Density, viscosity, and refractive index properties for the binary mixtures of n -butylammonium acetate ionic liquid + alkanols at sveral temperatures

Article abstract of DOI:10.1021/je200707b

Densities and viscosities were determined for the binary mixtures of n-butylammonium acetate ionic liquid (N4AC) with methanol, ethanol, n-propanol, and n-butanol at temperatures of (293.15, 298.15, 303.15, 308.15, and 313.15) K under atmospheric pressure. The refractive indices of the above-mentioned binary mixtures were measured at 298.15 K. Excess molar volumes V^E, viscosity deviations Δη, and refractive index deviations Δn _D were obtained from the experimental data and fitted with the Redlich-Kister equation. The correlation results were in good agreement with the experimental data, and optimal fitting parameters were presented. The results were interpreted in terms of interactions and structural factors of N4AC + alkanols mixtures.

Full text of DOI:10.1021/je200707b

Article
pubs.acs.org/jced
Density, Viscosity, and Refractive Index Properties for the Binary
Mixtures of n-Butylammonium Acetate Ionic Liquid + Alkanols at
Several Temperatures
Yingjie Xu,†,‡ Jia Yao,† Congmin Wang,† and Haoran Li*,†
†Department of Chemistry, Zhejiang University, Hangzhou, Zhejiang 310027, China
‡Department of Chemistry, Shaoxing University, Shaoxing, Zhejiang 312000, China
ABSTRACT: Densities and viscosities were determined for
the binary mixtures of n-butylammonium acetate ionic liquid
(N4AC) with methanol, ethanol, n-propanol, and n-butanol at
temperatures of (293.15, 298.15, 303.15, 308.15, and 313.15)
K under atmospheric pressure. The refractive indices of the
above-mentioned binary mixtures were measured at 298.15 K.
Excess molar volumes VE, viscosity deviations Δη, and
refractive index deviations ΔnD were obtained from the
experimental data and fitted with the Redlich−Kister equation. The correlation results were in good agreement with the
experimental data, and optimal fitting parameters were presented. The results were interpreted in terms of interactions and
structural factors of N4AC + alkanols mixtures.
small number of density and viscosity properties have been
reported in the literature compared with other ILs.42−46
To improve the application of the simple ammonium ILs, it
was necessary to study their physicochemical properties with
other solvents. In the present study, we chose n-butylammo-
nium acetate IL (N4AC) as an example, which is a typical
simple ammonium IL and can be used as the acidic catalyst,
with its structure was shown in Scheme 1. The densities and
1. INTRODUCTION
Room-temperature ionic liquids (ILs) are attracting more and
more attention due to their unique physicochemical properties
and have been applied in many industrial processes, such as
organic synthesis,1,2 catalytic reactions,3−7 CO2 capture,8−10
electrochemistry,11,12 and multiphase separations.13−18 The
thermodynamic properties of the mixtures of ILs with organic
molecular liquids are important not only for designing chemical
industry separation processes and transport equipment but also
for predicting the properties and characteristics of ILs from a
theoretical point of view.19,20 Recently, the density and viscosity
properties of the binary mixtures containing imidazole-,20−28
pyridinium-,29−32 phosphonium-,33,34 and pyrrolidinium-
based35 ILs have been widely investigated. However, the
experimental data on the density and viscosity properties of
new task-specific ILs were rather limited.36
Recently, some simple ammonium ILs have attracted
considerable interest in organic synthesis and industry due to
their advantages such as easy preparation, cheap cost, and low
toxicity. Our group has successfully applied a series of simple
ammonium ILs as both acidic catalysts and solvents to produce
dialkoxypropanes by cracking reactions,37,38 cinnamic acid
through the hydrolytic reaction of 1,1,1,3-tetrachloro-3-phenyl-
propane,39 and unsaturated ketones by the Saucy−Marbet
reaction,40 eliminating the need for a volatile organic solvent
and additional catalyst. Because of their excellent catalytic
properties in organic reactions, these physicochemical proper-
ties have also attracted the attention of a growing number of
scientists. The structural organization of n-butylammonium
nitrate (N4NO3) IL aqueous solutions has been investigated
using 1H NMR chemical shifts combined with the local
composition model.41 In spite of the importance of properties
of the simple ammonium ILs in different solvent media, only a
Scheme 1. Molecular Structure and Synthesis of N4AC
viscosities of binary mixtures of N4AC with methanol, ethanol,
n-propanol and n-butanol were measured at temperatures of
(293.15, 298.15, 303.15, 308.15, and 313.15) K under
atmospheric pressure. The refractive indices were determined
at 298.15 K for the above-mentioned binary mixtures. Based on
these experimental results, excess molar volumes VE, viscosity
deviations Δη, and refractive index deviations ΔnD were
calculated and fitted with the Redlich−Kister equation.
2. EXPERIMENTAL SECTION
Chemicals. Methanol, ethanol, n-propanol, n-butanol, n-butyl-
amine, and acetate acid (analytical reagent grade, with a nominal
mass > 99 %) were obtained from Shanghai Chemical Co. Ltd.,
Received: July 28, 2011
Accepted: January 4, 2012
Published: January 24, 2012
© 2012 American Chemical Society
298
dx.doi.org/10.1021/je200707b | J. Chem. Eng.Data 2012, 57, 298−308

Journal of Chemical & Engineering Data
Article
Table 1. Densities ρ, Viscosities η, and Refractive Indices nD of the Pure Components at Several Temperatures
−3
ρ/g·cm
η/mPa·s
nD
lit.
component
T/K
exptl
lit.
Dr %
exptl
lit.
Dr %
exptl
Dr %
0.007
water
298.15
293.15
298.15
303.15
308.15
313.15
293.15
298.15
303.15
308.15
313.15
293.15
298.15
303.15
308.15
313.15
293.15
298.15
303.15
308.15
313.15
293.15
298.15
303.15
308.15
313.15
0.99709
0.79128
0.78656
0.78183
0.77707
0.77229
0.78954
0.78525
0.78093
0.77657
0.77218
0.80355
0.79955
0.79552
0.79144
0.78734
0.80970
0.80590
0.80205
0.79817
0.79426
0.95961
0.95644
0.95333
0.95015
0.94698
0.99706848
0.79121836
0.78650736
0.78177836
0.77702836
0.77223836
0.789029
0.785529
0.780329
0.776029
0.772029
0.803629
0.799629
0.795629
0.791529
0.787429
0.809829
0.806029
0.802129
0.798229
0.794329
0.002
0.007
0.006
0.006
0.005
0.006
0.069
0.032
0.081
0.074
0.024
0.006
0.006
0.010
0.007
0.008
0.012
0.013
0.006
0.004
0.005
0.891
0.588
0.89035
0.588422
0.550922
0.515422
0.484922
0.457622
1.21649
1.13249
1.01049
0.90750
0.83449
2.20249
1.97349
1.73349
1.54250
1.37950
2.93750
2.56950
2.26050
1.99850
1.78450
0.011
0.068
1.107
0.698
1.052
0.962
2.056
0.353
1.881
1.433
0.959
1.226
0.101
1.385
1.686
1.958
1.566
1.868
2.035
2.102
1.513
1.3329
1.333035
methanol
0.557
1.3265
1.3594
1.3834
1.3973
1.4426
1.326447
1.359347
1.383347
1.397147
0.008
0.008
0.007
0.014
0.519
0.490
0.462
ethanol
1.241
1.128
1.029
0.920
0.842
n-propanol
n-butanol
N4AC
2.229
1.975
1.757
1.568
1.406
2.983
2.617
2.306
2.040
1.811
771.694
546.348
397.170
294.586
222.241
Shanghai, China. They were purified by the methods described
by our laboratory previously.47 The purity of these materials
was checked by gas chromatography. The density, viscosity, and
refractive index of methanol, ethanol, n-propanol, and n-butanol
were determined and compared with literature values listed in
Table 1.
