Physical properties characterizations and NH3 capture performance investigation of novel phenol-based deep eutectic solvents

doi:10.11949/0438-1157.20200796

Abstract

Abstract:

NH₃ pollution has always been a key concern in chemical industry, environmental protection and other fields. The capture and recovery of NH₃ in industrial exhaust gas is of great significance. A novel class of phenol-based deep eutectic solvents (DESs) were constructed by using 1-ethyl-3-methylimidazolium chloride ([Emim]Cl) as the hydrogen bond acceptor, while phenol (Phe), resorcinol (Res) and phloroglucinol (Phl) as the hydrogen bond donors. The densities and viscosities of phenol-based DESs at different temperatures were determined in detail, and the density and viscosity data were correlated by empirical equations. In addition, the NH₃ absorption-desorption performance and absorption selectivity of phenol-based DESs were systematically investigated. It is found that the capacities of phenol-based DESs for NH₃ absorption are quite high, and the absorbed NH₃ can be released by heating and evacuating, with the capacities for NH₃ absorption remaining almost unchanged after several cycles. However, the capacities of phenol-based DESs for CO₂ absorption are quite low, indicating the excellent performance of phenol-based DESs for NH₃/CO₂ selective absorption. Finally, the interaction mechanism of NH₃ absorption in phenol-based DESs was studied in depth with the help of spectral characterizations and quantum chemistry calculations.

Key words: solvents, ammonia, absorption, solubility, thermodynamics

摘要：

NH₃污染问题一直是化工、环保等领域关注的重点问题，对工业尾气中的NH₃进行捕集和回收具有十分重要的意义。以氯化1-乙基-3-甲基咪唑（［Emim］Cl）为氢键受体，苯酚、间苯二酚和间苯三酚为氢键供体，构建了一类新型酚基深共熔溶剂。详细测定了酚基深共熔溶剂在不同温度下的密度和黏度，并采用经验方程对密度和黏度数据进行了关联。此外，系统考察了酚基深共熔溶剂对NH₃的吸收-解吸性能和吸收选择性，发现其具有较高的NH₃吸收容量，被吸收的NH₃可在加热和减压的条件下释放出来，经过多次循环NH₃吸收容量基本保持不变。而酚基深共熔溶剂的CO₂吸收容量则较低，因而具有优异的NH₃/CO₂吸收选择性。最后，借助光谱表征和量子化学计算，深入探究了NH₃在酚基深共熔溶剂中吸收的相互作用机制。

关键词: 溶剂, 氨气, 吸收, 溶解性, 热力学

CLC Number:

TQ 028.8

Ningning CHENG,Lihua ZENG,Yulin DENG,Hailong PENG,Kuan HUANG. Physical properties characterizations and NH₃ capture performance investigation of novel phenol-based deep eutectic solvents[J]. CIESC Journal, 2020, 71(11): 5043-5051.

程宁宁,曾丽花,邓毓麟,彭海龙,黄宽. 新型酚基深共熔溶剂的物性表征及NH₃捕集性能研究[J]. 化工学报, 2020, 71(11): 5043-5051.

Figures/Tables 16

Fig.1 Novel phenol-based DESs

Fig.2 Densities of phenol-based DESs at different temperatures

Fig.3 Viscosities of phenol-based DESs at different temperatures

Table 1 Fitted parameters for Eqs. （2）—（3）

溶剂	a /(g/cm³)	b×10⁴ /(g/(cm³?K))	η₀/(mPa·s)	D/K	T₀/K
[Emim]Cl+苯酚 (1∶1)	1.30369	-6.21786	0.00426	483.8003	253.38626
[Emim]Cl+间苯二酚 (1∶1)	1.35456	-5.8535	9.68005	211.15308	253.79738
[Emim]Cl+间苯三酚 (1∶1)	1.3929	-5.51786	0.0002263	4594.81656	39.92557
[Emim]Cl+间苯三酚 (2∶1)	1.35886	-5.55	0.00226	2757.6287	89.99133
[Emim]Cl+间苯三酚 (3∶1)	1.34481	-5.57143	0.00118	3153.4094	65.12275

Fig.4 Solubilities of NH3 in phenol-based DESs at 313.2 K

Table 2 Solubilities of NH3 in ［Emim］Cl+phenol （1∶1），［Emim］Cl+resorcinol （1∶1），［Emim］Cl+phloroglucinol （1∶1） at 313.2 K

