J. Chem.

Thermodynamics 37 (2005) 415421

www.elsevier.com/locate/jct

Ternary (liquid + liquid) equilibria for mixtures of

1-hexyl-3-methylimidazolium (tetrauoroborate or
hexauorophosphate) + benzene + an alkane at T 298:2 K
and p 0:1 MPa
Trevor M. Letcher *, Prashant Reddy
School of Pure and Applied Chemistry, University of KwaZulu-Natal, Howard College Campus, Durban 4041, South Africa
Received 23 June 2003; received in revised form 26 April 2004; accepted 26 April 2004
Available online 25 November 2004

Abstract
Ternary (liquid + liquid) equilibrium data are presented for mixtures of 1-hexyl-3-methylimidazolium (tetrauoroborate or hexauorophosphate) + benzene + (heptane or dodecane or hexadecane) at T 298:2 K. The tie line compositions of the conjugate solutions were
obtained by means of density measurements and a standard density calibration curve. Large regions of immiscibility (increasing in the
order of hexadecane > dodecane > heptane) and favourable skewing of the tie lines towards the solvent axis provide indications of the
favourable use of the ionic liquids in solvent extraction. Selectivity values computed from the experimental data conrm this. Correlation of
the experimental tie lines was conducted through the use of the NTRL equation, which provides good correlation of the experimental data.
2004 Elsevier Ltd. All rights reserved.
Keywords: (Liquid + liquid) equilibria; Density; Ionic liquids; NTRL; Aromatic compound; Aliphatic compound

1. Introduction
Ionic liquids are an emerging class of green solvents
whose potential diverse applications have been well
documented and acknowledged by researchers worldwide. Such elds of interest for the potential successful
incorporation of ionic liquids, extends from synthesis to
catalysis [1] to the focus of this research, which is separation technology. The extent to which ionic liquids
can be incorporated into industrial processes needs to be
assessed so as to speed up the development of cleaner,
more ecient technologies, which have minimal deleterious impact upon the environment. However, it should
be noted that there is concern about the decomposition
of hexauorophosphate-containing ionic liquids in the
presence of water and elevated temperatures [2] to
hydrogen uoride It is the focus of this research work to
obtain phase equilibria data to screen two ionic liquids
*

Corresponding author. Tel.: +27-31-260-3090; fax: +27-31-2603091.

E-mail address: letcher@okzn.ac.za (T.M. Letcher).
0021-9614/$ - see front matter 2004 Elsevier Ltd. All rights reserved.
doi:10.1016/j.jct.2004.05.001

for their applicability in unit operations such as solvent

extraction for the recovery of valuable co-products from
product streams. Ionic liquids possess such favourable
physical properties as negligible vapour pressures, high
liquid phase temperature existence ranges and exibility
in design and structure of the solvent [3].
Two ionic liquids (structures shown below) with the
same organic cation, i.e. 1-hexyl-3-methylimidazolium
or [hmim] and dierent anions, i.e. tetrauoroborate or


BF

4 and hexauorophosphate or PF6 , have been
studied. This is in accordance with the objectives of a
comparative study of the anion eect and how this
can be exploited for the tailor-made design of the most
ecient solvents for the separation of complex hydrocarbon mixtures such as (aliphatic + aromatic) [4].
CH2CH2CH2CH2CH2CH3
N
+
N

BF4

CH3
1-hexyl-3-methylimidazolium tetrafluoroborate

416

T.M. Letcher, P. Reddy / J. Chem. Thermodynamics 37 (2005) 415421

CH2CH2CH2CH2CH2CH3
N
+
N

PF6

CH3
1-hexyl-3-methylimidazolium hexafluorophosphate

In this comparative study the size of the immiscibility

regions of the binodal curves and the tie line data are
key parameters. The selectivity values [5] from the
experimental tie line data provide a good indication of
the separation eciency of the ionic liquids for (aliphatic + aromatic).
2. Experimental
2.1. Chemicals
The two ionic liquids, [hmim]BF4 and [hmim]PF6 ,
were supplied by Fluka Chemika, with quoted purities
of 0.97 mass fraction. The ionic liquids were further
puried by applying a low-pressure vacuum of 10
4 Pa
for 2 h whilst heating at T 373 K. This removed the
water and other volatile impurities. The loss of mass
amounted to 0.03 mass percent.
The compound n-heptane was purchased from Saarchem with a purity of 0.995 mass fraction; n-dodecane
was obtained from Fluka Chemika with a purity of 0.97
mass fraction and hexadecane from Acros Organics,
with a quoted purity of 0.99 mass fraction. Benzene was
obtained from Associated Chemical Enterprises with a
purity of 0.995 mass fraction. Benzene was stored over
0.4 nm molecular sieves to remove residual traces of
water. The physical properties of the compounds [6] are
listed in table 1.
2.2. Procedure

