Enhanced debromination of 2,2′,4,4′-tetrabromodiphenyl ether (BDE-47) by zero-valent zinc with ascorbic acid

Abstract

• Highly efficient debromination of BDE-47 was achieved in the ZVZ/AA system.

• BDE-47 debromination by the ZVZ/AA can be applied to a wide range of pH.

• AA inhibits the formation of (hydr)oxide and accelerates the corrosion of ZVZ.

• Reduction mechanism of BDE-47 debromination by the ZVZ/AA system was proposed.

A new technique of zero-valent zinc coupled with ascorbic acid (ZVZ/AA) was developed and applied to debrominate the 2,2′,4,4′-Tetrabromodiphenyl ether (BDE-47), which achieved high conversion and rapid debromination of BDE-47 to less- or non-toxic forms. The reaction conditions were optimized by the addition of 100 mg/L ZVZ particles and 3 mmol/L AA at original solution pH= 4.00 using the solvent of methanol/H₂O (v:v= 4:6), which could convert approximately 94% of 5 mg/L BDE-47 into lower-brominated diphenyl ethers within a 90 min at the ZVZ/AA system. The high debromination of BDE-47 was mainly attributed to the effect of AA that inhibits the formation of Zn(II)(hydr)oxide passivation layers and promotes the corrosion of ZVZ, which leads to increase the reactivity of ZVZ. Additionally, ion chromatography and gas chromatography mass spectrometry analyses revealed that bromine ion and lower-debromination diphenyl ethers formed during the reduction of BDE-47. Furthermore, based on the generation of the intermediates products, and its concentration changes over time, it was proposed that the dominant pathway for conversion of BDE-47 was sequential debromination and the final products were diphenyl ethers. These results suggested that the ZVZ/AA system has the potential for highly efficient debromination of BDE-47 from wastewater.

Graphical abstract

Keywords

2,2′,4,4′-tetrabromodiphenyl ether (BDE-47) / Ascorbic acid / Reductive debromination / Zero-valent zinc

References

[1] Abdallah M A, Pawar G, Harrad S (2015). Effect of bromine substitution on human dermal absorption of polybrominated diphenyl ethers. Environmental Science & Technology, 49(18): 10976–10983

[2] Ahmad H B, Abbas Y, Hussain M, Akhtar N, Ansari T M, Zuber M, Zia K M, Arain S A (2014). Synthesis and application of alumina supported nano zero valent zinc as adsorbent for the removal of arsenic and nitrate. Korean Journal of Chemical Engineering, 31(2): 284–288

[3] Al-Harahsheh M, Aljarrah M, Al-Otoom A, Altarawneh M, Kingman S (2018). Pyrolysis kinetics of tetrabromobisphenol a (TBBPA) and electric arc furnace dust mixtures. Thermochimica Acta, 660: 61–69

[4] Blotevogel J, Giraud R J, Borch T (2018). Reductive defluorination of perfluorooctanoic acid by zero-valent iron and zinc: A DFT-based kinetic model. Chemical Engineering Journal, 335: 248–254

[5] Boronina T N, Dieken L, Lagadic I, Klabunde K J (1998). Zinc-silver, zinc-palladium, and zinc-gold as bimetallic systems for carbon tetrachloride dechlorination in water. Journal of Hazardous Substance Research, 1(1): 7

[6] Cao H, He M, Han D, Li J, Li M, Wang W, Yao S (2013). OH-initiated oxidation mechanisms and kinetics of 2,4,4′-Tribrominated diphenyl ether. Environmental Science & Technology, 47(15): 8238–8247

[7] Chen J, Wang C, Pan Y, Farzana S S, Tam N F Y (2018). Biochar accelerates microbial reductive debromination of 2,2',4,4'-tetrabromodiphenyl ether (BDE-47) in anaerobic mangrove sediments. Journal of Hazardous Materials, 341: 177–186

[8] Choi J H, Kim Y H (2009). Reduction of 2,4,6-trichlorophenol with zero-valent zinc and catalyzed zinc. Journal of Hazardous Materials, 166(2–3): 984–991

[9] Chung S S, Zheng J S, Kwong A C S, Lai V W Y (2018). Harmful flame retardant found in electronic cigarette aerosol. Journal of Cleaner Production, 171: 10–16

[10] Djedidi Z, Médard B, Cheikh R B, Mercier G, Tyagi R D, Blais J F (2009). Comparative study of dewatering characteristics of metal precipitates generated during treatment synthetic polymetallic and AMD solutions. Hydrometallurgy, 98(3–4): 247–256

