四溴双酚A去除方法及其机理的研究进展

doi:10.3969/j.issn.1000-1565.2020.05.006

摘要/Abstract

摘要： 新型污染物四溴双酚A(TBBPA)是一种常见的溴系阻燃剂(BFRs),广泛存在于塑料制品、纺织品和电子元件等产品中.由于TBBPA作为非反应型添加剂加到产品中,而易于扩散到环境中,并且因其具有持久性、生物毒性和累积性,进而对生态环境和人类健康造成严重威胁,因此环境中TBBPA的去除研究成为目前热点问题.论文通过近几年国内外的相关研究,对TBBPA的吸附、热降解、光降解和催化降解等去除方法及其机理进行了评述和比较,并对存在问题和今后研究方向进行了讨论和展望.

关键词: 四溴双酚A, 去除, 机理, 途径, 产物

Abstract: Tetrabromobisphenol A(TBBPA), an emerging contaminant, is a common bromine-based flame retardant(BFRs)widely found in plastics, textiles and electronic components. Since TBBPA is added as a non-reactive additive to the product, it is easy to spread into the environment. Because of its persistence, biotoxicity and accumulation, it poses a serious threat to the ecological environment and human health. Therefore, the removal of TBBPA in the environment has become a hot issue. At home and abroad, the methods and mechanisms of adsorption, thermal degradation, photodegradation and catalytic degradation of TBBPA were reviewed and compared, and the existing problems and future research directions were discussed and prospected.

Key words: tetrabromobisphenol A, removal, mechanism, pathway, products

中图分类号:

X832

巩一潮,刘芃岩,刘桂随. 四溴双酚A去除方法及其机理的研究进展[J]. 河北大学学报(自然科学版), 2020, 40(5): 484-493.

GONG Yichao,LIU Pengyan,LIU Guisui. Research progress on the removal method and mechanism of tetrabromobisphenol A[J]. Journal of Hebei University (Natural Science Edition), 2020, 40(5): 484-493.

