1318
Ind. Eng. Chem. Res. 2008, 47, 1318-1330
Critical Properties, Normal Boiling Temperature, and Acentric Factor of Another 200 Ionic Liquids Jose´ O. Valderrama,*,†,‡ Wilson W. Sanga,†,§ and Juan A. Lazzu´ s†,⊥ Center for Technological Information (CIT), Casilla 724, La Serena, Chile, Department of Mechanical Engineering, Faculty of Engineering, UniVersity of La Serena, Casilla 554, La Serena, Chile, Faculty of Chemical Engineering, UniVersidad Nacional del Altiplano, AV. Floral 1153, Puno, Peru´ , and Department of Physics, Faculty of Sciences, UniVersity of La Serena, Casilla 554, La Serena, Chile
The critical properties, the normal boiling temperature, and the acentric factor of 200 ionic liquids have been determined using an extended group contribution method, which is based on the well-known concepts of Lydersen and Joback and Reid, that was developed by the authors. The method does not require any additional data besides knowledge of the structure of the molecule and its molecular mass. Because experimental critical properties of ionic liquids are not available, the accuracy of the method is checked by calculating the liquid density of the ionic liquids considered in the study for which experimental data are available in the literature. The results show that the values determined for the critical properties, the normal boiling temperature, and the acentric factor are sufficiently accurate for engineering calculations, generalized correlations, and equation of state methods, among other applications. Introduction The authors have recently presented a procedure to estimate the critical properties (temperature (TC), pressure (PC), and volume (VC)), the normal boiling temperature (Tb), and the acentric factor (ω) of ionic liquids using a group contribution method that unifies the best characteristics of two of the most used simplest techniques: Lydersen1 and Joback and Reid.2 The accuracy of the estimated values were tested by determining the density of the ionic liquids using an independent equation that was not applied in determining the critical properties. The tests proved that the predicted values seem to be reasonable, considering the relatively low deviations between experimental and calculated densities.3 Ionic liquids recently have attracted special attention from the scientific community, and hundreds of studies that involve different aspects of ionic liquids have been presented in the literature. However, the critical properties that are required to estimate other properties for the modeling, simulation, and design of processes involving ionic liquids are not available. One reason for this is because the critical properties of ionic liquids cannot be experimentally determined, since most of these compounds start to decompose at low temperature and, in many cases, at temperatures approaching Tb. The estimated properties are useful approximations that must be interpreted as “these would be the values of TC, PC, Tb and ω, if the properties were possible to be measured”. Because of the fact that experimental data do not exist and there is no reasonable and generally accepted theory yet available to estimate these properties for ionic liquids, the group contribution method recently presented by Valderrama and Robles3 is considered to give reasonable estimates. * To whom correspondence should be addressed. Tel.: 56-51204260. Fax: 56-51-551158: E-mail address:
[email protected]. † Center for Technological Information (CIT). ‡ Faculty of Engineering, Department of Mechanical Engineering, University of La Serena. § Faculty of Chemical Engineering, Universidad Nacional del Altiplano. ⊥ Faculty of Sciences, Department of Physics, University of La Serena.
In addition to the aforementioned arguments, the critical properties (TC, PC, and VC), normal boiling temperature (Tb), and acentric factor (ω) are widely used in correlations and predictive methods to estimate a series of thermophysical and transport properties (such as vapor pressure, liquid density, viscosity, and thermal conductivity, among others).4 The corresponding state principle, which is based on equations of state or other methods of molecular nature, also makes use of the critical properties.5 In the case of ionic liquids, our previous studies indicate that extending estimation procedures originally derived for organic substances to ionic liquids, instead of developing complete new procedures for treating these new fluids, is a reasonable way to obtain these hypothetical properties, which are needed for other calculations.3 Among the several proposals presented in the literature, the approach developed by Lydersen1 is perhaps the most widely used group contribution method to estimate critical properties. Later, Joback and Reid2 developed a method that is frequently mentioned in the literature and used in several applications. In all these methods, the property of a compound is calculated by summing the contributions of certain defined groups of atoms, while simultaneously considering the number frequency of each group that is present in the molecule. Although all these methods have been questioned in the literature,4 they have the advantage of providing quick estimates without requiring sophisticated computational calculations. Alvarez and Valderrama6 combined the best results of Lydersen’s method with the best results of the Joback-Reid method to proposed a “modified Lydersen-Joback-Reid” method that proved to give good results for molecules with high molecular mass. The method considers the equations of the Lydersen method for the critical pressure and critical volume, and the equations of the Joback-Reid method for the normal boiling temperature and the critical temperature. The authors modified the parameters involved in the different equations for the critical properties. The equation for the normal boiling point was the same as that given in the original method. This modified Lydersen-Joback-Reid method was used by Valderrama and Robles3 to estimate the critical properties of 50 ionic liquids. Because there are no experimental critical
10.1021/ie071055d CCC: $40.75 © 2008 American Chemical Society Published on Web 01/18/2008
Ind. Eng. Chem. Res., Vol. 47, No. 4, 2008 1319 Table 1. Modified Group Contribution Methoda Model Equations
Tb ) 198.2 +
∑ n∆T
[ (
AM + B M
M
∑ n∆P + ∑ n∆V
CM +
V c ) EM
∑
n∆TM -
M
)
Table 2. Groups Considered in the Modified Lydersen-Joback-Reid Methoda group
AM ) 0.5703
bM
Tb
Tc )
Pc )
Constants
(∑ ) ] n∆TM
BM ) 1.0121
2
CM ) 0.2573 2
M
EM ) 6.75
a Data taken from ref 5. In the equations, M is given in units of g/mol, Tb and Tc are given in Kelvin, Pc is given in bars, and Vc is given in units of (cm3/mol).
∆TbM
∆TM
∆PM
∆VM
-CH3 -CH2>CH>C< [>C-]dCH2 dCHdC< -O[-O]>CdO -COO>N[>NC< dC< >N[>NNd]+
With Rings 27.15 0.0116 26.73 0.0114 21.32 -0.0180 31.01 0.0051 68.16 0.0063 57.55 -0.0011
0.1982 0.1693 0.0139 0.0955 0.0538 0.0559
51.64 42.55 17.62 31.28 25.17 42.15
-B -P -S[>S-]+ -SO2- *
New Groups -24.56 -0.0264 34.86 0.0067 117.52 -0.0004 147.24 -0.0563
0.0348 0.1776 0.6901 -0.0606
22.45 67.01 184.67 112.19
properties available to evaluate the accuracy of the estimates, these values were tested for accuracy and consistency by determining the density of the ionic liquids, for which experimental data are available. For this, an independent equation that was not applied in determining the critical properties was used. The deviations found between the experimental and calculated densities are within the experimental errors shown by the authors. However, the method has been questioned by Jones et al. in a recent communication.7 These authors compared 8 of the 50 estimated boiling temperatures with values derived from experimentally determined heats of vaporization. According to Jones et al.,7 the boiling temperatures of ionic liquids are not predicted well by the method used by Valderrama and Robles and, by inference, the critical properties and acentric factors also are likely to be erroneous. To reach this conclusion, Jones et al.7 extrapolated their heat of vaporization data using a constant value for the heat capacity difference [CPL - CPG] ) 94 J K-1 mol-1 for the 8 ionic liquids and then used Trouton’s Law: [∆Hvap(at 298 K) - 94(Tb - 298 K)]/(Tb) ) 85. In another communication, Valderrama and Robles8 discussed their own calculated values and extensively explained why those values seem to be reasonable and can be accepted for correlation and other calculations in which critical properties are required. These authors demonstrated that the heat capacity difference [CPL - CPG] that Jones et al.7 assumed to be constant (94 J K-1 mol-1) may vary from 15 J K-1 mol-1 to 287 J K-1 mol-1 for many fluids, and certainly this variation for ionic liquids is unknown. Also, Trouton’s constant, which was assumed by Jones et al.7 to be 85 J K-1 mol-1 ranges from 20 J K-1 mol-1 to 181 J K-1 mol-1 for many fluids. Also, in this case, the value of this constant, if it is constant, is unknown for ionic liquids. Therefore, assuming values of [CPL - CPG] ) 94 J K-1 mol-1 and [∆Hvap(at 298 K) -94(Tb - 298 K)]/Tb ) 85 are simply rough approximations that cannot be used for all ionic liquids without further analysis. Because experimental data do not exist and there is no reasonable and generally accepted theory yet available to estimate these properties for ionic liquids, the extension of standard methods such as group contribution seems to be reasonable. Also, the independent test of using the estimated critical properties to calculate the density of ionic liquids gives an indication of the consistency of the estimated values.
