Determination of Solubility Parameters of Imidazolyl Acetate Ionic Liquid by Inverse Gas Chromatography and Hansen Solubility Parameters†

doi:10.7503/cjcu20170479

Abstract

Abstract:

The solubility parameters of four imidazolyl acetate ionic liquids were determined by inverse gas chromatography in the range of 353.15—393.15 K. The results show that the solubility parameter values of the four ionic liquids decrease linearly with the increase of temperature in the experimental temperature range. The solubility parameters of the four ionic liquids are 26.14, 24.38, 23.60 and 23.04 MPa^1/2 at 333.15 K by extrapolation method. The solubility parameters of the ionic liquid were also simulated by Hansen solubility parameter software at 333.15 K. The simulation results are 26.52, 23.99, 23.45 and 22.00 MPa^1/2, respectively. The results obtained by the two methods are consistent with each other in the error rang of ±1.05 MPa^1/2, indicating that the two methods are applicable to the determination of the solubility parameters of imidazolyl acetate.

Key words: Ionic liquid, Solubility parameter, Inverse gas chromatography, Hansen’s solubility parameter software;

CLC Number:

O642

TrendMD:

YU Kaile,PAN Xinyu,ZHANG Zhengfang,WANG Qiang. Determination of Solubility Parameters of Imidazolyl Acetate Ionic Liquid by Inverse Gas Chromatography and Hansen Solubility Parameters^†[J]. Chem. J. Chinese Universities, 2018, 39(5): 1048.

Figures/Tables 8

Table 1 Interaction parameter between probes and ILs at different temperatures

Probe	Ionic liquid	$χ 12 ∞$
Probe	Ionic liquid	353.15 K	363.15 K	373.15 K	383.15 K	393.15 K
n-Octane	[EMIM]OAc	3.48	3.40	3.28	3.15	3.05
	[BMIM]OAc	3.95	3.83	3.58	3.45	3.41
	[HMIM]OAc	1.68	1.65	1.61	1.64	1.62
	[OMIM]OAc	2.20	2.15	2.15	2.11	2.09
n-Nonane	[EMIM]OAc	3.51	3.51	3.47	3.41	3.37
	[BMIM]OAc	4.10	4.11	3.88	3.58	3.41
	[HMIM]OAc	2.05	1.66	1.60	1.56	1.61
	[OMIM]OAc	2.23	2.20	2.19	2.15	2.11
n-Decane	[EMIM]OAc	3.52	3.51	3.50	3.48	3.44
	[BMIM]OAc	4.22	4.18	4.01	3.66	3.67
	[HMIM]OAc	1.75	1.70	1.64	1.63	1.57
	[OMIM]OAc	2.28	2.25	2.23	2.19	2.11
n-Undecane	[EMIM]OAc	3.58	3.56	3.53	3.52	3.51
	[BMIM]OAc	4.25	4.26	4.12	3.73	3.82
	[HMIM]OAc	1.80	1.74	1.72	1.69	1.65
	[OMIM]OAc	2.37	2.33	2.30	2.26	2.22
n-Dodecane	[EMIM]OAc	3.67	3.64	3.61	3.58	3.56
	[BMIM]OAc	4.35	4.33	4.27	3.86	3.86
	[HMIM]OAc	1.69	1.84	1.80	1.75	1.73
	[OMIM]OAc	2.47	2.43	2.38	2.34	2.30
Benzene	[EMIM]OAc	0.49	0.49	0.53	0.59	0.65
	[BMIM]OAc	1.36	1.36	1.20	1.25	1.26
	[HMIM]OAc	-0.12	-0.17	-0.27	-0.12	-0.37
	[OMIM]OAc	0.59	0.55	0.56	0.56	0.55
Toluene	[EMIM]OAc	0.84	0.87	0.90	0.93	0.95
	[BMIM]OAc	1.44	1.31	1.23	1.13	1.01
	[HMIM]OAc	0.09	0.06	0.01	-0.09	-0.19
	[OMIM]OAc	0.64	0.66	0.65	0.65	0.62

