亲水相互作用色谱-静电场轨道阱高分辨质谱法测定CO2吸收液中9种有机胺类化合物

doi:10.3724/SP.J.1123.2022.12014

摘要/Abstract

摘要：

二氧化碳(CO₂)吸收捕集是实现我国碳达峰和碳中和目标的有效措施。有机胺类化合物被广泛用作工业回收CO₂的吸收剂,建立有机胺类化合物的分析检测方法对于碳捕集与封存(CCS)技术和碳捕获、利用与封存(CCUS)技术的发展具有重要意义。本研究建立了以亲水相互作用色谱-静电场轨道阱高分辨质谱法同时测定CO₂吸收液中9种有机胺类化合物的分析方法。样品以水作为溶剂,稀释后经0.22 μm尼龙滤膜过滤后,进样分析。采用Accucore HILIC色谱柱(100 mm×2.1 mm, 2.6 μm),在30 ℃条件下进行分离,流动相A为90%乙腈水溶液(含5 mmol/L甲酸铵和0.1%甲酸),流动相B为10%乙腈水溶液(含5 mmol/L甲酸铵和0.1%甲酸),梯度洗脱。采用电喷雾离子源(ESI),在正离子模式下进行测定,通过标准加入法进行定量分析。实验对比了不同色谱柱对有机胺类化合物的保留能力以及不同流动相的影响,并对方法进行了方法学验证。结果表明:9种有机胺类化合物在0.04~25000 ng/mL范围内线性关系良好,线性相关系数(R²)均≥0.9910;方法的检出限(LOD)为0.0004~0.0080 ng/mL,方法的定量限(LOQ)为0.0035~0.0400 ng/mL;在1、1.5、3倍样本浓度添加水平下,方法的平均回收率为85.30%~104.26%,相对标准偏差(RSD)为0.04%~7.95%。应用建立的方法对某项目现场样品的吸收废液进行检测,9种有机胺类化合物均能被有效检测。对实际样品进行稳定性测试,于4 ℃条件下,在48 h内RSD为0.10%~6.35%。该方法灵敏、准确、快速、简便,可为有机胺类化合物的检测提供参考,并为CO₂捕集技术的开发和工业化应用提供有力的技术支持。

关键词: 亲水相互作用色谱, 静电场轨道阱高分辨质谱, 有机胺类化合物, CO₂吸收剂

Abstract:

Carbon dioxide (CO₂) absorption and capture is an effective measure to achieve the “dual carbon” goal of carbon peak and carbon neutrality in China. Organic amine compounds are widely used in the industrial separation and recovery of CO₂. Thus, the establishment of analytical methods for organic amine compounds is of great significance for the research and development of carbon capture and storage (CCS) technology and carbon capture, utilization and storage (CCUS) technology. In this study, a method was developed for the determination of nine organic amine compounds in CO₂ absorption liquid by hydrophilic interaction liquid chromatography (HILIC)-electrostatic field orbitrap high resolution mass spectrometry. The sample was diluted with water and filtered through a 0.22 μm nylon membrane before sampling and analysis. An Accucore HILIC column (100 mm×2.1 mm, 2.6 μm) was used for separation at 30 ℃. Gradient elution was conducted using 90% acetonitrile aqueous solution containing 5 mmol/L ammonium formate and 0.1% formic acid as mobile phase A and 10% acetonitrile aqueous solution containing 5 mmol/L ammonium formate and 0.1% formic acid as mobile phase B. Determination was performed using an electrospray ion source (ESI) in the positive ion mode. The quantitative analysis was carried out by standard addition method. The chromatographic retention performance of different chromatographic columns and the influence of different mobile phases on the separation of the organic amine compounds were compared, and the method was validated. The results showed that the linear ranges of the nine organic amine compounds were 0.04-25000 ng/mL with the linear correlation coefficients (R²) greater than 0.9910. The limits of detection (LODs) of the method were in the range of 0.0004-0.0080 ng/mL, and the limits of quantification (LOQs) of the method were in the range of 0.0035-0.0400 ng/mL. The average recoveries of the method ranged from 85.30% to 104.26% with relative standard deviations (RSDs) of 0.04%-7.95% at the spiked levels of 1, 1.5 and 3 times sample concentration. The established method was applied to detect the absorption waste liquid of a cement plant, and nine organic amine compounds could be effectively detected. The stability of the actual sample was tested, and the RSDs were 0.10%-6.35% in 48 h at 4 ℃. The method is sensitive, rapid and accurate for the determination of the nine organic amine compounds in industrial waste water. It can provide reference for the detection of organic amine compounds, and provide strong technical support for the research and industrial application of CO₂ capture technology.

