离子液体[Mmim][DMP]与DMSO/乙腈二元体系的密度和黏度

doi:10.11949/0438-1157.20191361

摘要/Abstract

摘要：

离子液体因其特殊的内在结构及性能，使得其在纤维素预处理应用过程中展现出良好的效果，其相关体系的物性研究是推进工业化进程的基础必要数据。因此选用甲基咪唑和磷酸三甲酯合成了离子液体1,3-二甲基咪唑磷酸二甲酯([Mmim][DMP])，并测定了[Mmim][DMP] (1) + DMSO (2) 和 [Mmim][DMP] (1) + 乙腈 (2) 两个二元体系，在293.15~323.15 K时，全组成范围内的密度和黏度。计算了体积性质和超额性质数据。通过比较分析二元体系的超额摩尔体积(V ^E)、表观摩尔体积( $V ?$ )、无限稀释表观摩尔体积( $V ? ∞$ )和偏摩尔体积( $V ?$ )数据，以及分子模拟手段讨论了离子液体与溶剂之间的作用形式，包括离子液体与溶剂之间形成的氢键对溶液性质的影响。

关键词: 离子液体, DMSO, 乙腈, 密度, 黏度

Abstract:

Due to its special structure and properties, ionic liquids have shown good results in the application of cellulose pretreatment. Relevant physical property data is indispensable in promoting the industrialization of ionic liquids. In this study, ionic liquid 1, 3-dimethylimidazolium dimethylphosphate ([Mmim][DMP]) was synthesized and the densities and viscosities for the binary systems of [Mmim][DMP] with dimethylsulfoxide (DMSO) or acetonitrile were measured in the temperature range from (293.15 to 323.15) K over the whole concentration. Then volume properties and excess property data was calculated and fitted. Based on the data of apparent molar volume $V ?$ , apparent molar volume at infinite dilution $V ? ∞$ , partial molar volume $V ?$ , excess molar volume V ^E, and molecular simulation results, the influence of the interaction between IL and solvents and hydrogen bonds formed between IL and DMSO (or acetonitrile) were analyzed.

Key words: ionic liquids, DMSO, acetonitrile, density, viscosity

中图分类号:

TQ 021.2

王薪薪, 周清, 张晓春, 张志博, 吕兴梅, 张锁江. 离子液体[Mmim][DMP]与DMSO/乙腈二元体系的密度和黏度[J]. 化工学报, 2020, 71(1): 177-191.

Xinxin WANG, Qing ZHOU, Xiaochun ZHANG, Zhibo ZHANG, Xingmei LYU, Suojiang ZHANG. Densities and viscosities of binary system containing 1,3-dimethylimidazolium dimethylphosphate and dimethyl sulfoxide or acetonitrile[J]. CIESC Journal, 2020, 71(1): 177-191.

图/表 17

表1 纯物质的密度、黏度实验值与文献值比较

Table 1 Comparison of measured with literature values of densities and viscosities of pure compounds

Compound	T/K	ρ/(g·cm^-3)		η/(mPa·s)
Compound	T/K	Exp.	Lit.	Exp.	Lit.
[Mmim][DMP]	298.15	1.261314	1.2587^[43] 1.2612^[41]	290.7599	271.86^[43]
	303.15	1.257795	1.2559^[43] 1.2441^[42]	210.0863	188.30^[43]
	308.15	1.254402	1.2530^[43]	155.5793	139.49^[43]
	313.15	1.250993	1.2491^[43] 1.2505^[41] 1.2368^[42]	119.1838	110.25^[43]
	318.15	1.247590	1.2452^[43]	92.7692	84.44^[43]
	323.15	1.244193	1.2415^[43] 1.2274^[42]	74.2418	69.99^[43]
DMSO	293.15	1.100318	1.10076^[58]	1.9937	2.210^[58]
	298.15	1.095326	1.0958^[59]	1.8027	1.964^[59]
			1.09574^[58]
	303.15	1.090312	1.09073^[58]	1.6362	1.787^[59]
			1.0900^[59]
	308.15	1.085265	1.0839^[59]	1.4961	1.566^[59]
	313.15	1.080264	1.08069^[58]	1.3746	1.490^[59]
			1.0783^[59]
	318.15	1.075234	1.0731^[59]	1.2682	1.3173^[62]
	323.15	1.070217	1.07066^[58]	1.1756	1.285^[59]
			1.0693^[59]
乙腈	293.15	0.782374	0.7820^[60]	0.3548	0.3645^[60]
	298.15	0.776984	0.7760^[61]	0.3440	0.344^[61]
	303.15	0.771554	0.7712^[60]	0.3323	0.3307^[60]
	308.15	0.766094	0.7663^[61]	0.3220	0.313^[61]
	313.15	0.760602	0.7603^[60]	0.3124	0.3005^[60]
	318.15	0.755076	0.7550^[61]	0.3037	0.289^[61]
	323.15	0.749510	0.7492^[60]	0.2956	0.2746^[60]

