chemicallytechFine Chemical TechnologiesТонкие химические технологии2410-65932686-7575MIREA – Russian Technological University (RTU MIREA).10.32362/2410-6593-2024-19-4-279-292WXQZSMchemicallytech-2119Research ArticleTHEORETICAL BASIS OF CHEMICAL TECHNOLOGYТЕОРЕТИЧЕСКИЕ ОСНОВЫ ХИМИЧЕСКОЙ ТЕХНОЛОГИИComparison of methods for calculating the enthalpy of vaporization of binary azeotropic mixturesСравнение методов расчета энтальпии парообразования бинарных азеотропных смесейhttps://orcid.org/0000-0001-6415-8059РыжкинД. А.RyzhkinD. A.

Рыжкин Дмитрий Антонович - аспирант кафедры химии и технологии основного органического синтеза, Институт тонких химических технологий им. М.В. Ломоносова. Scopus Author ID 57223230408, ResearcherID AAU-6583-2021.

119571, Москва, пр-т Вернадского, д. 86

Dmitry А. Ryzhkin - Postgraduate Student, Department of Chemistry and Technology of Basic Organic Synthesis, M.V. Lomonosov Institute of Fine Chemical Technologies. Scopus Author ID 57223230408, ResearcherID AAU-6583-2021.

86, Vernadskogo pr., Moscow, 119571

dima-ryzhkin@mail.ruhttps://orcid.org/0000-0002-5664-4409РаеваВ. М.RaevaV. M.

Раева Валентина Михайловна - к.т.н., доцент кафедры химии и технологии основного органического синтеза, Институт тонких химических технологий им. М.В. Ломоносова. Scopus Author ID 6602836975, ResearcherID C-8812-2014.

119571, Москва, пр-т Вернадского, д. 86

Valentina М. Raeva - Cand. Sci. (Eng.), Associate Professor, Department of Chemistry and Technology of Basic Organic Synthesis, Scopus Author ID 6602836975, ResearcherID C-8812-2014.

86, Vernadskogo pr., Moscow, 119571

raevalentina1@gmail.comМИРЭА — Российский технологический университет (Институт тонких химических технологий им. М.В. Ломоносова)РоссияMIREA — Russian Technological University (M.V. Lomonosov Institute of Fine Chemical Technologies)Russian Federation202411092024194279292Copyright © Ryzhkin D.A., Raeva V.M., 20242024Рыжкин Д.А., Раева В.М.Ryzhkin D.A., Raeva V.M.Данная работа распространяется под лицензией Creative Commons Attribution 4.0.This work is licensed under a Creative Commons Attribution 4.0 License.https://www.finechem-mirea.ru/jour/article/view/2119Objectives

Objectives. To calculate the molar enthalpy of vaporization of binary homogeneous mixtures based on isothermal and isobaric vapor–liquid equilibrium data, and to compare the results of calculation of molar enthalpy of vaporization by different methods with experimental data.

Methods

Methods. Simulation of the vapor–liquid equilibrium of binary systems according to the Non-Random Two Liquid “local compositions” equation and thermodynamic calculations of molar vaporization enthalpies of binary mixtures at different conditions of vapor–liquid equilibrium were used.

Results

Results. Arrays of calculated data were obtained with regard to molar enthalpies of vaporization for 25 compositions of binary azeotropes (isothermal, isobaric conditions of phase equilibrium), and the full range of compositions of the benzene–ethanol system at atmospheric pressure.

Conclusions

Conclusions. The accuracy of thermodynamic methods for calculating the vaporization enthalpy of binary azeotropic mixtures according to vapor–liquid equilibrium data is higher in 85% of cases for isothermal, and in 75% of cases for isobaric conditions. By taking into account the influence of temperature on the activity coefficients of components in the liquid phase, the values of excess molar enthalpy both for azeotrope compositions and for the full concentration range of the benzene–ethanol system under isobaric conditions of liquid–vapor phase equilibrium can be accurately reproduced.

