Names and abbreviations of ionic liquids.
Abstract
In this work, a new group contribution method was used for calculating gas-to-ionic liquid partition coefficients (log KL) of molecular solutes in ILs with a temperature-dependent linear solvation energy relationship. About 36 group parameters are used to correlate 14,762 log KL data points of organic compounds in ionic liquids. The experimental log KL data have been collected from the published literature for different solutes in ionic liquids at different temperatures within the range of 293.15–396.35 K. The calculated log KL data showed a satisfactory agreement with experimental data with an average absolute relative deviation (AARD) of 6.39%.
Keywords
- inverse gas chromatography
- solvation model
- thermodynamic properties
- ionic liquids
- polarity
1. Introduction
Gas chromatography is a widely used technique for the characterization of complex systems in chemical industries but also for the determination of physicochemical properties of solute in the stationary phase. This approach is also known as inverse gas chromatography (IGC) is used to quantify the solute-stationary interactions or the polarity of the last one. At the end of the twentieth century, numerous solvation models were proposed to represent retention data from chromatography. The most well-known models are called Linear Free Energy Relationship (LFER) or Linear Solvation Energy Relationship (LSER). The most recent representation of the LSER model proposed by Abraham [1, 2, 3, 4] is given by Eq. (1).
Where SP is a solvation parameter related with the free energy change such as gas–liquid partition coefficient, specific retention volume, or adjusted retention time at a given temperature. The capital letters represent the solutes properties and the lowercase letters the complementary properties of the ionic liquids. The solute descriptors are the excess molar refraction
A large databank of experimental LSER parameters for organic compounds can be found in the literature. Platts et al. proposed to determine these parameters using group contribution methods [5, 6].
In order to improve the predictive applicability of the Abraham model for ionic liquids, Sprunger et al. [8, 9, 10, 11] have proposed a method for predicting log
Other approaches reported in the literature to calculate log KL are based on group contribution methods (GC). This method is useful because we need only to know the structure of the material (IL). Revelli et al. [12] proposed to splits the cation with its alkyl chains into 21 different contributions to estimate log
In this chapter, we propose to extend the model temperature-dependent GC-LSER (TDGC-LSER) based on the group contribution method to correlate and analysis of log KL values for different solutes in ILs as a function of the temperature from 293.15 to 396.35 K. A new decomposition but also new groups are proposed in this approach. The database includes the alkyl-based ILs as well as functionalized ILs (task-specific ILs) such as alcohols and ethers. The largest number of ILs used in this database was composed of imidazolium cation-based ILs (73 ILs). Three new cations were included, choline, quinolinium, and octanium, each cation occurs only once in the database as well as Sulphonium-Based ILs.
2. Calculation of gas-liquid partition coefficients from inverse gas chromatography data
Partition coefficients
3. Data sets and methodology
The objective of this study is to extend the potential applicability of the TDGC-LSER model for the prediction of log
No. | Abbreviation | Ionic liquid Name | Reference |
---|---|---|---|
1 | [MMIM]+ [MeSO4]− | 1-metyl-3-methylimidazolium methylsulfate | [14] |
2 | [BMIM]+ [MeSO4]− | 1-butyl-3-methylimidazolium methylsulfate | [15] |
3 | [EMIM]+ [F3AC]− | 1-ethyl-3-methylimidazolium trifluoroacetate | [16] |