In these equations, FL is the liquid density (given in units of g/cm3), TR is the reduced temperature (TR ) T/TC), and TbR is the reduced temperature at the normal boiling point (TbR ) Tb/TC). The acentric factors (ω) of the ionic liquids were estimated as described by Valderrama and Robles,3 using the calculated critical properties and the calculated normal boiling temperature:
The Group Contribution Method
ω)
Details of the group contribution method has been given by Valderrama and Robles;3 therefore, it is only summarized in Tables 1 and 2. Table 1 shows the main equations for the normal
a
Data taken from ref 3. * Value determined in this work.
boiling temperature and the critical properties, whereas Table 2 lists the groups used to estimate the properties of the selected 200 ionic liquids. As a test of the “consistency” of the predicted properties, the liquid density of the ionic liquids has been estimated using a generalized correlation. In this work, a more flexible correlation that was proposed by one of the current authors have been used.9 This correlation has been shown to give accurate predictions for many fluids and is based on the equation of Shah and Yaws.10 It requires only the normal boiling temperature, the molecular mass, and the critical properties:
(
FL ) 0.01256 +
)[(
0.9533M VC
) ]
0.0039 0.2987 1.033 VC + M VC
Ψ
(1)
where
Ψ)-
[
]
1 - TR 1 - TbR
2/7
() ( ) () ()
(Tb - 43)(Tc - 43)
Pc Pb (Tc - Tb)(0.7Tc - 43) Tc - 43 Pc Pc log + log - 1 (2) Tc - T b Pb Pb log
26
25
24
23
22
21
20
19
18
17
16
15
14
13
12
11
10
9
8
7
6
5
4
3
2
1
No.
[P11] [tsac] [emim] [tsac] [TEA] [tsac] [TMAIA] [tsac] [TMEA] [tsac] [TMiPA] [tsac] [TMPA] [tsac] [bmim] [TFES] [dmim] [TFES] [emim] [TFES] [hpmim] [TFES] [bmim] [HFPS] [4,4,4,14-P] [HFPS] [bmim] [TPES] [6,6,6,14-P] [TPES] [bmim] [TTES] [bmim] [FS] [TMG] [Ac] [bmim] [Ac] [emim] [Ac] [emim] [BEI] [bmim] [BEI] [4MOPY] [BEI] [NH221] [BEI] [NH11(i-3)] [BEI] [C27guan] [bti]
ionic liquid
C29H58N4F6S2O4
C9H14N2O4S2F
C9H14N2O4S2F
C18H24N2O4S2F
C12H15F10N3O4S2
C10H11N3F10S2O4
C8H14N2O2
C10H18N2O2
C8H17N3O2
C12H16N2F8SO4
C11H16N2O4SF8
C36H69O4SF8
C12H16N2F8SO4
C29H57O3SF6
C11H16N2F6SO3
C13H22N2SF4
C8H12N2O3SF4
C18H32N2O3SF4
C10H16N2O3SF4
C9H16F6N2O3S
C9H16F6N2O3S
C8H14F6N2O3S
C9H14F6N2O3S
C11H20F6N2O3S
C9H11F6N3O3S
C9H14F6N2O3S
global formula 1,1-dimethylpyrrolidinium (2,2,2-trifluoro-n-(trifluoromethyl sulfonyl)acetamide 1-ethyl-3-methylidimazolium (2,2,2-trifluoro-n-(trifluoromethyl sulfonyl)acetamide tetraethylammonium (2,2,2-trifluoro-n-(trifluoromethyl sulfonyl)acetamide trimethylalylammonium (2,2,2-trifluoro-n-(trifluoromethyl sulfonyl)acetamide trimethylethylammonium (2,2,2-trifluoro-n-(trifluoromethyl sulfonyl)acetamide trimethylisopropylammonium (2,2,2-trifluoro-n-(trifluoromethyl sulfonyl)acetamide trimethylpropylammonium (2,2,2-trifluoro-n-(trifluoromethyl sulfonyl)acetamide 1-butyl-3-methylidimazolium 1,1,2,2-tetrafluoroethane sulfonate 1-dodecyl-3-methylidimazolium 1,1,2,2-tetrafluoroethane sulfonate 1-ethyl-3-methylidimazolium 1,1,2,2-tetrafluoroethane sulfonate 1-heptyl-3-methylidimazolium 1,1,2,2-tetrafluoroethane sulfonate 1-butyl-3-methylidimazolium 1,1,2,3,3,3-hexafluoropropane sulfonate tributyl(tetradecyl) phosphonium 1,1,2,3,3,3-hexafluoropropane sulfonate 1-butyl-3-methylidimazolium 1,1,2-trifluoro-2-(perfluoroethoxy)ethane sulfonate tetradecyl(trihexyl) phosphonium 1,1,2-trifluoro-2-(perfluoroethoxy)ethane sulfonate 1-butyl-3-methylidimazolium 1,1,2-trifluoro-2-(trifluoromethoxy)ethane sulfonate 1-butyl-3-methylidimazolium 2-(1,2,2,2-tetrafluoroethoxy)- 1,1,2,2-tetrafluoroethane sulfonate 1,1,3,3-tetramethyl guanidine acetate 1-butyl-3-methylidimazolium acetate 1-ethyl-3-methylidimazolium acetate 1-ethyl-3-methylidimazolium bis(pentafluoroethylsulfonyl)imide 1-butyl-3-methylidimazolium bis(pentafluoroethylsulfonyl)imide 4-methyl-n-octylpyridinium bis(pentafluoroethylsulfonyl)imide diethyl methyl (quaternary)ammonium bis (pentafluoroethylsulfonyl)imide dimethyl isopropyl (quaternary)ammonium bis(pentafluoroethylsulfonyl)imide [bis(bishexylamino)methylene]dimethylammonium bis[(trifluoromethyl)sulfonyl]imide
IUPAC name
705
468
468
587
505
491
170
198
175
436
386
750
436
631
370
362
292
433
320
346
346
332
344
374
1262.0
743.8
743.8
979.9
841.3
853.1
578.8
624.6
518.1
788.2
770.0
1201.5
788.2
1058.5
747.6
798.1
683.7
912.5
729.4
640.3
639.9
617.4
637.0
686.1
764.4
712.4
344 355
Tb (K)
M
1529.0
1056.3
1056.3
1291.4
1175.4
1231.4
807.1
847.3
703.7
1061.3
1058.3
1481.4
1061.3
1281.0
1032.1
1080.8
998.2
1171.0
1030.5
873.7
876.1
854.1
875.2
913.2
1069.9
999.5
TC (K)
9.8
21.5
21.5
15.0
19.3
21.9
29.2
24.5
28.0
17.9
20.9
7.0
17.9
8.8
21.3
20.7
30.4
15.6
25.7
21.7
21.9
23.3
22.5
19.1
25.2
24.2
PC (bar)
2167.1
1053.3
1053.3
1436.7
1117.4
1045.4
544.0
658.2
563.0
1012.9
928.2
2379.3
1012.9
2003.3
912.6
999.2
713.6
1284.7
827.8
855.9
854.2
798.8
842.3
970.2
833.5
813.1
VC (cm3/mol)
1.0120
0.3534
0.3534
0.5858
0.3837
0.2895
0.5889
0.6681
0.7326
0.5488
0.5085
0.5555
0.5488
0.9322
0.4933
0.5903
0.3743
0.8065
0.4583
0.5700
0.5536
0.5257
0.5475
0.6591
0.4977
0.4673
ω
298.15
298.15
298.15
298.15
298.10
298.15
298.15
298.15
298.15
298.15
298.15
298.15
298.15
298.15
298.15
301.15
301.45
301.35
301.45
298.15
298.15
298.15
298.15
298.15
298.15
298.15
T (K)
Fcalc (g/cm3) 1.4297 1.4553 1.3401 1.3736 1.3862 1.3662 1.3672 1.3016 1.2497 1.3447 1.2666 1.3909 1.2701 1.5136 1.2388 1.4371 1.5136 1.0248 1.0270 1.0388 1.5783 1.5478 1.4815 1.4833 1.4833 1.3305
Flit (g/cm3)a 1.430011 1.460011 1.370011 1.380011 1.400011 1.410011 1.380011 1.324012 1.136012 1.502012 1.274012 1.409012 1.070013 1.423012 1.063013 1.393012 1.449012 1.265014 1.055015 1.027015 1.590012 1.514016 1.390017 1.510018 1.530018 1.200019
Table 3. Critical Properties of Ionic Liquids Calculated by Group Contribution, Densities Calculated with the Generalized Correlation (eq 1), and Comparison with Literature Valuesa
10.9
-3.1
-1.8
6.6
2.2
-0.7
1.1
-2.6
-19.0
4.5
3.2
16.5
6.4
18.7
-1.3
-0.6
-10.5
10.0
-1.7
-0.9
-3.1
-1.0
-0.5
-2.2
-0.3
0.0
%∆F
1320 Ind. Eng. Chem. Res., Vol. 47, No. 4, 2008
52
51
50
49
48
47
46
45
44
43
42
41
40
39
38
37
36
35
34
33
32
31
30
29
28
27
No.