Apparatus and Procedure. The binary mixtures of N4AC
with methanol, ethanol, n-propanol, and n-butanol were
prepared by using an analytical balance with a precision of
1.0·10−5 g. The errors in mole fractions of the binary mixtures
were less than
1.0·10−4. All of the samples were prepared
immediately before the density, viscosity, and refractive index
measurements to avoid the evaporation of the alkanols. The
N4AC used in the experiment was not recycled and reused.
The densities of pure materials and binary mixtures were
measured with a vibrating-tube densimeter (Anton Paar DMA
5000 M). The uncertainty of density is 5.0·10−6 g·cm−3. The
densimeter was calibrated with ultrapure water, which was also
listed in Table 1, compared with literature. Two integrated Pt
100 platinum thermometers (uncertainty: 0.01 K) together
with Peltier elements provide an extremely precise thermo-
statting of the sample. The overall average relative deviation
(Dr %) between density measurements and literature values of
alkanols was 0.019 %, according to the data from Table 1.
The viscosities of pure materials and binary mixtures were
measured by an Anton Paar AMVn automated microviscometer
(reproducibility < 0.5 %, repeatability < 0.1 %),30,51 which used
the rolling-ball principle. Calibration was carried out using
ultrapure water or viscosity standard oils (no. H117; Anton
Paar Co). The temperature was controlled by a built-in precise
Peltier thermostat within 0.01 K. Triplicate measurements of
N4AC was prepared from n-butylamine and acetate acid
according to the procedure reported previously by our
laboratory (see Scheme 1).39 Specific processes were as
follows: into a 100 mL three-necked flask under vigorous
stirring, 0.55 mol of n-butylamine was placed, then 0.50 mol of
acetate acid was dropped in slowly. The temperature was kept
at 25 °C. After the neutralization reaction for 4 h, the excess
n-butylamine was separated, and then N4AC was obtained and
dried under vacuum at 70 °C for at least 48 h before use. The
water content was determined to be about 200 ppm by Karl
Fischer titration (Mettler Toledo DL32, Switzerland). The
structure of N4AC was identified by Fourier transform infrared
1
(FT-IR; Nicolet FT-IR/Nexus470) and H NMR spectros-
copy (Bruker, 400 MHz, CDCl3). IR vibrational frequencies
(in cm−1) were as follows: 3039 (+N−H stretching vibration),
2961, 2933, and 2875 (C−H stretching vibration), 1633 (CO
stretching vibration), (1557 +N−H bending vibration), and
1467 (C−H bending vibration), which was consistent with the
1
structure of N4AC. The H NMR chemical shifts δ were as
follows: 0.94 (t, 3H, J = 7.36 Hz, +NH3CH2CH2CH2CH3), 1.39
(m, 2H, + NH3CH2CH2 CH2 CH3 ), 1.63 (m, 2H,
+NH3CH2CH2CH2CH3), 1.93 (s, 3H, CH3COO−), 2.82
flow times were reproducible within
0.02 s. The overall
average relative deviation (Dr %) between density measure-
ments and literature values of alkanols was 1.301 %, according
to the data from Table 1.
Refractive indices were measured using an Abbe refrac-
tometer model WAY-2S, and the temperatures were controlled
+
(t, 2H, J = 7.56 Hz, NH3CH2CH2CH2CH3), 8.16 (s, 3H,
1
+NH3CH2CH2CH2CH3), and the total peak integral in H
NMR spectrum was found to correspond for N4AC to a
nominal purity higher than 99 %.
by a circulating-water bath with the accuracy of
0.01 K.
299
dx.doi.org/10.1021/je200707b | J. Chem. Eng.Data 2012, 57, 298−308

Journal of Chemical & Engineering Data
Article
Ultrapure water was used as a reference for calibration. The
uncertainty in refractive index was estimated to be 1.0·10−4.
The sample support was rinsed with acetone and dried with a
paper towel. The overall average relative deviation (Dr %)
between density measurements and literature values of alkanols
was 0.009 %, according to the data from Table 1.
Moreover, the ability to form hydrogen bonding between the
alkanols with N4AC follows this order: methanol > ethanol >
n-propanol > n-butanol, and the higher hydrogen bonding
interaction leads to larger |VE| values. On the other hand, the
molecular size of the solvents follows this order: methanol <
ethanol< n-propanol < n-butanol, which leads to the most
notable packing efficiency between methanol with N4AC and
increase of the |VE| values. To sum up, those are reasons why
the |VE| values for the studied systems follow this order:
methanol > ethanol > n-propanol > n-butanol. A similar
phenomenon has been observed by Mokhtarani et al.21 and
Gonzalez et al.;52 the mixtures of alkanols with 1-methyl-3-
octylimidazolium nitrate or 1-methyl-3-octylimidazolium chlor-
ide also have negative VE over the entire composition range,
and the |VE| values for the studied systems also decrease with
the increase of the alcohol chain length.
3. RESULTS AND DISCUSSION
The experimental values of the density ρ, viscosity η, and
refractive index nD for binary mixtures of N4AC with methanol,
ethanol, n-propanol, and n-butanol at different temperatures
under atmospheric pressure are presented in Table 2. The
excess molar volumes VE, viscosity deviations Δη, and refractive
index deviations ΔnD were calculated from experimental data
according to the following equations:
x M + x M
x M
x M
It is clear in Figure 2 that the |VE| values for the binary system
of N4AC (1) + methanol (2) increase slightly with the
temperature, and a similar case can also be found for the other
three binary systems in Table 2. As the temperature increases,
the kinetic energy of pure components also increases, which
leads to a decrease in the interactions of the pure
components.53 The decreased interaction between pure organic
molecules results in greater interaction and packing efficiency
between alkanols and N4AC, so the contraction in volume
increases, and VE decreases. A similar phenomenon has been
observed by Zhou et al.;36 the |VE| values for binary mixtures of
naphthenic acid ILs and ethanol also increase slightly with the
temperature.
According to the literature, ILs are generally more viscous
than conventional solvents. In most applications, they can be
used in mixtures with other less viscous compounds. Therefore,
the viscosity of pure ILs and their mixtures with conventional
solvents is an important property which is primordial for each
industrial process. The viscosity of pure N4AC decreases with
the temperature from 771.694 mPa·s at 293.15 K to 222.241
mPa·s at 313.15 K, which are more viscous than pure 1-butyl-3-
methylimidazolium hexafluorophosphate20 and 2-hydroxyethy-
lammonium acetate IL,46 and less viscous than pure 1-methyl-3-
octylimidazolium nitrate21 at the same temperature. The
viscosities η as well as viscosity deviations Δη of N4AC with
alkanol binary mixtures are listed in Table 2. The viscosity
deviations Δη for binary mixtures of N4AC with methanol at
different temperatures are graphically represented in Figure 3,
which represents deviations from a rectilinear dependence of
viscosity on mole fraction. It can be observed in Figure 3 that
the Δη values are all negative over the whole concentration
range for N4AC (1) + methanol (2) mixtures and increase
sharply with the temperature. The Δη values for the other three
N4AC (1) + alkanols (2) mixtures have the same negative
deviation and similar temperature variation. A minimum
value in Δη is reached with a mole fraction of N4AC near to
0.7 for the four studied binary mixtures.