参考文献

[1] LAW R J, ALLCHIN C R, DE BOER J, et al. Levels and trends of brominated flame retardants in the European environment[J]. Chemosphere, 2006,64(2):187-208. DOI:10.1016/j.chemosphere.2005.12.007.
[2] BIRNBAUM L S S D. Brominated flame retardants: cause for concern?[J]. Environmental Health Perspectives, 2004,112(1):9-17. DOI:10.1289/ehp.6559.
[3] LIU K, LI J, YAN S, et al. A review of status of tetrabromobisphenol A(TBBPA)in China[J]. Chemosphere, 2016,148:8-20. DOI:10.1016/j.chemosphere.2016.01.023.
[4] WATANABE I, KASHIMOTO T, TATSUKAWA R. Polybrominated biphenyl ethers in marine fish, shellfish and river and marine sediments in Japan[J]. Chemosphere, 1987,16(10):2389-2396. DOI:10.1016/0045-6535(87)90297-9.
[5] SALAPASIDOU M, SAMARA C, VOUTSA D. Endocrine disrupting compounds in the atmosphere of the urban area of Thessaloniki, Greece[J]. Atmospheric Environment, 2011,45(22):3720-3729. DOI:10.1016/j.atmosenv.2011.04.025.
[6] BATTERMAN S, GODWIN C, CHERNYAK S, et al. Brominated flame retardants in offices in Michigan, U.S.A.[J]. Environment International, 2010,36(6):548-556. DOI:10.1016/j.envint.2010.04.008.
[7] COVACI A, HARRAD S, ABDALLAH M A E, et al. Novel brominated flame retardants: A review of their analysis, environmental fate and behaviour[J]. Environment International, 2011,37(2):532-556. DOI:10.1016/j.envint.2010.11.007.
[8] MATSUKAMI H, TUE N M, SUZUKI G, et al. Flame retardant emission from e-waste recycling operation in northern Vietnam: Environmental occurrence of emerging organophosphorus esters used as alternatives for PBDEs[J]. Science of The Total Environment, 2015,514:492-499. DOI:10.1016/j.scitotenv.2015.02.008.
[9] HUANG Q, LIU W, PENG P A, et al. Reductive debromination of tetrabromobisphenol A by Pd/Fe bimetallic catalysts[J]. Chemosphere, 2013,92(10):1321-1327. DOI:10.1016/j.chemosphere.2013.05.021.
[10] OSAKO M, KIM Y, SAKAI S. Leaching of brominated flame retardants in leachate from landfills in Japan[J]. Chemosphere, 2004,57(10):1571-1579. DOI:10.1016/j.chemosphere.2004.08.076.
[11] FASFOUS I I, RADWAN E S, DAWOUD J N. Kinetics, equilibrium and thermodynamics of the sorption of tetrabromobisphenol A on multiwalled carbon nanotubes[J]. Applied Surface Science, 2010,256(23):7246-7252. DOI:10.1016/j.apsusc.2010.05.059.
[12] ZHANG Y, TANG Y, LI S, et al. Sorption and removal of tetrabromobisphenol A from solution by graphene oxide[J]. Chemical Engineering Journal, 2013,222:94-100. DOI:10.1016/j.cej.2013.02.027.
[13] SHEN J, HUANG G, AN C, et al. Removal of Tetrabromobisphenol A by adsorption on pinecone-derived activated charcoals: Synchrotron FTIR, kinetics and surface functionality analyses[J]. Bioresource Technology, 2018,247:812-820. DOI:10.1016/j.biortech.2017.09.177.
[14] ZHOU L, JI L, MA P, et al. Development of carbon nanotubes/CoFe₂O₄ magnetic hybrid material for removal of tetrabromobisphenol A and Pb(II)[J]. Journal of Hazardous Materials, 2014,265:104-114. DOI:10.1016/j.jhazmat.2013.11.058.
[15] ZHANG Y, JING L, HE X, et al. Sorption enhancement of TBBPA from water by fly ash-supported nanostructured γ-MnO₂[J]. Journal of Industrial and Engineering Chemistry, 2015,21:610-619. DOI:10.1016/j.jiec.2014.03.027.
[16] ZHOU Q, WANG Y, XIAO J, et al. Preparation of magnetic core-shell Fe₃O₄@ polyaniline composite material and its application in adsorption and removal of tetrabromobisphenol A and decabromodiphenyl ether[J]. Ecotoxicology and environmental safety, 2019,183:109471. DOI:10.1016/j.ecoenv.2019.109471.
