{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,6]],"date-time":"2026-10-06T07:11:06Z","timestamp":1791270666343,"version":"4.1.0"},"reference-count":102,"publisher":"MDPI AG","issue":"12","license":[{"start":{"date-parts":[[2023,6,20]],"date-time":"2023-06-20T00:00:00Z","timestamp":1687219200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Departamento de Ciencia, Tecnolog\u00eda y Universidad del Gobierno de Arag\u00f3n-Fondo Social Europeo","award":["E39_23R"],"award-info":[{"award-number":["E39_23R"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>Vapor pressures and other thermodynamic properties of liquids, such as density and enthalpy of mixtures, are the key parameters in chemical engineering for designing new process units, and are also essential for understanding the physical chemistry, macroscopic and molecular behavior of fluid systems. In this work, vapor pressures between 278.15 and 323.15 K, densities and enthalpies of mixtures between 288.15 and 318.15 K for the binary mixture (2-propanol + 1,8-cineole) have been measured. From the vapor pressure data, activity coefficients and excess Gibbs energies were calculated via the Barker\u2019s method and the Wilson equation. Excess molar volumes and excess molar enthalpies were also obtained from the density and calorimetric measurements. Thermodynamic consistency test between excess molar Gibbs energies and excess molar enthalpies has been carried out using the Gibbs\u2013Helmholtz equation. Robinson\u2013Mathias, and Peng\u2013Robinson\u2013Stryjek\u2013Vera together with volume translation of Peneloux equations of state (EoS) are considered, as well as the statistical associating fluid theory that offers a molecular vision quite suitable for systems having highly non-spherical or associated molecules. Of these three models, the first two fit the experimental vapor pressure results quite adequately; in contrast, only the last one approaches the volumetric behavior of the system. A brief comparison of the thermodynamic excess molar functions for binary mixtures of short-chain alcohol + 1,8-cineole (cyclic ether), or +di-n-propylether (lineal ether) is also included.<\/jats:p>","DOI":"10.3390\/ijms241210380","type":"journal-article","created":{"date-parts":[[2023,6,21]],"date-time":"2023-06-21T01:35:11Z","timestamp":1687311311000},"page":"10380","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Thermodynamic Behavior of (2-Propanol + 1,8-Cineole) Mixtures: Isothermal Vapor\u2013Liquid Equilibria, Densities, Enthalpies of Mixing, and Modeling"],"prefix":"10.3390","volume":"24","author":[{"given":"Beatriz","family":"Gimeno","sequence":"first","affiliation":[{"name":"Departamento de Qu\u00edmica F\u00edsica, Facultad de Ciencias, Universidad de Zaragoza, 50009 Zaragoza, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Santiago","family":"Martinez","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica F\u00edsica, Facultad de Ciencias, Universidad de Zaragoza, 50009 Zaragoza, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9379-8047","authenticated-orcid":false,"given":"Ana","family":"Mainar","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica F\u00edsica, Facultad de Ciencias, Universidad de Zaragoza, 50009 Zaragoza, Spain"},{"name":"Group of Applied Thermodynamics and Surfaces (GATHERS), Aragon Institute for Engineering Research (I3A), 50018 Zaragoza, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7569-5036","authenticated-orcid":false,"given":"Jos\u00e9","family":"Urieta","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica F\u00edsica, Facultad de Ciencias, Universidad de Zaragoza, 50009 Zaragoza, Spain"},{"name":"Group of Applied Thermodynamics and Surfaces (GATHERS), Aragon Institute for Engineering Research (I3A), 50018 Zaragoza, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pascual","family":"Perez","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica F\u00edsica, Facultad de Ciencias, Universidad de Zaragoza, 50009 Zaragoza, Spain"},{"name":"Instituto Agroalimentario de Arag\u00f3n (I2A), Centro de Investigaci\u00f3n y Tecnolog\u00eda Agroalimentaria de Arag\u00f3n (CITA), Universidad de Zaragoza, 50009 Zaragoza, Spain"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2023,6,20]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"938","DOI":"10.1080\/10286020.2020.1839432","article-title":"1,8-Cineole: A review of source, biological activities, and application","volume":"23","author":"Cai","year":"2020","journal-title":"J. Asian Nat. Prod. Res."