E
1
1
2
2
1
1
2
2
V =
−
−
ρ
ρ
ρ
(1)
(2)
(3)
1
2
Δη = η − (x η + x η )
1
2
2
1
ΔnD = nD − (x1nD,1 + x2nD,2
)
where x1 and x2 are mole fractions of components 1 and 2. ρ1,
ρ2, and ρ in eq 1, η1, η2, and η in eq 2, and nD1, nD2, and nD in eq
3 are the densities, viscosities, and refractive indices of pure
components 1, 2, and their mixtures, respectively. M1 and M2
are molecular weights of components 1 and 2.
The values of VE, Δη, and ΔnD of the above-mentioned
binary mixtures are also listed in Table 2. The results of VE, Δη,
and ΔnD were fitted by the Redlich−Kister polynomial
equation:
M
E
k
Y = x x
A (x − x )
k 1 2
∑
1 2
(4)
k=0
where YE ≡ (VE, Δη, or ΔnD), and the coefficients of Ak are
adjustable parameters which are obtained by fitting the
equations to the experimental values with a least-squares
method. M is the degree of the polynomial expansion. The
standard relative deviation, s, between the experimental and
calculated values was defined in the following equation:
s = [
((YE − YcEalcd)/YeExptl)2/N]1/2
∑
exptl
(5)
where N is the number of direct experimental data. The values
of the parameters Ak together with the standard relative
deviation s, for each property YE, are given in Table 3.
The excess molar volumes VE of mixtures versus the mole
fraction of N4AC with methanol, ethanol, n-propanol, and
n-butanol at 298.15 K are plotted in Figure 1, which shows that
the excess molar volumes are negative over the entire
composition range. As can be seen in Figure 1, the absolute
values of excess molar volumes (|VE|) follow the sequence:
methanol > ethanol > n-propanol > n-butanol. A minimum
value in VE of four binary mixtures is reached with mole fraction
of N4AC near to 0.3.
The refractive index nD can be used as a measure of the
electronic polarizability of a molecule and can provide useful
information when studying the interaction between molecules54
or their behavior in solution,55 and the refractive index
deviations ΔnD can be physically interpretable as the deviation
of the reduced free volume, which are negatively correlated to
VE values.35 The refractive index deviations of mixtures versus
the mole fraction of N4AC with methanol, ethanol, n-propanol,
and n-butanol at 298.15 K are plotted in Figure 4, which
presents a positive deviation from ideality over the whole
It is known that the excess molar volumes are the result of
several opposing effects. Interactions between like molecules
lead to increased VE values, while negative contributions to VE
arise from interactions between unlike molecules such as ion−
dipole and hydrogen bonding or structural effects such as
packing.21,37,51 N4AC is a typical protic IL and apt to form
hydrogen bonds with proton acceptors such as alkanols.
300
dx.doi.org/10.1021/je200707b | J. Chem. Eng.Data 2012, 57, 298−308

Journal of Chemical & Engineering Data
Article
Table 2. Densities ρ, Viscosities η, Refractive Indices nD, Excess Molar Volumes VE, Viscosity Deviations Δη, and Refractive
Index Deviations ΔnD for Binary Mixtures at Several Temperatures
ρ
η
VE
Δη
x1
g·cm−3
mPa·s
nD
cm−3·mol−1
mPa·s
ΔnD
xN4AC + (1 − x) Methanol
T = 293.15 K
0.0302
0.0597
0.1011
0.1992
0.3010
0.4023
0.4995
0.6524
0.7993
0.8988
0.81476
0.83265
0.85244
0.88485
0.90627
0.92099
0.93142
0.94329
0.95152
0.95588
0.883
1.237
−0.386
−0.626
0.844
−22.9648
−45.4017
1.933
−76.6241
4.825
−1.088
−1.128
−1.063
−0.948
−0.698
−0.423
−0.218
−149.4045
−221.6054
−287.6087
−340.9645
−388.2070
−360.5209
−275.1577
11.095
23.223
44.755
115.480
256.450
418.491
T = 298.15 K
1.3413
0.0302
0.0597
0.1011
0.1992
0.3010
0.4023
0.4995
0.6524
0.7993
0.8988
0.81030
0.82830
0.84833
0.88105
0.90266
0.91752
0.92803
0.94000
0.94831
0.95269
0.820
1.141
−0.398
−0.641
−0.869
−1.119
−1.160
−1.094
−0.975
−0.719
−0.438
−0.225
−16.2010
−32.0110
−53.9850
−105.0218
−155.2396
−200.5750
−236.4781
−264.1411
−240.8615
−178.5870
0.0113
0.0192
0.0283
0.0382
0.0416
0.0412
0.0367
0.0294
0.0172
0.0090
1.3526
1.759
1.3665
4.283
1.3878
9.608
1.4030
19.574
36.676
92.511
195.973
312.521
1.4144
1.4212
1.4316
1.4365
1.4398
T = 303.15 K
0.0302
0.0597
0.1011
0.1992
0.3010
0.4023
0.4995
0.6524
0.7993
0.8988
0.80581
0.82398
0.84420
0.87723
0.89904
0.91403
0.92464
0.93669
0.94507
0.94949
0.763
1.053
−0.410
−0.659
−0.892
−1.149
−1.191
−1.121
−0.999
−0.733
−0.443
−0.224
−11.7207
−23.1544
−39.0185
−75.7230
−111.5618
−143.4457
−168.1797
−190.2986
−166.5114
−114.4665
1.607
3.828
8.354
16.660
30.448
69.011
151.070
242.558
T = 308.15 K
0.0302
0.0597
0.1011
0.1992
0.3010
0.4023
0.4995
0.6524
0.7993
0.8988
0.80129
0.81963
0.84005
0.87338
0.89545
0.91053
0.92123
0.93339
0.94183
0.94630
0.712
0.975
−0.422
−0.678
−0.918
−1.182
−1.228
−1.153
−1.028
−0.755
−0.456
−0.233
−8.6494
−17.0785
−28.7527
−55.6512
−81.7225
−104.4784
−121.7915
−138.9049
−117.2549
−80.9676
1.474
3.437
7.294
14.337
25.586
53.465
118.320
183.852
T = 313.15 K
0.0302
0.0597
0.1011
0.1992
0.3010
0.4023
0.79674
0.81528
0.83589
0.86954
0.89177
0.90704
0.666
0.905
1.357
3.099
6.415
12.535
−0.434
−0.698
−0.944
−1.215