4 | [HMIM]+ [F3AC]− | 1-hexyl-3-methylimidazolium trifluoroacetate | [17] |
5 | [EMIM]+ [Tf2N]− | 1-Ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imidate | [18] |
6 | [EMIM]+ [Tf2N]− | 1-Ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)Amide | [18] |
7 | [EMIM]+ [Tf2N]− | 1-Ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide | [19] |
8 | [EMIM]+ [Tf2N]− | 1-Ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imidate | [18] |
9 | [EMIM]+ [Tf2N]− | 1-Ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)Amide | [18] |
10 | [MMIM]+ [Tf2N]− | 1-methyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide | [19] |
11 | [BMIM]+ [Tf2N]− | 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide | [20] |
12 | [BMIM]+ [Tf2N]− | 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide | [19] |
13 | [BMIM]+ [Tf2N]− | 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide | [21] |
14 | [BMIM]+ [Tf2N]− | 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide | [22] |
15 | [MEIM]+ [Tf2N]− | 1-methyl-3-ethylimidazolium bis(trifluoromethylsulfonyl) amide | [23] |
16 | [M2EIM]+ [Tf2N]− | 1,2-dimethyl-3-ethylimidazolium bis(trifluoromethylsulfonyl) amide | [23] |
17 | [HMIM]+ [Tf2N]− | 1-hexyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide | [20] |
18 | [HMIM]+ [Tf2N]− | 1-hexyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide | [24] |
19 | [HMIM]+ [Tf2N]− | 1-hexyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide | [25] |
20 | [OMIM]+ [Tf2N]− | 1-octyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide | [25] |
21 | [OMIM]+ [Tf2N]− | 1-octyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide | [22] |
22 | [(CH2)4SO3HMIM]+ [Tf2N]− | 1-(4-sulfobutyl)-3-methylimidazolium bis(trifluoromethanesulfonyl)imide | [26] |
23 | [EtOHMIM]+ [Tf2N]− | 1-ethanol-3-methylimidazolium bis(trifluoromethylsulfonyl)imide | [27] |
24 | [MeoeMIM]+ [Tf2N]− | 1-(methylethylether)-3-methylimidazolium bis(trifluoromethylsulfonyl)imide | [27] |
25 | [(MeO)2IM]+ [Tf2N]− | 1,3-dimethoxyimidazolium bis(trifluoromethylsulfonyl)imide | [27] |
26 | [(CH2)4SO3HMIm]+ [TFO]− | 1-(4-sulfobutyl)-3-methylimidazolium trifluoromethanesulfonate | [26] |
27 | [(CH2)4SO3HMIm]+ [HSO4]− | 1-(4-sulfobutyl)-3-methylimidazolium hydrogen sulfate | [26] |
28 | [BMIM]+ [TDI]− | 1-butyl-3-methylimidazolium 4,5-dicyano-2 (trifluoromethyl)imidazolide | [28] |
29 | [C2OHMIM]+ [FAP]− | 1-(2-hydroxyethyl)-3-methylimidazolium tris(pentafluoroethyl)trifluorophosphate | [29] |
30 | [C2OHMIM]+ [FAP]− | 1-(2-hydroxyethyl)-3-methylimidazolium tris(pentafluoroethyl)trifluorophosphate | [30] |
31 | [EMIM]+ [FAP]− | 1-ethyl-3-methylimidazolium tris(pentafluoroethyl)trifluorophosphate | [31] |
32 | [BMIM]+ [N(CN)3]− | 1-butyl-3-methylimidazolium tricyanomethanide | [32] |
33 | [EMIM]+ [BF4]− | 1-ethyl-3-methylimidazolium tetrafluoroborate | [33] |
34 | [EMIM]+ [BF4]− | 1-ethyl-3-methylimidazolium tetrafluoroborate | [34] |
35 | [BMIM]+ [BF4]− | 1-butyl-3-methylimidazolium tetrafluoroborate | [20] |
36 | [BMIM]+ [BF4]− | 1-butyl-3-methylimidazolium tetrafluoroborate | [33] |
37 | [BMIM]+ [BF4]− | 1-butyl-3-methylimidazolium tetrafluoroborate | [35] |
38 | [BMIM]+ [BF4]− | 1-butyl-3-methylimidazolium tetrafluoroborate | [21] |
39 | [HMIM]+ [BF4]− | 1-hexyl-3-methylimidazolium tetrafluoroborate | [33] |
40 | [HMIM]+ [BF4]− | 1-hexyl-3-methylimidazolium tetrafluoroborate | [36] |
41 | [OMIM][BF4]− | 1-octyl-3-methylimidazolium tetrafluoroborate | [33] |
42 | [OMIM][BF4]− | 1-octyl-3-methylimidazolium tetrafluoroborate | [21] |
43 | [C2OHMIM]+ [BF4]− | 1-(2-hydroxyethyl)-3-methylimidazolium tetrafluoroborate | [37] |
44 | [PM2IM]+ [BF4]− | 1-propyl-2,3-dimethylimidazolium tetrafluoroborate | [38] |
45 | [PM2IM]+ [BF4]− | 1-propyl-2,3-dimethylimidazolium tetrafluoroborate | [39] |
46 | [EMIM]+ [(MeO)(H)PO2]− | 1-ethyl-3-methylimidazolium methylphosphonate | [40] |