},{"key":"ref_2","first-page":"241","article-title":"Monographs on botanical flavouring substances used in foods. Part V","volume":"67","author":"Mancini","year":"1996","journal-title":"Fitoterapia"},{"key":"ref_3","unstructured":"European Commission Health and Consumer Protection Directorate-General (2002). Opinion of the Scientific Committee on Food on Eucalyptol, Directorate C\u2014Scientific Opinions C2\u2014Management of Scientific Committees II."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"125","DOI":"10.5530\/rjps.2015.4.2","article-title":"Eucalyptol: Safety and Pharmacological Profile","volume":"5","author":"Bhowal","year":"2015","journal-title":"RGUHS J. Pharm. Sci."},{"key":"ref_5","first-page":"389","article-title":"Antimicrobial Activity of Common Mouthwash Solutions on Multidrug-Resistance Bacterial Biofilms","volume":"5","author":"Majed","year":"2013","journal-title":"J. Clin. Med. Res."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"69","DOI":"10.1186\/1465-9921-10-69","article-title":"Concomitant therapy with Cineole (Eucalyptole) reduces exacerbations in COPD: A placebo-controlled double-blind trial","volume":"10","author":"Worth","year":"2009","journal-title":"Respir. Res."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"638","DOI":"10.1055\/s-0034-1372609","article-title":"Anti-inflammatory properties of the monoterpene 1.8-cineole: Current evidence for co-medication in inflammatory airway diseases","volume":"64","author":"Juergens","year":"2014","journal-title":"Drug Res."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"540","DOI":"10.1002\/ffj.1843","article-title":"Antimicrobial activity of limonene enantiomers and 1,8-cineole alone and in combination","volume":"22","author":"Viljoen","year":"2007","journal-title":"Flavour Fragr. J."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"74","DOI":"10.1016\/j.micpath.2018.03.006","article-title":"Assessment of the antibiofilm and antiquorum sensing activities of Eucalyptus globulus essential oil and its main component 1,8-cineole against methicillin-resistant Staphylococcus aureus strains","volume":"118","author":"Merghni","year":"2018","journal-title":"Microb. Pathog."},{"key":"ref_10","first-page":"415","article-title":"In vitro antifungal activity of terpinen-4-ol, eugenol, carvone, 1,8-cineole (eucalyptol) and thymol against mycotoxigenic plant pathogens","volume":"29","author":"Morcia","year":"2012","journal-title":"Food Addit. Contam. Part A-Chem."},{"key":"ref_11","first-page":"820126","article-title":"The effect of 1,8-cineole inhalation on preoperative anxiety: A randomized clinical trial. Evid. Based Complement","volume":"24","author":"Kin","year":"2014","journal-title":"Altern. Med."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"167","DOI":"10.1016\/j.ijpharm.2006.05.018","article-title":"Skin penetration enhancement of mefenamic acid by ethanol and 1,8-cineole can be explained by the \u2018pull\u2019 effect","volume":"321","author":"Heard","year":"2006","journal-title":"Int. J. Pharm."},{"key":"ref_13","doi-asserted-by":"crossref","unstructured":"Dougnon, G., and Ito, M. (2020). Inhalation Administration of the Bicyclic Ethers 1,8- and 1,4-cineole Prevent Anxiety and Depressive-Like Behaviours in Mice. Molecules, 25.","DOI":"10.3390\/molecules25081884"},{"key":"ref_14","doi-asserted-by":"crossref","unstructured":"Abdalla, A.N., Shaheen, U., Abdallah, Q.M.A., Flamini, G., Bkhaitan, M.M., Abdelhady, M.I.S., Ascrizzi, R., and Bader, A. (2020). Proapoptotic Activity of Achillea membranacea Essential Oil and Its Major Constituent 1,8-Cineole against A2780 Ovarian Cancer Cells. Molecules, 25.","DOI":"10.3390\/molecules25071582"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"e05639","DOI":"10.1016\/j.heliyon.2020.e05639","article-title":"Anti-cancer mechanisms of linalool and 1,8-cineole in non-small cell lung cancer A549 cells","volume":"6","author":"Castro","year":"2020","journal-title":"Heliyon"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"150","DOI":"10.1007\/s12017-019-08574-2","article-title":"1,8-Cineole-Rich Extract of Small Cardamom Seeds More Effective in Preventing Alzheimer\u2019s Disease than 1,8-Cineole Alone?","volume":"22","author":"Paul","year":"2020","journal-title":"Neuromol. Med."