表2 方程(1)拟合参数A和B的值

Table 2 Fitted values of empirical parameters A and B for densities of binary mixtures based on Eq. (1)

x ₁	A/(g·cm^-3)	B×10^-4/(g·cm^-3·K^-1)	R ²
[Mmim][DMP] (1) + DMSO (2)
0	1.394	-10.000	1
0.1002	1.412	-9.248	1
0.1997	1.426	-8.732	1
0.2998	1.436	-8.333	0.99999
0.4000	1.447	-8.124	0.99988
0.5008	1.450	-7.746	0.99999
0.6023	1.456	-7.553	0.99995
0.7014	1.458	-7.324	0.99999
0.7996	1.460	-7.127	1
0.8964	1.463	-6.984	0.99997
1.0000	1.466	-6.879	0.9999
[Mmim][DMP] (1) + 乙腈 (2)
0	1.103	-11.000	0.99997
0.0901	1.203	-9.771	0.99998
0.2010	1.285	-8.998	0.99976
0.3001	1.329	-8.316	1
0.4013	1.365	-7.940	0.99998
0.5005	1.396	-7.792	0.99994
0.5984	1.414	-7.487	0.99999
0.6978	1.430	-7.270	1
0.8007	1.444	-7.097	0.99999
0.8995	1.462	-7.184	0.99993
1.0000	1.466	-6.879	0.9999

图1 离子液体[Mmim][DMP]的合成

Fig.1 Synthesis of [Mmim][DMP]

图2 [Mmim][DMP]二元体系的密度随温度的变化

Fig.2 Densities for [Mmim][DMP] binary systems as a function of temperature at different mole fractions of IL ■ x 1 = 0; □ x 1 = 0.1002; ▲ x 1 = 0.1997; △ x 1 = 0.2998; ▼ x 1 = 0.4000; ▽ x 1 = 0.5008; ◆ x 1 = 0.6023; ◇ x 1 = 0.7014; ● x 1 = 0.7996; ○ x 1 = 0.8964; × x 1 = 1.0000

图3 [Mmim][DMP]二元体系的密度随组成的变化

Fig.3 Densities for [Mmim][DMP] binary system as a function of mole fractions of IL at different temperatures ■ 293.15 K; □ 298.15 K; ▲ 303.15 K; △ 308.15 K; ▼ 313.15 K; ▽ 318.15 K; ◆ 323.15 K

图4 不同温度下[Mmim][DMP]二元体系的表观摩尔体积随组成和温度的变化

Fig.4 Apparent molar volume versus mole fractions and temperatures of [Mmim][DMP] binary system

表3 293.15~323.15 K下[Mmim][DMP]的无限稀释表观摩尔体积( V ? ∞ )

Table 3 Apparent molar volume at infinite dilution ( V ? ∞ ) of [Mmim][DMP] at temperatures from 293.15 to 323.15 K

T/K	$V ? ∞$ /(cm³·mol^-1)	$S V × 106$ /(mol·kg^-1)	$B V × 106 /$ (kg·m^-3)	$σ (V ? ∞)$ /(cm³·mol^-1)
[Mmim][DMP] (1) + DMSO (2)
293.15	170.85	39.10	-76.28	0.11
298.15	171.22	40.07	-78.19	0.12
303.15	171.59	41.16	-80.62	0.12
308.15	171.93	42.51	-83.45	0.13
313.15	172.28	43.62	-85.68	0.13
318.15	172.62	44.97	-88.46	0.14
323.15	172.95	46.30	-91.13	0.14
[Mmim][DMP] (1) + 乙腈 (2)
293.15	162.96	85.85	-122.79	0.54
298.15	162.83	89.72	-128.38	0.55
303.15	162.70	93.54	-133.90	0.57
308.15	162.54	97.57	-139.64	0.58
313.15	163.21	75.33	-107.73	0.70
318.15	163.11	78.95	-112.86	0.71
323.15	163.05	82.34	-117.73	0.73