−1.260
−1.187
−6.4921
−12.8141
−21.5504
−41.5920
−60.8657
−77.2372
0.4995
0.6524
0.7993
0.8988
0.91783
0.93008
0.93859
0.94309
21.649
47.608
94.242
142.668
−1.058
−0.776
−0.468
−0.239
−89.6816
−97.6814
−83.6588
−57.3065
301
dx.doi.org/10.1021/je200707b | J. Chem. Eng.Data 2012, 57, 298−308

Journal of Chemical & Engineering Data
Article
Table 2. continued
ρ
η
VE
Δη
x1
g·cm−3
mPa·s
nD
cm−3·mol−1
mPa·s
ΔnD
xN4AC + (1 − x) Ethanol
T = 293.15 K
0.0319
0.0608
0.0999
0.1977
0.2965
0.4008
0.5005
0.6454
0.8019
0.9009
0.80512
0.81726
0.83176
0.86095
0.88307
0.90146
0.91565
0.93209
0.94597
0.95334
1.644
2.184
−0.243
−0.390
−0.533
−0.740
−0.780
−0.752
−0.679
−0.520
−0.308
−0.172
−24.1639
−45.8653
−75.1921
−146.7545
−215.7867
−283.4227
−337.6563
−385.3782
−354.8651
−220.0131
3.042
6.773
13.923
26.605
49.217
113.109
264.170
475.323
T = 298.15 K
1.3681
0.0319
0.0608
0.0999
0.1977
0.2965
0.4008
0.5005
0.6454
0.8019
0.9009
0.80093
0.81317
0.82777
0.85719
0.87943
0.89794
0.91221
0.92875
0.94274
0.95015
1.488
1.959
−0.250
−0.401
−0.549
−0.763
−0.803
−0.776
−0.699
−0.535
−0.318
−0.178
−17.0247
−32.2936
−52.9057
−102.9919
−150.9288
−197.3636
−233.8250
−262.1090
−236.5043
−144.4751
0.0058
0.0084
0.0124
0.0204
0.0230
0.0223
0.0207
0.0160
0.0098
0.0052
1.3731
2.707
1.3804
5.903
1.3965
11.878
22.281
40.200
90.902
201.813
347.838
1.4073
1.4152
1.4219
1.4292
1.4360
1.4396
T = 303.15 K
0.0319
0.0608
0.0999
0.1977
0.2965
0.4008
0.5005
0.6454
0.8019
0.9009
0.79671
0.80904
0.82374
0.85335
0.87576
0.89440
0.90876
0.92539
0.93948
0.94694
1.349
1.764
−0.255
−0.411
−0.563
−0.782
−0.824
−0.795
−0.716
−0.544
−0.321
−0.176
−12.3109
−23.3317
−38.1960
−74.1532
−108.2677
−140.9562
−166.0960
−183.8623
−162.2535
−97.1578
2.420
5.176
10.232
18.841
33.212
72.834
156.424
260.752
T = 308.15 K
0.0319
0.0608
0.0999
0.1977
0.2965
0.4008
0.5005
0.6454
0.8019
0.9009
0.79246
0.80488
0.81969
0.84949
0.87209
0.89081
0.90530
0.92203
0.93622
0.94374
1.226
1.593
−0.262
−0.423
−0.579
−0.803
−0.850
−0.816
−0.737
−0.560
−0.332
−0.184
−9.0580
−17.1690
−28.0957
−54.4088
−79.1719
−102.5615
−120.1507
−131.2680
−113.9790
−67.7049
2.171
4.557
8.831
16.056
27.757
59.183
122.419
197.777
T = 313.15 K
0.0319
0.0608
0.0999
0.1977
0.2965
0.4008
0.5005
0.6454
0.8019
0.9009
0.78816
0.80068
0.81560
0.84568
0.86839
0.88718
0.90183
0.91866
0.93294
0.94053
1.117
1.442
−0.267
−0.433
−0.595
−0.831
−0.875
−0.835
−0.759
−0.576
−0.340
−0.189
−6.7910
−12.8629
−21.0788
−40.6301
−58.8595
−75.9076
−88.3873
−95.3535
−81.1720
−47.6642
1.908
4.013
7.695
13.748
23.371
48.507
97.361
152.815
302
dx.doi.org/10.1021/je200707b | J. Chem. Eng.Data 2012, 57, 298−308

Journal of Chemical & Engineering Data
Article
Table 2. continued
ρ
η
VE
Δη
x1
g·cm−3
mPa·s
nD
cm−3·mol−1
mPa·s
ΔnD
xN4AC + (1 − x) n-Propanol
T = 293.15 K
0.0315
0.0601
0.0977
0.1980
0.3002
0.4021
0.4970
0.6487
0.7990
0.8981
0.81410
0.82282
0.83338
0.85748
0.877710
0.89470
0.90839
0.92709
0.94252
0.95147
2.862
3.515
−0.158
−0.261
−0.361
−0.500
−0.534
−0.508
−0.453
−0.343
−0.206
−0.118
−23.5688
−44.9205
−72.6985
−145.9776
−215.7611
−280.0752
−337.1474
−392.8605
−372.3518
−248.0804
4.733
8.602
17.499
31.539
47.475
108.492
244.690
445.203
T = 298.15 K
1.3875
0.0315
0.0601
0.0977
0.1980
0.3002
0.4021
0.4970
0.6487
0.7990
0.8981
0.81013
0.81891
0.82952
0.85376
0.87410
0.89119
0.90494
0.92374
0.93927
0.94825
2.496
3.158
−0.160
−0.266
−0.368
−0.511
−0.547
−0.521
−0.465
−0.352
−0.213
−0.120
−16.6015
−31.5062
−51.0623
−102.3873
−150.6546
−194.7765
−233.8146
−267.8654
−250.1062
−164.3432
0.0022
0.0042
0.0061
0.0094
0.0110
0.0113
0.0108
0.0087
0.0055
0.0029
1.3912
4.116
1.3953
7.371
1.4045
14.768
26.079
38.692
87.224
186.830
326.532
1.4122
1.4185
1.4236
1.4305
1.4362
1.4395
T = 303.15 K
0.0315
0.0601
0.0977
0.1980
0.3002
0.4021
0.4970
0.6487
0.7990
0.8981
0.80612
0.81495
0.82563
0.85000
0.87046
0.88765
0.90148
0.92037
0.93601
0.94503
2.202
2.773
−0.160
−0.268
−0.374
−0.521
−0.558
−0.532
−0.474
−0.356
−0.213
−0.117
−11.9914
−22.7281
−36.8060
−73.6795
−107.9660
−138.5154
−166.5192
−187.8320
−168.9173
−112.0465
3.595
6.367
12.513
22.228
31.742
70.415
148.780
244.830
T = 308.15 K
0.0315
0.0601
0.0977
0.1980
0.3002
0.4021
0.4970
0.6487
0.7990
0.8981
0.80209
0.81095
0.82170
0.84622
0.86680
0.88410
0.89801
0.91700
0.93273
0.94183
1.955
2.447
−0.163
−0.272
−0.381
−0.534
−0.572
−0.547
−0.489
−0.366
−0.221
−0.123
−8.8301
−16.7171
−27.0489
−54.0913
−78.8863
−100.9044
−120.7865
−135.0163
−118.8125
−78.3126
3.157
5.493
10.660
18.480
26.400
56.622
116.881
186.414
T = 313.15 K
0.0315
0.0601
0.0977
0.1980
0.3002
0.4021
0.4970
0.6487
0.7990
0.8981
0.79801
0.80691
0.81772
0.84242
0.86311
0.88052
0.89453
0.91360
0.92943
0.93861
1.672
2.167
−0.163
−0.274
−0.386
−0.547
−0.586
−0.562
−0.503
−0.374
−0.224
−0.128
−6.6855
−12.5116
−20.1799
−40.3997
−58.6172
−74.5582
−89.1251
−98.0204
−84.8799
−55.0787
2.828
4.770
9.154
15.721
22.126
46.763
93.136
144.838
303
dx.doi.org/10.1021/je200707b | J. Chem. Eng.Data 2012, 57, 298−308

Journal of Chemical & Engineering Data
Article