},{"key":"ref_17","doi-asserted-by":"crossref","unstructured":"An, F., Bai, Y., Xuan, X., Bian, M., Zhang, G., and Wei, C. (2022). 8-Cineole Ameliorates Advanced Glycation End Products-Induced Alzheimer\u2019s Disease-like Pathology In Vitro and In Vivo. Molecules, 27.","DOI":"10.3390\/molecules27123913"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"149","DOI":"10.1007\/s42250-021-00302-3","article-title":"Targeting UDP-Glycosyltransferase, Glucosamine-6-Phosphate Synthase and Chitin Synthase by Using Bioactive 1,8 Cineole for \u201cAspergillosis\u201d Fungal Disease Mutilating COVID-19 Patients: Insights from Molecular Docking, Pharmacokinetics and In-vitro Studies","volume":"5","author":"Sharma","year":"2022","journal-title":"Chem. Afr."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"97","DOI":"10.1016\/j.scp.2018.10.005","article-title":"Eucalyptol-based green extraction of brown alga Zonaria tournefortii","volume":"10","author":"Hamiche","year":"2018","journal-title":"Sustain. Chem. Pharm."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"1531","DOI":"10.1039\/C8GC04016H","article-title":"Eucalyptol: A new solvent for the synthesis of heterocycles containing oxygen, sulfur and nitrogen","volume":"6","author":"Campos","year":"2019","journal-title":"Green Chem."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"112357","DOI":"10.1016\/j.fct.2021.112357","article-title":"FEMA GRAS assessment of natural flavor complexes: Eucalyptus oil and other cyclic ether-containing flavoring ingredients","volume":"155","author":"Eisenbrand","year":"2021","journal-title":"Food Chem. Toxicol."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"6065","DOI":"10.1039\/c3ra23174g","article-title":"Supercritical CO2 as a green solvent for eucalyptus and citrus essential oils processing: Role of thermal effects upon mixing","volume":"3","author":"Renuncio","year":"2013","journal-title":"RSC Adv."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"4546","DOI":"10.1039\/C4GC01149J","article-title":"A survey of solvent selection guides","volume":"16","author":"Prat","year":"2014","journal-title":"Green Chem."},{"key":"ref_24","doi-asserted-by":"crossref","unstructured":"Samudrala, S., and Bhattacharya, S. (2018). Toward the Sustainable Synthesis of Propanols from Renewable Glycerol over MoO3-Al2O3 Supported Palladium Catalysts. Catalysts, 8.","DOI":"10.3390\/catal8090385"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"65","DOI":"10.4236\/jsbs.2017.72006","article-title":"The Production of 1,8-Cineole, a Potential Biofuel, from an Endophytic Strain of Annulohypoxylon sp. FPYF3050 When Grown on Agricultural Residues","volume":"7","author":"Wang","year":"2017","journal-title":"J. Sustain. Bioenergy Syst."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"177","DOI":"10.26701\/ems.962605","article-title":"Research of effect on gasoline-2-propanol blends on exhaust emission of gasoline engine with direct injection using Taguchi approach","volume":"5","author":"Tasoren","year":"2021","journal-title":"Eur. Mech. Sci."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"815","DOI":"10.1016\/j.fuel.2005.08.027","article-title":"Effect of ethers and ether\/ethanol additives on the physicochemical properties of diesel fuel and on engine tests","volume":"85","author":"Weberdemenezes","year":"2006","journal-title":"Fuel"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"3555","DOI":"10.1039\/b003024o","article-title":"Exploring a hydrogen-bond terminus: Spectroscopy of eucalyptol\u2013alcohol clusters","volume":"2","author":"Raveendran","year":"2000","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"146","DOI":"10.1016\/j.cplett.2016.11.045","article-title":"Subtle differences in the hydrogen bonding of alcohol to divalent oxygen and sulfur","volume":"667","author":"Du","year":"2017","journal-title":"Chem. Phys. Lett."