2021 Volume 40 Issue 1
Article Contents

CAI Rui, WANG Wenji, XU Hang, JI Rong. Degradation, transformation, and residue formation of tetrabromobisphenol A (TBBPA) in soil: A review[J]. Environmental Chemistry, 2021, (1): 102-110. doi: 10.7524/j.issn.0254-6108.2020021001
Citation: CAI Rui, WANG Wenji, XU Hang, JI Rong. Degradation, transformation, and residue formation of tetrabromobisphenol A (TBBPA) in soil: A review[J]. Environmental Chemistry, 2021, (1): 102-110. doi: 10.7524/j.issn.0254-6108.2020021001

Degradation, transformation, and residue formation of tetrabromobisphenol A (TBBPA) in soil: A review

  • Corresponding author: JI Rong, ji@nju.edu.cn
  • Received Date: 10/02/2020
    Fund Project: Supported by the National Natural Science Foundation of China (31861133003, 21477052) and the Chinese Academy of Engineering (2019-XZ-24).
  • Tetrabromobisphenol A (TBBPA) is the most preferred brominated flame retardant worldwide, used widely in the production of electronic appliances and plastics. Soil is one of the main sinks of contaminants, and the environmental processes and fate of TBBPA in soil are essential to the environmental risk of TBBPA. Here we reviewed the degradation, mineralization, metabolism, and non-extractable residues (NERs)-formation of TBBPA in soil under various redox conditions (anoxic incubation, sequential anoxic-oxic incubation, and oxic incubation) and in the presence of plants (reed and rice) and earthworms (Metaphire guillelmi and Eisenia fetida). In anoxic soil, TBBPA was reductively debrominated to end product bisphenol A, which was not degraded in soil under further incubation, while in oxic soil, TBBPA was transformed to various metabolites via O-methylation, ipso-hydroxylation, and oxidative skeletal cleavage. The presence of plants and earthworms changed the fate of TBBPA, increased the mineralization and the formation of persistent O-methylation metabolites, and decreased formation of NERs. TBBPA and its metabolites could form NERs with soil organic matter via ester- and ether-linkages. When soil redox conditions were changed, TBBPA and its metabolites could be released from the NERs, while amendment of rice root exudates did not have significant effect on the NERs release. Further studies are needed on microbiology of TBBPA transformation in soil, contributions of physico-chemical entrapment, covalent bondings, and biological assimilation to NER formation, transformation of TBBPA in organisms, especially in the body of plants and soil animals, and soil stability and biological effects of NERs that are formed in soil and organisms, to provide data for comprehensive assessment on environmental risks of TBBPA.
  • 加载中
  • [1] COVACI A, VOORSPOELS S, ABDALLAH M A, et al. Analytical and environmental aspects of the flame retardant tetrabromobisphenol A and its derivatives[J]. Journal of Chromatography A, 2009, 1216(3):346-363.

    Google Scholar Pub Med

    [2] HARRAD S, ABDALLAH M A, ROSE N L, et al. Current-use brominated flame retardants in water, sediment, and fish from English lakes[J]. Environmental Science & Technology, 2009, 43(24):9077-9083.

    Google Scholar Pub Med

    [3] SHI T, CHEN S J, LUO X J, et al. Occurrence of brominated flame retardants other than polybrominated diphenyl ethers in environmental and biota samples from southern China[J]. Chemosphere, 2009, 74(7):910-916.

    Google Scholar Pub Med

    [4] MCCORMICK J M, PAIVA M S, HÄGGBLOM M M, et al. Embryonic exposure to tetrabromobisphenol A and its metabolites, bisphenol A and tetrabromobisphenol A dimethyl ether disrupts normal zebrafish (Danio rerio) development and matrix metalloproteinase expression[J]. Aquatic Toxicology, 2010, 100(3):255-262.

    Google Scholar Pub Med

    [5] MORF L S, TREMP J, GLOOR R, et al. Brominated flame retardants in waste electrical and electronic equipment:Substance flows in a recycling plant[J]. Environmental Science & Technology, 2005, 39(22):8691-8699.

    Google Scholar Pub Med

    [6] ÖBERG T, ÖBERG K, WARMAN K, et al. Distribution and levels of brominated flame retardants in sewage sludge[J]. Chemosphere, 2002, 48(8):805-809.

    Google Scholar Pub Med

    [7] 王俊霞, 刘莉莉, 郭杰, 等. 溴代阻燃剂在中国川藏地区的污染和分布特征[J]. 环境科学学报, 2014, 34(11):2823-2831. WANG J X, LIU L L, GUO J, et al. Levels and distribution of brominated flame retardants in Sichuan-Tibet region, China[J]. Acta Scientiae Circumstantiae, 2014,34(11):2823-2831(in Chinese).