[11] Fang L, Xu L, Li J, Huang L Z (2019). Copper nanoparticles/graphene modified green rusts for debromination of tetrabromobisphenol A: Enhanced galvanic effect, electron transfer and adsorption. Science of the Total Environment, 683: 275–283

[12] Fang Z, Qiu X, Chen J, Qiu X (2011). Debromination of polybrominated diphenyl ethers by Ni/Fe bimetallic nanoparticles: Influencing factors, kinetics, and mechanism. Journal of Hazardous Materials, 185(2–3): 958–969

[13] Fu Z, Wang Y, Chen J, Wang Z, Wang X (2016). How PBDEs are transformed into dihydroxylated and dioxin metabolites catalyzed by the active center of cytochrome P450s: A DFT study. Environmental Science & Technology, 50(15): 8155–8163

[14] Fukuchi S, Nishimoto R, Fukushima M, Zhu Q (2014). Effects of reducing agents on the degradation of 2,4,6-tribromophenol in a heterogeneous Fenton-like system with an iron-loaded natural zeolite. Applied Catalysis B: Environmental, 147: 411–419

[15] Gao X, Yang F, Lan Y, Mao J D, Duan X (2011). Rapid degradation of carbon tetrachloride by commercial micro-scale zinc powder assisted by citric acid. Environmental Chemistry Letters, 9(3): 431–438

[16] Gómara B, Herrero L, Ramos J J, Mateo J R, Fernandez M A, Garcia J F, Gonzalez M J (2007). Distribution of polybrominated diphenyl ethers in human umbilical. cord serum, paternal serum, maternal serum, placentas, and breast milk from Madrid population, Spain. Environmental Science & Technology, 41(20): 6961–6968

[17] Guo J, Jiang D, Wu Y, Zhou P, Lan Y (2011). Degradation of methyl orange by Zn⁰ assisted with silica gel. Journal of Hazardous Materials, 194: 290–296

[18] Guo J, Li Y, Dai R, Lan Y (2012). Rapid reduction of Cr(VI) coupling with efficient removal of total chromium in the coexistence of Zn⁰ and silica gel. Journal of Hazardous Materials, 243: 265–271

[19] Han Y, Chen Z L, Tong L N, Yang L, Shen J M, Wang B Y, Liu Y, Liu Y, Chen Q (2013). Reduction of N-Nitrosodimethylamine with zero-valent zinc. Water Research, 47(1): 216–224

[20] He J, Robrock K R, Alvarez-Cohen L (2006). Microbial reductive debromination of polybrominated diphenyl ethers (PBDEs). Environmental Science & Technology, 40(14): 4429–4434

[21] Hites R A, Foran J A, Schwager S J, Knuth B A, Hamilton M C, Carpenter D O (2004). Global assessment of polybrominated diphenyl ethers in farmed and wild salmon. Environmental Science & Technology, 38(19): 4945–4949

[22] Hou X, Shen W, Huang X, Ai Z, Zhang L (2016). Ascorbic acid enhanced activation of oxygen by ferrous iron: a case of aerobic degradation of rhodamine B. Journal of Hazardous Materials, 308: 67–74

[23] Huang J, Wang X, Long Q, Wen X, Zhou Y, Li L (2009). Influence of pH on the stability characteristics of nanofluids. In: 2009 Symposium on Photonics and Optoelectronics. Washington, DC: IEEE, 1–4

[24] Jeyaraju P (2007). Determination of Vitamin C (Ascorbic Acid) Content in Vitamin C Supplements by Redox Titration. Dissertation for the Doctoral Degree. Sabah: Universiti Malaysia Sabah

[25] Keum Y S, Li Q X (2005). Reductive debromination of polybrominated diphenyl ethers by zerovalent iron. Environmental Science & Technology, 39(7): 2280–2286

[26] Kim M, Guerra P, Theocharides M, Barclay K, Smyth S A, Alaee M (2013). Parameters affecting the occurrence and removal of polybrominated diphenyl ethers in twenty Canadian wastewater treatment plants. Water Research, 47(7): 2213–2221

[27] Kleszczewska E (1999). The spectrophotometry determination of chelate complex: L-ascorbic acid with cuprum (ii) and mercury (ii) in alkaline solution. Polish Journal of Environmental Studies, 8: 313–318

