有机磷酸酯（OPEs）的环境污染特征、毒性和分析方法研究进展

廖梓聪; 李会茹; 杨愿愿; 胡立新; 应光国

doi:10.7524/j.issn.0254-6108.2020121601

[1]

VAN DER VEEN I, DE BOER J. Phosphorus flame retardants: Properties, production, environmental occurrence, toxicity and analysis [J]. Chemosphere, 2012, 88(10): 1119-1153. doi: 10.1016/j.chemosphere.2012.03.067

[2]

王晓伟, 刘景富, 阴永光. 有机磷酸酯阻燃剂污染现状与研究进展 [J]. 化学进展, 2010, 22(10): 1983-1992. WANG X W, LIU J F, YIN Y G. The pollution status and research progress on organophosphate ester flame retardants [J]. Progress in Chemistry, 2010, 22(10): 1983-1992(in Chinese).

[3]

欧育湘. 我国有机磷阻燃剂产业的分析与展望 [J]. 化工进展, 2011, 30(1): 210-215. OU Y X. Developments of organic phosphorus flame retardant industry in China. [J]. Chemical Industry and Engineering Progress, 2011, 30(1): 210-215(in Chinese).

[4]

ANNELI MARKLUND S, ULRIKA O, PETER H. Organophosphorus flame retardants and plasticizers in marine and fresh water biota and in human milk [J]. Journal of Environmental Monitoring, 2010, 12(4): 943-951. doi: 10.1039/b921910b

[5]

高小中, 许宜平, 王子健. 有机磷酸酯阻燃剂的环境暴露与迁移转化研究进展 [J]. 生态毒理学报, 2015, 10(2): 56-68. GAO X Z, XU Y P, WANG Z J. Progress in environment exposure, transport and transform of organophosphorus flame retardants. [J]. Asian Journal of Ecotoxicology, 2015, 10(2): 56-68(in Chinese).

[6]

CASTRO-JIMENEZ J, GONZALEZ-GAYA B, PIZARRO M, et al. Organophosphate ester flame retardants and plasticizers in the global oceanic atmosphere [J]. Environmental Science & Technology, 2016, 50(23): 12831-12839.

[7]

SALAMOVA A, HERMANSON M H, HITES R A. Organophosphate and halogenated flame retardants in atmospheric particles from a European Arctic site [J]. Environmental Science & Technology, 2014, 48(11): 6133-6140.

[8]

SUHRING R, DIAMOND M L, SCHERINGER M, et al. Organophosphate esters in Canadian arctic air: Occurrence, levels and trends [J]. Environmental Science & Technology, 2016, 50(14): 7409-7415.

[9]

MA Y, XIE Z, LOHMANN R, et al. Organophosphate ester flame retardants and plasticizers in ocean sediments from the North Pacific to the Arctic Ocean [J]. Environmental Science & Technology, 2017, 51(7): 3809-3815.

[10]

LI J, XIE Z, MI W, et al. Organophosphate esters in air, snow, and seawater in the North Atlantic and the Arctic [J]. Environmental Science & Technology, 2017, 51(12): 6887-6896.

[11]

王艺璇, 段玉双, 耿存珍. 有机磷酸酯在水环境中的残留及生态风险评价 [J]. 环境与健康杂志, 2015, 32(10): 935-939. WANG Y X, DUAN Y S, GENG C Z. Occurrence of organophosphate ester in aquatic environment and ecological risk assessment. [J]. Journal of Environment and Health, 2015, 32(10): 935-939(in Chinese).

[12]

刘佳. 有机磷酸酯阻燃剂污染现状及降解过程研究进展 [J]. 应用化工, 2018, 47(12): 2705-2710, 2714. doi: 10.3969/j.issn.1671-3206.2018.12.036 LIU J. Review of contamination status and degradation processes of organophosphate ester (OPE) flame retardants [J]. Applied Chemical Industry, 2018, 47(12): 2705-2710, 2714(in Chinese). doi: 10.3969/j.issn.1671-3206.2018.12.036

[13]

王雪松, 李志娟, 李青山, 等. 磷系阻燃剂的应用与展望 [J]. 化工时刊, 2001(6): 1-5. doi: 10.3969/j.issn.1002-154X.2001.06.001 WANG X S, LI Z J, LI Q S, et al. Application and prospect of phosphorus flame retardant [J]. Chemical Industry Times, 2001(6): 1-5(in Chinese). doi: 10.3969/j.issn.1002-154X.2001.06.001

[14]

ANDRESEN J A, GRUNDMANN A, BESTER K. Organophosphorus flame retardants and plasticisers in surface waters [J]. Science of the Total Environment, 2004, 332(1-3): 155-166. doi: 10.1016/j.scitotenv.2004.04.021

[15]

SCHREDER E D, LA GUARDIA M J. Flame retardant transfers from U. S. households (dust and laundry wastewater) to the aquatic environment [J]. Environmental Science & Technology, 2014, 48(19): 11575-11583.

[16]

CRISTALE J, GARCIA VAZQUEZ A, BARATA C, et al. Priority and emerging flame retardants in rivers: occurrence in water and sediment, daphnia magna toxicity and risk assessment [J]. Environment International, 2013, 59: 232-243. doi: 10.1016/j.envint.2013.06.011

[17]

李成辉, 张冬蕊, 李胜红, 等. 污水处理厂中有机磷酸酯的研究进展 [J]. 生态毒理学报, 2019, 14(6): 32-46. LI C H, ZHANG D R, LI S H, et al. A review on the occurrence of organophosphate esters in wastewater treatment plants [J]. Asian Journal of Ecotoxicology, 2019, 14(6): 32-46(in Chinese).