Table 1 Interaction parameter between probes and ILs at different temperatures

Probe	Ionic liquid	$χ 12 ∞$
Probe	Ionic liquid	353.15 K	363.15 K	373.15 K	383.15 K	393.15 K
n-Octane	[EMIM]OAc	3.48	3.40	3.28	3.15	3.05
	[BMIM]OAc	3.95	3.83	3.58	3.45	3.41
	[HMIM]OAc	1.68	1.65	1.61	1.64	1.62
	[OMIM]OAc	2.20	2.15	2.15	2.11	2.09
n-Nonane	[EMIM]OAc	3.51	3.51	3.47	3.41	3.37
	[BMIM]OAc	4.10	4.11	3.88	3.58	3.41
	[HMIM]OAc	2.05	1.66	1.60	1.56	1.61
	[OMIM]OAc	2.23	2.20	2.19	2.15	2.11
n-Decane	[EMIM]OAc	3.52	3.51	3.50	3.48	3.44
	[BMIM]OAc	4.22	4.18	4.01	3.66	3.67
	[HMIM]OAc	1.75	1.70	1.64	1.63	1.57
	[OMIM]OAc	2.28	2.25	2.23	2.19	2.11
n-Undecane	[EMIM]OAc	3.58	3.56	3.53	3.52	3.51
	[BMIM]OAc	4.25	4.26	4.12	3.73	3.82
	[HMIM]OAc	1.80	1.74	1.72	1.69	1.65
	[OMIM]OAc	2.37	2.33	2.30	2.26	2.22
n-Dodecane	[EMIM]OAc	3.67	3.64	3.61	3.58	3.56
	[BMIM]OAc	4.35	4.33	4.27	3.86	3.86
	[HMIM]OAc	1.69	1.84	1.80	1.75	1.73
	[OMIM]OAc	2.47	2.43	2.38	2.34	2.30
Benzene	[EMIM]OAc	0.49	0.49	0.53	0.59	0.65
	[BMIM]OAc	1.36	1.36	1.20	1.25	1.26
	[HMIM]OAc	-0.12	-0.17	-0.27	-0.12	-0.37
	[OMIM]OAc	0.59	0.55	0.56	0.56	0.55
Toluene	[EMIM]OAc	0.84	0.87	0.90	0.93	0.95
	[BMIM]OAc	1.44	1.31	1.23	1.13	1.01
	[HMIM]OAc	0.09	0.06	0.01	-0.09	-0.19
	[OMIM]OAc	0.64	0.66	0.65	0.65	0.62