3. Results

The binodal curves were determined at T 298:2 K

and p 0:1 MPa through the use of the cloud-point
TABLE 1
Physical properties of the pure components at T 298:15 K and
p 0:1 MPa; densities q, molar masses M and molar volumes Vm
Component

M

3

Lit.a

Exp.

1.1493b
1.290c
0.8736
0.6837
0.7487
0.7700

1.1481
1.2935
0.8732
0.6906
0.7470
0.7715

Reference [6].
Reference [13].
c
Reference [14].

Vm

g  cm

g  mol
3

254.08
312.24
78.114
100.20
170.34
226.44

221.31
244.31
89.453
145.09
228.03
293.50

1

g  cm

[hmim]BF4
[hmim]PF6
Benzene
Heptane
Dodecane
Hexadecane

titration technique described by Letcher and Siswana

[7]. All mixtures were prepared and titrated in screwcap glass vials with septa to allow for careful sampling
with glass syringes. There was negligible mass loss from
the glass vials. The determination of the tie line compositions was carried out by correlating the densities of
the two immiscible liquid phases of the conjugate solutions with that of standard curves of density versus
composition for the three components. The standard
curve was obtained by measuring the densities of binary
mixtures of benzene and the alkanes and equilibrium
ternary mixtures of the components, i.e. at the cloudpoint, throughout the composition range of the ternary
system. The density values of each conjugate phase, i.e.
two phases, in the ternary mixture was then correlated
with the standard curve to obtain the compositions of
the components in each of the phases. Only two of the
three component compositions are required for each
phase as the third is obtained by subtracting the sum of
the other two from a value of 1. The densities were
measured through the use of a calibrated Anton Paar
DMA 5000 density meter with an uncertainty of 1  10
6
g  cm
3 in the measurement. Densities were chosen as a
means of analysis of compositions as opposed to
refractive indices, described by Briggs and Comings [8],
as a result of the greater accuracy of measuring densities
than refractive indices. The negligible volatility of the
ionic liquids rendered other quantitative techniques such
as gas-liquid chromatography non-applicable. The
temperature was monitored through the use of a Hewlett Packard quartz thermometer to within 0.01 K. The
precision of the technique for the determination of
points on the binodal curve was 0.003 mole fraction.
For the tie line composition determination, the precision
was 0.004 mole fraction.

The compositions of the cloud point ternary

mixtures on the binodal curve at T 298.2 K are given
in table 2. The binodal curves together with the tie lines
have been plotted in gures 1 and 2, for {[hmim](BF4 )
(1) + benzene (2) + an alkane) (3)} and {[hmim](PF6 )
(1) + benzene (2) + an alkane) (3)}, respectively. The
compositions of the conjugate solutions have been presented in tables 3 and 4 for {[hmim](BF4 ) (1) + benzene
(2) + an alkane) (3)} and {[hmim](PF6 ) (1) + benzene
(2) + an alkane)(3)}, respectively.
The selectivity (S) is an important parameter [9]
in assessing the feasibility of utilizing the solvent in
(liquid + liquid) extraction. With regards to the (aliphatic + aromatic) studied, the feasibility of extracting
aromatics from aliphatics is given as:

S x2 =x3 ionic

liquid-rich phase =x2 =x3 alkane-rich phase ;

T.M. Letcher, P. Reddy / J. Chem. Thermodynamics 37 (2005) 415421

417

TABLE 2
Compositions of points on the binodal curves at T 298:2 K for the ternary mixtures, {[hmim](BF4 or PF6 ) (1) + benzene (2) + (heptane or dodecane
or hexadecane) (3)}
Heptane