[18]

PANG L, YUAN Y, HE H, et al. Occurrence, distribution, and potential affecting factors of organophosphate flame retardants in sewage sludge of wastewater treatment plants in Henan Province, Central China [J]. Chemosphere, 2016, 152: 245-251. doi: 10.1016/j.chemosphere.2016.02.104

[19]

GAO L, SHI Y, LI W, et al. Occurrence and distribution of organophosphate triesters and diesters in sludge from sewage treatment plants of Beijing, China [J]. Science of the Total Environment, 2016, 544: 143-149. doi: 10.1016/j.scitotenv.2015.11.094

[20]

ZENG X, HE L, CAO S, et al. Occurrence and distribution of organophosphate flame retardants/plasticizers in wastewater treatment plant sludges from the Pearl River Delta, China [J]. Environmental Toxicology and Chemistry, 2014, 33(8): 1720-1725. doi: 10.1002/etc.2604

[21]

孙佳薇, 丁炜楠, 张占恩, 等. 污水处理厂中有机磷阻燃剂的污染特征 [J]. 环境科学, 2018, 39(5): 2230-2238. SUN J W, DING W N, ZHANG Z E, et al. Pollution characteristics of organophosphorus flame retardants in a wastewater treatment plant [J]. Environmental Science, 2018, 39(5): 2230-2238(in Chinese).

[22]

赵赛, 刘世龙, 张华, 等. 污水处理工艺对有机磷酸酯的去除效果 [J]. 中国给水排水, 2018, 34(5): 88-91. ZHAO S, LIU S L, ZHANG H, et al. Removal efficiency of organophosphate esters in wastewater treatment processes [J]. China Water & Wastewater, 2018, 34(5): 88-91(in Chinese).

[23]

XU L, HU Q, LIU J, et al. Occurrence of organophosphate esters and their diesters degradation products in industrial wastewater treatment plants in China: Implication for the usage and potential degradation during production processing [J]. Environment Pollution, 2019, 250: 559-566. doi: 10.1016/j.envpol.2019.04.058

[24]

WOUDNEH M B,BENSKIN J P,WANG J H,et al. Quantitative determination of 13 organophosphorous flame retardants and plasticizers in a wastewater treatment system by high performance liquid chromatography tandem mass spectrometry [J]. Journal of Chromatography A, 2015, 1400(26): 149-155.

[25]

KIM U J, OH J K, KANNAN K. Occurrence, removal, and environmental emission of organophosphate flame retardants/plasticizers in a wastewater treatment plant in New York State [J]. Environmental Science & Technology, 2017, 51(14): 7872-7880.

[26]

WANG R, TANG J, XIE Z, et al. Occurrence and spatial distribution of organophosphate ester flame retardants and plasticizers in 40 rivers draining into the Bohai Sea, north China [J]. Environment Pollution, 2015, 198: 172-178. doi: 10.1016/j.envpol.2014.12.037

[27]

陈玫宏, 徐怀洲, 宋宁慧, 等. 高效液相色谱-串联质谱法同时测定水体和沉积物中12种有机磷酸酯类化合物 [J]. 分析化学, 2017, 45(7): 987-995. doi: 10.11895/j.issn.0253-3820.170180 CHEN M H, XU H Z, SONG N H, et al. Simultaneous determination of 12 kinds of organophosphates in water and sediment by high performance liquid chromatography-tandem mass spectrometry [J]. Chinese Journal of Analytical Chemistry, 2017, 45(7): 987-995(in Chinese). doi: 10.11895/j.issn.0253-3820.170180

[28]

LIU Y, SONG N, GUO R, et al. Occurrence and partitioning behavior of organophosphate esters in surface water and sediment of a shallow Chinese freshwater lake (Taihu Lake): Implication for eco-toxicity risk [J]. Chemosphere, 2018, 202: 255-263. doi: 10.1016/j.chemosphere.2018.03.108

[29]

吴迪, 印红玲, 李世平, 等. 成都市锦江表层水和沉积物中有机磷酸酯的污染特征 [J]. 环境科学, 2019, 40(3): 1245-1251. WU D, YIN H L, LI S P, et al. Pollution characteristics of OPEs in the surface water and sediment of the Jinjiang River in Chengdu City [J]. Environmental Science, 2019, 40(3): 1245-1251(in Chinese).

[30]

刘静, 何丽雄, 曾祥英, 等. 珠江主干和东江河流表层沉积物中有机磷酸酯阻燃剂/增塑剂分布 [J]. 生态毒理学报, 2016, 11(2): 436-443. LIU J, HE L X, ZENG X Y, et al. Occurrence and distribution of organophosphorus flame retardants/plasticizer in surface sediments from the Pearl River and Dongjiang River [J]. Asian Journal of Ecotoxicology, 2016, 11(2): 436-443(in Chinese).

[31]

TAN X X, LUO X J, ZHENG X B, et al. Distribution of organophosphorus flame retardants in sediments from the Pearl River Delta in South China [J]. Science of the Total Environment, 2016, 544: 77-84. doi: 10.1016/j.scitotenv.2015.11.089

[32]

ZENG X, XU L, LIU J, et al. Occurrence and distribution of organophosphorus flame retardants/plasticizers and synthetic musks in sediments from source water in the Pearl River Delta, China [J]. Environmental Toxicology and Chemistry, 2018, 37(4): 975-982. doi: 10.1002/etc.4040

[33]

SHI Y, ZHANG Y, DU Y, et al. Occurrence, composition and biological risk of organophosphate esters (OPEs) in water of the Pearl River Estuary, South China [J]. Environmental Science and Pollution Research, 2020, 27(13): 14852-14862. doi: 10.1007/s11356-020-08001-1

[34]

KIM U J, KANNAN K. Occurrence and distribution of organophosphate flame retardants/plasticizers in surface waters, tap water, and rainwater: Implications for human exposure [J]. Environmental Science & Technology, 2018, 52(10): 5625-5633.