表3 293.15~323.15 K下[Mmim][DMP]的无限稀释表观摩尔体积( V ? ∞ )

Table 3 Apparent molar volume at infinite dilution ( V ? ∞ ) of [Mmim][DMP] at temperatures from 293.15 to 323.15 K

T/K	$V ? ∞$ /(cm³·mol^-1)	$S V × 106$ /(mol·kg^-1)	$B V × 106 /$ (kg·m^-3)	$σ (V ? ∞)$ /(cm³·mol^-1)
[Mmim][DMP] (1) + DMSO (2)
293.15	170.85	39.10	-76.28	0.11
298.15	171.22	40.07	-78.19	0.12
303.15	171.59	41.16	-80.62	0.12
308.15	171.93	42.51	-83.45	0.13
313.15	172.28	43.62	-85.68	0.13
318.15	172.62	44.97	-88.46	0.14
323.15	172.95	46.30	-91.13	0.14
[Mmim][DMP] (1) + 乙腈 (2)
293.15	162.96	85.85	-122.79	0.54
298.15	162.83	89.72	-128.38	0.55
303.15	162.70	93.54	-133.90	0.57
308.15	162.54	97.57	-139.64	0.58
313.15	163.21	75.33	-107.73	0.70
318.15	163.11	78.95	-112.86	0.71
323.15	163.05	82.34	-117.73	0.73

表4 293.15~323.15 K下[Mmim][DMP] (1) + DMSO (2)和[Mmim][DMP] (1) + 乙腈 (2)体系的偏摩尔体积

Table 4 Partial molar volumes( V ? ) of mixtures of [Mmim][DMP] with DMSO and acetonitrile at temperatures from 293.15 to 323.15 K

x ₁	$V 1 ˉ$ /(cm³?mol^-1)							$V 2 ˉ$ /(cm³?mol^-1)
x ₁	293.15 K	298.15 K	303.15 K	308.15 K	313.15 K	318.15 K	323.15 K	293.15 K	298.15 K	303.15 K	308.15 K	313.15 K	318.15 K	323.15 K
[Mmim][DMP] (1) + DMSO (2)
0	201.93	202.85	203.78	204.73	205.68	206.64	207.61	70.63	70.94	71.26	71.58	71.90	72.23	72.55
0.1002	195.17	195.49	196.29	197.09	197.90	198.72	199.55	68.31	68.58	68.86	69.14	69.42	69.71	69.99
0.1997	190.64	190.62	191.34	192.07	192.79	193.52	194.26	66.72	66.97	67.23	67.48	67.74	67.99	68.25
0.2998	187.30	187.08	187.74	188.40	189.07	189.74	190.41	65.58	65.81	66.07	66.30	66.54	66.78	67.02
0.4000	184.77	184.42	185.05	185.70	186.32	186.95	187.58	64.66	64.88	65.08	65.30	65.52	65.74	65.96
0.5008	182.71	182.26	182.85	183.42	184.01	184.60	185.20	63.97	64.18	64.39	64.60	64.81	65.02	65.23
0.6023	181.05	180.55	181.12	181.67	182.23	182.79	183.36	63.41	63.59	63.79	63.99	64.19	64.39	64.59
0.7014	179.69	179.19	179.72	180.24	180.78	181.32	181.86	62.96	63.14	63.32	63.51	63.71	63.90	64.09
0.7996	178.55	178.07	178.57	179.07	179.59	180.11	180.63	62.58	62.77	62.95	63.13	63.31	63.50	63.68
0.8964	177.57	177.12	177.62	178.10	178.60	179.10	179.60	62.17	62.36	62.55	62.72	62.90	63.08	63.26
1.0000	176.65	176.15	176.64	177.12	177.60	178.09	178.57	61.77	61.94	62.12	62.28	62.45	62.62	62.80
[Mmim][DMP] (1) + 乙腈 (2)
0	283.98	285.95	287.96	290.02	292.11	294.25	296.43	51.50	51.81	52.14	52.48	52.82	53.16	53.51
0.0901	243.49	243.74	245.05	246.39	247.74	249.10	250.48	44.40	44.62	44.85	45.07	45.30	45.56	45.81
0.2010	219.19	218.63	219.59	220.55	221.53	222.55	223.61	40.07	40.24	40.41	40.59	40.76	40.93	41.10
0.3001	206.58	205.63	206.43	207.23	208.04	208.85	209.67	37.88	38.02	38.18	38.33	38.48	38.64	38.79
0.4013	198.07	196.96	197.66	198.36	199.07	199.78	200.50	36.38	36.52	36.65	36.79	36.94	37.10	37.25
0.5005	192.11	190.97	191.60	192.23	192.88	193.55	194.22	35.35	35.48	35.61	35.74	35.86	35.98	36.11
0.5984	187.65	186.56	187.16	187.74	188.34	188.93	189.54	34.65	34.76	34.88	35.00	35.12	35.24	35.36
0.6978	184.11	183.17	183.72	184.26	184.82	185.38	185.95	34.06	34.17	34.28	34.39	34.50	34.62	34.74
0.8007	181.12	180.37	180.88	181.40	181.92	182.45	182.99	33.48	33.63	33.74	33.86	33.98	34.11	34.24
0.8995	178.72	178.11	178.64	179.14	179.65	180.17	180.70	33.05	33.14	33.25	33.34	33.44	33.53	33.62
1.0000	176.65	176.15	176.64	177.12	177.60	178.09	178.57	32.45	32.55	32.64	32.72	32.81	32.90	32.99