Table 2. continued
ρ
η
VE
Δη
x1
g·cm−3
mPa·s
nD
cm−3·mol−1
mPa·s
ΔnD
xN4AC + (1 − x) n-Butanol
T = 293.15 K
0.0290
0.0583
0.1003
0.1981
0.2981
0.3990
0.4970
0.6489
0.7984
0.9003
0.81708
0.82415
0.83362
0.85355
0.87149
0.88771
0.90199
0.92184
0.93921
0.94980
3.564
4.397
−0.101
−0.181
−0.260
−0.355
−0.372
−0.349
−0.302
−0.221
−0.137
0.056
−21.7184
−43.4125
−74.4640
−145.4629
−214.9970
−281.3748
−334.7907
−394.0326
−391.7172
−305.5476
5.588
9.789
17.144
28.334
50.227
107.737
225.041
389.538
T = 298.15 K
1.3999
0.0290
0.0583
0.1003
0.1981
0.2981
0.3990
0.4970
0.6489
0.7984
0.9003
0.81328
0.82036
0.82988
0.84990
0.86792
0.88421
0.89853
0.91848
0.93595
0.94658
3.190
3.806
−0.100
−0.180
−0.262
−0.361
−0.379
−0.356
−0.309
−0.224
−0.142
−0.056
−15.2002
−30.5182
−52.3082
−101.9327
−150.2952
−196.0928
−231.8309
−269.3949
−266.1509
−204.1675
0.0013
0.0024
0.0035
0.0052
0.0062
0.0063
0.0058
0.0047
0.0031
0.0018
1.4023
4.823
1.4053
8.389
1.4115
14.412
23.481
41.010
86.028
170.607
287.993
1.4170
1.4217
1.4256
1.4314
1.4366
1.4399
T = 303.15 K
0.0290
0.0583
0.1003
0.1981
0.2981
0.3990
0.4970
0.6489
0.7984
0.9003
0.80945
0.81655
0.82611
0.84622
0.86433
0.88069
0.89509
0.91512
0.93268
0.94337
2.787
3.318
−0.100
−0.181
−0.264
−0.366
−0.386
−0.362
−0.314
−0.225
−0.139
−0.052
−10.9738
−22.0145
−37.7288
−73.3708
−107.8368
−140.2626
−165.3332
−189.3806
−179.4815
−140.9575
4.165
7.151
12.181
19.600
33.212
69.137
138.102
216.861
T = 308.15 K
0.0290
0.0583
0.1003
0.1981
0.2981
0.3990
0.4970
0.6489
0.7984
0.9003
0.80557
0.81270
0.82223
0.84252
0.86072
0.87717
0.89162
0.91175
0.92940
0.94016
2.455
2.908
−0.099
−0.181
−0.259
−0.373
−0.395
−0.373
−0.323
−0.231
−0.144
−0.057
−8.0713
−16.1914
−27.7341
−53.8657
−78.8623
−102.2691
−118.9783
−135.5535
−125.8288
−98.2847
3.636
6.123
10.388
16.501
28.451
56.308
109.794
167.147
T = 313.15 K
0.0290
0.0583
0.1003
0.1981
0.2981
0.3990
0.4970
0.6489
0.7984
0.9003
0.80167
0.80882
0.81846
0.83878
0.85708
0.87362
0.88815
0.90837
0.92610
0.93693
2.164
2.592
−0.098
−0.181
−0.268
−0.378
−0.404
−0.382
−0.333
−0.238
−0.146
−0.058
−6.0475
−12.0846
−20.7613
−40.2175
−58.6881
−75.8434
−87.4808
−99.0834
−90.3205
−70.6120
3.170
5.297
8.894
14.002
23.979
45.886
87.652
129.841
composition range for all of these systems and are negatively
observed is obtained according this order: methanol > ethanol >
n-propanol > n-butanol. A maximum value in ΔnD of four
correlated to VE values. The magnitude of deviation ΔnD
304
dx.doi.org/10.1021/je200707b | J. Chem. Eng.Data 2012, 57, 298−308

Journal of Chemical & Engineering Data
Article
Table 3. Fitted Parameters of Equation 4 and Standard Relative Deviation (s) for the Binary Mixtures at Several Temperatures
A0
A1
A2
A3
s
xN4AC + (1 − x) Methanol
T = 293.15 K
2.4123
VE/cm3·mol−1
Δη/mPa·s
−3.7112
−1341.4740
−3.2263
3.3343
0.0565
0.0493
−900.0886
T = 298.15 K
2.4770
−824.6006
−643.7715
VE/cm3·mol−1
Δη/mPa·s
ΔnD
−3.8194
−931.2759
0.1483
−3.3242
−485.0483
0.0811
3.4205
−337.1464
−0.0846
0.0560
0.0420
0.0003
−588.8279
−0.0806
T = 303.15 K
VE/cm3·mol−1
Δη/mPa·s
−3.9109
−673.5456
2.5645
−3.3827
−252.7125
3.5523
0.0562
0.0094
−440.9845
T = 308.15 K
2.6490
−107.3166
VE/cm3·mol−1
Δη/mPa·s
−4.0252
−490.8964
−3.4878
−160.9691
3.6179
0.0566
0.0116
−315.5875
T = 313.15 K
2.7170
−49.1407
VE/cm3·mol−1
Δη/mPa·s
−4.1393
−356.8749
−3.5767
−109.5879
3.7449
0.0573
0.0162
−200.0164
xN4AC + (1 − x) Ethanol
T = 293.15 K
1.6975
−62.2541
VE/cm3·mol−1
Δη/mPa·s
−2.6755
−1357.0758
−1.8878
−528.3617
1.4925
0.0441
0.0194
−1012.1704
T = 298.15 K
1.7639
−78.2681
VE/cm3·mol−1
Δη/mPa·s
ΔnD
−2.7533
−938.2855
0.0826
−1.9618
−303.8565
0.0303
1.4994
−25.9110
0.0002
0.0431
0.0187
0.0004
−657.0206
−0.0535
T = 303.15 K
VE/cm3·mol−1
Δη/mPa·s
−2.8189
−666.8658
1.8338
−1.9691
−173.2521
1.5533
0.0417
0.0205
−443.3968
T = 308.15 K
1.8871
11.2742
VE/cm3·mol−1
Δη/mPa·s
−2.9001
−482.0299
−2.0315
−105.7770
1.5670
0.0418
0.0190
−301.8621
T = 313.15 K
1.9561
13.8411
VE/cm3·mol−1
Δη/mPa·s
−2.9796
−354.5107
−2.1032
−61.4639
1.5837
0.0403
0.0187
−208.6584
−18.0397
xN4AC + (1 − x) n-Propanol
T = 293.15 K
VE/cm3·mol−1
Δη/mPa·s
−1.7910
−1351.8517
1.2331
−1.3074
0.8903
0.0373
0.0102
−1065.4344
T = 298.15 K
−698.7149
−221.1393
VE/cm3·mol−1
Δη/mPa·s
ΔnD
−1.8401
−935.5161
0.0429
1.2607
−702.1464
−0.0181
−1.3251
−427.0915
0.0109
0.8939
−121.3448
−0.0080
0.0321
0.0109
0.0001
T = 303.15 K
VE/cm3·mol−1
Δη/mPa·s
−1.8753
−663.8870
1.3197
−1.2928
−254.0472
0.8808
0.0273
0.0075
−468.7216
−60.5184
T = 308.15 K
VE/cm3·mol−1
Δη/mPa·s
−1.9298
−481.7244
1.3632
−1.3195
−159.4885
0.8295
0.0286
0.0086
−325.9566
−27.0502
T = 313.15 K
VE/cm3·mol−1
Δη/mPa·s
−1.9820
−354.6676
1.4284
−1.3147
−98.4255
0.7450
0.0283
0.0089
−227.8272
−7.9731
xN4AC + (1 − x) n-Butanol
T = 293.15 K
VE/cm3·mol−1
Δη/mPa·s
−1.2071
−1320.3929
0.9332
−0.8927
0.7271
0.0279
0.0649
−969.9828
T = 298.15 K
−1127.7459
−914.5164
VE/cm3·mol−1
Δη/mPa·s
ΔnD
−1.2329
−915.0510
0.0232
0.9635
−644.5952
−0.0113
−0.8884
−732.1942
0.0093
0.6742
−598.2069
−0.0014
0.0373
0.0598
0.0001
305
