Phase Equilibria in Systems of Morpholine, Acetonitrile, and <i>n</i>-Alkanes

Riechert, Ole; Zeiner, Tim; Sadowski, Gabriele

doi:10.1021/acs.jced.5b00175

Cited by 7 publications

(5 citation statements)

References 31 publications

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“…Finally, another issue is the dipole moment value itself and its treatment. While in PCS-μ we used the overall molecular dipole moment with n μ, DLG = 1 (as usual in the literature for compounds of this molecular size ,, ), Baird et al set n μ, DLG to 3 for PCS-μ-EX to reflect the presence of three distinct oxygenated polar groups in the DLG molecules. This idea can be considered reasonable.…”

Section: Resultsmentioning

confidence: 99%

Thermodynamic Properties and Phase Equilibria of Dihydrolevoglucosenone and Its Mixtures with Hydrocarbons

Jeřábek,

Štejfa,

Klajmon

et al. 2023

J. Chem. Eng. Data

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Thermodynamic and computational study of a biomass-derived solvent dihydrolevoglucosenone (DLG) and its mixtures with hydrocarbons is presented in this work. Density and dynamic viscosity of DLG were measured within the temperature range of 293.15−353.15 K. Phase behavior of DLG above 183 K was analyzed using heat-flux differential scanning calorimetry, providing data on its melting temperature and enthalpy of fusion. Heat capacity of DLG was measured using a Tian-Calvet calorimeter at temperatures between 253 and 353 K. Two static apparatuses were utilized to measure the vapor pressure of DLG in the temperature range of 253−363 K. A thermodynamically consistent description was achieved by simultaneous correlation of experimental values of phase behavior, heat capacities, vapor pressures, and theoretical calculations. Liquid−liquid equilibria (LLE) data in four binary DLG and hydrocarbons (n-hexane, cyclohexane, n-decane, and ntetradecane) systems were determined using a combination of volumetric, cloud-point, and direct analytical methods. The obtained LLE data were employed to thermodynamically describe the binary mixtures using the nonrandom two-liquid (NRTL) equation and estimate critical points using the Extended-Scaling Law (ESL) equation. Furthermore, the pure-component data developed in this work were used to determine two new sets of parameters for DLG within the perturbed-chain statistical associating fluid theory (PC-SAFT) equation of state: one with and one without the explicit inclusion of the dipole moment of DLG in the model theory. In addition, one more set of parameters for DLG developed earlier by other authors was included. PC-SAFT with all three parameter sets was then examined in terms of its performance regarding the description of the LLE in the systems studied. Both correlations (with optimized k ij ) and pure predictions (k ij = 0) were considered and discussed. Interestingly, it appears that the better PC-SAFT with a particular parameter set for DLG performs for the properties of pure DLG, the worse are the results for the LLE in the DLG + hydrocarbon systems. For example, PC-SAFT with the nonpolar parameters for DLG provided more accurate results for pure DLG than its polar counterparts, while it quantitatively failed for the LLE.

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Section: Resultsmentioning

confidence: 99%

Thermodynamic Properties and Phase Equilibria of Dihydrolevoglucosenone and Its Mixtures with Hydrocarbons

Jeřábek,

Štejfa,

Klajmon

et al. 2023

J. Chem. Eng. Data

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“…Moreover, •, predictions of the original UNIFAC model; ▲, predictions of the COSMO-SAC-UNIFAC model; ★, predictions of the COSMO-SAC model; ■ , experimental data. 23,24 The experimental data points come from ref 24 (copyright 2016 Elsevier B.V.) with permission. the COSMO-SAC-UNIFAC model prediction is the closest to experimental data.…”

Section: Resultsmentioning

confidence: 99%

“…VLE of the (a) methanol (1) + NMP (2), (b) morpholine (1) + acetonitrile (2), (c) DMF (1) + pyridine (2), and (d) N -methyl-2-pyrrolidone (1) + 1,2-dichloroethane (2) systems: black line, predictions of the COSMO-SAC model; dashed line, predictions of the original UNIFAC model; red line, predictions of the COSMO-SAC-UNIFAC model; ■, experimental data. − The experimental data points come from ref (copyright 1989 China National Knowledge Infrastructure (CNKI)) with permission.…”

Section: Resultsmentioning

confidence: 99%

“…LLE of the (a) sulfolane (1) + butanoic acid (2) + heptane (3) and (b) morpholine (1) + acetonitrile (2) + octane (3): , experimental tie line; ●, predictions of the original UNIFAC model; ▲, predictions of the COSMO-SAC-UNIFAC model; ★, predictions of the COSMO-SAC model; ■, experimental data. , The experimental data points come from ref (copyright 2016 Elsevier B.V.) with permission.…”

Section: Resultsmentioning

confidence: 99%

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Extension of the COSMO-UNIFAC Thermodynamic Model

Zhu

Taheri

Zhang

et al. 2020

Ind. Eng. Chem. Res.