Key words: hydrophilic interaction liquid chromatography (HILIC), electrostatic field orbitrap high resolution mass spectrometry, organic amine compounds, carbon dioxide (CO₂) absorbent

中图分类号:

O658

唐泽坤, 万慧慧, 李红, 陈绍云, 赵金凤, 孙玉明, 蔡蕊, 徐强, 张华. 亲水相互作用色谱-静电场轨道阱高分辨质谱法测定CO₂吸收液中9种有机胺类化合物[J]. 色谱, 2023, 41(9): 799-806.

TANG Zekun, WAN Huihui, LI Hong, CHEN Shaoyun, ZHAO Jinfeng, SUN Yuming, CAI Rui, XU Qiang, ZHANG Hua. Determination of nine organic amine compounds in CO₂ absorption liquid by hydrophilic interaction liquid chromatography-electrostatic field orbitrap high resolution mass spectrometry[J]. Chinese Journal of Chromatography, 2023, 41(9): 799-806.

图/表 6

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No.	Compound	t_R/min	Ion mode	Predicated ion (m/z)	Observed ion (m/z)	Product ions (m/z)
1	AMPD	5.38	[M+H]⁺	106.08626	106.08691	88.07599, 71.04965
2	PZ	10.40	[M+H]⁺	87.09167	87.09198	85.07635, 70.07570
3	DMEA	5.78	[M+H]⁺	90.09134	90.09156	72.08132, 70.06561
4	EMEA	6.78	[M+H]⁺	90.09134	90.09156	72.08130, 70.06569
5	AEEA	10.08	[M+H]⁺	105.10224	105.10227	88.07602, 70.06571
6	DMCHA	5.13	[M+H]⁺	128.14338	128.14301	83.08586, 55.05496
7	MMEA	6.18	[M+H]⁺	76.07570	76.07606	58.06579, 56.05017
8	MDEA	6.58	[M+H]⁺	120.10191	120.10165	102.09143, 58.06580
9	DEAE	6.10	[M+H]⁺	118.12264	118.12241	100.11222, 72.08123

No.	Compound	t_R/min	Ion mode	Predicated ion (m/z)	Observed ion (m/z)	Product ions (m/z)
1	AMPD	5.38	[M+H]⁺	106.08626	106.08691	88.07599, 71.04965
2	PZ	10.40	[M+H]⁺	87.09167	87.09198	85.07635, 70.07570
3	DMEA	5.78	[M+H]⁺	90.09134	90.09156	72.08132, 70.06561
4	EMEA	6.78	[M+H]⁺	90.09134	90.09156	72.08130, 70.06569
5	AEEA	10.08	[M+H]⁺	105.10224	105.10227	88.07602, 70.06571
6	DMCHA	5.13	[M+H]⁺	128.14338	128.14301	83.08586, 55.05496
7	MMEA	6.18	[M+H]⁺	76.07570	76.07606	58.06579, 56.05017
8	MDEA	6.58	[M+H]⁺	120.10191	120.10165	102.09143, 58.06580
9	DEAE	6.10	[M+H]⁺	118.12264	118.12241	100.11222, 72.08123

