Journal of Molecular Liquids 181 (2013) 17

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Journal of Molecular Liquids

journal homepage: www.elsevier.com/locate/molliq

Surface study of binary mixtures containing chlorinated and oxygenated compounds

D. Montao a, B. Giner b, S. Martn c, Carlos Lafuente c,
a
b
c

Departamento de Quimica, Centro de Investigacion y de Estudios Avanzados del Instituto Politecnico Nacional, Apartado Postal 14-740, 07000 Mexico, D.F, Mexico
Facultad de Ciencias de la Salud, Universidad San Jorge, Villanueva de Gallego, 50830 Zaragoza, Spain
Departamento de Qumica Fsica, Facultad de Ciencias, Universidad de Zaragoza, Ciudad Universitaria, 50009 Zaragoza, Spain

a r t i c l e

i n f o

Article history:
Received 7 January 2013
Received in revised form 28 January 2013
Accepted 31 January 2013
Available online 21 February 2013
Keywords:
Surface tension
Isomeric chlorobutanes
Butyl ethyl ether
Diisopropyl ether
Surface compositions

a b s t r a c t
We report in this work, experimental surface tensions for binary mixtures of isomeric chlorobutanes with
butyl ethyl ether or diisopropyl ether from T = 283.15 K to 303.15 K measured with a drop volume tensiometer. The surface tension data have been correlated with a RedlichKister type equation. More information
about the surface behaviour can be obtained combining these results with previously reported VLE measurements to calculate the excess surface composition of ether in the mixture. Finally, the results have been compared to the predictions obtained using a group contribution method.
2013 Elsevier B.V. All rights reserved.

1. Introduction
In the last few years, our research group has been carrying out a
comprehensive thermodynamic study about mixtures formed by
chlorobutanes and ethers [14] in order to go deeply into the effect
of energetic and structural factors in their behaviour. Moreover, the
study of ether mixtures is important since oxygenated compounds
are added to improve the octane rating and the pollution-reducing
capability of gasoline [510].
The main aim of this work is to study the surface behaviour of
mixtures formed by several haloalkanes and several ethers. For this
purpose, we have used surface tension and several derived properties
to get the molecular information related to the surface behaviour and
the adsorption phenomenon that is carried out during the mixture
process.
The study of the surface behaviour of a mixture has been used so to
get information about the molecular adsorption process of the components of a mixture [1114]. It is also well known that surface tension
of a substance can be related to the extent of the intermolecular interactions of the molecules of the substance: molecules tend to stay in the
bulk of the system due to the increase of their energy when they are
in the surface. The more and stronger intermolecular interactions between molecules, the steeper is the tendency and higher values of surface tension the substance presents. Furthermore, if a mixture is under
study instead of a pure substance, there is a different distribution of
the molecules in the surface, and an adsorption phenomenon appears.
Corresponding author. Tel.: +34 976762295.
E-mail address: celadi@unizar.es (C. Lafuente).
0167-7322/$ see front matter 2013 Elsevier B.V. All rights reserved.
http://dx.doi.org/10.1016/j.molliq.2013.01.024

The distribution of the molecules in the surface can be quantied

through surface excess concentration. Exploring the behaviour of surface tension and the excess surface concentration of a mixture, information about the extent of weakening of the intermolecular properties of
the pure components due to the mixture process and the formation of
new ones between the different components of the mixture can be
obtained as well as how the adsorption process has been carried out
and the amount of molecules of each component migrated to the surface. Due to the nature of the compounds this study will also give
some insights into the dipoledipole intermolecular interaction between of the compounds of the mixture and the specic donoracceptor
interactions between the chlorine and oxygen atoms.
This work reports experimental results of surface tensions
for some binary mixtures containing an isomeric chlorobutane:
1-chlorobutane, 2-chlorobutane, 2-methyl-1-chloropropane or 2methyl-2-chloropropane and butyl ethyl ether or diisopropyl ether
measured with a drop volume tensiometer in the temperature
range (283.15313.15) K. Combining the surface tension values
with vaporliquid equilibrium results excess surface concentrations
were also calculated in the temperature range (288.15308.15) K.
Finally, using our experimental data we have checked the accuracy
in the prediction of surface tensions of a group-contribution method
[15]. This method combines the Sprow and Prausnitz model for the description of surface tensions of liquid mixtures [16] with a group contribution method for the calculation of activity coefcients [17]. This
method has been used to predict the surface behaviour of binary and
multicomponent mixtures with satisfactory results [1824].
As far as we know, there are not references in the literature about
the surface tensions for these systems.