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"3167","DOI":"10.1021\/jp067405b","article-title":"Properties of 1,8-Cineole: A Thermophysical and Theoretical Study","volume":"11","author":"Aparicio","year":"2007","journal-title":"J. Phys. Chem. B"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"280","DOI":"10.1016\/j.jct.2014.04.022","article-title":"Thermodynamic study of selected monoterpenes III","volume":"79","author":"Fulem","year":"2014","journal-title":"J. Chem. Thermodyn."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"1393","DOI":"10.1021\/je800024u","article-title":"Setup and Validation of a P \u03c1 T Measuring Device. Volumetric Behavior of the Mixture 1,8-Cineole + Ethanol","volume":"53","author":"Lasarte","year":"2008","journal-title":"J. Chem. Eng. Data"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"291","DOI":"10.1016\/j.jct.2009.08.016","article-title":"Thermophysical properties of the binary mixtures (1,8-cineole + 1-alkanol) at T = (298.15 and 313.15) K and at atmospheric pressure","volume":"42","author":"Alfaro","year":"2010","journal-title":"J. Chem. Thermodyn."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"5932","DOI":"10.1021\/je100577v","article-title":"P, \u03c1, T Measurements and Isobaric Vapor-Liquid-Equilibria of the 1,3,3-Trimethyl-2-oxabicycle[2,2,2]octane + Propan-1-ol Mixture: Cubic and Statistical Associating Fluid Theory-Based Equation of State Analysis","volume":"55","author":"Torcal","year":"2010","journal-title":"J. Chem. Eng. Data"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"2443","DOI":"10.1021\/je200011e","article-title":"Isothermal Vapor-Liquid Equilibrium of (1-butanol + 1,8-cineole) at Ten Temperatures between 278.15 K and 323.15 K","volume":"56","author":"Gimeno","year":"2011","journal-title":"J. Chem. Eng. Data"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"83","DOI":"10.1016\/j.fluid.2011.07.002","article-title":"Total vapour pressure and excess Gibbs energy of ethanol with 1,8-cineole at temperatures between 278.15 K and 323.15 K","volume":"309","author":"Gimeno","year":"2011","journal-title":"Fluid Phase Equilib."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"3026","DOI":"10.1021\/je300736k","article-title":"Vapor Pressures and Activity Coefficients of (1-propanol + 1,8-cineole) at 10 Temperatures between 278.15 K and 323.15 K","volume":"57","author":"Gimeno","year":"2012","journal-title":"J. Chem. Eng. Data"},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"59","DOI":"10.1021\/i160057a011","article-title":"A New Two-Constant Equation of State","volume":"15","author":"Peng","year":"1976","journal-title":"Ind. Eng. Chem. Fundam."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"2284","DOI":"10.1021\/ie00107a014","article-title":"Equation of State for Small, Large, Polydisperse and Associating Molecules","volume":"29","author":"Huang","year":"1990","journal-title":"Ind. Eng. Chem. Res."},{"key":"ref_40","unstructured":"van der Waals, J.D. (1873). Over de Continuiteit van den Gas en Vloeistoftoestand. [Ph.D. Thesis, Leiden University]."},{"key":"ref_41","unstructured":"Reedijk, J. (2018). Computer-aided molecular design: Fundamentals, methods, and applications. Elsevier Reference Module in Chemistry, Molecular Sciences and Chemical Engineering, Elsevier."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"39","DOI":"10.1016\/j.fluid.2017.05.007","article-title":"Peng-Robinson equation of state: 40 years through cubics","volume":"447","year":"2017","journal-title":"Fluid Phase Equilib."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"1603","DOI":"10.1021\/ie020447b","article-title":"The state of the cubic equations of state","volume":"42","author":"Valderrama","year":"2003","journal-title":"Ind. Eng. Chem. Res."