[C15guan] [bti] [dmprim] [bti] [dbim] [bti] [E1,3M4I] [bti] [dmim] [bti] [MP4] [bti] [bmpy] [bti] [decmim] [bti] [N-epy] [bti] [hpmim] [bti] [nmim] [bti] [pmim] [bti] [MP3] [bti] [prmim] [bti] [pmpy] [bti] [N723′3′] [bti] [dmeim] [bti] [BNM2E] [bti] [N1123] [bti] [N1134] [bti] [eomim] [bti] [N-bupy] [bti] [prmpyr] [bti] [tda] [bti] [thpa] [bti] [tha] [bti]
ionic liquid
Table 3. (Continued)
C26H52N2F6S2O4
C30H60N2F6S2O4
C42H84N2F6S2O4
C10H18N2F6S2O4
C11H14N2F6S2O4
C9H13N3F6S2O5
C11H22N2F6S2O4
C9H18N2F6S2O4
C10H20N2F6S2O4
C9H16N3F6S2O4
C17H34N2F6S2O4
C11H14N2F6S2O4
C9H13N3F6S2O4
C10H16N2F6S2O4
C11H17N3F6S2O4
C15H25N3F6S2O4
C13H21N3F6S2O4
C9H10F6N2O4S2
C16H27N3F6S2O4
C12H16N2F6S2O4
C11H18N2F6S2O4
C7H9N3F6S2O4
C10H15N3F6S2O4
C13H21N3F6S2O4
635
691
859
408
416
421
424
396
410
405
509
416
405
407
433
490
461
388
504
430
421
377
419
461
419
537
[bis(butylethylamino)methylene]dimethylammonium bis[(trifluoromethyl)sulfonyl]imide 1,2-dimethyl-3-propylimidazolium bis[(trifluoromethyl)sulfonyl]imide 1,3-dibutylimidazolium bis[(trifluoromethyl)sulfonyl]imide 1,3-diethyl-4-methylidimazolium bis[(trifluoromethyl)sulfonyl]imide 1,3-dimethylidimazolium bis[(trifluoromethyl)sulfonyl]imide 1-butyl-2-methylpyrrolidinium bis[(trifluoromethyl)sulfonyl]imide 1-butyl-3-methylpyridinium bis[(trifluoromethyl)sulfonyl]imide 1-decyl-3-methylidimazolium bis[(trifluoromethyl)sulfonyl]imide 1-ethylpyridinium bis[(trifluoromethyl)sulfonyl]imide 1-heptyl-3-methylidimazolium bis[(trifluoromethyl)sulfonyl]imide 1-nonyl-3-methylidimazolium bis[(trifluoromethyl)sulfonyl]imide 1-pentyl-3-methylidimazolium bis[(trifluoromethyl)sulfonyl]imide 1-propyl-2-methylpyrrolidinuim bis[(trifluoromethyl)sulfonyl]imide 1-propyl-3-methylidimazolium bis[(trifluoromethyl)sulfonyl]imide 3-methyl-1-propylpyridinium bis[(trifluoromethyl)sulfonyl]imide di(iso)propylethylheptylammonium bis[(trifluoromethyl)sulfonyl]imide dimethyl-3-ethylimidazolium bis[(trifluoromethyl)sulfonyl]imide dimethylethylbutylammonium bis[(trifluoromethyl)sulfonyl]imide dimethylethylpropylammonium bis[(trifluoromethyl)sulfonyl]imide dimethylpropylbutylammonium bis[(trifluoromethyl)sulfonyl]imide ethoxymethyl-3-methylidimazolium bis[(trifluoromethyl)sulfonyl]imide n-butylpyridinium bis[(trifluoromethyl)sulfonyl]imide n-methyl-n-propylpyrrolidinium bis[(trifluoromethyl)sulfonyl]imide tetradecylammonium bis[(trifluoromethyl)sulfonyl]imide tetraheptylammonium bis[(trifluoromethyl)sulfonyl]imide tetrahexylammonium bis[(trifluoromethyl)sulfonyl]imide
C17H34N4F6S2O4
C10H15F6N3O4S2
M
IUPAC name
global formula
1104.4
1195.9
1470.5
810.4
824.2
862.0
761.2
715.4
738.3
833.9
897.6
829.1
839.6
810.0
885.3
976.8
931.1
778.4
999.7
852.0
832.9
783.2
867.4
931.1
867.4
987.5
Tb (K)
1353.0
1449.6
1831.8
1196.9
1229.1
1285.2
1070.1
1038.7
1054.3
1254.1
1176.6
1228.9
1259.3
1196.5
1281.1
1331.2
1305.0
1207.9
1345.1
1240.5
1208.8
1235.7
1269.7
1305.0
1269.7
1271.0
TC (K)
11.0
9.7
7.0
26.7
27.7
29.0
22.5
25.9
24.1
29.7
16.1
27.5
29.9
27.0
25.6
19.8
22.3
32.7
18.7
25.5
25.1
35.8
27.5
22.3
27.5
15.6
PC (bar)
1926.4
2154.8
2840.1
969.8
983.3
948.6
1069.7
955.5
1012.6
948.4
1408.9
981.7
933.0
960.7
1047.2
1275.7
1161.5
869.0
1332.8
1038.8
1017.8
835.8
988.6
1161.5
988.6
1481.8
VC (cm3/mol)
0.9857
0.9913
0.4734
0.2754
0.2505
0.2694
0.4228
0.3334
0.3777
0.2447
0.6653
0.2723
0.2573
0.2783
0.3442
0.5276
0.4349
0.1671
0.5741
0.3160
0.3220
0.1418
0.3226
0.4349
0.3226
0.7803
ω
298.15
298.15
298.15
293.15
298.15
298.15
293.15
293.15
293.15
298.15
293.15
298.15
298.15
293.15
298.15
298.15
298.15
298.15
298.15
298.15
293.15
295.15
295.15
298.15
295.15
298.15
T (K)
Fcalc (g/cm3) 1.3468 1.4177 1.3679 1.4177 1.4417 1.3810 1.3821 1.3489 1.4341 1.3679 1.3535 1.3907 1.3978 1.4270 1.3986 1.3057 1.3996 1.3500 1.3647 1.3383 1.4675 1.3900 1.3912 1.1795 1.3034 1.3119
Flit (g/cm3)a 1.360019 1.456716 1.491020 1.432020 1.559016 1.430020 1.412012 1.271020 1.536016 1.344020 1.299020 1.403020 1.460020 1.475020 1.444012 1.270020 1.480216 1.370020 1.410020 1.340020 1.496020 1.449020 1.459020 1.040020 1.100020 1.110020
18.2
18.5
13.4
-4.6
-4.1
-1.9
-0.1
-3.2
-1.5
-5.4
2.8
-3.1
-3.3
-4.3
-0.9
4.2
1.8
-6.6
6.1
-2.1
-3.4
-7.5
-1.0
-8.3
-2.7
-1.0
%∆F
Ind. Eng. Chem. Res., Vol. 47, No. 4, 2008 1321
78
77
76
75
74
73
72
71
70
69
68
67
66
65
64
63
62
61
60
59
58
57
56
55
54
53
No.