[Emim]Cl+苯酚 (1∶1 )		[Emim]Cl+间苯二酚 (1∶1)		[Emim]Cl+间苯三酚 (1∶1)
$P N H 3$ /kPa	$m N H 3 ?$ /(mol/kg)	$P N H 3$ /kPa	$m N H 3 ?$ /(mol/kg)	$P N H 3$ /kPa	$m N H 3 ?$ /(mol/kg)
2.9	0.11±0.03	2.6	0.29±0.03	2.3	0.55±0.04
12.3	0.28±0.03	12.4	0.81±0.03	12.2	1.00±0.04
25.1	0.58±0.03	25.5	1.19±0.03	26.6	1.48±0.04
52	0.93±0.03	50.8	1.74±0.03	44.5	1.99±0.04
76.9	1.30±0.03	75.8	2.16±0.03	72.2	2.90±0.04
100.7	1.59±0.03	101.4	2.57±0.03	108.2	3.74±0.04
150	2.27±0.03	149.4	3.36±0.03	148.3	4.45±0.04
200.4	2.90±0.03	200.9	4.18±0.03	199	5.38±0.04

Table 2 Solubilities of NH3 in ［Emim］Cl+phenol （1∶1），［Emim］Cl+resorcinol （1∶1），［Emim］Cl+phloroglucinol （1∶1） at 313.2 K

[Emim]Cl+苯酚 (1∶1 )		[Emim]Cl+间苯二酚 (1∶1)		[Emim]Cl+间苯三酚 (1∶1)
$P N H 3$ /kPa	$m N H 3 ?$ /(mol/kg)	$P N H 3$ /kPa	$m N H 3 ?$ /(mol/kg)	$P N H 3$ /kPa	$m N H 3 ?$ /(mol/kg)
2.9	0.11±0.03	2.6	0.29±0.03	2.3	0.55±0.04
12.3	0.28±0.03	12.4	0.81±0.03	12.2	1.00±0.04
25.1	0.58±0.03	25.5	1.19±0.03	26.6	1.48±0.04
52	0.93±0.03	50.8	1.74±0.03	44.5	1.99±0.04
76.9	1.30±0.03	75.8	2.16±0.03	72.2	2.90±0.04
100.7	1.59±0.03	101.4	2.57±0.03	108.2	3.74±0.04
150	2.27±0.03	149.4	3.36±0.03	148.3	4.45±0.04
200.4	2.90±0.03	200.9	4.18±0.03	199	5.38±0.04

Table 3 Solubilities of NH3 in ［Emim］Cl+phloroglucinol DESs with different molar ratios at 313.2 K

[Emim]Cl+间苯三酚 (1∶1)		[Emim]Cl+间苯三酚 (2∶1)		[Emim]Cl+间苯三酚 (3∶1)
$P N H 3$ /kPa	$m N H 3 ?$ /(mol/kg)	$P N H 3$ /kPa	$m N H 3 ?$ /(mol/kg)	$P N H 3$ /kPa	$m N H 3 ?$ /(mol/kg)
2.3	0.55±0.04	6.1	0.34±0.04	4	0.18±0.04
12.2	1.00±0.04	13.5	0.56±0.04	11.4	0.43±0.04
26.6	1.48±0.04	26.8	0.91±0.04	24.9	0.74±0.04
44.5	1.99±0.04	50.4	1.39±0.04	50.7	1.19±0.04
72.2	2.90±0.04	77.2	1.88±0.04	75	1.57±0.04
108.2	3.74±0.04	100.1	2.27±0.05	103.1	1.98±0.04
148.3	4.45±0.04	151.6	3.08±0.05	150.4	2.72±0.04
199	5.38±0.04	199.1	3.83±0.05	200.5	3.43±0.04

Table 3 Solubilities of NH3 in ［Emim］Cl+phloroglucinol DESs with different molar ratios at 313.2 K

[Emim]Cl+间苯三酚 (1∶1)		[Emim]Cl+间苯三酚 (2∶1)		[Emim]Cl+间苯三酚 (3∶1)
$P N H 3$ /kPa	$m N H 3 ?$ /(mol/kg)	$P N H 3$ /kPa	$m N H 3 ?$ /(mol/kg)	$P N H 3$ /kPa	$m N H 3 ?$ /(mol/kg)
2.3	0.55±0.04	6.1	0.34±0.04	4	0.18±0.04
12.2	1.00±0.04	13.5	0.56±0.04	11.4	0.43±0.04
26.6	1.48±0.04	26.8	0.91±0.04	24.9	0.74±0.04
44.5	1.99±0.04	50.4	1.39±0.04	50.7	1.19±0.04
72.2	2.90±0.04	77.2	1.88±0.04	75	1.57±0.04
108.2	3.74±0.04	100.1	2.27±0.05	103.1	1.98±0.04
148.3	4.45±0.04	151.6	3.08±0.05	150.4	2.72±0.04
199	5.38±0.04	199.1	3.83±0.05	200.5	3.43±0.04

Table 4 Comparison with other deep eutectic solvents and ionic liquids for NH3 or CO2 absorption

