Excess Molar Volume and Viscosity Deviation of [C2mim][NTf2]/[C4mim][NTf2] + DMC/DEC

Article abstract of DOI:10.1021/acs.jced.8b00591

Two hydrophobic ionic liquids (ILs) 1-alkyl-3-methylimidazolium bis[(trifluoromethyl)sulfonyl]imide ([C₂mim][NTf₂] and [C₄mim][NTf₂]) were synthesized. The binary mixtures of the two ILs were prepared with dimethyl carbonate (DMC) or diethyl carbonate (DEC) over the entire mole fraction range, respectively. The density and viscosity of the binary mixtures were determined by an automated DMA 5000 M and a Lovis 2000 ME Anton Paar Rotational Stabinger Viscometer at temperatures ranging from 288.15 to 328.15 K. The uncertainties of the density and viscosity are u_r(δ) = 0.00120 and u_r(δ) = 0.01. The excess molar volumes and viscosity deviations were calculated for the four binary mixtures by the measurement values. The effects of the extension of the alkyl chain of the cation and anion on the above properties are discussed. The effects of the methyl introduction on the cation was also discussed with the literature. The excess molar volumes and viscosity deviations were fitted versus mole fraction according to the Redlich-Kister equation. The thermal expansion coefficients of the systems were calculated according to the density values.

Full text of DOI:10.1021/acs.jced.8b00591

Article
pubs.acs.org/jced
Cite This: J. Chem. Eng. Data XXXX, XXX, XXX−XXX
Excess Molar Volume and Viscosity Deviation of [C2mim][NTf2]/
[C4mim][NTf2] + DMC/DEC
Qingshan Liu,*,†,‡ Liwei Zhao,† Qige Zheng,‡ Lin Mou,‡ and Pengfei Zhang‡
‡
†College of Land and Environment, and College of Science, Shenyang Agricultural University, Shenyang 110866,
People’s Republic of China
S
* Supporting Information
ABSTRACT: Two hydrophobic ionic liquids (ILs) 1-alkyl-3-methylimidazolium bis[(trifluoromethyl)sulfonyl]imide
([C2mim][NTf2] and [C4mim][NTf2]) were synthesized. The binary mixtures of the two ILs were prepared with dimethyl
carbonate (DMC) or diethyl carbonate (DEC) over the entire mole fraction range, respectively. The density and viscosity of the
binary mixtures were determined by an automated DMA 5000 M and a Lovis 2000 ME Anton Paar Rotational Stabinger
Viscometer at temperatures ranging from 288.15 to 328.15 K. The uncertainties of the density and viscosity are ur(ρ) = 0.00120
and ur(η) = 0.01. The excess molar volumes and viscosity deviations were calculated for the four binary mixtures by the mea-
surement values. The effects of the extension of the alkyl chain of the cation and anion on the above properties are discussed.
The effects of the methyl introduction on the cation was also discussed with the literature. The excess molar volumes and
viscosity deviations were fitted versus mole fraction according to the Redlich−Kister equation. The thermal expansion coef-
ficients of the systems were calculated according to the density values.
conductivity et al. have been studied by some groups.6,7,9,11,13
1. INTRODUCTION
The binary mixtures have also been studied with the traditional
Because of the outstanding physicochemical properties, such as
low melting temperature, good solvation, negligible vapor
solvents by some groups.4,5,8,10,12,15 The traditional solvents
are ethyl acetate and methanol,4 N-methyl-2-pyrrolidone and
pressure, high electrical conductivity, good thermal stability,
ethanol,16 triton,8 propylene carbonate,10 and 1-propanol and
and designability, etc.,1−3 ionic liquids (ILs) have been applied
1-butanol.15
in industrial and academic areas.
Because of the hydrophobicity, the hydrophobic ILs have
Dimethyl carbonate (DMC) and diethyl carbonate (DEC),
as a class of security substitutes for hazardous chemicals,
attracted much more concern from industry and the academic
have also attracted much more attention by scholars both at
community. As the hydrophobic group, the bis(trifluor-
omethylsulfonyl)imide([NTf2]−) anion has been used for
home and abroad. DMC and DEC have also been used in many
fields as environmentally benign chemicals, such as lithium
batteries, water emulsifiable formulations, synthesis of chem-
icals, and as solvents for extractive, natural, synthetic resin, or
synthesizing the ILs. This type of ILs has exhibited much more
unique properties, such as negligible vapor pressure at ambient
temperatures and excellent thermal stability. So, the systematic
polymers, etc. The binary mixtures of DMC or DEC with other
study of this type of ILs physicochemical properties has been
solvents have also been studied by some groups.17−27
probed by some groups, especially the imdazolium type ILs.4−15
However, viscosity is a limiting factor in the application of
ionic liquids,16 which reduces transport capabilities and retards
the chemical processes that occur in these solvents. It is essen-
tial for increasing the potential application of ILs in industry
and academia to study the physicochemical properties of the
binary mixtures in more detail. For [C2mim][NTf2] and
[C4mim][NTf2] ionic liquids, the density, viscosity, and
In 2011,28 we studied the electrical conductivity of pyri-
dinium type ILs with traditional solvents. The solvents are
methanol, ethanol, acetonitrile, and propylene carbonate. The
Received: July 9, 2018
Accepted: November 6, 2018
© XXXX American Chemical Society
A
DOI: 10.1021/acs.jced.8b00591
J. Chem. Eng. Data XXXX, XXX, XXX−XXX

Journal of Chemical & Engineering Data
Article
a
Table 1. Provenance, Mass Fraction Purity, CAS No., Water Content, and Br− Content of the Used Materials
chemical name
provenance
CASRN
purification method water content
Br− content
final mass fraction
b
[C2mim][Br]
[C4mim][Br]
DMC
DEC
Li[NTf2]
Lanzhou Institute of Chemical Physics
Lanzhou Institute of Chemical Physics
Aladdin
Aladdin
Solvay (ZhenJiang) Chemicals Co., LTD
synthesized
synthesized
65039-08-9
85100-77-2
616-38-6
none
none
none
none
none
water wash
water wash
≥0.99
≥0.99
>0.99
>0.99
b
b
b
105-58-8
b
90076-65-6
174899-82-2
174899-83-3
>0.999
c
d
e
[C2mim][NTf2]
[C4mim][NTf2]
276 × 10−6
<50 × 10−6
>0.99
>0.99
c
d
e
324 × 10−6
<50 × 10−6
a
Li[NTf2], lithium bis[(trifluoromethyl)sulfonyl]imide; [C2mmim][NTf2], 1-ethyl-3-dimethylimidazolium bis[(trifluoromethyl)sulfonyl]imide;
b
c
[C4mmim][NTf2], 1-butyl-3-dimethylimidazolium bis[(trifluoromethyl)sulfonyl]imide. As stated by the supplier. Determined by Karl Fischer
method. Determined by AgNO3/HNO3 solution. Determined by NMR spectra.