[35]

WOLSCHKE H, SUHRING R, XIE Z, et al. Organophosphorus flame retardants and plasticizers in the aquatic environment: A case study of the Elbe River, Germany [J]. Environment Pollution, 2015, 206: 488-493. doi: 10.1016/j.envpol.2015.08.002

[36]

LI J, YU N, ZHANG B, et al. Occurrence of organophosphate flame retardants in drinking water from China [J]. Water Research, 2014, 54: 53-61. doi: 10.1016/j.watres.2014.01.031

[37]

朱孔睿. 水中有机磷酸酯阻燃剂分析方法的建立及在不同饮用水处理工艺中的去除研究[D]. 重庆: 重庆大学, 2017. ZHU K R. Establishment of analytical method for organophosphate flame retardant in water and its removal in different drinking water treatment processes[D]. Chongqing: Chongqing University, 2017 （in Chinese）.

[38]

CRISTALE J, QUINTANA J, CHALER R, et al. Gas chromatography/mass spectrometry comprehensive analysis of organophosphorus, brominated flame retardants, by-products and formulation intermediates in water [J]. Journal of Chromatography A, 2012, 1241: 1-12. doi: 10.1016/j.chroma.2012.04.013

[39]

ZENG Y, DING N, WANG T, et al. Organophosphate esters (OPEs) in fine particulate matter (PM_2.5) in urban, e-waste, and background regions of south China [J]. Journal of Hazardous Materials, 2020, 385: 121583. doi: 10.1016/j.jhazmat.2019.121583

[40]

WANG T, DING N, WANG T, et al. Organophosphorus esters (OPEs) in PM_2.5 in urban and e-waste recycling regions in southern China: Concentrations, sources, and emissions [J]. Environmental Research, 2018, 167: 437-444. doi: 10.1016/j.envres.2018.08.015

[41]

LIANG Y, WANG H, YANG Q, et al. Spatial distribution and seasonal variations of atmospheric organophosphate esters (OPEs) in Tianjin, China based on gridded field observations [J]. Environment Pollution, 2020, 263: 114460. doi: 10.1016/j.envpol.2020.114460

[42]

LI J, TANG J, MI W, et al. Spatial distribution and seasonal variation of organophosphate esters in air above the Bohai and Yellow Seas, China [J]. Environmental Science & Technology, 2018, 52(1): 89-97.

[43]

NA G, HOU C, LI R, et al. Occurrence, distribution, air-seawater exchange and atmospheric deposition of organophosphate esters (OPEs) from the Northwestern Pacific to the Arctic Ocean [J]. Marine Pollution Bulletin, 2020, 157: 111243. doi: 10.1016/j.marpolbul.2020.111243

[44]

侯超. 极地大气有机磷酸酯介质分配机制研究[D]. 上海: 上海海洋大学, 2020. HOU C. Research on the medium partitioning mechanism of atmospheric organophosphate esters in polar regions[D]. Shanghai: Shanghai Ocean University, 2020（in Chinese）.

[45]

SALAMOVA A, MA Y, VENIER M, et al. High levels of organophosphate flame retardants in the Great Lakes atmosphere [J]. Environmental Science & Technology Letters, 2013, 1(1): 8-14.

[46]

WU Y, VENIER M, SALAMOVA A. Spatioseasonal variations and partitioning behavior of organophosphate esters in the Great Lakes atmosphere [J]. Environmental Science & Technology, 2020, 54(9): 5400-5408.

[47]

房晓静, 杨圣文, 张洪海, 等. 海洋及其上空大气中有机磷酸酯的研究进展 [J]. 海洋科学, 2020, 44(9): 154-165. FANG X J, YANG S W, ZHANG H H, et al. Review of organophosphate esters in oceans and atmospheres [J]. Marine Sciences, 2020, 44(9): 154-165(in Chinese).

[48]

CASTRO-JIMENEZ J, BERROJALBIZ N, PIZARRO M, et al. Organophosphate ester (OPE) flame retardants and plasticizers in the open Mediterranean and Black Seas atmosphere [J]. Environmental Science & Technology, 2014, 48(6): 3203-3209.

[49]

CASTRO-JIMÉNEZ J, SEMPéRé R. Atmospheric particle-bound organophosphate ester flame retardants and plasticizers in a North African Mediterranean coastal city (Bizerte, Tunisia) [J]. Science of the Total Environment, 2018, 642: 383-393. doi: 10.1016/j.scitotenv.2018.06.010

[50]

MOLLER A, STURM R, XIE Z, et al. Organophosphorus flame retardants and plasticizers in airborne particles over the Northern Pacific and Indian Ocean toward the Polar Regions: Evidence for global occurrence [J]. Environmental Science & Technology, 2012, 46(6): 3127-3134.

[51]

CHENG W, XIE Z, BLAIS J M, et al. Organophosphorus esters in the oceans and possible relation with ocean gyres [J]. Environment Pollution, 2013, 180: 159-164. doi: 10.1016/j.envpol.2013.05.032

[52]

WANG C, WANG P, ZHAO J, et al. Atmospheric organophosphate esters in the Western Antarctic Peninsula over 2014-2018: Occurrence, temporal trend and source implication [J]. Environment Pollution, 2020, 267: 115428. doi: 10.1016/j.envpol.2020.115428

[53]

HE C T, ZHENG J, QIAO L, et al. Occurrence of organophosphorus flame retardants in indoor dust in multiple microenvironments of southern China and implications for human exposure [J]. Chemosphere, 2015, 133: 47-52. doi: 10.1016/j.chemosphere.2015.03.043

[54]

CHRISTIA C, TANG B, YIN S S, et al. Simultaneous determination of legacy and emerging organophosphorus flame retardants and plasticizers in indoor dust using liquid and gas chromatography–tandem mass spectrometry: method development, validation, and application [J]. Analytical and Bioanalytical Chemistry, 2019, 411(26): 7015-7025. doi: 10.1007/s00216-019-02078-5

[55]

WANG L, JIA Y, KANG Q, et al. Nontarget discovery of 11 aryl organophosphate triesters in house dust using high-resolution mass spectrometry [J]. Environmental Science & Technology, 2020, 54(18): 11376-11385.