Entry	Solvent	T/K	$P N H 3$ /kPa	$m N H 3$ /(mol/kg)	$P C O 2$ /kPa	$m C O 2$ /(mol/kg)	NH₃/CO₂选择性	文献
1	[Emim]Cl+间苯三酚 (1∶1)	298.2	100.5	4.983	98.8	0.034	147	本文
2	[Emim]Cl+间苯三酚 (1∶1)	313.2	108.9	3.742	99.5	0.027	139	本文
3	[Emim]Cl+间苯三酚 (1∶1)	333.2	119.6	3.23	100.3	0.019	170	本文
4	[Emim]Cl+间苯三酚 (1∶1)	353.2	92.1	1.9	100.4	0.014	136	本文
5	ChCl+urea(1∶2)	298.2	95	2.213	—	—	—	[27]
6	[Bmim][BF₄]	298.4	128	0.911	—	—	—	[10]
7	[Bmim][PF₆]	298.0	174	1.843	—	—	—	[10]
8	ChCl +EG (1∶2)	313.2	100.5	2.729	—	—	—	[26]
9	ChCl+Res+Gly (1∶3∶5)	313.2	101.3	7.647	100	0.021	369	[28]
10	[bmim][MeSO₃]+urea(1∶1)	313.2	172.6	1.049	—	—	—	[25]
11	[Emim][SCN]	298.2	101.3	2.642	—	—	—	[11]
12	ChCl+PhOH+EG (1∶5∶4)	298.2	101.3	9.619	101.3	0.045	214	[29]
13	[EtOHmim][BF4]	313.2	115.6	3.07	100	0.05	61	[41]
14	[EtOHmim][PF6]	313.2	107.9	2.48	100	0.039	64	[41]

Table 4 Comparison with other deep eutectic solvents and ionic liquids for NH3 or CO2 absorption

Entry	Solvent	T/K	$P N H 3$ /kPa	$m N H 3$ /(mol/kg)	$P C O 2$ /kPa	$m C O 2$ /(mol/kg)	NH₃/CO₂选择性	文献
1	[Emim]Cl+间苯三酚 (1∶1)	298.2	100.5	4.983	98.8	0.034	147	本文
2	[Emim]Cl+间苯三酚 (1∶1)	313.2	108.9	3.742	99.5	0.027	139	本文
3	[Emim]Cl+间苯三酚 (1∶1)	333.2	119.6	3.23	100.3	0.019	170	本文
4	[Emim]Cl+间苯三酚 (1∶1)	353.2	92.1	1.9	100.4	0.014	136	本文
5	ChCl+urea(1∶2)	298.2	95	2.213	—	—	—	[27]
6	[Bmim][BF₄]	298.4	128	0.911	—	—	—	[10]
7	[Bmim][PF₆]	298.0	174	1.843	—	—	—	[10]
8	ChCl +EG (1∶2)	313.2	100.5	2.729	—	—	—	[26]
9	ChCl+Res+Gly (1∶3∶5)	313.2	101.3	7.647	100	0.021	369	[28]
10	[bmim][MeSO₃]+urea(1∶1)	313.2	172.6	1.049	—	—	—	[25]
11	[Emim][SCN]	298.2	101.3	2.642	—	—	—	[11]
12	ChCl+PhOH+EG (1∶5∶4)	298.2	101.3	9.619	101.3	0.045	214	[29]
13	[EtOHmim][BF4]	313.2	115.6	3.07	100	0.05	61	[41]
14	[EtOHmim][PF6]	313.2	107.9	2.48	100	0.039	64	[41]

Fig.5 Solubilities of NH3 in [Emim]Cl+phloroglucinol (1∶1) at different temperatures

Table 5 Solubilities of NH3 in ［Emim］Cl+phloroglucinol （1∶1） at different temperatures

298.2 K		313.2 K		333.2 K		353.2 K
$P N H 3$ /kPa	$m N H 3$ /(mol/kg)	$P N H 3$ /kPa	$m N H 3$ /(mol/kg)	$P N H 3$ /kPa	$m N H 3$ /(mol/kg)	$P N H 3$ /kPa	$m N H 3$ /(mol/kg)
1	0.54±0.08	2.3	0.55±0.04	4.4	0.33±0.05	11.1	0.14±0.03
10.2	1.49±0.08	12.2	1.00±0.04	16.4	0.83±0.05	23.1	0.32±0.03
27.6	2.05±0.08	26.6	1.48±0.04	32.4	1.26±0.05	34.1	0.71±0.03
51.2	3.01±0.08	44.5	1.99±0.04	55.4	1.75±0.05	61.8	1.33±0.03
78.7	4.08±0.08	72.2	2.90±0.04	78.4	2.48±0.05	92.1	1.90±0.03
100.1	4.98±0.08	108.2	3.74±0.04	118.4	3.28±0.05	117.1	2.48±0.03
147.6	6.21±0.08	148.3	4.45±0.04	153.4	4.03±0.05	169.1	3.40±0.03
193.1	7.98±0.08	199	5.38±0.04	210.4	5.00±0.05	219.1	4.17±0.03

