Valoration of the Synthetic Antioxidant Tris-(Diterbutyl-Phenol)-Phosphite (Irgafos P-168) from Industrial Wastewater and Application in Polypropylene Matrices to Minimize Its Thermal Degradation
Industrial wastewater from petrochemical processes is an essential source of the synthetic phenolic phosphite antioxidant (Irgafos P-168), which negatively affects the environment. For the determination and analysis of Irgafos P-168, DSC, HPLC-MS, and FTIR methodologies were used. Solid phase extrac...
- Autores:
-
Hernández-Fernández, Joaquín
Cano, Heidis
Reyes, Ana Fonseca
- Tipo de recurso:
- Fecha de publicación:
- 2023
- Institución:
- Universidad Tecnológica de Bolívar
- Repositorio:
- Repositorio Institucional UTB
- Idioma:
- eng
- OAI Identifier:
- oai:repositorio.utb.edu.co:20.500.12585/12157
- Acceso en línea:
- https://hdl.handle.net/20.500.12585/12157
- Palabra clave:
- Valoration
Synthetic antioxidant
Irgafos P-168
Industrial wastewater
Polypropylene
Thermal degradation
- Rights
- openAccess
- License
- http://creativecommons.org/licenses/by-nc-nd/4.0/
id |
UTB2_97ba4999cc1c10a1828f9644313004fc |
---|---|
oai_identifier_str |
oai:repositorio.utb.edu.co:20.500.12585/12157 |
network_acronym_str |
UTB2 |
network_name_str |
Repositorio Institucional UTB |
repository_id_str |
|
dc.title.spa.fl_str_mv |
Valoration of the Synthetic Antioxidant Tris-(Diterbutyl-Phenol)-Phosphite (Irgafos P-168) from Industrial Wastewater and Application in Polypropylene Matrices to Minimize Its Thermal Degradation |
title |
Valoration of the Synthetic Antioxidant Tris-(Diterbutyl-Phenol)-Phosphite (Irgafos P-168) from Industrial Wastewater and Application in Polypropylene Matrices to Minimize Its Thermal Degradation |
spellingShingle |
Valoration of the Synthetic Antioxidant Tris-(Diterbutyl-Phenol)-Phosphite (Irgafos P-168) from Industrial Wastewater and Application in Polypropylene Matrices to Minimize Its Thermal Degradation Valoration Synthetic antioxidant Irgafos P-168 Industrial wastewater Polypropylene Thermal degradation |
title_short |
Valoration of the Synthetic Antioxidant Tris-(Diterbutyl-Phenol)-Phosphite (Irgafos P-168) from Industrial Wastewater and Application in Polypropylene Matrices to Minimize Its Thermal Degradation |
title_full |
Valoration of the Synthetic Antioxidant Tris-(Diterbutyl-Phenol)-Phosphite (Irgafos P-168) from Industrial Wastewater and Application in Polypropylene Matrices to Minimize Its Thermal Degradation |
title_fullStr |
Valoration of the Synthetic Antioxidant Tris-(Diterbutyl-Phenol)-Phosphite (Irgafos P-168) from Industrial Wastewater and Application in Polypropylene Matrices to Minimize Its Thermal Degradation |
title_full_unstemmed |
Valoration of the Synthetic Antioxidant Tris-(Diterbutyl-Phenol)-Phosphite (Irgafos P-168) from Industrial Wastewater and Application in Polypropylene Matrices to Minimize Its Thermal Degradation |
title_sort |
Valoration of the Synthetic Antioxidant Tris-(Diterbutyl-Phenol)-Phosphite (Irgafos P-168) from Industrial Wastewater and Application in Polypropylene Matrices to Minimize Its Thermal Degradation |
dc.creator.fl_str_mv |
Hernández-Fernández, Joaquín Cano, Heidis Reyes, Ana Fonseca |
dc.contributor.author.none.fl_str_mv |
Hernández-Fernández, Joaquín Cano, Heidis Reyes, Ana Fonseca |
dc.subject.keywords.spa.fl_str_mv |
Valoration Synthetic antioxidant Irgafos P-168 Industrial wastewater Polypropylene Thermal degradation |