[56]

DU B, SHEN M, CHEN H, et al. Beyond traditional organophosphate triesters: Prevalence of emerging organophosphate triesters and organophosphate diesters in indoor dust from a mega e-waste recycling industrial park in south China[J]. Environmental Science & Technology, 2020, 54(19): 12001.

[57]

TAN H, YANG L, YU Y, et al. Co-existence of organophosphate di- and tri-esters in house dust from south China and midwestern United States: Implications for human exposure [J]. Environmental Science & Technology, 2019, 53(9): 4784-4793.

[58]

FANG M, WEBSTER T F, GOODEN D, et al. Investigating a novel flame retardant known as V6: Measurements in baby products, house dust, and car dust [J]. Environmental Science & Technology, 2013, 47(9): 4449-4454.

[59]

CEQUIER E, IONAS A C, COVACI A, et al. Occurrence of a broad range of legacy and emerging flame retardants in indoor environments in Norway [J]. Environmental Science & Technology, 2014, 48(12): 6827-6835.

[60]

BRANDSMA S H, DE BOER J, VAN VELZEN M J, et al. Organophosphorus flame retardants (PFRs) and plasticizers in house and car dust and the influence of electronic equipment [J]. Chemosphere, 2014, 116: 3-9. doi: 10.1016/j.chemosphere.2014.02.036

[61]

ABDALLAH M A, COVACI A. Organophosphate flame retardants in indoor dust from Egypt: implications for human exposure [J]. Environmental Science & Technology, 2014, 48(9): 4782-4789.

[62]

温家欣. 有机磷酸酯阻燃剂的分离分析技术及其应用研究[D]. 广州: 中山大学, 2010. WEN J X. Separation and analysis of organophosphate flame retardant and its application[D]. Guangzhou: Sun Yat-sen University, 2010 .

[63]

CUI K, WEN J, ZENG F, et al. Occurrence and distribution of organophosphate esters in urban soils of the subtropical city, Guangzhou, China [J]. Chemosphere, 2017, 175: 514-520. doi: 10.1016/j.chemosphere.2017.02.070

[64]

印红玲, 李世平, 叶芝祥, 等. 成都市土壤中有机磷阻燃剂的污染特征及来源分析 [J]. 环境科学学报, 2016, 36(2): 606-613. YIN H L, LI S P, YE Z X, et al. Pollution characteristics and sources of OPEs in the soil of Chengdu City [J]. Acta Scientiae Circumstantiae, 2016, 36(2): 606-613(in Chinese).

[65]

HE J, LI J, MA L, et al. Large-scale distribution of organophosphate esters (flame retardants and plasticizers) in soil from residential area across China: Implications for current level [J]. Science of the Total Environment, 2019, 697: 133997. doi: 10.1016/j.scitotenv.2019.133997

[66]

WANG Y, YAO Y, LI W, et al. A nationwide survey of 19 organophosphate esters in soils from China: Spatial distribution and hazard assessment [J]. Science of the Total Environment, 2019, 671: 528-535. doi: 10.1016/j.scitotenv.2019.03.335

[67]

ELKE F, IVANA M. Pollution of soils with organophosphorus flame retardants and plasticizers [J]. Journal of Environmental Monitoring, 2011, 13(10): 2692-2694. doi: 10.1039/c1em10538h

[68]

KURT-KARAKUS P, ALEGRIA H, BIRGUL A, et al. Organophosphate ester (OPEs) flame retardants and plasticizers in air and soil from a highly industrialized city in Turkey [J]. Science of the Total Environment, 2018, 625: 555-565. doi: 10.1016/j.scitotenv.2017.12.307

[69]

YADAV I C, DEVI N L, LI J, et al. Concentration and spatial distribution of organophosphate esters in the soil-sediment profile of Kathmandu Valley, Nepal: Implication for risk assessment [J]. Science of the Total Environment, 2018, 613-614: 502-512. doi: 10.1016/j.scitotenv.2017.09.039

[70]

WAN W, ZHANG S, HUANG H, et al. Occurrence and distribution of organophosphorus esters in soils and wheat plants in a plastic waste treatment area in China [J]. Environment Pollution, 2016, 214: 349-353. doi: 10.1016/j.envpol.2016.04.038

[71]

PANG L, LIU J, YIN Y, et al. Evaluating the sorption of organophosphate esters to different sourced humic acids and its effects on the toxicity to Daphnia magna [J]. Environmental Toxicology and Chemistry, 2013, 32(12): 2755-2761. doi: 10.1002/etc.2360

[72]

SANTIN G, ELJARRAT E, BARCELO D. Simultaneous determination of 16 organophosphorus flame retardants and plasticizers in fish by liquid chromatography-tandem mass spectrometry [J]. Journal of Chromatography A, 2016, 1441: 34-43. doi: 10.1016/j.chroma.2016.02.058

[73]

索莉莉, 朱群英, 胡美华. 超声辅助萃取-液相色谱-串联质谱法同时检测水产品中11种有机磷酸酯类阻燃剂 [J]. 食品工业科技, 2018, 39(6): 210-216. SUO L L, ZHU Q Y, HU M H, et al. Simultaneous determination of 11 organophosphate esters in aquatic product by ultrasound-assisted extraction coupled with LC-MS/MS [J]. Science and Technology of Food Industry, 2018, 39(6): 210-216(in Chinese).

