Excess/deviation properties of binary mixtures of 2,5-dimethylfuran with furfuryl alcohol, methyl isobutyl ketone, 1-butanol and 2-butanol at temperature range of (293.15–323.15) K

Mohammad Ridha Mahi; Faiza Ouaar; Amina Negadi; Indra Bahadur; Latifa Negadi

doi:10.2516/ogst/2018012

Dossier: Thermal analysis and calorimetry techniques applied to the characterization of materials and fluids for energy

Open Access

Numéro		Oil & Gas Science and Technology - Rev. IFP Energies nouvelles Volume 73, 2018 Dossier: Thermal analysis and calorimetry techniques applied to the characterization of materials and fluids for energy


Numéro d'article		64
Nombre de pages		15
DOI		https://doi.org/10.2516/ogst/2018012
Publié en ligne		30 novembre 2018

Oil & Gas Science and Technology - Rev. IFP Energies nouvelles 73, 64 (2018)

Regular Article

Excess/deviation properties of binary mixtures of 2,5-dimethylfuran with furfuryl alcohol, methyl isobutyl ketone, 1-butanol and 2-butanol at temperature range of (293.15–323.15) K

Mohammad Ridha Mahi¹, Faiza Ouaar¹, Amina Negadi¹, Indra Bahadur² and Latifa Negadi¹^,3^*

¹ LATA2M, Laboratoire de Thermodynamique Appliquée et Modélisation Moléculaire, University of Tlemcen, Post Office Box 119, Tlemcen 13000, Algeria
² Department of Chemistry and Material Science Innovation & Modelling (MaSIM) Research Focus Area, Faculty of Agriculture, Science and Technology, North-West University (Mafikeng Campus), Private Bag X2046, Mmabatho 2735, South Africa
³ Thermodynamics Research Unit, School of Engineering, University of KwaZulu-Natal, Howard College Campus, King George V Avenue, 4041 Durban, South Africa

^* Corresponding author: l_negadi@mail.univ-tlemcen.dz

Received: 13 November 2017
Accepted: 12 March 2018

Abstract

Experimental values of density and speed of sound for binary liquid mixtures of 2,5-dimethylfuran (2,5-DMF) with furfuryl alcohol (FA), methyl isobutyl ketone (MIBK), 1-butanol and 2-butanol and over the entire composition range of 2,5-DMF and at the temperature range of 293.15–323.15 K at 10 K intervals and at pressure p = 0.1 MPa were reported. Experimental data were used to assess the thermodynamics properties of studied mixtures. These properties were used to interpret the molecular interactions among component of liquids. The values of excess/deviation functions have been fitted to Redlich−Kister type polynomial equation. From the obtained results, a discussion was carried out in terms of nature of intermolecular interactions and structure factors in the binary mixtures.

Key words: DMF / Biomass / Density / Speed of sound / Redlich-Kister / polynomial equation

© M.R. Mahi et al., published by IFP Energies nouvelles, 2018

This is an Open Access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

1 Introduction

Nowadays, fossil energies such as petroleum, natural gas and coal dominate approximately more than 80% of primary energy consumption estimated by sources [1]. This excessive reliance on fossil fuels in the world has serious reservations about their depletion and green house emission. Now, with increasing the demand for environmental concerns about global warming, the development of eco-friendly and renewable energy sources have been a most important topic in the last few years [2,3]. The energy-efficient processes for the sustainable production of fuels derived from biomass such as biodiesel fuel (BDF), bio-ethanol and liquid alkanes have also attracted attention over the year [4].

5-hydroxymethylfurfural (HMF), obtained by dehydration of monosaccharides, is considered to be most promising important intermediate for the synthesis of a wide variety of chemicals and alternative fuels based on bio-refinery [5]. To upgrade furanic compounds toward bio-fuels, hydrogenation is the most versatile reaction. Among several furan-based biofuel candidates, which include 2,5-dimethylfuran (2,5-DMF), 2-methylfuran (2-MF), 5-ethoxymethylfurfural (EMF) and ethyl levulinate (EL), 2,5-dimethylfuran is known as one of the potential transportation fuels because of its high energy density (30 kJ · cm⁻³) together octane number (RON = 119), these values are similar to the gasoline which also have high energy density (34ckJ · cm⁻³) together octane number (RON = 96). Moreover, DMF is nearly immiscible with water and thus easier to blend with gasoline than ethanol.

To explore the application of DMF as a fuel or as a gasoline additive, it is necessary to characterize its thermophysical properties including density, sound velocity, refractive indices, viscosity, surface tension and vapor–liquid equilibrium as a pure fluid as well as mixed with hydrocarbons or other gasoline additives. In the face of their importance, experimental and theoretical investigations concerning key properties are scarce and limited to narrow experimental conditions.