Цели

Цели. Расчет молярных энтальпий парообразования бинарных гомогенных смесей по изотермическим и изобарическим данным парожидкостного равновесия; сравнение результатов расчета молярных энтальпий парообразования по разным методам с экспериментальными данными.

Методы

Методы. Моделирование парожидкостного равновесия бинарных систем по уравнению «локальных составов» NRTL (Non-Random Two Liquid); термодинамические расчеты молярных энтальпий парообразования смесей в разных условиях парожидкостного равновесия.

Результаты

Результаты. Получены массивы расчетных данных по молярным энтальпиям парообразования для 25 составов бинарных азеотропов (изотермические, изобарические условия фазового равновесия) и полного диапазона составов системы бензол–этанол при атмосферном давлении.

Выводы

Выводы. Точность термодинамических методов расчета энтальпий парообразования бинарных азеотропных смесей по данным парожидкостного равновесия выше в 85% случаев для изотермических и в 75% случаев для изобарических условий. Учет влияния температуры на коэффициенты активности компонентов в жидкой фазе позволяет качественно верно воспроизводить значения избыточной молярной энтальпии как для составов азеотропов, так и для полного концентрационного диапазона системы бензол–этанол в изобарических условиях фазового равновесия жидкость–пар.

молярная энтальпия парообразованиябинарные азеотропыпарожидкостное равновесиеmolar enthalpy of vaporizationbinary azeotropesvapor–liquid equilibriumРабота выполнена при финансовой поддержке гранта государственного задания № FSFZ-2023-0003The work was financially supported by the grant of the State Assignment No. FSFZ-2023-0003ReferencesКарапетьянц М.Х. Химическая термодинамика. М.: Химия; 1975. 583 с.Karapet’yants M.Kh. Khimicheskaya termodinamika (Chemical Thermodynamics). Мoscow: Khimiya; 1975. 583 p. (in Russ.)Black C. Importance of thermophysical data in process simulation. Int. J. Thermophys. 1986;7(4):987–1002. https://doi.org/10.1007/BF00503853Black C. Importance of thermophysical data in process simulation. Int. J. Thermophys. 1986;7(4):987–1002. https://doi.org/10.1007/BF00503853Sandler S.I. Thermophysical properties: What have we learned recently, and what do we still need to know? Int. J. Thermophys. 1994;15(6):1013–1035. https://doi.org/10.1007/BF01458812Sandler S.I. Thermophysical properties: What have we learned recently, and what do we still need to know? Int. J. Thermophys. 1994;15(6):1013–1035. https://doi.org/10.1007/BF01458812Oscarson J.L., Rowley R.L., Wilding W.V., Izatt R.M. Industrial need for accurate thermophysical data and for reliable prediction methods. J. Therm. Anal. Calorim. 2008;92(2): 465–470. https://doi.org/10.1007/s10973-007-8972-0Oscarson J.L., Rowley R.L., Wilding W.V., Izatt R.M. Industrial need for accurate thermophysical data and for reliable prediction methods. J. Therm. Anal. Calorim. 2008;92(2): 465–470. https://doi.org/10.1007/s10973-007-8972-0Solomonov B.N., Varfolomeev M.A., Nagrimanov R.N., Novikov V.B., Zaitsau D.H., Verevkin S.P. Solution calorimetry as a complementary tool for the determination of enthalpies of vaporization and sublimation of low volatile compounds at 298.15 K. Thermochimica Acta. 2014;589:164–173. https://doi.org/10.1016/j.tca.2014.05.033Solomonov B.N., Varfolomeev M.A., Nagrimanov R.N., Novikov V.B., Zaitsau D.H., Verevkin S.P. Solution calorimetry as a complementary tool for the determination of enthalpies of vaporization and sublimation of low volatile compounds at 298.15 K. Thermochimica Acta. 2014;589:164–173. https://doi.org/10.1016/j.tca.2014.05.033Yu D., Chen Z. A theoretical analysis on enthalpy of vaporization: Temperature dependence and singularity at the critical state. Fluid Phase Equil. 