The study of excess molar volumes and related properties for binary mixtures containing benzyl alcohol and 1,3-dichloro-2-propanol with vinyl acetate, ethyl acetate and t-butyl acetate at T = 293.15 to 313.15 K and P = 0.087 MPa

Thermochimica Acta 633 (2016) 149–160

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The study of excess molar volumes and related properties for binary mixtures containing benzyl alcohol and 1,3-dichloro-2-propanol with vinyl acetate, ethyl acetate and t-butyl acetate at T = 293.15 to 313.15 K and P = 0.087 MPa Hamid Reza Rafiee ∗ , Saeedeh Sadeghi Department of Physical Chemistry, Faculty of Chemistry, Razi University, Kermanshah 67149, Iran

a r t i c l e

i n f o

Article history: Received 9 October 2015 Received in revised form 30 March 2016 Accepted 1 April 2016 Available online 16 April 2016 Keywords: Density Benzyl alcohol Excess molar volume Excess thermal expansion Redlich-Kister equation

a b s t r a c t The density data for binary mixtures of benzyl alcohol or 1,3-dichloro-2-propanol with vinyl acetate, ethyl acetate and t-butyl acetate were measured at T = (293.15–313.15) K and P = 0.087 MPa. From these data, the excess molar volumes, partial molar volumes, excess partial molar volumes, partial molar volumes at infinite dilution, apparent molar volumes, thermal expansion coefficients and their excess values are calculated for studied binary systems. The Redlich- Kister equations were fitted to excess molar volumes data. The results show that excess molar volumes for all considered systems are negative and decrease with increasing temperature. The same behavior was observed for excess thermal expansion coefficients. The interactions between molecules in mixtures are discussed and explained based on these experimental data. © 2016 Published by Elsevier B.V.

1. Introduction The study of thermophysical properties of liquid mixtures is growing day by day since this type of considerations gives us a better understanding about interactions between molecules in mixtures. The studies on volumetric and thermodynamic properties of alcohols and esters binary mixtures are increasing [1–10]. Alcohols are identified as polar associated liquids with ability of hydrogen-bond formation while esters are known as compounds including both carbonyl and alkyl groups so that recognizing the interactions between these components in solutions are helpful to develop theories concerning our knowledge about liquid mixtures. Benzyl alcohol is used as a general solvent for inks, paints, lacquers, and epoxy resin coatings. It is also a precursor to a variety of esters, used in the soap, perfume, and flavor industries. It is also used as a photographic developer and as a bacteriostatic preservative at low concentration in intravenous medications, cosmetics and topical drugs. 1,3-dichloro-2-propanol has several applications in glycerol, celluloid and plastics production and also in

∗ Corresponding author. E-mail address: rafi[email protected] (H.R. Rafiee). http://dx.doi.org/10.1016/j.tca.2016.04.001 0040-6031/© 2016 Published by Elsevier B.V.

pharmacy. Ethyl acetate is a solvent which is used in glues, nail polish removers, decaffeinating tea and coffee, and cigarettes. Vinyl acetate is an organic compound which is the precursor to polyvinyl acetate, an important polymer in industry. Tert-butyl acetate is used as a solvent in the production of enamels, inks, adhesives, thinners and industrial cleaners. In our previous work we reported volumetric properties for binary mixtures of 1-propanol and i-butanol with vinyl, ethyl and t-butyl acetate [11]. There are rare experimental data for volumetric properties of binary mixtures including benzyl alcohol or 1,3-dichloro-2propanol with vinyl, ethyl and t-butyl acetate in the literature. So we were interesting to do this study on volumetric properties of these systems.

2. Experimental 2.1. Materials Table 1 includes the properties of used materials. All solutions were prepared afresh by mass using an analytical balance (Sartorius, CP224S, Germany) with a standard uncertainty of 10−4 g. The average uncertainty in the mole fraction of the mixtures was estimated to be less than ±0.003. Caution was taken to prevent

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Fig. 1. Deviation plot for comparison of density of pure components. Benzyl alcohol comparison with: , Ref. [11], Ref. [12], , Ref. [13], , Ref. [14]. Vinyl acetate , Ref. [18]. Ethyl acetate comparison with: , Ref. [21], , Ref. [3], , Ref. [22], ×, Ref. [23], , Ref. [6]. T-butyl acetate comparison with , Ref. [24]. comparison with: Deviations are calculated as: [(␳exp. − ␳reported ) /␳exp. ] ×100. Table 1 Provenance and mass fraction purity of the compounds studied.a compound

CAS number

supplier

Mass fraction purity (purification analysis method)

Molar mass (g.mol−1 )

Benzyl alcohol 1,3-Dichloro-2-propanol Vinyl Acetate Ethyl Acetate t-Butyl Acetate

100-51-6 96-23-1 108-05-4 141-78-6 540-88-5

Merck Merck Merck Merck Merck

>99% (GC) >99% (GC) >99% (GC) >99% (GC) >99% (GC)

108.14 128.99 86.09 88.10 116.16

a

All materials are used without further purifications.

evaporation of the sample after preparation. Measurements were performed immediately after preparation of solutions. 2.2. Apparatus Densities were measured using a U-tube vibrating densitometer (Anton Paar DMA 4500). The apparatus was calibrated with double distilled deionized and degassed water, and dry air at ambient pressure (0.087 MPa). All injections to densimeter were done by using micro syringe for afresh prepared solutions. Temperature was automatically kept constant within ±0.05 K by instrument with its built-in thermostat. All measurements were performed three times, and the reported results are the relevant averages. The apparatus is precise within 1 × 10−5 g cm−3 , its repeatability is within 3 × 10−5 g cm−3 and the uncertainty of density measurements was estimated to be better than ±1 × 10 −3 g cm−3 . 3. Results and discussion Table 2 lists the values of measured and reported densities [1–8,12–25] for pure materials. Fig. 1 shows deviation graph which compares our values with literature for density at different temperatures. Deviations are calculated using following equation: Dev% = [(␳exp − ␳exp )/␳report ] × 100

(1)

where ␳exp and ␳ report stand for measured and reported densities, respectively.