For the case of binary systems {2,5-dimethylfuran (2,5-DMF) + FA or MIBK or 1-butanol, or 2-butanol}, neither excess molar volumes ( $V_{m}^{E}$ ), nor isentropic compressibility (ks) data have been previously reported. Consequently, and as continuation of our systematic studies on thermodynamic and thermophysical properties of binary mixtures containing solvents derived from biomass, the present work is undertaken to measure new experimental data of densities, sound velocity, refractive indices of pure DMF and of the binary systems {2,5-dimethylfuran (2,5-DMF) + FA or MIBK or 1-butanol, or 2-butanol} over the entire composition range at (293.15, 303.15, 313.15 and 323.15) K and at pressure p = 0.1 MPa. Reliable density and speed of sound data for the measured systems are needed for optimized design of several industrial processes such as separation, storage, mixing processes, and transport. These data also used to develop accurate empirical equations, models and simulation programs. The results from these studies can provide valuable information about fluid at different temperature conditions including room temperatures to higher temperatures at 50 °C.

2 Experimental details

2.1 Chemicals

2,5-dimethylfuran (2,5-DMF), FA and 2-butanol were purchased from Sigma Aldrich, while 1-butanol was from Biochem and MIBK was from Fluka. The purity of these chemicals were declared to be more than 0.99 on mass fraction basis. The source and the purity of the utilized chemicals are shown in Table 1. As well the purity was checked by comparing the measured densities, speed of sound and refractive index, which are in good accord with literature values [6–65] and are presented in Table 2. All chemicals were kept in bottles to avoid contamination and evaporation during mixing.

Table 1

Molar mass, CAS number, suppliers and purities of chemicals used in this study.

Table 2

Comparison of experimental density, ρ, sound velocity, u, and refractive indices, n_D, of the pure component with the corresponding literature values at 293.15, 298.15, 303.15, 313.15 and 323.15 K and at pressure p = 0.1 MPa.

2.2 Apparatus and procedure

The binary mixtures were prepared by mass measurement using an OHAUS analytical mass balance with a precision of ±0.0001 g. The uncertainty in the mole fraction was ±0.0005. Density and speed of sound for pure components and their binary mixtures were measured using a digital vibrating-tube densimeter and sound velocity analyzer (Anton Paar DSA 5000M) with uncertainty of ±0.02 K in temperature. The speed of sound was measured using a propagation time technique with frequency of 3 MHz. The estimated uncertainty in density and speed of sound were ±0.003 g·cm⁻³ and ±1.2 m·s⁻¹, respectively. The refractive indices of the pure liquids used in the present work were measured using an Abbe digital refractometer (Model Abbemat 300, Anton Paar), with uncertainty of ±0.02 K in temperature. The measured values of the refractive indices using the method and apparatus were estimated to be ±0.005 of their true values.

3 Results and discussion

3.1 Density

The values of density ρ were measured at (293.15, 303.15, 313.15 and 323.15) K, and at pressure p = 0.1 MPa for the binary systems {2,5-dimethylfuran (2,5-DMF) + FA or MIBK or 1-butanol, or 2-butanol} and are given in Table 3. The plots of density versus concentration at investigated temperatures are given in Figure S1 (a)–(d). From Figure S1 (a)–(d), it can be seen that the ρ values decreases with an increase in temperature, and increases with an increase in concentration for all investigated binary systems, except for the system containing FA whereas a decreasing value of ρ with an increase in concentration was observed.

Table 3

Densities, ρ, sound velocity, u, and isentropic compressibility, κs, for the binary systems {2,5-DMF (1)+FA (2), or MIBK (2), or 1-butanol (2), or 2-butanol (2)} at (293.15, 303.15, 313.15 and 323.15) K and at pressure p = 0.1 MPa.

3.2 Speed of sound

The measurement of speed of sound, u, has been successfully employed in understanding the nature of molecular interactions in pure liquids and their liquid mixtures [66–68]. Speed of sound measurements are highly sensitive to molecular interactions and can be used to provide qualitative information about the physical nature and strength of molecular interaction in liquid mixtures [66–68]. In this regards, the speed of sound data, were also measured in the same conditions for all binary systems and are also given in Table 3. The plots of speed of sound versus concentration, at investigated temperatures, are given in Figure S2 (a)–(d). From Figure S2 (a)–(d), it can be seen that the u values also decreases with an increase in temperature, and in general, decreases with an increase in concentration for all binary systems excluding the {2,5-dimethylfuran + MIBK) system, whereas an increasing values of u with an increase in concentration was observed. Figure S2 (a)–(d), representing the variation of u as a mole fraction of 2,5-dimethylfuran for the systems containing FA or MIBK or 1-butanol, or 2-butanol, shows that at a given temperature, the curve of u as a function of x₁ has a maximum of x₁ = 0.6773 for MIBK whereas a minimum of x₁ = 0.9004 for FA, x₁ = 0.7944 for 1-butanol and x₁ = 0.6860 for 2-butanol. The minimum of x₁ observed for the systems whereas u value decreases with an increase in concentration while maximum of x₁ observed for the systems whereas an increasing value of u with increasing concentration was observed.