[28] Li A, Tai C, Zhao Z, Wang Y, Zhang Q, Jiang G, Hu J (2007). Debromination of decabrominated diphenyl ether by resin-bound iron nanoparticles. Environmental Science & Technology, 41(19): 6841–6846

[29] Li W, Chen C, Zhu J, Zhou L, Lan Y (2019a). Efficient removal of aniline by micro-scale zinc-copper (mZn/Cu) bimetallic particles in acidic solution: An oxidation degradation mechanism via radicals. Journal of Hazardous Materials, 366: 482–491

[30] Li X, Wang P, Feng C, Liu D, Chen J, Wu F (2019b). Acute toxicity and hazardous concentrations of zinc to native freshwater organisms under different pH values in China. Bulletin of Environmental Contamination and Toxicology, 103(1): 120–126

[31] Liang C, Lin Y T, Shiu J W (2016). Reduction of nitrobenzene with alkaline ascorbic acid: Kinetics and pathways. Journal of Hazardous Materials, 302: 137–143

[32] Lin Y T, Liang C (2013). Carbon tetrachloride degradation by alkaline ascorbic acid solution. Environmental Science & Technology, 47(7): 3299–3307

[33] Lin Y T, Liang C (2015). Reductive dechlorination of carbon tetrachloride using buffered alkaline ascorbic acid. Chemosphere, 136: 27–31

[34] Liu Z, Gu C, Ye M, Bian Y, Cheng Y, Wang F, Yang X, Song Y, Jiang X (2015). Debromination of polybrominated diphenyl ethers by attapulgite-supported Fe/Ni bimetallic nanoparticles: Influencing factors, kinetics and mechanism. Journal of Hazardous Materials, 298: 328–337

[35] Luo S, Yang S, Xue Y, Liang F, Sun C (2011). Two-stage reduction/subsequent oxidation treatment of 2,2′4,4′-tetrabromodiphenyl ether in aqueous solutions: Kinetic, pathway and toxicity. Journal of Hazardous Materials, 192(3): 1795–1803

[36] Lyche J L, Rosseland C, Berge G, Polder A (2015). Human health risk associated with brominated flame-retardants (BFRs). Environment International, 74: 170–180

[37] Mecozzi R, Di Palma L, Pilone D, Cerboni L (2006). Use of EAF dust as heterogeneous catalyst in Fenton oxidation of PCP contaminated wastewaters. Journal of Hazardous Materials, 137(2): 886–892

[38] Moreira Bastos P, Eriksson J, Vidarson J, Bergman A (2008). Oxidative transformation of polybrominated diphenyl ether congeners (PBDEs) and of hydroxylated PBDEs (OH-PBDEs). Environmental Science and Pollution Research International, 15(7): 606–613

[39] Mukherjee R, Kumar R, Sinha A, Lama Y, Saha A K (2016). A review on synthesis, characterization, and applications of nano zero valent iron (nZVI) for environmental remediation. Critical Reviews in Environmental Science and Technology, 46(5): 443–466

[40] Nasuha N, Ismail S, Hameed B H (2017). Activated electric arc furnace slag as an effective and reusable Fenton-like catalyst for the photodegradation of methylene blue and acid blue 29. Journal of Environmental Management, 196: 323–329

[41] Rivero-Huguet M, Marshall W D (2009). Influence of various organic molecules on the reduction of hexavalent chromium mediated by zero-valent iron. Chemosphere, 76(9): 1240–1248

[42] Salter-Blanc A J, Tratnyek P G (2011). Effects of solution chemistry on the dechlorination of 1,2,3-trichloropropane by zero-valent zinc. Environmental Science & Technology, 45(9): 4073–4079

[43] Santos M S F, Alves A, Madeira L M (2016). Chemical and photochemical degradation of polybrominated diphenyl ethers in liquid systems: A review. Water Research, 88: 39–59

[44] Sayilgan E, Kukrer T, Yigit N, Civelekoglu G, Kitis M (2010). Acidic leaching and precipitation of zinc and manganese from spent battery powders using various reductants. Journal of Hazardous Materials, 173(1–3): 137–143

[45] Schwertmann U (1991). Solubility and dissolution of iron oxides. Plant and Soil, 130(1–2): 1–25

[46] Sellström U, Kierkegaard A, De Wit C, Jansson B (1998). Polybrominated diphenyl ethers and hexabromocyclododecane in sediment and fish from a Swedish River. Environmental Toxicology and Chemistry, 17(6): 1065–1072