Table 2 and Fig. 1 confirm that agreement between our data and literature values within experimental uncertainty are excellent. The values of density for six binary mixtures at studied temperatures are tabulated in Tables 3–8. Densities for the pure esters are those reported in our previous work [11]. As can be seen from these tables, densities are increased with mole fraction of benzyl alcohol and/or 1,3—dichloro -2-propanol in their binary mixtures and decreased with raising temperature. This is happened because in these mixtures the mentioned alcohols are the component with larger density. Also due to increasing of volume with temperature, it is reasonable that density show decreasing with enhancing temperature. Also excess molar volumes are computed using the following equation: E Vm = ˙i

1



−

1 i



xi Mi

(2)

where  denotes density of solution, and xi ,i and Mi are the mole fraction, density and molar mass of component i. The excess molar volumes are included in Tables 3–8. The values for excess molar volumes are negative (and relatively small) for all considered mixtures over the whole range of composition and at all temperatures. This behavior is illustrated graphically in Figs. 2 and 3. Negative excess volumes usually arise from predominance of specific and attractive interactions factor to possible differences in size and shape of components in mixture (which in turn led to inadequate accommodation of molecules between each other). Interstitial accommodation that comes from changing of free volumes and formation of new polymers of ester-alcohol will lead to negative excess volumes and under these conditions contraction

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151

Table 2 Measured and reported density values for pure components at P = 0.087 MPa. components

T/K

␳/(g cm−3 ) This work

␳/(g cm−3 ) Literature

Benzyl alcohol

298.15

1.04138

303.15

1.03750

308.15

1.03363

313.15

1.02971

293.15 298.15

0.93241 [11] 0.92601 [11]

303.15 308.15 313.15 293.15 298.15

0.91956 [11] 0.91307 [11] 0.90652 [11] 0.90071 [11] 0.89465 [11]

303.15

0.88852 [11]

308.15

0.88235 [11]

313.15

0.87612 [11]

298.15 308.15

0.86141 [11] 0.85017 [11]

1.0413 [12], 1.0401 [13], 1.04164 [14], 1.041216 [15] 1.0375 [12], 1.0365 [13], 1.03742 [14], 1.037352 [15] 1.0337 [12], 1.0330 [13], 1.03384 [14], 1.033474 [15] 1.0294 [12], 1.0292 [13], 1.03043 [14], 1.029583 [15] 0.931950 [19] 0.925838 [19], 0.925775 [20], 0.92569 [21], 0.92567 [16], 0.925775 [8] 0.919089 [19] 0.912874 [19] 0.906116 [19] 0.900573 [22], 0.90100 [1] 0.894473 [22], 0.89472 [3], 0.8948 [23], 0.8944 [24], 0.8946 [6], 0.89444 [4], 0.89564 [2], 0.89434 [17], 0.89424 [18], 0.8943 [7] 0.888347 [22], 0.888555 [3], 0.8886 [23], 0.8885 [24], 0.88850 [5], 0.8885 [6] 0.882172 [22], 0.8827 [24], 0.8825 [6] 0.875951 [22], 0.87513 [3], 0.8752 [23], 0.8763 [24] 0.8611 [25] 0.8494 [25]

Vinyl Acetate

Ethyl Acetate

t-Butyl Acetate

Standard uncertainties u are u(P) = 5 kPa, u(T) = 0.05 K and combined expanded uncertainties Uc are Uc () = 1×10−3 g cm−3 , (0.95 level of confidence).

shape of alkyl part of t-butyl acetate molecule raises its packing ability between alcohol molecules in mixture and directs to extend hydrophobic interactions via alkyl group of alcohols. The argument can be confirmed by noting to relevant excess volumes for 1,3dichloro-2-propanol + t-butyl acetate which are absolutely largest in mixtures including 1,3-dichloro-2-propanol. It seems likely that in ethyl acetate + 1,3-dichloro-2-propanol mixture, structural factors restrict and rather compensate attractive interactions between unlike molecules which result to relatively lowest values for excess molar volumes and leading to nearly ideal behavior.

Fig. 2. Excess molar volume of {Benzyl alcohol + t-Butyl Acetate} plotted against mole fraction of Benzyl alcohol. T = 308.15 K, ×, T = 313.15 K.

, T = 293.15 K,

, T = 298.15 K,

, T = 303.15 K,

in volume takes place on mixing [3,26]. The effect is intense by rising temperature as can be seen from Figs. 2 and 3. Tables 3–8 show that in general the absolute values of excess molar volumes are larger for mixtures including benzyl alcohol compared to 1,3dichloro-2-propanol ones. Also the highest excess molar volumes belong to binary mixture including benzyl alcohol + t-butyl acetate whereas the least values relate to 1,3-dichloro-2-propanol + ethyl acetate. This mixture behaves nearly ideal because the excess molar volumes are relatively small (−0.21 cm3 mol−1 at 293.15 K to −0.39 cm3 mol−1 at 313.15 K for xi  0.5). The relatively large and negative excess volumes for benzyl alcohol + t-butyl acetate mixture may be attributed to specific attractive interactions between alcohol and ester molecules in mixture. Furthermore, spherical

Fig. 3. Excess molar volume of {1,3-dichloro-2-propanol + vinyl acetate}, plotted against mole fraction of 1,3-Dichloro-2-propanol. , T = 303.15 K, , T = 308.15 K, ×, T = 313.15 K.

, T = 293.15 K,

, T = 298.15 K,

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Table 3  E , thermal expansion coefficient (˛p ) and excess thermal expansion coefficient (˛Ep ) for (x benzyl alcohol + (1 − x) Vinyl Acetate) Densities (), excess molar volumes, Vm mixtures at T = (293.15–313.15) K and P = 0.087 MPa. / (g cm−3 )

E Vm / (cm3 mol−1 )

˛p / (kK−1 )

˛Ep / (kK−1 )

0.0000 0.0504 0.0954 0.1987 0.2999 0.3947 0.5005 0.5991 0.7047 0.8037 0.9067 1.0000

0.93241 [11] 0.94017 0.94704 0.96108 0.97418 0.98563 0.99761 1.00819 1.01912 1.02840 1.03737 1.04521

T = 293.15 K 0.00 −0.14 −0.27 −0.41 −0.51 −0.55 −0.54 −0.51 −0.45 −0.33 −0.16 0.00

1.388 1.327 1.272 1.197 1.110 1.046 0.978 0.920 0.864 0.819 0.776 0.741

0.000 −0.025 −0.048 −0.050 −0.068 −0.069 −0.068 −0.063 −0.053 −0.038 −0.019 0.000