dx.doi.org/10.1021/je200707b | J. Chem. Eng.Data 2012, 57, 298−308

Journal of Chemical & Engineering Data
Article
Table 3. continued
A0
A1
A2
A3
s
T = 303.15 K
VE/cm3·mol−1
Δη/mPa·s
−1.2525
−650.8554
1.0058
−0.8437
−467.1493
0.6724
0.0432
0.0653
−424.4814
−405.0951
T = 308.15 K
VE/cm3·mol−1
Δη/mPa·s
−1.2903
−470.06335
1.0607
−0.8212
−310.9103
0.5117
0.0404
0.0613
−289.5268
−275.2953
T = 313.15 K
VE/cm3·mol−1
Δη/mPa·s
−1.3281
−346.8387
1.0743
−0.8073
−214.7319
0.5393
0.0365
0.0600
−202.1969
−195.5612
Figure 1. Excess molar volume VE vs mole fraction for {x1N4AC +
Figure 3. Viscosity deviations Δη vs mole fraction for {x1N4AC +
□
○
▽
(1 − x1) alkanol} mixtures at 298.15 K: , methanol; , ethanol;
,
◊
□
○
▽
(1 − 1) methanol} mixtures: , 293.15 K; , 298.15 K; , 303.15 K;
,
◊
n-propanol; , n-butanol. The symbols represent experimental values,
and the solid curves represent the values calculated from the Redlich−
Kister equation.
△
308.15 K; , 313.15 K. The symbols represent experimental values,
and the solid curves represent the values calculated from the Redlich−
Kister equation.
Figure 2. Excess molar volume VE vs mole fraction for {x1N4AC +
Figure 4. Refractive index deviations ΔnD vs mole fraction for
□
○
▽
(1 − x1) methanol} mixtures: , 293.15 K; , 298.15 K; , 303.15 K;
□
○
,
{x1N4AC + (1 − x1) alkanol} mixtures at 298.15 K: , methanol;
◊
△
, 308.15 K; , 313.15 K. The symbols represent experimental values,
◊
▽
ethanol;
, n-propanol; , n-butanol. The symbols represent
and the solid curves represent the values calculated from the Redlich−
Kister equation.
experimental values, and the solid curves represent the values
calculated from the Redlich−Kister equation.
binary systems is also reached with mole fraction of N4AC near
x1 ≈ 0.3, which is consistent with the VE. Compared with the
maximum absolute values of VE and ΔnD of the studied systems
at 298.15 K, we can find that the high |VE| values (methanol >
ethanol > n-propanol > n-butanol) correspond to the high ΔnD
values (methanol > ethanol > n-propanol > n-butanol). As it
stated above, ΔnD and VE must be somehow related: if VE is
negative, then there will be less available free volume than in an
ideal solution, and photons will be more likely to interact with
the molecules or ions constituting the mixture. As a result, light
will travel at a weaker velocity in the concerned medium, and its
refractive index will be higher than in an ideal solution.35
4. CONCLUSIONS
In the present research, the experimental densities and
viscosities of N4AC and its binary systems with methanol,
ethanol, n-propanol, and n-butanol have been measured at
temperatures (293.15, 298.15, 303.15, 308.15, and 313.15) K
and atmospheric pressure. The refractive indices of above-
mentioned mixtures have been measured at 298.15 K and
atmospheric pressure. The excess molar volumes VE, viscosity
deviations Δη, and refractive index deviations ΔnD have been
obtained from experimental data and fitted by the Redlich−
Kister equation. The estimated coefficients and standard
306
dx.doi.org/10.1021/je200707b | J. Chem. Eng.Data 2012, 57, 298−308

Journal of Chemical & Engineering Data
Article
trifluoromethanesulfonate. J. Chem. Eng. Data 2007, 52, 141−
147.
(15) Mokhtarani, B.; Gmehling, J. (Vapour + liquid) equilibria of
ternary systems with ionic liquids using headspace gas chromatog-
raphy. J. Chem. Thermodyn. 2010, 42, 1036−1038.
relative deviation values were also presented. It was found that
the excess molar volumes of N4AC + alkanol binary mixtures
were negative, and their absolute values increased slightly with
temperature and decreased with increasing the alcohol chain
length. Meanwhile, the refractive index deviations have positive
deviations from ideal solution and also decreased with
increasing the alcohol chain length. When the mole fraction
of N4AC near x1 = 0.3, both VE and ΔnD of N4AC + alkanol
binary mixtures have extreme points. The viscosity deviations of
the studied binary mixtures have negative deviations, and their
absolute values decreased sharply as increasing the temperature,
with the minima lying nearly at x1 = 0.7.
(16) Huang, J.; Luo, H.; Liang, C.; Jiang, D.; Dai, S. Advanced liquid
membranes based on novel ionic liquids for selective separation of
olefin/parafrin via olefin-facilitated transport. Ind. Eng. Chem. Res.
2008, 47, 881−888.
(17) Mahurin, S. M.; Lee, J. S.; Baker, G. A.; Luo, H. M.; Dai, S.
Performance of nitrile-containing anions in task-specific ionic liquids
for improved CO2/N2 separation. J. Membr. Sci. 2010, 353, 177−183.
́
(18) Gomez, E.; Dominguez, I.; Calvar, N.; Domínguez, A.
Separation of benzene from alkanes by solvent extraction with 1-
ethylpyridinium ethylsulfate ionic liquid. J. Chem. Thermodyn. 2010,
42, 1234−1239.
(19) Li, W.; Zhang, Z.; Han, B.; Hu, S.; Xie, Y.; Yang, G. Effect of
water and organic solvents on the ionic dissociation of ionic liquids.
J. Phys. Chem. B 2007, 111, 6452−6456.
AUTHOR INFORMATION
■
Corresponding Author
*E-mail: lihr@zju.edu.cn. Fax: +86 571 87951895.
