Metrics for estimating vapour pressure deviation from ideality in binary mixtures

References

• A. Klamt, COSMO-RS from Quantum Chemistry to Fluid Phase Thermodynamics and Drug Design, Elsevier Science, Leverkusen, Germany, 2005.
   Google Scholar
• R. Wittig, J. Lohmann, and J. Gmehling, Vapor−liquid equilibria by UNIFAC group contribution. 6. Revision and extension, Ind. Eng. Chem. Res. 42 (2003), pp. 183–188. doi:10.1021/ie020506l.
   Web of Science ®Google Scholar
• P. Willett, J.M. Barnard, and G.M. Downs, Chemical similarity searching, J. Chem. Inf. Comput. Sci. 38 (1998), pp. 983–996. doi:10.1021/ci9800211.
   Google Scholar
• M.H. Abraham, Application of solvation equations to chemical and biochemical processes, Pure Appl. Chem. 65 (1993), pp. 2503–2512. doi:10.1351/pac199365122503.
   Web of Science ®Google Scholar
• A.M. Zissimos, M.H. Abraham, A. Klamt, F. Eckert, and J. Wood, A comparison between the two general sets of linear free energy descriptors of Abraham and Klamt, J. Chem. Inf. Comput. Sci. 42 (2002), pp. 1320–1331. doi:10.1021/ci025530o.
   PubMedGoogle Scholar
• T. Brown, QSPRs for predicting equilibrium partitioning in solvent–air systems from the chemical structures of solutes and solvents, J. Solution Chem. 51 (2022), pp. 1101–1132. doi:10.1007/s10953-022-01162-2.
   Web of Science ®Google Scholar
• K.U. Goss, Predicting the equilibrium partitioning of organic compounds using just one linear solvation energy relationship (LSER), Fluid Phase Equil. 233 (2005), pp. 19–22. doi:10.1016/j.fluid.2005.04.006.
   Web of Science ®Google Scholar
• S. Baskaran, Y.D. Lei, and F. Wania, Reliable prediction of the octanol–air partition ratio, Environ. Toxicol. Chem. 40 (2021), pp. 3166–3180. doi:10.1002/etc.5201.
   PubMed Web of Science ®Google Scholar
• T. Zhu, W. Chen, H. Cheng, Y. Wang, and R.P. Singh, Prediction of polydimethylsiloxane-water partition coefficients based on the pp-LFER and QSAR models, Ecotoxicol. Environ. Saf. 182 (2019), pp. 109374. doi:10.1016/j.ecoenv.2019.109374.
   PubMed Web of Science ®Google Scholar
• A. Klamt, Conductor-like screening model for real solvents: A new approach to the quantitative calculation of solvation phenomena, J. Phys. Chem. 99 (1995), pp. 2224–2235. doi:10.1021/j100007a062.
   Web of Science ®Google Scholar
• A. Klamt, V. Jonas, T. Bürger, and J.C.W. Lohrenz, Refinement and parametrization of COSMO-RS, J. Phys. Chem. A 102 (1998), pp. 5074–5085. doi:10.1021/jp980017s.
   Web of Science ®Google Scholar
• F. Eckert and A. Klamt, Fast solvent screening via quantum chemistry: COSMO-RS approach, AIChE J. 48 (2002), pp. 369–385. doi:10.1002/aic.690480220.
   Web of Science ®Google Scholar
• COSMOtherm, version C3.0, Release 19, Leverkusen, Germany, COSMOlogic GmbH & Co. KG, 2019.
   Google Scholar
• A. Klamt, F. Eckert, and M. Hornig, COSMO-RS: A novel view to physiological solvation and partition questions, J. Comput. Aided Mol. Des. 15 (2001), pp. 355–365. doi:10.1023/A:1011111506388.
   PubMed Web of Science ®Google Scholar
• A. Klamt and F. Eckert, COSMO-RS: A novel way from quantum chemistry to free energy, solubility, and general QSAR-descriptors for partitioning, in Rational Approaches to Drug Design, H.D. Höltje, W. and Sippl, eds., Prous Science, 2001, pp. 195–205.
   Google Scholar
• C. Mehler, A. Klamt, and W. Peukert, Use of COSMO-RS for the prediction of adsorption equilibria, AIChE J. 48 (2002), pp. 1093–1099. doi:10.1002/aic.690480518.
   Web of Science ®Google Scholar
• P. Gramatica, N. Chirico, E. Papa, S. Cassani, and S. Kovarich, QSARINS: A new software for the development, analysis, and validation of QSAR MLR models, J. Comput. Chem. 34 (2013), pp. 2121–2132. doi:10.1002/jcc.23361.
   Web of Science ®Google Scholar
• D.D. Deshpande and S.L. Oswal, 1. Excess Gibbs free energies and excess volumes, J. Chem. Thermodyn. 7 (1975), pp. 155–159. doi:10.1016/0021-9614(75)90263-3.