D. Montao et al. / Journal of Molecular Liquids 181 (2013) 17

Table 1
Surface tension, , of the pure compounds and comparison with literature data at T = 298.15 K.
Compound

1-Chlorobutane
2- Chlorobutane
1-Chloro-2-methylpropane
2-Chloro-2-methylpropane
Butyl ethyl ether
Diisopropyl ether
b
c

283.15

288.15

293.15

298.15

exptl

exptl

exptl

exptl

lit

24.83
23.79
23.83
20.75
21.95
18.51

24.34
23.01
22.99
20.10
21.43
18.12

23.74
22.29
22.31
19.62
20.96
17.74

23.29
21.83
21.80
18.92
20.42
17.34

23.10

21.40

20.25
17.31

303.15

308.15

313.15

exptl

exptl

exptl

22.69
21.18
21.08
18.45
19.92
16.97

22.16
20.43
20.23
17.82
19.44
16.58

21.55
19.43
19.23
16.98
18.98
16.16

Ref. [27].
Ref. [28].
Ref. [6].

2. Experimental section
The chemicals employed were 1-chlorobutane, 2-chlorobutane,
2-methyl-2-chloropropane, butyl ethyl ether and diisopropyl ether
(mass fraction > 0.99) obtained from Aldrich and 2-methyl-1chloropropane (mass fraction > 0.99) provided by Fluka. No additional purication has been carried out.
The surface tension of the pure liquids and their corresponding
mixtures were measured with a drop volume tensiometer Lauda
TVT-2 [25] with an uncertainty of 0.01 mN.m 1. The temperature
was kept constant within 0.01 K by means of an external Lauda
E-200 thermostat. The surface tension, , is calculated from the determined drop volume, V, using the following equation:

gV
2r cap f

25
T = 283.15 K

24

23

/ mNm

where is the density difference of the two adjacent phases, g is the

acceleration constant, rcap is the outer radius of the capillary and the
function f denotes a correction function necessary to relate the surface tension to the volume of the detached drop [25]. The proper operation of the device was satisfactorily checked by measuring the
surface tension of water.
The densities of the pure compounds and mixtures were obtained
from interpolation of our previous density measurements [4,26].
The surface tensions of the pure compounds at working temperatures together with literature values at T = 298.15 K [6,27,28] are
shown in Table 1.
All mixtures were prepared by mass using a Sartorius CP225D precision balance with an uncertainty of 1 10 5 g, the corresponding
uncertainty of the mole fraction calculated is estimated to be better
than 10 4.

The main feature of these systems is that the surface tension deviation, that is the deviation of surface tension behaviour with respect to a
lineal composition dependence is negative, although for the system
2-chloro-2-methylpropane+butyl ethyl ether this deviation is slightly
positive. There is a signicant difference between the systems containing
one or another oxygenated compound; the magnitude of this deviation is
higher in absolute value for the mixtures containing the ether with lower
surface tension, that is diisopropyl ether. On the other hand, among the
isomeric chlorobutanes the surface tension deviation is higher in absolute
vale for the mixtures formed by 1-chlorobutane, which shows the higher
surface tension. With respect to the temperature dependence of the surface tension deviation, its value decrease with temperature except for the
mixtures containing 2-chloro-2-methylpropane. It can be also outlined as
the presence of negative aneotropes [29], negative surface azeotropy, for
some of the mixtures containing diisopropyl ether, at low temperatures
for the mixtures containing 1-chlorobutane, 2-chlorobutane or 1-chloro2-methylpropane and at high temperatures for the mixture involving
2-chloro-2-methylpropane. Information about composition and surface
tension of the aneotropes is summarized in Table 3.

-1

/mN m1 at T/K

3. Results and discussion

22

The surface tension values of all the mixtures studied in this work
from T = 283.15 K to 313.15 K can be found in the supplementary
material. The surface tensions are graphically represented in Figs. 1
to 8.
To correlate the surface tension data, the following equation has
been used:

21

p
r X
X
i
j
x1  1 x2  2 x1 x2
Aij x1 x2 TT 0

19

20

i0 j0

where xi and i are the corresponding mole fraction and surface tension of component i, T is the temperature, T0 is a reference temperature (T0 = 283.15 K), and Aij are adjustable parameters determined
by the method of least-squares, these parameters are summarized together with the standard deviations s in Table 2.