2020;516:112611. https://doi.org/10.1016/j.fluid.2020.112611Yu D., Chen Z. A theoretical analysis on enthalpy of vaporization: Temperature dependence and singularity at the critical state. Fluid Phase Equil. 2020;516:112611. https://doi.org/10.1016/j.fluid.2020.112611Solomonov B.N., Yagofarov M.I. Compensation relationship in thermodynamics of solvation and vaporization: Features and applications. II. Hydrogen-bonded systems. J. Mol. Liq. 2023;372(2):121205. https://doi.org/10.1016/j.molliq.2023.121205Solomonov B.N., Yagofarov M.I. Compensation relationship in thermodynamics of solvation and vaporization: Features and applications. II. Hydrogen-bonded systems. J. Mol. Liq. 2023;372(2):121205. https://doi.org/10.1016/j.molliq.2023.121205Tyrer D. CLXXXVI. Latent heats of vaporization of mixed liquids. Part I. J. Chem. Soc., Trans. 1911;99:1633–1645. https://doi.org/10.1039/CT9119901633Tyrer D. CLXXXVI. Latent heats of vaporization of mixed liquids. Part I. J. Chem. Soc., Trans. 1911;99:1633–1645. https://doi.org/10.1039/CT9119901633Shivabasappа K.L., Nirguna Babu P., Jagannadha Rao Y. Enthalpy of mixing and heat of vaporization of ethyl acetate with benzene and toluene at 298.15 K and 308.15 K. Braz. J. Chem. Eng. 2008;25(1):167–174. https://doi.org/10.1590/s0104-66322008000100017Shivabasappа K.L., Nirguna Babu P., Jagannadha Rao Y. Enthalpy of mixing and heat of vaporization of ethyl acetate with benzene and toluene at 298.15 K and 308.15 K. Braz. J. Chem. Eng. 2008;25(1):167–174. https://doi.org/10.1590/s0104-66322008000100017Захаров М.К., Егоров А.В., Подметенный А.А. Разделение жидких смесей и затраты теплоты при ректификации. Тонкие химические технологии. 2021;16(1):7–15. https://doi.org/10.32362/2410-6593-2021-16-1-7-15Zakharov M.K., Egorov A.V., Podmetenny A.A. Liquid mixtures separation and heat consumption in the process of distillation. Tonk. Khim. Tekhnol. = Fine Chem. Technol. 2021;16(1):7–15 (Russ., Eng.). https://doi.org/10.32362/24106593-2021-16-1-7-15Pashchenko L.L., Druzhinina A.I. Enthalpy of vaporization measurements by calorimetric techniques. J. Therm. Anal. Calorim. 2018;133(2):1173–1179. https://doi.org/10.1007/s10973-018-7370-0Pashchenko L.L., Druzhinina A.I. Enthalpy of vaporization measurements by calorimetric techniques. J. Therm. Anal. Calorim. 2018;133(2):1173–1179. https://doi.org/10.1007/s10973-018-7370-0Vicencio L.A., López-Porfiri P., de la Fuente J.C. Vapour pressure and vaporisation enthalpy for two key apple odorants, ethyl butyrate and ethyl hexanoate, at pressures from (15 to 105) kPa. J. Chem. Тhermodyn. 2020;142:105982. https://doi.org/10.1016/j.jct.2019.105982Vicencio L.A., López-Porfiri P., de la Fuente J.C. Vapour pressure and vaporisation enthalpy for two key apple odorants, ethyl butyrate and ethyl hexanoate, at pressures from (15 to 105) kPa. J. Chem. Тhermodyn. 