Physical-chemical study of anthracene selective oxidation by a Fe(III)-phenylporhyrin derivative

In this work, we studied the anthracene oxidation by hydroxyl radicals. Hydroxyl radical was generated by reaction of 5,10,15,20-tetrakis(4-carboxyphenyl)porphyrin Fe (III) (TPPFe) with hydrogen peroxide under visible radiation at a nitrogen atmosphere. The TPPFe was synthesized by Adler Method foll...

Full description

Autores:
Diaz-Uribe, Carlos
Tipo de recurso:
Fecha de publicación:
2019
Institución:
Universidad del Atlántico
Repositorio:
Repositorio Uniatlantico
Idioma:
eng
OAI Identifier:
oai:repositorio.uniatlantico.edu.co:20.500.12834/780
Acceso en línea:
https://hdl.handle.net/20.500.12834/780
Palabra clave:
sensitizer; porphyrin; hydroxyl radical; polycyclic aromatic hydrocarbons; anthracene
Rights
openAccess
License
http://creativecommons.org/licenses/by-nc/4.0/
id UNIATLANT2_abad78ef31eccbd25fedad1c8c90fdff
oai_identifier_str oai:repositorio.uniatlantico.edu.co:20.500.12834/780
network_acronym_str UNIATLANT2
network_name_str Repositorio Uniatlantico
repository_id_str
dc.title.spa.fl_str_mv Physical-chemical study of anthracene selective oxidation by a Fe(III)-phenylporhyrin derivative
title Physical-chemical study of anthracene selective oxidation by a Fe(III)-phenylporhyrin derivative
spellingShingle Physical-chemical study of anthracene selective oxidation by a Fe(III)-phenylporhyrin derivative
sensitizer; porphyrin; hydroxyl radical; polycyclic aromatic hydrocarbons; anthracene
title_short Physical-chemical study of anthracene selective oxidation by a Fe(III)-phenylporhyrin derivative
title_full Physical-chemical study of anthracene selective oxidation by a Fe(III)-phenylporhyrin derivative
title_fullStr Physical-chemical study of anthracene selective oxidation by a Fe(III)-phenylporhyrin derivative
title_full_unstemmed Physical-chemical study of anthracene selective oxidation by a Fe(III)-phenylporhyrin derivative
title_sort Physical-chemical study of anthracene selective oxidation by a Fe(III)-phenylporhyrin derivative
dc.creator.fl_str_mv Diaz-Uribe, Carlos
dc.contributor.author.none.fl_str_mv Diaz-Uribe, Carlos
dc.contributor.other.none.fl_str_mv William, Vallejo
Cesar, Quiñones
dc.subject.keywords.spa.fl_str_mv sensitizer; porphyrin; hydroxyl radical; polycyclic aromatic hydrocarbons; anthracene
topic sensitizer; porphyrin; hydroxyl radical; polycyclic aromatic hydrocarbons; anthracene
description In this work, we studied the anthracene oxidation by hydroxyl radicals. Hydroxyl radical was generated by reaction of 5,10,15,20-tetrakis(4-carboxyphenyl)porphyrin Fe (III) (TPPFe) with hydrogen peroxide under visible radiation at a nitrogen atmosphere. The TPPFe was synthesized by Adler Method followed by metal complexation with Fe (III) chloride hexahydrate. Hydroxyl radical was detected by fluorescence emission spectroscopy and we studied kinetic of anthracene selective oxidation by hydroxyl radicals through the differential method. The TPPFe was characterized by UV-Vis spectrophotometry, Dynamic Light Scattering (DLS) and Scanning Electron Microscopy (SEM) measurements. The results indicated that TPPFE was compound by micro-particles with a size distribution of around 2500 nm. Kinetic results showed that the apparent rate constant for the oxidation of anthracene increased exponentially on as temperature increases, furthermore, the activation energy for the Anthracene oxidation by hydroxyl radicals under visible irradiation was 51.3 kJ/mol. Finally, anthraquinone was the main byproduct generated after oxidation of anthracene by TPP-Fe under visible irradiation.