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"385","DOI":"10.1021\/i200022a008","article-title":"A Versatile Phase Equilibrium Equation of State","volume":"22","author":"Mathias","year":"1983","journal-title":"Ind. Eng. Chem. Process Des. Dev."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"323","DOI":"10.1002\/cjce.5450640224","article-title":"PRSV: An Improved Peng-Robinson Equation of State for Pure Compounds and Mixtures","volume":"64","author":"Stryjek","year":"1986","journal-title":"Can. J. Chem. Eng."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"7","DOI":"10.1016\/0378-3812(82)80002-2","article-title":"A Consistent Correction for Redlich-Kwong-Soave Volumes","volume":"8","author":"Peneloux","year":"1982","journal-title":"Fluid Phase Equilib."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"19","DOI":"10.1007\/BF01017362","article-title":"Fluids with highly directional attractive forces: I. Statistical thermodynamics","volume":"35","author":"Wertheim","year":"1984","journal-title":"J. Stat. Phys."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"477","DOI":"10.1007\/BF01127722","article-title":"Fluids with highly directional attractive forces: IV. Equilibrium polymerization","volume":"42","author":"Wertheim","year":"1986","journal-title":"J. Stat. Phys."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"2193","DOI":"10.1021\/ie000773w","article-title":"Molecular-Based Equations of State for Associating Fluids: A Review of SAFT and Related Approaches","volume":"40","author":"Gubbins","year":"2001","journal-title":"Ind. Eng. Chem. Res."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"31","DOI":"10.1016\/0378-3812(89)80308-5","article-title":"SAFT Equationof- State Solution Model for Associating Fluids","volume":"52","author":"Chapman","year":"1989","journal-title":"Fluid Phase Equilib."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"1709","DOI":"10.1021\/ie00104a021","article-title":"New Reference Equation of State for Associating Liquids","volume":"29","author":"Chapman","year":"1990","journal-title":"Ind. Eng. Chem. Res."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"5510","DOI":"10.1021\/ie010954d","article-title":"Application of the Perturbed-Chain SAFT Equation of State to Associating Systems","volume":"41","author":"Gross","year":"2002","journal-title":"Ind. Eng. Chem. Res."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"3933","DOI":"10.1021\/ie303248q","article-title":"Evaluation of Cubic, SAFT, and PC-SAFT Equations of State for the Vapor\u2013Liquid Equilibrium Modeling of CO2 Mixtures with Other Gases","volume":"52","author":"Diamantonis","year":"2013","journal-title":"Ind. Eng. Chem. Res."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"113570","DOI":"10.1016\/j.fluid.2022.113570","article-title":"Prediction of phase equilibria, density, speed of sound and viscosity of 2-alkoxyethanols mixtures: A comparison study between SAFT type EoSs and a modified PR EoS","volume":"563","author":"Velasquez","year":"2022","journal-title":"Fluid Phase Equilib."},{"key":"ref_55","first-page":"641","article-title":"Building the liquid-vapour equilibrium curve through a cubic equation of state: Use of excel for teaching physical-chemistry","volume":"39","author":"Pliego","year":"2016","journal-title":"Quim. Nova"},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"4619","DOI":"10.1021\/acs.jced.9b00264","article-title":"Taking Another Look at the van der Waals Equation of State\u2014Almost 150 Years Later","volume":"64","author":"Kontogeorgis","year":"2019","journal-title":"J. Chem. Eng. Data"},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"3788","DOI":"10.1021\/acs.jced.1c00410","article-title":"Measurements, Correlations, and Modified UNIFAC Predictions of Isobaric Vapor-Liquid Equilibrium Data for the Binary System of Dimethyl Carbonate plus Anisole at Different Pressures","volume":"66","author":"Kamesh","year":"2021","journal-title":"J. Chem. Eng. Data"},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"53","DOI":"10.1007\/s12039-019-1630-9","article-title":"Theoretical and experimental study of physicochemical behavior of binary mixtures: SAFT and PC-SAFT models","volume":"13","author":"Sarkoohaki","year":"2019","journal-title":"J. Chem. Sci."