topic |
Valoration Synthetic antioxidant Irgafos P-168 Industrial wastewater Polypropylene Thermal degradation |
description |
Industrial wastewater from petrochemical processes is an essential source of the synthetic phenolic phosphite antioxidant (Irgafos P-168), which negatively affects the environment. For the determination and analysis of Irgafos P-168, DSC, HPLC-MS, and FTIR methodologies were used. Solid phase extraction (SPE) proved to be the best technique for extracting Irgafos from wastewater. HPLC-MS and SPE determined the repeatability, reproducibility, and linearity of the method and the SPE of the standards and samples. The relative standard deviations, errors, and correlation coefficients for the repeatability and reproducibility of the calibration curves were less than 4.4% and 4.2% and greater than 0.99955, respectively. The analysis of variance (ANOVA), using the Fisher method with confidence in 95% of the data, did not reveal significant differences between the mentioned parameters. The removal of the antioxidant from the wastewater by SPE showed recovery percentages higher than 91.03%, and the chemical characterization of this antioxidant by FTIR spectroscopy, DSC, TGA, and MS showed it to be structurally the same as the Irgafos P-168 molecule. The recovered Irgafos was added to the polypropylene matrix, significantly improving its oxidation times. An OIT analysis, performed using DSC, showed that the recovered Irgafos-blended polypropylene (PP) demonstrated oxidative degradation at 8 min. With the addition of the Irgafos, the oxidation time was 13 min. This increases the polypropylene’s useful life and minimizes the environmental impact of the wastewater. |
publishDate |
2023 |
dc.date.accessioned.none.fl_str_mv |
2023-07-19T12:55:06Z |
dc.date.available.none.fl_str_mv |
2023-07-19T12:55:06Z |
dc.date.issued.none.fl_str_mv |
2023-04-02 |
dc.date.submitted.none.fl_str_mv |
2023-07 |
dc.type.coarversion.fl_str_mv |
http://purl.org/coar/version/c_b1a7d7d4d402bcce |
dc.type.coar.fl_str_mv |
http://purl.org/coar/resource_type/c_2df8fbb1 |
dc.type.driver.spa.fl_str_mv |
info:eu-repo/semantics/article |
dc.type.hasversion.spa.fl_str_mv |
info:eu-repo/semantics/draft |
dc.type.spa.spa.fl_str_mv |
http://purl.org/coar/resource_type/c_6501 |
status_str |
draft |
dc.identifier.citation.spa.fl_str_mv |
Hernández-Fernández, J.; Cano, H.; Reyes, A.F. Valoration of the Synthetic Antioxidant Tris-(Diterbutyl- henol)-Phosphite (Irgafos P-168) from Industrial Wastewater and Application in Polypropylene Matrices to Minimize Its Thermal Degradation. Molecules 2023, 28, 3163. https://doi.org/10.3390/molecules28073163 |
dc.identifier.uri.none.fl_str_mv |
https://hdl.handle.net/20.500.12585/12157 |
dc.identifier.doi.none.fl_str_mv |
10.3390/molecules28073163 |
dc.identifier.instname.spa.fl_str_mv |
Universidad Tecnológica de Bolívar |
dc.identifier.reponame.spa.fl_str_mv |
Repositorio Universidad Tecnológica de Bolívar |
identifier_str_mv |
Hernández-Fernández, J.; Cano, H.; Reyes, A.F. Valoration of the Synthetic Antioxidant Tris-(Diterbutyl- henol)-Phosphite (Irgafos P-168) from Industrial Wastewater and Application in Polypropylene Matrices to Minimize Its Thermal Degradation. Molecules 2023, 28, 3163. https://doi.org/10.3390/molecules28073163 10.3390/molecules28073163 Universidad Tecnológica de Bolívar Repositorio Universidad Tecnológica de Bolívar |
url |