d
e
system exhibited a substantially higher conductivity after the
addition of the solvents in ILs.
to NMR spectra. The structures of [C2mim][NTf2], [C4mim]-
[NTf2], DMC, and DEC are shown in Figure 1.
Recently, we have also prepared the four binary mixtures of
1-alkyl-2,3-methylimidazolium bis[(trifluoromethyl)sulfonyl]-
imide ([C2mmim][NTf2] or [C4mmim][NTf2]) with DMC or
DEC.29 The density and viscosity were measured in the whole
composition. The excess molar volume and viscosity deviation
were calculated according to the density and viscosity.
On the basis of the above, the four binary mixtures of
[C2mim][NTf2] or [C4mim][NTf2] have been prepared with
DMC or DEC. The density and viscosity of the systems have
been determined in the whole composition. The excess molar
volume and viscosity deviation were calculated and fitted by
the Redlich−Kister equations to help better understand the
types of interactions involved in the solutions. The effect of the
extension of the alkyl chain and methyl group introduction of
the cation on these properties is also discussed with literature
values.29 The thermal expansion coefficients were also calcu-
lated according to the density values of the solution. This work
is a contribution to enlarge the existing database of these
properties needed to optimize the structural and interaction
parameters of group-contribution models.
Figure 1. Structures of [C2mim][NTf2], [C4mim][NTf2], DMC, and
DEC.
2.3. Water Content. The water content of [C2mim]-
[NTf2] and [C4mim][NTf2] was determined by a Karl Fischer
coulometric titrator (C20S, Mettler Toledo). The water con-
tent is 276 × 10−6 and 324 × 10−6 of the mass fraction [C2mim]-
[NTf2] and [C4mim][NTf2], respectively. These values are also
listed in Table 1.
2.4. Binary Mixtures Preparation. The binary mixtures
of [C2mim][NTf2] or [C4mim][NTf2] + DMC or DEC were pre-
pared by the weighing amounts of [C2mim][NTf2] or [C4mim]-
[NTf2] and DMC or DEC, covering the whole composition range
of the mixture, using a JJ224BC electronic digital balance
(uncertainty 1 × 10−4 g), and the uncertainty of the mole
fraction is better than 0.0002. A 3 mL sample was used to
measure the properties.
2.5. Density and Viscosity. The density and viscosity
values of the binary mixtures (including the pure [C2mim]-
[NTf2], [C4mim][NTf2], DMC, and DEC) were measured
from 288.15 to 328.15 K by an automated DMA 5000 M and a
Lovis 2000 ME Anton Paar Rotational Stabinger Viscometer
with cylinder geometry. The principle is based on a modified
Couette according to a rapidly rotating outer tube and a relative
slowly rotating inner measuring bob. The viscometer−densimeter
was calibrated before the properties measurements with degassed
water (heating and cooling) and standard oil. The values were
recorded every 5 K, the temperature was controlled to be
0.02 K, and each value is the average of the three times and
the uncertainty is better than 0.00120 for density at 0.68
2. EXPERIMENTAL SECTION
2.1. Materials. The materials of 1-ethyl-3-methylimidazo-
lium bromide ([C2mim][Br]), 1-butyl-3-methylimidazolium
bromide ([C4mim][Br]), and lithium bis[(trifluoromethyl)-
sulfonyl]imide (Li[NTf2]) were used for the ionic liquids syn-
thesis. The provenance and mass fraction purity of the used
materials are listed in Table 1.