[74]

BEKELE T G, ZHAO H, WANG Q, et al. Bioaccumulation and trophic transfer of emerging organophosphate flame retardants in the marine food webs of Laizhou Bay, north China [J]. Environmental Science & Technology, 2019, 53(22): 13417-13426.

[75]

GREAVES A K, LETCHER R J. Comparative body compartment composition and in ovo transfer of organophosphate flame retardants in North American Great Lakes herring gulls [J]. Environmental Science & Technology, 2014, 48(14): 7942-7950.

[76]

LU Z, MARTIN P A, BURGESS N M, et al. Volatile methylsiloxanes and organophosphate esters in the eggs of European starlings (Sturnus vulgaris) and congeneric gull species from locations across Canada [J]. Environmental Science & Technology, 2017, 51(17): 9836-9845.

[77]

FERNIE K J, PALACE V, PETERS L E, et al. Investigating endocrine and physiological parameters of captive American kestrels exposed by diet to selected organophosphate flame retardants [J]. Environmental Science & Technology, 2015, 49(12): 7448-7455.

[78]

LIU Q, WANG X, YANG R, et al. Uptake kinetics, accumulation, and long-distance transport of organophosphate esters in plants: Impacts of chemical and plant properties [J]. Environmental Science & Technology, 2019, 53(9): 4940-4947.

[79]

TAN H, CHEN D, PENG C, et al. Novel and Traditional organophosphate esters in house dust from South China: Association with hand wipes and exposure estimation[J]. Environmental Science & Technology. 2018, 52(19): 11017-11026.

[80]

符元证, 史亚利, 逯晓波, 等. 有机磷酸酯阻燃剂暴露的毒性效应及生物标志物研究进展 [J]. 中华预防医学杂志, 2020, 54(10): 1152-1160. FU Y Z, SHI Y L, L X B, et al. Research progress on toxic effects and biomarkers of organophosphate ester flame retartant exposure [J]. Chinese Journal of Preventive Medicine, 2020, 54(10): 1152-1160(in Chinese).

[81]

LI P, ZENG X Y, CUI J T, et al. Determination of seven urinary metabolites of organophosphate esters using liquid chromatography-tandem mass spectrometry [J]. Chinese Journal of Analytical Chemistry, 2017, 45(11): 1648-1654. doi: 10.1016/S1872-2040(17)61048-X

[82]

CEQUIER E, MARCE R M, BECHER G, et al. A high-throughput method for determination of metabolites of organophosphate flame retardants in urine by ultra performance liquid chromatography-high resolution mass spectrometry [J]. Analytica Chimica Acta, 2014, 845: 98-104. doi: 10.1016/j.aca.2014.06.026

[83]

CRAIG J A, CEBALLOS D M, FRUH V, et al. Exposure of nail salon workers to phthalates, di(2-ethylhexyl) terephthalate, and organophosphate esters: A pilot study [J]. Environmental Science & Technology, 2019, 53(24): 14630-14637.

[84]

HOFFMAN K, BUTT C M, WEBSTER T F, et al. Temporal trends in exposure to organophosphate flame retardants in the United States [J]. Environmental Science & Technology Letters, 2017, 4(3): 112-118.

[85]

LIU L Y, HE K, HITES R A, et al. Hair and nails as noninvasive biomarkers of human exposure to brominated and organophosphate flame retardants [J]. Environmental Science & Technology, 2016, 50(6): 3065-3073.

[86]

KIM J W, ISOBE T, MUTO M, et al. Organophosphorus flame retardants (PFRs) in human breast milk from several Asian countries [J]. Chemosphere, 2014, 116: 91-97. doi: 10.1016/j.chemosphere.2014.02.033

[87]

孙敦宇, 杨绍贵, 向伟铭, 等. 有机磷酸酯阻燃剂降解方法的研究进展 [J]. 环境化学, 2021, 40(2): 474-486. doi: 10.7524/j.issn.0254-6108.2020051603 SUN D Y, YANG S G, XIANG W M, et al. Research progress on degradation methods of organophosphorus flame retardants [J]. Environmental Chemistry, 2021, 40(2): 474-486(in Chinese). doi: 10.7524/j.issn.0254-6108.2020051603

[88]

FANG Y, KIM E, STRATHMANN T J. Mineral- and base-catalyzed hydrolysis of organophosphate flame retardants: Potential major fate-controlling sink in soil and aquatic environments [J]. Environmental Science & Technology, 2018, 52(4): 1997.

[89]

SU G, LETCHER R J, YU H. Organophosphate flame retardants and plasticizers in aqueous solution: pH-dependent hydrolysis, kinetics, and pathways [J]. Environmental Science & Technology, 2016, 50(15): 8103-8111.

[90]

庞龙, 张肖静, 庞榕, 等. 城市污水处理工艺对有机磷酸酯类化合物的去除 [J]. 河南师范大学学报(自然科学版), 2016, 44(3): 98-103. PANG L, ZHANG X J, PANG R, et al. Removal of organophosphate esters in municipal wastewater treatment process [J]. Journal of Henan Normal University(Natural Science Edition), 2016, 44(3): 98-103(in Chinese).

[91]

CRISTALE J, DANTAS R F, DE LUCA A, et al. Role of oxygen and DOM in sunlight induced photodegradation of organophosphorous flame retardants in river water [J]. Journal of Hazardous Materials, 2017, 323: 242-249. doi: 10.1016/j.jhazmat.2016.05.019

[92]

SUN S, JIANG J, ZHAO H, et al. Photochemical reaction of tricresyl phosphate (TCP) in aqueous solution: Influencing factors and photolysis products [J]. Chemosphere, 2020, 241: 124971. doi: 10.1016/j.chemosphere.2019.124971

[93]

KULKARNI S V, MARKAD V L, MELO J S, et al. Biodegradation of tributyl phosphate using Klebsiella pneumoniae sp. S3 [J]. Applied Microbiology and Biotechnology, 2013, 98(2): 919-929.