[47] Shi J, Qu R, Feng M, Wang X, Wang L, Yang S, Wang Z (2015). Oxidative degradation of decabromodiphenyl ether (BDE 209) by potassium permanganate: reaction pathways, kinetics, and mechanisms assisted by density functional theory calculations. Environmental Science & Technology, 49(7): 4209–4217

[48] Sjodin A (2003). A review on human exposure to brominated flame retardants?particularly polybrominated diphenyl ethers. Environment International, 29(6): 829–839

[49] Soltermann F, Abegglen C, Tschui M, Stahel S, Von Gunten U (2017). Options and limitations for bromate control during ozonation of wastewater. Water Research, 116: 76–85

[50] Song H, Carraway E R, Kim Y H, Batchelor B, Jeon B H, Kim J G (2008). Amendment of hydroxyapatite in reduction of tetrachloroethylene by zero-valent zinc: Its rate enhancing effect and removal of Zn(II). Chemosphere, 73(9): 1420–1427

[51] Song W L, Ford J C, Li A, Mills W J, Buckley D R, Rockne K J (2004). Polybrominated diphenyl ethers in the sediments of the great lakes. 1. Lake superior. Environmental Science & Technology, 38(12): 3286–3293

[52] Stiborova H, Vrkoslavova J, Pulkrabova J, Poustka J, Hajslova J, Demnerova K (2015). Dynamics of brominated flame retardants removal in contaminated wastewater sewage sludge under anaerobic conditions. Science of the Total Environment, 533: 439–445

[53] Stone A T, Morgan J J (1984). Reduction and dissolution of manganese(III) and manganese(IV) oxides by organics: 2. Survey of the reactivity of organics. Environmental Science & Technology, 18(8): 617–624

[54] Sun C, Zhao D, Chen C, Ma W, Zhao J (2009). TiO₂-mediated photocatalytic debromination of decabromodiphenyl ether: kinetics and intermediates. Environmental Science & Technology, 43(1): 157–162

[55] Tomy G, Tittlemier S, Braekevelt E, Halldorson T, Stern G (2001).The physico-chemical properties of some brominated flame retardants. In: First International Workshop on Brominated Flames Retardants, Stockholm, Sweden. Stockholm: Stockholm University

[56] Vonderheide A P, Mueller K E, Meija J, Welsh G L (2008). Polybrominated diphenyl ethers: Causes for concern and knowledge gaps regarding environmental distribution, fate and toxicity. Science of the Total Environment, 400(1–3): 425–436

[57] Wang C, Lin Z, Dong Q, Lin Z, Lin K, Wang J, Huang J, Huang X, He Y, Huang C, Yang D, Huang C (2012). Polybrominated diphenyl ethers (PBDEs) in human serum from Southeast China. Ecotoxicology and Environmental Safety, 78: 206–211

[58] Wang R, Lu G, Lin H, Huang K, Tang T, Xue X, Yang X, Yin H, Dang Z (2017). Relative roles of H-atom transfer and electron transfer in the debromination of polybrominated diphenyl ethers by palladized nanoscale zerovalent iron. Environmental Pollution, 222: 331–337

[59] Wang R, Tang T, Lu G, Huang K, Chen M, Tao X, Yin H, Dang Z (2018a). Formation and degradation of polybrominated dibenzofurans (PBDFs) in the UV photolysis of polybrominated diphenyl ethers (PBDEs) in various solutions. Chemical Engineering Journal, 337: 333–341

[60] Wang R, Tang T, Xie J, Tao X, Huang K, Zou M, Yin H, Dang Z, Lu G (2018b). Debromination of polybrominated diphenyl ethers (PBDEs) and their conversion to polybrominated dibenzofurans (PBDFs) by UV light: Mechanisms and pathways. Journal of Hazardous Materials, 354: 1–7

[61] Wang X, Du Y, Liu H, Ma J(2018c). Ascorbic acid/Fe⁰ composites as an effective persulfate activator for improving the degradation of rhodamine B. RSC Advances, 8(36): 20275–20276

[62] Wang X,Lian W, Sun X, Ma J, Ning P (2018d). Immobilization of NZVI in polydopamine surface-modified biochar for adsorption and degradation of tetracycline in aqueous solution. Frontiers of Environmental Science & Engineering, 12(4): 9

[63] Watanabe I (2003). Environmental release and behavior of brominated flame retardants. Environment International, 29(6): 665–682

