高分辨质谱技术在有机污染物降解产物鉴定中的应用进展
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摘要
有机污染物在水处理过程中会发生降解反应,其降解产物的毒性可能会比母体化合物更大,因此开展有机污染物降解产物的检测、鉴定和毒性评估具有重要意义。针对水处理过程中有机污染物的组分转化及结构变化,归纳了轨道离子阱质谱和飞行时间质谱等几种高分辨质谱技术在有机污染物降解产物检测与鉴定中的技术特性和独特优势,总结了高分辨质谱技术对农药、塑化剂、抗生素、亚硝胺、微囊藻毒素五类新兴有机污染物检测的色谱质谱分析条件以及在水处理有机污染物降解产物鉴定中的应用成效,并展望了高分辨质谱技术在该领域未来的发展方向。
As organic pollutants may degrade in the process of water treatment,and their degradation products may be more toxic than the parent compounds,it is important to conduct detection and identification of degradation products of organic pollutants.This paper summarizes the technical characteristics and unique advantages of several high-resolution mass spectrometry technologies,such as orbitrap mass spectrometry and time-of-flight mass spectrometry,for detecting degradation products of organic pollutants.Then the paper sums up the chromatographic mass spectrometry analysis conditions of five emerging pollutants,including pesticides,plasticizers,antibiotics,nitrosamines,and microcystins,and the application effectiveness of identification of degradation products of water treatment.Finally,the paper prospects the development directions of high-resolution mass spectrometry in this field.
As organic pollutants may degrade in the process of water treatment,and their degradation products may be more toxic than the parent compounds,it is important to conduct detection and identification of degradation products of organic pollutants.This paper summarizes the technical characteristics and unique advantages of several high-resolution mass spectrometry technologies,such as orbitrap mass spectrometry and time-of-flight mass spectrometry,for detecting degradation products of organic pollutants.Then the paper sums up the chromatographic mass spectrometry analysis conditions of five emerging pollutants,including pesticides,plasticizers,antibiotics,nitrosamines,and microcystins,and the application effectiveness of identification of degradation products of water treatment.Finally,the paper prospects the development directions of high-resolution mass spectrometry in this field.
引文
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[2]Rousis N I,Bade R,Bijlsma L,et al.Monitoring a large number of pesticides and transformation products in water samples from Spain and Italy[J].Environmental Research,2017,156:31-38.
[3]张瑞娟,姚宇霞,党晋华,等.加速溶剂萃取-固相萃取净化-气相色谱法测定土壤中17种有机氯农药[J].安全与环境工程,2017,24(4):74-78.
[4]陈文婷,向发椿,徐健蓉,等.高效液相色谱法测定水和土壤中氟唑菌酰胺残留[J].农药,2017,56(5):351-353.
[5]Li Z G,Qian Z Y,Hu S Y,et al.Molecularly imprinted solid phase extraction coupled with gas chromatography-mass spectrometry for determination of N-Nitrosodiphenylamine in water samples[J].Chemosphere,2018,212:872-880.
[6]吴春英,白鹭,谷风,等.超高效液相色谱-串联质谱法同时检测水中16种芳氧苯氧丙酸酯类除草剂[J].安全与环境工程,2016,23(5):97-101.
[7]Fu Y Q,Zhao C X,Lu X,et al.Nontargeted screening of chemical contaminants and illegal additives in food based on liquid chromatography-high resolution mass spectrometry[J].Trends in Analytical Chemistry,2017,96:89-98.
[8]Agüera A,Piernas A B M,Ma1as M C C.Analytical strategies used in HRMS[M]//Applications in High Resolution Mass Spectrometry:Food Safety and Pesticide Residue Analysis.Amstedam:Elsevier,2017.
[9]李明,马家辰,李红梅,等.静电场轨道阱质谱的进展[J].质谱学报,2013,34(3):185-192.
[10]Makarov A,Scigelova M.Coupling liquid chromatography to orbitrap mass spectrometry[J].Journal of Chromatography A,2010,1217:3938-3945.
[11]Rivera Z H,Oosterink E,Rietveld L,et al.Influence of natural organic matter on the screening of pharmaceuticals in water by using liquid chromatography with full scan mass spectrometry[J].Analytica Chimica Acta,2011,700(1/2):114-125.