    Google Scholar Pub Med

    [8] KÄSTNER M, NOWAK K M, MILTNER A, et al. Classification and modelling of nonextractable residue (NER) formation of xenobiotics in soil-a synthesis[J]. Critical Reviews in Environmental Science & Technology, 2014, 44(19):2107-2171.

    Google Scholar Pub Med

    [9] ANDREU V, PICÓ Y. Determination of pesticides and their degradation products in soil:Critical review and comparison of methods[J]. TrAC Trends in Analytical Chemistry, 2004, 23(10/11):772-789.

    Google Scholar Pub Med

    [10] TONG F, GU X Y, GU C, et al. Insights into tetrabromobisphenol A adsorption onto soils:Effects of soil components and environmental factors[J]. Science of the Total Environment, 2015, 536:582-588.

    Google Scholar Pub Med

    [11] CHEN X, GU J Q, WANG Y F, et al. Fate and O-methylating detoxification of tetrabromobisphenol A (TBBPA) in two earthworms (Metaphire guillelmi and Eisenia fetida)[J]. Environmental Pollution, 2017, 227:526-533.

    Google Scholar Pub Med

    [12] GU J Q, JING Y Y, MA Y N, et al. Effects of the earthworm Metaphire guillelmi on the mineralization, metabolism, and bound-residue formation of tetrabromobisphenol A (TBBPA) in soil[J]. Science of the Total Environment, 2017, 595:528-536.

    Google Scholar Pub Med

    [13] LI Y N, ZHOU Q X, WANG Y Y, et al. Fate of tetrabromobisphenol A and hexabromocyclododecane brominated flame retardants in soil and uptake by plants[J]. Chemosphere, 2011, 82(2):204-209.

    Google Scholar Pub Med

    [14] LI H W, HU Y X, SUN Y X, et al. Bioaccumulation and translocation of tetrabromobisphenol A and hexabromocyclododecanes in mangrove plants from a national nature reserve of Shenzhen City, South China[J]. Environment International, 2019, 129:239-246.

    Google Scholar Pub Med

    [15] SUN F F, KOLVENBACH B A, NASTOLD P, et al. Degradation and metabolism of tetrabromobisphenol A (TBBPA) in submerged soil and soil-plant systems[J]. Environmental Science & Technology, 2014, 48(24):14291-14299.

    Google Scholar Pub Med

    [16] WANG S F, CAO S Q, WANG Y F, et al. Fate and metabolism of the brominated flame retardant tetrabromobisphenol A (TBBPA) in rice cell suspension culture[J]. Environmental Pollution, 2016, 214:299-306.

    Google Scholar Pub Med

    [17] LIU A F, ZHAO Z S, QU G B, et al. Transformation/degradation of tetrabromobisphenol A and its derivatives:A review of the metabolism and metabolites[J]. Environmental Pollution, 2018, 243:1141-1153.

    Google Scholar Pub Med

    [18] YU Y J, YU Z L, CHEN H B, et al. Tetrabromobisphenol A:Disposition, kinetics and toxicity in animals and humans[J]. Environmental Pollution, 2019, 253:909-917.

    Google Scholar Pub Med

    [19] KURAMOCHI H, KAWAMOTO K, MIYAZAKI K, et al. Determination of physicochemical properties of tetrabromobisphenol A[J]. Environmental Toxicology and Chemistry, 2008, 27(12):2413-2418.

    Google Scholar Pub Med

    [20] PENG X X, ZHANG Z L, LUO W S, et al. Biodegradation of tetrabromobisphenol A by a novel Comamonas sp. strain, JXS-2-02, isolated from anaerobic sludge[J]. Bioresource Technology, 2013, 128:173-179.

    Google Scholar Pub Med

    [21] 谢慧,王军,王彦红,等. 四溴双酚A在土壤中的降解动态及其对土壤微生物数量和酶活性的影响[J]. 环境化学, 2017, 36(7):1614-1621. XIE H, WANG J, WANG Y H, et al. Degradation dynamics of tetrabromobisphenol A in soil and in effects on soil microorganisms and enzymatic activity[J]. Environmental Chemistry, 2017,36(7):1614-1621(in Chinese).

    Google Scholar Pub Med

    [22] LIU J, WANG Y F, JIANG B Q, et al. Degradation, metabolism, and bound-residue formation and release of tetrabromobisphenol A in soil during sequential anoxic-oxic incubation[J]. Environmental Science & Technology, 2013, 47(15):8348-8354.