2.2. Preparation of ILs [C2mim][NTf2] and [C4mim]-
[NTf2]. [C2mim][NTf2] and [C4mim][NTf2] were synthesized
in the distilled water and dichloromethane by the tradi-
tional ion exchange reaction.30,31 The 30 g of [C2mim][Br] (or
[C4mim][Br]) was dissolved with distilled water and placed in
a 250 mL flask. The 50 mL of dichloromethane was also added
into the 250 mL flask. The equivalent amount of LiNTf2 salt
was also added into the flask at room temperature and stirred
for 1 h. The bottom solution was washed several times with
distilled water for more than 10 times. The Br− were detected
by AgNO3/HNO3 solution (the content was estimated to lower
than 50 × 10−6 mass fraction). The compounds are colorless
liquid, and the final product was finally dried in high vacuum
(<1mbar) for 48 h at 353 K before the binary mixtures
preparation. The final products of the ILs [C2mim][NTf2] and
1
[C4mim][NTf2] were characterized by H NMR spectroscopy
(see the Figures S1 and S2 of the Supporting Information) and
the purities were estimated better than 99% by mass according
B
DOI: 10.1021/acs.jced.8b00591
J. Chem. Eng. Data XXXX, XXX, XXX−XXX

Journal of Chemical & Engineering Data
Article
C
DOI: 10.1021/acs.jced.8b00591
J. Chem. Eng. Data XXXX, XXX, XXX−XXX

Journal of Chemical & Engineering Data
Article
Table 3. Experimental Values of Density, ρ/g·cm−3, of ILs + Solvents at Different Mole Fractions from 288.15 K to 328.15 K at
a
Atmospheric Pressure (p = 101.3 kPa)
xIL
T/K = 288.15 T/K = 293.15 T/K = 298.15 T/K = 303.15 T/K = 308.15 T/K = 313.15 T/K = 318.15 T/K = 323.15 T/K = 328.15
[C2mim][NTf2] + DMC
0.0000
0.0989
0.1983
0.2973
0.3958
0.4960
0.5954
0.6967
0.7982
0.9004
1.0000
1.07639
1.19915
1.28285
1.34257
1.38769
1.42397
1.45255
1.47687
1.49752
1.51450
1.52855
1.06986
1.19310
1.27711
1.33702
1.38228
1.41862
1.44728
1.47162
1.49237
1.50939
1.52347
1.06327
1.18703
1.27135
1.33147
1.37685
1.41328
1.44202
1.46642
1.48723
1.50428
1.51839
1.05665
1.18095
1.26559
1.32591
1.37144
1.40796
1.43678
1.46124
1.48209
1.49919
1.51334
1.05000
1.17486
1.25983
1.32035
1.36603
1.40266
1.43155
1.45607
1.47698
1.49412
1.50830
1.04329
1.16875
1.25407
1.31481
1.36063
1.39736
1.42634
1.45093
1.47188
1.48906
1.50328
1.03657
1.16263
1.24830
1.30926
1.35523
1.39208
1.42114
1.44579
1.46680
1.48402
1.49827
1.02983
1.15650
1.24254
1.30372
1.34985
1.38681
1.41592
1.44067
1.46174
1.47900
1.49328
1.02303
1.15034
1.23676
1.29819
1.34447
1.38155
1.41075
1.43557
1.45669
1.47400
1.48831
[C2mim][NTf2] + DEC
0.0000
0.0991
0.1982
0.3024
0.3979
0.4982
0.5963
0.6992
0.7987
0.9000
1.0000
0.98049
1.09045
1.17930
1.25464
1.31221
1.36222
1.40491
1.44262
1.47505
1.50375
1.52855
0.97491
1.08501
1.17395
1.24939
1.30699
1.35704
1.39978
1.43750
1.46995
1.49866
1.52347
0.96930
1.07954
1.16860
1.24411
1.30178
1.35187
1.39464
1.43238
1.46486
1.49358
1.51839
0.96366
0.95800
1.06856
1.15786
1.23356
1.29136
1.34155
1.38440
1.42219
1.45471
1.48346
1.50830
0.95232
1.06305
1.15248
1.22828
1.28615
1.33641
1.37930
1.41712
1.44966
1.47842
1.50328
0.94660
1.05753
1.14711
1.22301
1.28095
1.33127
1.37420
1.41206
1.44462
1.47341
1.49827
0.94086
1.05198
1.14172
1.21774
1.27576
1.32613
1.36911
1.40701
1.43960
1.46841
1.49328
0.93508
1.04642
1.13632
1.21246
1.27058
1.32101
1.36403
1.40198
1.43459
1.46342
1.48831
1.07407
1.16323
1.23883
1.29656
1.34670
1.38951
1.42728
1.45977
1.48851
1.51334
[C4mim][NTf2] + DMC
0.0000
0.0898
0.1882
0.2749
0.3754
0.4720
0.5745
0.6730
0.7799
0.8948
1.0000
1.07639
1.17803
1.25071
1.29536
1.33426
1.36215
1.38580
1.40416
1.41988
1.43465
1.44566
1.06986
1.17207
1.24510
1.28995
1.32902
1.35702
1.38077
1.39914
1.41497
1.42979
1.44084
1.06327
1.16607
1.23948
1.28455
1.32378
1.35190
1.37574
1.39418
1.41007
1.42493
1.43601
1.05665
1.05000
1.15402
1.22822
1.27373
1.31332
1.34167
1.36570
1.38429
1.40031
1.41526
1.42643
1.04329
1.14798
1.22258
1.26832
1.30809
1.33658
1.36070
1.37937
1.39544
1.41045
1.42166
1.03657
1.14193
1.21694
1.26292
1.30288
1.33149
1.35571
1.37445
1.39059
1.40567
1.41691
1.02983
1.13585
1.21130
1.25751
1.29767
1.32640
1.35073
1.36955
1.38574
1.40088
1.41217
1.02303
1.12976
1.20565
1.25210
1.29246
1.32133
1.34575
1.36466
1.38090
1.39612
1.40745
1.16005
1.23385
1.27914
1.31855
1.34678
1.37071
1.38923
1.40518
1.42008
1.43121
[C4mim][NTf2] + DEC
0.0000
0.1025
0.2198
0.3178
0.4211
0.5268
0.6220
0.7193
0.8139
0.9088
1.0000
0.98049
1.08684
1.17790
1.23657
1.28586
1.32709
1.35833
1.38568
1.40825
1.42849
1.44566
0.97491
1.08145
1.17270
1.23147
1.28083
1.32213
1.35342
1.38079
1.40338
1.42365
1.44084
0.96930
1.07605
1.16748
1.22635
1.27580
1.31716
1.34849
1.37590
1.39852
1.41881
1.43601
0.96366
0.95800
1.06523
1.15703
1.21612
1.26574
1.30725
1.33867
1.36617
1.38884
1.40918
1.42643
0.95232
1.05980
1.15180
1.21099
1.26071
1.30230
1.33378
1.36132
1.38401
1.40439
1.42166
0.94660
1.05435
1.14657
1.20588
1.25569
1.29736
1.32890
1.35648
1.37919
1.39960
1.41691
0.94086
1.04888
1.14133
1.20077
1.25068
1.29244
1.32402
1.35166
1.37439
1.39485
1.41217
0.93508
1.04340
1.13607
1.19565
1.24568
1.28750
1.31916
1.34684
1.36958
1.39010
1.40745
1.07065
1.16226
1.22123
1.27077
1.31220
1.34358
1.37104
1.39368
1.41397
1.43121
a
Standard uncertainties are ur(ρ) = 0.00120, u(T) = 0.05 K, u(p) = 5 kPa, u(x) = 0.0002.