[tpa] [bti] [toa] [bti] [S444] [bti] [N7444] [bti] [N6444] [bti] [N1444] [bti] [N8444] [bti] [N7222] [bti] [N6222] [bti] [N8222] [bti] [S222] [bti] [N1114] [bti] [N7111] [bti] [N6111] [bti] [N111C2O] [bti] [N8111] [bti] [tmpa] [bti] [S111] [bti] [Ph(CH2)mim] [bti] [Ph(CH2)2mim] [bti] [Ph(CH2)3mim] [bti] [dmeim] [bti] [dmpim] [bti] [bdmim] [bti] [mbpyr] [bti] [bmpyr] [bti]
ionic liquid
Table 3. (Continued)
C10H17N2F6S2O4
C12H16N2O4S2F6
C11H17N3F6S2O4
C10H15N3F6S2O4
C8H12N3O4S2F6
C15H17N3O4S2F6
C14H15N3O4S2F6
C13H13N3O4S2F6
C5H9NF6S3O4
C8H16N2F6S2O4
C13H26N2F6S2O4
C7H14N2F6S2O5
C11H22N2F6S2O4
C12H24N2F6S2O4
C9H18N2F6S2O4
C8H15NF6S3O4
C16H32N2F6S2O4
C14H28N2F6S2O4
C15H30N2F6S2O4
C22H44F6N2O4S2
C15H30F6N2O4S2
C20H40F6N2O4S2
C21H42F6N2O4S2
C14H27NF6S3O4
422
430
433
419
392
481
467
453
357
382
452
384
424
438
396
399
495
467
481
579
481
551
565
484
747
579
tetramylammonium bis[(trifluoromethyl)sulfonyl]imide tetraoctylammonium bis[(trifluoromethyl)sulfonyl]imide tributylsulfonium bis[(trifluoromethyl)sulfonyl]imide tributylheptylammonium bis[(trifluoromethyl)sulfonyl]imide tributylhexylammonium bis[(trifluoromethyl)sulfonyl]imide tributylmethylammonium bis[(trifluoromethyl)sulfonyl]imide tributyloctylammonium bis[(trifluoromethyl)sulfonyl]imide triethylheptylammonium bis[(trifluoromethyl)sulfonyl]imide triethylhexylammonium bis[(trifluoromethyl)sulfonyl]imide triethyloctylammonium bis[(trifluoromethyl)sulfonyl]imide triethylsulfonium bis[(trifluoromethyl)sulfonyl]imide trimethylbutylammonium bis[(trifluoromethyl)sulfonyl]imide trimethylheptylammonium bis[(trifluoromethyl)sulfonyl]imide trimethylhexylammonium bis[(trifluoromethyl)sulfonyl]imide trimethylmethoxymethylammonium bis[(trifluoromethyl)sulfonyl]imide trimethyloctylammonium bis[(trifluoromethyl)sulfonyl]imide trimethylpropylammonium bis[(trifluoromethyl)sulfonyl]imide trimethylsulfonium bis[(trifluoromethyl)sulfonyl]imide 1-(1-phenylalkyl)-3-methylidimazolium bis[(trifluoromethyl)sulfonyl]imide 1-(2-phenylalkyl)-3-methylidimazolium bis[(trifluoromethyl)sulfonyl]imide 1-(3-phenylalkyl)-3-methylidimazolium bis[(trifluoromethyl)sulfonyl]imide 1,2-dimethyl-3-ethylimidazolium bis[(trifluoromethyl)sulfonyl]imide 1,2-dimethyl-3-propylimidazolium bis[(trifluoromethyl)sulfonyl]imide 1-butyl-2,3-dimethylidimazolium bis[(trifluoromethyl)sulfonyl]imide 1-butyl-4-methylpyridinium bis[(trifluoromethyl)sulfonyl]imide 1-butyl-1-methylpyrrolidinium bis[(trifluoromethyl)sulfonyl]imide
C22H44N2F6S2O4
C34H68N2F6S2O4
M
IUPAC name
global formula
833.3
852.0
890.3
867.4
817.8
993.8
971.0
948.1
729.0
692.6
807.0
692.1
761.2
784.1
715.4
797.6
875.6
829.8
852.7
1012.9
852.7
967.1
990.0
934.9
1287.4
1012.9
Tb (K)
1209.2
1240.5
1281.1
1269.7
1235.8
1444.9
1436.9
1429.7
1156.5
1023.4
1102.5
1035.7
1070.1
1086.1
1038.7
1189.9
1153.7
1119.2
1136.3
1267.0
1136.3
1227.4
1247.0
1269.2
1559.2
1267.0
TC (K)
24.8
25.5
25.5
27.5
31.6
24.3
26.1
28.1
27.3
28.0
19.8
29.5
22.5
21.1
25.9
21.9
16.8
18.7
17.7
12.8
17.7
13.9
13.3
15.6
8.6
12.8
PC (bar)
1026.9
1038.8
1045.7
988.6
888.9
1153.7
1096.6
1039.5
875.3
898.4
1183.9
856.9
1069.7
1126.8
955.5
1046.6
1355.3
1241.0
1298.1
1697.9
1298.1
1583.7
1640.8
1389.3
2383.2
1697.9
VC (cm3/mol)
0.3191
0.3160
0.3669
0.3226
0.2492
0.3018
0.2573
0.2139
0.0384
0.2900
0.5146
0.2599
0.4228
0.4685
0.3334
0.1603
0.6522
0.5608
0.6068
0.8923
0.6068
0.8216
0.8585
0.4263
0.8960
0.8923
ω
298.15
298.15
298.15
299.15
293.15
298.15
298.15
298.15
318.15
298.15
293.15
298.15
293.15
293.15
293.15
298.15
293.15
293.15
293.15
293.15
296.9
293.15
293.15
298.15
298.15
298.15
T (K)
Fcalc (g/cm3) 1.3100 1.2782 1.2200 1.3115 1.3106 1.3114 1.3126 1.3136 1.3171 1.3113 1.2435 1.3647 1.3292 1.3383 1.4469 1.3222 1.3797 1.2758 1.4395 1.4227 1.4089 1.4457 1.4157 1.3999 1.3821 1.3724
Flit (g/cm3)a 1.160020 1.060020 1.290020 1.170020 1.150020 1.266016 1.120020 1.260020 1.270020 1.250020 1.460020 1.410020 1.280020 1.330020 1.510020 1.270020 1.440020 1.580020 1.491021 1.470021 1.455021 1.510022 1.481012 1.420023 1.350024 1.394016
-1.6
2.4
-1.4
-4.4
-4.3
-3.2
-3.2
-3.5
-19.3
-4.2
4.1
-4.2
0.6
3.8
-3.2
-14.8
4.9
3.7
4.3
17.2
3.6
14.0
12.1
-5.4
20.6
12.9
%∆F
1322 Ind. Eng. Chem. Res., Vol. 47, No. 4, 2008
104
103
102
101
100
99
98
97
96
95
94
93
92
91
90
89
88
87
86
85
84
83
82
81
80
79
No.