Dodecane

Hexadecane

x1

x2

0.0010
0.0020
0.0020
0.0050
0.0060
0.2540
0.5330
0.5730
0.6240
0.7300
0.8200
0.9020

0.6220
0.4640
0.0000
0.9950
0.7530
0.7460
0.4210
0.3870
0.3200
0.2000
0.1030
0.0000

{[hmim]BF4 (1) + benzene (2) + an alkane (3)}

0.0001
0.0000
0.0008
0.8748
0.0017
0.7580
0.0050
0.9950
0.2540
0.7460
0.3513
0.6440
0.4759
0.5013
0.5946
0.3836
0.6658
0.3051
0.8366
0.1321
0.8752
0.0919
0.9638
0.0000

0.0002
0.0004
0.0007
0.0015
0.0016
0.0040
0.2165
0.4100
0.5288
0.6598
0.8034
0.8859
0.9161

0.8962
0.8762
0.9993
0.6902
0.0000
0.9992
0.7835
0.5688
0.4402
0.2965
0.1234
0.1141
0.0000

{[hmim]PF6 (1) + benzene (2) + an alkane (3)}

0.0004
0.0000
0.0008
0.8854
0.0013
0.7713
0.0018
0.4960
0.0035
0.1503
0.0040
0.9960
0.2165
0.7835
0.3809
0.6108
0.5343
0.4448
0.5999
0.3800
0.7308
0.2300
0.8463
0.1061
0.9471
0.0000

x1

x2

(b)
(a)

0.0000
0.8603
0.5736
0.2988
0.9950
0.7460
0.7002
0.5652
0.4535
0.2517
0.0761
0.0000

0.0001
0.0003
0.0004
0.0040
0.2165
0.3724
0.4791
0.6166
0.7365
0.9080
0.9783

0.0000
0.5452
0.8631
0.9960
0.7835
0.6262
0.5181
0.3786
0.2489
0.0715
0.0000

(c)

Benzene
1

x3

x2

x1

[hmim]BF4

x1
Dodecane

x3

x2

Heptane

0.0001
0.0007
0.0016
0.0027
0.0050
0.2540
0.2989
0.4332
0.5348
0.7334
0.9090
0.9808

x3

x2

Benzene

Benzene
1

x1

[hmim]BF4

x2

Hexadecane

x1

[hmim]BF4

FIGURE 1. Binodal curves and tie lines for the ternary mixtures {[hmim](BF4 ) (1) + benzene (2) + (heptane or dodecane or hexadecane) (3)} at
T 298:2 K. (a) Heptane; (b) dodecane; (c) hexadecane. j, Binodal point; d tie line end points.

where x2 refers to the benzene mole fraction and x3 refers

to the alkane mole fraction. The selectivity values
computed from the tie line data are presented in tables 5
and 6 for {[hmim](BF4 ) (1) + benzene (2) + an alkane)
(3)} and {[hmim](PF6 ) (1) + benzene (2) + an alkane)
(3)}, respectively.

4. Discussion
The aromatic compound benzene displayed partial
solubility in both ionic liquids. The solubility limits for
[hmim]BF4 and benzene are 0.7460 and 0.0050 mole
fraction compositions, respectively. For [hmim]PF6 and

418

T.M. Letcher, P. Reddy / J. Chem. Thermodynamics 37 (2005) 415421

(a)

Benzene
1

(b)

(c)

Benzene
1

x3
x3

x3

x1

Heptane

x2

x2

Benzene

[hmim]PF6

x1

Dodecane

x2

x1
Hexadecane

[hmim]PF6

[hmim]PF6

FIGURE 2. Binodal curves and tie lines for the ternary mixtures[hmim](PF6)(1) + benzene (2) + (heptane or dodecane or hexadecane)(3) at 298.2 K.
(a) Heptane. (b) Dodecane. (c) Hexadecane. j, binodal point; d tie line end points.