https://hdl.handle.net/20.500.12585/12157 |
dc.language.iso.spa.fl_str_mv |
eng |
language |
eng |
dc.rights.coar.fl_str_mv |
http://purl.org/coar/access_right/c_abf2 |
dc.rights.uri.*.fl_str_mv |
http://creativecommons.org/licenses/by-nc-nd/4.0/ |
dc.rights.accessrights.spa.fl_str_mv |
info:eu-repo/semantics/openAccess |
dc.rights.cc.*.fl_str_mv |
Attribution-NonCommercial-NoDerivatives 4.0 Internacional |
rights_invalid_str_mv |
http://creativecommons.org/licenses/by-nc-nd/4.0/ Attribution-NonCommercial-NoDerivatives 4.0 Internacional http://purl.org/coar/access_right/c_abf2 |
eu_rights_str_mv |
openAccess |
dc.format.extent.none.fl_str_mv |
21 páginas |
dc.format.medium.none.fl_str_mv |
Pdf |
dc.format.mimetype.spa.fl_str_mv |
application/pdf |
dc.publisher.place.spa.fl_str_mv |
Cartagena de Indias |
dc.publisher.sede.spa.fl_str_mv |
Campus Tecnológico |
dc.source.spa.fl_str_mv |
Molecules - Vol. 28 No. 7 (2023) |
institution |
Universidad Tecnológica de Bolívar |
bitstream.url.fl_str_mv |
https://repositorio.utb.edu.co/bitstream/20.500.12585/12157/1/molecules-28-03163.pdf https://repositorio.utb.edu.co/bitstream/20.500.12585/12157/2/license_rdf https://repositorio.utb.edu.co/bitstream/20.500.12585/12157/3/license.txt https://repositorio.utb.edu.co/bitstream/20.500.12585/12157/4/molecules-28-03163.pdf.txt https://repositorio.utb.edu.co/bitstream/20.500.12585/12157/5/molecules-28-03163.pdf.jpg |
bitstream.checksum.fl_str_mv |
fcf5d47dc5655b8b4db7f34717308a04 4460e5956bc1d1639be9ae6146a50347 e20ad307a1c5f3f25af9304a7a7c86b6 7d509922fd3d1c3b39c0ade2a4bb472a dcdcd50f17dee103d1133913fee22395 |
bitstream.checksumAlgorithm.fl_str_mv |
MD5 MD5 MD5 MD5 MD5 |
repository.name.fl_str_mv |
Repositorio Institucional UTB |
repository.mail.fl_str_mv |
repositorioutb@utb.edu.co |
_version_ |
1814021758657757184 |
spelling |
Hernández-Fernández, Joaquínbc85d77e-b89b-40f6-a090-a475dc6dc160Cano, Heidis9bed059b-3803-4c24-b13c-1500bcb79359Reyes, Ana Fonseca18625724-11b8-4d35-947b-4c7615f4dc5a2023-07-19T12:55:06Z2023-07-19T12:55:06Z2023-04-022023-07Hernández-Fernández, J.; Cano, H.; Reyes, A.F. Valoration of the Synthetic Antioxidant Tris-(Diterbutyl- henol)-Phosphite (Irgafos P-168) from Industrial Wastewater and Application in Polypropylene Matrices to Minimize Its Thermal Degradation. Molecules 2023, 28, 3163. https://doi.org/10.3390/molecules28073163https://hdl.handle.net/20.500.12585/1215710.3390/molecules28073163Universidad Tecnológica de BolívarRepositorio Universidad Tecnológica de BolívarIndustrial wastewater from petrochemical processes is an essential source of the synthetic phenolic phosphite antioxidant (Irgafos P-168), which negatively affects the environment. For the determination and analysis of Irgafos P-168, DSC, HPLC-MS, and FTIR methodologies were used. Solid phase extraction (SPE) proved to be the best technique for extracting Irgafos from wastewater. HPLC-MS and SPE determined the repeatability, reproducibility, and linearity of the method and the SPE of the standards and samples. The relative standard deviations, errors, and correlation coefficients for the repeatability and reproducibility of the calibration curves were less than 4.4% and 4.2% and greater than 0.99955, respectively. The analysis of variance (ANOVA), using the Fisher method with confidence in 95% of the data, did not reveal significant differences between the mentioned parameters. The removal of the