表4 293.15~323.15 K下[Mmim][DMP] (1) + DMSO (2)和[Mmim][DMP] (1) + 乙腈 (2)体系的偏摩尔体积

Table 4 Partial molar volumes( V ? ) of mixtures of [Mmim][DMP] with DMSO and acetonitrile at temperatures from 293.15 to 323.15 K

x ₁	$V 1 ˉ$ /(cm³?mol^-1)							$V 2 ˉ$ /(cm³?mol^-1)
x ₁	293.15 K	298.15 K	303.15 K	308.15 K	313.15 K	318.15 K	323.15 K	293.15 K	298.15 K	303.15 K	308.15 K	313.15 K	318.15 K	323.15 K
[Mmim][DMP] (1) + DMSO (2)
0	201.93	202.85	203.78	204.73	205.68	206.64	207.61	70.63	70.94	71.26	71.58	71.90	72.23	72.55
0.1002	195.17	195.49	196.29	197.09	197.90	198.72	199.55	68.31	68.58	68.86	69.14	69.42	69.71	69.99
0.1997	190.64	190.62	191.34	192.07	192.79	193.52	194.26	66.72	66.97	67.23	67.48	67.74	67.99	68.25
0.2998	187.30	187.08	187.74	188.40	189.07	189.74	190.41	65.58	65.81	66.07	66.30	66.54	66.78	67.02
0.4000	184.77	184.42	185.05	185.70	186.32	186.95	187.58	64.66	64.88	65.08	65.30	65.52	65.74	65.96
0.5008	182.71	182.26	182.85	183.42	184.01	184.60	185.20	63.97	64.18	64.39	64.60	64.81	65.02	65.23
0.6023	181.05	180.55	181.12	181.67	182.23	182.79	183.36	63.41	63.59	63.79	63.99	64.19	64.39	64.59
0.7014	179.69	179.19	179.72	180.24	180.78	181.32	181.86	62.96	63.14	63.32	63.51	63.71	63.90	64.09
0.7996	178.55	178.07	178.57	179.07	179.59	180.11	180.63	62.58	62.77	62.95	63.13	63.31	63.50	63.68
0.8964	177.57	177.12	177.62	178.10	178.60	179.10	179.60	62.17	62.36	62.55	62.72	62.90	63.08	63.26
1.0000	176.65	176.15	176.64	177.12	177.60	178.09	178.57	61.77	61.94	62.12	62.28	62.45	62.62	62.80
[Mmim][DMP] (1) + 乙腈 (2)
0	283.98	285.95	287.96	290.02	292.11	294.25	296.43	51.50	51.81	52.14	52.48	52.82	53.16	53.51
0.0901	243.49	243.74	245.05	246.39	247.74	249.10	250.48	44.40	44.62	44.85	45.07	45.30	45.56	45.81
0.2010	219.19	218.63	219.59	220.55	221.53	222.55	223.61	40.07	40.24	40.41	40.59	40.76	40.93	41.10
0.3001	206.58	205.63	206.43	207.23	208.04	208.85	209.67	37.88	38.02	38.18	38.33	38.48	38.64	38.79
0.4013	198.07	196.96	197.66	198.36	199.07	199.78	200.50	36.38	36.52	36.65	36.79	36.94	37.10	37.25
0.5005	192.11	190.97	191.60	192.23	192.88	193.55	194.22	35.35	35.48	35.61	35.74	35.86	35.98	36.11
0.5984	187.65	186.56	187.16	187.74	188.34	188.93	189.54	34.65	34.76	34.88	35.00	35.12	35.24	35.36
0.6978	184.11	183.17	183.72	184.26	184.82	185.38	185.95	34.06	34.17	34.28	34.39	34.50	34.62	34.74
0.8007	181.12	180.37	180.88	181.40	181.92	182.45	182.99	33.48	33.63	33.74	33.86	33.98	34.11	34.24
0.8995	178.72	178.11	178.64	179.14	179.65	180.17	180.70	33.05	33.14	33.25	33.34	33.44	33.53	33.62
1.0000	176.65	176.15	176.64	177.12	177.60	178.09	178.57	32.45	32.55	32.64	32.72	32.81	32.90	32.99