[bpyr] [bti] [C12mim] [bti] [memim] [bti] [mmim] [bti] [pdmim] [bti] [C2F3mim] [bti] [4MOPY] [bti] [C23guan] [bti] [S224] [bti] [NH221] [bti] [S221] [bti] [S225] [bti] [S223] [bti] [NH114] [bti] [S114] [bti] [S112] [bti] [NH11(i-3)] [bti] [S115] [bti] [S113] [bti] [S124] [bti] [S125] [bti] [S123] [bti] [DEME] [bti] [BMP] [bti] [S444] [bti] [N222(2O1)] [bti]
ionic liquid
Table 3. (Continued)
C11H22N2O5S2F6
C14H27NO4S3F6
C12H22N2O4S2F6
C10H20N2O5S2F6
C8H15NO4S3F6
C10H19NO4S3F6
C9H17NO4S3F6
C7H13NO4S3F6
C9H17NO4S3F6
C7H14N2O4S2F6
C6H11NO4S3F6
C8H15NO4S3F6
C8H16N2O4S2F6
C9H17NO4S3F6
C11H21NO4S3F6
C7H13NO4S3F6
C7H14N2O4S2F6
C10H19NO4S3F6
C25H50N4O4S2F6
C16H24N2O4S2F6
C7H6N3O4S2F9
C10H15N3F6S2O4
C7H9N3F6S2O4
C8H12N3O4S2F6
440
484
436
426
399
427
413
385
413
368
371
399
382
413
441
385
368
427
649
487
431
419
377
392
532
416
1-butylpyridinium bis[(trifluoromethyl)sulfonyl]imide 1-dodecyl-3-methylimidazolium bis[(trifluoromethyl)sulfonyl]imide 1-methyl-3-ethyl-4-methylimidazolium bis[(trifluoromethyl)sulfonyl]imide 1-methyl-3-methylidimazolium bis[(trifluoromethyl)sulfonyl]imide 1-propyl-2,3-dimethylidimazolium bis[(trifluoromethyl)sulfonyl]imide 1-trifluoroethyl-3-methylidimazolium bis[(trifluoromethyl)sulfonyl]imide 4-methyl-n-octylpyridinium bis[(trifluoromethyl)sulfonyl]imide bis-hexyl-aminomethylene dimethylammonium bis[(trifluoromethyl)sulfonyl]imide diethylbutylsulfonium bis[(trifluoromethyl)sulfonyl]imide diethylmethyl(quaternary)ammonium bis[(trifluoromethyl)sulfonyl]imide diethylmethylsulfonium bis[(trifluoromethyl)sulfonyl]imide diethylpentylsulfonium bis[(trifluoromethyl)sulfonyl]imide diethylpropylsulfonium bis[(trifluoromethyl)sulfonyl]imide dimethylbutyl (quaternary)ammonium bis[(trifluoromethyl)sulfonyl]imide dimethylbutylsulfonium bis[(trifluoromethyl)sulfonyl]imide dimethylethylsulfonium bis[(trifluoromethyl)sulfonyl]imide dimethylisopropyl(quaternary)ammonium bis[(trifluoromethyl)sulfonyl]imide dimethylpentylsulfonium bis[(trifluoromethyl)sulfonyl]imide dimethylpropylsulfonium bis[(trifluoromethyl)sulfonyl]imide methylethylbutylsulfonium bis[(trifluoromethyl)sulfonyl]imide methylethylpentylsulfonium bis[(trifluoromethyl)sulfonyl]imide methylethylpropylsulfonium bis[(trifluoromethyl)sulfonyl]imide N,N-diethyl-N-methyl-N-(2-methoxyethyl)ammonium bis[(trifluoromethyl)sulfonyl]imide N-butyl-N-methylpiperidinium bis[(trifluoromethyl)sulfonyl]imide tributylsulfonium bis[(trifluoromethyl)sulfonyl]imide triethyl(2-methoxyethyl)ammonium bis[(trifluoromethyl)sulfonyl]imide
C11H14F6N2O4S2
C18H31N3O4S2F6
M
IUPAC name
global formula
783.6
934.9
860.5
760.7
797.6
843.4
820.5
774.8
820.5
707.4
751.9
797.6
730.3
820.5
866.3
774.8
707.4
843.4
1170.5
943.5
788.8
867.4
793.8
817.8
1045.5
824.2
Tb (K)
1096.3
1269.2
1233.4
1080.7
1189.9
1214.5
1202.0
1178.3
1202.0
1061.1
1167.2
1189.9
1075.3
1202.0
1227.5
1178.3
1061.1
1214.5
1432.1
1292.0
1202.7
1269.7
1239.9
1235.8
1374.6
1229.1
TC (K)
22.0
15.6
23.4
23.5
21.9
19.3
20.5
23.4
20.5
31.9
25.2
21.9
29.3
20.5
18.2
23.4
31.9
19.3
11.2
19.7
29.2
27.5
35.8
31.6
16.8
27.7
PC (bar)
1085.3
1389.3
1078.5
1028.2
1046.6
1160.9
1103.8
989.5
1103.8
883.8
932.4
1046.6
940.9
1103.8
1218.0
989.5
883.8
1160.9
1938.7
1267.2
871.5
988.6
818.8
888.9
1447.0
983.3
VC (cm3/mol)
0.4370
0.4263
0.3472
0.3915
0.1603
0.2465
0.2030
0.1186
0.2030
0.2805
0.0779
0.1603
0.3229
0.2030
0.2908
0.1186
0.2805
0.2465
1.0159
0.4983
0.1879
0.3226
0.1752
0.2492
0.6662
0.2505
ω
298.15
298.00
298.15
293.15
298.15
298.15
298.15
298.15
298.15
298.15
298.15
298.15
298.15
298.15
298.15
298.15
298.15
298.15
298.15
298.15
293.15
295.15
295.15
293.15
293.15
298.10
T (K)
Fcalc (g/cm3) 1.3901 1.3459 1.4457 1.4827 1.4177 1.6092 1.3439 1.3437 1.2288 1.3442 1.2544 1.2244 1.2351 1.3265 1.2435 1.2683 1.3442 1.2351 1.2544 1.2351 1.2288 1.2435 1.3911 1.3632 1.2200 1.3753
Flit (g/cm3)a 1.499016 1.246025 1.470022 1.559026 1.456727 1.660022 1.290017 1.200020 1.310028 1.430018 1.430028 1.300028 1.340028 1.390018 1.550028 1.560028 1.420018 1.350028 1.390028 1.260028 1.260028 1.340028 1.420029 1.380023 1.290030 1.400031
-1.8
-5.4
-1.2
-2.0
-7.2
-2.5
-2.0
-9.8
-8.5
-5.3
-18.7
-19.8
-4.6
-7.8
-5.8
-12.3
-6.0
-6.2
12.0
4.2
-3.1
-2.7
-4.9
-1.7
8.0
-7.3
%∆F
Ind. Eng. Chem. Res., Vol. 47, No. 4, 2008 1323
130
129
128
127
126
125
124
123
122
121
120
119
118
117
116
115
114
113
112
111
110
109
108
107
106
105
No.
