Development of methods based on low-temperature partitioning (LTP) for monitoring cresols and chlorophenols in sewage sludge, soil, and water in column leaching

References

• Hoang, S. A.; Bolan, N.; Madhubashani, A. M. P.; Vithanage, M.; Perera, V.; Wijesekara, H.; Wang, H.; Srivastava, P.; Kirkham, M. B.; Mickan, B. S.; et al. Treatment Processes to Eliminate Potential Environmental Hazards and Restore Agronomic Value of Sewage Sludge: A Review. Environ. Pollut. 2022, 293, 118564–118582. DOI: 10.1016/j.envpol.2021.118564.
   PubMed Web of Science ®Google Scholar
• Steele, J. C.; Meng, X. Z.; Venkatesan, A. K.; Halden, R. U. Comparative Meta-Analysis of Organic Contaminants in Sewage Sludge from the United States and China. Sci. Total Environ. 2022, 821, 153423–153433. DOI: 10.1016/j.scitotenv.2022.153423.
   PubMed Web of Science ®Google Scholar
• National Council for the Environment (CONAMA). Resolution No 375/2006. Defines Criteria and Procedures for the Agricultural Use of Sewage Sludge Generated in Sewage Treatment Plants and Their Derivate Products, and Makes Other Provisions. Environment Ministry. 2006. http://www.mma.gov.br/port/conama/res/res06/res37506.pdf.
   Google Scholar
• Agency for Toxic Substances and Disease Registry (ATSDR). Substance Priority List; U. S. Department of Health and Human Services: Atlanta, GA, 2017. http://www.atsdr.cdc.gov/spl/#2017spl.
   Google Scholar
• Bai, Y.; Yan, L.; Li, G.; Zhao, R.; Li, F. Effects of Demineralization on Phenols Distribution and Formation during Coal Pyrolysis. Fuel 2014, 134, 368–374. DOI: 10.1016/j.fuel.2014.05.076.
   Web of Science ®Google Scholar
• Harzallah, B.; Grama, S. B.; Bousseboua, H.; Jouanneau, Y.; Yang, J.; Li, J. Isolation and Characterization of Indigenous Bacilli Strains from an Oil Refinery Wastewater with Potential Applications for Phenol/Cresol Bioremediation. J. Environ. Manag. 2023, 332, 117322–117331. DOI: 10.1016/j.jenvman.2023.117322.
   PubMed Web of Science ®Google Scholar
• Duan, W.; Meng, F.; Cui, H.; Lin, Y.; Wang, G.; Wu, J. Ecotoxicity of Phenol and Cresols to Aquatic Organisms: A Review. Ecotoxicol. Environ. Saf. 2018, 157, 441–456. DOI: 10.1016/j.ecoenv.2018.03.089.
   PubMed Web of Science ®Google Scholar
• Yang, Y.; Li, X.; Zhu, H.; Xu, X.; Bao, L. Chemical Removal of m-Cresol: A Critical Review. Rev. Chem. Eng. 2022, 38, 1023–1044. DOI: 10.1515/revce-2021-0001.
   Web of Science ®Google Scholar
• Badanthadka, M.; Mehendale, H. M. Cresols. In Encyclopedia of Toxicology, 3rd ed.; Cambridge: Elsevier, 2014.
   Google Scholar
• Asmadi, M.; Kawamoto, H.; Saka, S. Gas- and Solid/Liquid-Phase Reactions during Pyrolysis of Softwood and Hardwood Lignins. J. Anal. Appl. Pyrolysis 2011, 92, 417–425. DOI: 10.1016/j.jaap.2011.08.003.
   Web of Science ®Google Scholar
• Zhang, H.; Zhao, F.; Liu, Y.; Li, Y.; Liu, H.; Sun, H. Assessment of the Inhibition Risk of Chlorophenol Substances on Cytochrome P450 via Cocktail Inhibition Assays. Toxicol. Appl. Pharmacol. 2023, 461, 116401–116412. DOI: 10.1016/j.taap.2023.116401.