confidence level, the uncertainty is better than 0.01 for viscosity
at 0.95 confidence level. For density, the uncertainty is obtained
from literature.32 For viscosity, the uncertainty is mainly from
the machine (the values are 1.59 mm and 1.8 mm capillary are
0.007 and 0.005, respectively, for a steel ball). The water con-
tent should also be considered for the uncertainty determi-
nation. However, the contents are less than 400 × 10−6 mass
fraction before measurement. According to Jacquemin33 et al.
and our previous work,34 the water content change can be
ignored before and after measurement of density and viscosity
by the Lovis 2000 ME Anton Paar Rotational Stabinger vis-
cometer. So, the values can be ignored during measurements.
The density and viscosity of the pure compounds [C2mim]-
[NTf2], [C4mim][NTf2], DMC, and DEC from this study and
available from the literature are shown in Table 2.4−15,17−27
The measured values of the binary mixtures are listed in Tables 3
and 4. All of the values of the density and viscosity were mea-
sured at atmospheric pressure (p = 101.3 kPa).
D
DOI: 10.1021/acs.jced.8b00591
J. Chem. Eng. Data XXXX, XXX, XXX−XXX

Journal of Chemical & Engineering Data
Article
Table 4. Experimental Values of Dynamic Viscosity, η/mPa·s, of ILs + Solvents at Different Mole Fractions from 288.15 K to
a
328.15 K at Atmospheric Pressure (p = 101.3 kPa)
xIL\T/K T/K = 288.15 T/K = 293.15 T/K = 298.15 T/K = 303.15 T/K = 308.15 T/K = 313.15 T/K = 318.15 T/K = 323.15 T/K = 328.15
[C2mim][NTf2] + DMC
0.0000
0.0989
0.1983
0.2973
0.3958
0.4960
0.5954
0.6967
0.7982
0.9004
1.0000
0.669
1.579
2.913
4.862
7.561
11.21
16.89
22.56
30.07
38.55
49.41
0.626
1.451
2.637
4.332
6.635
9.698
14.58
19.02
25.12
31.87
40.36
0.587
1.348
2.400
3.884
5.878
8.484
12.53
16.66
21.25
26.71
33.52
0.552
1.250
2.195
3.507
5.241
7.472
10.80
14.52
18.37
22.66
28.35
0.520
1.162
2.019
3.177
4.706
6.640
9.382
12.62
16.22
19.42
24.15
0.498
1.086
1.865
2.904
4.247
5.946
8.189
10.96
14.22
17.21
20.76
0.472
1.016
1.729
2.661
3.831
5.358
7.249
9.578
12.43
15.16
17.90
0.450
0.954
1.608
2.452
3.512
4.857
6.332
8.381
10.90
13.29
15.93
0.429
0.898
1.501
2.268
3.224
4.421
5.588
7.456
9.610
11.68
14.26
[C2mim][NTf2] + DEC
0.0000
0.0991
0.1982
0.3024
0.3979
0.4982
0.5963
0.6992
0.7987
0.9000
1.0000
0.871
1.938
3.368
5.628
8.533
12.38
17.23
24.14
31.13
39.07
49.41
0.812
1.769
3.032
4.987
7.450
10.66
14.65
20.32
25.96
32.29
40.36
0.757
1.623
2.746
4.452
6.552
9.269
12.59
17.65
21.91
27.04
33.52
0.708
0.664
1.389
2.288
3.607
5.196
7.192
9.572
13.37
16.59
19.65
24.15
0.625
1.290
2.102
3.278
4.672
6.410
8.445
11.60
14.56
17.36
20.76
0.589
1.204
1.939
2.993
4.223
5.749
7.525
10.14
12.72
15.35
17.90
0.556
1.121
1.794
2.746
3.839
5.184
6.739
8.895
11.15
13.53
15.93
0.525
1.049
1.667
2.528
3.509
4.704
6.075
7.875
9.813
11.93
14.26
1.495
2.498
3.992
5.819
8.127
10.93
15.41
18.79
22.93
28.35
[C4mim][NTf2] + DMC
0.0000
0.0898
0.1882
0.2749
0.3754
0.4720
0.5745
0.6730
0.7799
0.8948
1.0000
0.669
1.605
3.207
5.396
9.186
14.30
22.53
32.06
44.52
61.53
78.02
0.626
1.473
2.886
4.762
7.930
12.12
18.87
26.30
35.81
48.74
61.32
0.587
1.365
2.611
4.235
6.922
10.39
16.30
21.86
29.38
39.46
48.93
0.552
1.263
2.376
3.797
6.100
8.998
14.00
18.59
24.46
32.86
39.84
0.520
1.173
2.176
3.428
5.404
7.885
11.98
16.17
20.58
27.73
32.91
0.498
1.095
2.002
3.113
4.822
6.959
10.30
14.01
17.54
23.58
27.56
0.472
1.022
1.849
2.837
4.332
6.189
8.913
12.10
15.20
19.93
23.33
0.450
0.958
1.719
2.600
3.943
5.540
7.757
10.53
13.21
17.01
19.97
0.429
0.899
1.588
2.394
3.590
4.994
6.772
9.191
11.54
14.93
17.41
[C4mim][NTf2] + DEC
0.0000
0.1025
0.2198
0.3178
0.4211
0.5268
0.6220
0.7193
0.8139
0.9088
1.0000
0.871
2.120
4.415
7.583
13.26
20.12
28.36
38.93
50.88
64.94
78.02
0.812
1.928
3.925
6.526
11.18
17.25
23.42
31.68
40.79
51.44
61.32
0.757
1.764
3.517
5.739
9.492
14.77
19.58
26.16
33.25
41.43
48.93
0.708
0.664
1.492
2.873
4.539
7.219
10.76
14.69
18.70
23.20
28.32
32.91
0.625
1.385
2.614
3.977
6.414
9.287
12.63
16.35
19.64
23.69
27.56
0.589
1.286
2.391
3.591
5.815
8.069
10.92
14.18
16.89
20.05
23.33
0.556
1.198
2.194
3.259
5.216
7.105
9.492
12.28
14.60
17.26
19.97
0.525
1.117
2.025
2.978
4.710
6.138
8.288
10.66
12.69
15.00
17.41
1.618
3.168
5.085
8.179
12.60
17.03
21.88
27.57
34.06
39.84
a
Standard uncertainties are u(T) = 0.05 K, u(p) = 5 kPa, u(x) = 0.0002, ur(η) = 0.01.