3.3 Excess molar volumes

The excess molar volumes, $V_{m}^{E}$ , were calculated from the density data of the mixture and the pure components using Equation (1): $V_{m}^{E} = \frac{x_{1} M_{1} + x_{2} M_{2}}{ρ} - \frac{x_{1} M_{1}}{ρ_{1}} - \frac{x_{2} M_{2}}{ρ_{2}} .$ (1) where x₁ and x₂ are mole fractions; M₁ and M₂ denote molar masses; ρ₁ and ρ₂ are the densities; where 1 refers to 2,5-dimethylfuran and 2 refers to FA or 1-butanol or 2-butanol or MIBK, and ρ is the density of the mixtures. Table S1 represents the results of excess molar volume, $V_{m}^{E}$ , for the studied system and is also plotted in Figure S1 (a)–(d). The $V_{m}^{E}$ values are positive for the systems (2,5-dimethylfuran + 1-butanol, or 2-butanol) and negative for the systems (2,5-dimethylfuran + MIBK, or FA). The positive $V_{m}^{E}$ values can be explained by (i) mutual loss of dipolar association due to addition of the 1-butanol or 2-butanol and contributions due to difference in size and shape of the components in the mixtures, and (ii) dipole–dipole and dipole-induced dipole interaction between unlike molecules. The first factor contributes to expansion in volume and second factor contributes to decrease in volume, which will cause contraction in volume. The experimental results in this work suggested that the factors responsible for expansion in volume are dominant over the entire composition range in the mixtures (2,5-DMF + the 1-butanol or 2-butanol) systems whereas an inversion in sign for (2,5-DMF + MIBK or FA) systems suggested that factors responsible for decrease in volume are dominant over the composition range. As can been seen the results in Table S1, the $V_{m}^{E}$ values at x₁ = 0.5938 for 2-butanol>1-butanol>MIBK>FA indicating that the interaction between 2,5-DMF with FA or MIBK or 1-butanol or 2-butanol as in order FA>MIBK>1-butanol>2-butanol. This observation based on fact that lower the _{$V_{m}^{E}$} values have stronger interaction and vice versa. From Figure 1 (a)–(d), shows that the $V_{m}^{E}$ values increase with the temperature for all systems except MIBK whereas decrease with temperature. The $V_{m}^{E}$ minimum and maximum values increase with an increase in temperature for all the systems except the system containing FA. The excess molar volume of an equimolar mixtures for studied systems at 293.15, 303.15, 313.15 and 323.15 K are −0.266, −0.292, −0.318, −0.344 for FA; −0.231, −0.229, −0.223, −0.222 for MIBK; 0.112, 0.150, 0.195, 0.245 for 1-butanol and 0.395, 0.472, 0.549, 0.625 for 2-butanol were observed.

Fig. 1

Plot of excess molar volumes, $V_{m}^{E}$ , for the binary mixtures: (a) {2,5-DMF (1)+FA (2)}; (b) {2,5-DMF (1)+MIBK (2)}; (c) {2,5-DMF (1)+1-butanol (2)} and (d) {2,5-DMF (1)+2-butanol (2)} as function of the composition expressed in the mole fraction at 293.15 K (♦); 303.15 K (■); 313.15 K (▲) and 323.15 K (●). The dotted lines were generated using Redlich-Kister polynomial curve-fitting.

3.4 Isentropic compressibility, and deviation in isentropic compressibility

The Newton–Laplace equation was used to calculate the isentropic compressibility, κ_s, $κ_{s} = \frac{1}{ρ u^{2}}$ (2) The deviations in isentropic compressibility, Δκ_s, were calculated using the equation given below: ${Δ κ}_{s (x)} = κ_{s} - \sum_{i}^{2} x_{i} κ_{s, i}$ (3)where κ_s,_i and x_i are the isentropic compressibility and mole fractions of the pure component i, respectively. The results of isentropic compressibility, κ_s, for studied systems at 293.15, 303.15, 313.15 and 323.15 K are given in Table 3 and are also plotted in Figure S3 (a)–(d). The isentropic compressibility, κ_s, value increases with an increase in temperature at a fixed composition for all binary systems due to an increase in thermal agitation, making the solution more compressible [69]. The κ_s value increases with an increase in temperature and increases with an increase in the concentration of 2,5-DMF at a fixed temperature for the system of 2,5-DMF with FA, 1-butanol and 2-butanol except for the 1-butanol, 2-butanol systems whereas start decreasing from x_1 =0.5099, x₁ ₌ 0.1972 upwards respectively, while for the MIBK solution of 2,5-DMF, decreases with concentration.

