退役锂电池放电废水特征有机污染物解析

doi:10.16085/j.issn.1000-6613.2021-2486

化工进展 ›› 2022, Vol. 41 ›› Issue (10): 5619-5629.DOI: 10.16085/j.issn.1000-6613.2021-2486

退役锂电池放电废水特征有机污染物解析

刘肖贝¹^,²(), 张西华¹(), 熊梅²(), 赵赫²

^1.上海第二工业大学资源与环境工程学院，上海电子废弃物资源化协同创新中心，上海 201209
^2.中国科学院过程工程研究所环境技术与工程研究部，绿色过程与工程重点实验室，北京市过程污染控制工程技术研究中心，北京 100190

收稿日期:2021-12-03 修回日期:2022-04-26 出版日期:2022-10-20 发布日期:2022-10-21
通讯作者: 张西华,熊梅
作者简介:刘肖贝（1997—），女，硕士研究生，研究方向为退役锂电池放电废水特征污染物筛查。E-mail：1031489122@qq.com。
基金资助:
上海市高原学科——环境科学与工程（资源循环科学与工程）资助项目;中国科学院重点部署项目(ZDRW_CN_2020-1)

Analysis on the characteristic organic pollutants from discharge wastewater of spent lithium batteries

LIU Xiaobei¹^,²(), ZHANG Xihua¹(), XIONG Mei²(), ZHAO He²

^1.School of Resources and Environmental Engineering, Shanghai Polytechnic University, Shanghai Collaborative Innovation Center for WEEE Recycling, Shanghai 201209, China
^2.Beijing Engineering Research Center of Process Pollution Control, Key Laboratory of Green Process and Engineering, Division of Environment Technology and Engineering, Institute of Process Engineering, Chinese Academy of Sciences, Beijing 100190, China

Received:2021-12-03 Revised:2022-04-26 Online:2022-10-20 Published:2022-10-21
Contact: ZHANG Xihua, XIONG Mei

摘要/Abstract

摘要：

为研究退役锂电池盐水溶液放电产生的放电废水有机物的种类与来源，首先采用单因素优化方法对萃取剂类型、pH、萃取次数3个因素进行液-液萃取前处理优化实验，获得最佳萃取预处理条件。接着采用气相色谱与质谱联用（GC-MS）程序中分流比和升温模式对比实验，建立了放电废水有机成分定性分析方法，并对检出的有机污染物进行分类与来源判断。研究结果表明，选取乙酸乙酯为萃取剂，调节放电废水pH至9.38，以8000 r/min离心5min（4℃），且采用间歇三次萃取时分离效果最优。对放电废水SIM定性扫描检测出10类有机污染物，其中酸酯类、酰胺类、烷烃类物质较多，且来源于反应衍生物与电解液添加剂的占比较大，分别为33.3%与20%，包括电解质增塑剂间苯二甲酸二(2-乙基己基)酯，电解液溶剂效应产物1,4-环己烷二羧酸二甲酯、磷酸三(2-氯乙基)酯，电解液添加剂硬脂酰胺、十六碳酰胺、十四酰胺、1,4-环己烷二甲醇二乙烯醚，退役锂电池塑料外壳中抗氧剂原料3,5-二叔丁基苯酚等。这些物质对水环境均具有不同程度的毒性危害，需进一步检测各有机物浓度并揭示其迁移转化规律，建立退役锂电池放电废水重点关注有机污染物清单。

关键词: 放电废水, 退役锂电池, 有机污染物, 定性分析

Abstract:

To study the types and sources of organic substances from wastewater generated during the discharge of spent lithium batteries by saline solution, a single-factor optimization method was used to optimize the liquid -liquid extraction pretreatment and the optimal extraction conditions were obtained by investigating the types of extraction agents, pH, and extraction times. Then, a qualitative analysis method for detecting organic substances from discharge wastewater of spent lithium batteries was established using the gas chromatography-mass spectrometry (GC-MS) program with comparative tests of splitting ratio and ramp-up modes, and the detected organic pollutants can be classified and the sources can also be determined. The results showed that the optimal separation effect could be achieved under the following extraction conditions: ethyl acetate as the extraction agent, adjusting the pH of the discharge wastewater to 9.38, centrifugalizing with 8000r/min at 4℃ for 5min, and extracting three times under intermittent mode. Ten types of organic pollutants can be detected from the discharge wastewater by SIM qualitative scanning, among which acid esters, amides and alkanes are more abundant, and those from reaction derivatives and electrolyte additives account for 33.3% and 20%, respectively. The detected organic pollutants mainly include bis(2-ethylhexyl) isophthalate deriving from electrolyte plasticizer; 1,4-cyclohexanedicarboxylic acid dimethyl ester and tris(2-chloroethyl) phosphate from electrolyte solvent effect products; stearyl amide, hexadecanamide, tetradecanamide, 1,4-cyclohexanedimethanol divinyl ether from electrolyte additives; 3,5-di-tert-butylphenol from the raw materials for antioxidant in plastic shell of spent lithium batteries. In view of their toxicity effects to the water environment caused by the detected organic pollutants, it is urgent to further test the concentration of each organic pollutant and reveal their corresponding migration and transformation rules, and establish the list of critical organic pollutants which need to be paid close attention.