[12]Meng X S,Bai H,Guo T,et al.Broad screening of illicit ingredients in cosmetics using ultra-high-performance liquid chromatography-hybrid quadrupole-Orbitrap mass spectrometry with customized accurate-mass database and mass spectral library[J].Journal of Chromatography A,2017,1528:61-74.
[13]Mao J F,Zheng N,Wen F,et al.Multi-mycotoxins analysis in raw milk by ultra high performance liquid chromatography coupled to quadrupole orbitrap mass spectrometry[J].Food Control,2018,84:305-311.
[14]Glicksberg L,Bryand K,Kerrigan S.Identification and quantification of synthetic cathinones in blood andurine using liquid chromatography-quadrupole/time of flight(LC-Q/TOF)mass spectrometry[J].Journal of Chromatography B,2016,1035:91-103.
[15]Kioussi M K,Lyris E M,Angelis Y S,et al.A generic screening methodology for horse doping control by LC-TOF-MS,GC-HRMS and GC-MS[J].Journal of Chromatography B,2013,941:69-80.
[16]Hisaindee S,Meetani M A,Rauf M A.Application of LC-MS to the analysis of advanced oxidation process(AOP)degradation of dye products and reaction mechanisms[J].Trends in Analytical Chemistry,2013,49:31-44.
[17]Kaufmann A,Butcher P,Maden K,et al.Quantitative and confirmative performance of liquid chromatography coupled to highresolution mass spectrometry compared to tandem mass spectrometry[J].Rapid Communication in Mass Spectrometry,2011,25(7):979-992.
[18]Deeb A A,Stephan S,Schmitz J,et al.Suspect screening of micropollutants and their transformation products in advanced wastewater treatment[J].Science of the Total Environment,2017,601/602:1247-1253.
[19]王丽,俞心愉,李磊.超高效液相色谱-高分辨质谱法快速检测白酒中4种甜味剂[J].中国卫生检验杂志,2014,24(22):3244-3246.
[20]Park N,Choi Y,Kim D,et al.Prioritization of highly exposable pharmaceuticals via a suspect/non-target screening approach:Acase study for Yeongsan River,Korea[J].Science of the Total Environment,2018,639(11):570-579.
[21]Ace1al J,Stampachiacchiere S,Pérez S,et al.Advances in liquid chromatography-high-resolution mass spectrometry for quantitative and qualitative environmental analysis[J].Analytical and Bioanalytical Chemistry,2015,407(21):6289-6299.
[22]林必桂,于云江,向明灯,等.基于气相/液相色谱-高分辨率质谱联用技术的非目标化合物分析方法研究进展[J].环境化学,2016,35(3):466-476.
[23]张丹,王彩虹,金滢,等.高效液相色谱-高分辨质谱法研究药物代谢产物的数据处理策略[J].质谱学报,2017,38(4):410-416.
[24]Saylor G L,Zhao C,Kupferle M J.Synergistic enhancement of oxidative degradation of atrazine using combined electrolysis and ozonation[J].Journal of Water Process Engineering,2018,21:154-162.
[25]Berberidou C,Kitsiou V,Kazala E,et al.Study of the decomposition and detoxification of the herbicidebentazon by heterogeneous photocatalysis:Kinetics,intermediates and transformation pathways[J].Applied Catalysis B:Environmental,2017,200:150-163.
[26]Jovic'a M,Manojlovic'D,Stankovic'D,et al.Degradation of triketone herbicides,mesotrione and sulcotrione,using advanced oxidation processes[J].Journal of Hazardous Materials,2013,260:1092-1099.
[27]张静,陈会明.邻苯二甲酸酯类增塑剂的危害及监管现状[J].现代化工,2011,31(12):1-6.
[28]Huang J Y,Li X F,Ma M J,et al.Removal of di-(2-ethylhexyl)phthalate from aqueous solution by UV/peroxymonosulfate:Influencing factors and reaction pathways[J].Chemical Engineering Journal,2017,314:182-191.
[29]Xu L J,Chu W,Graham N.Sonophotolytic degradation of phthalate acid esters in water and wastewater:Influence of compound properties and degradation mechanisms[J].Journal of Hazardous Materials,2015,288:43-50.