Table 1 (Xu) Continued

Probe	Ionic liquid	$χ 12 ∞$
Probe	Ionic liquid	353.15 K	363.15 K	373.15 K	383.15 K	393.15 K
Phenylethane	[EMIM]OAc	1.20	1.23	1.26	1.30	1.30
	[BMIM]OAc	1.92	1.79	1.74	1.71	1.70
	[HMIM]OAc	0.15	0.13	0.10	0.03	-0.05
	[OMIM]OAc	0.80	0.80	0.79	0.77	0.77
Phenylpropane	[EMIM]OAc	1.53	1.54	1.56	1.59	1.59
	[BMIM]OAc	2.16	2.14	1.99	1.94	1.91
	[HMIM]OAc	0.27	0.22	0.20	0.12	0.07
	[OMIM]OAc	0.93	0.91	0.90	0.88	0.87
Cyclohexene	[EMIM]OAc	2.39	2.43	2.37	2.37	2.39
	[BMIM]OAc	3.10	2.91	3.08	2.79	2.69
	[HMIM]OAc	1.23	1.26	1.31	1.41	1.38
	[OMIM]OAc	1.45	1.44	1.42	1.38	1.32
Octene	[EMIM]OAc	3.31	3.35	3.27	3.22	3.25
	[BMIM]OAc	2.84	2.63	2.50	2.34	2.18
	[HMIM]OAc	1.69	1.71	1.84	1.88	1.86
	[OMIM]OAc	1.87	1.90	1.86	1.82	1.81
Methanol	[EMIM]OAc	-2.25	-2.17	-2.15	-2.12	-2.08
	[BMIM]OAc	-0.64	-0.64	-0.64	-0.64	-0.66
	[HMIM]OAc	-1.25	-1.35	-1.27	-1.25	-1.24
	[OMIM]OAc	-0.67	-0.66	-0.65	-0.64	-0.63
Ethanol	[EMIM]OAc	-1.90	-1.85	-1.84	-1.84	-1.81
	[BMIM]OAc	-0.38	-0.39	-0.43	-0.48	-0.51
	[HMIM]OAc	-1.18	-1.22	-1.19	-1.19	-1.19
	[OMIM]OAc	-0.61	-0.62	-0.63	-0.64	-0.65
Propanol	[EMIM]OAc	-1.84	-1.81	-1.80	-1.76	-1.71
	[BMIM]OAc	-0.40	-0.42	-0.44	-0.45	-0.46
	[HMIM]OAc	-1.40	-1.44	-1.39	-1.35	-1.32
	[OMIM]OAc	-0.80	-0.58	-0.79	-0.78	-0.77
Isopropanol	[EMIM]OAc	-1.55	-1.52	-1.51	-1.48	-1.46
	[BMIM]OAc	-0.07	-0.11	-0.15	-0.18	-0.20
	[HMIM]OAc	-1.14	-1.13	-1.14	-1.11	-1.10
	[OMIM]OAc	-0.53	-0.55	-0.56	-0.56	-0.57
Butanol	[EMIM]OAc	-1.70	-1.67	-1.66	-1.63	-1.58
	[BMIM]OAc	-0.30	-0.36	-0.36	-0.39	-0.41
	[HMIM]OAc	-1.15	-1.44	-1.44	-1.40	-1.35
	[OMIM]OAc	-0.85	-0.86	-0.85	-0.85	-0.84