Key words: discharge wastewater, retired lithium batteries, organic pollutants, qualitative analysis

中图分类号:

X703

刘肖贝, 张西华, 熊梅, 赵赫. 退役锂电池放电废水特征有机污染物解析[J]. 化工进展, 2022, 41(10): 5619-5629.

LIU Xiaobei, ZHANG Xihua, XIONG Mei, ZHAO He. Analysis on the characteristic organic pollutants from discharge wastewater of spent lithium batteries[J]. Chemical Industry and Engineering Progress, 2022, 41(10): 5619-5629.

图/表 10

参考文献 39

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单因素优化项目	萃取剂名称	pH	萃取次数
方案1	十六烷	2.09	1
方案2	二氯甲烷、三氯甲烷	5.54	2
方案3	四氯化碳	7.12	3
方案4	乙酸乙酯	9.38	4
方案5	正戊烷、正己烷、正庚烷	12.15	5

单因素优化项目	萃取剂名称	pH	萃取次数
方案1	十六烷	2.09	1
方案2	二氯甲烷、三氯甲烷	5.54	2
方案3	四氯化碳	7.12	3
方案4	乙酸乙酯	9.38	4
方案5	正戊烷、正己烷、正庚烷	12.15	5

序号	类别	有机物名称	分子式	分子量	CAS#	峰面积百分比/%	匹配度/%
1	酸酯类	间苯二甲酸二(2-乙基己基)酯	C₂₄H₃₈O₄	390.5561	137-89-3	3.47	92
2		三(2,4-二叔丁基)亚磷酸苯酯	C₄₂H₆₃O₃P	646.92	31570-4-4	3.22	89
3		碳酸乙烯酯	C₃H₄O₃	88.06	96-49-1	0.87	89
4		3-甲基丁酸1,7,7-三甲基二环[2.2.1]庚-2-基酯	C₁₅H₂₆O₂	238	0-0-0	0.71	90
5		1,4-环己烷二羧酸二甲酯	C₁₀H₁₆O₄	200	19550-59-5	0.54	85
6		磷酸三(2-氯乙基)酯	C₆H₁₂Cl₃O₄P	285.49	115-96-8	0.24	87
7		十四酸乙酯	C₁₆H₃₂O₂	256.42	124-06-1	0.21	95
8	酰胺类	硬脂酰胺	C₁₈H₃₇NO	283.49	124-26-5	5.84	95
9		十六碳酰胺	C₁₆H₃₃NO	255.4393	629-54-9	3.51	95
10		十四酰胺	C₁₄H₂₉NO	227.3862	638-58-4	1.22	94
11	酚类	3,5-二叔丁基苯酚	C₁₄H₂₂O	206.3239	1138-52-9	0.29	83
12	烷烃类	十五烷	C₁₅H₃₂	212.4146	629-62-9	17.11	95
13		十一烷	C₁₁H₂₄	156.31	1120-21-4	12.23	88
14		3-乙基-3-甲基庚烷	C₁₀H₂₂	142.2817	17302-1-1	0.40	91
15	杂环类	(Z)-9-十八烯腈	C₁₈H₃₃N	263.4613	112-91-4	2.20	85
16		二环己基碳二亚胺	C₁₃H₂₂N₂	222	53508-12-6	0.40	88
17		2-溴十四烷	C₈H₁₇Br	193.125	999-6-4	0.14	70
18		溴代三十烷	C₃₀H₆₁Br	501.7093	4209-22-7	0.13	75
19	醛酮类	2,6-二甲基-5-庚烯醛	C₉H₁₆O	140	32160-45-5	0.58	67
20		4-(4'-羟基-4'-甲基戊基)-3-环己烯-1-甲醛	C₁₃H₂₂O₂	210	21720-87-6	0.28	69
21		壬醛	C₉H₁₈O	142.24	124-19-6	0.26	82
22	醇醚类	二丁醚	C₈H₁₈O	130.23	142-96-1	3.75	97
23		2,5-双(1,1-二甲基丙基)-1,4-苯二醇	C₁₆H₂₆O₂	250	452049-69-3	1.45	75
24		二乙二醇单[(1,1,3,3-四甲基丁基)苯基]醚	C₁₈H₃₀O₃	294	13804-51-8	0.77	83
25		1,4-环己烷二甲醇二乙烯醚	C₁₂H₂₀O₂	196	17351-75-6	0.70	61
26		3-(5,5,6-三甲基双环(2.2.1)庚-2-基)环己-1-醇	C₁₆H₂₈O	236	102572-89-4	0.51	75
27	腈类	丁二腈	C₄H₄N₂	80.09	110-61-2	4.76	96
28		5-氟-2-硝基苯乙腈	C₈H₅FN₂O₂	180.14	3456-75-5	0.46	71
29	腺苷类	2-羟基腺苷	C₁₀H₁₃N₅O₅	283.2407	1818-71-9	0.74	62
30	酸酐类	异十八烷基琥珀酸酐	C₂₂H₄₀O₃	352	40924-19-4	0.25	76

