relatioship, − the parameters τ ij in the NRTL model and Λ ij in the Wilson model are described by The symbols a ij and b ij in eqs and refer to constants that are independent of the experiment temperature.…”

Section: Solubility Modelsmentioning

confidence: 99%

Solid–Liquid Ternary Phase Equilibrium of 3,5-Dibromo-4-hydroxybenzaldehyde + 3-Bromo-4-hydroxybenzaldehyde + N,N-Dimethylformamide/1,4-dioxane/dimethylsulfoxide: Determination and Model Correlation

Xie

Xue

et al. 2021

J. Chem. Eng. Data

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The solid−liquid ternary phase equilibrium for 3,5-dibromo-4-hydroxybenzaldehyde + 3-bromo-4-hydroxybenzaldehyde + N,N-dimethylformamide/1,4-dioxane/dimethylsulfoxide systems was experimentally obtained through the shake-flask method at three temperatures of 298.15, 308.15, and 318.15 K under a normal pressure of 101.2 kPa. Nine isothermal phase diagrams of the three systems were constructed by means of the mutual solubility data acquired. The equilibrated solids with different solvent systems were identified by Schreinemakers' wet residue method. Two neat solids corresponding to pure 3-bromo-4hydroxybenzaldehyde and pure 3,5-dibromo-4-hydroxybenzaldehyde appeared in each equilibrium system at a specific temperature. The saturated regions of pure 3-bromo-4hydroxybenzaldehyde and 3,5-dibromo-4-hydroxybenzaldehyde positively increased as the temperature decreased. The saturated region of 3,5-dibromo-4-hydroxybenzaldehyde was bigger than that of 3-bromo-4-hydroxybenzaldehyde at the same conditions. Two activity coefficient models, NRTL and Wilson models, were utilized to mathematically describe the solid−liquid phase equilibrium. The back-calculated solubility data through the NRTL model were in good agreement with the experiment ones. The ternary phase diagrams and mutual solubility data for these systems are crucial in the purification of 3-bromo-4-hydroxybenzaldehyde and 3,5-dibromo-4-hydroxybenzaldehyde mixtures.

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“…Under atmospheric pressure, it sublimes at 675 K and has a melting point of 700 K (triple point) in a sealed tube. − These aspects may explain the low solubility of TA in nonbasic solvents such alcohols . Although the solubility of TA is already reported for some solvents, such as N , N -dimethylformamide (DMF), − dimethyl sulfoxide (DMSO), ,, 1-methyl-2-pyrrolidinone (NMP), − ,− and N , N -dimethylacetamide (DMAC), ,,, there is no data available about its solubility in pyridine (PY) and 2EH. Furthermore, there is no information in the literature about the solubility of TA in binary mixtures composed of 2EH and the above-cited solvents, which could be of industrial interest to improve the esterification reaction.…”

Section: Introductionmentioning

confidence: 99%

Measurement and Correlation of the Solubility of Terephthalic Acid in Six Pure Solvents and Five Binary Mixtures

et al. 2021

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The goal of this work was to measure the solubility of terephthalic acid (TA) in six pure solvents (2-ethyl-1-hexanol (2EH), dimethyl sulfoxide, 1-methyl-2-pyrrolidinone, N,N-dimethylformamide, N,N-dimethylacetamide, and pyridine) and five binary mixtures (composed of 2EH and 5 or 10% w/w another solvent) from 313.15 to 363.15 K at atmospheric pressure 101.3 kPa. Experiments were performed by an isothermal method employing an in situ filter to sample only the homogeneous liquid phase, and samples were analyzed by liquid chromatography. Solubility of TA in 2EH is 100-fold lower when compared to the other studied solvents, but a binary mixture composed of 2EH and 5 or 10% w/w (solute-free basis) dimethyl sulfoxide could increase solubility up to 61 and 165%, respectively. Furthermore, the parameters of λh, Apelblat, Wilson, and NRTL models were estimated. All of the models fitted the experimental data with good agreement, but the nonrandom two-liquid (NRTL) model was the most suitable to represent experimental data.

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Solubility of Terephthaldialdehyde in N-Methyl-2-pyrrolidone and Solid–Liquid Phase Equilibrium for Ternary Systems of Terephthalic Acid + Terephthaldialdehyde + N,N-Dimethylformamide/N-Methyl-2-pyrrolidone

Cited by 7 publications

References 21 publications

Measurement and Correlation of Solubilities of 4-Methylbenzoic Acid and Terephthalic Acid in Eight Organic Solvents

Measurement and Correlation of Solubilities of 4-Methylbenzoic Acid and Terephthalic Acid in Eight Organic Solvents

Solid–Liquid Ternary Phase Equilibrium of 3,5-Dibromo-4-hydroxybenzaldehyde + 3-Bromo-4-hydroxybenzaldehyde + N,N-Dimethylformamide/1,4-dioxane/dimethylsulfoxide: Determination and Model Correlation

Measurement and Correlation of the Solubility of Terephthalic Acid in Six Pure Solvents and Five Binary Mixtures

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