It is well known that the addition of 2,5-DMF molecules to self-associated hydrogen bonded FA,1-butanol and 2-butanol will induce breaking of clusters of these molecules thereby releasing so many dipoles, which interact with dipoles of 2,5-DMF. This causes an increase in free space, decrease in speed of sound and positive deviation in isentropic compressibility [70]. The calculated Δκ_s values for studied system at (293.15, 303.15, 313.15 and 323.15) K are also given in Table S1 and are graphically presented in Figure 2 (a)–(d). It is observed from Figure 2 (a)–(d), the values of Δκ_s are negative for (2,5-DMF + MIBK) binary system, and both positive and negative for the systems (2,5-DMF + FA). The positive values of Δκ_s are also observed for (2,5-DMF + 1-butanol or 2-butanol) systems. The negative values of deviations in isentropic compressibility, Δκ_s, indicate that there is strong unlike dipole–dipole interaction in the mixtures which compensates greater to the positive contribution to Δκ_s arising from the mutual rupturing of the dipolar aggregates in components 1 and 2 by each other [71]. The positive values of Δκ_s may be due to rupture of hydrogen bonded associates of 1-butanol or 2-butanol dominated over hydrogen bonding between unlike molecules.

Fig. 2

Plot of deviation in isentropic compressibility,Δκ_s, for the binary mixtures: (a) {2,5-DMF (1)+FA (2)}; (b) {2,5-DMF (1)+MIBK (2)}; (c) {2,5-DMF (1)+1-butanol (2)} and (d) {2,5-DMF (1)+2-butanol (2)} as function of the composition expressed in the mole fraction at 293.15 K (♦); 303.15 K (■); 313.15 K (▲) and 323.15 K (●). The dotted lines were generated using Redlich-Kister polynomial curve-fitting.

3.5 Correlation of derived properties

Experimental excess/deviation properties of the {2,5-dimethylfuran (DMF)+FA or 1-butanol or 2-butanol, or MIBK} were correlated by Redlich–Kister Equation (4): $X = x_{1} x_{2} \sum_{i = 1}^{k} A_{i} {({1 - 2 x}_{1})}^{i - 1}$ (4) where X is excess molar volumes, $V_{m}^{E}$ and deviation in isentropic compressibility, Δκ_s. The values of the fitting parameters A_i have been evaluated using a least-square method. These results are summarized in Table 4, together with the corresponding standard deviations, σ, which was determined using Equation (5): $σ (X) = {[\frac{{\sum_{i = 1}^{N} (X_{\exp t} - X_{c a l c})}^{2}}{(N - k)}]}^{1 / 2}$ (5)where N is the number of experimental points and k is the number of coefficients used in the Redlich-Kister equation. The values of $V_{m}^{E}$ and Δκ_s as well as the plots of the Redlich-Kister model are displayed in Figures 1 (a)–(d) and 2 (a)–(d), respectively. The standard deviations, between the experimental data and those calculated using Redlich–Kister equation are also given in Table 4, show very small values at the investigated temperatures for all the systems.

Table 4

Coefficients A_i, and standard deviations obtained for the binary systems studied in this work at different temperatures and at pressure p = 0.1 MPa for the Redlich–Kister equation.

4 Conclusion

In this work, density and speed of sound of {2,5-dimethylfuran (DMF) + FA or 1-butanol or 2-butanol, or MIBK} systems were measured over the temperature range of 293.15–323.15 K and at atmospheric pressure. The experimental values were used to calculate the excess functions, which were then correlated using a Redlich-Kister-type polynomial equation. The excess molar volumes were negative for {2,5-dimethylfuran (DMF)+F) or MIBK} systems and positive for {2,5-dimethylfuran (DMF)+1-butanol or 2-butanol} systems; deviations in isentropic were negative for (2,5-DMF+MIBK) binary system, and both positive and negative for the system (2,5-DMF+FA). The positive values of Δκ_s are also observed for (2,5-DMF+1-butanol or 2-butanol) systems.

Supplementary Material

Download PDF file.

Supplementary figures and tables.

