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

doi:10.3724/SP.J.1123.2022.12014

Abstract

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

CLC Number:

O658

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.

Figures/Tables 6

References

[1]	Vaidya P D, Kenig E Y,. Chem Eng Sci, 2007, 62(24): 7344
[2]	Bindwal A B, Vaidya P D, Kenig E Y,. Chem Eng Sci, 2011, 169(1-3): 144
[3]	Li H, Ji K, Qi T Q J, et al. Chemical Industry and Engineering Progress, 2022, 41(2): 1025
[3]	李红, 吉轲, 齐天勤机, 等. 化工进展, 2022, 41(2): 1025
[4]	Campo P, Suidan M T, Chai Y, et al. Talanta, 2010, 80(3): 1110
[5]	Zhang Y Q, Lu W Y, Wang X Q, et al. The Administration and Technique of Environmental Monitoring, 2020, 32(4): 48
[5]	张嫣秋, 陆伟英, 王嬉巧, 等. 环境监测管理与技术, 2020, 32(4): 48
[6]	Hamzah N, Kjellberg M, Vanninen P. J Chromatogr B, 2021, 1176: 1
[7]	Chen M S, Liang Z, Tang H Y, et al. Chinese Journal of Analysis Laboratory, 2018, 37(10): 1183
[7]	陈旻实, 梁震, 唐寰宇, 等. 分析试验室, 2018, 37(10): 1183
[8]	Zhong Z, Li G, Zhong X, et al. Talanta, 2013, 115: 518
[9]	Wang T L, Lopez M A M, Hagen S T, et al. Fresenius Environ Bull, 2012, 21(8A): 2298
[10]	Ye M L, Chen Y. Journal of Zhejiang University Science Edition, 2011, 38(4): 433
[10]	叶明立, 陈郁. 浙江大学学报(理学版), 2011, 38(4): 433
[11]	Wang X D, Lan J, Di B. Chinese Journal of New Drugs, 2012, 21(16): 1942
[11]	王晓东, 蓝娟, 狄斌. 中国新药杂志, 2012, 21(16): 1942
[12]	Janeckova M, Bartos M, Lencova J. Monatsh Chem, 2019, 150(3): 387
[13]	Lin C F, Liu J T, Lin C H,. Anal Sci, 2009, 25(7): 845
[14]	Ohsawa I, Seto Y. J Chromatogr A, 2006, 1122(1/2): 242
[15]	Kenar L, Alp O. J Chromatogr Sci, 2011, 49(5): 361
[16]	Chandra B, Sinha Roy K, Shaik M, et al. Rapid Commun Mass Spectrom, 2020, 34(12): 1
[17]	Valdez C A, Leif R N, Hok S, et al. Rev Anal Chem, 2018, 37(1): 1
[18]	Read R W, Black R M. J Chromatogr A, 1999, 862(2): 169
[19]	Baygildiev T, Vokuev M, Braun A, et al. J Chromatogr B, 2021, 1162: 1
[20]	Otsuka M, Miyaguchi H, Uchiyama M. J Chromatogr A, 2020, 1625: 1
[21]	Dong Y, Ma Y, Yan K, et al. J Chromatogr B, 2014, 957: 30
[22]	Otsuka M, Miyaguchi H, Uchiyama M. J Chromatogr A, 2019, 1602: 199
[23]	Reddy M K, Mills G, Nixon C, et al. J Chromatogr B, 2011, 879(24): 2383
[24]	Willison S A. J Chromatogr A, 2012, 1270: 72
[25]	Li H Y, Wang H Y, Xiong X T, et al. Journal of Instrumental Analysis, 2018, 37(8): 930
[25]	李慧勇, 王海洋, 熊小婷, 等. 分析测试学报, 2018, 37(8): 930
[26]	Makarov A, Scigelova M. J Chromatogr A, 2010, 1217(25): 3938
[27]	Gu Y, Zang P, Li J X, et al. Chinese Journal of Chromatography, 2022, 40(8): 736
[27]	谷艳, 臧鹏, 李进霞, 等. 色谱, 2022, 40(8): 736
[28]	Zhang H W, Xia H M, Liu H, et al. Chinese Journal of Chromatography, 2022, 40(7): 653
[28]	张慧文, 夏慧敏, 刘宏, 等. 色谱, 2022, 40(7): 653