antioxidant from the wastewater by SPE showed recovery percentages higher than 91.03%, and the chemical characterization of this antioxidant by FTIR spectroscopy, DSC, TGA, and MS showed it to be structurally the same as the Irgafos P-168 molecule. The recovered Irgafos was added to the polypropylene matrix, significantly improving its oxidation times. An OIT analysis, performed using DSC, showed that the recovered Irgafos-blended polypropylene (PP) demonstrated oxidative degradation at 8 min. With the addition of the Irgafos, the oxidation time was 13 min. This increases the polypropylene’s useful life and minimizes the environmental impact of the wastewater.21 páginasPdfapplication/pdfenghttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessAttribution-NonCommercial-NoDerivatives 4.0 Internacionalhttp://purl.org/coar/access_right/c_abf2Molecules - Vol. 28 No. 7 (2023)Valoration of the Synthetic Antioxidant Tris-(Diterbutyl-Phenol)-Phosphite (Irgafos P-168) from Industrial Wastewater and Application in Polypropylene Matrices to Minimize Its Thermal Degradationinfo:eu-repo/semantics/articleinfo:eu-repo/semantics/drafthttp://purl.org/coar/resource_type/c_6501http://purl.org/coar/version/c_b1a7d7d4d402bccehttp://purl.org/coar/resource_type/c_2df8fbb1ValorationSynthetic antioxidantIrgafos P-168Industrial wastewaterPolypropyleneThermal degradationCartagena de IndiasCampus TecnológicoHazarika, M.; Dixit, U.S.; Davim, J.P. History of Production and Industrial Engineering through Contributions of Stalwarts. Manuf. Eng. Educ. 2019, 1–29.Cao, L.; Lin, C.; Gao, Y.; Sun, C.; Xu, L.; Zheng, L.; Zhang, Z. Health risk assessment of trace elements exposure through the soil-plant (maize)-human contamination pathway near a petrochemical industry complex, Northeast China. Environ. Pollut. 2020, 263, 114414.Gebbink, W.A.; van Leeuwen, S.P. Environmental contamination and human exposure to PFASs near a fluorochemical production plant: Review of historic and current PFOA and GenX contamination in the Netherlands. Environ. Int. 2020, 137, 105583.Nie, M.; Nie, H.; He, M.; Lin, Y.; Wang, L.; Jin, P.; Zhang, S. Immobilization of biofilms of Pseudomonas aeruginosa NY3 and their application in the removal of hydrocarbons from highly concentrated oil-containing wastewater on the laboratory scale. J. Environ. Manag. 2016, 173, 34–40. [Kumar, L.; Chugh, M.; Kumar, S.; Kumar, K.; Sharma, J.; Bharadvaja, N. Remediation of petrorefinery wastewater contaminants: A review on physicochemical and bioremediation strategies. Process Saf. Environ. Prot. 2022, 159, 362–375. [CrossRef] 6. van Oosterhout, L.; Dijkstra, H.; Borst, D.; Duijndam, S.; Rehdanz, K.; van Beukering, P. Triggering sustainable plastics consumption behavior: Identifying consumer profiles across Europe and designing strategies to engage them. Sustain. Prod. Consum. 2023, 36, 148–160. [Pivato, A.F.; Miranda, G.M.; Prichula, J.; Lima, J.E.; Ligabue, R.A.; Seixas, A.; Trentin, D.S. Hydrocarbon-based plastics: Progress and perspectives on consumption and biodegradation by insect larvae. Chemosphere 2022, 293, 133600.Sridharan, S.; Kumar, M.; Saha, M.; Kirkham, M.; Singh, L.; Bolan, N.S. The polymers and their additives in particulate plastics: What makes them hazardous to the fauna? Sci. Total Environ. 2022, 824, 153828Marcato, B.; Guerra, S.; Vianello, M.; Scalia, S. Migration of antioxidant additives from various polyolefinic plastics into oleaginous vehicles. Int. J. Pharm. 