publishDate 2019
dc.date.issued.none.fl_str_mv 2019-10-30
dc.date.submitted.none.fl_str_mv 2020-01-03
dc.date.accessioned.none.fl_str_mv 2022-11-15T19:15:19Z
dc.date.available.none.fl_str_mv 2022-11-15T19:15:19Z
dc.type.coarversion.fl_str_mv http://purl.org/coar/version/c_970fb48d4fbd8a85
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/publishedVersion
dc.type.spa.spa.fl_str_mv Artículo
status_str publishedVersion
dc.identifier.uri.none.fl_str_mv https://hdl.handle.net/20.500.12834/780
dc.identifier.doi.none.fl_str_mv 10.3390/ijms21010353
dc.identifier.instname.spa.fl_str_mv Universidad del Atlántico
dc.identifier.reponame.spa.fl_str_mv Repositorio Universidad del Atlántico
url https://hdl.handle.net/20.500.12834/780
identifier_str_mv 10.3390/ijms21010353
Universidad del Atlántico
Repositorio Universidad del Atlántico
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/4.0/
dc.rights.cc.*.fl_str_mv Attribution-NonCommercial 4.0 International
dc.rights.accessRights.spa.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by-nc/4.0/
Attribution-NonCommercial 4.0 International
http://purl.org/coar/access_right/c_abf2
eu_rights_str_mv openAccess
dc.format.mimetype.spa.fl_str_mv application/pdf
dc.publisher.place.spa.fl_str_mv Barranquilla
dc.publisher.sede.spa.fl_str_mv Sede Norte
dc.source.spa.fl_str_mv International Journal of Molecular Sciences
institution Universidad del Atlántico
bitstream.url.fl_str_mv https://repositorio.uniatlantico.edu.co/bitstream/20.500.12834/780/1/ijms21010353.pdf
https://repositorio.uniatlantico.edu.co/bitstream/20.500.12834/780/2/license_rdf
https://repositorio.uniatlantico.edu.co/bitstream/20.500.12834/780/3/license.txt
bitstream.checksum.fl_str_mv 561e9b8a0dcbb87452f40c1a824a3769
24013099e9e6abb1575dc6ce0855efd5
67e239713705720ef0b79c50b2ececca
bitstream.checksumAlgorithm.fl_str_mv MD5
MD5
MD5
repository.name.fl_str_mv DSpace de la Universidad de Atlántico
repository.mail.fl_str_mv sysadmin@mail.uniatlantico.edu.co
_version_ 1814203412231749632
spelling Diaz-Uribe, Carlosf7c8b9b3-7d44-4293-a915-3130c37cadffWilliam, VallejoCesar, Quiñones2022-11-15T19:15:19Z2022-11-15T19:15:19Z2019-10-302020-01-03https://hdl.handle.net/20.500.12834/78010.3390/ijms21010353Universidad del AtlánticoRepositorio Universidad del AtlánticoIn this work, we studied the anthracene oxidation by hydroxyl radicals. Hydroxyl radical was generated by reaction of 5,10,15,20-tetrakis(4-carboxyphenyl)porphyrin Fe (III) (TPPFe) with hydrogen peroxide under visible radiation at a nitrogen atmosphere. The TPPFe was synthesized by Adler Method followed by metal complexation with Fe (III) chloride hexahydrate. Hydroxyl radical was detected by fluorescence emission spectroscopy and we studied kinetic of anthracene selective oxidation by hydroxyl radicals through the differential method. The TPPFe was characterized by UV-Vis spectrophotometry, Dynamic Light Scattering (DLS) and Scanning Electron Microscopy (SEM) measurements. The results indicated that TPPFE was compound by micro-particles with a size distribution of around 2500 nm. Kinetic results showed that the apparent rate constant for the oxidation of anthracene increased exponentially on as temperature increases, furthermore, the activation energy for the Anthracene oxidation by hydroxyl radicals