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In this work, a priori COSMO-SAC model was combined with the original UNIFAC model, and thus the new COSMO-SAC-UNIFAC thermodynamic model with a strong predictive power for fluid phase equilibrium (VLE, LLE) was proposed. By this means the group binary parameter matrix of original UNIFAC model was extended by introducing the new 648 vacant parameter pairs for 51 main functional groups for the conventional substances in this work. Moreover, the combined thermodynamic model was first applied to process simulation on gas drying with ionic liquids (ILs). To verify the reliability of the COSMO-SAC-UNIFAC model, the predictive values were directly compared with experimental data coming from this work, our previous work, and literature. The moderately accurate predictions of the COSMO-SAC-UNIFAC model demonstrate the high potential applicability of this new model, especially for numerous systems with missing parameters including ILs, which are normally encountered in the original UNIFAC model.

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“…It can also be used as a solvent or as a chemical intermediate to produce 2-vinylpyridine. − 3-Methylpyridine (synonyms: 3-picoline, β-picoline) is often used as a starting substance for pharmaceuticals and agrochemicals including insecticides, feed additives, and herbicides . Sulfolane is used as a high polarity solvent for extraction of BTXs (benzene, toluene, and xylene isomers) , and as hybrid solvent for removing H 2 S and CO 2 in sour gas treatment processes. − Morpholine is used largely in the rubber industry (as an intermediate, stabilizer, or bloom inhibitor), steam boiler systems (as corrosion inhibitor against carbonic acid), pharmaceuticals (as an intermediate), and the detergent industry (as a brightener). − Trioxane is considered as the basic chemical during the production of polyacetal resin from formaldehyde in acidic aqueous solutions. − As probe molecules in heterogeneous catalysis, furan and its family are of great interest for a variety of chemical reactions . Some furan derivatives (2-methylfuran, 2,5-dimethylfuran, γ-valerolactone) obtained from cellulosic biomass have the immense potential to be used as biofuels for substitution or relieving the petroleum-based fuels. − Benzofuran derivatives have remarkable biological potentials and can be used as antitumor, kinase inhibitor, antimicrobial, analgesic, antihyperglycemic, and antiparasitic agents. − Tetrahydrofurfuryl alcohol (THFA) is extensively used as a water-miscible solvent or chemical intermediate in the production of THFA acrylates, UV curables, esters of oleic/stearic acids, and formulation of epoxy resins .…”

Section: Introductionmentioning

confidence: 99%

Phase Behavior Modeling of Mixtures Containing N-, S-, and O-Heterocyclic Compounds Using PC-SAFT Equation of State

Razavi

Khoshsima

Shahriari

2019

Ind. Eng. Chem. Res.

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In this study, thermodynamic modeling of mixtures including heterocyclic compounds using the perturbed chain statistical associating fluid theory (PC-SAFT) equation of state (EoS) is studied. The oxygen-, nitrogen-, or sulfur-containing heterocyclic molecules are modeled as nonassociating components. For some more aggregative associating compounds with −OH (furfuryl alcohol, tetrahydrofurfuryl alcohol, 2-thiophenemethanol, and 5-hydroxymethylfurfural) or −NH (azetidine, aziridine, pyrrole, pyrazole, pyrrolidine, pyrrolidone, piperidine, morpholine, imidazole, piperazine, and n-methylpiperazine) groups, two association sites are considered for each molecule. The pure component parameters of the PC-SAFT EoS are adjusted to vapor pressure and liquid density experimental data with average absolute relative deviation of 0.88 and 0.77%, respectively. Using the obtained parameters, the isobaric and isothermal phase behavior of binary systems is studied over a wide range of thermodynamic conditions. The average deviations between model calculations and experimental data for heterocycle + aromatics, heterocycle + cycloalkane, heterocycle + haloalkanes, heterocycle + alcohol, heterocycle + heterocycle, heterocycle + organic solvents, and heterocycle + hydrocarbon systems are about 1.79, 2.15, 1.03, 1.68, 2.81, 1.24, and 1.81% respectively. Furthermore, the solid–liquid equilibria of heterocycle mixtures have been predicted by estimation of melting and eutectic points over a wide range of compositions. The second-order-derivative thermodynamic properties of heterocyclic compounds including speed of sound (u s) and heat capacity (C p) have been also predicted. The obtained results are in good agreement with the experimental data.

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Phase Equilibria in Systems of Morpholine, Acetonitrile, and n-Alkanes

Cited by 7 publications

References 31 publications

Thermodynamic Properties and Phase Equilibria of Dihydrolevoglucosenone and Its Mixtures with Hydrocarbons

Thermodynamic Properties and Phase Equilibria of Dihydrolevoglucosenone and Its Mixtures with Hydrocarbons

Extension of the COSMO-UNIFAC Thermodynamic Model

Phase Behavior Modeling of Mixtures Containing N-, S-, and O-Heterocyclic Compounds Using PC-SAFT Equation of State

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