0.0000 0.0504 0.0954 0.1987 0.2999 0.3947 0.5005 0.5991

0.92601 [11] 0.93420 0.94140 0.95540 0.96888 0.98052 0.99277 1.00362

T = 298.15 K 0.00 −0.15 −0.29 −0.44 −0.55 −0.58 −0.58 −0.54

1.397 1.336 1.280 1.204 1.116 1.051 0.983 0.925

0.000 −0.024 −0.048 −0.051 −0.070 −0.071 −0.069 −0.064

x 0.7047 0.8037 0.9067 1.0000

/ (g cm−3 ) 1.01477 1.02423 1.03339 1.04138

E Vm / (cm3 mol−1 ) −0.48 −0.35 −0.17 0.00

˛p / (kK−1 ) 0.868 0.822 0.779 0.744

˛Ep / (kK−1 ) −0.054 −0.039 −0.020 0.000

0.0000 0.0504 0.0954 0.1987 0.2999 0.3947 0.5005 0.5991 0.7047 0.8037 0.9067 1.0000

0.91956 [11] 0.92810 0.93570 0.94966 0.96351 0.97538 0.98791 0.99897 1.01036 1.02002 1.02937 1.03750

T = 303.15 K 0.00 −0.16 −0.31 −0.46 −0.59 −0.62 −0.62 −0.58 −0.51 −0.37 −0.19 0.00

1.407 1.345 1.288 1.211 1.122 1.057 0.988 0.929 0.872 0.825 0.782 0.747

0.000 −0.025 −0.050 −0.053 −0.072 −0.072 −0.071 −0.066 −0.055 −0.041 −0.021 0.000

0.0000 0.0504 0.0954 0.1987 0.2999 0.3947 0.5005

0.91307 [11] 0.92200 0.93000 0.94389 0.95806 0.97021 0.98301

T = 308.15 K 0.00 −0.17 −0.33 −0.49 −0.62 −0.66 −0.65

1.417 1.354 1.296 1.218 1.128 1.063 0.993

0.000 −0.026 −0.051 −0.055 −0.074 −0.074 −0.073

x 0.5991 0.7047 0.8037 0.9067 1.0000

␳/ (g cm−3 ) 0.99432 1.00595 1.01585 1.02533 1.03363

E Vm / (cm3 mol−1 ) −0.61 −0.54 −0.40 −0.20 0.00

˛p / (kK−1 ) 0.933 0.876 0.829 0.785 0.750

˛Ep / (kK−1 ) −0.068 −0.057 −0.041 −0.022 0.040

0.0000 0.0504 0.0954 0.1987 0.2999 0.3947 0.5005 0.5991 0.7047 0.8037 0.9067 1.0000

0.90652 [11] 0.91506 0.92262 0.93808 0.95257 0.96500 0.97809 0.98964 1.00151 1.01155 1.02127 1.02971

T = 313.15 K 0.00 −0.18 −0.34 −0.52 −0.66 −0.70 −0.70 −0.65 −0.58 −0.42 −0.21 0.00

1.427 1.364 1.306 1.226 1.135 1.068 0.998 0.938 0.880 0.832 0.788 0.753

0.000 −0.026 −0.051 −0.056 −0.075 −0.077 −0.075 −0.069 −0.058 −0.043 −0.022 0.000

x

E Standard uncertainties u are u(x) = 0.003, u(P) = 5 kPa, u(T) = 0.05 K and combined expanded uncertainties Uc are Uc () = 1 × 10−3 g cm−3 , Uc (Vm ) = 0.02 cm3 mol−1 , Uc(˛p ) = 0.005 kK−1 , Uc(˛Ep ) = 0.005 kK−1 (0.95 level of confidence).

H.R. Rafiee, S. Sadeghi / Thermochimica Acta 633 (2016) 149–160 Table 4 Densities (), excess molar volumes,

153

 E

Vm , thermal expansion coefficient(˛p ) and excess thermal expansion coefficient (˛Ep ) for (x benzyl alcohol + (1 − x) ethyl acetate)

mixtures at T = (293.15–313.15) K and P = 0.087 MPa.

x

/ (g cm−3 )

0.0000 0.0452 0.1047 0.2008 0.3043 0.4000 0.5017 0.6006 0.7013 0.8074 0.9042 0.9537 1.0000

0.90071 [11] 0.90904 0.91957 0.93591 0.95273 0.96750 0.98241 0.99627 1.00950 1.02300 1.03466 1.04008 1.04521

0.0000 0.0452 0.1047 0.2008 0.3043 0.4000 0.5017 x 0.6006 0.7013 0.8074 0.9042 0.9537 1.0000

0.89465 [11] 0.90311 0.91381 0.93043 0.94753 0.96253 0.97766 / (g cm−3 ) 0.99173 1.00514 1.01886 1.03064 1.03617 1.04138

0.0000 0.0452 0.1047 0.2008 0.3043 0.4000 0.5017 0.6006 0.7013 0.8074 0.9042 0.9537 1.0000

0.88852 [11] 0.89712 0.90802 0.92491 0.94229 0.95753 0.97289 0.98715 1.00077 1.01467 1.02667 1.03223 1.03750

0.0000 0.0452 0.1047 0.2008 x 0.3043 0.4000 0.5017 0.6006 0.7013 0.8074 0.9042 0.9537 1.0000

0.88235 [11] 0.89110 0.90218 0.91936 / (g cm−3 ) 0.93702 0.95249 0.96808 0.98256 0.99637 1.01047 1.02263 1.02828 1.03363

0.0000 0.0452 0.1047 0.2008 0.3043 0.4000 0.5017 0.6006 0.7013 0.8074 0.9042 0.9537 1.0000

0.87612 [11] 0.88503 0.89630 0.91377 0.93172 0.94743 0.96326 0.97795 0.99197 1.00626 1.01859 1.02432 1.02971

E / Vm (cm3 mol−1 )

T = 293.15 K 0.00 −0.15 −0.31 −0.51 −0.66 −0.73 −0.73 −0.69 −0.58 −0.44 −0.26 −0.12 0.00 T = 298.15 K 0.00 −0.16 −0.33 −0.54 −0.69 −0.76 −0.77 E Vm / (cm3 mol−1 ) −0.73 −0.61 −0.46 −0.27 −0.13 0.00 T = 303.15 K 0.00 −0.17 −0.35 −0.57 −0.73 −0.81 −0.81 −0.76 −0.64 −0.48 −0.28 −0.13 0.00 T = 308.15 K 0.00 −0.18 −0.37 −0.60 E Vm / (cm3 mol−1 ) −0.77 −0.85 −0.85 −0.80 −0.67 −0.50 −0.29 −0.14 0.00 T = 313.15 K 0.00 −0.19 −0.39 −0.64 −0.81 −0.89 −0.90 −0.84 −0.71 −0.53 −0.31 −0.15 0.00

˛p / (kK−1 )

˛Ep / (kK−1 )

1.367 1.321 1.265 1.183 1.103 1.038 0.975 0.919 0.869 0.818 0.776 0.758 0.741

0.000 −0.016 −0.033 −0.053 −0.066 −0.070 −0.069 −0.064 −0.052 −0.038 −0.022 −0.010 0.000