the absolute density deviations are higher than 0.04% and less
than 0.18% in the literature;10−15 the absolute viscosity
deviations are higher than 1.2% and less than 4.1% in the
literature.10,13 For DMC, the absolute density deviations are
less than 0.10% in the literature17−24 except one point,
0.139%;22 the absolute viscosity deviations are less than 10% in
the literature17,20−24 except for one point, 15.556%.22 For
DEC, the absolute density deviations are less than 0.03% in the
literature23,25−27 except for two points, 0.132% and 0.115%;26
3. RESULTS AND DISCUSSION
The density and viscosity of the ILs [C2mim][NTf2],
[C4mim][NTf2], DMC, and DEC are listed in Table 2. The
deviations of the experiment and literature values are calcu-
lated and listed in Table 2. From Table 2, for [C2mim][NTf2],
the absolute density deviations are less than 0.03% in the
literature4−7 except for those in ref 8 (but the absolute devia-
tions are still less than 0.14%); the absolute viscosity deviations
are less than 6.6% in the literature.4,5,9 For [C4mim][NTf2],
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rates have been listed in Table S1 in the Supporting
Information.
3.1. Excess Molar Volume. According to the following
equation, the excess molar volumes, VE can be determined:
x1M1 + x2M2
x1M1
x2M2
ρ2
VE =
−
−
ρ
ρ
(1)
1
herein, VE is the excess molar volume; ρ is the density of the
binary mixture; x1, M1, ρ1, x2, M2, and ρ2 are the mole fraction,
molar mass, and density of components 1 and 2, respectively.
The calculated values of the four binary mixtures are listed in
Table 5.
The VE, against xi plots of the four binary mixtures are
shown in Figure 3 from 288.15 to 328.15 K. From Figure 3,
it can be seen that the values are negative over the whole com-
position range and all of the curves are asymmetrical. According
to the references26,35 and our previous research results,29
we conclude that there are three main factors that may affect
the VE values, namely the specific factors between molecules
(such as hydrogen bonds, charge-transfer complexes, breaking
of hydrogen bonds), the physical intermolecular forces (gener-
ally including electrostatic forces between charged particles
and between permanent dipoles, induction forces between a
permanent dipole and an induced dipole, and forces of attrac-
tion and repulsion between nonpolar molecules) and the struc-
tural characteristics of the component. In the studied mixtures,
hydrogen bonding and ion-dipole forces are expected to be the
dominant attraction, however, they usually weaken with the
increase of temperature, which will lead to the opposite trend
of VE. Besides, the negative excess volumes observed may be
related to a relatively more packed arrangement of the mole-
cules and ions in the mixture at high temperature.
In Figure 3, the absolute values, |VE|, increase with the temper-
ature increasing. This points to the existence of stronger inter-
actions of ILs with solvents than before the temperature increase.
The same result has been found in the literature.35 To compare
the values with [C2mmim][NTf2] and [C4mmim][NTf2],29
the VE, against xi plots of the eight binary mixtures are shown
in Figure 4 at 298.15 K. From Figure 4, the order of the
absolute values, |VE|, is [C4mmim][NTf2] + DMC < [C2mmim]-
[NTf2] + DMC < [C4mim][NTf2] + DMC < [C2mim][NTf2] +
DMC < [C4mmim][NTf2] + DEC < [C2mmim][NTf2] + DEC
≈ [C4mim][NTf2] + DEC < [C2mim][NTf2] + DEC in the
whole mole fraction. For DEC and DMC, the absolute values
of the mixtures containing DEC are higher than those of the
mixtures containing DMC. This may occur because with the
increases of the chain carbonate, the polarity lessens, and the
intermolecular attraction decreases; dilution process is less
endothermic, and |VE| values that are higher are those of the
mixtures containing DEC. The same result has also been found
in ref 24. After the introduction of the methylene group on the
side chain of ILs cation 1-position, the absolute values of VE
are lower than those without the methylene group for the same
solvent. This may be because the introduction of the
methylene group leads to the increase of steric effect, which
weakens the binding ability of ILs with solvents (DEC or
DMC) and makes the interaction worse. The same result has
been found after the introduction of the methyl group on the
ILs cation 2-position for the same solvent. The absolute values
are lower than those without methyl introduction. The steric
effect can also be used to explain why the absolute values
decrease after the introduction of the methyl group on the ILs
Figure 2. Plot of density, ρ/g·cm−3, and viscosity, η/mPa·s, vs molar
■
fraction, xIL, of binary mixtures at 298.15 K at p = 101.3 kPa:
,
●
▲
[C2mim][NTf2] + DMC; , [C2mim][NTf2] + DEC; , [C4mim]-
⧫
□
[NTf2] + DMC; , [C4mim][NTf2] + DEC; , [C2mmim][NTf2] +
DMC; , [C2mmim][NTf2] + DEC; , [C4mmim][NTf2] + DMC;
○
△
◇
, [C4mmim][NTf2] + DEC.