References

Annual Energy Outlook (2013) The U.S. Energy Information Administration (EIA), Washington, DC. [Google Scholar]
Huber G.W., Iborra S., Corma A. (2006) Synthesis of transportation fuels from biomass: chemistry, catalysts, and engineering, Chem. Rev. 106, 4044–4098. [CrossRef] [PubMed] [Google Scholar]
Alonso D.M., Bond J.Q., Dumesic J.A. (2010) Catalytic conversion of biomass to biofuels, Green Chem. 12, 1493–1513. [Google Scholar]
Wilson K., Lee A.F. (2013) Heterogeneous Catalysts for Clean Technology: Design, Analysis and Application, first ed. Wiley-VCH, Weinheim, Germany. [Google Scholar]
Van Putten R.J., Van der Waal J.C., de Jong E., Rasrendra C.B., Heeres H.J., de Vries J.G. (2013) Hydroxymethylfurfural, A versatile platform chemical made from renewable resources, Chem. Rev. 113, 1499–1597. [Google Scholar]
Mejia A., Oliveira M.B., Segura H., Cartes M., Coutinho J.A.P. (2013) Isobaric vapor-liquid equilibrium and isothermal surface tensions of 2,2′-oxybis[propane]+2,5-Dimethylfuran, Fluid Phase Equilib. 345, 60–67. [Google Scholar]
Mejia A., Segura H., Cartes M., Coutinho J.A.P. (2012) Vapor-liquid equilibrium, densities, and interfacial tensions of the system hexane+2,5-dimethylfuran, J. Chem. Eng. Data 57, 2681–2688. [Google Scholar]
Verevkin S.P., Welle F.M. (1998) Thermochemical studies for determination of the standard molar enthalpies of formation of alkyl-substituted furans and some ethers, Struct. Chem. 9, 215–221. [Google Scholar]
Mejía A., Segura H., Cartes M. (2014) Experimental determination and theoretical prediction of the vapor-liquid equilibrium and interfacial tensions of the system methyl-tert-butyl ether+2,5-dimethylfuran, Fuel 116, 183–190. [CrossRef] [Google Scholar]
Mejía A., Segura H., Cartes M. (2013) Isobaric vapor-liquid equilibrium and isothermal interfacial tensions for the system ethanol+2,5-Dimethylfuran, J. Chem. Eng. Data 58, 3226–3232. [Google Scholar]
da Silva J.L., Aznar M. (2014) Thermophysical properties of 2,5-dimethylfuran and liquid-liquid equilibria of ternary systems water+2,5-dimethylfuran+alcohols (1-butanol or 2-butanol or 1-hexanol), Fuel 136, 316–325. [CrossRef] [Google Scholar]
Orem H., Sur S.K. (1989) Can. J. Chem. 67 65–85. [Google Scholar]
Riddick J.A., Bringer W.B. (1970) Organic Solvents, 3rd Edn. Wiley, New York [Google Scholar]
Zorebski E., Waligora A. (2008) Densities, excess molar volumes, and isobaric thermal expansibilities for 1,2-ethanediol+1-butanol, or 1-hexanol, or 1-octanol in the temperature range from (293.15 to 313.15) K, J. Chem. Eng. Data 53, 591–595. [Google Scholar]
Bahadur I., Deenadayalu N., Tywabi Z., Sen S., Hofman T. (2012) Volumetric properties of ternary (IL+2-propanol or 1-butanol or 2-butanol+ethyl acetate) systems and binary (IL+2-propanol or 1-butanol or 2-butanol) and (1-butanol or 2-butanol+ethyl acetate) systems, J. Chem. Thermodyn. 49, 24–38. [Google Scholar]
Riddick J.A., Bunger W.B., Sakano T.K. (1986) Organic solvents: Physical properties and methods of purification, fourth ed., Wiley, New York. [Google Scholar]
Iglesias M., Orge B., Tojo J. (1996) Refractive indices, densities and excess properties on mixing of the systems acetone+methanol+water and acetone+methanol+1-butanol at 298.15 K, Fluid Phase Equilib. 126, 203–223. [Google Scholar]
Riddick J, Bunger W, Sakano T.K. (1986) Organic Solvents, Wiley/Interscience, New York [Google Scholar]
Mokhtarani B., Sharifi A., Mortaheb H.R, Mirzaei M., Mafi M., Sadeghian F. (2009) Density and viscosity of pyridinium-based ionic liquids and their binary mixtures with water at several temperatures, J. Chem. Thermodyn. 41, 1432–1438. [Google Scholar]