47 | [M2MIM]+ [(MeO)(H)PO2]− | 1.3-dimethylimidazolium methylphosphonate | [40] |
48 | [EMIM]+ [EtSO4]− | 1-ethyl-3-methylimidazolium ethylsulfate | [41] |
49 | [EMIM]+ [EtSO4]− | 1-ethyl-3-methylimidazolium ethylsulfate | [19] |
50 | [BMIM]+ [OcSO4]− | 1-butyl-3-methylimidazolium octylsulfate | [20] |
51 | [BMIM]+ [OcSO4]− | 1-butyl-3-methylimidazolium octylsulfate | [42] |
52 | [EMIM]+ [SCN]− | 1-ethyl-3-methyl-imidazolium thiocyanate | [43] |
53 | [EMIM]+ [SCN]− | 1-ethyl-3-methyl-imidazolium thiocyanate | [22] |
54 | [BMIM]+ [SCN]− | 1-butyl-3-methylimidazolium thiocyanate | [44] |
55 | [BMIM]+ [SCN]− | 1-butyl-3-methylimidazolium thiocyanate | [22] |
56 | [HMIM]+ [SCN]− | 1-hexyl-3-methylimidazolium thiocyanate | [45] |
57 | [MMIM]+ [CH3OC2H4SO4]− | 1-methyl-3-methylimidazolium methoxyethylsulfate | [14] |
58 | [MMIM]+ [(CH3)2PO4]− | 1-methyl-3-methylimidazolium dimethylphosphate | [14] |
59 | [BMIM]+ [PF6]− | 1-butyl-3-methylimidazolium hexafluorophosphate | [46] |
60 | [HMIM]+ [PF6]− | 1-hexyl-3-methylimidazolium hexafluorophosphate | [47] |
61 | [HMIM]+ [PF6]− | 1-hexyl-3-methylimidazolium hexafluorophosphate | [47] |
62 | [MOIM]+ [PF6]− | 1-methyl-3-octylimidazolium hexafluorophosphate | [48] |
63 | [EMIM]+ [CF3SO3]− | 1-ethyl-3-methylimidazolium trifluoromethanesulfonate | [49] |
64 | [BMIM]+ [CF3SO3]− | 1-butyl-3-methylimidazolium trifluoromethanesulfonate | [22] |
65 | [HMIM]+ [CF3SO3]− | 1-hexyl-3-methylimidazolium trifluoromethanesulfonate | [50] |
66 | [HMIM]+ [CF3SO3]− | 1-hexyl-3-methylimidazolium trifluoromethanesulfonate | [22] |
67 | [BMIM]+ [NO3]− | 1-Butyl-3-methylimidazolium nitrate | [51] |
68 | [OMIM]+ [NO3]− | 1-octyl-3-methylimidazolium nitrate | [52] |
69 | [B4MPY]+ [N(CN)2]− | 1-butyl-4-methylpyridinium dicyanamide | [53] |
70 | [BMPY]+ [TDI]− | 1-Butyl-3-methylpyridinium 4,5-dicyano-2-(trifluoromethyl)imidazolide | [28] |
71 | [BMPY]+ [N(CN)3]− | 1-butyl-4-methylpyridinium tricyanomethanide | [32] |
72 | [NEPY]+ [Tf2N]− | N-ethylpyridinium bis(trifluoromethylsulfonyl)imide | [14] |
73 | [4MBPY]+ [BF4]− | 4-methyl-N-butylpyridinium tetrafluoroborate | [54] |
74 | [4MBPY]+ [BF4]− | 4-methyl-N-butylpyridinium tetrafluoroborate | [55] |
75 | [4MBPY]+ [BF4]− | 4-methyl-N-butylpyridinium tetrafluoroborate | [46] |
76 | [BMPY]+ [Tf2N]− | 1-butyl-3-methylpyridinium bis(trifluoromethylsulfonyl)imide | [56] |
77 | [1,3BMPY]+ [CF3SO3]− | 1-butyl-3-methylpyridinium trifluoromethanesulfonate | [57] |
78 | [C2PY]+ [Tf2N]− | 2-alkylpyridinium bis(trifluoromethylsulfonyl)imide | [22] |
79 | [C4PY]+ [Tf2N]− | 4-alkylpyridinium bis(trifluoromethylsulfonyl)imide | [22] |
80 | [C5PY]+ [Tf2N]− | 5-alkylpyridinium bis(trifluoromethylsulfonyl)imide | [22] |
81 | [BMPYR]+ [N(CN)3]− | 1-butyl-1-methylpyrrolidinium tricyanomethanide | [58] |
82 | [MeoeMPYR]+ [FAP]− | 1-(2-methoxyethyl)-1-methylpyrrolidinium tris(pentafluoroethyl)trifluorophosphate | [59] |
83 | [MeoeMPYR]+ [FAP]− | 1-(2-methoxyethyl)-1-methylpyrrolidinium tris(pentafluoroethyl)trifluorophosphate | [29] |
84 | [PrMPYR]+ [Tf2N]− | 1-propyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide | [60] |
85 | [BMPYR]+ [Tf2N]− | 1-butyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide | [25] |
86 | [BMPYR]+ [Tf2N]− | 1-butyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide | [60] |
87 | [PeMPYR]+ [Tf2N]− | 1-pentyl-1-methylpyrrolidinium Bis(trifluoromethylsulfonyl)imide | [60] |
88 | [HMPYR]+ [Tf2N]− | 1-hexyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide | [61] |
89 | [OMPYR]+ [Tf2N]− | 1-octyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide | [61] |
90 | [BMPYR]+ [CF3SO3]− | 1-butyl-1-methylpyrrolidinium trifluoromethanesulfonate | [62] |
91 | [C5C1PIP]+ [Tf2N]− | 1-5-alkyl-1-methylpiperidinium bis(trifluoromethylsulfonyl)imide | [63] |
92 | [C6C1PIP]+ [Tf2N]− | 1-6-alkyl-1-methylpiperidinium bis(trifluoromethylsulfonyl)imide | [63] |