   PubMed Web of Science ®Google Scholar
• Olaniran, A. O.; Igbinosa, E. O. Chlorophenols and Other Related Derivatives of Environmental Concern: Properties, Distribution and Microbial Degradation Processes. Chemosphere 2011, 83, 1297–1306. DOI: 10.1016/j.chemosphere.2011.04.009.
   PubMed Web of Science ®Google Scholar
• Ahlborg, U. G.; Thunberg, T. M. Chlorinated Phenols – Occurrence, Toxicity, Metabolism, and Environmental-Impact. Crit. Rev. Toxicol. 1980, 7, 1–35. DOI: 10.3109/10408448009017934.
   PubMed Web of Science ®Google Scholar
• Aken, P. V.; Lambert, N. R.; Broeck, V.; Degrève, J.; Dewil, R. Advances in Ozonation and Biodegradation Processes to Enhance Chlorophenol Abatement in Multisubstrate Wastewaters: A Review. Environ. Sci. Water Res. Technol. 2019, 5, 444–482.
   Google Scholar
• Pera-Titus, M.; Garcı́a-Molina, V.; Baños, M. A.; Giménez, J.; Esplugas, Sant. i. ago Degradation of chlorophenols by Means of Advanced Oxidation Processes: A General Review. Appl. Catal. B Environ. 2004, 47, 219–256. DOI: 10.1016/j.apcatb.2003.09.010.
   Web of Science ®Google Scholar
• Salcedo, G. M.; Kupski, L.; Degang, L.; Marube, L. C.; Caldas, S. S.; Primel, E. G. Determination of Fifteen Phenols in Wastewater from Petroleum Refinery Samples Using a Dispersive Liquid-Liquid Microextraction and Liquid Chromatography with a Photodiode Array Detector. Microchem. J. 2019, 146, 722–728. DOI: 10.1016/j.microc.2019.01.075.
   Web of Science ®Google Scholar
• Llompart, M.; Lourido, M.; Landin, P.; García-Jares, C.; Cela, R. Optimization of a Derivatization-Solid-Phase Microextraction Method for the Analysis of Thirty Phenolic Pollutants in Water Samples. J. Chromatogr. A 2002, 963, 137–148. DOI: 10.1016/s0021-9673(02)00646-5.
   PubMed Web of Science ®Google Scholar
• Padilla-Sánchez, J. A.; Plaza-Bolanos, P.; Romero-González, R.; Garrido-Frenich, A.; Vidal, J. L. M. Application of a Quick, Easy, Cheap, Effective, Rugged and Safe-Based Method for the Simultaneous Extraction of Chlorophenols, Alkylphenols, Nitrophenols and Cresols in Agricultural Soils, Analyzed by Using Gas Chromatography-Triple Quadrupole-Mass Spectrometry/Mass Spectrometry. J. Chromatogr. A 2010, 1217, 5724–5731. DOI: 10.1016/j.chroma.2010.07.004.
   PubMed Web of Science ®Google Scholar
• Maia, M. R.; Arcanjo, A. L. P.; Pinho, G. P.; Silverio, F. O. Solid-Liquid Extraction with Low Temperature Purification Coupled with Gas Chromatography and Mass Spectrometry for Determination of Polychlorinated Biphenyls in Sewage Sludge. J. Braz. Chem. Soc. 2017, 28, 179–186.
   Web of Science ®Google Scholar
• Oliveira, C. I.; Cardoso, A. T.; Goulart, A. C.; Oliveira, M. A. C.; Santos, J. P. V.; Goulart, S. M. Determination of Pesticides in Soybean Seeds Incorrectly Discarded near a Spring of the Paranaiba River, GO-Brazil. Chem. Biodivers. 2022, 19, 202100560–202100568.
   Web of Science ®Google Scholar
• Freitas, J. F.; Queiroz, M. E. L. R.; Oliveira, A. F.; Ribeiro, L. P.; Salvador, D. V.; Miranda, L. D. L.; Alves, R. R.; Rodrigues, A. A. Z. Evaluation of Imazalil Dissipation/Migration in Postharvest Papaya Using Low-Temperature Partition Extraction and GC–MS Analysis. Food Chem. 2023, 418, 135969–135977. DOI: 10.1016/j.foodchem.2023.135969.