2020;142:105982. https://doi.org/10.1016/j.jct.2019.105982Abdullah R.S., Solomonov B.N.. Sublimation/vaporization and solvation enthalpies of monosubstituted pyridine derivatives. Chem. Thermodyn. Therm. Anal. 2022;8(20):100087. https://doi.org/10.1016/j.ctta.2022.100087Abdullah R.S., Solomonov B.N.. Sublimation/vaporization and solvation enthalpies of monosubstituted pyridine derivatives. Chem. Thermodyn. Therm. Anal. 2022;8(20):100087. https://doi.org/10.1016/j.ctta.2022.100087Dong J.-Q., Lin R.-S., Yen W.-H. Heats of vaporization and gaseous molar heat capacities of ethanol and the binary mixture of ethanol and benzene. Can. J. Chem. 1988;66(4):783–790. https://doi.org/10.1139/v88-136Dong J.-Q., Lin R.-S., Yen W.-H. Heats of vaporization and gaseous molar heat capacities of ethanol and the binary mixture of ethanol and benzene. Can. J. Chem. 1988;66(4):783–790. https://doi.org/10.1139/v88-136Tamir A. Prediction of latent heat of vaporization of multicomponent mixtures. Fluid Phase Equil. 1982;8(2): 131–147. https://doi.org/10.1016/0378-3812(82)80031-9Tamir A. Prediction of latent heat of vaporization of multicomponent mixtures. Fluid Phase Equil. 1982;8(2): 131–147. https://doi.org/10.1016/0378-3812(82)80031-9Ito T., Yamaguchi T., Akasaka R. Heat of vaporization of mixtures. Heat Transfer Japanese Res. 1996;25(1):12–24. https://doi.org/10.1002/(SICI)1520-6556(1996)25:1%3C12::AIDHTJ2%3E3.0.CO;2-1Ito T.,YamaguchiT.,Akasaka R. Heat of vaporization of mixtures. Heat Transfer Japanese Res. 1996;25(1):12–24. https://doi.org/10.1002/(SICI)1520-6556(1996)25:1%3C12::AIDHTJ2%3E3.0.CO;2-1Marchelli G., Ingenmey J., Hollóczki O., Chaumont A., Kirchner B. Hydrogen-bonding and vaporization thermodynamics in hexafluoroisopropanol-acetone and -methanol mixtures. A Joined cluster analysis and molecular dynamic study. ChemPhysChem. 2022;23(1):e202100620. https://doi.org/10.1002/cphc.202100620Marchelli G., Ingenmey J., Hollóczki O., Chaumont A., Kirchner B. Hydrogen-bonding and vaporization thermodynamics in hexafluoroisopropanol-acetone and -methanol mixtures. A Joined cluster analysis and molecular dynamic study. ChemPhysChem. 2022;23(1):e202100620. https://doi.org/10.1002/cphc.202100620Swietoslawski W., Zielenkiewicz A. Vaporization enthalpy of the homologous series of binary azeotropes. Rocz. Chem. 1958;32:913–922.Swietoslawski W., Zielenkiewicz A. Vaporization enthalpy of the homologous series of binary azeotropes. Rocz. Chem. 1958;32:913–922.Tamir A. Compilation and correlation of binary azeotropic data. Fluid Phase Equil. 1981;5(3–4):199–206. https://doi.org/10.1016/0378-3812(80)80057-4Tamir A. Compilation and correlation of binary azeotropic data. Fluid Phase Equil. 1981;5(3–4):199–206. https://doi.org/10.1016/0378-3812(80)80057-4Жерин И.И. Фториды галогенов в технологии ядерного топлива. Термодинамика фазовых равновесий в системах, содержащих UF6, BrF3, IF5 и HF. Изв. Томского политехн. ун-та. 2003;306(6):8–11.Zherin I.I. Halogen fluorides in nuclear fuel technology. Thermodynamics of phase equilibria in systems containing UF6, BrF3, IF5, and HF. Izvestiya Tomskogo Politekhnicheskogo Univesiteta = Bulletin of the Tomsk Polytechnic University. 