2003, 257, 217–225Liao, B.; Ji, G.; Cheng, L. Profling of microbial communities in a bioreactor for treating hydrocarbon-sulfde-containing wastewater. J. Environ. Sci. 2008, 20, 897–899Goswami, L.; Manikandan, N.A.; Dolman, B.; Pakshirajan, K.; Pugazhenthi, G. Biological treatment of wastewater containing a mixture of polycyclic aromatic hydrocarbons using the oleaginous bacterium Rhodococcus opacus. J. Clean. Prod. 2018, 196, 1282–1291.Fernández, J.H.; Cano, H.; Guerra, Y.; Polo, E.P.; Ríos-Rojas, J.F.; Vivas-Reyes, R.; Oviedo, J. Identification and Quantification of Microplastics in Effluents of Wastewater Treatment Plant by Differential Scanning Calorimetry (DSC). Sustainability 2022, 14, 4920.Chaudhry, A.; Bashir, F.; Adil, S.F.; Saif, S.; Shaik, M.R.; Hatshan, M.R.; Shaik, B. Ascorbic acid-mediated Fe/Cu nanoparticles and their application for removal of COD and phenols from industrial wastewater. J. King Saud Univ.-Sci. 2022, 34, 101927their application for removal of COD and phenols from industrial wastewater. J. King Saud Univ.-Sci. 2022, 34, 101927. [CrossRef] 14. Lwanga, E.H.; van Roshum, I.; Munhoz, D.R.; Meng, K.; Rezaei, M.; Goossens, D.; Bijsterbosch, J.; Alexandre, N.; Oosterwijk, J.; Krol, M.; et al. Microplastic appraisal of soil, water, ditch sediment and airborne dust: The case of agricultural systems. Environ. Pollut. 2023, 316, 120513Franco, A.; Arellano, J.; Albendín, G.; Rodríguez-Barroso, R.; Quiroga, J.; Coello, M. Microplastic pollution in wastewater treatment plants in the city of Cádiz: Abundance, removal efficiency and presence in receiving water body. Sci. Total Environ. 2021, 776, 145795Hernández-Fernandez, J.; Rodríguez, E. Determination of phenolic antioxidants additives in industrial wastewater from polypropylene production using solid phase extraction with high-performance liquid chromatography. J. Chromatogr. A 2019, 1607, 460442Allen, N.S.; Edge, M.; Hussain, S. Perspectives on yellowing in the degradation of polymer materials: Inter-relationship of structure, mechanisms and modes of stabilisation. Polym. Degrad. Stab. 2022, 201, 109977.Cifuentes-Cabezas, M.; Mendoza-Roca, J.A.; Vincent-Vela, M.C.; Álvarez-Blanco, S. Management of reject streams from hybrid membrane processes applied to phenolic compounds removal from olive mill wastewater by adsorption/desorption and biological processes. J. Water Process Eng. 2022, 50, 103208.Alsabri, A.; Tahir, F.; Al-Ghamdi, S.G. Environmental impacts of polypropylene (PP) production and prospects of its recycling in the GCC region. Mater. Today Proc. 2021, 56, 2245–2251.Irshidat, M.R.; Al-Nuaimi, N.; Rabie, M. Hybrid effect of carbon nanotubes and polypropylene microfibers on fire resistance, thermal characteristics and microstructure of cementitious composites. Constr. Build. Mater. 2021, 266, 121154.Nascimento, E.M.D.; Eiras, D.; Pessan, L.A. Effect of thermal treatment on impact resistance and mechanical properties of polypropylene/calcium carbonate nanocomposites. Compos. Part B Eng. 2016, 91, 228–234. [Pavon, C.; Aldas, M.; López-Martínez, J.; Hernández-Fernández, J.; Arrieta, M. Films Based on Thermoplastic Starch Blended with Pine Resin Derivatives for Food Packaging. Foods 2021, 10, 1171.Joaquin, H.-F.; Juan, L.