the absolute viscosity deviations are less than 2.4% in the
literature.23,25−27
In Figure 2, the density and viscosity of the four binary
mixtures were plotted over the entire mole fraction at 298.15 K
and compared with our previous work (research on [C2mmim]-
[NTf2] + DMC, [C2mmim][NTf2] + DEC, [C4mmim][NTf2] +
DMC, and [C4mmim][NTf2] + DEC systems).29 From Figure 2,
for the density, for the same ILs, the values of DMC systems
are higher than those of the DEC systems; for the same
solvents, the values change to smaller after the introduction of
a methyl group on the 2-position or methylene group on the
side chain of the ILs cation. For the viscosity, the tendency is
in contrast. For the same ILs, the values of the DMC systems
are lower than those of the DEC systems; for the same
solvents, the values change to larger after the introduction of a
methyl group on the 2-position or methylene group on the side
chain of the ILs cation.
From Tables 3 and 4, the density and viscosity decrease with
the temperature increase and concentration decrease of the
ILs. According to the viscosity, the binary mixtures are viscous
liquids and non-Newtonian fluids. On this basis, all of the shear
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Figure 3. Plot of excess molar volumes, VE/cm3·mol−1, vs molar fraction, xIL, of binary mixtures from 288.15 K to 328.15 K at p = 101.3 kPa.
■
(a) [C2mim][NTf2] + DMC; (b) [C2mim][NTf2] + DEC; (c) [C4mim][NTf2] + DMC; (d) [C4mim][NTf2] + DEC: , 288.15 K;
⧫
●
▲
▼
, 293.15 K; , 298.15 K; , 303.15 K; ◀, 308.15 K; ▶, 313.15 K; , 318.15 K; ⬟, 323.15 K; ⬢, 328.15 K.
cation. The minimum excess molar volumes can be shown at
the mole fractions x ≈ 0.30 for DMC type binary mixtures,
x ≈ 0.38 for DEC type binary mixtures, respectively. From
Figure 4, for DMC type binary mixtures, the mole fractions are
slightly higher than the mole fractions x ≈ 0.25 of the
[C2mmim][NTf2] or [C4mmim][NTf2] system;29 for DEC
type binary mixtures, the mole fractions are slightly higher than
the mole fraction, x ≈ 0.35 of the [C2mmim][NTf2] or
[C4mmim][NTf2] system.29 This should be because the
introduction of the methyl group leads to the increase of
steric effect, which weakens the binding ability of ionic liquids
with solvents (DEC or DMC) and makes the interaction
worse. Therefore, it can reach a stable state at a lower
concentration, and the |VE| reaches the maximum easily.
3.2. Viscosity Deviation. According to the following
equation, the viscosity deviation, Δη can also be determined:
In Figure 5, as with the excess molar volumes, the values
are negative over the whole composition range and all of the
curves are asymmetric. In Figure 5 the absolute values decrease
with increasing temperature. To compare the values with those
of our previous work,29 the data Δη of [C2mmim][NTf2] and
[C4mmim][NTf2] against xi plots of the eight binary mixtures
are also shown in Figure 6 with this work at 298.15 K. Unlike
those of the excess molar volumes, the minimum viscosity
deviations can be seen at the mole fraction x ≈ 0.50 for the
four binary mixtures, which are slightly less than those of the
four binary mixtures of [C2mmim][NTf2] or [C4mmim]-
[NTf2].29 From Figure 6, the order of the absolute values, |Δη|,
is [C2mim][NTf2] + DEC < [C2mim][NTf2] + DMC <
[C4mim][NTf2] + DEC < [C4mim][NTf2] + DMC <
[C2mmim][NTf2] + DEC < [C2mmim][NTf2] + DMC <
[C4mmim][NTf2] + DEC < [C4mmim][NTf2] + DMC in the
whole mole fraction. From Figure 6, the absolute values are
increased with the methyl group and methylene group
introduction on the cation of the ILs. The absolute values
increase from DEC to DMC for the same ionic liquid. The
results are opposite with excess molar volumes. Similar to the
excess molar volumes, the viscosity is also related to the
molecular interaction between the components of mixtures as
well as of the size and shape of molecules. According to the
literature,36 intermolecular interactions strongly influence the
Δη = η − (x1η1 + x2η2)
(2)
where Δη is the viscosity deviation; x1, η1, x2, and η2 are the
mole fraction and viscosity of components 1 and 2,
respectively. The calculated values of the viscosity deviation
are also listed in Table 5.
Like those of the excess molar volumes, the viscosity
deviations, Δη, versus mole fraction, xi, of the four binary
mixtures are shown in Figure 5 from 288.15 to 328.15 K.
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Figure 6. Plot of viscosity deviation, Δη/mPa·s, vs molar fraction,
xIL, of four binary mixtures at 298.15 K at p = 101.3 kPa.
Figure 4. Plot of excess molar volumes, VE/cm3·mol−1, vs molar
fraction, xIL, of binary mixtures at 298.15 K at p = 101.3 kPa.