[30]Xu L J,Chu W,Graham N.A systematic study of the degradation of dimethyl phthalate using a high-frequency ultrasonic process[J].Ultrasonics Sonochemistry,2013,20(3):892-899.
[31]Qiao M,Ying G G,Singer A C,et al.Review of antibiotic resistance in China and its environment[J].Environment International,2018,110:160-172.
[32]Jin Q Q,Wang H B,Hu C,et al.Effects of NOM on the degradation of chloramphenicol by UV/H2O2and the characteristics of degradation products[J].Separation and Purification Technology,2018,191:108-115.
[33]Wang F G,Wang W J,Yuan S J,et al.Comparison of UV/H2O2and UV/PS processes for the degradation of thiamphenicol in aqueous solution[J].Journal of Photochemistry and Photobiology A:Chemistry,2017,348:79-88.
[34]Liu Y Q,He X X,Duan X D,et al.Significant role of UV and carbonate radical on the degradation of oxytetracycline in UV-AOPs:Kinetics and mechanism[J].Water Research,2016,95:195-204.
[35]Krasner S W,Mitch W A,McCurry D L,et al.Formation,precursors,control,and occurrence of nitrosamines in drinking water:A review[J].Water Research,2013,47:4433-4450.
[36]Gerrity D,Pisarenko A N,Marti E,et al.Nitrosamines in pilotscale and full-scale wastewater treatment plants with ozonation[J].Water Research,2015,72:251-261.
[37]Lee J H,Oh J E.A comprehensive survey on the occurrence and fate of nitrosamines in sewage treatment plants and water environment[J].Science of the Total Environment,2016,556:330-337.
[38]Krauss M,Longrée P,Dorusch F,et al.Occurrence and removal of N-nitrosamines in wastewater treatment plants[J].Water Research,2009,43:4381-4391.
[39]Wang W F,Yu J W,Ana W,et al.Occurrence and profiling of multiple nitrosamines in source water and drinking water of China[J].Science of the Total Environment,2016,551/552:489-495.
[40]Wu Q H,Shi H L,Ma Y F,et al.Determination of secondary and tertiary aminesas N-nitrosamine precursors in drinking water system using ultra-fast liquid chromatography-tandem mass spectrometry[J].Talanta,2015,131:736-741.
[41]Gao Y,Wang F F,Wu Y,et al.Comparison of degradation mechanisms of microcystin-LR using nanoscale zero-valent iron(nZVI)and bimetallic Fe/Ni and Fe/Pd nanoparticles[J].Chemical Engineering Journal,2016,285:459-466.
[42]He X X,Cruz A A,Hiskia A,et al.Destruction of microcystins(cyanotoxins)by UV-254nm-based direct photolysis and advanced oxidation processes(AOPs):Influence of variable amino acids on the degradation kinetics and reaction mechanisms[J].Water Research,2015,74:227-238.
[43]Karci A,Wurtzler E M,Cruz A A,et al.Solar photo-Fenton treatment of microcystin-LR in aqueous environment:Transformation products and toxicity in different water matrices[J].Journal of Hazardous Materials,2018,349:282-292.
[44]Jeong B,Oh M S,Park H M,et al.Elimination of microcystinLR and residual Mn species using permanganate and powdered activated carbon:Oxidation products and pathways[J].Water Research,2017,114:189-199.
[2]Rousis N I,Bade R,Bijlsma L,et al.Monitoring a large number of pesticides and transformation products in water samples from Spain and Italy[J].Environmental Research,2017,156:31-38.
[3]张瑞娟,姚宇霞,党晋华,等.加速溶剂萃取-固相萃取净化-气相色谱法测定土壤中17种有机氯农药[J].安全与环境工程,2017,24(4):74-78.
[4]陈文婷,向发椿,徐健蓉,等.高效液相色谱法测定水和土壤中氟唑菌酰胺残留[J].农药,2017,56(5):351-353.
[5]Li Z G,Qian Z Y,Hu S Y,et al.Molecularly imprinted solid phase extraction coupled with gas chromatography-mass spectrometry for determination of N-Nitrosodiphenylamine in water samples[J].Chemosphere,2018,212:872-880.
[6]吴春英,白鹭,谷风,等.超高效液相色谱-串联质谱法同时检测水中16种芳氧苯氧丙酸酯类除草剂[J].安全与环境工程,2016,23(5):97-101.