-M. Autocatalytic influence of different levels of arsine on the thermal stability and pyrolysis of polypropylene. J. Anal. Appl. Pyrolysis 2022, 161, 105385.Hernández-Fernández, J. Quantification of oxygenates, sulphides, thiols and permanent gases in propylene. A multiple linear regression model to predict the loss of efficiency in polypropylene production on an industrial scale. J. Chromatogr. A 2020, 1628, 461478.Hernández-Fernández, J.; Lopez-Martinez, J.; Barceló, D. Quantification and elimination of substituted synthetic phenols and volatile organic compounds in the wastewater treatment plant during the production of industrial scale polypropylene. Chemosphere 2021, 263, 128027. [Hernández-Fernandez, J.; Lopez-Martinez, J.; Puello-Polo, E. Recovery of (Z)-13-Docosenamide from Industrial Wastewater and Its Application in the Production of Virgin Polypropylene to Improve the Coefficient of Friction in Film Type Applications. Sustainability 2023, 15, 1247.Joaquin, H.-F.; Juan, L. Quantification of poisons for Ziegler Natta catalysts and effects on the production of polypropylene by gas chromatographic with simultaneous detection: Pulsed discharge helium ionization, mass spectrometry and flame ionization. J. Chromatogr. A 2020, 1614, 460736Hernández-Fernández, J.; Cano-Cuadro, H.; Puello-Polo, E. Emission of Bisphenol A and Four New Analogs from Industrial Wastewater Treatment Plants in the Production Processes of Polypropylene and Polyethylene Terephthalate in South America. Sustainability 2022, 14, 10919.Hernández-Fernández, J.; Cano, H.; Aldas, M. Impact of Traces of Hydrogen Sulfide on the Efficiency of Ziegler–Natta Catalyst on the Final Properties of Polypropylene. Polymers 2022, 14, 3910.Hernández-Fernández, J.; Guerra, Y.; Espinosa, E. Development and Application of a Principal Component Analysis Model to Quantify the Green Ethylene Content in Virgin Impact Copolymer Resins During Their Synthesis on an Industrial Scale. J. Polym. Environ. 2022, 30, 4800–4808Hernández-Fernández, J.; Guerra, Y.; Puello-Polo, E.; Marquez, E. Effects of Different Concentrations of Arsine on the Synthesis and Final Properties of Polypropylene. Polymers 2022, 14, 3123. [Hernández-Fernández, J.; Vivas-Reyes, R.; Toloza, C.A.T. Experimental Study of the Impact of Trace Amounts of Acetylene and Methylacetylene on the Synthesis, Mechanical and Thermal Properties of Polypropylene. Int. J. Mol. Sci. 2022, 23, 12148.Lavrenov, A.V.; Saifulina, L.F.; Buluchevskii, E.A.; Bogdanets, E.N. Propylene production technology: Today and tomorrow. Catal. Ind. 2015, 7, 175–187Tähkämö, L.; Ojanperä, A.; Kemppi, J.; Deviatkin, I. Life cycle assessment of renewable liquid hydrocarbons, propylene, and polypropylene derived from bio-based waste and residues: Evaluation of climate change impacts and abiotic resource depletion potential. J. Clean. Prod. 2022, 379, 134645.Hernández-Fernández, J.; Castro-Suarez, J.R.; Toloza, C.A.T. Iron Oxide Powder as Responsible for the Generation of Industrial Polypropylene Waste and as a Co-Catalyst for the Pyrolysis of Non-Additive Resins. Int. J. Mol. Sci. 2022, 23, 11708. [Petrovics, N.; Kirchkeszner, C.; Tábi, T.; Magyar, N.; Székely, I.K.; Szabó, B.S.; Nyiri, Z.; Eke, Z. Effect of temperature and plasticizer content of polypropylene and polylactic acid on migration kinetics into isooctane and 95 v/v% ethanol as alternative fatty food simulants. Food Packag. Shelf Life 2022, 33, 100916Hermabessiere, L.; Receveur, J.; Himber, C.; Mazurais, D.; Huvet, A.; Lagarde, F.; Lambert, C.; Paul-Pont, I.; Dehaut, A.; Jezequel, R.; et al. An Irgafos® 168 story: When the ubiquity of an additive prevents studying its leaching from plastics. Sci. Total Environ. 