   Web of Science ®Google Scholar
• T. Boublík and G.C. Benson, Molar excess Gibbs free energies of benzene – m-xylene mixtures, Can. J. Chem. 47 (1969), pp. 539–542. doi:10.1139/v69-082.
   Web of Science ®Google Scholar
• A. Apelblat, A. Tamir, and M. Wagner, The binary mixtures of acetic acid with n-butanol, n-hexanol, n-octanol and n-dodecanol, Z. Phys. Chem. 137 (1983), pp. 129–137. doi:10.1524/zpch.1983.137.2.129.
   Google Scholar
• A.N. Campbell, E.M. Kartzmark, and J.M.T.M. Gieskes, Vapor–liquid equilibria, densities, and refractivities in the system acetic acid – chloroform – water at 25 °C, Can. J. Chem. 41 (1963), pp. 407–429. doi:10.1139/v63-059.
   Web of Science ®Google Scholar
• H. Arm, D. Bankay, K. Strub, and M. Waelti, Dampfdrücke, thermodynamische Mischungsfunktionen und Brechungsindices des binären systems Cyclohexan-Diäthyläther bei 25, Helv. Chim. Acta 50 (1967), pp. 1013–1016. doi:10.1002/hlca.19670500405.
   Web of Science ®Google Scholar
• K.L. Young, R.A. Mentzer, R.A. Greenkorn, and K.C. Chao, Vapor-liquid equilibrium in mixtures of cyclohexane + benzene, + octene-1, + m-xylene, and + n-heptane, J. Chem. Thermodyn. 9 (1977), pp. 979–985. doi:10.1016/0021-9614(77)90219-1.
   Web of Science ®Google Scholar
• D.V.S. Jain and O.P. Yadav, Vapour pressures and excess Gibbs energies of cyclohexane + o-xylene, + m-xylene, and + p-xylene, J. Chem. Thermodyn. 5 (1973), pp. 541–544. doi:10.1016/S0021-9614(73)80101-6.
   Web of Science ®Google Scholar
• V. Gupta, S. Maken, K.C. Kalra, and K.C. Singh, Molar excess Gibbs free energy of 1-propanol or 2-propanol + aromatic hydrocarbons at 298.15 K in terms of an association model with a Flory contribution term, Thermochim. Acta 277 (1996), pp. 187–198. doi:10.1016/0040-6031(95)02745-9.
   Web of Science ®Google Scholar
• K. Balslev and J. Abildskov, UNIFAC parameters for four new groups, Ind. Eng. Chem. Res. 41 (2002), pp. 2047–2057. doi:10.1021/ie010786p.
   Web of Science ®Google Scholar
• P. Rice and A. El-Nikheli, Isothermal vapour-liquid equilibrium data for the systems n-pentane with n-hexane, n-octane and n-decane, Fluid Phase Equil. 107 (1995), pp. 257–267. doi:10.1016/0378-3812(95)02679-9.
   Web of Science ®Google Scholar
• J.S. Choi and Y.C. Bae, Renormalization group corrections to the modified perturbed hard sphere chain equation of state for vapor liquid equilibria and interfacial tension of pure and binary mixtures, Fluid Phase Equil. 430 (2016), pp. 143–155. doi:10.1016/j.fluid.2016.09.029.
   Web of Science ®Google Scholar
• American Chemical Society, Isothermal vapor-liquid equilibrium data by total pressure method. systems acetaldehyde-ethanol, acetaldehyde-water, and ethanol-water. Available at https://pubs.acs.org/doi/pdf/10.1021/je60046a010.
   Google Scholar
• H. Guerrero, I. Giner, H. Artigas, C. Lafuente, and I. Gascón, Isothermal vapor−liquid equilibrium of ternary mixtures containing 2-methyl-1-propanol or 2-methyl-2-propanol, n-hexane, and 1-chlorobutane at 298.15 K, J. Chem. Eng. Data 55 (2010), pp. 739–744. doi:10.1021/je900436f.
   Web of Science ®Google Scholar
• E. Hála, I. Wichterle, J. Polák, and T. Boublik, Vapour-Liquid Equilibrium Data at Normal Pressures, Pergamon Press Ltd., Institute of Chemical Process Fundamentals, Prague, Czechoslovakia, 1968.
   Google Scholar
• E.H.J. Cunaeus, Die Bestimmung des Brechungsvermögens als Methode zur Untersuchung der Zusammensetzung koexistierender Dampf- und Flüssigkeitsphasen, Z. Phys. Chem. 36 (1901), pp. 232–238. doi:10.1515/zpch-1901-3616.
   Google Scholar
• J. Sameshima, On the system acetone—ethyl ether. J. Am. Chem. Soc. 40 (1918), pp. 1482–1503. doi:10.1021/ja02243a002.
   Google Scholar
• J. Nagai, and N. Ishii. Parts II-IV, J. Soc. Chem. Ind. Jap. 38 (1935), pp. 86–25271068.