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"1335","DOI":"10.1016\/j.jct.2010.05.009","article-title":"Excess molar volume, viscosity, and refractive index study for the ternary mixture {2-methyl-2-butanol + tetrahydrofuran + propylamine} at different temperatures. Application of the ERAS-model and Peng\u2013Robinson\u2013Stryjek\u2013Vera equation of state","volume":"42","author":"Fattahi","year":"2010","journal-title":"J. Chem. Thermodyn."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"146","DOI":"10.1016\/j.jct.2015.09.012","article-title":"Molar heat capacities of the mixture {1,8-cineole + ethanol} at several temperatures and atmospheric pressure","volume":"92","author":"Schneider","year":"2016","journal-title":"J. Chem. Thermodyn."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"88","DOI":"10.1016\/j.jct.2016.01.008","article-title":"Isobaric VLE of the mixture {1,8-cineole + ethanol}. EOS analysis and COSMO-RS modeling","volume":"97","author":"Torcal","year":"2016","journal-title":"J. Chem. Thermodyn."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"131","DOI":"10.1016\/S0378-3812(97)00173-8","article-title":"Isothermal vapour-liquid equilibrium at eight temperatures and excess functions at 298.15 K of di-n-propylether with 1-propanol or 2-propanol","volume":"138","author":"Garriga","year":"1997","journal-title":"Fluid Phase Equilib."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"1466","DOI":"10.1002\/bbpc.199700008","article-title":"Vapour Pressures at Eight Temperatures of Mixtures of Di-n-Propylether + Ethanol or 1-ButanolThermodynamic Description of Mixtures of Di-n-Propylether + Alkanol According to the ERAS Model","volume":"101","author":"Garriga","year":"1997","journal-title":"Ber. Bunsen-Ges. Phys. Chem."},{"key":"ref_64","unstructured":"Thermodynamics Research Center (1966). TRC-Thermodynamic Tables-Non-Hydrocarbons."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"505","DOI":"10.1016\/0021-9614(87)90147-9","article-title":"Vapour pressures and critical temperatures of some alkanoic acids: C1 to C10","volume":"19","author":"Ambrose","year":"1987","journal-title":"J. Chem. Thermodynamic."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"517","DOI":"10.1021\/ie50448a022","article-title":"Vapour Pressure or Pure Substances. Organic Compound","volume":"39","author":"Stull","year":"1947","journal-title":"Ind. Eng. Chem."},{"key":"ref_67","first-page":"43","article-title":"Vapor pressures and sublimation pressures of eight constituets of essential oils at pressures in the range from 0.3 to 83,000 Pa","volume":"5","author":"Guetachew","year":"1999","journal-title":"ELDATA Int. Electron. J. Phys. Chem. Dat."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"263","DOI":"10.1002\/aic.690200209","article-title":"Empirical Correlation of Second Virial Coeficients","volume":"20","author":"Tsonopoulos","year":"1974","journal-title":"AIChE J."},{"key":"ref_69","unstructured":"Erickson, W.D., and Roach, J.F. (1965). Composition and Thermodynamic Properties of Reacting Gas Mixtures under High Pressures Using the Lewis and Randall Rule, National Aeronautics and Space Administration. Nasa Technical Note TN D-2591."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"207","DOI":"10.1071\/CH9530207","article-title":"Determination of Activity Coefficients from Total Pressure Measurements","volume":"6","author":"Barker","year":"1953","journal-title":"Aust. J. Chem."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"127","DOI":"10.1021\/ja01056a002","article-title":"Vapor-Liquid Equilibrium. 11. A New Expression for the Excess Free Energy of Mixing","volume":"86","author":"Wilson","year":"1964","journal-title":"J. Am. Chem. Soc."},{"key":"ref_72","unstructured":"Swinton, F.L. (1982). Excess thermodynamic functions. Liquids and Liquid Mixtures, Butterworth. [3rd ed.]. Chapter 5."},{"key":"ref_73","first-page":"479","article-title":"Molecular Polarisability: The Anisotropy of the Carbon-Oxygen Link","volume":"2","author":"Sundaram","year":"1963","journal-title":"J. Chem. Soc."