2003;306(6):8–11 (in Russ.).Neilson E.F., White D. The heat of vaporization and solution of a binary mixture of fluorocarbons. J. Phys. Chem. 1959;63(9):1363–1365. https://doi.org/10.1021/j150579a005Neilson E.F., White D. The heat of vaporization and solution of a binary mixture of fluorocarbons. J. Phys. Chem. 1959;63(9):1363–1365. https://doi.org/10.1021/j150579a005Pandey J.D., Srivastava T., Chandra P., Prashant R., Dwivedi P.K. Estimation of cohesive forces, energy of vaporization, heat of vaporization, cohesive energy density, solubility parameter and Van der Waals constant of binary liquid mixtures using generalized hole theory. Indian J. Chem. 2007;46A:1605–1610.Pandey J.D., Srivastava T., Chandra P., Prashant R., Dwivedi P.K. Estimation of cohesive forces, energy of vaporization, heat of vaporization, cohesive energy density, solubility parameter and Van der Waals constant of binary liquid mixtures using generalized hole theory. Indian J. Chem. 2007;46A:1605–1610.Bedretdinov F., Tsvetov N., Raeva V., Chelyuskina T. Research of the properties of binary biazeotropic mixtures. In: Proc. of the 46th International Conference of the Slovak Society of Chemical Engineering. Tatranské Matliare, High Tatras, Slovakia May 20–23, 2019. Bratislava; 2019. P. 171.Bedretdinov F., Tsvetov N., Raeva V., Chelyuskina T. Research of the properties of binary biazeotropic mixtures. In: Proc. of the 46th International Conference of the Slovak Society of Chemical Engineering. Tatranské Matliare, High Tatras, Slovakia May 20–23, 2019. Bratislava; 2019. P. 171.Раева В.М. Теплоты испарения бинарных смесей. Тонкие химические технологии. 2013;8(1):43–50.Raeva V.M. Vaporization heat of binary mixtures. Tonk. Khim. Tekhnol. = Fine Chem. Technol. 2013;8(1):43–50 (in Russ.).Lenoir J.M., Hipkin H.G. Measured enthalpies of eight hydrocarbon fractions. J. Chem. Eng. Data. 1973;18(2): 195–202. https://doi.org/10.1021/je60057a026Lenoir J.M., Hipkin H.G. Measured enthalpies of eight hydrocarbon fractions. J. Chem. Eng. Data. 1973;18(2): 195–202. https://doi.org/10.1021/je60057a026Grigoriev B., Alexandrov I., Gerasimov A. Application of multiparameter fundamental equations of state to predict the thermodynamic properties and phase equilibria of technological oil fractions. Fuel. 2018;215:80–89. https://doi.org/10.1016/j.fuel.2017.11.022Grigoriev B., Alexandrov I., Gerasimov A. Application of multiparameter fundamental equations of state to predict the thermodynamic properties and phase equilibria of technological oil fractions. Fuel. 2018;215:80–89. https://doi.org/10.1016/j.fuel.2017.11.022Tatar A., Barati-Harooni A., Partovi M., Najafi-Marghmaleki A., et al. An accurate model for predictions of vaporization enthalpies of hydrocarbons and petroleum fractions. J. Mol. Liq. 2016;220:192–199. https://doi.org/10.1016/j.molliq.2016.04.069Tatar A., Barati-Harooni A., Partovi M., NajafiMarghmaleki A., et al. An accurate model for predictions of vaporization enthalpies of hydrocarbons and petroleum fractions. J. Mol. Liq. 2016;220:192–199. https://doi.org/10.1016/j.molliq.2016.04.069Balabin R.M., Syunyaev R.Z., Karpov S.A.. Molar enthalpy of vaporization of ethanol–gasoline mixtures and their colloid state. Fuel. 2007;86(3):323–327. https://doi.org/10.1016/j.fuel.2006.08.008Balabin R.M., Syunyaev R.Z., Karpov S.A.. Molar enthalpy of vaporization of ethanol–gasoline mixtures and their colloid state. Fuel. 2007;86(3):323–327. https://doi.org/10.1016/j.fuel.2006.08.008Gautam A., Kumar A.A.. Determination of important biodiesel properties based on fuel temperature correlations for application in a locomotive engine. Fuel. 2015;142:289–302. https://doi.org/10.1016/j.fuel.2014.10.032Gautam A., Kumar A.A.. Determination of important biodiesel properties based on fuel temperature correlations for application in a locomotive engine. Fuel. 2015;142:289–302. https://doi.org/10.1016/j.fuel.2014.10.032Abernathy S.M., Brown K.R. Predicting the enthalpy of vaporization and calculating the entropy of vaporization of 87 octane gasoline using vapor pressure. Open Access Library Journal (OALib. Journal). 