Aminabhavi T., Benerjee K. (1998) Density, viscosity, refractive index, and speed of sound in binary mixtures of 2-Chloroethanol with Alkanols (C1−C6) at 298.15, 303.15, and 308.15 K, J. Chem. Eng. Data 43, 509–513. [Google Scholar]
VIJayalakrhml T.S., NaMu P.R. (1992) Excess volumes of binary mixtures of 1, 2, 4-trichlorobenzene with 1–Aikanois, J. Chem. Eng. Data, 37, 366–369. [Google Scholar]
Thermodynamic Tables-Non-hydrocarbons; Thermodynamics Research Center, The Texas ABM University System: College Station, TX (loose-leaf data sheets, extant1988, pd-5000). [Google Scholar]
Torres G., Apesteguı́a C.R., Di Cosimo J.I. (2007) Volumetric properties of binary mixtures of acetonitrile and alcohols at different temperatures and atmospheric pressure, J. Mol. Liq. 131–132, 139–144. [Google Scholar]
CRC Handbook of Chemistry and Physics, (2004–2005) 85th Edition CRC PRESS. Inc. [Google Scholar]
Zaoui-Djelloul-Daouadji M., Bendiaf L., Bahadur I., Negadi A., Ramjugernath D., Ebenso E.E., Negadi L (2015) Volumetric and acoustic properties of binary systems (furfural or furfuryl alcohol+toluene) and (furfuryl alcohol+ethanol) at different temperatures, Thermochim. Acta 611, 47–55. [Google Scholar]
Lomba L, Giner B., Bandres I., Lafuente C., Pinoa M.R. (2011) Physicochemical properties of green solvents derived from biomass, Green Chem. 13, 2062–2070. [Google Scholar]
Tai W.-P., Lee H.-Y., Lee M.-J. (2014) Isothermal vapor-liquid equilibrium for binary mixtures containing furfural and its derivatives, Fluid Phase Equilib. 384, 134–142. [Google Scholar]
Flick E.W. (1998) Industrial Solvents Handbook, 5th ed., Noyes Data Corporation, Westwood, New Jersey, U.S.A, pp. 340. [Google Scholar]
Naorem H., Suri S.K. (1993) Molar excess volumes of furfuryl alcohol and aromatic hydrocarbons at 25 °C, J. Solution Chem. 22, 183–189. [Google Scholar]
Martínez N.F., Lladosa E., Burguet M., Montón J.B., Yazimon M. (2009) Isobaric vapour-liquid equilibria for the binary systems 4-methyl-2-pentanone+1-butanol and+2-butanol at 20 and 101.3 kPa, Fluid Phase Equilib. 277, 49–54. [Google Scholar]
TRC Thermodynamic Tables, Non-Hydrocarbons, Thermodynamics Research Center, NIST/TRC Table Database, Win Table, 2004. [Google Scholar]
Bendiaf L., Bahadur I., Negadi A., Naidoo P., Ramjugernath D., Negadi L. (2015) Effects of alkyl group and temperature on the interactions between furfural and alcohol: Insight from density and sound velocity studies, Thermochim. Acta 599, 13–22. [Google Scholar]
Nasterlack T., Blottnitz H.V., Wynberg R. (2014) Are biofuel concerns globally relevant? Prospects for a proposed pioneer bioethanol project in South Africa, Energy Sustainable Dev. 23, 1–14. [Google Scholar]
Outcalt S.L., Laesecke A., Fortin T.J. (2010) Density and speed of sound measurements of 1- and 2-butanol, J. Mol. Liq. 151, 50–59. [Google Scholar]
Wilson W., Bradley D. (1964) Speed of sound in four primary alcohols as a function of temperature and pressure, J. Acoust. Soc. Am. 36, 333–337. [Google Scholar]
Guan W., Chang N., Yang L., Bu X., Wei J., Liu Q. (2017) Determination and Prediction for the Polarity of Ionic Liquids, J. Chem. Eng. Data 62, 2610–2616. [Google Scholar]
Varfolomeev M.A., Zaitseva K.V., Rakipov I.T., Solomonov B.N., Marczak W. (2016) Speed of sound, density, and related thermodynamic excess properties of binary mixtures of 2-pyrrolidone and N-methyl-2-pyrrolidone with acetonitrile and chloroform, J. Chem. Eng. Data 61, 1032–1046. [Google Scholar]
Zorębski E., Góralski P., Godula B., Zorębski M. (2014) Thermodynamic and acoustic properties of binary mixtures of 1-butanol with 1,2-butanediol. The comparison with the results for 1,3-, and 1,4-butanediol, J. Chem. Thermodyn. 68, 145−152. [Google Scholar]