[64] Wei G, Zhang J, Luo J, Xue H, Huang D,Cheng Z, Jiang X (2019). Nanoscale zero-valent iron supported on biochar for the highly efficient removal of nitrobenzene. Frontiers of Environmental Science & Engineering, 13(4): 61

[65] Wu D, Song K, Fang Z, Long Gu F (2013). Theoretical investigation on debromination model of deca-bromodiphenyl ester (BDE209). Current Physical Chemistry, 3(2): 179–186

[66] Wu J, Yi Y, Li Y, Fang Z, Tsang E P (2016). Excellently reactive Ni/Fe bimetallic catalyst supported by biochar for the remediation of decabromodiphenyl contaminated soil: Reactivity, mechanism, pathways and reducing secondary risks. Journal of Hazardous Materials, 320: 341–349

[67] Xue X, Hanna K, Despas C, Wu F, Deng N (2009). Effect of chelating agent on the oxidation rate of PCP in the magnetite/H₂O₂ system at neutral pH. Journal of Molecular Catalysis A. Chemical, 311(1–2): 29–35

[68] Yang B, Deng J, Wei L, Han Y, Yu G, Deng S, Zhu C, Duan H, Zhuo Q (2018). Synergistic effect of ball-milled Al micro-scale particles with vitamin B12 on the degradation of 2,2′4,4′-tetrabromodiphenyl ether in liquid system. Chemical Engineering Journal, 333: 613–620

[69] Yang B, Yu G, Huang J (2007). Electrocatalytic hydrodechlorination of 2, 4, 5-trichlorobiphenyl on a palladium-modified nickel foam cathode. Environmental Science & Technology, 41(21): 7503–7508

[70] Yin W, Zhang Y, Wang P, Zheng S, Zhu C, Han X, Zhang Q, Liang Y, Jiang G (2018). Distribution of polybrominated diphenyl ethers (PBDEs) in feather and muscle of the birds of prey from Beijing, China. Ecotoxicology and Environmental Safety, 165: 343–348

[71] Zezza D, Tait S, Della Salda L, Amorena M, Merola C, Perugini M (2019). Toxicological, gene expression and histopathological evaluations of environmentally realistic concentrations of polybrominated diphenyl ethers PBDE-47, PBDE-99 and PBDE-209 on zebrafish embryos. Ecotoxicology and Environmental Safety, 183: 109566

[72] Zhai C, Peng S, Yang L, Wang Q (2014). Evaluation of BDE-47 hydroxylation metabolic pathways based on a strong electron-withdrawing pentafluorobenzoyl derivatization gas chromatography/electron capture negative ionization quadrupole mass spectrometry. Environmental Science & Technology, 48(14): 8117–8126

[73] Zhang M, Lu J, Xu Z, He Y, Zhang B, Jin S, Boman B (2015). Removing polybrominated diphenyl ethers in pure water using Fe/Pd bimetallic nanoparticles. Frontiers of Environmental Science & Engineering, 9(5): 832–839

[74] Zhang X, Gu X, Lu S, Brusseau M L, Xu M, Fu X, Qiu Z, Sui Q (2017). Application of ascorbic acid to enhance trichloroethene degradation by Fe(III)-activated calcium peroxide. Chemical Engineering Journal, 325: 188–198

[75] Zhao C, Yan M, Zhong H, Liu Z, Shi L, Chen M, Zeng G, Song B, Shao B, Feng H (2018). Biodegradation of polybrominated diphenyl ethers and strategies for acceleration: A review. International Biodeterioration & Biodegradation, 129: 23–32

[76] Zhuang Y, Ahn S, Luthy R G (2010). Debromination of polybrominated diphenyl ethers by nanoscale zerovalent iron: pathways, kinetics, and reactivity. Environmental Science & Technology, 44(21): 8236–8242

[77] Zhuang Y, Ahn S, Seyfferth A L, Masue-Slowey Y, Fendorf S, Luthy R G (2011). Dehalogenation of polybrominated diphenyl ethers and polychlorinated biphenyl by bimetallic, impregnated, and nanoscale zerovalent iron. Environmental Science & Technology, 45(11): 4896–4903

[78] Zhuang Y, Jin L, Luthy R G (2012). Kinetics and pathways for the debromination of polybrominated diphenyl ethers by bimetallic and nanoscale zerovalent iron: Effects of particle properties and catalyst. Chemosphere, 89(4): 426–432

[79] Zumreoglukaran B (2006). The coordination chemistry of Vitamin C: An overview. Coordination Chemistry Reviews, 250(17–18): 2295–2307

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