2016;3(e2954):1–11. http://doi.org/10.4236/oalib.1102954Abernathy S.M., Brown K.R. Predicting the enthalpy of vaporization and calculating the entropy of vaporization of 87 octane gasoline using vapor pressure. Open Access Library Journal (OALib. Journal). 2016;3(e2954):1–11. http://doi.org/10.4236/oalib.1102954Akasaka R., Yamaguchi T., Ito T. Practical and direct expressions of the heat of vaporization for mixtures. Chem. Eng. Science. 2005;60(16):4369–4376. https://doi.org/10.1016/j.ces.2005.03.005Akasaka R., Yamaguchi T., Ito T. Practical and direct expressions of the heat of vaporization for mixtures. Chem. Eng. Science. 2005;60(16):4369–4376. https://doi.org/10.1016/j.ces.2005.03.005Benkouider A.M., Kessas R., Guella S., Yahiaoui A., Bagui F. Estimation of the enthalpy of vaporization of organic components as a function of temperature using a new group contribution method. J. Mol. Liq. 2014;194:48–56. https://doi.org/10.1016/j.molliq.2014.01.006Benkouider A.M., Kessas R., Guella S., Yahiaoui A., Bagui F. Estimation of the enthalpy of vaporization of organic components as a function of temperature using a new group contribution method. J. Mol. Liq. 2014;194:48–56. https://doi.org/10.1016/j.molliq.2014.01.006Bolmatenkov D.N., Yagofarov M.I., Notfullin A.A., Solomonov B.N. Calculation of the vaporization enthalpies of alkylaromatic hydrocarbons as a function of temperature from their molecular structure. Fluid Phase Equil. 2022;554:113303. https://doi.org/10.1016/j.fluid.2021.113303Bolmatenkov D.N., Yagofarov M.I., Notfullin A.A., Solomonov B.N. Calculation of the vaporization enthalpies of alkylaromatic hydrocarbons as a function of temperature from their molecular structure. Fluid Phase Equil. 2022;554:113303. https://doi.org/10.1016/j.fluid.2021.113303Bolmatenkov D.N.,Yagofarov M.I., Valiakhmetov T.F., Rodionov N.O., Solomonov B.N. Vaporization enthalpies of benzanthrone, 1-nitropyrene, and 4-methoxy-1-naphthonitrile: Prediction and experiment. J. Chem. Thermodyn. 2022;168:106744. https://doi.org/10.1016/j.jct.2022.106744Bolmatenkov D.N.,Yagofarov M.I., Valiakhmetov T.F., Rodionov N.O., Solomonov B.N. Vaporization enthalpies of benzanthrone, 1-nitropyrene, and 4-methoxy-1naphthonitrile: Prediction and experiment. J. Chem. Thermodyn. 2022;168:106744. https://doi.org/10.1016/j.jct.2022.106744Bolmatenkov D.N., Yagofarov M.I., Sokolov A.A., Solomonov B.N. Vaporization enthalpies of self-associated aromatic compounds at 298.15 K: A review of existing data and the features of heat capacity correction. Part I. Phenols. Thermochimica Acta. 2023;721:179455. https://doi.org/10.1016/j.tca.2023.179455Bolmatenkov D.N., Yagofarov M.I., Sokolov A.A., Solomonov B.N. Vaporization enthalpies of self-associated aromatic compounds at 298.15 K: A review of existing data and the features of heat capacity correction. Part I. Phenols. Thermochimica Acta. 2023;721:179455. https://doi.org/10.1016/j.tca.2023.179455Арутюнов Б.