1.376 1.330 1.273 1.190 1.109 1.043 0.980 ˛p / (kK−1 ) 0.924 0.873 0.822 0.779 0.760 0.744

0.000 −0.016 −0.034 −0.054 −0.068 −0.072 −0.071 ˛Ep / (kK−1 ) −0.064 −0.053 −0.039 −0.023 −0.012 0.000

1.385 1.339 1.281 1.197 1.115 1.049 0.985 0.928 0.876 0.825 0.782 0.763 0.747

0.000 −0.016 −0.034 −0.055 −0.069 −0.073 −0.072 −0.066 −0.055 −0.040 −0.023 −0.012 0.000

1.395 1.348 1.289 1.204 ˛p / (kK−1 ) 1.122 1.054 0.990 0.932 0.880 0.828 0.785 0.766 0.750

0.000 −0.017 −0.036 −0.057 ˛Ep / (kK−1 ) −0.070 −0.076 −0.074 −0.068 −0.056 −0.042 −0.024 −0.013 0.000

1.405 1.357 1.298 1.211 1.128 1.060 0.995 0.937 0.884 0.832 0.788 0.769 0.753

0.000 −0.017 −0.036 −0.058 −0.073 −0.077 −0.076 −0.070 −0.058 −0.042 −0.025 −0.013 0.000

E Standard uncertainties u are u(x) = 0.003, u(P) = 5 kPa, u(T) = 0.05 K and combined expanded uncertainties Uc are Uc () = 1×10−3 g cm−3 , Uc (Vm ) = 0.02 cm3 mol−1 , Uc(˛p ) = 0.005 kK−1 , Uc(˛Ep ) = 0.005 kK−1 (0.95 level of confidence).

154 Table 5 Densities (), excess molar volumes,

H.R. Rafiee, S. Sadeghi / Thermochimica Acta 633 (2016) 149–160

 E

Vm , thermal expansion coefficient(˛p ) and excess thermal expansion coefficient (˛Ep ) for (x benzyl alcohol + (1 − x) t-butyl acetate)

mixtures at T = (293.15–313.15) K and P = 0.087 MPa. x

/ (g cm−3 )

0.0000 0.0470 0.0925 0.2017 0.3001 0.4000 0.4999 0.6002 0.7027 0.7996 0.9059 0.9528 1.0000

0.86695 [11] 0.87464 0.88220 0.90032 0.91698 0.93410 0.95170 0.96963 0.98830 1.00655 1.02681 1.03596 1.04521

0.0000 0.0470 0.0925 0.2017 0.3001 0.4000 0.4999 x 0.6002 0.7027 0.7996 0.9059 0.9528 1.0000

0.86141 [11] 0.86918 0.87683 0.89516 0.91200 0.92930 0.94708 / (g cm−3 ) 0.96517 0.98407 1.00240 1.02283 1.03206 1.04138

0.0000 0.0470 0.0925 0.2017 0.3001 0.4000 0.4999 0.6002 0.7027 0.7996 0.9059 0.9528 1.0000

0.85579 [11] 0.86368 0.87143 0.88977 0.90699 0.92447 0.94240 0.96068 0.97975 0.99824 1.01883 1.02811 1.03750

0.0000 0.0470 0.0925 0.2017 x 0.3001 0.4000 0.4999 0.6002 0.7027 0.7996 0.9059 0.9528 1.0000

0.85017 [11] 0.85815 0.86599 0.88475 / (g cm−3 ) 0.90196 0.91962 0.93773 0.95618 0.97542 0.99406 1.01482 1.02417 1.03363

0.0000 0.0470 0.0925 0.2017 0.3001 0.4000 0.4999 0.6002 0.7027 0.7996 0.9059 0.9528 1.0000

0.84449 [11] 0.85261 0.86052 0.87950 0.89690 0.91474 0.93304 0.95166 0.97106 0.98987 1.01079 1.02021 1.02971

E Vm / (cm3 mol−1 )

T = 293.15 K 0.00 −0.17 −0.33 −0.61 −0.77 −0.86 −0.88 −0.83 −0.71 −0.55 −0.28 −0.15 0.00 T = 298.15 K 0.00 −0.18 −0.35 −0.64 −0.81 −0.90 −0.93 E Vm / (cm3 mol−1 ) −0.87 −0.75 −0.57 −0.30 −0.16 0.00 T = 303.15 K 0.00 −0.20 −0.37 −0.65 −0.86 −0.95 −0.98 −0.92 −0.79 −0.60 −0.31 −0.17 0.00 T = 308.15 K 0.00 −0.21 −0.39 −0.71 E Vm / (cm3 mol−1 ) −0.91 −1.00 −1.03 −0.97 −0.83 −0.63 −0.33 −0.17 0.00 T = 313.15 K 0.00 −0.22 −0.41 −0.75 −0.96 −1.06 −1.09 −1.02 −0.87 −0.67 −0.35 −0.19 0.00

˛p / (kK−1 )

˛Ep / (kK−1 )

1.295 1.260 1.229 1.156 1.095 1.036 0.980 0.927 0.873 0.829 0.780 0.761 0.741

0.000 −0.015 −0.026 −0.049 −0.062 −0.071 −0.074 −0.071 −0.064 −0.048 −0.027 −0.013 0.000

1.304 1.268 1.236 1.163 1.101 1.042 0.985 ˛p / (kK−1 ) 0.931 0.877 0.832 0.783 0.764 0.744

0.000 −0.016 −0.027 −0.050 −0.064 −0.072 −0.075 ˛Ep / (kK−1 ) −0.073 −0.066 −0.050 −0.028 −0.014 0.000

1.312 1.276 1.244 1.170 1.107 1.047 0.990 0.936 0.881 0.835 0.786 0.766 0.747

0.000 −0.015 −0.027 −0.050 −0.065 −0.074 −0.077 −0.073 −0.067 −0.051 −0.028 −0.015 0.000

1.321 1.284 1.252 1.177 ˛p / (kK−1 ) 1.113 1.053 0.995 0.940 0.885 0.839 0.789 0.769 0.750

0.000 −0.016 −0.028 −0.051 ˛Ep / (kK−1 ) −0.067 −0.075 −0.078 −0.076 −0.068 −0.052 −0.029 −0.016 0.000

1.330 1.293 1.260 1.184 1.119 1.058 1.000 0.945 0.889 0.843 0.792 0.772 0.753

0.000 −0.016 −0.028 −0.053 −0.069 −0.077 −0.080 −0.077 −0.070 −0.053 −0.030 −0.016 0.000

E Standard uncertainties u are u(x) = 0.003, u(P) = 5 kPa, u(T) = 0.05 K and combined expanded uncertainties Uc are Uc () = 1 × 10−3 g cm−3 , Uc (Vm ) = 0.02 cm3 mol−1 , Uc(˛p ) = 0.005 kK−1 , Uc(˛Ep ) = 0.005 k K−1 (0.95 level of confidence).