[94]

LIU J, LIN H, DONG Y, et al. Elucidating the biodegradation mechanism of tributyl phosphate (TBP) by Sphingomonas sp. isolated from TBP-contaminated mine tailings [J]. Environment Pollution, 2019, 250: 284-291. doi: 10.1016/j.envpol.2019.03.127

[95]

卫昆. 磷酸三苯酯的微生物降解机制及其降解产物毒性研究[D]. 广州: 华南理工大学, 2018. WEI K. Biodegradation mechanism of triphenyl phosphate and toxicity of its metabolites[D]. Guangzhou: South China University of Technology, 2018（in Chinese）.

[96]

JURGENS S S, HELMUS R, WAAIJERS S L, et al. Mineralisation and primary biodegradation of aromatic organophosphorus flame retardants in activated sludge [J]. Chemosphere, 2014, 111: 238-242. doi: 10.1016/j.chemosphere.2014.04.016

[97]

LIU Y, YIN H, WEI K, et al. Biodegradation of tricresyl phosphate isomers by Brevibacillus brevis: Degradation pathway and metabolic mechanism [J]. Chemosphere, 2019, 232: 195-203. doi: 10.1016/j.chemosphere.2019.05.188

[98]

SHOUJI T, IKUKO S, ISAO K, et al. Isolation and identification of persistent chlorinated organophosphorus flame retardant-degrading bacteria [J]. Applied and Environmental Microbiology, 2010, 76(15): 5292-5296. doi: 10.1128/AEM.00506-10

[99]

TAKAHASHI S, MIURA K, ABE K, et al. Complete detoxification of tris(2-chloroethyl) phosphate by two bacterial strains: Sphingobium sp. strain TCM1 and Xanthobacter autotrophicus strain GJ10 [J]. Journal of Bioscience and Bioengineering, 2012, 114(3): 306-311. doi: 10.1016/j.jbiosc.2012.04.010

[100]

TAKAHASHI S, OBANA Y, OKADA S, et al. Complete detoxification of tris(1, 3-dichloro-2-propyl) phosphate by mixed two bacteria, Sphingobium sp. strain TCM1 and Arthrobacter sp. strain PY1 [J]. Journal of Bioscience and Bioengineering, 2012, 113(1): 79-83. doi: 10.1016/j.jbiosc.2011.08.020

[101]

HOU R, XU Y, WANG Z. Review of OPFRs in animals and humans: Absorption, bioaccumulation, metabolism, and internal exposure research [J]. Chemosphere, 2016, 153: 78-90. doi: 10.1016/j.chemosphere.2016.03.003

[102]

REEMTSMA T, LINGOTT J, ROEGLER S. Determination of 14 monoalkyl phosphates, dialkyl phosphates and dialkyl thiophosphates by LC-MS/MS in human urinary samples [J]. Science of the Total Environment, 2011, 409(10): 1990-1993. doi: 10.1016/j.scitotenv.2011.01.032

[103]

汪国威. 有机磷酸酯阻燃剂在鱼体内的富集、分布和代谢及其机制[D]. 南京: 南京大学, 2017. WANG G W. Accumulation, distribution and transformation of organophosphate flame retardants in fish and their underlying mechanism[D]. Nanjing: Nanjing University, 2017（in Chinese）.

[104]

杜仲坤. 常用有机磷酸酯阻燃剂对斑马鱼发育及肝脏代谢的影响[D]. 南京: 南京大学, 2016. DU Z K. Effects of organophosphate flame retardants on zebrafish embryo development and liver metabolism[D]. Nanjing: Nanjing University, 2016（in Chinese）.

[105]

VAN DEN EEDE N, ERRATICO C, EXARCHOU V, et al. In vitro biotransformation of tris(2-butoxyethyl) phosphate (TBOEP) in human liver and serum [J]. Toxicology and Applied Pharmacology, 2015, 284(2): 246-253. doi: 10.1016/j.taap.2015.01.021

[106]

VAN DEN EEDE N, MAHO W, ERRATICO C, et al. First insights in the metabolism of phosphate flame retardants and plasticizers using human liver fractions [J]. Toxicology Letters, 2013, 223(1): 9-15. doi: 10.1016/j.toxlet.2013.08.012

[107]

GREAVES A K, SU G, LETCHER R J. Environmentally relevant organophosphate triesters in herring gulls: In vitro biotransformation and kinetics and diester metabolite formation using a hepatic microsomal assay [J]. Toxicology and Applied Pharmacology, 2016, 308: 59-65. doi: 10.1016/j.taap.2016.08.007

[108]

HAN X, HAO Y, LI Y, et al. Occurrence and distribution of organophosphate esters in the air and soils of Ny-Alesund and London Island, Svalbard, Arctic[J]. Environment Pollution, 2020, 263(Pt A): 114495.

[109]

徐怀洲, 王智志, 张圣虎, 等. 有机磷酸酯类阻燃剂毒性效应研究进展 [J]. 生态毒理学报, 2018, 13(3): 19-30. doi: 10.7524/AJE.1673-5897.20170601001 XU H Z, WANG Z Z, ZHANG S H, et al. Research progress on toxicity effects of organophosphate flame retardants [J]. Asian Journal of Ecotoxicology, 2018, 13(3): 19-30(in Chinese). doi: 10.7524/AJE.1673-5897.20170601001

[110]

HOFFMAN K, DANIELS J L, STAPLETON H M. Urinary metabolites of organophosphate flame retardants and their variability in pregnant women [J]. Environment International, 2014, 63: 169-172. doi: 10.1016/j.envint.2013.11.013

[111]