93 | [MeoeMPIP]+ [FAP]− | 1-(2-methoxyethyl)-1-methylpiperidinium trifluorotris(perfluoroethyl)phosphate | [64] |
94 | [PMPIP]+ [Tf2N]− | 1-propyl-1-methylpiperidiniumbis(trifluoromethylsulfonyl)imide | [65] |
95 | [H3TdP]+ [L-Lact]− | trihexyl(tetradecyl)phosphonium L-lactate | [66] |
96 | [H3TdP]+ [+CS]− | trihexyl(tetradecyl)phosphonium (1S)-(+)-10-camphorsulfonate | [66] |
97 | [H3TdP]+ [Tf2N]− | Trihexyl(tetradecyl)phosphonium bis(trifluoromethylsulfonyl)imide | [67] |
98 | [H3TdP]+ [Tf2N]− | Trihexyl(tetradecyl)phosphonium bis(trifluoromethylsulfonyl)imide | [25] |
99 | [BMMOR]+ [N(CN)3]− | 1-butyl-1-methylmorpholinium tricyanomethanide | [68] |
100 | [N-C3OHMMOR]+ [Tf2N]− | 4-(3-hydroxypropyl)-4-methylmorpholinium bis(trifluoromethylsulfonyl)amide | [69] |
101 | [Et3S]+ [Tf2N]− | triethylsulphonium bis(trifluoromethylsulfonyl)imide | [70] |
102 | [O3MAM]+ [Tf2N]− | trioctylmethylammonium bis(trifluoromethylsulfonyl)imide | [71] |
103 | [O3MAM]+ [Tf2N]− | trioctylmethylammonium bis(trifluoromethylsulfonyl)imide | [71] |
104 | [M3BAM] + [NTf2]− | trimethyl-butylammonium bis(trifluoromethylsulfonyl)imide | [72] |
105 | [Cho]+ [Tf2N]− | choline bis(trifluoromethylsulfonyl)imide | [73] |
106 | [HiQuin]+ [SCN]− | N-hexylisoquinolinium thiocyanate | [74] |
107 | [HDABCO]+ [Tf2N]− | 1-hexyl-1,4-diaza[2.2.2]bicyclooctanium bis(trifluoromethylsulfonyl)imide | [75] |
The collection of organic solutes includes alkanes, cycloalkanes, alkenes, alkynes, aromatics, alcohols, ethers, aldehydes, ketones, chloroalkanes cyanoalkanes, thiophene, pyridine, water, and other solutes. The values of the five solute descriptors for different organic compounds considered in this work can be found in the literature [1, 2, 3, 4, 5, 6]. The solute descriptors used in the calculations were taken from earlier studies on ILs and cover the range from:
Definition | Group | Definition | Group |
---|---|---|---|
CH3 from alkyl chain | CH3 | Trifluorotris(perfluoroethyl)phosphate | [FAP]─ |
CH2 from alkyl chain | CH2 | Bis(trifluoromethylsulfonyl)imide | [Tf2N]─ |
-O- in alkyl chain | O | Hexafluorophosphate | [PF6]─ |
Hydroxyl in alkyl | OH | Tetrafluoroborate | [BF4]─ |
Sulfonyl hydroxide | SO3H | Methylsulfate | [MeSO4]─ |
N ammonium’s cation | [N]+ | Ethylsulfate | [EtSO4]─ |
S sulfonium’s cation | [S]+ | Octylsulfate | [OcSO4]─ |
1,4-diaza [2] bicyclooctanium | [DABCO]+ | Thiocyanate | [SCN]─ |
Imidazolium cation | [IM]+ | Trifluoromethylsulfonate | [CF3SO3]─ |
Pyridinium cation | [PY]+ | Trifluoroacetate | [F3AC]─ |
Pyrrolidinium cation | [PYR]+ | Methoxyethylsulfate | [CH3OC2H4SO4]─ |
Piperidinium cation | [PIP]+ | 4,5-Dicyano-2-(trifluoromethyl)imidazolium | [TDI]─ |
Phosphonium cation | [P]+ | Methylphosphonate | [(MeO)(H)PO2]─ |
Morpholium cation | [MOR]+ | Hydrogen sulfate | [HSO4]─ |
Quinolinium cation | [Quin]+ | Dimethylphosphate | [(CH3)2PO4]─ |
Choline cation | [Cho]+ | L-lactate | [L-Lact]─ |
Dicyanamide | [N(CN)2]─ | (1S)-(+)-10-Camphorsulfonate | [+CS]─ |
Tricyanomethanide | [N(CN)3]─ | Nitrate | [NO3]─ |
4. Results and discussion
In the present study, the database contains 14,762 experimental data for about 107 ILs at the temperature range of 293.15–396.35 K, the main objective of this study is to extend the predictive applicability of the TDGC-LSER model to a new cation and anion based ILs, that have not been reported previously, as the ILs having cyano-based anions (thiocyanate [SCN]─; dicyanamide, [N(CN)2]─; tricyanomethanide, [C(CN)3]─ and perfluorinated anions (e.g. trifluorotris(perfluoroethyl)phosphate, [FAP]). The model adopted in this work is capable of representing log
The TDGC-LSER model may represent the partition coefficient of solutes in ILs using the Eq. 6:
Where ni is the number of group i present in the ionic liquid. Values of ci, ei, si, ai, bi, and li and their standard errors in parentheses are given in Table 3.