■
●
▲
,
, [C2mim][NTf2] + DMC; , [C2mim][NTf2] + DEC;
■
●
▲
, [C2mim][NTf2] + DMC; , [C2mim][NTf2] + DEC;
,
,
,
⧫
□
[C4mim][NTf2] + DMC; , [C4mim][NTf2] + DEC; , [C2mmim]-
[NTf2] + DMC; , [C2mmim][NTf2] + DEC; , [C4mmim][NTf2]
◆
□
△
[C4mim][NTf2] + DMC;
[C2mmim][NTf2] + DMC; , [C2mmim][NTf2] + DEC;
, [C4mim][NTf2] + DEC;
○
△
○
◇
+ DMC; , [C4mmim][NTf2] + DEC.
◇
[C4mmim][NTf2] + DMC; , [C4mmim][NTf2] + DEC.
Δη such as anion−cation interactions in the pure IL. The IL
has high viscosity because the movement of molecules from
one equilibrium position to the next is strongly disturbed by
neighboring molecules. The anion−cation interactions in the
Figure 5. Plot of viscosity deviation, Δη/mPa·s, vs molar fraction, xIL, of four binary mixtures from 288.15 K to 328.15 K at p = 101.3 kPa.
■
●
▲
,
(a) [C2mim][NTf2] + DMC; (b) [C2mim][NTf2] + DEC; (c) [C4mim][NTf2] + DMC; (d) [C4mim][NTf2] + DEC: , 288.15 K; , 293.15 K;
298.15 K; , 303.15 K; ◀, 308.15 K; ▶, 313.15 K; , 318.15 K; ⬟, 323.15 K; ⬢, 328.15.
◆
▼
I
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Table 7. Thermal Expansion Coefficients, 104α/K−1, of ILs + Solvents at Different Mole Fractions According to Equation 5 in
a
the Temperature Range 288.15 K to 328.15 K
xIL
T/K = 288.15 T/K = 293.15 T/K = 298.15 T/K = 303.15 T/K = 308.15 T/K = 313.15 T/K = 318.15 T/K = 323.15 T/K = 328.15
[C2mim][NTf2] + DMC
0.0000
0.0989
0.1983
0.2973
0.3958
0.4960
0.5954
0.6967
0.7982
0.9004
1.0000
12.4
10.2
8.96
12.4
10.2
9.00
12.5
10.3
9.05
12.6
10.3
9.09
12.7
10.4
9.13
12.8
10.4
9.17
12.8
10.5
9.21
12.9
10.6
9.26
13.0
10.6
9.30
8.27
7.78
7.44
7.16
6.97
6.81
6.67
6.61
8.30
7.81
7.47
7.19
7.00
6.83
6.69
6.63
8.34
7.84
7.50
7.21
7.02
6.86
6.71
6.65
8.37
7.87
7.53
7.24
7.05
6.88
6.74
6.67
8.41
7.91
7.56
7.26
7.07
6.91
6.76
6.70
8.44
7.94
7.59
7.29
7.10
6.93
6.78
6.72
8.48
7.97
7.61
7.32
7.12
6.95
6.81
6.74
8.51
8.00
7.64
7.35
7.15
6.98
6.83
6.76
8.55
8.03
7.67
7.37
7.17
7.00
6.85
6.79
[C2mim][NTf2] + DEC
11.8 11.9
9.64
0.0000
0.0991
0.1982
0.3024
0.3979
0.4982
0.5963
0.6992
0.7987
0.9000
1.0000
11.6
10.1
9.33
11.7
11.8
12.0
12.0
12.1
12.2
9.86
9.11
8.56
8.19
7.88
7.64
7.44
7.28
7.14
6.63
9.73
8.99
8.44
8.07
7.77
7.53
7.33
7.17
7.03
6.65
9.68
8.94
8.40
8.02
7.72
7.48
7.29
7.12
6.99
6.67
9.60
8.85
8.30
7.93
7.63
7.40
7.20
7.04
6.90
6.72
9.65
8.89
8.34
7.96
7.66
7.42
7.22
7.06
6.92
6.74
9.60
8.85
8.29
7.92
7.62
7.38
7.18
7.02
6.88
6.76
9.65
8.89
8.33
7.95
7.65
7.40
7.20
7.04
6.90
6.79
8.90
8.35
7.98
7.68
7.44
7.24
7.08
6.94
6.70
8.77
8.38
8.08
7.83
7.63
7.46
7.32
6.61
[C4mim][NTf2] + DMC
0.0000
0.0898
0.1882
0.2749
0.3754
0.4720
0.5745
0.6730
0.7799
0.8948
1.0000
12.4
10.3
9.03
12.4
10.3
9.08
12.5
10.4
9.12
12.6
10.4
9.16
12.7
10.5
9.20
12.8
10.5
9.24
12.8
10.6
9.29
12.9
10.7
9.33
13.0
10.7
9.37
8.34
7.87
7.49
7.22
7.03
6.86
6.71
6.61
8.37
7.90
7.52
7.24
7.05
6.89
6.74
6.63
8.41
7.93
7.54
7.27
7.08
6.91
6.76
6.65
8.44
7.96
7.57
7.30
7.10
6.93
6.78
6.68
8.48
8.00
7.60
7.32
7.13
6.96
6.81
6.70
8.52
8.03
7.63
7.35
7.16
6.98
6.83
6.72
8.55
8.06
7.66
7.38
7.18
7.01
6.85
6.74
8.59
8.09
7.69
7.40
7.21
7.03
6.88
6.77
8.63
8.12
7.72
7.43
7.23
7.06
6.90
6.79
[C4mim][NTf2] + DEC
0.0000
0.1025
0.2198
0.3178
0.4211
0.5268
0.6220
0.7193
0.8139
0.9088
1.0000
11.6
10.0
8.91
11.7
10.1
8.95
11.8
10.1
8.99
11.8
10.2
9.03
11.9
10.2
9.07
12.0
10.3
9.12
12.0
10.3
9.16
12.1
10.4
9.20
12.2
10.5
9.24
8.41
7.78
7.46
7.21
7.01
6.86
6.72
6.61
8.45
7.81
7.49
7.24
7.03
6.89
6.74
6.63
8.48
7.84
7.52
7.26
7.06
6.91
6.76
6.65
8.52
7.87
7.54
7.29
7.08
6.94
6.79
6.68
8.55
7.90
7.57
7.32
7.11
6.96
6.81
6.70
8.59
7.93
7.60
7.34
7.13
6.98
6.83
6.72
8.62
7.96
7.63
7.37
7.16
7.01
6.86
6.74
8.66
8.00
7.66
7.40
7.18
7.03
6.88
6.77
8.70
8.03
7.69
7.43
7.21
7.06
6.90
6.79
a
Standard uncertainties are ur(α) = 0.0012, u(T) = 0.05 K, u(p) = 5 kPa, u(x) = 0.0002.