表5 VFT方程拟合参数A，B和T 0的值

Table 5 Fitted values of empirical parameters, A, B and T 0 for viscosity based on VFT equation

x ₁	A/(mPa·s)	B/K	T ₀/K	R ²
[Mmim][DMP] (1) + DMSO (2)
0	0.074	518.8	135.9	0.99999
0.1002	0.102	521.2	154.7	1.00000
0.1997	0.132	589.7	157.4	0.99992
0.2998	0.246	477.2	183.1	0.99999
0.4000	0.024	1264.1	115.9	0.99970
0.5008	0.324	514.3	192.9	1.00000
0.6023	0.336	536.0	196.6	1.00000
0.7014	0.294	594.8	195.7	1.00000
0.7996	0.418	579.2	200.0	0.99994
0.8964	0.031	1295.5	150.8	0.99971
1.0000	0.287	701.9	196.7	0.99999
[Mmim][DMP] (1) + 乙腈 (2)
0	0.069	386.2	56.85	0.99963
0.0901	0.080	419.7	123.3	0.99999
0.2010	0.043	889.3	79.73	0.99992
0.3001	0.032	1055.9	94.83	0.99484
0.4013	0.223	515.1	172.1	0.99999
0.5005	0.032	1229.1	111.9	0.99860
0.5984	0.192	633.3	180.1	0.99998
0.6978	0.341	547.0	195.7	1.00000
0.8007	0.064	1134.4	144.4	0.99878
0.8995	0.038	1240.9	152.1	0.99971
1.0000	0.287	701.9	196.7	0.99999

图5 [Mmim][DMP]二元体系黏度在不同组成下随温度的变化

Fig.5 Viscosity for [Mmim][DMP] binary system as a function of temperature at different mole fractions of IL（The composition x 1 was the mole fraction of [Mmim][DMP] in DMSO and acetonitrile, respectively） ■ x 1 = 0; □ x 1 = 0.1002; ▲ x 1 = 0.1997; △ x 1 = 0.2998; ▼ x 1 = 0.4000; ▽ x 1 = 0.5008; ◆ x 1 = 0.6023; ◇ x 1 = 0.7014; ● x 1 = 0.7996; ○ x 1 = 0.8964; × x 1 = 1.0000

图6 [Mmim][DMP]二元体系的黏度不同温度下随组成的变化

Fig.6 Viscosity for [Mmim][DMP] (1) + DMSO binary system as a function of mole fractions of IL at different temperatures ■ 293.15 K; □ 298.15 K; ▲ 303.15 K; △ 308.15 K; ▼ 313.15 K; ▽ 318.15 K; ◆ 323.15 K