    Google Scholar Pub Med

    [23] LI F J, WANG J J, JIANG B Q, et al. Fate of tetrabromobisphenol A (TBBPA) and formation of ester- and ether-linked bound residues in an oxic sandy soil[J]. Environmental Science & Technology, 2015, 49(21):12758-12765.

    Google Scholar Pub Med

    [24] ARMENANTE P M, KAFKEWITZ D, LEWANDOWSKI G A, et al. Anaerobic-aerobic treatment of halogenated phenolic compounds[J]. Water Research, 1999, 33(3):681-692.

    Google Scholar Pub Med

    [25] LI M T, HAO L L, SHENG L X, et al. Identification and degradation characterization of hexachlorobutadiene degrading strain Serratia marcescens HL1[J]. Bioresource Technology, 2008, 99(15):6878-6884.

    Google Scholar Pub Med

    [26] UNGER I M, KENNEDY A C, MUZIKA R. Flooding effects on soil microbial communities[J]. Applied Soil Ecology, 2009, 42(1):1-8.

    Google Scholar Pub Med

    [27] NYHOLM J R, LUNDBERG C, ANDERSSON P L. Biodegradation kinetics of selected brominated flame retardants in aerobic and anaerobic soil[J]. Environmental Pollution, 2010, 158(6):2235-2240.

    Google Scholar Pub Med

    [28] MCAVOY D C, PITTINGER C A, WILLIS A M. Biotransformation of tetrabromobisphenol A (TBBPA) in anaerobic digester sludge, soils, and freshwater sediments[J]. Ecotoxicology and Environmental Safety, 2016, 131:143-150.

    Google Scholar Pub Med

    [29] ARBELI Z, RONEN Z. Enrichment of a microbial culture capable of reductive debromination of the flame retardant tetrabromobisphenol A, and identification of the intermediate metabolites produced in the process[J]. Biodegradation, 2003, 14(6):385-395.

    Google Scholar Pub Med

    [30] RAVIT B, EHRENFELD J G, HÄGGBLOM M M. Salt marsh rhizosphere affects microbial biotransformation of the widespread halogenated contaminant tetrabromobisphenol A (TBBPA)[J]. Soil Biology and Biochemistry, 2005, 37(6):1049-1057.

    Google Scholar Pub Med

    [31] VOORDECKERS J W, FENNELL D E, JONES K, et al. Anaerobic biotransformation of tetrabromobisphenol A, tetrachlorobisphenol A, and bisphenol A in estuarine sediments[J]. Environmental Science & Technology, 2002, 36(4):696-701.

    Google Scholar Pub Med

    [32] CHANG B V, YUAN S Y, REN Y L. Anaerobic degradation of tetrabromobisphenol A in river sediment[J]. Ecological Engineering, 2012, 4973-4976.

    Google Scholar Pub Med

    [33] PENG X X, ZHANG Z L, ZHAO Z L, et al. 16S ribosomal DNA clone libraries to reveal bacterial diversity in anaerobic reactor-degraded tetrabromobisphenol A[J]. Bioresource Technology, 2012, 112:75-82.

    Google Scholar Pub Med

    [34] RONEN Z, ABELIOVICH A. Anaerobic-aerobic process for microbial degradation of tetrabromobisphenol A[J]. Applied and Environmental Microbiology, 2000, 66(6):2372-2377.

    Google Scholar Pub Med

    [35] LI F J, JIANG B Q, NASTOLD P, et al. Enhanced transformation of tetrabromobisphenol A by nitrifiers in nitrifying activated sludge[J]. Environmental Science & Technology, 2015, 49(7):4283-4292.

    Google Scholar Pub Med

    [36] CHANG B V, YUAN S Y, REN Y L. Aerobic degradation of tetrabromobisphenol A by microbes in river sediment[J]. Chemosphere, 2012, 87(5):535-541.

    Google Scholar Pub Med

    [37] GEORGE K W, HAGGBLOM M M. Microbial O-methylation of the flame retardant tetrabromobisphenol A[J]. Environmental Science & Technology, 2008, 42(15):5555-5561.

    Google Scholar Pub Med

    [38] WANG S F, SUN F F, WANG Y F, et al. Formation, characterization, and mineralization of bound residues of tetrabromobisphenol A (TBBPA) in silty clay soil under oxic conditions[J]. Science of the Total Environment, 2017, 599/600:332-339.

    Google Scholar Pub Med

    [39] MICHAŁOWICZ J. Bisphenol A-Sources, toxicity and biotransformation[J]. Environmental Toxicology and Pharmacology, 2014, 37(2):738-758.