No.	Compound	Linear range/ (ng/mL)	Linear equations			R²			LOD/ (ng/mL)		LOQ/ (ng/mL)
No.	Compound	Linear range/ (ng/mL)	Sample 1	Sample 2	Sample 3	Sample 1	Sample 2	Sample 3	LOD/ (ng/mL)		LOQ/ (ng/mL)
1	AMPD	0.04-25000	y=1.3005x+805166	y=1.6144x+17965	y=1.6472x+116565	0.9984	0.9910	0.9926		0.0030	0.0250
2	PZ	0.04-25000	y=3.3012x+5.25675	y=3.4960x+5.03065	y=4.1866x+5.18668	0.9995	0.9987	0.9981		0.0030	0.0250
3	DMEA	0.04-25000	y=2.8453x+3.36330	y=4.0884x+6.60093	y=4.1026x+6.56735	0.9989	0.9980	0.9981		0.0030	0.0350
4	EMEA	0.04-25000	y=2.9006x+6.90375	y=3.77495x+4.92543	y=4.0225x+4.99919	0.9943	0.9979	0.9953		0.0020	0.0100
5	AEEA	0.04-25000	y=122330x+3.07125	y=123380x+3.1961	y=104089x+7.0628	0.9983	0.9986	0.9993		0.0004	0.0035
6	DMCHA	0.04-25000	y=4.1194x+1.73009	y=4.75736x+1.35725	y=5.41105x+1.32278	0.9999	0.9974	0.9972		0.0020	0.0100
7	MMEA	0.04-25000	y=1.1483x+5.12991	y=1.97590x+2.34735	y=1.98902x+2.01331	0.9996	0.9932	0.9926		0.0080	0.0400
8	MDEA	0.04-25000	y=556888x+3.21387	y=565067x+3.35909	y=597026x+1.14919	0.9991	0.9987	0.9957		0.0004	0.0035
9	DEAE	0.04-25000	y=4.0549x+1.22349	y=5.68936x+1.11871	y=5.49765x+2.46986	0.9910	0.9947	0.9994		0.0050	0.0200

No.	Compound	Linear range/ (ng/mL)	Linear equations			R²			LOD/ (ng/mL)		LOQ/ (ng/mL)
No.	Compound	Linear range/ (ng/mL)	Sample 1	Sample 2	Sample 3	Sample 1	Sample 2	Sample 3	LOD/ (ng/mL)		LOQ/ (ng/mL)
1	AMPD	0.04-25000	y=1.3005x+805166	y=1.6144x+17965	y=1.6472x+116565	0.9984	0.9910	0.9926		0.0030	0.0250
2	PZ	0.04-25000	y=3.3012x+5.25675	y=3.4960x+5.03065	y=4.1866x+5.18668	0.9995	0.9987	0.9981		0.0030	0.0250
3	DMEA	0.04-25000	y=2.8453x+3.36330	y=4.0884x+6.60093	y=4.1026x+6.56735	0.9989	0.9980	0.9981		0.0030	0.0350
4	EMEA	0.04-25000	y=2.9006x+6.90375	y=3.77495x+4.92543	y=4.0225x+4.99919	0.9943	0.9979	0.9953		0.0020	0.0100
5	AEEA	0.04-25000	y=122330x+3.07125	y=123380x+3.1961	y=104089x+7.0628	0.9983	0.9986	0.9993		0.0004	0.0035
6	DMCHA	0.04-25000	y=4.1194x+1.73009	y=4.75736x+1.35725	y=5.41105x+1.32278	0.9999	0.9974	0.9972		0.0020	0.0100
7	MMEA	0.04-25000	y=1.1483x+5.12991	y=1.97590x+2.34735	y=1.98902x+2.01331	0.9996	0.9932	0.9926		0.0080	0.0400
8	MDEA	0.04-25000	y=556888x+3.21387	y=565067x+3.35909	y=597026x+1.14919	0.9991	0.9987	0.9957		0.0004	0.0035
9	DEAE	0.04-25000	y=4.0549x+1.22349	y=5.68936x+1.11871	y=5.49765x+2.46986	0.9910	0.9947	0.9994		0.0050	0.0200

