四种烷基咪唑磷酸酯离子液体的热力学性质

doi:10.16085/j.issn.1000-6613.2023-1722

摘要/Abstract

摘要：

针对烷基咪唑磷酸酯离子液体的热物性数据较少的问题，本文在常压下测定了1-乙基-3-甲基咪唑磷酸二氢盐（[EMIM][DHP]）、1-乙基-3-甲基咪唑磷酸二甲酯盐（[EMIM][DMP]）、1-乙基-3-甲基咪唑磷酸二乙酯盐（[EMIM][DEP]）、1-丁基-3-甲基咪唑磷酸二丁酯盐（[BMIM][DBP]）四种烷基咪唑磷酸酯离子液体的密度、黏度（293.15~353.15K）和电导率（293.15~343.15K），并且测定了四种离子液体的热稳定性。结果表明，离子液体的密度、黏度随温度的升高而减小，而电导率随温度的升高而增大。采用自然对数方程关联四种离子液体的密度，根据实验值计算到了离子液体体积性质；采用VFT方程关联离子液体黏度和电导率，其中密度与电导率的实验值与模型相关系数R²达到0.9999，黏度相关系数R²达到0.99999，实验测定的数据与模型一致；四种离子液体的热稳定性相近，分解温度均在271.9~278.6℃范围内；瓦尔登规则分析表明，四种烷基咪唑磷酸酯离子液体符合Walden规则，而[EMIM][DMP]和[EMIM][DEP]被归类为“good ionic liquids”。

关键词: 烷基咪唑磷酸酯离子液体, 密度, 黏度, 电导率, 热稳定性

Abstract:

The density, viscosity, and conductivity of 1-ethyl-3-methylimidazolium dihydrogen-phosphate ([EMIM][DHP]), 1-ethyl-3-methylimidazolium dimethylphosphate ([EMIM][DMP]), 1-ethyl-3-methylimidazolium diethylphosphate ([EMIM][DEP]) and 1-butyl-3-methylimidazolium dibutyl-phosphate ([BMIM][DBP]) ionic liquids were measured in the temperature range of 293.15K to 353.15K under ambient conditions. Some important volumetric properties, including the isobaric thermal expansion coefficients, molecular volume, standard entropy and lattice potential energy were calculated from the experimental density values. The thermal gravimetric analysis was performed in the temperature range of 35℃ to 700℃, resulting in thermal decomposition temperatures up to 271.9—278.6℃. The Walden rule analysis demonstrated that four phosphate ionic liquids complied with the Walden rule well, while [EMIM][DMP] and [EMIM][DEP] were classified as “good ionic liquids”.

Key words: alkyl imidazolium phosphate ionic liquids, density, viscosity, conductivity, thermal stability

中图分类号:

TQ013.1

刘泽鹏, 曾纪珺, 唐晓博, 赵波, 韩升, 廖袁淏, 张伟. 四种烷基咪唑磷酸酯离子液体的热力学性质[J]. 化工进展, 2024, 43(3): 1484-1491.

LIU Zepeng, ZENG Jijun, TANG Xiaobo, ZHAO Bo, HAN Sheng, LIAO Yuanhao, ZHANG Wei. Thermodynamic properties of four alkyl imidazolium phosphate ionic liquids[J]. Chemical Industry and Engineering Progress, 2024, 43(3): 1484-1491.

图/表 14

表1 实验所用离子液体的生产厂家、纯度和水分

离子液体	简式	生产厂家	纯度（厂家）	水分/μL·L^-1
1-乙基-3-甲基咪唑磷酸二氢盐	[EMIM][DHP]	中国科学院兰州化物所	≥99%	210
1-乙基-3-甲基咪唑磷酸二甲酯盐	[EMIM[DMP]	TCI	≥98%	220
1-乙基-3-甲基咪唑磷酸二乙酯盐	[EMIM][DEP]	TCI	≥98%	240
1-丁基-3-甲基咪唑磷酸二丁酯盐	[BMIM][DBP]	TCI	≥98%	168

表2 四种离子液体在293.15~353.15K范围内的密度

T/K	密度/g·cm^-3
T/K	[EMIM][DHP]	[EMIM][DMP]	[EMIM][DEP]	[BMIM][DBP]
293.15	1.3406	1.2198	1.1485	1.0468
298.15	1.3379	1.2164	1.1450	1.0435
303.15	1.3350	1.2131	1.1416	1.0401
313.15	1.3295	1.2064	1.1349	1.0332
323.15	1.3238	1.1998	1.1283	1.0265
333.15	1.3181	1.1929	1.1215	1.0198
343.15	1.3125	1.1863	1.1149	1.0131
353.15	1.3070	1.1798	1.1083	1.0064
文献值（298.15）	—	1.2161^[21]	1.1442^[25]	1.045^[19]
	—	1.220^[24]	1.145^[20]	1.045^[19]
	—	1.2178^[18]	1.1449^[26]	1.045^[19]

图1 四种离子液体密度随温度变化的实验结果

表3 离子液体密度的自然对数方程拟合参数、相关系数及平均相对误差

离子液体	A/K^-1	ρ₀/g·cm^-3	R²	$Δ ¯$
[EMIM][DHP]	4.24×10^-4	1.5184	0.99996	0.0032%
[EMIM][DMP]	5.56×10^-4	1.4358	0.99998	0.0034%
[EMIM][DEP]	5.92×10^-4	1.3662	0.99998	0.0033%
[BMIM][DBP]	6.57×10^-4	1.2691	0.99998	0.0043%