[P222(2O1)] [bti] [N222(1O1)] [bti] [P222(1O1)] [bti] [NH222] [bti] [N222(12)] [bti] [P222(12)] [bti] [N2228] [bti] [P2228] [bti] [N2225] [bti] [P2225] [bti] [bmim] [Br] [C27guan] [Cl] [C35guan] [Cl] [moeemim] [Cl] [bmim] [Cl] [hmim] [Cl] [omim] [Cl] [Bemim] [Cl] [C12mim] [Cl] [emim] [Cl] [mmim] [Cl] [mim] [Cl] [ClBenmim] [Cl] [FBenMim] [Cl] [C23guan] [Cl] [dbim] [Cl]
ionic liquid
Table 3. (Continued)
C11H21N2Cl
C23H50N3Cl
C11H12N2ClF
C11H12N2Cl2
C4H7N2Cl
C5H9N2Cl
C6H11ClN2
C16H31N2Cl
C11H13ClN2
C12H23ClN2
C10H19N2Cl
C8H15N2Cl
C9H17N2O2Cl
C35H74N3Cl
C27H58N3Cl
C8H15BrN2
C13H26NO4S2F6
C13H26N2O4S2F6
C16H32NO4S2F6
C16H32N2O4S2F6
C20H40NO4S2F6
C20H40N2O4S2F6
C8H16N2O4S2F6
C10H20NO5S2F6
217
404
227
243
119
133
147
287
209
231
203
175
221
572
460
219
469
452
512
495
568
551
382
443
426
457
triethyl(2-methoxyethyl)phosphonium bis[(trifluoromethyl)sulfonyl]imide triethyl(methoxymethyl)ammonium bis[(trifluoromethyl)sulfonyl]imide triethyl(methoxymethyl)phosphonium bis[(trifluoromethyl)sulfonyl]imide triethyl(quaternary)ammonium bis[(trifluoromethyl)sulfonyl]imide triethyldodecylammonium bis[(trifluoromethyl)sulfonyl]imide triethyldodecyl phosphonium bis[(trifluoromethyl)sulfonyl]imide triethyloctyl ammonium bis[(trifluoromethyl)sulfonyl]imide triethyloctylphosphonium bis[(trifluoromethyl)sulfonyl]imide triethylpentylammonium bis[(trifluoromethyl)sulfonyl]imide triethylpentylphosphonium bis[(trifluoromethyl)sulfonyl]imide 1-butyl-3-methylidimazolium bromide [bis(bis-hexyl-amino)methylene]dimethylammonium chloride [bis(bis-octyl-amino)methylene]dimethylammonium chloride 1-[2-(2-methoxyethoxy)ethyl]-3-methylidimazolium chloride 1-butyl-3-methylidimazolium chloride 1-hexyl-3-methylidimazolium chloride 1-octyl-3-methylidimazolium chloride 1-benzyl-3-methylidimazolium chloride 1-dodecyl-3-methylidimazolium chloride 1-ethyl-3-methylidimazolium chloride 1-methyl-3-methylidimazolium chloride 1-methylidimazolium chloride 1-p-chlorobenzyl-3-methylidimazolium chloride 1-p-fluorobenzyl-3-methylidimazolium chloride bis-hexyl-amino-methylenedimethylammonium chloride 1,3-dibutylimidazolium chloride
C11H22NO5S2F6
C10H20N2O5S2F6
M
IUPAC name
global formula
626.7
866.1
657.6
695.8
461.1
489.4
512.3
741.1
653.4
649.6
603.8
558.0
625.8
1140.7
957.6
586.8
830.1
807.0
898.7
875.6
990.2
967.1
730.3
783.9
760.7
806.7
Tb (K)
849.2
1052.1
913.1
969.6
687.7
728.2
748.6
951.5
921.3
869.4
829.2
789.0
863.6
1411.1
1158.9
834.9
1139.5
1102.5
1188.7
1153.7
1260.3
1227.4
1075.3
1119.8
1080.7
1134.6
TC (K)
21.8
10.5
26.4
26.8
48.2
38.5
34.2
16.0
28.4
20.3
23.5
27.8
24.8
7.4
9.2
29.8
19.3
19.8
16.4
16.8
13.7
13.9
29.3
22.8
23.5
21.4
PC (bar)
740.1
1517.3
652.0
682.6
316.1
397.4
454.5
1025.6
631.8
797.2
683.0
568.8
657.1
2202.6
1745.7
583.3
1224.2
1183.9
1395.6
1355.3
1624.0
1583.7
940.9
1068.5
1028.2
1125.6
VC (cm3/mol)
0.6144
1.0428
0.5660
0.5521
0.4564
0.3825
0.4165
0.8212
0.5145
0.6566
0.5725
0.4908
0.5707
0.5680
0.9692
0.4891
0.4757
0.5146
0.6140
0.6523
0.7861
0.8216
0.3229
0.3525
0.3915
0.3980
ω
298.15
298.15
298.15
298.15
353.15
298.15
294.65
298.15
298.15
298.1
298.15
298.15
298.15
298.15
298.15
298.40
298.15
298.15
298.15
298.15
298.15
298.15
298.15
298.15
298.15
298.15
T (K)
Fcalc (g/cm3) 1.3747 1.3880 1.3865 1.3265 1.3079 1.3122 1.3085 1.3117 1.3193 1.3214 1.2327 1.0530 1.0105 1.1322 0.9998 0.9944 0.9968 1.1066 1.0153 1.0260 1.0446 1.1121 1.2126 1.1779 1.0491 0.9948
Flit (g/cm3)a 1.390031 1.440031 1.420031 1.360018 1.220031 1.210031 1.280031 1.260031 1.330031 1.320031 1.299032 0.900019 0.960019 1.140020 1.080020 1.030020 1.000016 1.193014 0.880632 1.186016 1.139920 1.183215 1.267014 1.283014 0.900020 1.008220
-1.3
16.6
-8.2
-4.3
-6.0
-8.4
-13.5
15.3
-7.2
-0.3
-3.5
-7.4
-0.7
5.3
17.0
-5.1
0.1
-0.8
4.1
2.2
8.4
7.2
-2.5
-2.4
-3.6
-1.1
%∆F
1324 Ind. Eng. Chem. Res., Vol. 47, No. 4, 2008
156
155
154
153
152
151
150
149
148
147
146
145
144
143
142
141
140
139
138
137
136
135
134
133
132
131
No.