under visible irradiation was 51.3 kJ/mol. Finally, anthraquinone was the main byproduct generated after oxidation of anthracene by TPP-Fe under visible irradiation.application/pdfenghttp://creativecommons.org/licenses/by-nc/4.0/Attribution-NonCommercial 4.0 Internationalinfo:eu-repo/semantics/openAccesshttp://purl.org/coar/access_right/c_abf2International Journal of Molecular SciencesPhysical-chemical study of anthracene selective oxidation by a Fe(III)-phenylporhyrin derivativePúblico generalsensitizer; porphyrin; hydroxyl radical; polycyclic aromatic hydrocarbons; anthraceneinfo:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionArtículohttp://purl.org/coar/version/c_970fb48d4fbd8a85http://purl.org/coar/resource_type/c_2df8fbb1BarranquillaSede NorteMa, J.; Liu, Y.; He, H. Degradation kinetics of anthracene by ozone on mineral oxides. Atmos. Environ. 2010, 44, 4446–4453.Ukiwe, L.N.; Egereonu, U.U.; Njoku, P.C.; Nwoko, C.I.A.; Allinor, J.I. Polycyclic aromatic hydrocarbons degradation techniques: A review. Int. J. Chem. 2013, 5, 43–55.Krumova, K.; Cosa, G. Chapter 1: Overview of reactive oxygen species. In Singlet Oxygen: Applications in Biosciences and Nanosciences, 1st ed.; RSC: London, UK, 2016; pp. 1–21.Kolarova, H.; Nevrelova, P.; Tomankova, K.; Kolar, P.; Bajgar, R.; Mosinger, J. Production of reactive oxygen species for photodynamic therapy by porphyrin sensitizers. Gen. Physiol. Biophys. 2008, 27, 101–105.Boyle, R.; Dolphin, D. Structure and biodistribution relationships of photodynamic sensitizers. Photochem. Photobiol. 1996, 64, 469–485.Ananthula, R.; Yamada, T.; Taylor, P.H. Kinetics of OH radical reaction with anthracene and anthracene-d10. J. Phys. Chem. A 2006, 110, 3559–3566.Silva, M.; Severino, D.; Manso, F.; Oliveira, M.; de Oliveira, M.B.; Baptista, M.; de Medeiros, M.G.; di Mascio, P. Synthesis and characterization of new anthracene derivatives used as singlet molecular oxygen chemical traps. Free Radic. Biol. Med. 2010, 49, S99–S100.Goulay, F.; Rebrion-Rowe, C.; le Garrec, J.L.; le Picard, S.D.; Canosa, A.; Rowe, B.R. The reaction of anthracene with OH radicals: An experimental studyof the kinetics between 58 and 470 K. J. Chem. Phys. 2005, 122, 104308.Dougherty, T.J.; Gomer, C.J.; Henderson, B.W.; Jori, G.; Kessel, D.; Korbelik, M.; Moan, J.; Peng, Q. Photodynamic therapy. J. Natl. Cancer Inst. 1998, 90, 889–905.Carella, A.; Borbone, F.; Centore, R. Research progress on photosensitizers for DSSC. Front. Chem. 2018, 6, 481.Chen, Y.; Li, A.; Huang, Z.; Wang, L.; Kan, F. Porphyrin-based nanostructures for photocatalytic applications. Nanomaterials (Basel) 2016, 6, 51.Zargari, S.; Rahimi, R.; Yousefi, A. An efficient visible light photocatalyst based on tin porphyrin intercalated between TiO2 graphene nanosheets for inactivation of E. coli and investigation of charge transfer mechanism. RSC Adv. 2016, 6, 24218–24228.Bonnett, R.; Roberts, S.; Phillips, D.; O’Brien, P. Chemical Aspects of Photodynamic Therapy, 1st ed.; CRC Press: London, UK, 2000; pp. 1–324.Ishibashi, K.; Fujishima, A.; Watanabe, T.; Hashimoto, K. Quantum yields of active oxidative spices formed on TiO2 photocatalyst. J. Photochem. Photobiol. A Chem. 2000, 134, 139–142. [Rodríguez, F.; Dolores, M.; Adrados, L.F.; Burillo, J.C.; Tijero, J.F. Selective oxidation