H.R. Rafiee, S. Sadeghi / Thermochimica Acta 633 (2016) 149–160 Table 6 Densities (), excess molar volumes,

155

 E

Vm , thermal expansion coefficient(˛p ) and excess thermal expansion coefficient (˛Ep ) for (x 1,3-dichloro-2-propanol + (1 − x) vinyl

acetate) mixtures at T = (293.15–313.15) K and P = 0.087 MPa. x

/ (g cm−3 )

0.0000 0.0481 0.1022 0.2021 0.2995 0.3953 0.5002 0.6003 0.6999 0.8007 0.9014 0.9524 1.0000

0.93241 [11] 0.95428 0.97878 1.02342 1.06661 1.10866 1.15423 1.19718 1.23930 1.28145 1.32294 1.34343 1.36266

0.0000 0.0481 0.1022 0.2021 0.2995 0.3953 0.5002 x 0.6003 0.6999 0.8007 0.9014 0.9524 1.0000

0.92601 [11] 0.94793 0.97247 1.01718 1.06046 1.10254 1.14818 / (g cm−3 ) 1.19117 1.23334 1.27550 1.31700 1.33748 1.35674

0.0000 0.0481 0.1022 0.2021 0.2995 0.3953 0.5002 0.6003 0.6999 0.8007 0.9014 0.9524 1.0000

0.91956 [11] 0.94153 0.96608 1.01091 1.05425 1.09639 1.14209 1.18512 1.22729 1.26950 1.31100 1.33149 1.35072

0.0000 0.0481 0.1022 0.2021 x 0.2995 0.3953 0.5002 0.6003 0.6999 0.8007 0.9014 0.9524 1.0000

0.91307 [11] 0.93507 0.95968 1.00452 / (g cm−3 ) 1.04800 1.09021 1.13596 1.17904 1.22125 1.26347 1.30498 1.32546 1.34471

0.0000 0.0481 0.1022 0.2021 0.2995 0.3953 0.5002 0.6003 0.6999 0.8007 0.9014 0.9524 1.0000

0.90652 [11] 0.92857 0.95324 0.99825 1.04172 1.08396 1.12981 1.17293 1.21517 1.25741 1.29892 1.31940 1.33865

E Vm / (cm3 mol−1 )

T = 293.15 K 0.00 −0.06 −0.13 −0.21 −0.27 −0.30 −0.32 −0.31 −0.27 −0.21 −0.13 −0.05 0.00 T = 298.15 K 0.00 −0.07 −0.15 −0.24 −0.30 −0.34 −0.35 E Vm / (cm3 mol−1 ) −0.34 −0.30 −0.23 −0.14 −0.06 0.00 T = 303.15 K 0.00 −0.08 −0.16 −0.26 −0.34 −0.37 −0.39 −0.37 −0.32 −0.25 −0.15 −0.06 0.00 T = 308.15 K 0.00 −0.09 −0.18 −0.28 E Vm / (cm3 mol−1 ) −0.37 −0.41 −0.43 −0.41 −0.35 −0.27 −0.16 −0.07 0.00 T = 313.15 K 0.00 −0.10 −0.20 −0.32 −0.41 −0.45 −0.47 −0.45 −0.39 −0.30 −0.17 −0.07 0.00

˛p / (kK−1 )

˛Ep / (kK−1 )

1.388 1.348 1.305 1.231 1.167 1.114 1.058 1.013 0.974 0.938 0.908 0.895 0.881

0.000 −0.015 −0.030 −0.052 −0.066 −0.071 −0.073 −0.068 −0.057 −0.042 −0.022 −0.005 0.000

1.397 1.357 1.313 1.239 1.174 1.120 1.063 ˛p / (kK−1 1.018 0.979 0.942 0.912 0.899 0.885

0.000 −0.015 −0.031 −0.053 −0.067 −0.072 −0.075 ˛Ep / (kK−1 ) −0.069 −0.057 −0.043 −0.022 −0.010 0.000

1.407 1.366 1.322 1.246 1.181 1.126 1.069 1.024 0.983 0.947 0.916 0.903 0.889

0.000 −0.016 −0.031 −0.055 −0.069 −0.074 −0.076 −0.070 −0.059 −0.044 −0.023 −0.010 0.000

1.417 1.375 1.331 1.254 ˛p / (kK−1 ) 1.188 1.133 1.075 1.029 0.988 0.951 0.920 0.907 0.893

0.000 −0.016 −0.032 −0.056 ˛Ep / (kK−1 ) −0.070 −0.075 −0.078 −0.071 −0.060 −0.045 −0.024 −0.011 0.000

1.427 1.385 1.340 1.262 1.195 1.139 1.081 1.034 0.993 0.956 0.925 0.911 0.897

0.000 −0.016 −0.032 −0.057 −0.072 −0.077 −0.079 −0.073 −0.061 −0.045 −0.024 −0.011 0.000

E Standard uncertainties u are u(x) = 0.003, u(P) = 5 kPa, u(T) = 0.05 K and combined expanded uncertainties Uc are Uc () = 1×10−3 g cm−3 , Uc (Vm ) = 0.02 cm3 mol−1 , Uc(˛p ) = 0.005 kK−1 , Uc(˛Ep ) = 0.005 kK−1 (0.95 level of confidence).