Group | ||||||
---|---|---|---|---|---|---|
CH3 | −82.195 (8.697) | 67.71 (13.14) | 1.38 (15.33) | 133.26 (16.50) | 5.69 (14.63) | 4.18 (2.594) |
CH2 | 11.093 (1.523) | −25.428 (2.319) | −15.933 (2.836) | −14.017 (2.827) | −3.663 (3.065) | 8.57 (0.4577) |
O | −18.818 (6.703) | −9.581 (8.681) | 21.984 (8.577) | −30.93 (11.21) | 21.494 (9.081) | −13.017 (1.732) |
OH | −193 (12.76) | 98.11 (17.90) | 39.42 (20.01) | 168.51 (22.02) | 293.86 (19.65) | −17.394 (3.687) |
[N]+ | 2316.75 (64.96) | 353.55 (90.42) | −297.80 (112.6) | −387.6 (120.5) | 98.1 (123.9) | −263.57 (17.99) |
[S]+ | 1892.89 (47.02) | −69.03 (61.36) | 71.74 (73.65) | −358.17 (80.73) | 190.98 (67.59) | −59.51 (11.93) |
SO3H | −401.01 (27.18) | 211.14 (25.90) | 29.56 (29.25) | 963.61 (46.37) | 646.47 (35.68) | −0.109 (5.620) |
DABCO | 1804.97 (41.71) | 116.87 (41.93) | −89.01 (46.46) | −141.72 (70.03) | 232.09 (53.11) | −60.643 (9.825) |
[IM]+ | 1929.34 (39.51) | −29.8 (39.59) | −8.73 (44.00) | −267.56 (65.70) | 180.46 (47.66) | −63.12 (9.213) |
[PY]+ | 1899.81 (39.00) | 8.09 (39.56) | −20.39 (44.43) | −254.68 (65.27) | 189.68 (47.58) | −59.425 (9.001) |
[PYR]+ | 1891.63 (40.38) | −5.33 (40.98) | 16.51 (45.52) | −222.69 (67.02) | 117.9 (49.23) | −50.992 (9.509) |
[PIP]+ | 1896.55 (40.90) | 6.56 (42.01) | 30.75 (46.89) | −231.35 (67.60) | 65.98 (50.61) | −46.801 (9.668) |
[P]+ | 1942.67 (72.12) | 410.56 (98.99) | 48.1 (116.4) | −402.1 (128.0) | 191.7 (122.5) | −243.72 (20.34) |
[MOR]+ | 1834.41 (41.57) | 44.92 (42.28) | 107.86 (46.83) | −119.24 (68.33) | 88.14 (50.55) | −72.741 (9.943) |
[Quin]+ | 1849.71 (40.76) | 25.7 (42.69) | 33.16 (48.08) | −145.85 (66.40) | 33.22 (49.85) | −46.729 (9.584) |
[Cho]+ | −183.29 (35.99) | −522.76 (58.38) | 333.14 (78.77) | −30.32 (75.04) | −49.82 (93.81) | 185.55 (10.51) |
[N(CN)2]─ | −970.82 (36.63) | 150.74 (33.05) | 810.89 (35.05) | 1249.76 (61.39) | −81.18 (40.34) | 197.042 (8.294) |
[N(CN)3] ─ | −896.18 (34.95) | 82.95 (28.43) | 725.96 (29.59) | 894.88 (56.33) | 13.96 (36.19) | 199.506 (7.598) |
[FAP] ─ | −830.7 (34.70) | −74.84 (29.00) | 736.99 (30.24) | 372.32 (56.58) | 52.4 (36.71) | 214.343 (7.509) |
[Tf2N] ─ | −899.66 (33.67) | −29.2 (27.04) | 734.55 (28.17) | 640.99 (55.10) | −10.5 (34.81) | 207.618 (7.095) |
[PF6]─ | −977.77 (36.33) | 85.23 (38.82) | 758.26 (47.71) | 528.15 (64.97) | 125.04 (49.75) | 208.42 (8.180) |
[BF4]─ | −958.9 (34.01) | 144.71 (27.81) | 733.41 (29.17) | 979.13 (56.03) | −40.58 (35.85) | 187.379 (7.214) |
[MeSO4]─ | −912.02 (38.32) | 179.36 (34.98) | 439.56 (38.88) | 1866.13 (72.09) | 112.7 (49.26) | 147.143 (9.112) |
[EtSO4]─ | −959.72 (36.50) | −12.58 (35.09) | 792.73 (39.00) | 1467.31 (65.24) | −194.98 (48.93) | 198.684 (7.880) |
[OcSO4] ─ | −883.39 (45.40) | −65.96 (41.05) | 575.78 (42.09) | 1395.39 (73.88) | −231.21 (50.54) | 249.11 (11.64) |
[SCN]─ | −1120.06 (34.61) | 239.28 (32.03) | 720.87 (36.59) | 1388.16 (56.41) | 64.13 (38.49) | 210.298 (7.459) |
[CF3SO3] ─ | −971.54 (34.72) | 84.5 (30.51) | 708.98 (34.13) | 1048.13 (57.45) | 35.85 (39.56) | 205.302 (7.504) |
[F3AC]─ | −948.31 (36.54) | 192.18 (32.62) | 516.67 (34.42) | 1654.6 (60.42) | −41.21 (40.15) | 201.913 (8.340) |
[CH3OC2H4SO4]─ | −864.62 (60.40) | −117.89 (90.33) | 1150.9 (142.0) | −190.7 (776.4) | −563.9 (186.0) | 128.97 (19.99) |
[TDI]─ | −900.02 (34.69) | 8.82 (28.82) | 719.91 (29.78) | 868.4 (56.35) | −50.29 (36.22) | 228.757 (7.537) |
[(MeO)(H)PO2]─ | −837.19 (39.44) | −110.29 (34.18) | 772.28 (36.82) | 1843.42 (68.33) | −103.52 (42.76) | 175.47 (8.406) |