   Google Scholar
• N. Ishii, Studies on volatility of fuels containing ethyl alcohol V-VI, J. Soc. Chem. Ind. Jap. 38 (1935), pp. 659–25271068.
   Google Scholar
• K.S. Yuan, B.C.-Y. Lu, A.K. Deshpande, and J.K.C. Ho, Part III. system ethanol - cyclohexane at atmospheric pressure, J. Chem. Eng. Data 8 (1963), pp. 549–559. doi:10.1021/je60019a024.
   Google Scholar
• G.C. Schmidt and G. Binäre, Binäre Gemische, Z. Phys. Chem. 121 (1926), pp. 221–253. doi:10.1515/zpch-1926-12119.
   Google Scholar
• G. Guglielmoq, Sulle Tensioni Parziali e le Pressioni Osmotiche delle Miscele di Liquidi Volatili, Rendiconti/Acad. Naz. Lincei Cl. Sci. Fis. Mat. Natur. 1 (1892), pp. 294–298.
   Google Scholar
• F. Becker, M. Kiefer, P. Rhensius, and H.D. Schaefer, Interpretation von Dampfdruckdiagrammen binärer flüssiger Mischungen mit Hilfe von Gleichgewichtsmodellen, Z. Phys. Chem. 92 (1974), pp. 169–192. doi:10.1524/zpch.1974.92.4-6.169.
   Google Scholar
• V. Antón, S. Martín, C. Lafuente, and I. Gascón, Experimental and predicted vapour–liquid equilibrium of the binary mixtures n-heptane + chlorobutane isomers, Fluid Phase Equil. 409 (2016), pp. 72–77. doi:10.1016/j.fluid.2015.09.031.
   Web of Science ®Google Scholar
• M. Góral, P. Oracz, A. Skrzecz, A. Bok, and A. Mączyński, Recommended vapor–liquid equilibrium data. Part 1: Binary n-Alkanol–n-Alkane systems, J. Phys. Chem. Ref. Data 31 (2002), pp. 701–748. doi:10.1063/1.1480097.
   Web of Science ®Google Scholar
• PHYSPROP Physical Properties Database, SRC Inc (www.srcinc.com).
   Google Scholar
• US EPA. Estimation Programs Interface Suite^TM For Microsoft® Windows, V 4.11, United States Environmental Protection Agency, Washington, DC, USA, 2022.
   Google Scholar
• K. Mansouri, C.M. Grulke, R.S. Judson, and A.J. Williams, OPERA models for predicting physicochemical properties and environmental fate endpoints, J. Cheminform. 10 (2018), pp. 10. doi:10.1186/s13321-018-0263-1.
   PubMed Web of Science ®Google Scholar
• T.N. Brown, Empirical regressions between system parameters and solute descriptors of polyparameter linear free energy relationships (PPLFERs) for predicting solvent-air partitioning, Fluid Phase Equil. 540 (2021), pp. 113035. doi:10.1016/j.fluid.2021.113035.
   Web of Science ®Google Scholar
• P. Gramatica, E. Papa, and A. Sangion, QSAR modeling of cumulative environmental end-points for the prioritization of hazardous chemicals, Environ. Sci. 20 (2018), pp. 38–47. doi:10.1039/C7EM00519A.
   Google Scholar
• P. Gramatica, Principles of QSAR modeling: Comments and suggestions from personal experience, IJQSPR 5 (2020), pp. 61–97. doi:10.4018/IJQSPR.20200701.oa1.
   Google Scholar
• A. Klamt and F. Eckert, Prediction of vapor liquid equilibria using COSMOtherm, Fluid Phase Equil. 217 (2004), pp. 53–57. doi:10.1016/j.fluid.2003.08.018.
   Web of Science ®Google Scholar
• M. Hu, H. Tian, J. Sun, R. Zhang, Q. Zhao, and W. Xu, Vapor–liquid equilibrium measurements of cyclohexene–isophorone and cyclohexanol–isophorone binary systems and predictions for cyclohexene–cyclohexanol–isophorone ternary system, J. Chem. Eng. Data 65 (2020), pp. 3103–3108. doi:10.1021/acs.jced.0c00103.
   Web of Science ®Google Scholar
• Y. Li, X. Chen, L. Wang, X. Wei, W. Nong, and X. Wei, J. Liang, Measurement and prediction of isothermal vapor–liquid equilibrium of α-pinene + camphene/longifolene + abietic acid + palustric acid + neoabietic acid systems, Chin. J. Chem. Engin. 53 (2023), pp. 155–169. doi:10.1016/j.cjche.2021.12.030.
   Web of Science ®Google Scholar
• F. Eckert and A. Klamt, Validation of the COSMO-RS method: Six binary systems, Ind. Eng. Chem. Res. 40 (2001), pp. 2371–2378. doi:10.1021/ie0009132.
   Web of Science ®Google Scholar