156

H.R. Rafiee, S. Sadeghi / Thermochimica Acta 633 (2016) 149–160

Table 7 Densities (), excess molar volumes,

 E

Vm , thermal expansion coefficient(˛p )and excess thermal expansion coefficient (˛Ep ) for (x 1,3-dichloro-2-propanol + (1 − x) ethyl

acetate) mixtures at T = (293.15–313.15) K and P = 0.087 MPa. x

/ (g cm−3 )

0.0000 0.0442 0.0967 0.1971 0.3019 0.3939 0.4995 0.6006 0.6993 0.8006 0.9011 0.9530 1.0000

0.90071 [11] 0.92107 0.94513 0.99100 1.03905 1.08140 1.13018 1.17692 1.22262 1.26978 1.31679 1.34090 1.36266

0.0000 0.0442 0.0967 0.1971 0.3019 0.3939 0.4995 x 0.6006 0.6993 0.8006 0.9011 0.9530 1.0000

0.89465 [11] 0.91501 0.93912 0.98500 1.03315 1.07555 1.12435 ␳/ (g cm−3 ) 1.17110 1.21683 1.26396 1.31089 1.33499 1.35674

0.0000 0.0442 0.0967 0.1971 0.3019 0.3939 0.4995 0.6006 0.6993 0.8006 0.9011 0.9530 1.0000

0.88852 [11] 0.90902 0.93316 0.97910 1.02730 1.06964 1.11848 1.16525 1.21095 1.25807 1.30497 1.32901 1.35072

0.0000 0.0442 0.0967 0.1971 x 0.3019 0.3939 0.4995 0.6006 0.6993 0.8006 0.9011 0.9530 1.0000

0.88235 [11] 0.90288 0.92705 0.97297 / (g cm−3 ) 1.02122 1.06370 1.11258 1.15937 1.20506 1.25215 1.29900 1.32302 1.34471

0.0000 0.0442 0.0967 0.1971 0.3019 0.3939 0.4995 0.6006 0.6993 0.8006 0.9011 0.9530 1.0000

0.87612 [11] 0.89668 0.92120 0.96720 1.01541 1.05783 1.10665 1.15345 1.19914 1.24620 1.29310 1.31698 1.33865

E Vm / (cm3 mol−1 )

T = 293.15 K 0.00 −0.06 −0.11 −0.16 −0.19 −0.21 −0.21 −0.20 −0.16 −0.13 −0.09 −0.05 0.00 T = 298.15 K 0.00 −0.07 −0.12 −0.18 −0.22 −0.25 −0.25 E Vm / (cm3 mol−1 ) −0.23 −0.20 −0.15 −0.10 −0.05 0.00 T = 303.15 K 0.00 −0.09 −0.15 −0.22 −0.27 −0.29 −0.30 −0.28 −0.23 −0.18 −0.11 −0.06 0.00 T = 308.15 K 0.00 −0.10 −0.17 −0.24 E Vm / (cm3 mol−1 ) −0.30 −0.33 −0.35 −0.32 −0.27 −0.20 −0.13 −0.06 0.00 T = 313.15 K 0.00 −0.10 −0.22 −0.31 −0.37 −0.39 −0.39 −0.37 −0.31 −0.23 −0.15 −0.07 0.00

˛p / (kK−1 )

˛Ep / (kK−1 )

1.367 1.322 1.269 1.204 1.140 1.091 1.041 0.997 0.961 0.929 0.900 0.892 0.881

0.000 −0.024 −0.052 −0.070 −0.084 −0.088 −0.087 −0.082 −0.070 −0.051 −0.031 −0.013 0.000

1.376 1.331 1.277 1.211 1.146 1.097 1.047 ˛p / (kK−1 ) 1.002 0.966 0.933 0.904 0.896 0.885

0.000 −0.024 −0.053 −0.071 −0.085 −0.090 −0.088 ˛Ep / (kK−1 ) −0.083 −0.070 −0.053 −0.031 −0.013 0.000

1.385 1.340 1.285 1.218 1.153 1.103 1.052 1.007 0.970 0.937 0.908 0.900 0.889

0.000 −0.024 −0.054 −0.072 −0.086 −0.091 −0.090 −0.085 −0.072 −0.054 −0.032 −0.013 0.000

1.395 1.349 1.293 1.226 ˛p / (kK−1 ) 1.159 1.109 1.058 1.012 0.975 0.942 0.912 0.904 0.893

0.000 −0.025 −0.055 −0.073 ˛Ep / (kK−1 ) −0.089 −0.093 −0.091 −0.086 −0.073 −0.054 −0.032 −0.014 0.000

1.405 1.358 1.302 1.233 1.166 1.115 1.064 1.017 0.980 0.946 0.916 0.908 0.897

0.000 −0.025 −0.056 −0.075 −0.090 −0.095 −0.093 −0.088 −0.074 −0.056 −0.033 −0.014 0.000

E Standard uncertainties u are u(x) = 0.003, u(P) = 5 kPa, u(T) = 0.05 K and combined expanded uncertainties Uc are Uc () = 1×10−3 g cm−3 , Uc (Vm ) = 0.02 cm3 mol−1 , Uc(˛p ) = 0.005 kK−1 , Uc(˛Ep ) = 0.005 kK−1 (0.95 level of confidence).

H.R. Rafiee, S. Sadeghi / Thermochimica Acta 633 (2016) 149–160

157

Table 8  E , thermal expansion coefficient(˛p ) and excess thermal expansion coefficient (˛Ep ) for (x 1,3-dichloro-2-propanol + (1 − x) t-butyl Densities (), excess molar volumes, Vm acetate) mixtures at T = (293.15–313.15) K and P = 0.087 MPa.

x

/ (g.cm−3 )

0.0000 0.0496 0.0948 0.2007 0.3003 0.4001 0.4991 0.6003 0.7009 0.8013 0.9032 0.9507 1.0000

0.86695 [11] 0.88518 0.90223 0.94376 0.98520 1.02914 1.07536 1.12561 1.17916 1.23636 1.29889 1.32966 1.36266

0.0000 0.0496 0.0948 0.2007 0.3003 0.4001 0.4991 x 0.6003 0.7009 0.8013 0.9032 0.9507 1.0000

0.86141 [11] 0.87967 0.89670 0.93826 0.97970 1.02363 1.06984 / (g cm−3 ) 1.12005 1.17355 1.23068 1.29307 1.32378 1.35674

0.0000 0.0496 0.0948 0.2007 0.3003 0.4001 0.4991 0.6003 0.7009 0.8013 0.9032 0.9507 1.0000

0.85579 [11] 0.87408 0.89114 0.93270 0.97418 1.01809 1.06427 1.11446 1.16790 1.22495 1.28722 1.31785 1.35072

0.0000 0.0496 0.0948 0.2007 x 0.3003 0.4001 0.4991 0.6003 0.7009 0.8013 0.9032 0.9507 1.0000

0.85017 [11] 0.86847 0.88554 0.92712 / (g cm−3 ) 0.96860 1.01251 1.05868 1.10883 1.16221 1.21917 1.28134 1.31190 1.34471

0.0000 0.0496 0.0948 0.2007 0.3003 0.4001 0.4991 0.6003 0.7009 0.8013 0.9032 0.9507 1.0000

0.84449 [11] 0.86283 0.87990 0.92151 0.96300 1.00691 1.05306 1.10317 1.15649 1.21337 1.27542 1.30591 1.33865

E / Vm (cm3 mol−1 )