序号	类别	有机物名称	分子式	分子量	CAS#	峰面积百分比/%	匹配度/%
1	酸酯类	间苯二甲酸二(2-乙基己基)酯	C₂₄H₃₈O₄	390.5561	137-89-3	3.47	92
2		三(2,4-二叔丁基)亚磷酸苯酯	C₄₂H₆₃O₃P	646.92	31570-4-4	3.22	89
3		碳酸乙烯酯	C₃H₄O₃	88.06	96-49-1	0.87	89
4		3-甲基丁酸1,7,7-三甲基二环[2.2.1]庚-2-基酯	C₁₅H₂₆O₂	238	0-0-0	0.71	90
5		1,4-环己烷二羧酸二甲酯	C₁₀H₁₆O₄	200	19550-59-5	0.54	85
6		磷酸三(2-氯乙基)酯	C₆H₁₂Cl₃O₄P	285.49	115-96-8	0.24	87
7		十四酸乙酯	C₁₆H₃₂O₂	256.42	124-06-1	0.21	95
8	酰胺类	硬脂酰胺	C₁₈H₃₇NO	283.49	124-26-5	5.84	95
9		十六碳酰胺	C₁₆H₃₃NO	255.4393	629-54-9	3.51	95
10		十四酰胺	C₁₄H₂₉NO	227.3862	638-58-4	1.22	94
11	酚类	3,5-二叔丁基苯酚	C₁₄H₂₂O	206.3239	1138-52-9	0.29	83
12	烷烃类	十五烷	C₁₅H₃₂	212.4146	629-62-9	17.11	95
13		十一烷	C₁₁H₂₄	156.31	1120-21-4	12.23	88
14		3-乙基-3-甲基庚烷	C₁₀H₂₂	142.2817	17302-1-1	0.40	91
15	杂环类	(Z)-9-十八烯腈	C₁₈H₃₃N	263.4613	112-91-4	2.20	85
16		二环己基碳二亚胺	C₁₃H₂₂N₂	222	53508-12-6	0.40	88
17		2-溴十四烷	C₈H₁₇Br	193.125	999-6-4	0.14	70
18		溴代三十烷	C₃₀H₆₁Br	501.7093	4209-22-7	0.13	75
19	醛酮类	2,6-二甲基-5-庚烯醛	C₉H₁₆O	140	32160-45-5	0.58	67
20		4-(4'-羟基-4'-甲基戊基)-3-环己烯-1-甲醛	C₁₃H₂₂O₂	210	21720-87-6	0.28	69
21		壬醛	C₉H₁₈O	142.24	124-19-6	0.26	82
22	醇醚类	二丁醚	C₈H₁₈O	130.23	142-96-1	3.75	97
23		2,5-双(1,1-二甲基丙基)-1,4-苯二醇	C₁₆H₂₆O₂	250	452049-69-3	1.45	75
24		二乙二醇单[(1,1,3,3-四甲基丁基)苯基]醚	C₁₈H₃₀O₃	294	13804-51-8	0.77	83
25		1,4-环己烷二甲醇二乙烯醚	C₁₂H₂₀O₂	196	17351-75-6	0.70	61
26		3-(5,5,6-三甲基双环(2.2.1)庚-2-基)环己-1-醇	C₁₆H₂₈O	236	102572-89-4	0.51	75
27	腈类	丁二腈	C₄H₄N₂	80.09	110-61-2	4.76	96
28		5-氟-2-硝基苯乙腈	C₈H₅FN₂O₂	180.14	3456-75-5	0.46	71
29	腺苷类	2-羟基腺苷	C₁₀H₁₃N₅O₅	283.2407	1818-71-9	0.74	62
30	酸酐类	异十八烷基琥珀酸酐	C₂₂H₄₀O₃	352	40924-19-4	0.25	76

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退役锂电池放电废水特征有机污染物解析

Analysis on the characteristic organic pollutants from discharge wastewater of spent lithium batteries

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