[HSO4]─ | −718.34 (91.93) | −438.37 (52.51) | 991.64 (66.58) | −457.3 (283.4) | −1113.4 (101.0) | 171.09 (16.10) |
[(CH3)2PO4]─ | −1189.85 (64.54) | 327.11 (52.20) | 379.11 (68.71) | 1887.4 (79.33) | 445.78 (81.67) | 242.14 (17.61) |
[L-Lact] ─ | −935.34 (46.66) | −35.01 (45.39) | 869.85 (46.65) | 2176.62 (89.53) | −254.38 (59.97) | 227.99 (11.50) |
[+CS]─ | −1008.33 (44.06) | −29.46 (43.56) | 822.58 (43.45) | 1674.07 (74.84) | −160.92 (51.68) | 228.68 (10.48) |
[NO3]─ | −937.17 (33.75) | 215.29 (26.72) | 565.62 (29.28) | 1483.74 (45.69) | 125.91 (29.89) | 188.276 (7.003) |
The experimental log KL data for all ILs were reproduced using Eq. (6) with average absolute deviation (AARD) at the level of 6.39%. The model developed is statistically good, and describes the experimental log
The average absolute deviation AARD
The AARD values on the prediction of log
Ionic liquids | Log KL (%) | Ionic liquids | Log KL (%) | ||
---|---|---|---|---|---|
[MMIM]+ [MeSO4]− | 22.82 | 56.93 | [EMIM]+ [EtSO4]− | 6.71 | 21.63 |
[BMIM]+ [MeSO4]− | 13.17 | 27.03 | 10.20 | 19.59 | |
[EMIM]+ [F3AC]− | 5.91 | 15.16 | [BMIM]+ [OcSO4]− | 6.70 | 33.60 |
[HMIM]+ [F3AC]− | 4.54 | 32.12 | 2.78 | 14.49 | |
[MMIM]+ [Tf2N]− | 6.56 | 26.59 | [MMIM]+ [CH3OC2H4SO4]− | 13.82 | 11.28 |
[EMIM]+ [Tf2N]− | 13.55 | 98.45 | [MMIM]+ [(CH3)2PO4]− | 10.73 | 29.15 |
9.36 | 54.05 | [EMIM]+ [CF3SO3]− | 3.24 | 11.55 | |
5.38 | 29.87 | [BMIM]+ [CF3SO3]− | 3.38 | 11.03 | |
13.69 | 101.29 | [HMIM]+ [CF3SO3]− | 10.11 | 23.18 | |
10.64 | 64.23 | 6.93 | 21.79 | ||
[MEIM]+ [Tf2N]− | 6.10 | 17.00 | [BMIM]+ [NO3]− | 6.31 | 29.82 |
[M2EIM]+ [Tf2N]− | 6.73 | 24.15 | [OMIM]+ [NO3]− | 6.12 | 32.88 |
[BMIM]+ [Tf2N]− | 3.90 | 22.78 | |||
5.11 | 24.57 | [B4MPY]+ [N(CN)2]− | 4.54 | 12.64 | |
6.99 | 39.58 | [BMPY]+ [TDI]− | 3.35 | 14.75 | |
3.54 | 27.55 | [BMPY]+ [C(CN)3]− | 3.77 | 19.51 | |
[HMIM]+ [Tf2N]− | 3.15 | 21.65 | [BMPY]+ [Tf2N]− | 5.18 | 16.77 |
3.17 | 16.04 | [4MBPY]+ [BF4]− | 3.88 | 21.36 | |
2.90 | 15.23 | 4.82 | 15.22 | ||
2.86 | 20.70 | 2.67 | 16.47 | ||
0.87 | 5.15 | [1,3BMPY]+ [CF3SO3]− | 9.98 | 42.38 | |
[OMIM]+ [Tf2N]− | 3.12 | 11.35 | [NEPY]+ [Tf2N]− | 9.54 | 29.23 |
2.62 | 11.09 | [C2PY]+ [Tf2N]− | 5.37 | 21.46 | |
[(CH2)4SO3HMIm]+ [Tf2N]− | 7.40 | 34.57 | [C4PY]+ [Tf2N]− | 9.63 | 32.88 |
[EtOHmim]+ [Tf2N]− | 7.12 | 26.81 | [C5PY]+ [Tf2N]− | 9.63 | 32.88 |
[(MeO)2IM]+ [Tf2N]− | 8.05 | 21.27 | |||
[MeoeMIM]+ [Tf2N]− | 4.70 | 20.21 | [BMPYR]+ [C(CN)3]− | 3.09 | 11.06 |
[EMIM]+ [BF4]− | 9.64 | 60.61 | [MeoeMPyrr]+ [FAP]− | 4.70 | 18.65 |
11.71 | 38.35 | 5.61 | 29.68 | ||
[PM2IM]+ [BF4]− | 6.18 | 23.63 | [PrMPYR]+ [Tf2N]− | 4.23 | 16.02 |
35.41 | 35.51 | [BMPYR]+ [Tf2N]− | 4,10 | 15.54 | |
[BMIM]+ [BF4]− | 5.15 | 11.76 | [PeMPYR]+ [Tf2N]− | 3.79 | 14.22 |
12.10 | 22.42 | [HMPYR]+ [Tf2N]− | 1.95 | 7.89 | |
4.25 | 21.49 | [OMPYR]+ [Tf2N]− | 3.27 | 12.20 | |
5.32 | 29.16 | [BMPYR]+ [CF3SO3]− | 7.97 | 14.51 | |
5.55 | 28.39 | [BMPYR]+ [Tf2N]− | 4.60 | 22.93 | |
[HMIM]+ [BF4]− | 6,02 | 19.93 | |||
9.63 | 51.73 | [PMPIP]+ [Tf2N]− | 3,19 | 13.44 | |
[OMIM]+ [BF4]− | 3.57 | 14.14 | [C5C1PiP]+ [Tf2N]− | 2.42 | 10.89 |
3.71 | 22.32 | [C6C1PIP]+ [Tf2N]− | 2.47 | 10.12 | |
5.69 | 29.40 | [MeoeMPIP]+ [FAP]− | 3.74 | 15.66 | |
11.37 | 90.97 | ||||
[C2OHMIM]+ [BF4]− | 10.65 | 38,39 | [H3TdP]+ [L-Lact]− | 3.06 | 16.80 |
[BMIM]+ [PF6]− | 2.70 | 18.20 | [H3TdP]+ [+CS]− | 5.90 | 33.28 |
[HMIM]+ [PF6]− | 3.36 | 14.79 | [H3TdP]+ [Tf2N]− | 3.58 | 16.19 |
3.32 | 14.51 | 4.55 | 23.55 | ||