T = 293.15 K 0.00 −0.09 −0.17 −0.29 −0.36 −0.39 −0.38 −0.34 −0.29 −0.21 −0.12 −0.06 0.00 T = 298.15 K 0.00 −0.10 −0.18 −0.32 −0.41 −0.44 −0.43 E Vm / (cm3 mol−1 ) −0.39 −0.33 −0.24 −0.13 −0.07 0.00 T = 303.15 K 0.00 −0.12 −0.21 −0.36 −0.46 −0.50 −0.49 −0.44 −0.37 −0.27 −0.15 −0.08 0.00 T = 308.15 K 0.00 −0.13 −0.23 −0.39 E Vm / (cm3 mol−1 ) −0.51 −0.55 −0.54 −0.49 −0.41 −0.30 −0.17 −0.09 0.00 T = 313.15 K 0.00 −0.14 −0.25 −0.44 −0.56 −0.61 −0.60 −0.55 −0.46 −0.34 −0.19 −0.10 0.00

˛p / (kK−1 )

˛Ep / (kK−1 )

1.295 1.263 1.237 1.179 1.127 1.081 1.037 0.997 0.962 0.930 0.903 0.893 0.881

0.000 −0.017 −0.029 −0.054 −0.072 −0.081 −0.087 −0.085 −0.075 −0.059 −0.033 −0.016 0.000

1.304 1.271 1.245 1.186 1.133 1.086 1.042 ˛p / (kK−1 ) 1.002 0.966 0.934 0.907 0.897 0.885

0.000 −0.018 −0.030 −0.055 −0.074 −0.084 −0.089 ˛Ep / (kK−1 ) −0.087 −0.077 −0.060 −0.033 −0.017 0.000

1.312 1.279 1.252 1.193 1.139 1.092 1.048 1.007 0.971 0.939 0.911 0.901 0.889

0.000 −0.018 −0.031 −0.055 −0.075 −0.085 −0.090 −0.088 −0.078 −0.060 −0.034 −0.017 0.000

1.321 1.287 1.260 1.200 ˛p / (kK−1 ) 1.146 1.098 1.053 1.012 0.976 0.943 0.915 0.906 0.893

0.000 −0.019 −0.032 −0.057 ˛Ep / (kK−1 ) −0.076 −0.087 −0.092 −0.089 −0.079 −0.062 −0.035 −0.016 0.000

1.330 1.296 1.268 1.208 1.153 1.104 1.059 1.017 0.981 0.948 0.920 0.910 0.897

0.000 −0.025 −0.056 −0.075 −0.090 −0.095 −0.093 −0.088 −0.074 −0.056 −0.033 −0.014 0.000

E Standard uncertainties u are u(x) = 0.003, u(P) = 5 kPa, u(T) = 0.05 K and combined expanded uncertainties Uc are Uc () = 1 × 10−3 g cm−3 , Uc (Vm ) = 0.02 cm3 mol−1 , Uc(˛p ) = 0.005 kK−1 , Uc(˛Ep ) = 0.005 kK−1 (0.95 level of confidence).

(4)

A3

 12

The apparent molar volumes V m,i also are calculated by applying excess molar volumes Vm E and using the following Eq. [28]: ϕ

Vm,1 = V1∗ + ϕ

Vm,2 = V2∗ +

E Vm x1

(9)

E Vm 1 − x1

(10)

The values for apparent molar volumes and also partial molar volumes along with their excess values are reported in supplementary Tables S1–S6. We also calculated partial molar volumes at infinite dilution, ∞ and V ¯ ∞ excess partial molar volumes at infinite dilution, V¯ E∞ V¯ m,1 m,2 m,1 which are reported in supplementary Table S7. The equations we used to do these calculations are as: ∞ V¯ m,1 = V1∗ +

j 

Ai

(11)

Ai (−1)i

(12)

i=0

∞ V¯ m,2 = V2∗ +

j  i=0

E∞ ∞ V¯ m,i = V¯ m,i − Vi∗

(13)

The Ai are Redlich-Kister coefficients and V∗ i denotes pure molar volume of component i. The signs of excess values in Table S7 are in accord with excess molar volumes of related solutions. In all cases the partial molar

−0.0001393 −0.0001109 −0.0004702 −0.00009218 −0.001764 −13.17 0.07291 0.06328 0.2803 0.01653 1.055 0.08798 – −0.0001741 −0.0001073 −0.0004124 −0.0001143

b2 a2

−10.31 −9.281 −41.95 −2.502 −158.1 −13.17 0.00009182

c1 b1

(8)

−0.06382 −0.009312 0.1006 0.06003 0.2414 0.06486

E = V¯ m,i − Vi∗ V¯ m,i

(7)

10.56 2.343 −14.87 −8.349 −35.47 −9.692

Ai i (1 − 2x1 )i−1

a1

Ai (1 − 2x1 )i + 2x12 (1 − x1 )

– – – – – –

i=0

c0

i=1

j

(6)

b0

Ai i (1 − 2x1 )i−1

V¯ m,2 = V2 ∗ + x12

j

Ai (1 − 2x1 )i – 2x1 (1 − x1 )2

−0.03115 −0.03277 −0.04081 −0.03047 −0.3623 −0.04383

i=1

i=0

a0

j

j

A2

V¯ m,1 = V1 ∗ + (1 − x1 )2

A1

where P is the number of parameters and N is the number of experimental data. Based on the values of these coefficients and using the values of V1 ∗ , V2 ∗ (pure components molar volumes) and Eqs. (6)–(8) [28]. we computed partial molar volumes V¯ m,i and partial excess molar E for each component: volumes V¯ m,i

c2

(5)

N−P

A0

i=1

␴=

E − VE Vexp calc

Table 9 Temperature dependence of Ai of Eq. (3) for excess molar volume, Vm E , with standard deviations, , for binary mixtures at various temperatures. .