TABLE 3
Compositions of the conjugate solutions, x01 , x02 and x001 , x002 for the
ternary mixtures {[hmim](BF4 ) (1) + benzene (2) + (heptane or dodecane or hexadecane) (3)} at 298.2 K

TABLE 4
Compositions of the conjugate solutions, x01 , x02 and x001 , x002 for the
ternary mixtures {[hmim](PF6 ) (1) + benzene (2) + (heptane or dodecane or hexadecane) (3)} at 298.2 K
[hmim]PF6 -rich layer

Alkane-rich layer

x002

x01

x02

x001

Heptane
0.0030
0.0032
0.0022
0.0016
0.0020
0.0022
0.0032
0.0022
0.0018
0.0016
0.0011
0.0016

0.9438
0.9333
0.8881
0.8067
0.7095
0.6495
0.4600
0.4799
0.4199
0.3203
0.2286
0.1280

0.2692
0.3055
0.3270
0.4070
0.4250
0.4308
0.4782
0.4900
0.5872
0.6756
0.7918
0.8904

0.7239
0.6857
0.6630
0.5737
0.5548
0.5461
0.4954
0.4801
0.3755
0.2783
0.1387
0.0288

Heptane
0.0030
0.0022
0.0020
0.0014
0.0012
0.0012
0.0007
0.0006
0.0008
0.0007
0.0006
0.0005

0.9495
0.8501
0.8390
0.7307
0.6882
0.6722
0.5689
0.5506
0.4197
0.3020
0.1512
0.0414

0.6507
0.6127
0.5001
0.4476
0.3517
0.2306
0.1002

Dodecane
0.0074
0.0060
0.0052
0.0048
0.0042
0.0035
0.0021

0.9413
0.8554
0.7121
0.6200
0.5157
0.3516
0.2060

0.3308
0.3597
0.4309
0.4920
0.6448
0.8299
0.8912

0.6603
0.6306
0.5590
0.4912
0.3274
0.1275
0.0590

Dodecane
0.0038
0.0032
0.0028
0.0024
0.0021
0.0018
0.001

0.9428
0.8279
0.7446
0.6562
0.4602
0.2536
0.1451

0.6616
0.6240
0.4917
0.3758
0.2957
0.1701
0.1001
0.0659
0.0263

Hexadecane
0.0007
0.0007
0.0006
0.0005
0.0003
0.0003
0.0001
0.0001
0.0000

0.9950
0.9441
0.8103
0.6558
0.5201
0.4051
0.3350
0.2485
0.0972

0.3132
0.3829
0.6240
0.7501
0.9062

0.6840
0.6136
0.3683
0.2348
0.0745

Hexadecane
0.0004
0.0004
0.0001
0.0001
0.0000

0.9450
0.8509
0.5448
0.3950
0.1722

[hmim]BF4-rich layer

Alkane-rich layer

x01

x02

x001

0.2798
0.2894
0.3155
0.3844
0.4562
0.4818
0.5370
0.5738
0.6000
0.6792
0.7499
0.8108

0.7179
0.7044
0.6769
0.5961
0.5140
0.4852
0.4180
0.3800
0.3480
0.2600
0.1783
0.1043

0.3399
0.3775
0.4799
0.5310
0.6211
0.7395
0.8680
0.3348
0.3701
0.4992
0.6145
0.6919
0.8142
0.8812
0.9162
0.9542

benzene, the solubility limits are 0.7835 and 0.0040 mole

fraction compositions, respectively. The solubility of the
alkanes, i.e. heptane, dodecane and hexadecane in

x002

[hmim]BF4 is 0.0980, 0.0362 and 0.0119 mole fractions,

respectively. The solubility of heptane, dodecane and
hexadecane in [hmim]PF6 is 0.0839, 0.0529 and 0.0217
mol fractions, respectively.

T.M. Letcher, P. Reddy / J. Chem. Thermodynamics 37 (2005) 415421

TABLE 5
Selectivity values S together with the tie line composition at 298.2 K
for the ternary mixtures {[hmim](BF4 ) (1) + benzene (2) + (heptane or
dodecane or hexadecane) (3)} at 298.2 K
[hmim]BF4-rich layer

Alkane-rich layer

x01

x02

x001

x002

0.2798
0.2894
0.3155
0.3844
0.4562
0.4818
0.5370
0.5738
0.6000
0.6792
0.7499
0.8108

0.7179
0.7044
0.6769
0.5961
0.5140
0.4852
0.4180
0.3800
0.3480
0.2600
0.1783
0.1043

