Abstract
The selection and design of an optimal solvent for extractive distillation require reliable vapour–liquid phase equilibrium data and knowledge of extraction mechanisms. Compared with time-consuming experiments, molecular simulation presents great potential in research on the properties of fluids. Therefore, in this work, Gibbs ensemble Monte Carlo was applied to successfully predict the vapour–liquid phase equilibrium data of binary and ternary systems containing benzene, thiophene and N, N-dimethylformamide (DMF) at P = 101.3 kPa. The explicit hydrogen version of the transferable potentials for phase equilibria potential model was chosen for benzene and thiophene, whereas the OPLS potential model was selected for DMF. The predicted phase diagrams were compared with experimental data and the UNIQUAC thermodynamic model. A good agreement was obtained, which corroborated the validity of the potential models. In addition, the extraction mechanism was explored by radial distribution function (RDF) of the liquid-phase structure. The RDFs showed that thiophene and benzene shared a similar liquid-phase structure because of the intermolecular interaction. The distinct difference between the RDFs of DMF/benzene and those of DMF/thiophene is that the oxygen atom of DMF is more associated with hydrogen atoms of thiophene than that of benzene, which may be responsible for the extraction effect of DMF.
Similar content being viewed by others
References
Jiang B, Yang H, Zhang L et al (2015) Efficient oxidative desulfurization of diesel fuel using amide-based ionic liquids. Chem Eng J 283:89–96
Ibrahim JJ, Gao S, Yu L et al (2015) Extractive desulfurization of fuel oils with dicyano(nitroso) methanide-based ionic liquids. Sep Sci Technol 50(8):1166–1174
Zhang L, Feng J, Chu Q et al (2015) Effect of potassium on the catalytic performance of Ni2Mo3N catalyst during hydrogenation of thiophene-containing benzene. Catal Commun 66:50–54
Weitkamp J, Schwark M, Ernst S (1991) Removal of thiophene impurities from benzene by selective adsorption in zeolite ZSM-5. J Chem Soc Chem Commun 16:1133–1134
Dai C, Dong Y, Lei Z et al (2015) Separation of benzene and thiophene with a mixture of N-methyl-2-pyrrolidinone (NMP) and ionic liquid as the entrainer. Fluid Phase Equilib 388:142–150
Hanson C, Patel AN, Chang-Kakoti DK (1969) Separation of thiophene from benzene by solvent extraction. II. J Appl Chem 20:42–44
Shiriniana VZ, Zavarzina IV, Leonova ES et al (2015) Synthesis of new merocyanine dyes of thiophene series. Mendeleev Commun 25:262–263
Farid A, James SP (1980) The preparation of thiophenes. I. From C4-molecules and carbon disulphide. J Chem Technol Biotechnol 30(1):429–434
Atansa T, Francois F, Claude M (2000) Vapour-phase synthesis of thiophene from crotonaldehyde and carbon disulfide over promoted chromia on γ-alumina catalysts. Appl Catal A 192(1):71–79
Nardes AM, Kemerink M, Maturova K et al (2008) Conductivity, work function, and environmental stability of PEDOT: PSS thin films treated with sorbitol. Org Electron 9(5):727–734
Ju J, Yu J, Zhang X et al (2015) Isobaric vapor-liquid equilibrium of benzene-thiophene-dimethyl sulfoxide systems. J Chem Eng Chin Univ 29:724–730 (in Chinese)
Li X, Zhao L, Cheng T et al (2008) One force field for predicting multiple thermodynamic properties of liquid and vapor ethylene oxide. Fluid Phase Equilib 274(1):36–43
Cesar C, Edward JM (2006) Molecular simulation study of some thermophysical and transport properties of triazolium-based ionic liquids. J Phys Chem B 110(36):18026–18039
Neeraj R, Siepmann JI (2013) Transferable potentials for phase equilibria. 10. Explicit-hydrogen description of substituted benzenes and polycyclic aromatic compounds. J Phys Chem B 117(1):273–288