Table 1 (Xu) Continued

Probe	Ionic liquid	$χ 12 ∞$
Probe	Ionic liquid	353.15 K	363.15 K	373.15 K	383.15 K	393.15 K
Phenylethane	[EMIM]OAc	1.20	1.23	1.26	1.30	1.30
	[BMIM]OAc	1.92	1.79	1.74	1.71	1.70
	[HMIM]OAc	0.15	0.13	0.10	0.03	-0.05
	[OMIM]OAc	0.80	0.80	0.79	0.77	0.77
Phenylpropane	[EMIM]OAc	1.53	1.54	1.56	1.59	1.59
	[BMIM]OAc	2.16	2.14	1.99	1.94	1.91
	[HMIM]OAc	0.27	0.22	0.20	0.12	0.07
	[OMIM]OAc	0.93	0.91	0.90	0.88	0.87
Cyclohexene	[EMIM]OAc	2.39	2.43	2.37	2.37	2.39
	[BMIM]OAc	3.10	2.91	3.08	2.79	2.69
	[HMIM]OAc	1.23	1.26	1.31	1.41	1.38
	[OMIM]OAc	1.45	1.44	1.42	1.38	1.32
Octene	[EMIM]OAc	3.31	3.35	3.27	3.22	3.25
	[BMIM]OAc	2.84	2.63	2.50	2.34	2.18
	[HMIM]OAc	1.69	1.71	1.84	1.88	1.86
	[OMIM]OAc	1.87	1.90	1.86	1.82	1.81
Methanol	[EMIM]OAc	-2.25	-2.17	-2.15	-2.12	-2.08
	[BMIM]OAc	-0.64	-0.64	-0.64	-0.64	-0.66
	[HMIM]OAc	-1.25	-1.35	-1.27	-1.25	-1.24
	[OMIM]OAc	-0.67	-0.66	-0.65	-0.64	-0.63
Ethanol	[EMIM]OAc	-1.90	-1.85	-1.84	-1.84	-1.81
	[BMIM]OAc	-0.38	-0.39	-0.43	-0.48	-0.51
	[HMIM]OAc	-1.18	-1.22	-1.19	-1.19	-1.19
	[OMIM]OAc	-0.61	-0.62	-0.63	-0.64	-0.65
Propanol	[EMIM]OAc	-1.84	-1.81	-1.80	-1.76	-1.71
	[BMIM]OAc	-0.40	-0.42	-0.44	-0.45	-0.46
	[HMIM]OAc	-1.40	-1.44	-1.39	-1.35	-1.32
	[OMIM]OAc	-0.80	-0.58	-0.79	-0.78	-0.77
Isopropanol	[EMIM]OAc	-1.55	-1.52	-1.51	-1.48	-1.46
	[BMIM]OAc	-0.07	-0.11	-0.15	-0.18	-0.20
	[HMIM]OAc	-1.14	-1.13	-1.14	-1.11	-1.10
	[OMIM]OAc	-0.53	-0.55	-0.56	-0.56	-0.57
Butanol	[EMIM]OAc	-1.70	-1.67	-1.66	-1.63	-1.58
	[BMIM]OAc	-0.30	-0.36	-0.36	-0.39	-0.41
	[HMIM]OAc	-1.15	-1.44	-1.44	-1.40	-1.35
	[OMIM]OAc	-0.85	-0.86	-0.85	-0.85	-0.84

Fig.1 Relationship between δ12/(RT)-χ12∞/V1 and δ1 at 353.15 K Note:(A) [EMIM]OAc; (B)[BMIM]OAc; (C)[HMIM]OAc; (D)[OMIM]OAc.

Table 2 δ2(MPa1/2) values of four ILs at different temperatures

Ionic liquid	353.15 K	363.15 K	373.15 K	383.15 K	393.15 K	333.15 K	298.15 K
[EMIM]OAc	25.80	25.62	25.46	25.29	25.11	26.14	26.74
[BMIM]OAc	23.79	23.55	23.31	22.93	22.70	24.38	25.36
[HMIM]OAc	23.07	22.99	22.70	22.48	22.18	23.60	24.40
[OMIM]OAc	22.54	22.25	22.06	21.80	21.50	23.04	23.93

Fig.2 Relationship between δ2 and T Note: a. [EMIM]OAc; b. [BMIM]OAc; c. [HMIM]OAc; d. [OMIM]OAc.

Fig.3 Three-dimensional solubility graphs of four ILs Note: (A) [EMIM]OAc; (B)[BMIM]OAc; (C)[HMIM]OAc; (D)[OMIM]OAc.

Table 3 Three-dimensional solubility parameters of four ILs at 333.15 K

Ionic liquid	δ_D/MPa^1/2	δ_P/MPa^1/2	δ_H/MPa^1/2	δ_T/MPa^1/2
[EMIM]OAc	18.80	9.80	15.93	26.52
[BMIM]OAc	17.85	9.60	12.84	23.99
[HMIM]OAc	17.95	8.24	12.65	23.45
[OMIM]OAc	15.42	9.63	12.39	22.00

Table 4 Three-dimensional solubility parameters of four ILs at 298.15 K

Ionic liquid	δ_D/MPa^1/2	δ_P/MPa^1/2	δ_H/MPa^1/2	δ_T/MPa^1/2
[EMIM]OAc	17.03	14.84	14.48	26.83
[BMIM]OAc	15.40	14.29	13.71	25.08
[HMIM]OAc	16.99	10.52	14.23	24.54
[OMIM]OAc	17.77	9.46	13.02	23.98

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