Heptane
0.0030
0.0032
0.0022
0.0016
0.0020
0.0022
0.0032
0.0022
0.0018
0.0016
0.0011
0.0016

0.9438
0.9333
0.8881
0.8067
0.7095
0.6495
0.4600
0.4799
0.4199
0.3203
0.2286
0.1280

0.3399
0.3775
0.4799
0.5310
0.6211
0.7395
0.8680

0.6507
0.6127
0.5001
0.4476
0.3517
0.2306
0.1002

Dodecane
0.0074
0.0060
0.0052
0.0048
0.0042
0.0035
0.0021

0.3348
0.3701
0.4992
0.6145
0.6919
0.8142
0.8812
0.9162
0.9542

0.6616
0.6240
0.4917
0.3758
0.2957
0.1701
0.1001
0.0659
0.0263

Hexadecane
0.0007
0.0007
0.0006
0.0005
0.0003
0.0003
0.0001
0.0001
0.0000

419

TABLE 6
Selectivity values S together with the tie line composition at 298.2 K
for the ternary mixtures {[hmim](PF6 ) (1) + benzene (2) + (heptane or
dodecane or hexadecane) (3)} at 298.2 K
S

[hmim]PF6-rich layer

Alkane-rich layer

x01

x02

x001

x002

17.59
7.73
11.00
7.29
7.01
7.88
10.84
8.84
9.22
9.05
8.37
8.35

0.2692
0.3055
0.3270
0.4070
0.4250
0.4308
0.4782
0.4900
0.5872
0.6756
0.7918
0.8904

0.7239
0.6857
0.6630
0.5737
0.5548
0.5461
0.4954
0.4801
0.3755
0.2783
0.1387
0.0288

Heptane
0.0030
0.0022
0.0020
0.0014
0.0012
0.0012
0.0007
0.0006
0.0008
0.0007
0.0006
0.0005

0.9495
0.8501
0.8390
0.7307
0.6882
0.6722
0.5689
0.5506
0.4197
0.3020
0.1512
0.0414

5.25
13.54
12.56
10.90
12.22
11.49
14.20
13.06
13.90
13.94
11.20
13.09

0.9413
0.8554
0.7121
0.6200
0.5157
0.3516
0.2060

3.77
10.13
9.93
12.66
12.04
14.15
12.11

0.3308
0.3597
0.4309
0.4920
0.6448
0.8299
0.8912

0.6603
0.6306
0.5590
0.4912
0.3274
0.1275
0.0590

Dodecane
0.0038
0.0032
0.0028
0.0024
0.0021
0.0018
0.001

0.9428
0.8279
0.7446
0.6562
0.4602
0.2536
0.1451

4.20
13.26
18.78
15.21
13.76
8.79
6.98

0.9950
0.9441
0.8103
0.6558
0.5201
0.4051
0.3350
0.2485
0.0972

8.08
5.95
12.48
20.20
21.93
15.82
10.60
11.15
12.49

0.3132
0.3829
0.6240
0.7501
0.9062

0.6840
0.6136
0.3683
0.2348
0.0745

Hexadecane
0.0004
0.0004
0.0001
0.0001
0.0000

0.9450
0.8509
0.5448
0.3950
0.1722

14.11
30.64
39.94
23.81
18.51

The increasing size of the immiscibility region of the

binodal curves for increasing alkane chain length corresponds with the reduction in solubility [10] of the ionic
liquid in an increasingly hydrophobic alkane.
The selectivity value S is an important parameter in
assessing the eciency of the ionic liquid in eecting the
selective extraction of the aromatic from (aromatic + aliphatic). All the selectivity values for all regions
of the binodal curves are greater than unity, from which
it can be inferred that the extraction of an aromatic
compound from an (aliphatic + aromatic) is indeed possible. The selectivity values increase in the order: hexadecane > dodecane > heptane, which is in accordance
with the increasing size of the immiscibility region. From
a comparative study point of view, i.e. the anion eect,
the selectivity values for the PF6 ionic liquid are generally
higher than those for BF4 . It can be concluded therefore
that [hmim]PF6 would be better suited for the separation
of (aromatic + aliphatic). The use of ionic liquids in solvent extraction is indeed quite favourable due to the ease

of the recovery as ionic liquids have an extremely low

vapour pressure, hence the blatant economic and environmental incentives for their use.