А., Мохаммед Ю.А. Термодинамический метод расчета теплоты парообразования бинарных смесей. Тонкие химические технологии. 2010;5(5):36–39.Arutionov B.A., Elsadig Y.A. Thermodynamic method of calculation of heat of steam formation for binary mixes. Tonk. Khim. Tekhnol. = Fine Chem. Technol. 2010;5(5):36–39 (in Russ.).Арутюнов Б.А., Мохаммед Ю.А., Аушева Е.В. Температурная зависимость теплоты парообразования чистых углеводородов и их бинарных смесей. Тонкие химические технологии. 2010;5(5):40–42.Arutionov B.A., Elsadig Y.A., Ausheva E.V. Temperature dependence of heat of vaporization of pure hydrocarbons and their binary mixtures. Tonk. Khim. Tekhnol. = Fine Chem. Technol. 2010;5(5):40–42 (in Russ.).Арутюнов Б.А., Рытова Е.В., Раева В.М., Фролкова А.К. Методы расчета теплот парообразования углеводородов и их смесей в широком диапазоне температур. Теор. основы хим. технологии. 2017;51(5):595–604. https://doi.org/10.7868/S0040357117050025Arutyunov B.A., Rytova E.V., Raeva V.M., et. al. Methods for calculating the evaporation heats of hydrocarbons and their mixtures in a wide temperature range. Theor. Found. Chem. Eng. 2017;51(5):742–751. https://doi.org/10.1134/s0040579517050268 [Original Russian Text: Arutyunov B.A., Rytova E.V., Raeva V.M., Frolkova A.K. Methods for calculating the heat of vaporization of hydrocarbons and their mixtures in a wide temperature range. Teoreticheskie Osnovy Khimicheskoi Tekhnologii. 2017;51(5):595–604 (in Russ.). https://doi.org/10.7868/S0040357117050025 ]Tamir A., Dragoescu C., Apelblat A., Wisniak J. Heats of vaporization and vapor–liquid equilibria in associated solutions containing formic acid, acetic acid, propionic acid and carbon tetrachloride. Fluid Phase Equil. 1983;10(1):9–42. https://doi.org/10.1016/0378-3812(83)80002-8Tamir A., Dragoescu C., Apelblat A., Wisniak J. Heats of vaporization and vapor–liquid equilibria in associated solutions containing formic acid, acetic acid, propionic acid and carbon tetrachloride. Fluid Phase Equil. 1983;10(1):9–42. https://doi.org/10.1016/0378-3812(83)80002-8Solomonov B.N., Yagofarov M.I., Nagrimanov R.N. Additivity of vaporization enthalpy: Group and molecular contributions exemplified by alkylaromatic compounds and their derivatives. J. Mol. Liq. 2021;342:117472. https://doi.org/10.1016/j.molliq.2021.117472Solomonov B.N., Yagofarov M.I., Nagrimanov R.N. Additivity of vaporization enthalpy: Group and molecular contributions exemplified by alkylaromatic compounds and their derivatives. J. Mol. Liq. 2021;342:117472. https://doi.org/10.1016/j.molliq.2021.117472Solomonov B.N., Yagofarov M.I. Compensation relationship in thermodynamics of solvation and vaporization: Features and applications. II. Hydrogen-bonded systems. J. Mol. Liq. 2023;372:121205. https://doi.org/10.1016/j.molliq.2023.121205Solomonov B.N., Yagofarov M.I. Compensation relationship in thermodynamics of solvation and vaporization: Features and applications. II. Hydrogen-bonded systems. J. Mol. Liq. 2023;372:121205. https://doi.org/10.1016/j.molliq.2023.121205Морачевский А.Г., Смирнова Н.А., Алексеева М.В., Балашова И.М., Викторов А.И., Куранов Г.Л., Пиотровская Е.М., Пукинский И.Б. Термодинамика равновесия жидкость-пар. Л.: Химия; 1989. 344 с.Morachevskii A.G., Smirnova N.A., Alekseeva M.V., Balashova I.M., Viktorov A.I., Kuranov G.L., Piotrovskaya E.M., Pukinskii I.B. Termodinamika ravnovesiya zhidkost’–par (Thermodynamics of Liquid–Vapor Equilibrium). Leningrad: Khimiya; 1989. 