of anthracene to anthraquinone in acetic acid with air in presence of nitric acid. Tetrahedron Lett. 1989, 30, 2417–2420.Safari, N.; Naghavi, S.; Khavasi, H.R. Homogeneous m-CPBA-oxidation of anthracene by electron-withdrawing metalloporphyrins in different reaction conditions. Appl. Catal. A Gen. 2005, 285, 59–64.Maranzana, A.; Ghigo, G.; Tonachini, G. Anthracene and phenanthrene tropospheric oxidation promoted by the nitrate radical in the gas-phase. Theoretical modelistic study. Atmos. Environ. 2017, 167, 181–189.Biermann, H.W.; Mac Leod, H.; Atkinson, R.; Winer, A.M.; Pitts, J.N. Kinetics of the gas-phase reactions of the hydroxyl radical with naphthalene, phenanthrene, and anthracene. Environ. Sci. Technol. 1985, 19, 244–248.Zhao, N.; Zhang, Q.; Wang, W. Atmospheric oxidation of phenanthrene initiated by OH radicals in the presence of O2 and NOx—A theoretical study. Sci. Total Environ. 2016, 563–564, 1008–1015.Zhang, Q.; Gao, R.; Xu, F.; Zhou, Q.; Jiang, G.; Wang, T.; Chen, J.; Hu, J.; Jiang, W.; Wang, W. Role of water molecule in the gas-phase formation process of nitrated polycyclic aromatic hydrocarbons in the atmosphere: A computational study. Environ. Sci. Technol. 2014, 48, 5051–5057.Fang, G.; Gao, J.; Dionysiou, D.D.; Liu, C.; Zhou, D. Activation of persulfate by quinones: Free radical reactions and implication for the degradation of PCBs. Environ. Sci. Technol. 2013, 47, 4605–4611.Wei, B.; Sun, J.; Mei, Q.; An, Z.; Wang, X.; He, M. Theoretical study on gas-phase reactions of nitrate radicals with methoxyphenols: Mechanism, kinetic and toxicity assessment. Environ. Pollut. 2018, 243, 1772–1780.Liu, W.; Lv, G.; Sun, X.; He, L.; Zhang, C.; Li, Z. Theoretical study on the reaction of anthracene with sulfate radical and hydroxyl radical in aqueous solution. Ecotoxicol. Environ. Saf. 2019, 183, 109551.Karam, F.F.; Hussein, F.H.; Baqir, S.J.; Halbus, A.F.; Dillert, R.; Bahnemann, D. Photocatalytic degradation of anthracene in closed system reactor. Int. J. Photoenergy 2014.Kozak, J.; Włodarczyk, M. Photo-oxidation of PAHs with calcium peroxide as a source of the hydroxyl radicals. E3S Web Conf. 2018, 30, 02009.Luo, Z.; Wang, J.; Song, Y.; Zheng, X.; Qu, L.L.; Wu, Z.; Wu, X. Remediation of phenanthrene contaminated soil by a solid-state photo-fenton reagent based on mesoporous magnetite/carboxylate-rich carbon composites and its phytotoxicity evaluation. ACS Sustain. Chem. Eng. 2018, 6, 13262–13275.Ke, Y.; Ning, X.A.; Liang, J.; Zou, H.; Sun, J.; Cai, H.; Lin, M.; Li, R.; Zhang, Y. Sludge treatment by integrated ultrasound-Fenton process: Characterization of sludge organic matter and its impact on PAHs removal. J. Hazard. Mater. 2018, 343, 191–199.Bocos, E.; Fernández-Costas, C.; Pazos, M.; Sanromán, M. Ángeles removal of PAHs and pesticides from polluted soils by enhanced electrokinetic-Fenton treatment. Chemosphere 2015, 125, 168–174.Zhao, X.; Qin, L.; Gatheru, M.; Cheng, P.; Yang, B.; Wang, J.; Ling, W. Removal of bound PAH residues in contaminated soils by Fenton oxidation. Catalysts 2019, 9, 619.Zhao, X.; Qin, L.; Gatheru, M.; Cheng, P.; Yang, B.; Wang, J.; Ling, W. Removal of bound PAH residues in contaminated soils by Fenton oxidation. Catalysts 2019, 9, 619.Karthikeyan, S.; Boopathy, R.; Gupta, V.K.; Sekaran, G. Preparation, characterizations and its application of heterogeneous Fenton catalyst for the treatment of synthetic phenol solution. J. Mol. Liq. 2013, 177, 402–408.Tryba, B.; Morawski, A.W.; Inagaki, M.; Toyoda, M. The kinetics of phenol decomposition under UV irradiation with and without H2O2 on TiO2, Fe-TiO2 and Fe-C-TiO2 photocatalysts. Appl. Catal. B Environ. 