5. Tie line correlation

The non-random two-liquid equation (NTRL) [11]
was used to correlate the experimental tie line data for
the ternary mixtures investigated here.
The NTRL equation for a solution of m components
is
Pm
m
GEm X
j1 sji Gji xj

xi Pm
;
2
RT
l1 Gli xl
i1
where GEm is the molar excess Gibbs free energy,
sji gji
gii =RT ;



Gji exp
aji sji ;

3
4

and
aji aij :

420

T.M. Letcher, P. Reddy / J. Chem. Thermodynamics 37 (2005) 415421

TABLE 7
Values of parameters for the NTRL equation for the ternary mixtures
{[hmim](BF4 or PF6 ) (1) + benzene (2) + an alkane) (3)}
i; j

gij
gjj

gji
gii

1

(J  mol )

1, 2
1, 3
2, 3
1, 2
1, 3
2, 3
1, 2
1, 3
2, 3

12
13
23
12
13
23
12
13
23

The parameters calculated in this manner in the form

of gij
gji and gji
gii for the NTRL equation is given
in table 7, together with the root mean square deviation
r values dened below as:

(J  mol
1 )

{[hmim]BF4 (1) + benzene (2) + an

Heptane (0.018)a
178.05
14617.24
3784.48
Dodecane (0.006)b
)2418.84
13438.71
7609.32
Hexadecane (0.016)c
)2311.04
5757.46
7997.74

alkane (3)}

{[hmim]PF6 (1) + benzene (2) + an

Heptane (0.015)d
)242.21
8814.85
4009.42
Dodecane (0.004)a
675.24
10399.94
8603.74
Hexadecane (0.004)a
13971.15
10582.89
53284.20

alkane (3)}

(
r

X X X exp
2
xilm
xcalc
ilm =6k
i

5877.66
9199.01
)639.29

)1=2
;

where x is the mole fraction and the subscripts i, l and m

provide a designation for the component, the phase and
the tie line, respectively. The value k designates the
number of interaction components. The values of r in
table 7 provide a measure of the accuracy of the correlation. As can be inferred from these values, a fairly
good correlation of the experimental values with the
NTRL model was obtained.

9049.09
42893.42
)4037.74
8227.37
13913.85
)5335.11

5778.06
12617.99
)502.16

6. Conclusion
This research has been focused on a comparative
study of two ionic liquids as solvents in (liquid + liquid)
extraction. Binodal curve data and tie line data were
obtained for mixtures of {1-hexyl-3-methylimidazolium(tetrauoroborate or hexauorophosphate) + benzene + (heptane or dodecane or hexadecane)} at T
298:2 K. The selectivity values were higher for [hmim]PF6 , indicating that it would be a better choice as a
solvent in the separation of (aromatic + aliphatic) than
[hmim]BF4 .

11812.17
11760.57
)2203.55
14869.99
28216.74
11066.35

The r values are given in parenthesis.

Calculated with aij 0:45.
b
Calculated with aij 0:25:
c
Calculated with aij 0:20:
d
Calculated with aij 0:4.
a

Acknowledgements
The equations and algorithms used in the calculations of
the tie line compositions are in accordance with the
method employed by Walas [12].
The objective function, F P, was used to minimize
the dierence between the experimental and calculated
mole fraction compositions as dened as:
F P

n
X


x01i

2
x01i calc

i1

x001i
x001i calc

2

References

2

x02i
x02i calc
2

x002i
x002i calc ;

The authors acknowledge the support of the N.R.F.

(South Africa) and the University of Natal Research
Oce, Durban for nancial support.

where P is the set of parameters vector, n refers to the

number of experimentally determined points, x01i ; x02i ; x01i
(calc), and x02i (calc) are the experimental and calculated mole fractions of one phase and x001i ; x002i ; x001i (calc),
and x002i (calc) are the experimental and calculated mole
fractions of the other phase. For the NTRL model the
non-randomness parameter was set at a value of
aij 0:2, 0.25, 0.4 or 0.45. The equation was optimised for all parameters using the Rosenbrock iterative process.

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JCT 03/087