Compound	Sample 1			Sample 2			Sample 3
Compound	Added/(ng/mL)	Recovery/%	RSD/%	Added/(ng/mL)	Recovery/%	RSD/%	Added/(ng/mL)	Recovery/%	RSD/%
AMPD	0.60	89.24	0.23	0.20	97.75	1.58	0.30	89.84	5.60
	0.90	90.94	0.07	0.30	103.55	1.21	0.45	91.20	1.51
	1.80	95.17	0.16	0.60	95.61	0.19	0.90	91.75	1.06
PZ	6.00	97.23	0.16	5.00	90.74	5.16	30	91.13	1.21
	9.00	90.59	0.51	7.50	91.65	3.59	45	92.58	0.57
	18.0	96.57	1.10	15.0	92.99	1.71	90	95.36	1.30
DMEA	2.00	95.31	1.31	5.00	98.29	0.2	4.00	92.03	3.22
	3.00	92.84	1.63	7.50	100.91	0.3	6.00	97.60	0.13
	6.00	93.20	0.22	15	97.38	0.6	12.0	98.85	1.46
EMEA	1.00	104.26	0.14	0.20	91.25	1.50	5.00	97.68	0.73
	1.50	96.26	0.21	0.30	96.74	0.37	7.50	96.72	0.18
	3.00	92.34	0.31	0.60	91.59	0.11	15.0	97.32	0.04
AEEA	1400	99.68	2.17	6.00	97.56	2.65	300	97.78	1.25
	2100	97.88	1.76	9.00	94.91	3.98	1000	98.98	0.20
	4200	97.73	1.37	18.0	95.37	7.95	1500	95.96	0.83
DMCHA	0.70	85.30	3.50	0.50	87.30	3.72	0.20	87.60	5.43
	1.05	92.16	3.20	0.75	96.02	5.58	0.30	92.59	3.28
	2.10	90.34	0.12	1.50	103.03	1.16	0.60	95.20	1.66
MMEA	100	98.74	4.19	5.00	98.65	2.09	6.00	90.92	1.95
	150	99.64	0.69	7.50	95.62	2.33	9.00	92.61	0.74
	300	97.48	2.33	15.0	90.25	1.63	18.00	92.47	1.06
MDEA	500	98.62	3.20	350	97.58	2.16	250	96.01	2.78
	750	97.79	0.54	525	92.30	1.15	375	96.80	0.95
	1500	94.69	1.13	1750	92.09	3.06	1250	91.93	1.10
DEAE	3.00	93.69	4.02	0.50	102.96	2.35	15	93.74	3.38
	4.50	95.48	0.81	0.75	98.10	3.53	20	95.95	1.15
	9.00	95.05	1.11	1.50	94.17	7.05	50	91.98	0.17

亲水相互作用色谱-静电场轨道阱高分辨质谱法测定CO₂吸收液中9种有机胺类化合物

Determination of nine organic amine compounds in CO₂ absorption liquid by hydrophilic interaction liquid chromatography-electrostatic field orbitrap high resolution mass spectrometry

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Metrics

Compound	Matrix	Contents/(ng/mL)					RSD/%
Compound	Matrix	0 h	12 h	24 h	36 h	48 h	RSD/%
AMPD	sample 1	0.584	0.574	0.569	0.573	0.577	0.97
	sample 2	0.163	0.164	0.166	0.171	0.182	4.60
	sample 3	0.323	0.321	0.338	0.309	0.311	3.61
PZ	sample 1	6.170	6.351	5.872	6.144	6.208	2.83
	sample 2	4.522	4.514	4.494	4.601	4.504	0.94
	sample 3	26.944	26.816	25.872	26.144	25.988	1.87
DMEA	sample 1	2.605	2.602	2.487	2.727	2.631	3.28
	sample 2	0.229	0.248	0.239	0.249	0.250	3.69
	sample 3	3.616	3.633	3.487	3.727	3.599	2.38
EMEA	sample 1	1.000	0.904	0.989	1.006	1.082	6.35
	sample 2	0.178	0.179	0.188	0.183	0.185	2.28
	sample 3	0
AEEA	sample 1	1374.88	1374.25	1373.55	1375.83	1377.25	0.10
	sample 2	6.275	6.351	6.475	5.998	6.051	3.24
	sample 3	318.875	317.153	316.475	322.998	319.817	0.81
DMCHA	sample 1	0.696	0.754	0.666	0.669	0.709	5.12
	sample 2	0.525	0.537	0.544	0.544	0.518	2.19
	sample 3	0.182	0.177	0.190	0.185	0.187	2.70
MMEA	sample 1	113.395	114.752	113.397	112.037	115.021	1.06
	sample 2	4.514	4.539	4.382	4.622	4.489	1.93
	sample 3	6.064	6.189	6.382	5.962	6.003	2.77
MDEA	sample 1	453.847	452.270	456.942	453.330	455.201	0.40
	sample 2	336.094	335.858	340.094	332.330	334.236	0.86
	sample 3	246.459	243.952	238.094	257.330	247.454	2.83
DEAE	sample 1	2.593	2.592	2.627	2.603	2.612	0.56
	sample 2	0.472	0.481	0.518	0.468	0.478	4.14
	sample 3	13.480	13.478	13.318	13.468	13.502	0.55

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