Identification and Toxicity Prediction of Biotransformation Molecules of Organophosphate Flame Retardants by Microbial Reactions in a Wastewater Treatment Plant
Abstract
:1. Introduction
2. Results
2.1. Quality Assurance and Quality Control (QAQC)
2.2. Concentration of Organophosphate Flame Retardants in Wastewater Treatment Plant
2.3. Identification of Biotransformation Products from Organophosphate Flame Retardants
2.3.1. Tris(2-butoxyethyl) Phosphate
2.3.2. Tris(1-chloro-2-propyl) Phosphate
2.3.3. Triphenyl Phosphate
2.4. Ecotoxicological Information of Biotransformation Products in Microorganisms
3. Discussion
4. Materials and Methods
4.1. Chemicals and Reagents
4.2. Information on the Wastewater Treatment Plant
4.3. Sample Preparation
4.4. Chemical Analysis
4.5. Toxicity Prediction
5. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
Abbreviations
BTPs | biotransformation products |
MDL | method detection limit |
OPFRs | organophosphate flame retardants |
TBEP | tris(2-butoxyethyl) phosphate |
TCPP | tris(1-chloro-2-propyl) phosphate |
TPHP | triphenyl phosphate |
WWTP | wastewater treatment plant |
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OPFRs | Influent [μg/L] | Biological Reactor [μg/L] | Effluent [μg/L] | Removal Rate (%) |
---|---|---|---|---|
TBEP | 2.55 | 1.24 | 1.09 | 57.3 |
TCPP | 0.13 | 0.24 | 0.27 | None |
TPHP | 0.021 | 0.019 | 0.017 | 19.0 |
Compound a | Formula | Mass of [M+H]+ or [M-H]− | Retention Time (min) | Formula Change | Biotransformation |
---|---|---|---|---|---|
TBEP | C18H39O7P | [M + H]+: 399.25062 | 12.76 | Parent compound | |
TB_88 | C4H8O2 | [M − H]−: 87.04515 | 9.26 | − C12H31O5P | Oxidation (2) |
TB_198 | C6H15O5P | [M + H]+: 199.07299 | 5.66 | − C12H24O2 | Hydrolysis (2) |
TB_298 | C12H27O6P | [M + H]+: 299.16180 | 11.15 | − C6H12O | Hydrolysis |
TB_412 | C18H37O8P | [M + H]+: 413.22988 | 9.38 | − H2 + O | Oxidation (2) |
TB_414 | C18H39O8P | [M + H]+: 415.24553 | 9.34, 9.68 | + O | Oxidation |
TCPP | C9H18Cl3O4P | [M + H]+: 327.00811 | 8.62 | Parent compound | |
TC_90 | C3H6O3 | [M − H]−: 89.02441 | 16.45 | − C6H12Cl3OP | Oxidative dechlorination (3),Hydrolysis |
TC_249 | C6H13Cl2O4P | [M + H]+: 251.00013 | 8.64 | − C3H5Cl | Hydrolysis |
TC_290 | C9H20ClO6P | [M − H]−: 289.06132 | 4.95 | − Cl2 + H2O2 | Oxidative dechlorination (2) |
TC_304 | C9H18ClO7P | [M − H]−: 303.04059 | 9.08 | − Cl2 + O3 | Oxidative dechlorination (2),Oxidation (2) |
TPHP | C18H15O4P | [M + H]+: 327.07807 | 10.89 | Parent compound | |
TP_110 | C6H6O2 | [M − H]−: 109.02950 | 3.61 | − C12H9O2P | Hydrolysis (2) |
TP_138 | C7H6O3 | [M − H]−: 137.02440 | 2.47 | − C11H9OP | Hydrolysis, Carboxylation |
TP_140 | C7H8O3 | [M + H]+: 141.05460 | 2.48 | − C11H7OP | Hydrolysis (2), Reduction (2),Oxidation, Carboxylation |
TP_188 | C7H8O6 | [M + H]+: 189.03940 | 4.98 | − C11H7P + O2 | Hydrolysis, Oxidation (2), Reduction (2), Carboxylation |
TP_250 | C12H11O4P | [M − H]−: 249.03222 | 6.27 | − C6H4 | Hydrolysis |
TP_342 | C18H15O5P | [M + H]+: 343.07299 | 9.01 | + O | Oxidation |
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Choi, Y.; Kim, S.D. Identification and Toxicity Prediction of Biotransformation Molecules of Organophosphate Flame Retardants by Microbial Reactions in a Wastewater Treatment Plant. Int. J. Mol. Sci. 2021, 22, 5376. https://doi.org/10.3390/ijms22105376
Choi Y, Kim SD. Identification and Toxicity Prediction of Biotransformation Molecules of Organophosphate Flame Retardants by Microbial Reactions in a Wastewater Treatment Plant. International Journal of Molecular Sciences. 2021; 22(10):5376. https://doi.org/10.3390/ijms22105376
Chicago/Turabian StyleChoi, Yeowool, and Sang Don Kim. 2021. "Identification and Toxicity Prediction of Biotransformation Molecules of Organophosphate Flame Retardants by Microbial Reactions in a Wastewater Treatment Plant" International Journal of Molecular Sciences 22, no. 10: 5376. https://doi.org/10.3390/ijms22105376