IL are obviously weakened, and the viscosity value decreases
rapidly when organic solvents are added to the IL.
3.3. Redlich−KisterPolymomial Equation. Usually, the
Redlich−Kister equation was used for the fitting of the excess
molar volumes or viscosity deviations. The equation is below:
parameters and determined using the least-squares meth-
ods.37−39 For most ILs system,24,36−39 the Ai values were taken
from 0 to 3; four parameters are suitable and convenient. The
adjustable parameters are listed in Table 6.
In each case, the standard relative deviation between experi-
mental and calculated data wase used to determine the optimum
number of the adjustable parameters. It was calculated according
to the following equation:
3
Y = x(1 − x) A (2x − 1)i
∑
i
(3)
i=0
Ä
Å
É
where Y is the excess molar volume, VE, or viscosity deviation,
Δη; x is the mole fraction of ILs; Ai are the adjustable
1/2
Ñ
2
Å
Å
Å
Ñ
Ñ
Ñ
σ(Y) =
(Y − Y ) /(n − m)
∑
exp
cal
(4)
Å
Ç
Ñ
Ö
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Funding
where Y is the experimental and calculated values of the excess
molar volume or viscosity deviation; n is the number of the
experimental points over the whole concentration; and m is the
number of the coefficients of the Redlich−Kister equation. The
standard relative deviations are also listed in Table 6. From
Table 6, it can be seen that all of the standard relative devia-
tions are less than 0.033 cm3·mol−1 for density and 0.32 mPa·s
for viscosity, respectively. According to the literature,40 the stan-
dard relative deviations are in the permissible range. So, the four
parameters are suitable and convenient for the excess molar
volumes and viscosity deviations fitting by the Redlich−Kister
equation.
This work was supported by the Program for Liaoning
Excellent Talents in University (LJQ2015099), China Scholar-
ship Council (201608210093).
Notes
The authors declare no competing financial interest.
REFERENCES
■
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literature, the thermal expansion coefficient of the mixtures can
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∂ρ
y
z
z
z
1 i
j
αP/(K−1) = −
j
j
ρ ∂T
(5)
k
{
where α is the thermal expansion coefficient. The values are
listed in Table 7. As seen in Table 7, the values of the thermal
expansion coefficient decrease with the increase of the concen-
tration of the ILs and increase with increasing temperature. All
of the values are in the range of 6 × 10−4 to 13 × 10−4 K−1.
4. CONCLUSIONS
In this work, the densities and viscosities of four binary
mixtures were measured by traditional methods from 288.15 K
to 328.15 K. The uncertainties of the density and viscosity are
ur(ρ) = 0.00120 and ur(η) = 0.01. The excess molar volumes
and viscosity deviations were calculated from the experimental
values. The density decreases with the cation alkyl chain length
increase for the same ILs or solvents at the same mole fraction.
However, the viscosity tendency is in contrast with the density.
Meanwhile, the interionic interaction, especially hydrogen
bonding, has a significant influence on the viscosity of ILs. The
excess molar volumes and viscosity deviations are negative in
the whole concentration. The orders of the absolute values are
[C4mmim][NTf2] + DMC < [C2mmim][NTf2] + DMC <
[C4mim][NTf2] + DMC < [C2mim][NTf2] + DMC <
[C4mmim][NTf2] + DEC < [C2mmim][NTf2] + DEC ≈
[C4mim][NTf2] + DEC < [C2mim][NTf2] + DEC for excess
molar volumes and [C2mim][NTf2] + DEC < [C2mim][NTf2]
+ DMC < [C4mim][NTf2] + DEC < [C4mim][NTf2] + DMC
< [C2mmim][NTf2] + DEC < [C2mmim][NTf2] + DMC <
[C4mmim][NTf2] + DEC < [C4mmim][NTf2] + DMC for
viscosity deviations in the whole mole fraction.
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ASSOCIATED CONTENT
* Supporting Information
The Supporting Information is available free of charge on the
ACS Publications website at DOI: 10.1021/acs.jced.8b00591.
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activity coefficients at infinite dilution in ionic liquids using the dilutor
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pressure dependence of the viscosity of the ionic liquids 1-hexyl-3-
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Thomas S.S. Raju, K.; Bala Murali Krishna, K.; Hari Babu, B.
Investigation of solute-solvent interactions in {1-butyl-3-
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■
S
1H NMR spectrus of [C2mim][NTf2], [C4mim][NTf2],
and shear rates of ILs + solvents at different mole
fractions from 288.15 K to 328.15 K at atmospheric
pressure (PDF)
AUTHOR INFORMATION
Corresponding Author
*E-mail: liuqingshan@dicp.ac.cn.
■
ORCID
: 0000-0002-0949-8066
L
DOI: 10.1021/acs.jced.8b00591
J. Chem. Eng. Data XXXX, XXX, XXX−XXX

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DOI: 10.1021/acs.jced.8b00591
J. Chem. Eng. Data XXXX, XXX, XXX−XXX