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

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

RichHTML

PDF

Knowledge

Abstract

Cite this article

share this article

share this article

Figures/Tables 6

References

Related Articles 15

Recommended Articles

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

[1]	HE Liying, TANG Xiaoqin, ZHAO Jian, YANG Qianzhan, LI Li. Determination of five amanita peptide toxins in poisonous mushrooms by ultra performance liquid chromatography-quadrupole electrostatic field orbitrap high resolution mass spectrometry [J]. Chinese Journal of Chromatography, 2023, 41(1): 94-103.
[2]	LIU Mengfei, WANG Mei, ZHAO Ang, ZHU Lin, WANG Chun, WEI Chao, LIU Wei, XU Jianzhong. Determination of organophosphate diesters in facility vegetable soils using ultra-high performance liquid chromatography-electrostatic field orbitrap high resolution mass spectrometry [J]. Chinese Journal of Chromatography, 2023, 41(1): 58-65.
[3]	GU Yan, ZANG Peng, LI Jinxia, YAN Yanyan, WANG Jia. Plasma metabolomics in a deep vein thrombosis rat model based on ultra-high performance liquid chromatography-electrostatic field orbitrap high resolution mass spectrometry [J]. Chinese Journal of Chromatography, 2022, 40(8): 736-745.
[4]	SHANG Weiwei, SUO Decheng, LI Tong, DU Qiuling, JIANG Xianhong, WANG Peilong. Metal-organic framework UiO-67-based enrichment and purification of progesterone residues in milk [J]. Chinese Journal of Chromatography, 2022, 40(8): 712-720.
[5]	SUN Lingli, LIU Jia, GUO Xiujie, WU Lidong, DUAN Zhengchao, WANG Chaoran, WANG Lianzhi. Hydrophilic interaction liquid chromatography for removal of pesticide residues in ginseng extracts [J]. Chinese Journal of Chromatography, 2021, 39(4): 444-452.
[6]	LI Dapeng, XIE Guangshan, XIE Peisi, ZHU Lin, CAI Zongwei. Synthesis of zwitterionic dual-functional metal-organic framework nanocomposite with ultra-hydrophilicity for selective enrichment of glycopeptides [J]. Chinese Journal of Chromatography, 2021, 39(3): 205-210.
[7]	GAO Jie, WU Qi, CHEN Lixiao, LI Hui, DONG Shuqing, LUO Guoying, ZHANG Shusheng, QIU Hongdeng, ZHAO Liang. Preparation of reversed-phase/hydrophilic chromatographic stationary phase based on dialdehyde microcrystalline cellulose-functionalized C₁₈ [J]. Chinese Journal of Chromatography, 2020, 38(4): 414-423.
[8]	ZHANG Xianchen, ZHANG Pengjie, SHI Chengyu, HUA Hongbo, RONG Yutang, LU Junwen, YANG Fang. Rapid determination of 48 contaminant residues in food contact plastic products by ultra performance liquid chromatography-quadrupole/electrostatic field orbitrap high resolution mass spectrometry coupled with microwave-assisted extraction [J]. Chinese Journal of Chromatography, 2018, 36(7): 634-642.
[9]	FAN Guangyu, FENG Feng, ZHANG Feng, GAO Fei, LI Xiaoming, LIANG Zhengang. Determination of 14 sweeteners in liquid foods by hydrophilic interaction liquid chromatography-tandem mass spectrometry [J]. Chinese Journal of Chromatography, 2018, 36(4): 351-355.
[10]	ZHANG Xianchen, LI Rong, ZHANG Pengjie, WU Xia, HUA Hongbo, YANG Luqi, LU Junwen, RONG Yutang. Rapid determination of 25 drug residues in aquatic products by ultra performance liquid chromatography-quadrupole/electrostatic field orbitrap high resolution mass spectrometry [J]. Chinese Journal of Chromatography, 2018, 36(2): 114-124.
[11]	ZHANG Rong, LIU Xin, PENG Yuan, LIU Weihua, ZHANG Licheng, DAI Ying, LI Shasha, GAO Zhixian. Rapid determination of 95 herbicide residues in tea by modified QuEChERS coupled with ultra-high performance liquid chromatography-quadrupole/electrostatic field orbitrap high resolution mass spectrometry [J]. Chinese Journal of Chromatography, 2018, 36(12): 1228-1237.
[12]	HUANG Wenwen, GOU Xinlei, HU Tiejing, HU Guanghui, ZHAO Xinying. Determination of cholesterol and its six metabolism markers in serum by high performance liquid chromatography-quadrupole/electrostatic field orbitrap high resolution mass spectrometry [J]. Chinese Journal of Chromatography, 2018, 36(10): 985-990.
[13]	JIA Youmei, CAI Jianfeng, XIN Huaxia, FENG Jiatao, FU Yanhui, FU Qing, JIN Yu. Separation and purification of the components in Trachelospermum jasminoides by two dimensional hydrophilic interaction liquid chromatography- reversed-phase liquid chromatography [J]. Chinese Journal of Chromatography, 2017, 35(6): 650-655.
[14]	ZHAN Lina, CHEN Qin, GU Shuqing, DENG Xiaojun. Determination of milk allergen caseins in foods by ultra performance liquid chromatography-quadrupole/electrostatic field orbitrap high resolution mass spectrometry [J]. Chinese Journal of Chromatography, 2017, 35(4): 405-412.
[15]	WANG Hui, XIN Huaxia, CAI Jianfeng, LI Fangbing, JIN Yu, FU Qing. Fingerprint profiling of Astragalus polysaccharides based on partial acid hydrolysis-hydrophilic interaction chromatography analysis and comprehensive quality evaluation of Astragalus membranaceus combined with reversed-phase liquid chromatography fingerprint analysis [J]. Chinese Journal of Chromatography, 2016, 34(7): 726-736.