 N 

b3

The coefficients of Eq. (4) and corresponding standard deviations, , obtained from least-squares fitting are given in Table 9. The standard deviations have been determined using the following relation:

a3

Ai = ai + bi T + ci T 2 i = 1, 2, 3

c3

where the coefficients Ai for Vm E have temperature dependency as following:

0.0009264 0.0003103 0.0002953 −0.0002885 0.00008802 0.00007018

(3)

i=0

−0.5441 −0.1847 −0.1829 0.1731 −0.06747 −0.04682

Ai (1 − 2x1 )i

6.945 6.688 8.458 7.678 9.791 11.33

P 

Benzyl alcohol+ Vinyl acetate Benzyl alcohol+ Ehyl acetate Benzyl alcohol + t-Butyl acetate 1,3-Dichloro-2-propanol + Vinyl acetate 1,3-Dichloro-2-propanol + Ethyl acetate 1,3-Dichloro-2-propanol + t-Butyl acetate

E Vm = x1 x2

␴

Excess molar volumes also were fitted by Redlich-Kister [27] polynomial equation:

0.002 0.002 0.003 0.001 0.001 0.002

H.R. Rafiee, S. Sadeghi / Thermochimica Acta 633 (2016) 149–160

81.82 27.64 28.23 −26.04 12.71 7.934

158

H.R. Rafiee, S. Sadeghi / Thermochimica Acta 633 (2016) 149–160

159

Fig. 4. Excess thermal expansion coefficient of {Benzyl alcohol + t-Butyl Acetate} plotted against mole fraction of Benzyl alcohol.

, T = 293.15 K,

, T = 313.15 K.

volumes at infinite dilution are lesser than pure molar volumes and are in agreement with their negative excess molar volumes. We also considered the temperature dependency of solution densities to calculate thermal expansion coefficient ˛p and then evaluate the excess thermal expansion coefficient ˛Ep . It is done by fitting a linear equation to experimental densities in each mole fraction and also using the following equations [28,29]:  = a + bT ˛p =

i =

−1 



∂ ∂T

xi Vi∗

2

x V∗ i=1 i i



(14)



(15) p

Fig. 5. Excess thermal expansion coefficient of {1,3-dichloro-2-propanol + vinyl acetate plotted against mole fraction of 1,3-dichloro-2-propanol. , T = 313.15 K.

, T = 293.15 K,

4. Conclusion In this work we considered volumetric properties of six binary mixtures including benzyl alcohol and/or 1,3 dichloro-2-propanol with vinyl, ethyl and t-butyl acetate. Densities were measured over temperature range (293.15–313.15) K and at constant pressure of 0.087 MPa. All mixtures showed negative excess volumes which are attributed to dominance of attractive interactions to structural factors. Also thermal expansion coefficients and their relevant excess values are appraised. The excess thermal expansion coefficients were negative over whole range of composition.

(16) Appendix A. Supplementary data

2

˛ideal =

i ˛∗i

(17)

i=1

˛Ep

= ˛p − ˛ideal

(18)

In these equations, a and b are constants,  is density of solution, xi is mole fraction, ϕi is volume fraction and Vi ∗ , ␣∗ i denote molar volume and thermal expansion coefficient for pure component i, respectively. At first, for each mole fraction, we calculated temperature dependency of solution density, that is (∂/∂T)P , then by dividing to minus  we appraised ˛p . The computed values for ˛p and ˛Ep in each mole fraction and temperature are also listed in Tables 3–8 for studied systems. Our values for ˛p of ethyl acetate are 1.376–1.405 kK−1 in temperatures (298.15–313.15)K which are in good agreement with those reported by Oswal and Putta [3] which are 1.377–1.421 kK−1 . Also for vinyl acetate our values are 1.388–1.427 kK−1 for temperatures (293.15–313.15) K which are in excellent agreement with values of Ref. [19] that is 1.387–1.427 kK−1 . For benzyl alcohol our values for temperature range of (298.15–313.15) K are 0.744–0.753 kK−1 which shows good agreement with reports of Ref. [12,15] and are different with reports of Ref. [13,14]. These differences come from differences in densities and densities reported especially in Ref. [13] are in general lower than ours. Figs. 4 and 5 demonstrate the behavior of ˛Ep versus mole fraction and its change with temperature for considered systems. Figures show that for six binary mixtures the excess thermal expansion coefficients are negative over whole range of composition and are almost insensitive to changing temperature. Negative ˛Ep values are assigned to formation of new interactions between unlike molecules in mixture [13,30].

Supplementary data associated with this article can be found, in the online version, at http://dx.doi.org/10.1016/j.tca.2016.04.001. References [1] A. Qin, D.E. Hoffman, P. Munk, Excess volumes of mixtures of some alkyl esters and ketones with alkanols, Collect. Czech. Chem. Commun. 58 (1993) 2625–2641. [2] S. Canzonieri, A. Camacho, R. Tabarrozzi, M. Postigo, L. Mussari, Volumetric and viscous behaviour of the binary and ternary systems formed by methyl acetate ethyl acetate and 1-propanol at 283.15, 298.15 and 313.15 K, Phys. Chem. Liq. 50 (2012) 530–545. [3] S.L. Oswal, S.S.L. Putta, Excess molar volumes of binary mixtures of alkanols with ethyl acetate from 298.15 to 323.15 K, Thermochim. Acta 373 (2001) 141–152. [4] A. Mariano, M. Postigo, H. Artigas, J. Pardo, F.M. Royo, Densities and viscosities of the ternary mixture (benzene + 1-propanol + ethyl acetate) at 298.15 K, Phys. Chem. Liq. 38 (2000) 567–581. [5] S.L. Oswal, N.Y. Ghaelb, R.L. Gardas, Volumetric and transport properties of ternary mixtures containing 1-propanol + ethyl ethanoate + cyclohexane or benzene at 303.15 K: experimental data, correlation and prediction by ERAS model, Thermchim. Acta 484 (2009) 11–21. [6] P.S. Nikam, T.R. Mahale, M. Hasan, Density and viscosity of binary mixtures of ethyl acetate with methanol, ethanol propan-1-ol, propan-2-ol, butan-1-ol, 2-methylpropan-1-ol, and 2-methylpropan-2-ol at (298.15, 303.15, and 308.15) K, J. Chem. Eng. Data 41 (1996) 1055–1058. [7] J.M. Resa, J.M. Goenaga, J. Lanz, Vapor-liquid equilibrium of binary mixtures containing ethyl acetate + 2-methyl-1-propanol and ethyl acetate + 2-methyl-1-butanol at 101.3 kPa, J. Chem. Eng. Data 51 (2006) 595–598. [8] R.D. Peralta, R. Infante, G. Cortez, A. Cisneros, Density excess volumes, and partial volumes of the binary systems of ethenyl ethanoate 1-butanol, 2-butanol, 2-methyl-1-propanol, and 2-methyl-2-propanol at 298.15 K, Chem. Eng. Commun. 192 (2005) 1684–1694. [9] A.K. Nain, T. Srivastava, J.D. Pandey, S. Gopal, Densities,ultrasonic speeds and excess properties of binary mixtures of methyl acrylate with 1-butanol, or 2-butanol, or 2-methyl-1-propanol, or 2-methyl-2-propanol at temperatures from 288.15–318.15 K, J. Mol. Liq. 149 (2009) 9–17.

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