[7]Fu Y Q,Zhao C X,Lu X,et al.Nontargeted screening of chemical contaminants and illegal additives in food based on liquid chromatography-high resolution mass spectrometry[J].Trends in Analytical Chemistry,2017,96:89-98.
[8]Agüera A,Piernas A B M,Ma1as M C C.Analytical strategies used in HRMS[M]//Applications in High Resolution Mass Spectrometry:Food Safety and Pesticide Residue Analysis.Amstedam:Elsevier,2017.
[9]李明,马家辰,李红梅,等.静电场轨道阱质谱的进展[J].质谱学报,2013,34(3):185-192.
[10]Makarov A,Scigelova M.Coupling liquid chromatography to orbitrap mass spectrometry[J].Journal of Chromatography A,2010,1217:3938-3945.
[11]Rivera Z H,Oosterink E,Rietveld L,et al.Influence of natural organic matter on the screening of pharmaceuticals in water by using liquid chromatography with full scan mass spectrometry[J].Analytica Chimica Acta,2011,700(1/2):114-125.
[12]Meng X S,Bai H,Guo T,et al.Broad screening of illicit ingredients in cosmetics using ultra-high-performance liquid chromatography-hybrid quadrupole-Orbitrap mass spectrometry with customized accurate-mass database and mass spectral library[J].Journal of Chromatography A,2017,1528:61-74.
[13]Mao J F,Zheng N,Wen F,et al.Multi-mycotoxins analysis in raw milk by ultra high performance liquid chromatography coupled to quadrupole orbitrap mass spectrometry[J].Food Control,2018,84:305-311.
[14]Glicksberg L,Bryand K,Kerrigan S.Identification and quantification of synthetic cathinones in blood andurine using liquid chromatography-quadrupole/time of flight(LC-Q/TOF)mass spectrometry[J].Journal of Chromatography B,2016,1035:91-103.
[15]Kioussi M K,Lyris E M,Angelis Y S,et al.A generic screening methodology for horse doping control by LC-TOF-MS,GC-HRMS and GC-MS[J].Journal of Chromatography B,2013,941:69-80.
[16]Hisaindee S,Meetani M A,Rauf M A.Application of LC-MS to the analysis of advanced oxidation process(AOP)degradation of dye products and reaction mechanisms[J].Trends in Analytical Chemistry,2013,49:31-44.
[17]Kaufmann A,Butcher P,Maden K,et al.Quantitative and confirmative performance of liquid chromatography coupled to highresolution mass spectrometry compared to tandem mass spectrometry[J].Rapid Communication in Mass Spectrometry,2011,25(7):979-992.
[18]Deeb A A,Stephan S,Schmitz J,et al.Suspect screening of micropollutants and their transformation products in advanced wastewater treatment[J].Science of the Total Environment,2017,601/602:1247-1253.
[19]王丽,俞心愉,李磊.超高效液相色谱-高分辨质谱法快速检测白酒中4种甜味剂[J].中国卫生检验杂志,2014,24(22):3244-3246.
[20]Park N,Choi Y,Kim D,et al.Prioritization of highly exposable pharmaceuticals via a suspect/non-target screening approach:Acase study for Yeongsan River,Korea[J].Science of the Total Environment,2018,639(11):570-579.
[21]Ace1al J,Stampachiacchiere S,Pérez S,et al.Advances in liquid chromatography-high-resolution mass spectrometry for quantitative and qualitative environmental analysis[J].Analytical and Bioanalytical Chemistry,2015,407(21):6289-6299.
[22]林必桂,于云江,向明灯,等.基于气相/液相色谱-高分辨率质谱联用技术的非目标化合物分析方法研究进展[J].环境化学,2016,35(3):466-476.
[23]张丹,王彩虹,金滢,等.高效液相色谱-高分辨质谱法研究药物代谢产物的数据处理策略[J].质谱学报,2017,38(4):410-416.
[24]Saylor G L,Zhao C,Kupferle M J.Synergistic enhancement of oxidative degradation of atrazine using combined electrolysis and ozonation[J].Journal of Water Process Engineering,2018,21:154-162.
[25]Berberidou C,Kitsiou V,Kazala E,et al.Study of the decomposition and detoxification of the herbicidebentazon by heterogeneous photocatalysis:Kinetics,intermediates and transformation pathways[J].Applied Catalysis B:Environmental,2017,200:150-163.