18
0

0.2

0.4

0.6

0.8

x1
Fig. 1. Surface tensions, , of the binary mixture 1-chlorobutane with butyl ethyl ether.
Experimental data (); tting equation (______).

D. Montao et al. / Journal of Molecular Liquids 181 (2013) 17

24

23
T = 283.15 K

T = 283.15 K

22

23

21

-1

/ mNm

/ mNm-1

22

21

20

19
20
18

19

17

16

18
0

0.2

0.4

0.6

0.8

0.2

0.4

0.6

0.8

x1

x1
Fig. 2. Surface tensions, , of the binary mixture 2-chlorobutane with butyl ethyl ether.
Experimental data (); tting equation (______).

Fig. 4. Surface tensions, , of the binary mixture 2-chloro-2-methylpropane with butyl

ethyl ether. Experimental data (); tting equation (______).

According with these results the surface tension behaviour seems to

be mainly related with the difference between the surface tension
of the mixed compounds. The compound with lower surface tension

tends to migrate from bulk to surface, leading to a negative surface tension deviation, this migration is enhanced by the difference of surface
tensions of the mixing compounds [30]. This fact could explain the results

25

24
T = 283.15 K

24
23

T = 283.15 K

23

22

/ mNm

-1

/ mNm

-1

22

21

21

20

19

20

18
19
17

16

18
0

0.2

0.4

0.6

0.8

x1
Fig. 3. Surface tensions, , of the binary mixture 1-chloro-2-methylpropane with butyl
ethyl ether. Experimental data (); tting equation (______).

0.2

0.4

0.6

0.8

x1
Fig. 5. Surface tensions, , of the binary mixture 1-chlorobutane with diisopropyl ether.
Experimental data (); tting equation (______); interpolated aneotropic points ().

D. Montao et al. / Journal of Molecular Liquids 181 (2013) 17

24

21
T = 283.15 K

23

T = 283.15 K

20
22
19

/ mNm-1

/ mNm-1

21

20

18

19
17
18
16
17

16

15
0

0.2

0.4

0.6

0.8

0.2

0.6

0.8

x1

x1
Fig. 6. Surface tensions, , of the binary mixture 2-chlorobutane with diisopropyl ether.
Experimental data (); tting equation (______); interpolated aneotropic points ().

obtained for the mixtures containing 1-chlorobutane, 2-chlorobutane or

1-chloro-2-methylpropane, for which the differences in the property
values for the two components of the mixture are considerable.

24

23

T = 283.15 K

22

21

/ mNm-1

0.4

Fig. 8. Surface tensions, , of the binary mixture 2-chloro-2-methylpropane with

diisopropyl ether. Experimental data (); tting equation (______); interpolated
aneotropic points ().

Meanwhile, surface tensions for 2-chloro-2-methylpropane and

butyl ethyl ether are not too different and the slight favourable interaction involving the oxygen atom on the ether with lone pairs of
electrons that can act as electronic density donor [31] and the chlorine atom of isomeric chlorobutane that shows a region of positive
electrostatic potential on the outer side of the molecule [32] can
modify the above mentioned trend resulting in a positive surface
tension deviation.
More information about the enrichment of the surface of a mixture in the component of lower surface tension is given by the surface
mole fractions, xiS. The composition of the surface mixture, that is, the
surface mole fraction of component i, is dened by [33,34]:
S

xi i =i i

20

where iS is the surface excess concentration of component i, which

are the real populations in the surface phase. This concentration is related with ij, the relative surface excess concentration of component i
with respect component j, by means of the classical relationship:

19



j
S
S
i i xi =xj j = i T

18

Finally, the magnitudes iS and xiS can be evaluated taking into account that in the surface phase, composed by a monomolecular layer,
the surface excess concentrations are related through the equation:

17

16

S S

0.2

0.4

0.6

0.8

x1
Fig. 7. Surface tensions, , of the binary mixture 1-chloro-2-methylpropane with
diisopropyl ether. Experimental data (); tting equation (______); interpolated
aneotropic points ().

i Ai i 1

where AiS is the partial molar area of component i, that can be calculated [12] from his molar volume, Vi, as Vi2/3N01/3.
To calculate all these magnitudes it is necessary to know the variation of the chemical potential with composition [35], this information

D. Montao et al. / Journal of Molecular Liquids 181 (2013) 17

Table 2
Parameters, Aij, and standard deviations, s(), for Eq. (2).
A00

A01

A02

A10

A11

A12

A20

A21

A22

A30

A31

A32

s()

Table 3
Calculated aneotropic coordinates, aneotropic mole fraction, x1an, and aneotropic surface tension, an.