344 p. (in Russ.).Рид Р., Праусниц Дж., Шервуд Т. Свойства газов и жидкостей; пер. с англ. Л.: Химия; 1982. 592 с.Reid R.C., Prausnitz J.M., Sherwood T.K. Svoistva gazov i zhidkostei (The Properties of Gases and Liquids); transl. from Engl. Leningrad: Khimiya; 1982. 592 p. (in Russ.). [Reid R.C., Prausnitz J.M., Sherwood T.K. The Properties of Gases and Liquids. NY: McGraw-Hill; 1977. 710 p.]Уэйлес С. Фазовые равновесия в химической технологии: в 2-х ч.; пер. с англ. М.: Мир; 1989. Ч. 1. 304 c.Walas S.M. Fazovye ravnovesiya v khimicheskoi tekhnologii (Phase Equilibria in Chemical Engineering): in 2 v.; transl. from Engl. Мoscow: Mir; 1989. V. 1. 304 p. (in Russ.). [Walas S.M. Phase Equilibria in Chemical Engineering. Oxford: Butterworth-Heinemann Publ., 1985. 671 p.]Раева В.М., Анисимов А.В., Рыжкин Д.А.. Расчет энтальпий парообразования системы бензол–циклогексан. Изв. АН. Сер. хим. 2021;(4):715–721. https://doi.org/10.1007/s11172-021-3141-3Raeva V.M., Anisimov A.V., Ryzhkin D.A. Calculation of vaporization enthalpies of a benzene–cyclohexane system. Russ. Chem. Bull. 2021;70(4):715–721. https://doi.org/10.1007/s11172-021-3141-3 [Original Russian Text: Raeva V.M., Anisimov A.V., Ryzhkin D.A. Calculation of vaporization enthalpies of a benzene–cyclohexane system. Izvestiya Akademii Nauk. Seriya Khimicheskaya.2021;(4):715–721 (in Russ.).]Ryzhkin D.A., Raeva V.M. Calculation of vaporization enthalpies of methanol–tetrahydrofuran–acetonitrile at atmospheric pressure. In: Proc. of the 23rd International Conference on Chemical Thermodynamics in Russia. Russia, Kazan, August 22–27, 2022. P. 298.Ryzhkin D.A., Raeva V.M. Calculation of vaporization enthalpies of methanol–tetrahydrofuran–acetonitrile at atmospheric pressure. In: Proc. of the 23rd International Conference on Chemical Thermodynamics in Russia. Russia, Kazan, August 22–27, 2022. P. 298.Carrero-Mantilla J., Llano-Restrepo M. Vapor–phase chemical equilibrium for the hydrogenation of benzene to cyclohexane from reaction-ensemble molecular simulation. Fluid Phase Equil. 2004;219(2):181–193. https://doi.org/10.1016/j.fluid.2004.02.009Carrero-Mantilla J., Llano-Restrepo M. Vapor–phase chemical equilibrium for the hydrogenation of benzene to cyclohexane from reaction-ensemble molecular simulation. Fluid Phase Equil. 2004;219(2):181–193. https://doi.org/10.1016/j.fluid.2004.02.009Wang X., Xu W., Li Y., Wang J., He F. Phase equilibria of three binary systems containing 2,5-dimethylthiophene and 2-ethylthiophene in hydrocarbons. Fluid Phase Equil. 2016;409:30–36. https://doi.org/10.1016/j.fluid.2015.09.030Wang X., Xu W., Li Y., Wang J., He F. Phase equilibria of three binary systems containing 2,5-dimethylthiophene and 2-ethylthiophene in hydrocarbons. Fluid Phase Equil. 2016;409:30–36. https://doi.org/10.1016/j.fluid.2015.09.030Chen G., Wang Q., Zhang L.-Z., Bao J., Han S.-J. Study and applications of binary and ternary azeotropes. Thermochim. Acta. 1995;253:295–305. https://doi.org/10.1016/0040-6031(94)02078-3Chen G., Wang Q., Zhang L.-Z., Bao J., Han S.-J. Study and applications of binary and ternary azeotropes. Thermochim. Acta. 1995;253:295–305. https://doi.org/10.1016/00406031(94)02078-3

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