Lee K-H., Park S-J. (2017) Isothermal vapor-liquid equilibria, excess molar volume and the deviation of refractive indices for binary mixtures of 1-butanol, 1-hexanol, 3-methyl-1-butanol and butyl acetate, Fluid Phase Equilib. 436, 47−54. [Google Scholar]
Jimenez E., Casas H., Segade L., Franjo C. (2000) Surface tensions, refractive indexes and excess molar volumes of hexane+1-alkanol mixtures at 298.15 K, J. Chem. Eng. Data 45, 862–866. [Google Scholar]
Bruno F., Thiago M.W., Thiago M.C., Leonardo H., Aznar M. (2012) Experimental and calculated liquid-liquid equilibrium data for water+furfural+solvents, Fluid Phase Equilib. 334, 97–105. [Google Scholar]
Rodríguez A., Canosa J., Tojo J (2001) Density, refractive index, and speed of sound of binary mixtures (diethyl carbonate+alcohols) at several temperatures, J. Chem. Eng. Data 46, 1506–1515. [Google Scholar]
Kijevcanin M.L., Radovi I.R., Djordjevi B.D., Tasić A.Ž., Šerbanović S.P. (2011) Experimental determination and modeling of densities and refractive indices of the binary systems alcohol+dicyclohexylamine at T = (288.15–323.15) K, Thermochim. Acta 525, 114–128. [Google Scholar]
Shan Z., Asfour A.A., (1998) Viscosities and densities of eight binary 1-alkanol systems at 308.15 and 313.15 K, Fluid Phase Equilib. 143, 253–262. [Google Scholar]
TRC Thermodynamic Tables, Non-hydrocarbons, Table 23-2-1-_1, 1000.-d, Thermodynamics Research Center, College Station, TX, 1991. [Google Scholar]
Lladosa E., Chafer A., Monton J.B., Martínez N.F. (2011) Liquid−liquid and vapor−liquid−liquid equilibrium of the 4-methyl-2-pentanone+2-butanol+water system, J. Chem. Eng. Data 56, 1925–1932. [Google Scholar]
Resa J.M., González C., Juez M., Ortiz de Landaluce S. (2004) Density, refractive index and speed of sound for mixtures of ethyl acetate with 2-butanol and 3-methyl-1-butanol: Vapor–liquid equilibrium of the ethyl acetate+3-methyl-1-butanol system, Fluid Phase Equilib. 217, 175–180. [Google Scholar]
Laavi H., Zaitseva A., Pokki J., Uusi-Kyyny P., Younghun K., Ville A. (2012) Vapor-liquid equilibrium, excess molar enthalpies, and excess molar volumes of binary mixtures containing methyl isobutyl ketone (MIBK) and 2-butanol, tert-pentanol, or 2-ethyl-1-hexanol, J. Chem. Eng. Data 57, 3092–3101. [Google Scholar]
Bravo-Sanchez M., Iglesias-Silva G.A., Estrada-Baltazar A., Hall K.R., (2010) Densities and viscosities of binary mixtures of n-butanol with 2-butanol, isobutanol, and tert-butanol from (303.15 to 343.15) K, J. Chem. Eng. Data 55, 2310–2315. [Google Scholar]
Gowrisankar M., Venkateswarlu P., Kumar K.S., Sivarambabu S., (2014) J. Ind. Eng. Chem. 25, 405–418. [CrossRef] [Google Scholar]
Krishna P.M., Kumar B.R., Sathyanarayana B., Kumar K.S., Satyanarayana N. (2009) Densities and speeds of sound for binary liquid mixtures of thiolane-1,1-dioxide with butanone, pentan-2-one, pentan-3-one, and 4-methyl-pentan-2-one at T = (303.15 or 308.15 or 313.15) K, J. Chem. Eng. Data 54, 1947–1950. [Google Scholar]
Kumari P.G., Venkatesu P., Rao M.V.P, Lee M.-J., Lin H.-M. (2009) Excess molar volumes and ultrasonic studies of N-methyl-2-pyrrolidone with ketones at T = 303.15 K, J. Chem. Thermodyn. 41, 586–590. [Google Scholar]
Tiwari K., Patra C., Padhy S., Chakravortty V., (1996) Molecular interaction study on binary mixtures of dimethyl sulphoxide+isobutyl methyl ketone (IBMK),+acetylacetone and+tri-N-butylphosphate (TBP) from the excess properties of ultrasonic velocity, viscosity and density, Phys. Chem. Liq.: An Int. J. 32, 149–157. [CrossRef] [Google Scholar]
Radhamma M., Venkatesu P., Rao M.V.P., Lee M.-J., Lin H.-M, (2008) Excess molar volumes and ultrasonic studies of dimethylsulphoxide with ketones at T = 303.15 K, J. Chem. Thermodyn. 40, 492–497. [Google Scholar]