[26]Jovic'a M,Manojlovic'D,Stankovic'D,et al.Degradation of triketone herbicides,mesotrione and sulcotrione,using advanced oxidation processes[J].Journal of Hazardous Materials,2013,260:1092-1099.
[27]张静,陈会明.邻苯二甲酸酯类增塑剂的危害及监管现状[J].现代化工,2011,31(12):1-6.
[28]Huang J Y,Li X F,Ma M J,et al.Removal of di-(2-ethylhexyl)phthalate from aqueous solution by UV/peroxymonosulfate:Influencing factors and reaction pathways[J].Chemical Engineering Journal,2017,314:182-191.
[29]Xu L J,Chu W,Graham N.Sonophotolytic degradation of phthalate acid esters in water and wastewater:Influence of compound properties and degradation mechanisms[J].Journal of Hazardous Materials,2015,288:43-50.
[30]Xu L J,Chu W,Graham N.A systematic study of the degradation of dimethyl phthalate using a high-frequency ultrasonic process[J].Ultrasonics Sonochemistry,2013,20(3):892-899.
[31]Qiao M,Ying G G,Singer A C,et al.Review of antibiotic resistance in China and its environment[J].Environment International,2018,110:160-172.
[32]Jin Q Q,Wang H B,Hu C,et al.Effects of NOM on the degradation of chloramphenicol by UV/H2O2and the characteristics of degradation products[J].Separation and Purification Technology,2018,191:108-115.
[33]Wang F G,Wang W J,Yuan S J,et al.Comparison of UV/H2O2and UV/PS processes for the degradation of thiamphenicol in aqueous solution[J].Journal of Photochemistry and Photobiology A:Chemistry,2017,348:79-88.
[34]Liu Y Q,He X X,Duan X D,et al.Significant role of UV and carbonate radical on the degradation of oxytetracycline in UV-AOPs:Kinetics and mechanism[J].Water Research,2016,95:195-204.
[35]Krasner S W,Mitch W A,McCurry D L,et al.Formation,precursors,control,and occurrence of nitrosamines in drinking water:A review[J].Water Research,2013,47:4433-4450.
[36]Gerrity D,Pisarenko A N,Marti E,et al.Nitrosamines in pilotscale and full-scale wastewater treatment plants with ozonation[J].Water Research,2015,72:251-261.
[37]Lee J H,Oh J E.A comprehensive survey on the occurrence and fate of nitrosamines in sewage treatment plants and water environment[J].Science of the Total Environment,2016,556:330-337.
[38]Krauss M,Longrée P,Dorusch F,et al.Occurrence and removal of N-nitrosamines in wastewater treatment plants[J].Water Research,2009,43:4381-4391.
[39]Wang W F,Yu J W,Ana W,et al.Occurrence and profiling of multiple nitrosamines in source water and drinking water of China[J].Science of the Total Environment,2016,551/552:489-495.
[40]Wu Q H,Shi H L,Ma Y F,et al.Determination of secondary and tertiary aminesas N-nitrosamine precursors in drinking water system using ultra-fast liquid chromatography-tandem mass spectrometry[J].Talanta,2015,131:736-741.
[41]Gao Y,Wang F F,Wu Y,et al.Comparison of degradation mechanisms of microcystin-LR using nanoscale zero-valent iron(nZVI)and bimetallic Fe/Ni and Fe/Pd nanoparticles[J].Chemical Engineering Journal,2016,285:459-466.
[42]He X X,Cruz A A,Hiskia A,et al.Destruction of microcystins(cyanotoxins)by UV-254nm-based direct photolysis and advanced oxidation processes(AOPs):Influence of variable amino acids on the degradation kinetics and reaction mechanisms[J].Water Research,2015,74:227-238.
[43]Karci A,Wurtzler E M,Cruz A A,et al.Solar photo-Fenton treatment of microcystin-LR in aqueous environment:Transformation products and toxicity in different water matrices[J].Journal of Hazardous Materials,2018,349:282-292.
[44]Jeong B,Oh M S,Park H M,et al.Elimination of microcystinLR and residual Mn species using permanganate and powdered activated carbon:Oxidation products and pathways[J].Water Research,2017,114:189-199.
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