[MOIM]+ [PF6]− | 2.91 | 12.12 | |||
[(CH2)4SO3HMIm]+ [TFO]− | 12.52 | 31.50 | [BMMOR]+ [C(CN)3]− | 5.94 | 13.17 |
[(CH2)4SO3HMIm]+ [HSO4]− | 8.56 | 36.71 | [N-C3OHMMOR]+ [Tf2N]− | 12.42 | 15.87 |
[BMIM]+ [TDI]− | 3.42 | 13.01 | |||
[EMIM]+ [FAP]− | 8.41 | 23.43 | [Et3S]+ [Tf2N]− | 3.63 | 8.95 |
[C2OHMIM]+ [FAP]− | 8.25 | 54.98 | |||
4.71 | 21.68 | [M3BA]+ [Tf2N]− | 11.08 | 91.05 | |
[EMIM]+ [SCN]− | 14.50 | 14.31 | [O3MA]+ [Tf2N]− | 8.61 | 52.55 |
9.17 | 19.02 | [O3MA]+ [Tf2N]− | 8.72 | 50.13 | |
[BMIM]+ [SCN]− | 10.20 | 18.10 | |||
14.21 | 29.36 | [Cho]+ [Tf2N]− | 4.82 | 13.95 | |
[HMIM]+ [SCN]− | 5.44 | 18.68 | |||
[BMIM]+ [C(CN)3]− | 3.14 | 10.86 | [HiQuin]+ [SCN]− | 7.93 | 16.65 |
[EMIM]+ [(MeO)(H)PO2]− | 15.89 | 50.54 | |||
[DIMIM]+ [(MeO)(H)PO2]− | 9.70 | 47.47 | [HDABCO]+ [Tf2N]− | 4.28 | 18.48 |
The values obtained for each ILs vary from 0.87 to 35.41%. Figure 2 shows a plot of calculated log
The ILs with the highest AARD are [MMIM]+ [MeSO4]−, [PM2IM]+ [BF4]−, [BMIM]+ [NO3]−, [OMIM]+ [NO3]−, This may be related to the quality of the experimental data or the number of experimental data.
5. Prediction of partition coefficients of organic compounds in ILs not included in the database using the TDGC-LSER model
The predictive power of TDGC-LSER was evaluated calculating log KL of organic compounds in four ILs not included in the database: 1-butyl-3-methylimidazolium chloride [BMIM]+ [Cl]─ [76], 1-butyl-3-methylimidazolium dimethyl phosphate [BMIM]+ [(CH3)2PO4]─ [76], 1-butyl-3-methylimidazolium dicyanamide [BMIM]+ [N(CN)2]─ [77], 1-Dodecyl-3-methylimidzolium Bis(trifluoromethylsulfonyl)-imide [DoMIM]+ [Tf2N]─ [78]. In the case of [BMIM]+ [Cl]─, 224 experimental log
6. Conclusions
The TDGC-LSER model was used for the prediction of log
The list of groups used for the estimation of calculated log
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Mutelet F, Hassan E-SRE, Stephens TW, Acree WE, Baker GA. Activity coefficients at infinite dilution for organic solutes dissolved in three 1-Alkyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide ionic liquids bearing short linear alkyl side chains of three to five carbons. Journal of Chemical & Engineering Data. 2013; 58 (8):2210-2218. DOI: 10.1021/je4001894 - 61.
Nebig S, Liebert V, Gmehling J. Measurement and prediction of activity coefficients at infinite dilution (γ∞), vapor–liquid equilibria (VLE) and excess enthalpies (HE) of binary systems with 1,1-dialkyl-pyrrolidinium bis(trifluoromethylsulfonyl)imide using mod. UNIFAC (Dortmund). Fluid Phase Equilibria. 2009; 277 (1):61-67. DOI: 10.1016/j.fluid.2008.11.013 - 62.
Domańska U, Redhi GG, Marciniak A. Activity coefficients at infinite dilution measurements for organic solutes and water in the ionic liquid 1-butyl-1-methylpyrrolidinium trifluoromethanesulfonate using GLC. Fluid Phase Equilibria. 2009; 278 (1):97-102. DOI: 10.1016/j.fluid.2009.01.011 - 63.
Paduszyński K, Domańska U. Experimental and theoretical study on infinite dilution activity coefficients of various solutes in piperidinium ionic liquids. The Journal of Chemical Thermodynamics. 2013; 60 :169-178. DOI: 10.1016/j.jct.2013.01.005 - 64.
Marciniak A, Wlazło M. Activity coefficients at infinite dilution and physicochemical properties for organic solutes and water in the ionic liquid 1-(2-methoxyethyl)-1-methylpiperidinium trifluorotris(perfluoroethyl)phosphate. The Journal of Chemical Thermodynamics. 2013; 57 :197-202. DOI: 10.1016/j.jct.2012.08.016 - 65.