Panagiotopoulos AZ (1992) Direct determination of fluid phase equilibria by simulation in the Gibbs ensemble: a review. Mol Simul 9(1):1–23
Kofke DA (1993) Direct evaluation of phase coexistence by molecular simulation via integration along the saturation line. J Chem Phys 98(5):4149
Gergely K, István S, Martin W et al (2000) Extension of the NPT+ test particle method for the calculation of phase equilibria of nitrogen + ethane. J Mol Liq 85(1):237–247
Jorgensen WL, Madura JD, Swenson CJ (1984) Optimized intermolecular potential functions for liquid hydrocarbons. J Am Chem Soc 106(22):6638–6646
Contreras-Camacho RO, Ungerer P, Mackie AD et al (2004) Optimized intermolecular potential for aromatic hydrocarbons based on anisotropic united atoms. 1. Benzene. J Phys Chem B 108:14109–14114
Nath SK, Escobedo F, Fernando A et al (1998) On the simulation of vapor–liquid equilibria for alkanes. J Chem Phys 108(23):9905–9911
Martin MG (2006) Comparison of the AMBER, CHARMM, COMPASS, GROMOS, OPLS, TraPPE and UFF force fields for prediction of vapor–liquid coexistence curves and liquid densities. Fluid Phase Equilib 248(1):50–55
Martin MG, Siepmann JI (1999) Novel configurational-bias Monte Carlo method for branched molecules. Transferable potentials for phase equilibria. 2. United-atom description of branched alkanes. J Phys Chem B 103(21):4508–4517
Potoff JJ, Siepmann JI (2001) Vapor–liquid equilibria of mixtures containing alkanes, carbondioxide, and nitrogen. AIChE 47(7):1676–1682
Rai N, Siepmann JI (2007) Transferable potentials for phase equilibria. 9. Explicit hydrogen description of benzene and five-membered and six-membered heterocyclic aromatic compounds. J Phys Chem B 111(36):10790–10799
Chalaris M, Samios J (2000) Systematic molecular dynamics studies of liquid N, N-dimethylformamide using optimized rigid force fields: investigation of the thermodynamic, structural, transport and dynamic properties. J Chem Phys 112(19):8581–8594
Martin MG (2013) MCCCS Towhee: a tool for Monte Carlo molecular simulation. Mol Simul 39(14):1184–1194
Schnabe T, Vrabec J, Hasse H (2007) Unlike Lennard-Jones parameters for vapor–liquid equilibria. J Mol Liq 135(1):170–178
Green DW, Perry RH (2008) Perry’s chemical engineers’ handbook, 8th edn. McGraw-Hill Press, New York
Rowlinson JS, Widom B (1982) Molecular theory of capillarity. Oxford Press, Clarendon
Rowlinson JS, Swinton FL (1982) Liquids and liquid mixtures, 3rd edn. Butterworth Press, London
Gmehling J, Onken U, Arlt W (1980) Vapor–liquid equilibrium data collection. pt. 7. Aromatic hydrocarbons. DECHEMA Press, Chemistry Data Series, Frankfurt am Main, Germany
Seiji T, Tadafumi U, Masuhiro M (2002) Energy profile of the interconversion path between T-shape and slipped-parallel benzene dimers. J Chem Phys 117(42):11216–11221
Seiji T, Kazumasa H, Reiko A (2002) Model chemistry calculations of thiophene dimer interactions: origin of π-stacking. J Am Chem Soc 124(41):12200–12209
Blanco B, Beltrn S, Cabezas J (1997) Phase equilibria of binary systems formed by hydrocarbons from petroleum fractions and the solvents N-methylpyrrolidone and N, N-dimethylformamide. 1. Isobaric vapor–liquid equilibria. J Chem Eng Data 42(5):937–942
Bondi A (1964) Van der Waals volumes and radii. J Chem Phys 68(3):441–451
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Zeng, A., Chen, W., Ma, J. et al. Vapour–Liquid Equilibrium for N, N-Dimethylformamide + Benzene + Thiophene via Gibbs Ensemble Molecular Simulation. Trans. Tianjin Univ. 23, 26–34 (2017). https://doi.org/10.1007/s12209-016-0024-z
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12209-016-0024-z