Table 5 Solubilities of NH3 in ［Emim］Cl+phloroglucinol （1∶1） at different temperatures

298.2 K		313.2 K		333.2 K		353.2 K
$P N H 3$ /kPa	$m N H 3$ /(mol/kg)	$P N H 3$ /kPa	$m N H 3$ /(mol/kg)	$P N H 3$ /kPa	$m N H 3$ /(mol/kg)	$P N H 3$ /kPa	$m N H 3$ /(mol/kg)
1	0.54±0.08	2.3	0.55±0.04	4.4	0.33±0.05	11.1	0.14±0.03
10.2	1.49±0.08	12.2	1.00±0.04	16.4	0.83±0.05	23.1	0.32±0.03
27.6	2.05±0.08	26.6	1.48±0.04	32.4	1.26±0.05	34.1	0.71±0.03
51.2	3.01±0.08	44.5	1.99±0.04	55.4	1.75±0.05	61.8	1.33±0.03
78.7	4.08±0.08	72.2	2.90±0.04	78.4	2.48±0.05	92.1	1.90±0.03
100.1	4.98±0.08	108.2	3.74±0.04	118.4	3.28±0.05	117.1	2.48±0.03
147.6	6.21±0.08	148.3	4.45±0.04	153.4	4.03±0.05	169.1	3.40±0.03
193.1	7.98±0.08	199	5.38±0.04	210.4	5.00±0.05	219.1	4.17±0.03

Fig.6 Recycling of NH3 absorption in [Emim]Cl+phloroglucinol (1∶1) (absorption condition: 333.2 K, about 100 kPa; desorption condition: 363.2 K, about 0.1 kPa)

Table 6 Solubilities of CO2 in ［Emim］Cl+phloroglucinol （1∶1） at different temperatures

298.2 K		313.2 K		333.2 K		353.2 K
$P C O 2$ /kPa	$m C O 2$ /(mol/kg)	$P C O 2$ /kPa	$m C O 2$ /(mol/kg)	$P C O 2$ /kPa	$m C O 2$ /(mol/kg)	$P C O 2$ /kPa	$m C O 2$ /(mol/kg)
51.4	0.021±0.005	51.4	0.015±0.005	49.8	0.007±0.004	50.1	0.005±0.004
98.8	0.034±0.005	100.7	0.027±0.005	100.3	0.019±0.005	100.4	0.014±0.004
149.5	0.053±0.005	150.7	0.040±0.005	149.2	0.031±0.005	150.3	0.022±0.004
198.7	0.068±0.005	201	0.051±0.005	199.5	0.041±0.005	199.7	0.032±0.004
248.3	0.085±0.005	249.7	0.063±0.005	249.3	0.050±0.005	249.7	0.041±0.004

Table 6 Solubilities of CO2 in ［Emim］Cl+phloroglucinol （1∶1） at different temperatures

298.2 K		313.2 K		333.2 K		353.2 K
$P C O 2$ /kPa	$m C O 2$ /(mol/kg)	$P C O 2$ /kPa	$m C O 2$ /(mol/kg)	$P C O 2$ /kPa	$m C O 2$ /(mol/kg)	$P C O 2$ /kPa	$m C O 2$ /(mol/kg)
51.4	0.021±0.005	51.4	0.015±0.005	49.8	0.007±0.004	50.1	0.005±0.004
98.8	0.034±0.005	100.7	0.027±0.005	100.3	0.019±0.005	100.4	0.014±0.004
149.5	0.053±0.005	150.7	0.040±0.005	149.2	0.031±0.005	150.3	0.022±0.004
198.7	0.068±0.005	201	0.051±0.005	199.5	0.041±0.005	199.7	0.032±0.004
248.3	0.085±0.005	249.7	0.063±0.005	249.3	0.050±0.005	249.7	0.041±0.004

Fig.7

Fig.8 1H NMR spectra of [Emim]Cl+phloroglucinol (1∶1) before and after NH3 absorption

Fig.9 FTIR spectra of [Emim]Cl+phloroglucinol (1∶1) before and after NH3 absorption

Fig.10 Optimized configurations for [Emim]Cl+phloroglucinol and [Emim]Cl+phloroglucinol+NH3 systems

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Physical properties characterizations and NH₃ capture performance investigation of novel phenol-based deep eutectic solvents

新型酚基深共熔溶剂的物性表征及NH₃捕集性能研究

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