Funding
(20) Fan, W.; Zhou, Q.; Sun, J.; Zhang, S. Density, excess molar
volume, and viscosity for the methyl methacrylate + 1-butyl-3-
methylimidazolium hexafluorophosphate ionic liquid binary system at
atmospheric pressure. J. Chem. Eng. Data 2009, 54, 2307−2311.
(21) Mokhtarani, B.; Sharifi, A.; Mortaheb, H. R.; Mirzaei, M.; Mafi,
M.; Sadeghian, F. Densities and viscosities of pure 1-methyl-3-
octylimidazolium nitrate and its binary mixtures with alcohols at
several temperatures. J. Chem. Eng. Data 2010, 55, 3901−3908.
(22) Fan, W.; Zhou, Q.; Zhang, S.; Yan, R. Excess molar volume and
viscosity deviation for the methanol + methyl methacrylate binary
system at T = (283.15 to 333.15) K. J. Chem. Eng. Data 2008, 53,
1836−1840.
(23) Zhang, S.; Li, M.; Chen, H.; Wang, J.; Zhang, J.; Zhang, M.
Determination of physical properties for the binary system of 1-ethyl-
3-methylimidazolium tetrafluoroborate + H2O. J. Chem. Eng. Data
2004, 49, 760−764.
(24) Mokhtarani, B.; Mojtahedi, M. M.; Mortaheb, H. R.; Mafi, M.;
Yazdani, F.; Sadeghian, F. Densities, refractive indices, and viscosities
of the ionic liquids 1-methyl-3-octylimidazolium tetrafluoroborate and
1-methyl-3-butylimidazolium perchlorate and their binary mixtures
with ethanol at several temperatures. J. Chem. Eng. Data 2008, 53,
677−682.
This research was supported financially by the National Natural
Science Foundation of Zhejiang Province (No. Y4090453) and
the National Science Foundation of China (Nos. 20773109 and
20704035).
REFERENCES
■
(1) Welton, T. Room-temperature ionic liquids. Solvents for
synthesis and catalysis. Chem. Rev. 1999, 99, 2071−2083.
(2) Lee, J. S.; Mayes, R. T.; Luo, H. M.; Dai, S. Ionothermal
carbonization of sugars in a protic ionic liquid under ambient
conditions. Carbon 2010, 48, 3364−3368.
(3) Guan, W.; Wang, C.; Yun, X.; Hu, X.; Wang, Y.; Li, H. A mild and
efficient oxidation of 2,3,6-trimethylphenol to trimethyl-1,4-benzoqui-
none in ionic liquids. Catal. Commun. 2008, 9, 1979−1981.
(4) Wang, C.; Guan, W.; Xie, P.; Yun, X.; Li, H.; Hu, X.; Wang, Y.
Effects of ionic liquids on the oxidation of 2,3,6-trimethylphenol to
trimethyl-1,4-benzoquinone under atmospheric oxygen. Catal. Com-
mun. 2009, 10, 725−727.
(5) Wang, Y.; Li, H.; Wang, C.; Jiang, H. Ionic liquids as catalytic
green solvents for cracking reactions. Chem. Commun. 2004, 17,
1938−1939.
(25) Mokhtarani, B.; Sharifi, A.; Mortaheb, H. R.; Mirzaei, M.; Mafi,
M.; Sadeghian, F. Density and viscosity of 1-butyl-3-methylimidazo-
lium nitrate with ethanol, 1-propanol, or 1-butanol at several
temperatures. J. Chem. Thermodyn. 2009, 41, 1432−1438.
(26) Wang, J. J.; Tian, Y.; Zhao, Y.; Zhuo, K. A volumetric and
viscosity study for the mixtures of 1-n-butyl-3-methylimidazolium
tetrafluoroborate ionic liquid with acetonitrile, dichloromethane,
2-butanone and N,N-dimethylformamide. Green Chem. 2003, 5,
618−622.
(6) Wasserscheid, P.; Keim, W. Ionic liquids - New “solutions” for
transition metal catalysis. Angew. Chem., Int. Ed. 2000, 39, 3772−3789.
(7) Xu, X.; Wang, C.; Li, H.; Wang, Y.; Sun, W.; Shen, Z. Effects of
imidazolium salts as cocatalysts on the copolymerization of CO2 with
epoxides catalyzed by (salen)(CrCl)-Cl-III complex. Polymer 2007, 48,
3921−3924.
(8) Wang, C.; Luo, H.; Jiang, D.; Li, H.; Dai, S. Carbon dioxide
capture by superbase-derived protic ionic liquids. Angew. Chem., Int.
Ed. 2010, 49, 5978−5981.
(27) Rebelo, L. P. N; Najdanovic-Visak, V.; Visak, Z. P.; da Ponte, M.
N.; Szydlowski, J.; Cerdeirina, C. A.; Troncoso, J.; Romani, L.;
Esperanca, J. M. S. S.; Guedes, H. J. R.; de Sousa, H. C. A detailed
thermodynamic analysis of [C(4)mim][BF4] + water as a case study to
model ionic liquid aqueous solutions. Green Chem. 2004, 6, 369−6381.
(28) Mohammed, T. Z.; Hemaya, S. Volumetric and Speed of Sound
of Ionic Liquid, 1-Butyl-3-methylimidazolium hexafluorophosphate
with acetonitrile and methanol at T = (298.15 to 318.15) K. J. Chem.
Eng. Data 2005, 50, 1694−1699.
(29) Mokhtarani, B.; Sharifi, A.; Mortaheb, H. R.; Mirzaei, M.; Mafi,
M.; Sadeghian, F. Density and viscosity of pyridinium-based ionic
liquids and their binary mixtures with water at several temperatures.
J. Chem. Thermodyn. 2009, 41, 323−329.
(9) Wang, C.; Mahurin, S. M.; Luo, H.; Baker, G. A.; Li, H. R.; Dai, S.
Reversible and robust CO2 capture by equimolar task-specific ionic
liquid-superbase mixtures. Green Chem. 2010, 12, 870−874.
(10) Wang, C.; Luo, H.; Luo, X.; Li, H.; Dai, S. Equimolar CO2
capture by imidazolium-based ionic liquids and superbase systems.
Green Chem. 2010, 12, 2019−2023.
(11) Huang, J.; Baker, G. A.; Luo, H.; Hong, K.; Li, Q.; Bjerrum,
N. J.; Dai, S. Bronsted acidic room temperature ionic liquids derived
from N,N-dimethylformamide and similar protophilic amides. Green
Chem. 2006, 8, 599−602.
(12) Sun, X.; Dai, S. Electrochemical investigations of ionic liquids
with vinylene carbonate for applications in rechargeable lithium ion
batteries. Electrochim. Acta 2010, 55, 4618−4626.
(30) Sanchez, L. G.; Espel, J. R.; Onink, F.; Meindersma, G. W.; De
Haan, A. B. Density, viscosity, and surface tension of synthesis grade
imidazolium, pyridinium, and pyrrolidinium based room temperature
ionic liquids. J. Chem. Eng. Data 2009, 54, 2803−2812.
(31) Gomez, E.; Calvar, N.; Dominguez, A.; Macedo, E. A. Synthesis
and temperature dependence of physical properties of four
(13) Li, Q.; Zhang, J.; Lei, Z.; Zhu, J.; Zhu, J.; Huang, X. Selection of
ionic liquids as entrainers for the separation of ethyl acetate and
ethanol. Ind. Eng. Chem. Res. 2009, 48, 9006−9012.