LI J, ZHAO L, LETCHER R J, et al. A review on organophosphate Ester (OPE) flame retardants and plasticizers in foodstuffs: Levels, distribution, human dietary exposure, and future directions [J]. Environment International, 2019, 127: 35-51. doi: 10.1016/j.envint.2019.03.009

[112]

YANG J, ZHAO Y, LI M, et al. A review of a class of emerging contaminants: the classification, distribution, intensity of consumption, synthesis routes, environmental effects and expectation of pollution abatement to organophosphate flame retardants (OPFRs) [J]. International Journal of Molecular Sciences, 2019, 20(12): 2874. doi: 10.3390/ijms20122874

[113]

单岳, 王诗雨, 谷雷严, 等. 有机磷酸酯暴露水平与毒性效应的研究进展 [J]. 环境科学与管理, 2019, 44(6): 15-18. doi: 10.3969/j.issn.1673-1212.2019.06.004 SHAN Y, WANG S Y, GU L Y, et al. Research progress on exposure levels and toxic effects of organophosphates [J]. Environmental Science and Management, 2019, 44(6): 15-18(in Chinese). doi: 10.3969/j.issn.1673-1212.2019.06.004

[114]

FARHAT A, CRUMP D, CHIU S, et al. In Ovo effects of two organophosphate flame retardants-TCPP and TDCPP-on pipping success, development, mRNA expression, and thyroid hormone levels in chicken embryos [J]. Toxicological Sciences, 2013, 134(1): 92-102. doi: 10.1093/toxsci/kft100

[115]

ZHU Y, MA X, SU G, et al. Environmentally relevant concentrations of the flame retardant tris(1, 3-dichloro-2-propyl) phosphate inhibit growth of female zebrafish and decrease fecundity [J]. Environmental Science & Technology, 2015, 49(24): 14579-14587.

[116]

DASGUPTA S, CHENG V, VLIET S M F, et al. Tris(1, 3-dichloro-2-propyl) phosphate exposure during the early-blastula stage alters the normal trajectory of zebrafish embryogenesis [J]. Environmental Science & Technology, 2018, 52(18): 10820-10828.

[117]

ZHU Y, ZHANG J, LIU Y, et al. Environmentally relevant concentrations of the flame retardant tris(1, 3-dichloro-2-propyl) phosphate inhibit the growth and reproduction of earthworms in soil [J]. Environmental Science & Technology Letters, 2019, 6(5): 277-282.

[118]

DISHAW L V, POWERS C M, RYDE I T, et al. Is the penta BDE replacement, tris (1, 3-dichloro-2-propyl) phosphate (TDCPP), a developmental neurotoxicant? Studies in PC12 cells [J]. Toxicology and Applied Pharmacology, 2011, 256(3): 281-289. doi: 10.1016/j.taap.2011.01.005

[119]

MEEKER J D, STAPLETON H M. House dust concentrations of organophosphate flame retardants in relation to hormone levels and semen quality parameters [J]. Environmental Health Perspectives, 2010, 118(3): 318-323. doi: 10.1289/ehp.0901332

[120]

李素珍, 付卫强, 冯承莲. 有机磷酸酯阻燃剂的环境暴露、环境行为和毒性效应研究进展 [J]. 环境工程, 2018, 36(9): 180-184,35. LI S Z, FU W Q, FENG C L. Research progress in envionmental exposure, behaviour and toxic effect of organophosphorus flame retardants [J]. Environmental Engineering, 2018, 36(9): 180-184,35(in Chinese).

[121]

HONG X, CHEN R, HOU R, et al. Triphenyl phosphate (TPHP)-induced neurotoxicity in adult male Chinese rare minnows (Gobiocypris rarus) [J]. Environmental Science & Technology, 2018, 52(20): 11895-11903.

[122]

LI Y, KANG Q, CHEN R, et al. 2-Ethylhexyl diphenyl phosphate and its hydroxylated metabolites are anti-androgenic and cause adverse reproductive outcomes in male Japanese Medaka (Oryzias latipes) [J]. Environmental Science & Technology, 2020, 54(14): 8919-8925.

[123]

YU X, YIN H, PENG H, et al. OPFRs and BFRs induced A549cell apoptosis by caspase-dependent mitochondrial pathway [J]. Chemosphere, 2019, 221: 693-702. doi: 10.1016/j.chemosphere.2019.01.074

[124]

YAN S, WANG Q, YANG L, et al. Comparison of the toxicity effects of tris(1, 3-dichloro-2-propyl)phosphate (TDCIPP) with tributyl phosphate (TNBP) reveals the mechanism of the apoptosis pathway in Asian freshwater clams (Corbicula fluminea) [J]. Environmental Science & Technology, 2020, 54(11): 6850-6858.

[125]

杨扬. 有机磷酸酯(OPEs)对赤子爱胜蚓的毒性效应及机制研究[D]. 南京: 南京大学, 2018. YANG Y. Ecotoxicity effect and mechanism of organophosphorus esters(OPEs)on earthworm Eisenia fetida[D]. Nanjing: Nanjing University, 2018.

[126]

顾杰, 顾爱华, 石利利, 等. 有机磷酸酯环境分布及神经毒性研究进展 [J]. 环境与健康杂志, 2018, 35(3): 277-281. GU J, GU A H, SHI L L, et al. Environmental distribution and neurotoxicity of organic phosphate: A review of recent studies [J]. Journal of Environment and Health, 2018, 35(3): 277-281(in Chinese).