   PubMed Web of Science ®Google Scholar
• Goulart, S. M.; Alves, R. D.; Neves, A. A.; de Queiroz, J. H.; Assis, T. C.; de Queiroz, M. E. L. R. Optimization and Validation of Liquid-Liquid Extraction with Low Temperature Partitioning for Determination of Carbamates in Water. Anal. Chim. Acta 2010, 671, 41–47. DOI: 10.1016/j.aca.2010.05.003.
   PubMed Web of Science ®Google Scholar
• Cunha, C. C. R. F.; Freitas, M.; Gomes, R.; Silva, D. A.; Barros, A. L. C.; Ribeiro, M. C.; Sanson, A. L.; Afonso, R. J. C. F. Low-Temperature Partitioning Extraction Followed by Liquid Chromatography Tandem Mass Spectrometry Determination of Multiclass Antibiotics in Solid and Soluble Wastewater Fractions. J. Chromatogr. A 2021, 1650, 462256–462267. DOI: 10.1016/j.chroma.2021.462256.
   PubMed Web of Science ®Google Scholar
• Barros, A. L. C.; Abreu, C. G.; Cunha, C. C. R. F.; Rodrigues, D. A. S.; Afonso, R. J. C. F.; SiLVa, G. A. Method Development for Simultaneous Determination of Polar and Nonpolar Pesticides in Surface Water by Low-Temperature Partitioning Extraction (LTPE) Followed by HPLC-ESI-MS/MS. Environ. Sci. Pollut. Res. Int. 2019, 26, 31609–31622. DOI: 10.1007/s11356-019-06286-5.
   PubMed Web of Science ®Google Scholar
• Jackson, D. R.; Garrett, B. C.; Bishop, T. A. Comparison of Batch and Column Methods for Assessing Leachability of Hazardous Waste. Environ. Sci. Technol. 1984, 18, 668–673. DOI: 10.1021/es00127a007.
   Web of Science ®Google Scholar
• Enell, A.; Reichenberg, F.; Warfvinge, P.; Ewald, G. A Column Method for Determination of Leaching of Polycyclic Aromatic Hydrocarbons from Aged Contaminated Soil. Chemosphere 2004, 54, 707–715. DOI: 10.1016/j.chemosphere.2003.08.026.
   PubMed Web of Science ®Google Scholar
• Bauw, D. H.; de Wilde, P. G. M.; Rood, G. A.; Aalbers, T. A Standard Leaching Test, Including Solid-Phase Extraction, for the Determination of PAH Leachability from Waste Materials. Chemosphere 1991, 22, 713–722. DOI: 10.1016/0045-6535(91)90048-I.
   Web of Science ®Google Scholar
• Lopez-Avila, V.; Milanes, J.; Constantine, F.; Beckert, W. F. Typical Phthalate Ester Contamination Incurred Using EPA Method 8060. J. AOAC Intern. 1990, 73, 709–720. DOI: 10.1093/jaoac/73.5.709.
   Google Scholar
• National Institute of Metrology Standardization and Quality (INMETRO). Guidance on Validation of Analytical Methods, DOQCGCRE-008; 2020. http://www.inmetro.gov.br/Sidoq/Arquivos/Cgcre/DOQ/DOQ-Cgcre-8_08.pdf.
   Google Scholar
• Thompson, M.; Ellison, S. L. R.; Wood, R. Harmonized Guidelines for Single-Laboratory Validation of Methods of Analysis (IUPAC Technical Report). Pure Appl. Chem. 2002, 74, 835–855. DOI: 10.1351/pac200274050835.
   Web of Science ®Google Scholar
• De Souza, S. V. C.; Junqueira, R. G. A Procedure to Assess Linearity by Ordinary Least Squares Method. Anal. Chim. Acta 2005, 552, 25–35. DOI: 10.1016/j.aca.2005.07.043.
   Web of Science ®Google Scholar
• Faludi, T.; Andrasi, N.; Vasanits-Zsigrai, A.; Záray, G.; Molnar-Perl, I. Systematic Derivatization, Mass Fragmentation and Acquisition Studies in the Analysis of Chlorophenols, as Their Silyl Derivatives by Gas Chromatography-Mass Spectrometry. J. Chromatogr. A 2013, 1302, 133–142. DOI: 10.1016/j.chroma.2013.06.004.