},{"key":"ref_74","unstructured":"Mc Clellan, A.L. (1974). Tables of Experimental Dipole Moments, Rahara Enterprises."},{"key":"ref_75","first-page":"390","article-title":"The dipolar moment of the n-propyl ether","volume":"33","author":"Meyer","year":"1932","journal-title":"Physik. Z."},{"key":"ref_76","unstructured":"Mc Clellan, A.L. (1963). Tables of Experimental Dipole Moments, Freeman."},{"key":"ref_77","first-page":"93","article-title":"H\n\t\t\t\tm\n\t\t\t\tE\n\t\t\t\n\t\t\t\n          \n        \n\t\t   and \n        \n          \n            \n\t\t\t\n\t\t\t\tV\n\t\t\t\tm\n\t\t\t\tE\n\t\t\t\n\t\t\t\n          \n        \n\t\t   of some (butanone or dipropylether + an alkanol) mixtures","volume":"20","author":"Valero","year":"1988","journal-title":"J. Chem. Thermodyn."},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"273","DOI":"10.1016\/0021-9614(69)90047-0","article-title":"The thermodynamics properties of solutions of normal and branched alcohols in benzene and n-hexane","volume":"1","author":"Brown","year":"1969","journal-title":"J. Chem. Thermodyn."},{"key":"ref_79","first-page":"594","article-title":"Part 1: Heats of Mixing Data Collection","volume":"Volume III","author":"Christensen","year":"1984","journal-title":"DECHEMA Chemistry Data Series"},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"925","DOI":"10.1007\/BF00905064","article-title":"Thermodynamics of the isopropanol\/n-hexane and isopropanol\/n-heptane systems. Part III. Gas\/liquid equilibrium","volume":"112","author":"Barraza","year":"1981","journal-title":"Monatsh. Chem."},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"303","DOI":"10.1016\/j.molliq.2018.07.043","article-title":"Volumetric, acoustic and optical properties of binary mixtures of 2-propanol with n-alkanes (C 6\u2013C 10) from 293.15 K to 303.15 K","volume":"268","author":"Kashyap","year":"2018","journal-title":"J. Mol. Liq."},{"key":"ref_82","doi-asserted-by":"crossref","first-page":"1097","DOI":"10.1021\/je00021a014","article-title":"CH4O and C4H8O. Primary linear-alkyl monoalcohols + Cyclic monoethers: Heat of Mixing and Solution","volume":"40","author":"Letcher","year":"1995","journal-title":"J. Chem. Eng. Data"},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"57","DOI":"10.1016\/0040-6031(95)02747-5","article-title":"Disquac analysis of binary-liquid organic mixtures containing cyclic or linear alkanols and cycloalkanes or n-alkanes","volume":"278","author":"Cobos","year":"1996","journal-title":"Thermochim. Acta"},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"785","DOI":"10.1103\/PhysRevB.37.785","article-title":"Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density","volume":"37","author":"Lee","year":"1988","journal-title":"Phys. Rev. B"},{"key":"ref_85","doi-asserted-by":"crossref","first-page":"1372","DOI":"10.1063\/1.464304","article-title":"A new mixing of Hartree\u2013Fock and local density-functional theories","volume":"98","author":"Becke","year":"1993","journal-title":"J. Chem. Phys."},{"key":"ref_86","doi-asserted-by":"crossref","first-page":"5648","DOI":"10.1063\/1.464913","article-title":"Density functional thermochemistry. III. The role of exact exchange","volume":"98","author":"Becke","year":"1993","journal-title":"J. Chem. Phys."},{"key":"ref_87","doi-asserted-by":"crossref","first-page":"597","DOI":"10.1016\/S0097-8485(99)00039-X","article-title":"Computational tools for the electron localization function topological analysis","volume":"23","author":"Noury","year":"1999","journal-title":"Comput. Chem."},{"key":"ref_88","doi-asserted-by":"crossref","first-page":"1192","DOI":"10.1016\/j.molliq.2016.08.011","article-title":"Refractive index, speed of sound, FT-IR and computational study of intermolecular interaction between binary mixtures of 1,8-cineole with o-, m- and p-cresol at 303.15, 308.15 and 313.15 K","volume":"222","author":"Patel","year":"2016","journal-title":"J. Mol. Liq."},{"key":"ref_89","doi-asserted-by":"crossref","first-page":"931","DOI":"10.1016\/0021-9614(88)90222-4","article-title":"HmE of (an n-alkane+ a butanol isomer)","volume":"20","author":"Jimenez","year":"1988","journal-title":"J. Chem. Thermodyn."