[127]

TA N, LI C, FANG Y, et al. Toxicity of TDCPP and TCEP on PC12 cell: Changes in CAMKII, GAP43, tubulin and NF-H gene and protein levels [J]. Toxicology Letters, 2014, 227(3): 164-171. doi: 10.1016/j.toxlet.2014.03.023

[128]

DU Z, WANG G, GAO S, et al. Aryl organophosphate flame retardants induced cardiotoxicity during zebrafish embryogenesis: By disturbing expression of the transcriptional regulators [J]. Aquatic Toxicology, 2015, 161: 25-32. doi: 10.1016/j.aquatox.2015.01.027

[129]

SU G, CRUMP D, LETCHER R J, et al. Rapid in vitro metabolism of the flame retardant triphenyl phosphate and effects on cytotoxicity and mRNA expression in chicken embryonic hepatocytes [J]. Environmental Science & Technology, 2014, 48(22): 13511-13519.

[130]

闫振飞, 廖伟, 冯承莲, 等. 典型有机磷酸酯阻燃剂分析方法研究进展 [J]. 生态毒理学报, 2020, 15(1): 94-108. doi: 10.7524/AJE.1673-5897.20190509002 YAN Z F, LIAO W, FENG C L, et al. Research progress on analysis methods of typical organophosphate esters ( OPEs) flame retardants [J]. Asian Journal of Ecotoxicology, 2020, 15(1): 94-108(in Chinese). doi: 10.7524/AJE.1673-5897.20190509002

[131]

MARTíNEZ-CARBALLO E, GONZáLEZ-BARREIRO C, SITKA A, et al. Determination of selected organophosphate esters in the aquatic environment of Austria [J]. Science of the Total Environment, 2007, 388(1): 290-299.

[132]

高立红. 北京市城市环境有机磷酸酯污染水平和分布特征研究[D]. 北京: 北京科技大学, 2016. GAO L H. Study on pollution level and distribution characteristics of organophosphate esters in urban environment of Beijing[D]. Beijing: Beijing University of Science and Technology, 2016（in Chinese）.

[133]

严小菊. 典型有机磷酸酯阻燃剂在太湖水体和底泥中存在水平和分布特征[D]. 南京: 南京大学, 2013. YAN X J. The level and distribution of typical organophosphate flame retardants in water and sediment of Taihu Lake[D]. Nanjing: Nanjing University, 2013（in Chinese） .

[134]

RODRíGUEZ I, CALVO F, QUINTANA J B, et al. Suitability of solid-phase microextraction for the determination of organophosphate flame retardants and plasticizers in water samples [J]. Journal of Chromatography A, 2006, 1108(2): 158-165. doi: 10.1016/j.chroma.2006.01.008

[135]

QUINTANA J B, REEMTSMA T. Potential of membrane-assisted solvent extraction for the determination of phosphoric acid triesters in wastewater samples by liquid chromatography–tandem mass spectrometry [J]. Journal of Chromatography A, 2006, 1124(1): 22-28.

[136]

GARCíA-LóPEZ M, RODRíGUEZ I, CELA R. Development of a dispersive liquid-liquid microextraction method for organophosphorus flame retardants and plastizicers determination in water samples [J]. Journal of Chromatography A, 2007, 1166(1-2): 9-15. doi: 10.1016/j.chroma.2007.08.006

[137]

CRISTALE J, LACORTE S. Development and validation of a multiresidue method for the analysis of polybrominated diphenyl ethers, new brominated and organophosphorus flame retardants in sediment, sludge and dust [J]. Journal of Chromatography A, 2013, 1305(1): 267-275.

[138]

MOLLER A, XIE Z, CABA A, et al. Organophosphorus flame retardants and plasticizers in the atmosphere of the North Sea [J]. Environment Pollution, 2011, 159(12): 3660-3665. doi: 10.1016/j.envpol.2011.07.022

[139]

CAO D, GUO J, WANG Y, et al. Organophosphate esters in sediment of the Great Lakes [J]. Environmental Science & Technology, 2017, 51(3): 1441-1449.

[140]

GARCíA-LóPEZ M, RODRíGUEZ I, CELA R. Evaluation of liquid–liquid microextraction using polypropylene microporous membranes for the determination of organophosphorus flame retardants and plasticizers in water samples[J]. Analytica Chimica Acta, 2008, 625(2): 145-153.

[141]

何丽雄, 曹曙霞, 曾祥英, 等. 固相萃取/气相色谱-质谱联用技术快速测定水中有机磷酸酯阻燃剂与增塑剂 [J]. 分析测试学报, 2013, 32(4): 437-441. doi: 10.3969/j.issn.1004-4957.2013.04.008 HE L X, CAO S X, ZENG X Y, et al. Determination of organophosphate flame retardants and plasticizers in water using solid phase extraction coupled with GC-MS [J]. Journal of Instrumental Analysis, 2013, 32(4): 437-441(in Chinese). doi: 10.3969/j.issn.1004-4957.2013.04.008

[142]

秦宏兵, 范苓, 顾海东. 固相萃取-气相色谱/质谱法测定水中6种有机磷酸酯类阻燃剂和增塑剂 [J]. 分析科学学报, 2014, 30(2): 259-262. QIN H B, FAN L, GU H D. Determination of organophosphorus flame retardants and plasticizers in environmental water by solid phase extraction coupled with gas chromatography/mass spectrometry [J]. Journal of Analytical Science, 2014, 30(2): 259-262(in Chinese).

[143]

MARKLUND A, ANDERSSON B, HAGLUND P. Organophosphorus flame retardants and plasticizers in Swedish sewage treatment plants [J]. Environmental Science & Technology, 2005, 39(19): 7423.

[144]

BRANDSMA S H, DE BOER J, LEONARDS P E G, et al. Organophosphorus flame-retardant and plasticizer analysis, including recommendations from the first worldwide interlaboratory study [J]. Trends in Analytical Chemistry, 2013, 43: 217-228. doi: 10.1016/j.trac.2012.12.004

[145]

STUBBINGS W A, RIDDELL N, CHITTIM B, et al. Challenges in the analyses of organophosphate esters [J]. Environmental Science & Technology Letters, 2017, 4(7): 292-297.