   PubMed Web of Science ®Google Scholar
• Cai, K.; Zhao, Y.; Kang, Z.; Wang, S.; Wright, A. L.; Jiang, X. Environmental Pseudotarget Metabolomics: A High Throughput and Wide Coverage Method for Metabolic Profiling of 1000-Year Paddy Soil Chronosequences. Sci. Total Environ. 2023, 858, 159978–159990. DOI: 10.1016/j.scitotenv.2022.159978.
   PubMed Web of Science ®Google Scholar
• Ramalho, M. B.; Duraes, A. F. S.; Silvério, F. O.; Pinho, G. P. Determination of Three Cresol Isomers in Sewage Sludge by Solid-Liquid Extraction with Low Temperature Purification and Gas Chromatography-Mass Spectrometry. J. Environ. Sci. Health B 2020, 55, 184–192. DOI: 10.1080/03601234.2019.1678952.
   PubMed Web of Science ®Google Scholar
• Rudakov, O. B.; Khorokhordina, E. A.; Reobrazhenskii, M. A. P.; Rudakova, L. V. Low-Temperature Liquid–Liquid Extraction of Phenols from Aqueous Solutions with Hydrophilic Mixtures of Extractants. Russ. J. Phys. Chem. 2016, 90, 1665–1668. DOI: 10.1134/S0036024416080264.
   Web of Science ®Google Scholar
• Fewson, C. A. Biodegradation of Xenobiotic and Other Persistent Compounds: The Causes of Recaucitrance. Trends Biotechnol. 1988, 6, 148–153. DOI: 10.1016/0167-7799(88)90084-4.
   Web of Science ®Google Scholar
• Nascimento, A. L.; Souza, A. J.; Andrade, P. A. M.; Andreote, F. D.; Coscione, A. R.; Oliveira, F. C.; Regitano, J. B. Sewage Sludge Microbial Structures and Relations to Their Sources, Treatments, and Chemical Attributes. Front. Microbiol. 2018, 9, 1462–1473. DOI: 10.3389/fmicb.2018.01462.
   PubMed Web of Science ®Google Scholar
• Lopez-Echartea, E.; Strejcek, M.; Mateju, V.; Vosahlova, S.; Kyclt, R.; Demnerova, Kat. e. r.; Uhlik, O. Bioremediation of Chlorophenol-Contaminated Sawmill Soil Using Pilot-Scale Bioreactors under Consecutive Anaerobic-Aerobic Conditions. Chemosphere 2019, 227, 670–680. DOI: 10.1016/j.chemosphere.2019.04.036.
   PubMed Web of Science ®Google Scholar
• Yan, J. B.; Xu, L. L.; Wei, X. Biodegradation Characteristics and Bioaugmentation Potential of an Efficient o-Cresol-Degrading Strain Isolated Strain Isolated from Petrochemical Sewage Treatment Plant. Adv. Mat. Res. 2013, 726–731, 264–268.
   Google Scholar
• Bera, S.; Kauser, H.; Mohanty, K. Optimization of p-Cresol Biodegradation Using Novel Bacterial Strains Isolated from Petroleum Hydrocarbon Fallout. J. Water Process. Eng. 2019, 31, 100842–100848. DOI: 10.1016/j.jwpe.2019.100842.
   Web of Science ®Google Scholar
• Rodrigues, V. S.; Andrade, L. M.; Tenório, J. A. S. Biodegradation of Phenolic Compounds in Waste Foundry Sand: Physical and Chemical Characterization of Foundry Sand and Bacterial Degradation Kinetics. Environ. Nanotechnol. Monit. Manag. 2021, 16, 1–7.
   Google Scholar
• Lallai, A.; Mura, G. A. Biodegradation of 2-Chlorophenol in Forest Soil: Effect of Inoculation with Aerobic Sewage Sludge. Environ. Toxicol. Chem. 2004, 23, 325–330. DOI: 10.1897/02-419.
   PubMed Web of Science ®Google Scholar