图7 B3LYP/ 6-311++G**基组优化的[Mmim]阳离子与乙腈和DMSO的结构

Fig.7 Optimized structures of [Mmim]-acetonitrile and [Mmim]-DMSO obtained at the B3LYP/6-311++G**level (Hydrogen bonds are indicated by dotted lines, and distances are in angstroms)

图8 B3LYP/ 6-311++G**基组优化的[DMP]阴离子与乙腈和DMSO的结构

Fig.8 Optimized structures of [DMP]- acetonitrile and [DMP]- DMSO obtained at B3LYP/6-311++G**level(Hydrogen bonds are indicated by dotted lines, and distances are in angstroms)

图9 B3LYP/ 6-311++G**基组优化的[Mmim][DMP]与乙腈和DMSO的结构

Fig.9 Optimized structures of [Mmim][DMP]-acetonitrile and [Mmim][DMP]-DMSO obtained at the B3LYP/6-311++G**level(Hydrogen bonds are indicated by dotted lines, and distances are in angstroms)

表6 二元混合体系V E和Δη 的回归系数及标准偏差

Table 6 Coefficients of standard deviation and Redlich-Kister equation for V E and Δη for two mixtures of [Mmim][DMP] with DMSO and acetonitrile

T / K	V ^E/(cm³·mol^-1)					Δη/(mPa·s)
T / K	A ₀	A ₁	A ₂	A ₃	σ(Y)	A ₀	A ₁	A ₂	A ₃	σ(Y)
[Mmim][DMP] + DMSO
293.15	-2.171	1.142	-0.532	1.704	0.005	-605.0	-214.1	-193.0	-277.3	6.098
298.15	-2.236	1.111	-0.601	1.793	0.007	-412.8	-157.9	-56.80	-61.20	3.020
303.15	-2.262	1.098	-0.807	1.752	0.011	-287.2	-107.1	-24.24	-17.72	1.937
308.15	-2.293	1.155	-0.860	1.792	0.011	-203.3	-69.46	-10.52	-6.481	1.499
313.15	-2.336	1.191	-0.889	1.840	0.011	-149.2	-46.55	-6.010	-4.752	1.255
318.15	-2.381	1.229	-0.947	1.894	0.012	-110.8	-30.66	0.984	1.179	1.116
323.15	-2.436	1.289	-0.988	1.904	0.013	-85.25	-22.46	4.856	7.009	0.897
[Mmim][DMP] + 乙腈
293.15	-5.157	3.292	-2.771	3.492	0.032	-720.3	-514.3	-291.2	-72.87	3.540
298.15	-5.400	3.269	-2.798	4.162	0.030	-499.1	-371.5	-114.9	93.96	4.418
303.15	-5.630	3.372	-2.961	4.368	0.030	-350.8	-246.0	-58.80	78.62	2.564
308.15	-5.837	3.527	-3.051	4.620	0.029	-253.2	-165.1	-17.75	74.31	1.552
313.15	-6.059	3.673	-3.169	4.931	0.028	-189.2	-121.2	-7.246	64.44	1.295
318.15	-6.279	3.712	-3.261	5.477	0.034	-143.9	-93.14	4.74	67.30	1.258
323.15	-6.529	3.778	-3.255	6.099	0.040	-112.4	-72.45	6.374	58.34	1.098

图10 [Mmim][DMP]二元体系的超额摩尔体积不同温度下随组成的变化

Fig.10 Excess molar volumes for mixtures of [Mmim][DMP] binary system as a function of mole fractions of IL at different temperatures(The solid curves are calculated with Redlich-Kister equation, and symbols represent experimental values) ■ 293.15 K; □ 298.15 K; ▲ 303.15 K; △ 308.15 K; ▼ 313.15 K; ▽ 318.15 K; ◆ 323.15 K

图11 [Mmim][DMP]二元体系的黏度偏差不同温度下随组成的变化

Fig.11 Viscosity deviations for mixtures of [Mmim][DMP]binary system at different temperatures(The solid curves are calculated with Redlich-Kister equation, and symbols represent experimental values) ■ 293.15 K; □ 298.15 K; ▲ 303.15 K; △ 308.15 K; ▼ 313.15 K; ▽ 318.15 K; ◆ 323.15 K

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