1-Chlorobutane + butyl
1.29
0.06
0.63
0.40

ethyl ether
0.0150
0.0202
0.0418
0.0233

0.0001
0.0008
0.0001
0.0009

0.01

2-Chlorobutane + butyl
0.51
0.10
0.33
0.03

ethyl ether
0.0064
0.0028
0.0233
0.0144

0.0001
0.0001
0.0004
0.0006

0.00

1-Chloro-2-methylpropane + butyl ethyl ether

0.70
0.0151
0.09
0.0019
0.50
0.0223
0.07
0.0006

0.0002
0.0001
0.0002
0.0001

0.00

2-Chloro-2-methylpropane + butyl ethyl ether

0.38
0.0122
0.13
0.0080
0.05
0.0224
0.05
0.0320

0.0001
0.0003
0.0003
0.0009

0.00

1-Chlorobutane + diisopropyl ether

5.76
0.1663
0.91
0.0643
3.06
0.2210
1.78
0.0799

0.0007
0.0011
0.0041
0.0014

0.02

2-Chlorobutane + diisopropyl ether

4.70
0.1910
1.27
0.1504
1.59
0.1187
0.92
0.0924

0.0026
0.0025
0.0010
0.0016

0.02

1-Chloro-2-methylpropane + diisopropyl ether

4.24
0.0500
0.20
0.0028
2.19
0.1307
1.69
0.0016

0.0007
0.0004
0.0002
0.0018

0.01

2-Chloro-2-methylpropane + diisopropyl ether

0.47
0.0256
0.07
0.0044
0.05
0.0424
0.03
0.0057

0.0005
0.0001
0.0004
0.0002

0.01

an/mN m1

x1an

T/K

1-Chlorobutane + diisopropyl ether

283.15
0.0707

18.46

2-Chlorobutane + diisopropyl ether

283.15
0.0628

18.47

1-Chloro-2-methylpropane + diisopropyl ether

283.15
0.0567
288.15
0.0507
293.15
0.0447

18.44
18.07
17.71

2-Chloro-2-methylpropane + diisopropyl ether

313.15
0.0387
318.15
0.1111
323.15
0.1955

16.96
16.52
15.98

containing 2-chloro-2-methylpropane is opposite to the other mixtures, in this case the desorption of ether increases with temperature.
On the other hand for the systems formed by diisopropyl ether x2 x2
values also decreases with temperature, although for mixtures formed
by 1-chlorobutane or 2-chlorobutane there is an inexion point at
x2 = 0.7 and x2 = 0.8 respectively. Comparing the behaviour of the two
ethers it is clear that the excess surface composition of diisopropyl
ether is bigger than the corresponding excess surface composition of
butyl ethyl ether due to its lower surface tension. On the other hand,
the adsorption of the ether is clearly enhanced when 1-chlorobutane
is one of the component of the mixture.

0.075

0.050

x2 - x2

0.025

can be obtained from isothermal vapourliquid equilibrium data

[12,13].
In Figs. 9 and 10, the excess surface composition of ether, x2 x2,
in the studied mixtures at T = 298.15 K is shown; the representations
of the excess surface composition in the temperature range (288.15
308.15) K can be found in the supplementary material. This magnitude is positive for all the systems except for the system 2-chloro-2methylpropane + butyl ethyl ether, although at low temperatures
in the very rich chlorobutane region of the mixture 1-chloro-2methylpropane + diisopropyl ether x2 x2 is slightly negative. A positive x2 x2 value means that the concentration of ether on the surface is larger than in the bulk phase, that is the Gibbs adsorption
prevails over the favourable interactions in the bulk phase that tend
to retain the components in the bulk phase conrming our previous
discussion about the surface tension behaviour. For the systems
containing butyl ethyl ether the excess surface ether concentration
decreases with temperature, once more the behaviour of the mixture

-0.025

-0.050
0

0.2

0.4

0.6

0.8

x2
Fig. 9. Excess surface mole fraction of butyl ethyl ether, x2 x2, at T=298.15 K in the mixtures isomeric chlorobutane with butyl ethyl ether: 1-chlorobutane ( ),
2-chlorobutane ( ), 1-chloro-2-methylpropane (______), 2-chloro-2-methylpropane
().