[17] LIU L L, CHEN X, WANG Z P, et al. The removal mechanism and performance of tetrabromobisphenol A with a novel multi-group activated carbon from recycling long-root Eichhornia crassipes plants[J]. RSC advances, 2019,9(43):24760-24769. DOI:10.1039/C9RA03374B.
[18] CUI Y Y, REN H B, YANG C X, et al. Room-temperature synthesis of microporous organic network for efficient adsorption and removal of tetrabromobisphenol A from aqueous solution[J]. Chemical Engineering Journal, 2019,368:589-597. DOI:10.1016/j.cej.2019.02.153.
[19] CUI Y Y, REN H B, YANG C X, et al. Facile synthesis of hydroxyl enriched microporous organic networks for enhanced adsorption and removal of tetrabromobisphenol A from aqueous solution[J]. Chemical Engineering Journal, 2019,373:606-615. DOI:10.1016/j.cej.2019.05.082.
[20] DUAN F, QIN L, CHEN C, et al. Adsorption of tetrabromobisphenol A in aqueous solutions by porous carbon nanospheres[J]. Carbon, 2019,153:805. DOI:10.1016/j.carbon.2019.06.096.
[21] ZHOU T, TAO Y, XU Y, et al. Facile preparation of magnetic carbon nanotubes@ ZIF-67 for rapid removal of tetrabromobisphenol A from water sample[J]. Environmental Science and Pollution Research, 2018,25(35):35602-35613. DOI:10.1007/s11356-018-3239-9.
[22] BARONTINI F, MARSANICH K, PETARCA L, et al. The thermal degradation process of tetrabromobisphenol A[J]. Industrial & Engineering Chemistry Research, 2004,43(9):1952-1961. DOI:10.1021/ie034017c.
[23] MARSANICH K, ZANELLI S, BARONTINI F, et al. Evaporation and thermal degradation of tetrabromobisphenol A above the melting point[J]. Thermochimica Acta, 2004,421(1-2):95-103. DOI:org/10.1016/j.tca.2004.03.013.
[24] BARONTINI F, COZZANI V, MARSANICH K, et al. An experimental investigation of tetrabromobisphenol A decomposition pathways[J]. Journal of Analytical and Applied Pyrolysis, 2004,72(1):41-53. DOI:10.1016/j.jaap.2004.02.003.
[25] LUDA M P, BALABANOVICH A I, HORNUNG A, et al. Thermal degradation of a brominated bisphenol a derivative[J]. Polymers for Advanced Technologies, 2003,14(11-12):741-748. DOI:10.1002/pat.389.
[26] BARONTINI F, MARSANICH K, PETARCA L, et al. Thermal degradation and decomposition products of electronic boards containing BFRs[J]. Industrial & Engineering Chemistry Research, 2005,44(12):4186-4199. DOI:10.1021/ie048766l.
[27] ZHANG C C, SAHAJWALLA V, ZHANG F S. Tetrabromobisphenol A recovery from computer housing plastic by a new solvothermal process[J]. Environmental Chemistry Letters, 2014,12(2):347-352. DOI:10.1007/s10311-014-0452-8.
[28] ZHANG C C, ZHANG F S. Removal of brominated flame retardant from electrical and electronic waste plastic by solvothermal technique[J]. Journal of Hazardous Materials, 2012,221-222:193-198. DOI:10.1016/j.jhazmat.2012.04.033.
[29] KUMAGAI S, GRAUSE G, KAMEDA T, et al. Thermal decomposition of tetrabromobisphenol-A containing printed circuit boards in the presence of calcium hydroxide[J]. Journal of Material Cycles and Waste Management, 2017,19(1):282-293. DOI:10.1007/s10163-015-0417-4.
[30] OLESZEK S, GRABDA M, SHIBATA E, et al. Study of the reactions between tetrabromobisphenol A and PbO and Fe₂O₃ in inert and oxidizing atmospheres by various thermal methods[J]. Thermochimica Acta, 2013,566:218-225. DOI:10.1016/j.tca.2013.06.003.