},{"key":"ref_90","unstructured":"Pfohl, O., Petkov, S., and Brunner, G. (2000). PE 2000. A Poweful Tool to Correlate Phase Equilibria, Herbert Utz."},{"key":"ref_91","unstructured":"Poling, B.E., Prausnitz, J.M., and O\u2019Connell, J.P. (2007). The Properties of Gases and Liquids, Mc Graw-Hill. [5th ed.]."},{"key":"ref_92","doi-asserted-by":"crossref","first-page":"883","DOI":"10.1039\/tf9686400883","article-title":"Thermodynamics of Octamethylcyclotetrasiloxane Mixtures","volume":"64","author":"Marsh","year":"1968","journal-title":"Trans. Faraday Soc."},{"key":"ref_93","doi-asserted-by":"crossref","first-page":"523","DOI":"10.1006\/jcht.2000.0766","article-title":"Isothermal (vapour + liquid) equilibrium at several temperatures of (1-chlorobutane + 1-butanol, or 2-methyl-2-propanol)","volume":"33","author":"Garriga","year":"2001","journal-title":"J. Chem. Thermodyn."},{"key":"ref_94","doi-asserted-by":"crossref","first-page":"1437","DOI":"10.1351\/pac197749091437","article-title":"Recommended reference materialsfor realization of physicochemical properties","volume":"49","author":"Ambrose","year":"1977","journal-title":"IUPAC Pure Appl. Chem."},{"key":"ref_95","doi-asserted-by":"crossref","first-page":"1412","DOI":"10.1021\/ja01929a006","article-title":"Studiesin Vapor Pressure: III. A Static Method for Determining the Vapor Pressures of Solids and Liquids","volume":"32","author":"Smith","year":"1910","journal-title":"J. Am. Chem. Soc."},{"key":"ref_96","unstructured":"Marsh, K.N. (1987). Enthalpy. Recommended Reference Materials for the Realization of Physicochemical Properties, Blackwell Scientific Publications. Chapter 9."},{"key":"ref_97","doi-asserted-by":"crossref","first-page":"665","DOI":"10.1080\/00319100108031683","article-title":"Excess Molar Enthalpies for Isomeric Chlorobutanes with Isomeric Butanols","volume":"39","author":"Lafuente","year":"2001","journal-title":"Phys. Chem. Liq."},{"key":"ref_98","doi-asserted-by":"crossref","first-page":"1649","DOI":"10.1016\/j.jct.2007.04.006","article-title":"Density and speed of sound of lithium bromide with organic solvents: Measurement and correlation","volume":"39","author":"Shekaaria","year":"2007","journal-title":"J. Chem. Thermodyn."},{"key":"ref_99","doi-asserted-by":"crossref","first-page":"223","DOI":"10.1524\/zpch.1994.187.Part_2.223","article-title":"Properties of the liquid-system water plus 2-propanol","volume":"187","author":"Haase","year":"1994","journal-title":"Z. Phys. Chem."},{"key":"ref_100","doi-asserted-by":"crossref","first-page":"115","DOI":"10.1016\/j.jct.2008.07.010","article-title":"Studies of mixing properties of binary systems of 2-propanol with hexadecane and squalane at T = (298.15, 303.15, and 308.15)","volume":"41","author":"Dubey","year":"2009","journal-title":"J. Chem. Thermodyn."},{"key":"ref_101","doi-asserted-by":"crossref","first-page":"31","DOI":"10.1021\/je00009a008","article-title":"Densities, viscosities, refractive indices, and speeds of sound for methyl acetoacetate + aliphatic alcohols (C1\u2013C8)","volume":"38","author":"Aminabhavi","year":"1993","journal-title":"J. Chem. Eng. Data"},{"key":"ref_102","doi-asserted-by":"crossref","first-page":"298","DOI":"10.1021\/je00014a023","article-title":"Densities and Viscosities of Thymol + 1,8-Cineole","volume":"39","author":"Barata","year":"1994","journal-title":"J. Chem. Eng. Data"}],"container-title":["International Journal of Molecular Sciences"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1422-0067\/24\/12\/10380\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,4,16]],"date-time":"2026-04-16T11:36:26Z","timestamp":1776339386000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1422-0067\/24\/12\/10380"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,6,20]]},"references-count":102,"journal-issue":{"issue":"12","published-online":{"date-parts":[[2023,6]]}},"alternative-id":["ijms241210380"],"URL":"https:\/\/doi.org\/10.3390\/ijms241210380","relation":{},"ISSN":["1422-0067"],"issn-type":[{"value":"1422-0067","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,6,20]]}}}