D. Montao et al. / Journal of Molecular Liquids 181 (2013) 17

0.150

Table 4
Relative root-mean-square deviations, RMSDr, for the predictions of surface tensions.

0.125

x2 - x2

0.100

System

RMSDr/%

1-Chlorobutane + butyl ethyl ether

2-Chlorobutane + butyl ethyl ether
1-Chloro-2-methylpropane + butyl ethyl ether
2-Chloro-2-methylpropane + butyl ethyl ether
1-Chlorobutane + diisopropyl ether
2-Chlorobutane + diisopropyl ether
1-Chloro-2-methylpropane + diisopropyl ether
2-Chloro-2-methylpropane + diisopropyl ether

0.27
0.11
0.25
0.51
1.58
1.33
2.06
1.01

contribution method gives an excellent prediction of surface tension.

The best predictions are obtained for the mixtures 1-chlorobutane,
2-chlorobutane or 1-chloro-2-methylpropane with butyl ethyl ether
with RMSDr values lower than 0.30% and the worst prediction is for
the mixture 1-chloro-2-methylpropane with diisopropyl ether, although even for this system the deviations are not large. It can be
also outlined that taking into account the ethers studied here the largest
deviations are presented for the systems involving diisopropyl ether.

0.075

0.050

0.025
5. Conclusions

0
0

0.2

0.4

x2

0.6

0.8

Fig. 10. Excess surface mole fraction of diisopropyl ether, x2 x2, at T=298.15 K in the
mixtures isomeric chlorobutane with butyl ethyl ether: 1-chlorobutane ( ),
2-chlorobutane ( ), 1-chloro-2-methylpropane (______), 2-chloro-2-methylpropane
().

4. Surface tensions predictions

The assumptions that the bulk and surface phases are in equilibrium and the partial molar area of component i is the same as its molar
area leads to the following equations [16]:
i

xi
i

RT
Ai

ln

Acknowledgements

xi i
xbi bi

where and i are the surface tensions for the mixture and the pure
compound i, A i is the molar surface area of pure component i, this
magnitude can be approximated by the molar surface area of the corresponding pure component that can be calculated from the molar
volume, Ai = Vi2/3N01/3, T is the temperature, xi and xib are the mole
fractions in the surface and bulk liquid phases, i and ib are the corresponding activity coefcients.
Suarez et al. [15] have used the UNIFAC [36] method to calculate
the surface and bulk phase activity coefcients, in this work we
have employed the modied UNIFAC method by Gmehling [37].
In order to evaluate the agreement between experimental and
predicted results, the mean relative root mean square deviation
(RMSDr) expressed in % have been calculated using the following
equation:
RMSDr % 100 

Surface tension for the mixtures of isomeric chlorobutanes with butyl

ethyl ether or diisopropyl ether, has been measured from T=283.15 K to
T=313.15 K and correlated with a RedlichKister type equation. Surface
tension deviation, that is the deviation of surface tension behaviour with
respect to a lineal composition dependence, is negative, although for the
system 2-chloro-2-methylpropane+butyl ethyl ether this deviation is
slightly positive. The excess surface compositions were also calculated,
the study of these magnitudes shows how the Gibbs adsorption phenomenon should be one of the main processes that lead the mixture surface formation.
Finally, a group contribution method, Suarez method, has been
used to predict the surface tension of the studied mixtures giving satisfactory results especially for the mixtures containing butyl ethyl
ether.

m
i; exp i;pred
1X
m i1
i; exp

!2 !1=2
8

where m is the number of experimental data.

The values for the relative root mean square deviation, expressed as
percentages, are given in Table 4. These values indicate that the group

We are grateful at Diputacin General de Aragn for the nancial

support.
Appendix A. Supplementary data
Supplementary data to this article can be found online at http://
dx.doi.org/10.1016/j.molliq.2013.01.024.
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