[31] AL-HARAHSHEH M, ALJARRAH M, AL-OTOOM A, et al. Pyrolysis kinetics of tetrabromobisphenol a(TBBPA)and electric arc furnace dust mixtures[J]. Thermochimica Acta, 2018,660:61-69. DOI:10.1016/j.tca.2017.12.022.
[32] AL-HARAHSHEH M, AL-OTOOM A, AL-JARRAH M, et al. Thermal analysis on the pyrolysis of tetrabromobisphenol A and electric arc furnace dust mixtures[J]. Metallurgical and Materials Transactions B, 2018,49(1):45-60. DOI:10.1007/s11663-017-1121-7.
[33] OLESZEK S, GRABDA M, SHIBATA E, et al. Fate of lead oxide during thermal treatment with tetrabromobisphenol A[J]. Journal of Hazardous Materials, 2013,261:163-171. DOI:10.1016/j.jhazmat.2013.07.028.
[34] GRABDA M, OLESZEK S, SHIBATA E, et al. Study on simultaneous recycling of EAF dust and plastic waste containing TBBPA[J]. Journal of Hazardous Materials, 2014,278:25-33. DOI:10.1016/j.jhazmat.2014.05.084.
[35] HAN Q, DONG W Y, WANG H J, et al. Degradation of tetrabromobisphenol a by ozonation: Performance, products, mechanism and toxicity[J]. Chemosphere, 2019,235:701-712. DOI:10.1016/j.chemosphere.2019.06.204.
[36] ERIKSSON J, RAHM S, GREEN N, et al. Photochemical transformations of tetrabromobisphenol A and related phenols in water[J]. Chemosphere, 2004,54(1):117-126. DOI:10.1016/S0045-6535(03)00704-5.
[37] JAKOBSSON K, THURESSON K, RYLANDER L, et al. Exposure to polybrominated diphenyl ethers and tetrabromobisphenol A among computer technicians[J]. Chemosphere, 2002,46(5): 709-716. DOI:10.1016/S0045-6535(01)00235-1.
[38] GUO Y G, ZHOU J, LOU X Y, et al. Enhanced degradation of Tetrabromobisphenol A in water by a UV/base/persulfate system: Kinetics and intermediates[J]. Chemical Engineering Journal, 2014,254:538-544. DOI:10.1016/j.cej.2014.05.143.
[39] WANG S, WANG Z, HAO C, et al. A DFT/TDDFT study on the mechanisms of direct and indirect photodegradation of tetrabromobisphenol A in water[J]. Chemosphere, 2019,220:40-46. DOI:10.1016/j.chemosphere.2018.12.087.
[40] HE H, JI Q Y, GAO Z Q, et al. Degradation of tri(2-chloroisopropyl)phosphate by the UV/H₂O₂ system: Kinetics, mechanisms and toxicity evaluation[J]. Chemosphere, 2019,236:124388. DOI:10.1016/j.chemosphere.2019.124388.
[41] ZHONG Y, LIANG X, TAN W, et al. A comparative study about the effects of isomorphous substitution of transition metals(Ti, Cr, Mn, Co and Ni)on the UV/Fenton catalytic activity of magnetite[J]. Journal of Molecular Catalysis A: Chemical, 2013,372:29-34. DOI:10.1016/j.molcata.2013.01.038.
[42] ZHONG Y, LIANG X, ZHONG Y, et al. Heterogeneous UV/Fenton degradation of TBBPA catalyzed by titanomagnetite: catalyst characterization, performance and degradation products[J]. Water Research, 2012,46(15):4633-4644. DOI:10.1016/j.watres.2012.06.025.
[43] LI N, ZHANG J Q, WANG C P, et al. Enhanced photocatalytic degradation of tetrabromobisphenol A by tourmaline-TiO₂ composite catalyst[J]. Journal of Materials Science, 2017,52(12):6937-6949. DOI:10.1016/S1872-2067(17)62795-5.
[44] ZHANG X Y, ZHANG H X, XIANG Y Y, et al. Synthesis of silver phosphate/graphene oxide composite and its enhanced visible light photocatalytic mechanism and degradation pathways of tetrabromobisphenol A[J]. Journal of Hazardous Materials, 2018,342:353-363. DOI:10.1016/j.jhazmat.2017.08.048.
[45] TANG Y, DONG L, MAO S, et al. Enhanced photocatalytic removal of tetrabromobisphenol A by magnetic CoO@ graphene nanocomposites under visible-light irradiation[J]. ACS Applied Energy Materials, 2018,1(6):2698-2708. DOI:10.1021/acsaem.8b00379.