    Google Scholar Pub Med

    [40] 张静,严静娜,郭悦宁,等. 阻燃剂四溴双酚A的厌氧-好氧生物降解[J]. 环境化学, 2016, 35(9):1776-1784. ZHANG J, YAN J N, GUO Y N, et al. Anaerobic and aerobic biodegradation of flame retardant tetrabromobisphenol A[J]. Environmental Chemistry, 2016, 35(9):1776-1784(in Chinese).

    Google Scholar Pub Med

    [41] GABRIEL F L P, CYRIS M, GIGER W, et al. ipso-Substitution:A general biochemical and biodegradation mechanism to cleave α-quaternary alkylphenols and bisphenol A[J]. Chemistry & Biodiversity, 2007, 4(9):2123-2137.

    Google Scholar Pub Med

    [42] KOLVENBACH B, SCHLAICH N, RAOUI Z, et al. Degradation pathway of bisphenol A:Does ipso substitution apply to phenols containing a quaternary α-carbon structure in the para position?[J]. Applied and Environmental Microbiology, 2007, 73(15):4776-4784.

    Google Scholar Pub Med

    [43] LIU A F, ZHAO Z S, QU G B, et al. Identification of transformation/degradation products of tetrabromobisphenol A and its derivatives[J]. TrAC Trends in Analytical Chemistry, 2019, 111:85-99.

    Google Scholar Pub Med

    [44] AN T C, ZU L, LI G Y, et al. One-step process for debromination and aerobic mineralization of tetrabromobisphenol A by a novel Ochrobactrum sp. T isolated from an e-waste recycling site[J]. Bioresource Technology, 2011, 102(19):9148-9154.

    Google Scholar Pub Med

    [45] HOU X W, YU M, LIU A F, et al. Biotransformation of tetrabromobisphenol A dimethyl ether back to tetrabromobisphenol A in whole pumpkin plants[J]. Environmental Pollution, 2018, 241:331-338.

    Google Scholar Pub Med

    [46] LEIGH M B, FLETCHER J S, FU X, et al. Root turnover:An important source of microbial substrates in rhizosphere remediation of recalcitrant contaminants[J]. Environmental Science & Technology, 2002, 36(7):1579-1583.

    Google Scholar Pub Med

    [47] XIAO X M, BOLES S, FROLKING S, et al. Mapping paddy rice agriculture in South and Southeast Asia using multi-temporal MODIS images[J]. Remote Sensing of Environment, 2006, 100(1):95-113.

    Google Scholar Pub Med

    [48] JOUANNEAU Y, WILLISON J C, MEYER C, et al. Stimulation of pyrene mineralization in freshwater sediments by bacterial and plant bioaugmentation[J]. Environmental Science & Technology, 2005, 39(15):5729-5735.

    Google Scholar Pub Med

    [49] LI F J, WANG J J, NASTOLD P, et al. Fate and metabolism of tetrabromobisphenol A in soil slurries without and with the amendment with the alkylphenol degrading bacterium Sphingomonas sp. strain TTNP3[J]. Environmental Pollution, 2014, 193:181-188.

    Google Scholar Pub Med

    [50] 侯兴旺, 刘稷燕, 江桂斌. 典型卤代有机污染物在植物体内的代谢过程[J]. 中国科学:化学, 2018, 48(10):1236-1246. HOU X W, LIU J Y, JIANG G B. Metabolism of typical halogenated organic pollutants in plant[J]. Sci Sin Chim, 2018, 48(10):1236-1246(in Chinese).

    Google Scholar Pub Med

    [51] REA P A. Plant ATP-binding cassette transporter[J]. Annual Review of Plant Biology, 2007, 58:347-375.

    Google Scholar Pub Med

    [52] VAN GROENIGEN J W, LUBBERS I M, VOS H M J, et al. Earthworms increase plant production:A meta-analysis[J]. Scientific Reports, 2015, 4:6365. DOI:10.1038/srep06365.

    Google Scholar Pub Med

    [53] HICKMAN Z A, REID B J. Earthworm assisted bioremediation of organic contaminants[J]. Environment International, 2008, 34(7):1072-1081.

    Google Scholar Pub Med

    [54] GU J Q, CHEN X, WANG Y F, et al. Bioaccumulation, physiological distribution, and biotransformation of tetrabromobisphenol A (TBBPA) in the geophagous earthworm Metaphire guillelmi-hint for detoxification strategy[J]. Journal of Hazardous Materials, 2020, 388:122027. DOI:/10.1016/j.jhazmat.2020.122027

    Google Scholar Pub Med

    [55] CHEN X, GU X Y, ZHAO X P, et al. Species-dependent effects of earthworms on the fates and bioavailability of tetrabromobisphenol A and cadmium coexisted in soils[J]. Science of the Total Environment, 2019, 658:1416-1422.