[bmim] [dca] [emim] [dca] [omim] [dca] [4MOPY] [dca] [emim] [dca] [mbpyr] [dca] [mhpyr] [dca] [mppyr] [dca] [emim] [DEGlyMSO4] [dmim] [DMPO4] [py] [EOESO4] [edmim] [ESO4] [emim] [ESO4] [moim] [PF6] [moeemim] [PF6] [bdmim] [PF6] [hpmim] [PF6] [nmim] [PF6] [oprim] [PF6] [pmim] [PF6] [eommim] [PF6] [mommim] [PF6] [N-bupy] [PF6] [Ph(CH2)3mim] [PF6] [prmim] [PF6] [C2C6I] [PF6]
ionic liquid
Table 3. (Continued)
C11H21N2F6P
C7H13F6N2P
C13H17N2F6P
C9H14NPF6
C6H11N2OPF6
C7H13N2OPF6
C9H17F6N2P
C14H27N2PF6
C13H25N2PF6
C11H21N2PF6
C9H17F6N2P
C9H17N2O2PF6
C12H23N2PF6
C8H16N2O4S
C9H18N2O4S
C9H15NO5S
C7H15N2O4P
C11H22N2O6S
C10H18N4
C13H24N4
C11H20N4
C8H11N5
C16H24N4
C14H23N5
C8H11N5
C10H15N5
global formula 205
1-butyl-3-methylidimazolium dicyanamide 1-ethyl-3-methylidimazolium dicyanamide 1-octyl-3-methylidimazolium dicyanamide 4-methyl-n-octylpyridinium dicyanamide 1-ethyl-3-methylidimazolium dicyanoamides n-methyl-n-butylpyrrolidinium dicyanoamides n-methyl-n-hexylpyrrolidinium dicyanoamides n-methyl-n-propylpyrrolidinium dicyanoamides 1-ethyl-3-methylidimazolium diethyleneglycol monomethylethersulfate 1,3-dimethylidimazolium dimethyl phosphate pyridinium ethoxyethyl sulfate 1-ethyl-2,3-dimethylidimazolium ethyl sulfate 1-ethyl-3-methylidimazolium ethyl sulfate 1-octyl-3-methylidimazolium hexafluorophosphate 1-[2-(2-methoxyethoxy)ethyl]-3-methylidimazolium hexafluorophosphate 1-butyl-2,3-dimethylidimazolium hexafluorophosphate 1-heptyl-3-methylidimazolium hexafluorophosphate 1-nonyl-3-methylidimazolium hexafluorophosphate 1-octyl-3-propylimidazolium hexafluorophosphate 1-pentyl-3-methylidimazolium hexafluorophosphate ethoxymethyl-3-methylidimazolium hexafluorophosphate methyloxymethyl-3-methylidimazolium hexafluorophosphate n-butylpyridinium hexafluorophosphate 1-(3-phenylalkyl)-3-methylidimazolium hexafluorophosphate 1-propyl-3-methylidimazolium hexafluorophosphate 1-hexyl-3-ethylimidazolium hexafluorophosphate 326
270
346
281
272
286
298
368
354
326
298
330
340
236
250
248
222
310
194
236
208
177
272
261
177
M
IUPAC name
623.2
531.7
686.0
516.3
531.2
554.1
577.5
691.9
669.0
623.2
582.4
622.3
635.5
712.7
740.5
696.1
623.0
826.2
730.9
799.6
753.8
737.2
864.1
863.9
737.2
783.0
Tb (K)
787.8
696.7
883.8
674.4
701.2
723.7
742.1
857.6
834.1
787.8
746.3
795.3
800.1
1067.5
1082.6
1065.4
880.4
1162.9
968.8
1028.0
988.3
999.0
1094.3
1103.9
999.0
1035.8
TC (K)
14.7
18.3
16.3
17.3
19.3
18.2
16.3
12.8
13.4
14.7
16.2
16.1
14.0
40.5
35.8
41.8
28.6
28.1
22.9
18.6
21.3
29.1
17.2
18.4
29.1
24.4
PC (bar)
933.8
705.4
926.1
755.6
663.9
721.0
819.6
1105.2
1048.1
933.8
818.0
850.8
1007.9
659.8
715.3
658.8
598.4
862.3
691.7
863.0
748.8
597.8
989.1
957.4
597.8
712.0
VC (cm3/mol)
0.9055
0.7504
0.8053
0.7381
0.7274
0.7692
0.8316
0.9937
0.9680
0.9055
0.8526
0.8676
0.9069
0.3744
0.4341
0.2994
0.5065
0.5176
0.7920
0.9087
0.8316
0.7661
0.9923
0.9543
0.7661
0.8419
ω
298.15
293.00
298.15
298.15
298.15
298.15
294.1
298.15
298.15
298.15
295.65
298.15
298.15
298.15
353.15
298.15
303.15
298.15
298.15
298.15
298.15
298.15
298.15
298.15
298.15
297.15
T (K)
Fcalc (g/cm3) 1.0406 1.0451 1.0229 1.0422 1.0451 1.0042 1.0123 1.0018 1.2331 1.2322 1.2188 1.1327 1.1699 1.2216 1.3869 1.2832 1.2577 1.2499 1.2473 1.2757 1.3595 1.3815 1.2487 1.3452 1.3018 1.2577
Flit (g/cm3)a 1.058016 1.060026 1.000024 0.980017 1.060020 0.950020 0.920020 0.920020 1.236534 1.253016 1.281016 1.197015 1.238835 1.236016 1.320020 1.241616 1.262020 1.212020 1.118220 1.333016 1.400020 1.480020 1.214420 1.407021 1.333030 1.262220
-0.4
-2.3
-4.4
2.8
-6.7
-2.9
-4.3
11.5
3.1
-0.3
3.4
5.1
-1.1
-5.6
-5.4
-4.9
-1.7
-0.3
8.9
10.0
5.7
-1.4
6.3
2.3
-1.4
-1.6
%∆F
Ind. Eng. Chem. Res., Vol. 47, No. 4, 2008 1325
182
181
180
179
178
177
176
175
174
173
172
171
170
169
168
167
166
165
164
163
162
161
160
159
158
157
No.
[C2C8I] [PF6] [bmim] [HSO4] [emim] [HSO4] [mim] [HSO4] [bmim] [I] [TMG] [Lac] [bmim] [mesy] [emim] [mesy] [dmim] [MOESO4] [dmim] [MSO4] [bmim] [MSO4] [MMMPZ] [MSO4] [MTEOA] [MSO4] [bmim] [NfO] [omim] [NfO] [bmim] [C8S] [tibmp] [pTSO3] [Ch] [Sa] [C27guan] [BF4] [C15guan] [BF4] [moeoemim] [BF4] [bdmim] [BF4] [dmim] [BF4] [N-epy] [BF4] [prmim] [BF4] [moemim] [BF4]
ionic liquid
Table 3. (Continued)
C7H13N2OBF4
C7H13N2BF4
C7H10BF4N
C14H27N2BF4
C9H17N2BF4
C9H17N2O2BF4
C15H34N3BF4
C27H58N3BF4
C12H19NO4
C20H37O3PS
C16H32N2O4S
C16H23N2O3SF9
C12H15N2F9SO3
C8H21NO7S
C7H14N2O4S
C9H18N2O4S
C6H12N2O4S
C8H16N2O5S
C7H14N2O3S
C9H18N2O3S
C8H19N3O3
C8H15N2I
C4H8N2SO4
C6H12N2O4S
C8H16N2O4S
C13H25N2F6P
global formula
[bis(bis-hexylamino)methylene]dimethylammonium tetrafluoroborate [bis(butyl-ethylamino)methylene]dimethylammonium tetrafluoroborate 1-[2-(2-methoxyethoxy)ethyl]-3-methylidimazolium tetrafluoroborate 1-butyl-2,3-dimethylidimazolium tetrafluoroborate 1-decyl-3-methylidimazolium tetrafluoroborate 1-ethylpyridinium tetrafluoroborate 1-propyl-3-methylidimazolium tetrafluoroborate ethyloxymethyl-3-methylidimazolium tetrafluoroborate
1-octyl-3-ethylimidazolium hexafluorophosphate 1-butyl-3-methylidimazolium hydrogen sulfate 1-ethyl-3-methylidimazolium hydrogen sulfate 1-methylidimazolium hydrogen sulfate 1-butyl-3-methylidimazolium iodide 1,1,3,3-tetramethyl guanidine lactate 1-butyl-3-methylidimazolium methane sulfonate 1-ethyl-3-methylidimazolium methane sulfonate 1,3-dimethylidimazolium methoxyethyl sulfate 1,3-dimethylidimazolium methyl sulfate 1-butyl-3-methylidimazolium methyl sulfate 1,2,4-trimethylpyrazolium methylsulfate tris(2-hydroxyethyl)methylammonium methyl sulfate 1-butyl-3-methylidimazolium nonafluorobutane sulfonate 1-octyl-3-methylidimazolium nonafluorobutane sulfonate 1-butyl-3-methylidimazolium octyl sulfate triisobutylmethyl phosphonium p-toluene sulfonate choline salicylate