2020, 749, 141651.. Vera, P.; Canellas, E.; Su, Q.-Z.; Mercado, D.; Nerín, C. Migration of volatile substances from recycled high density polyethylene to milk products. Food Packag. Shelf Life 2023, 35, 101020.Kung, H.-C.; Hsieh, Y.-K.; Huang, B.-W.; Cheruiyot, N.K.; Chang-Chien, G.-P. An Overview: Organophosphate Flame Retardants in the Atmosphere. Aerosol Air Qual. Res. 2022, 22, 220148Onoja, S.; Nel, H.A.; Abdallah, M.A.-E.; Harrad, S. Microplastics in freshwater sediments: Analytical methods, temporal trends, and risk of associated organophosphate esters as exemplar plastics additives. Environ. Res. 2022, 203, 111830.Xiao, L.; Zheng, Z.; Irgum, K.; Andersson, P.L. Studies of Emission Processes of Polymer Additives into Water Using Quartz Crystal Microbalance—A Case Study on Organophosphate Esters. Environ. Sci. Technol. 2020, 54, 4876–4885.Li, A.; Zheng, G.; Chen, N.; Xu, W.; Li, Y.; Shen, F.; Wang, S.; Cao, G.; Li, J. Occurrence Characteristics and Ecological Risk Assessment of Organophosphorus Compounds in a Wastewater Treatment Plant and Upstream Enterprises. Water 2022, 14, 3942.Liu, R.; Mabury, S.A. Synthetic Phenolic Antioxidants: A Review of Environmental Occurrence, Fate, Human Exposure, and Toxicity. Environ. Sci. Technol. 2020, 54, 11706–11719.Dương, T.-B.; Dwivedi, R.; Bain, L.J. 2,4-di-tert-butylphenol exposure impairs osteogenic differentiation. Toxicol. Appl. Pharmacol. 2023, 461, 116386.Chen, Y.; Chen, Q.; Zhang, Q.; Zuo, C.; Shi, H. An Overview of Chemical Additives on (Micro)Plastic Fibers: Occurrence, Release, and Health Risks. Rev. Environ. Contam. Toxicol. 2022, 260, 22Simoneau, C.; Van Den Eede, L.; Valzacchi, S. Identification and quantification of the migration of chemicals from plastic baby bottles used as substitutes for polycarbonate. Food Addit. Contam. Part A 2012, 29, 469–480.Fouyer, K.; Lavastre, O.; Rondeau, D. Direct Monitoring of the Role Played by a Stabilizer in a Solid Sample of Polymer Using Direct Analysis in Real Time Mass Spectrometry: The Case of Irgafos 168 in Polyethylene. Anal. Chem. 2012, 84, 8642–8649.Sommers, C.H.; Sheen, S. Inactivation of avirulent Yersinia pestis on food and food contact surfaces by ultraviolet light and freezing. Food Microbiol. 2015, 50, 1–4FDA. Irradiation in the Production, Processing and Handling of Food. Final Rule, November 2012. Available online: https://www. researchgate.net/publication/284923753_Irradiation_in_the_production_processing_and_handling_of_food_Final_rule (accessed on 3 March 2022).Yang, Y.P.; Hu, C.; Zhong, H.; Wang, Z.Y.; Zeng, G.F. Degradation of Irgafos 168 and determination of its degra-dation products. Mod. Food Sci. Technol. 2016, 32, 304–309.James, B.D.; De Vos, A.; Aluwihare, L.I.; Youngs, S.; Ward, C.P.; Nelson, R.K.; Michel, A.P.M.; Hahn, M.E.; Reddy, C.M. Divergent Forms of Pyroplastic: Lessons Learned from the M/V X-Press Pearl Ship Fire. ACS Environ. Au 2022, 2, 467–479Zhao, F.; Wang, P.; Lucardi, R.; Su, Z.; Li, S. Natural Sources and Bioactivities of 2,4-Di-Tert-Butylphenol and Its Analogs. Toxins 2020, 12, 35. [Shi, J.; Xu, C.; Xiang, L.; Chen, J.; Cai, Z. Tris(2,4-di-tert-butylphenyl)phosphate: An Unexpected Abundant Toxic Pollutant Found in PM2.5. Environ. Sci. Technol. 