2006, 63, 215–221.Kusic, H.; Koprivanac, N.; Bozic, A.L.; Selanec, I. Photo-assisted Fenton type processes for the degradation of phenol: A kinetic study. J. Hazard. Mater. 2006, 136, 632–644.Zheng, W.; Shan, N.; Yu, L.; Wang, X. UV-visible, fluorescence and EPR properties of porphyrins and metalloporphyrins. Dyes Pigments 2008, 77, 153–157.Papkovsky, D.B.; Ponomare, G.V.; Trettnak, W.; O’Leary, P. Phosphorescent complexes of porphyrin ketones: Optical properties and application to oxygen sensing. Anal. Chem. 1995, 67, 4112–4117.Díaz, C.; Vallejo, W.; Miranda, J. Photo-Fenton oxidation of phenol with Fe(III)-tetra-4-carboxyphenylporphyrin/SiO2 assisted with visible light. J. Photochem. Photobiol. A Chem. 2014, 294, 75–80.Zhdanova, K.A.; Ezhov, A.V.; Bragina, N.A.; Mironov, A.F. Synthesis of new binary porphyrin-cyanine conjugates and their self-aggregation in organic-aqueous media. Mendeleev Commun. 2018, 28, 626–628.Andrade, S.M.; Teixeira, R.; Costa, S.M.B.; Sobral, A.J.F.N. Self-aggregation of free base porphyrins in aqueous solution and in DMPC vesicles. Biophys. Chem. 2008, 133, 1–10.Mark, G.; Tauber, A.; Laupert, R.; Schuchmann, H.; Schulz, D.; Mues, A.; Sonntag, C. OH-radical formation by ultrasound in aqueous solution—Part II: Terephthalate and Fricke dosimetry and the influence of various conditions on the sonolytic yield. Ultrason. Sonochem. 1998, 5, 41–52.Kohtani, S.; Tomohiro, M.; Tokumura, K.; Nakagaki, R. Photooxidation reactions of polycyclic aromatic hydrocarbons over pure and Ag-loaded BiVO4 photocatalysts. Appl. Catal. B Environ. 2005, 58, 265–272.Paddon, C.A.; Banks, C.E.; Davies, I.G.; Compton, R.G. Oxidation of anthracene on platinum macro- and micro-electrodes: Sonoelectrochemical, cryoelectrochemical and sonocryoelectrochemical studies. Ultrason. Sonochem. 2006, 13, 126–132.Cordeiro, D.S.; Corio, P. Electrochemical and photocatalytic reactions of polycyclic aromatic hydrocarbons investigated by raman spectroscopy. J. Braz. Chem. Soc. 2009, 2, 80–87.Adler, A.; Longo, F.; Finarelli, J.; Goldmacher, J.; Assour, J.; Korsakoff, L. A simplified synthesis for meso-tetraphenylporphine. J. Org. Chem. 1967, 32, 476.http://purl.org/coar/resource_type/c_6501ORIGINALijms21010353.pdfijms21010353.pdfapplication/pdf4204763https://repositorio.uniatlantico.edu.co/bitstream/20.500.12834/780/1/ijms21010353.pdf561e9b8a0dcbb87452f40c1a824a3769MD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; charset=utf-8914https://repositorio.uniatlantico.edu.co/bitstream/20.500.12834/780/2/license_rdf24013099e9e6abb1575dc6ce0855efd5MD52LICENSElicense.txtlicense.txttext/plain; charset=utf-81306https://repositorio.uniatlantico.edu.co/bitstream/20.500.12834/780/3/license.txt67e239713705720ef0b79c50b2ececcaMD5320.500.12834/780oai:repositorio.uniatlantico.edu.co:20.500.12834/7802022-11-15 14:15:20.292DSpace de la Universidad de Atlánticosysadmin@mail.uniatlantico.edu.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