    Google Scholar Pub Med

    [56] WANG F, JI R, JIANG Z, et al. Species-dependent effects of biochar amendment on bioaccumulation of atrazine in earthworms[J]. Environmental Pollution, 2014, 186:241-247.

    Google Scholar Pub Med

    [57] FVHR F, OPHOFF H, BURAUEL P, et al. Modification of definition of bound residues//FUHR F, OPHOFF H (eds). Pesticide bound residues in soil[M]. Weinheim:Wiley, 1998:175-176.

    Google Scholar Pub Med

    [58] SEN GUPTA S, BHATTACHARYYA K G. Kinetics of adsorption of metal ions on inorganic materials:A review[J]. Advances in Colloid and Interface Science, 2011, 162(1/2):39-58.

    Google Scholar Pub Med

    [59] GEVAO B, SEMPLE K T, JONES K C. Bound pesticide residues in soils:A review[J]. Environmental Pollution, 2000, 108(1):3-14.

    Google Scholar Pub Med

    [60] BARRACLOUGH D, KEARNEY T, CROXFORD A. Bound residues:Environmental solution or future problem?[J]. Environmental Pollution, 2005, 133(1):85-90.

    Google Scholar Pub Med

    [61] TONG F, GU X Y, GU C, et al. Stimulation of tetrabromobisphenol A binding to soil humic substances by birnessite and the chemical structure of the bound residues[J]. Environmental Science & Technology, 2016, 50(12):6257-6266.

    Google Scholar Pub Med

    [62] 王松凤,吴玄,王麒麟,等. 土壤中四溴双酚A不可提取态残留的降解转化[J]. 科学通报, 2019, 64(33):3458-3466. WANG S F, WU X, WANG Q L, et al. The degradation and transformation of TBBPA-derived NER in soil[J]. Chinese Science Bulletin,2019, 64(33):3458-3466(in Chinese).

    Google Scholar Pub Med

    [63] WANG S F, LING X H, WU X, et al. Release of tetrabromobisphenol A (TBBPA)-derived non-extractable residues in oxic soil and the effects of the TBBPA-degrading bacterium Ochrobactrum sp. strain T[J]. Journal of Hazardous Materials, 2019, 378:120666. DOI:10.1016/j.jhazmat.2019.05.059.

    Google Scholar Pub Med

  • 加载中
通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索

Article Metrics

Article views(3283) PDF downloads(117) Cited by(0)

Access History

Degradation, transformation, and residue formation of tetrabromobisphenol A (TBBPA) in soil: A review

Fund Project: Supported by the National Natural Science Foundation of China (31861133003, 21477052) and the Chinese Academy of Engineering (2019-XZ-24).

Abstract: Tetrabromobisphenol A (TBBPA) is the most preferred brominated flame retardant worldwide, used widely in the production of electronic appliances and plastics. Soil is one of the main sinks of contaminants, and the environmental processes and fate of TBBPA in soil are essential to the environmental risk of TBBPA. Here we reviewed the degradation, mineralization, metabolism, and non-extractable residues (NERs)-formation of TBBPA in soil under various redox conditions (anoxic incubation, sequential anoxic-oxic incubation, and oxic incubation) and in the presence of plants (reed and rice) and earthworms (Metaphire guillelmi and Eisenia fetida). In anoxic soil, TBBPA was reductively debrominated to end product bisphenol A, which was not degraded in soil under further incubation, while in oxic soil, TBBPA was transformed to various metabolites via O-methylation, ipso-hydroxylation, and oxidative skeletal cleavage. The presence of plants and earthworms changed the fate of TBBPA, increased the mineralization and the formation of persistent O-methylation metabolites, and decreased formation of NERs. TBBPA and its metabolites could form NERs with soil organic matter via ester- and ether-linkages. When soil redox conditions were changed, TBBPA and its metabolites could be released from the NERs, while amendment of rice root exudates did not have significant effect on the NERs release. Further studies are needed on microbiology of TBBPA transformation in soil, contributions of physico-chemical entrapment, covalent bondings, and biological assimilation to NER formation, transformation of TBBPA in organisms, especially in the body of plants and soil animals, and soil stability and biological effects of NERs that are formed in soil and organisms, to provide data for comprehensive assessment on environmental risks of TBBPA.

Reference (63)

Catalog

    /

    DownLoad:  Full-Size Img  PowerPoint