(14) Orchilles, A. V.; Miguel, P. J.; Vercher, E.; Martinez-Andreu, A.
Ionic liquids as entrainers in extractive distillation: Isobaric vapor-
liquid equilibria for acetone + methanol + 1-ethyl-3-methylimidazolium
307
dx.doi.org/10.1021/je200707b | J. Chem. Eng.Data 2012, 57, 298−308

Journal of Chemical & Engineering Data
Article
pyridinium-based ionic liquids: Influence of the size of the cation.
J. Chem. Thermodyn. 2010, 42, 1324−1329.
(51) Yu, Z.; Gao, H.; Wang, H.; Chen, L. Densities, viscosities, and
refractive properties of the binary mixtures of the amino acid ionic
liquid [bmim][Ala] with methanol or benzylalcohol at T = (298.15 to
313.15) K. J. Chem. Eng. Data 2011, 56, 2877−2883.
(52) Gonzalez, E. J.; Alonso, L.; Dominguez, A. Physical properties of
binary mixtures of the ionic liquid 1-methyl-3-octylimidazolium
chloride with methanol, ethanol, and 1-propanol at T = (298.15,
313.15, and 328.15) K and at P = 0.1 MPa. J. Chem. Eng. Data 2006,
51, 1446−1452.
(53) Zhong, Y.; Wang, H.; Diao, K. Densities and excess volumes of
binary mixtures of the ionic liquid 1-butyl-3-methylimidazolium
hexafluorophosphate with aromatic compound at T = (298.15 to
313.15) K. J. Chem. Thermodyn 2007, 39, 291−296.
(54) Hirschfelder, J. O.; Curtiss, C. F.; Bird, R. B. Molecular theory of
gases and liquids; Wiley: London, 1969.
(32) Xu, Y.; Huang, C.; Li, H. Excess Molar Volume, Refractive index
and viscosity of N-butylpyridinium tetrafluoroborate ionic liquid +
methanol binary system. J. Chem. Eng. Chin. Univ. 2011, 25, 370−375.
(33) Kilaru, P.; Baker, G. A.; Scovazzo, P. Density and surface tension
measurements of imidazolium-, quaternary phosphonium-, and
ammonium-based room-temperature ionic liquids: Data and correla-
tions. J. Chem. Eng. Data 2007, 52, 2306−2314.
(34) Tariq, M.; Forte, P. A. S.; Gomes, M. F. C.; Lopes, J. N. C.;
Rebelo, L. P. N. Densities and refractive indices of imidazolium- and
phosphonium-based ionic liquids: Effect of temperature, alkyl chain
length, and anion. J. Chem. Thermodyn. 2009, 41, 790−798.
(35) Anouti, M.; Vigeant, A.; Jacquemin, J.; Brigouleix, C.;
Lemordant, D. Volumetric properties, viscosity and refractive index
of the protic ionic liquid, pyrrolidinium octanoate, in molecular
solvents. J. Chem. Thermodyn. 2010, 42, 834−845.
(36) Zhou, Q.; Song, Y.; Yu, Y; He, H.; Zhang, S. Density and excess
molar volume for binary mixtures of naphthenic acid ionic liquids and
ethanol. J. Chem. Eng. Data 2010, 55, 1105−1108.
(37) Jiang, H.; Wang, C.; Li, H.; Wang, Y. Preparation of
dialkoxypropanes in simple ammonium ionic liquids. Green Chem.
2006, 8, 1076−1079.
(55) Israelichvili, J. N. Intermolecular and surface forces, 2nd ed.;
Academic Press: London, 1992.
(38) Wang, C.; Guo, L.; Li, H.; Wang, Y.; Weng, J.; Wu, L.
Preparation of simple ammonium ionic liquids and their application in
the cracking of dialkoxypropanes. Green Chem. 2006, 8, 603−607.
(39) Weng, J.; Wang, C.; Li, H.; Wang, Y. Novel quaternary
ammonium ionic liquids and their use as dual solvent-catalysts in the
hydrolytic reaction. Green Chem. 2006, 8, 96−99.
(40) Wang, C.; Zhao, W.; Li, H.; Guo, L. Solvent-free synthesis of
unsaturated ketones by the Saucy-Marbet reaction using simple
ammonium ionic liquid as a catalyst. Green Chem. 2009, 11, 843−847.
(41) Zhu, X.; Wang, Y.; Li, H. The structural organization in aqueous
solutions of ionic liquids. AIChE J. 2009, 55, 198−205.
(42) Alvarez, V. H.; Mattedi, S.; Pastor, M. M.; Aznar, M.; Iglesias, M.
Thermophysical properties of binary mixtures of {ionic liquid
2-hydroxy ethylammonium acetate + (water, methanol, or ethanol)}.
J. Chem. Thermodyn. 2011, 43, 997−1010.
(43) Iglesias, M.; Torres, A.; Gonzalez-Olmos, R.; Salvatierra, D.
Effect of temperature on mixing thermodynamics of a new ionic liquid:
{2-hydroxy ethylammonium formate (2-HEAF) + short hydroxylic
solvents}. J. Chem. Thermodyn. 2008, 40, 119−133.
(44) Kurnia, K. A.; Taib, M. M.; Mutalib, M. I. A.; Murugesan, T.
Densities, refractive indices and excess molar volumes for binary
mixtures of protic ionic liquids with methanol at T = 293.15 to 313.15
K. J. Mol. Liq. 2011, 159, 211−219.
(45) Taib, M. M.; Murugesan, T. Densities and excess molar volumes
of binary mixtures of bis(2-hydroxyethyl)ammonium acetate + water
and monoethanolamine + bis(2-hydroxyethyl)ammonium acetate at
temperatures from (303.15 to 353.15) K. J. Chem. Eng. Data 2010, 55,
5910−5913.
(46) Kurnia, K. A.; Wilfred, C. D.; Murugesan, T. Thermophysical
properties of hydroxyl ammonium ionic liquids. J. Chem. Thermodyn.
2009, 41, 517−521.
(47) Wang, C.; Li, H.; Zhu, L.; Han, S. Excess molar volume of
binary mixtures of dehydrolinalool + alkanols at 308.15 K. Fluid Phase
Equilib. 2001, 189, 129−133.
(48) Wang, Y.; Yan, W. Excess Molar Volumes of 1,3-diethyl
propanedioate with methanol, ethanol, propan-1-ol, propan-2-ol, butan-
2-ol, 2-methyl-propan-1-ol, and pentan-1-ol at T = (288.15, 298.15,
313.15, and 328.15) K. J. Chem. Eng. Data 2010, 55, 4029−4032.
(49) Trenzado, J.; Romano, E.; Segade, L.; Caro, M. N.; Gonzal
́
ez, E.;
Galvan, S. Densities and viscosities of four binary diethyl carbonate +
́
1-alcohol systems from (288.15 to 313.15) K. J. Chem. Eng. Data 2011,
56, 2841−2848.
(50) Sadeghi, R.; Azizpour, S. Volumetric, compressibility, and viscometric
measurements of binary mixtures of poly(vinylpyrrolidone) + water, +
methanol, + ethanol, + acetonitrile, + 1-propanol, + 2-propanol, and + 1-
butanol. J. Chem. Eng. Data 2011, 56, 167−174.
308
dx.doi.org/10.1021/je200707b | J. Chem. Eng.Data 2012, 57, 298−308