[46] AN B H, LIU Y A, XU C C, et al. Novel magnetically separable Fe₃O₄-WSe₂/NG photocatalysts: synthesis and photocatalytic performance under visible-light irradiation[J]. New Journal of Chemistry, 2018,42(11):8914-8923. DOI:10.1039/C8NJ00406D.
[47] SAHU R S, SHIH Y H. Reductive debromination of tetrabromobisphenol A by tailored carbon nitride Fe/Cu nanocomposites under an oxic condition[J]. Chemical Engineering Journal, 2019,378:122059. DOI:10.1016/j.cej.2019.122059.
[48] GUO Y, CHEN L, MA F, et al. Efficient degradation of tetrabromobisphenol A by heterostructured Ag/Bi₅Nb₃O₁₅ material under the simulated sunlight irradiation[J]. Journal of Hazardous Materials, 2011,189(1-2):614-618. DOI:10.1016/j.jhazmat.2011.02.054.
[49] LI J H, YANG F, ZHOU Q, et al. Visible-light photocatalytic performance, recovery and degradation mechanism of ternary magnetic Fe₃O₄/BiOBr/BiOI composite[J]. RSC advances, 2019, 9(41): 23545-23553. DOI:10.1039/C9RA04412D.
[50] ZHANG K, HUANG J, ZHANG W, et al. Mechanochemical degradation of tetrabromobisphenol A: performance, products and pathway[J]. Journal of Hazardous Materials, 2012,243:278-285. DOI:10.1016/j.jhazmat.2012.10.034.
[51] HOU Y P, PENG Z B, WANG L, et al. Efficient degradation of tetrabromobisphenol A via electrochemical sequential reduction-oxidation: Degradation efficiency, intermediates, and pathway[J]. Journal of Hazardous Materials, 2018,343:376-385. DOI:10.1016/j.jhazmat.2017.10.004.
[52] PENG Z B, YU Z B, WANG L, et al. Facile synthesis of Pd-Fe nanoparticles modified Ni foam electrode and its behaviors in electrochemical reduction of tetrabromobisphenol A[J]. Materials Letters, 2016,166:300-303. DOI:10.1016/j.matlet.2015.12.110.
[53] PENG X X, TIAN Y, LIU S W, et al. Degradation of TBBPA and BPA from aqueous solution using organo-montmorillonite supported nanoscale zero-valent iron[J]. Chemical Engineering Journal, 2017,309:717-724. DOI:10.1016/j.cej.2016.10.075.
[54] ZIÓŁKOWSKA M, MILEWSKA-DUDA J, DUDA J T. Effect of adsorbate properties on adsorption mechanisms: computational study[J]. Adsorption, 2016,22(4-6):589-597. DOI:10.1007/s10450-015-9736-y.
[55] CHENG H M, HUA Z L. Distribution, release and removal behaviors of tetrabromobisphenol A in water-sediment systems under prolonged hydrodynamic disturbances[J]. Science of the Total Environment, 2018,636:402-410. DOI:10.1016/j.scitotenv.2018.04.276.
[56] RAYNE S, FOREST K, FRIESEN K J. Mechanistic aspects regarding the direct aqueous environmental photochemistry of phenol and its simple halogenated derivatives. A review[J]. Environment International, 2009,35(2):425-437. DOI:10.1016/j.envint.2008.09.004.
[57] WANG X, HU X, ZHANG H, et al. Photolysis kinetics, mechanisms, and pathways of tetrabromobisphenol A in water under simulated solar light irradiation[J]. Environmental Science & Technology, 2015,49(11):6683-6690. DOI:10.1021/acs.est.5b00382.
[58] BAO Y, NIU J. Photochemical transformation of tetrabromobisphenol A under simulated sunlight irradiation: Kinetics, mechanism and influencing factors[J]. Chemosphere, 2015,134:550-556. DOI:10.1016/j.chemosphere.2014.12.016.
[59] GAO S, GUO C, HOU S, et al. Photocatalytic removal of tetrabromobisphenol A by magnetically separable flower-like BiOBr/BiOI/Fe₃O₄ hybrid nanocomposites under visible-light irradiation[J]. Journal of Hazardous Materials, 2017,331:1-12. DOI:10.1016/j.jhazmat.2017.02.030.