IUPAC name
228
212
195
310
240
272
343
512
240
389
349
494
438
273
222
250
208
252
206
234
204
266
179
207
494.8
472.3
411.2
632.5
523.1
562.9
620.3
894.8
762.2
874.8
895.7
843.2
762.3
865.1
694.8
735.6
666.9
735.1
667.4
713.1
632.7
613.7
685.5
736.7
782.4
669.0
354 235
Tb (K)
M
647.0
619.7
549.9
784.6
671.0
720.2
755.9
1100.3
950.5
1176.4
1189.8
1094.2
1028.8
1093.4
1054.2
1081.6
1040.0
1094.4
1026.0
1054.8
816.9
871.2
1019.6
1073.8
1103.8
834.1
TC (K)
21.7
21.8
23.5
14.5
18.9
18.8
12.2
8.2
23.7
18.2
20.2
14.2
17.3
34.9
45.4
36.1
52.9
38.9
48.1
37.4
27.1
28.6
91.7
57.4
43.2
13.4
PC (bar)
613.5
597.9
533.9
997.7
710.5
743.3
1146.7
1832.0
726.4
1249.9
1116.7
1250.2
1004.8
744.3
601.1
716.9
545.6
675.4
587.1
701.3
639.1
607.5
412.2
550.7
664.9
1048.1
VC (cm3/mol)
0.8686
0.8479
0.7495
1.0817
0.9476
0.9644
1.1454
0.7076
1.3953
0.5628
0.7042
0.6591
0.5150
1.5130
0.3627
0.4111
0.3086
0.3854
0.3307
0.3990
1.1160
0.4831
0.7158
0.6394
0.7017
0.9680
ω
298.15
298.15
293.1
298.15
300.15
298.15
298.15
298.15
353.15
298.15
298.15
298.15
295.15
353.15
353.15
298.15
298.15
298.15
298.15
373.15
298.15
298.15
298.15
298.15
298.15
298.15
T (K)
Fcalc (g/cm3) 1.2499 1.2161 1.2656 1.4488 1.4500 1.1461 1.0581 1.1275 1.2286 1.2208 1.1534 1.1702 1.3770 1.5249 1.4408 1.1204 1.0941 1.2288 1.0751 1.1164 1.2824 1.1565 1.1444 1.1412 1.1642 1.2404
Flit (g/cm3)a 1.211820 1.277015 1.367315 1.483515 1.440020 1.222014 1.128415 1.243736 1.314016 1.328016 1.212416 1.250037 1.310037 1.473020 1.330024 0.997138 1.069016 1.146737 0.970019 1.050019 1.220020 1.093516 1.040020 1.302016 1.240020 1.260020
-1.6
-6.1
-12.4
10.0
5.8
5.1
6.3
10.8
7.2
2.3
12.4
8.3
3.5
5.1
-6.4
-4.9
-8.1
-6.5
-9.3
-6.2
-6.2
0.7
-2.3
-7.4
-4.8
3.1
%∆F
1326 Ind. Eng. Chem. Res., Vol. 47, No. 4, 2008
a
[mommim] [BF4] [bpyr] [BF4] [4MOPY] [BF4] [C23guan] [BF4] [DEME] [BF4] [bmim] [tca] [emim] [SCN] [N-epy] [ta] [emim] [ta] [mpmi] [TfO] [dbim] [TfO] [N8444] [TfO] [Bemim] [TfO] [mbpyr] [TfO] [omim] [TfO] [4MOPY] [TfO] [dmpim] [TMEM] [bmim] [TMEM]
ionic liquid
C12H15F9N2O6S3
C12H15F9N2O6S3
C15H24NO3SF3
C13H23F3N2O3S
C11H16NO3F3
C12H13N2O3SF3
C21H44NF3SO3
C12H21N2F3SO3
C12H13N2F3SO4
C8H11N2F3O2
C9H10F3NO2
C7H11N3S
C9H15N3S
C8H20NOF4B
C23H50N3F4B
C14H24BF4N
C9H14BF4N
C6H11N2OBF4
global formula 214
methyloxymethyl-3-methylidimazolium tetrafluoroborate 1-butylpyridinium tetrafluoroborate 4-methyl-n-octylpyridinium tetrafluoroborate bis-hexyl-amino-methylene dimethylammonium tetrafluoroborate N,N-diethyl-N-methyl-N-(2-methoxyethyl)ammonium tetrafluoroborate 1-butyl-3-methylidimazolium thiocyanate 1-ethyl-3-methylidimazolium thiocyanate 1-ethylpyridinium trifluoroacetate 1-ethyl-3-methylidimazolium trifluoroacetate 1-(4-methoxyphenyl)-3-methylidimazolium trifluoromethane sulfonate 1,3-dibutylimidazolium trifluoromethane sulfonate tributyloctylammonium trifluoromethane sulfonate 1-benzyl-3-methylidimazolium trifluoromethane sulfonate 1-butyl-4-methylpyridinium trifluoromethane sulfonate 1-octyl-3-methylidimazolium trifluoromethane sulfonate 4-methyl-n-octylpyridinium trifluoromethane sulfonate 1,2-dimethyl-3-propylimidazolium tris(trifluoromethylsulfonyl)methide 1-butyl-3-methylimidazolium tris(trifluoromethylsulfonyl)methide 550
550
355
344
299
322
448
330
338
224
221
169
197
233
455
293
223
M
IUPAC name
1034.4
1039.3
788.8
799.2
697.3
803.0
858.2
776.4
830.4
562.8
535.1
717.3
763.1
393.5
803.3
576.3
456.9
471.9
Tb (K)
The reference (noted as a superscript) corresponds to the source from which the literature density value was obtained.
200
199
198
197
196
195
194
193
192
191
190
189
188
187
186
185
184
183
No.
Table 3. (Continued)
1571.4
1568.6
1065.7
1088.7
997.8
1158.0
1066.7
1072.0
1184.7
775.7
739.9
1013.6
1047.4
501.4
975.1
720.8
597.6
623.7
TC (K)
24.0
23.9
20.1
21.6
26.9
29.0
12.6
23.2
28.0
24.2
24.2
22.3
19.4
17.1
9.2
15.1
20.3
23.3
PC (bar)
1213.6
1212.0
1027.8
979.1
799.3
813.7
1458.4
922.0
827.7
610.4
586.5
666.4
780.7
693.1
1603.5
932.1
648.1
556.4
VC (cm3/mol)
0.1320
0.1526
0.5898
0.5766
0.4153
0.4118
0.9461
0.5325
0.4481
0.5664
0.5483
0.3931
0.4781
0.9465
0.9385
1.0289
0.8307
0.8291
ω
297.65
298.15
298.15
298.15
298.15
303.15
293.15
303.15
323.15
298.15
293.1
298.15
298.15
293.15
298.15
298.15
298.20
298.15
T (K)
Fcalc (g/cm3) 1.2599 1.1174 1.1237 1.1050 1.0539 0.8738 0.8573 1.2409 1.2180 1.3778 1.2295 1.1737 1.3313 1.2441 1.2248 1.2079 1.5007 1.4913
Flit (g/cm3)a 1.330020 1.214439 1.080017 0.970020 1.180029 1.069615 1.114015 1.273016 1.390016 1.320020 1.300020 1.020020 1.300040 1.170024 1.120024 1.170017 1.597012 1.563027
-4.6
-6.0
3.2
9.4
6.3
2.4
15.1
-5.4
4.4
-12.4
-2.5
-19.0
-18.3
-10.7
13.9
4.0
-8.0
-5.3
%∆F
Ind. Eng. Chem. Res., Vol. 47, No. 4, 2008 1327
1328
Ind. Eng. Chem. Res., Vol. 47, No. 4, 2008
Table 4. Average, Absolute and Maximum Deviations Found between Predicted and Experimental Densities for the 200 Ionic Liquids
a
parameter
value
number of ionic liquids with %∆F > 10% number of ionic liquids with %∆F < 10% number of ionic liquids with %∆F