2020, 54, 10570–10576.Luque-García, J.; de Castro, M.L. Ultrasound: A powerful tool for leaching. TrAC Trends Anal. Chem. 2003, 22, 41–47.Lama-Muñoz, A.; Contreras, M.D.M. Extraction Systems and Analytical Techniques for Food Phenolic Compounds: A Review. Foods 2022, 11, 3671Sachon, E.; Matheron, L.; Clodic, G.; Blasco, T.; Bolbach, G. MALDI TOF-TOF characterization of a light stabilizer polymer contaminant from polypropylene or polyethylene plastic test tubes. J. Mass Spectrom. 2010, 45, 43–50.Feng, G.; Wang, X.; Zhang, D.; Xiao, X.; Qian, K. Fabrication of bilayer antioxidant microcapsule and evaluation of its efficiency in stabilization of polypropylene. Mater. Res. Express 2019, 6, 125327Farajzadeh, M.A.; Goushjuii, L.; Ranji, A.; Feyz, E. Spectrophotometric determination of Irgafos 168 in polymers after different sample preparation procedures. Microchim. Acta 2007, 159, 263–268Fiorio, R.; D’Hooge, D.R.; Ragaert, K.; Cardon, L. A Statistical Analysis on the Effect of Antioxidants on the Thermal-Oxidative Stability of Commercial Mass- and Emulsion-Polymerized ABS. Polymers 2018, 11, 25.Li, B.; Wang, Z.-W.; Lin, Q.-B.; Hu, C.-Y.; Su, Q.-Z.; Wu, Y.-M. Determination of Polymer Additives-Antioxidants, Ultraviolet Stabilizers, Plasticizers and Photoinitiators in Plastic Food Package by Accelerated Solvent Extraction Coupled with HighPerformance Liquid Chromatography. J. Chromatogr. Sci. 2015, 53, 1026–1035.Rodil, R.; Quintana, J.B.; Basaglia, G.; Pietrogrande, M.C.; Cela, R. Determination of synthetic phenolic antioxidants and their metabolites in water samples by downscaled solid-phase extraction, silylation and gas chromatography–mass spectrometry. J. Chromatogr. A 2010, 1217, 6428–6435.Hernández-Fernández, J.; Ortega-Toro, R.; López-Martinez, J. A New Route of Valorization of Petrochemical Wastewater: Recovery of 1,3,5-Tris (4-tert-butyl-3-hydroxy-2,6-dimethyl benzyl)–1,3,5-triazine-2,4,6-(1H,3H,5H)-trione (Cyanox 1790) and Its Subsequent Application in a PP Matrix to Improve Its Thermal Stability. Molecules 2023, 28, 2003Badri, K.; Redwan, A. Molecular Characterization of Synthetic Polymers by Means of Liquid Chromatography. In Physical Chemistry of Macromolecules: Macro to Nanoscales; Apple Academic Press: Bratislava, Slovakia, 2014; pp. 237–348http://purl.org/coar/resource_type/c_2df8fbb1ORIGINALmolecules-28-03163.pdfmolecules-28-03163.pdfapplication/pdf6377749https://repositorio.utb.edu.co/bitstream/20.500.12585/12157/1/molecules-28-03163.pdffcf5d47dc5655b8b4db7f34717308a04MD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; charset=utf-8805https://repositorio.utb.edu.co/bitstream/20.500.12585/12157/2/license_rdf4460e5956bc1d1639be9ae6146a50347MD52LICENSElicense.txtlicense.txttext/plain; charset=utf-83182https://repositorio.utb.edu.co/bitstream/20.500.12585/12157/3/license.txte20ad307a1c5f3f25af9304a7a7c86b6MD53TEXTmolecules-28-03163.pdf.txtmolecules-28-03163.pdf.txtExtracted texttext/plain74855https://repositorio.utb.edu.co/bitstream/20.500.12585/12157/4/molecules-28-03163.pdf.txt7d509922fd3d1c3b39c0ade2a4bb472aMD54THUMBNAILmolecules-28-03163.pdf.jpgmolecules-28-03163.pdf.jpgGenerated Thumbnailimage/jpeg8136https://repositorio.utb.edu.co/bitstream/20.500.12585/12157/5/molecules-28-03163.pdf.jpgdcdcd50f17dee103d1133913fee22395MD5520.500.12585/12157oai:repositorio.utb.edu.co:20.500.12585/121572023-07-20 00:17:49.546Repositorio Institucional UTBrepositorioutb@utb.edu.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 |