Domańska U, Paduszyński K. Measurements of activity coefficients at infinite dilution of organic solutes and water in 1-propyl-1-methylpiperidinium bis{(trifluoromethyl)sulfonyl}imide ionic liquid using g.l.c. The Journal of Chemical Thermodynamics. 2010; 42 (11):1361-1366. DOI: 10.1016/j.jct.2010.05.017 - 66.
Mutelet F, Alonso D, Stephens TW, Acree WE, Baker GA. Infinite dilution activity coefficients of solutes dissolved in two Trihexyl(tetradecyl)phosphonium ionic liquids. Journal of Chemical & Engineering Data. 2014; 59 (6):1877-1885. DOI: 10.1021/je500050p - 67.
Tumba K, Letcher TM, Naidoo P, Ramjugernath D. Activity coefficients at infinite dilution of organic solutes in the ionic liquid trihexyltetradecylphosphonium bis (trifluoromethylsulfonyl) imide using gas–liquid chromatography at T=(313.15, 333.15, 353.15 and 373.15) K. The Journal of Chemical Thermodynamics. 2013; 65 :159-167. DOI: 10.1016/j.jct.2013.05.030 - 68.
Domańska U, Lukoshko EV. Thermodynamics and activity coefficients at infinite dilution for organic solutes and water in the ionic liquid 1-butyl-1-methylmorpholinium tricyanomethanide. The Journal of Chemical Thermodynamics. 2014; 68 :53-59. DOI: 10.1016/j.jct.2013.08.030 - 69.
Wlazło M, Marciniak A, Zawadzki M, Dudkiewicz B. Activity coefficients at infinite dilution and physicochemical properties for organic solutes and water in the ionic liquid 4-(3-hydroxypropyl)-4-methylmorpholinium bis(trifluoromethylsulfonyl)-amide. The Journal of Chemical Thermodynamics. 2015; 86 :154-161. DOI: 10.1016/j.jct.2015.02.024 - 70.
Domańska U, Marciniak A. Activity coefficients at infinite dilution measurements for organic solutes and water in the ionic liquid triethylsulphonium bis(trifluoromethylsulfonyl)imide. The Journal of Chemical Thermodynamics. 2009; 41 (6):754-758. DOI: 10.1016/j.jct.2008.12.005 - 71.
Gwala NV, Deenadayalu N, Tumba K, Ramjugernath D. Activity coefficients at infinite dilution for solutes in the trioctylmethylammonium bis(trifluoromethylsulfonyl)imide ionic liquid using gas–liquid chromatography. The Journal of Chemical Thermodynamics. 2010; 42 (2):256-261. DOI: 10.1016/j.jct.2009.08.012 - 72.
Heintz A, Vasiltsova TV, Safarov J, Bich E, Verevkin SP. Thermodynamic properties of mixtures containing ionic liquids. 9. Activity coefficients at infinite dilution of hydrocarbons, alcohols, esters, and aldehydes in trimethyl-butylammonium bis(trifluoromethylsulfonyl) imide using gas−liquid chromatography and static method. Journal of Chemical & Engineering Data. 2006; 51 (2):648-655. DOI: 10.1021/je050440b - 73.
Domańska U, Papis P, Szydłowski J. Thermodynamics and activity coefficients at infinite dilution for organic solutes, water and diols in the ionic liquid choline bis(trifluoromethylsulfonyl)imide. The Journal of Chemical Thermodynamics. 2014; 77 :63-70. DOI: 10.1016/j.jct.2014.04.024 - 74.
Królikowska M, Karpińska M, Królikowski M. Measurements of activity coefficients at infinite dilution for organic solutes and water in N-hexylisoquinolinium thiocyanate, [HiQuin][SCN] using GLC. The Journal of Chemical Thermodynamics. 2013; 62 :1-7. DOI: 10.1016/j.jct.2013.02.004 - 75.
Marcinkowski Ł, Kloskowski A, Namieśnik J. Measurement of activity coefficients at infinite dilution of organic solutes in the ionic liquid 1-hexyl-1,4-diaza[2.2.2]bicyclooctanium bis(trifluoromethylsulfonyl)imide using gas–liquid chromatography. The Journal of Chemical Thermodynamics. 2014; 71 :84-90. DOI: 10.1016/j.jct.2013.10.026 - 76.
Martins MAR, Coutinho JAP, Pinho SP, Domańska U. Measurements of activity coefficients at infinite dilution of organic solutes and water on polar imidazolium-based ionic liquids. The Journal of Chemical Thermodynamics. 2015; 91 :194-203. DOI: 10.1016/j.jct.2015.07.042 - 77.
Domańska U, Wlazło M, Karpińska M. Activity coefficients at infinite dilution of organic solvents and water in 1-butyl-3-methylimidazolium dicyanamide. A literature review of hexane/hex-1-ene separation. Fluid Phase Equilibria. 2016; 417 :50-61. DOI: 10.1016/j.fluid.2016.02.004 - 78.
Domańska U, Wlazło M. Thermodynamics and limiting activity coefficients measurements for organic solutes and water in the ionic liquid 1-dodecyl-3-methylimidzolium bis(trifluoromethylsulfonyl) imide. The Journal of Chemical Thermodynamics. 2016; 103 :76-85. DOI: 10.1016/j.jct.2016.08.008