Zarei H.A. (2006) Densities and volumetric properties of methyl isobutyl ketone+alkanols (C1-C4) at different temperatures, J. Mol. Liq. 124, 23–31. [Google Scholar]
Lee L.-S., Chuang M.-L. (1997) Excess volumes of cyclohexane with 2-propanone, 2-butanone, 3-pentanone, 4-methyl-2-pentanone, 1-propanol, and 2-propanol and ethanoic Acid+1-propanol systems, J. Chem. Eng. Data 42, 850–853. [Google Scholar]
Clara R.A., Marigliano A.C.G., Solimo H.N. (2007) Density, viscosity, isothermal (vapour+liquid) equilibrium, excess molar volume, viscosity deviation, and their correlations for chloroform+methyl isobutyl ketone binary system, J. Chem. Thermodyn. 39, 261–267. [Google Scholar]
Fuge E.T.J., Bowden S.T., Jones W.J. (1952) Some physical properties of diacetone alcohol, mesityloxide and methyl isobutyl ketone, J. Phys. Chem. 56, 1013–1016. [Google Scholar]
Riggio R., Ramos J.F., Ubeda M.H., Espindola J.A. (1981) Mixtures of methyl isobutyl ketone with three butanols at various temperatures, Can. J. Chem. 59, 3305–3308 [Google Scholar]
K. Raznjevic (1976) Handbook of thermodynamic tables and charts. McGraw-Hill book co. Inc. [Google Scholar]
Weisberger A, Proskanes E.D., Reddick, T.A., Toops E.E. (1955) Organic Solvents. Inter. Science Inc. New York. [Google Scholar]
Dakshinamurty P., Rao G.J., Acharya M.V.R., Rao C.V. (1958) Ternary vapour-liquid equilibria in the system: benzene-cyclohexane-methyl isobutyl ketone, Chem. Eng. Sci. 9, 69–73. [Google Scholar]
Joshi D., Bhatnager D., Kumar A., Gupta R, (2009) Direct measurement of acoustic impedance in liquids by a new pulse echo technique, J. Metro. Soc. India, 24, 215–224. [Google Scholar]
Venkatesu P., Rao M.V.P. (1997) Ultrasonic studies of binary mixtures of N, N-dimethylformamide with ketones at 303.15 K, Indian J. Pure Appl. Phys. 35, 62–64. [Google Scholar]
Ouaar F., Negadi A., Bahadur I., Negadi L. (2017) Thermophysical approach to understand the nature of molecular interactions and structural factor between methyl isobutyl ketone and organic solvents mixtures, J. Chem. Thermodyn. 113, 291–300. [Google Scholar]
Chauhan R.K., Mehta S.K. (1996) Ultrasonic velocity and apparent isentropic compressibilities in mixtures of nonelectrolytes, J. Solution Chem. 26, 295–308. [Google Scholar]
Dewan R.K., Gupta C.M., Mehta S.K. (1988) Ultrasonic study of (ethylbenzene+n-alkanol), Acta Acust. United Ac. 65, 245–253. [Google Scholar]
Eyring H., Kincaid J.F. (1938) Free volumes and free angle ratios of molecules in liquids, J. Chem. Phys. 6, 220–229. [Google Scholar]
Zafarani-Moattar M.T., Shekaari H. (2005) Apparent molar volume and isentropic compressibility of ionic liquid 1-butyl-3-methylimidazolium bromide in water, methanol, and ethanol at T = (298.15 to 318.15) K, J. Chem. Thermodyn. 37 1029–1035. [Google Scholar]
Jacobson B. (1952) Ultrasonic velocity in liquids and liquid mixtures, J. Chem. Phys. 20, 927–928. [Google Scholar]
Naorem H., Suri S.K. (1991) Thermodynamic studies on the binary liquid mixtures containing furan derivatives: Furfural+Aliphatic Ketones, J. Mol. Liq. 50, 39–52. [Google Scholar]

All Tables

Table 1

Molar mass, CAS number, suppliers and purities of chemicals used in this study.

Coefficients A_i, and standard deviations obtained for the binary systems studied in this work at different temperatures and at pressure p = 0.1 MPa for the Redlich–Kister equation.

In the text

All Figures

Les statistiques affichées correspondent au cumul d'une part des vues des résumés de l'article et d'autre part des vues et téléchargements de l'article plein-texte (PDF, Full-HTML, ePub... selon les formats disponibles) sur la platefome Vision4Press.

Les statistiques sont disponibles avec un délai de 48 à 96 heures et sont mises à jour quotidiennement en semaine.

Le chargement des statistiques peut être long.