表3 离子液体密度的自然对数方程拟合参数、相关系数及平均相对误差

离子液体	A/K^-1	ρ₀/g·cm^-3	R²	$Δ ¯$
[EMIM][DHP]	4.24×10^-4	1.5184	0.99996	0.0032%
[EMIM][DMP]	5.56×10^-4	1.4358	0.99998	0.0034%
[EMIM][DEP]	5.92×10^-4	1.3662	0.99998	0.0033%
[BMIM][DBP]	6.57×10^-4	1.2691	0.99998	0.0043%

表4 四种离子液体在298.15K下的分子体积、标准熵及晶格能

离子液体	M/g∙mol^-3	V_m/nm³	S⁰/J∙mol^-1∙K^-1	U_POT/kJ∙mol^-1
[EMIM][DHP]	208.15	0.2584	351.42	472.19
[EMIM][DMP]	236.26	0.3225	431.40	445.93
[EMIM][DEP]	264.26	0.3833	507.06	426.81
[BMIM][DBP]	348.42	0.5545	720.41	389.40

表5 四种烷基咪唑磷酸酯离子液体在293.15~353.15K范围内的黏度

T/K	黏度/mPa·s
T/K	[EMIM][DHP]	[EMIM][DMP]	[EMIM][DEP]	[BMIM][DBP]
293.15	5996.100	353.387	555.920	1829.600
298.15	4014.100	251.860	388.783	1253.267
303.15	2774.167	184.733	279.847	879.270
313.15	1433.633	106.600	156.193	462.327
323.15	808.673	66.478	94.413	262.087
333.15	488.687	44.148	61.017	158.613
343.15	312.090	30.875	41.605	101.400
353.15	208.983	22.512	29.666	67.920
文献值（303.15）	—	192.7^[31]	285.0^[20]	—
	—	186.0^[32]	274.0^[33]	—
	—	194.5^[18]	284.0^[34]	—

图2 离子液体的黏度随温度变化的实验结果

表6 离子液体黏度的VFT方程拟合参数、相关系数及平均相对误差

离子液体	η₀/mPa·s	B/K	T₀	R²	$Δ ¯$
[EMIM][DHP]	0.2500	1219.0	172.28	>0.99999	0.25%
[EMIM][DMP]	0.1380	870.1	182.24	>0.99999	0.03%
[EMIM][DEP]	0.1150	963.3	179.58	>0.99999	0.04%
[BMIM][DBP]	0.0287	1559.6	152.19	>0.99999	0.21%

表6 离子液体黏度的VFT方程拟合参数、相关系数及平均相对误差

离子液体	η₀/mPa·s	B/K	T₀	R²	$Δ ¯$
[EMIM][DHP]	0.2500	1219.0	172.28	>0.99999	0.25%
[EMIM][DMP]	0.1380	870.1	182.24	>0.99999	0.03%
[EMIM][DEP]	0.1150	963.3	179.58	>0.99999	0.04%
[BMIM][DBP]	0.0287	1559.6	152.19	>0.99999	0.21%

表7 四种离子液体在293.15~343.15 K范围内的电导率

T/K	电导率/mS·cm^-1
T/K	[EMIM][DHP]	[EMIM][DMP]	[EMIM][DEP]	[BMIM][DBP]
293.15	0.262	1.161	0.521	0.043
298.15	0.384	1.574	0.742	0.065
303.15	0.556	2.088	1.002	0.090
313.15	1.069	3.437	1.706	0.165
323.15	1.859	5.277	2.681	0.291
333.15	3.005	7.658	4.003	0.468
343.15	4.575	10.63	5.686	0.724

图3 离子液体电导率随温度变化的实验结果

表8 离子液体电导率的VFT方程拟合参数、相关系数及平均相对误差

离子液体	σ₀/mS·cm^-1	C/K	T₀/K	R²	$Δ ¯$
[EMIM][DHP]	2382.9	994.1	184.23	>0.99999	0.34%
[EMIM][DMP]	1617.5	821.5	179.67	>0.99999	0.05%
[EMIM][DEP]	1233.4	880.2	179.54	0.99998	0.57%
[BMIM][DBP]	1550.0	1433.6	156.22	0.99995	1.01%

表8 离子液体电导率的VFT方程拟合参数、相关系数及平均相对误差

离子液体	σ₀/mS·cm^-1	C/K	T₀/K	R²	$Δ ¯$
[EMIM][DHP]	2382.9	994.1	184.23	>0.99999	0.34%
[EMIM][DMP]	1617.5	821.5	179.67	>0.99999	0.05%
[EMIM][DEP]	1233.4	880.2	179.54	0.99998	0.57%
[BMIM][DBP]	1550.0	1433.6	156.22	0.99995	1.01%

图4 四种烷基咪唑磷酸酯离子液体的Walden图

图5 四种烷基咪唑磷酸酯离子液体的热重分析曲线图

表9 四种离子液体的Tstart和Tonset

参数	[EMIM][DHP]	[EMIM][DMP]	[EMIM][DEP]	[BMIM][DBP]
T_start/℃	184.8	198.0	190.9	151.4
T_onset/℃	275.8	278.6	274.5	271.9

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