Photodegradation of bisphenol A and related compounds under natural-like conditions in the presence of riboflavin: Kinetics, mechanism and photoproducts

Autores
Barbieri, Yanina; Massad, Walter Alfredo; Díaz, Dante J.; Sanz, Jesús; Amat Guerri, Francisco; Garcia, Norman Andino
Año de publicación
2008
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The aerobic riboflavin (Rf)-sensitized photodegradation of the endocrine disruptor 4,40 -isopropylidenebisphenol (bisphenol A, BPA), and of the related compounds 4,40 -isopropylidenebis(2,6-dibromophenol) and 4,40 -isopropylidenebis(2,6-dimethylphenol) has been studied in water and water–methanol mixtures through visible-light continuous photolysis, polarographic detection of oxygen uptake, stationary and time-resolved fluorescence spectroscopy, time-resolved near-IR phosphorescence detection and laser flash photolysis techniques. Bisphenols (BPs) quench excited singlet and triplet states of Rf, with rate constants close to the diffusion limit. BPs and dissolved molecular oxygen, employed in similar concentrations, competitively quench triplet excited Rf. As a consequence, superoxide radical anion and singlet molecular oxygen (O2( 1 Dg)) are produced by electron- and energy-transfer processes, respectively, as demonstrated by auxiliary experiments employing selective quenchers of both oxidative species and the exclusive O2( 1 Dg) generator Rose Bengal. As a global result, the photodegradation of Rf is retarded, whereas BPs are degraded, mainly by an O2( 1 Dg)-mediated mechanism, which constitutes a relatively efficient process in the case of BPA. Oxidation, dimerization and fragmentation products have been identified in the photooxidation of BPA. Results indicate that BPs in natural waters can undergo spontaneous photodegradation under environmental conditions in the presence of adequate photosensitizers.
Fil: Barbieri, Yanina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Massad, Walter Alfredo. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina
Fil: Díaz, Dante J.. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Sanz, Jesús. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Amat Guerri, Francisco. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Garcia, Norman Andino. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Materia
Bisphenol
Photodegradation
Photosensitization
Riboflavin
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/242231
Acceder
id CONICETDig_e6d6303d751d91d1545f5a848a8195de
oai_identifier_str oai:ri.conicet.gov.ar:11336/242231
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Photodegradation of bisphenol A and related compounds under natural-like conditions in the presence of riboflavin: Kinetics, mechanism and photoproductsBarbieri, YaninaMassad, Walter AlfredoDíaz, Dante J.Sanz, JesúsAmat Guerri, FranciscoGarcia, Norman AndinoBisphenolPhotodegradationPhotosensitizationRiboflavinhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The aerobic riboflavin (Rf)-sensitized photodegradation of the endocrine disruptor 4,40 -isopropylidenebisphenol (bisphenol A, BPA), and of the related compounds 4,40 -isopropylidenebis(2,6-dibromophenol) and 4,40 -isopropylidenebis(2,6-dimethylphenol) has been studied in water and water–methanol mixtures through visible-light continuous photolysis, polarographic detection of oxygen uptake, stationary and time-resolved fluorescence spectroscopy, time-resolved near-IR phosphorescence detection and laser flash photolysis techniques. Bisphenols (BPs) quench excited singlet and triplet states of Rf, with rate constants close to the diffusion limit. BPs and dissolved molecular oxygen, employed in similar concentrations, competitively quench triplet excited Rf. As a consequence, superoxide radical anion and singlet molecular oxygen (O2( 1 Dg)) are produced by electron- and energy-transfer processes, respectively, as demonstrated by auxiliary experiments employing selective quenchers of both oxidative species and the exclusive O2( 1 Dg) generator Rose Bengal. As a global result, the photodegradation of Rf is retarded, whereas BPs are degraded, mainly by an O2( 1 Dg)-mediated mechanism, which constitutes a relatively efficient process in the case of BPA. Oxidation, dimerization and fragmentation products have been identified in the photooxidation of BPA. Results indicate that BPs in natural waters can undergo spontaneous photodegradation under environmental conditions in the presence of adequate photosensitizers.Fil: Barbieri, Yanina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaFil: Massad, Walter Alfredo. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; ArgentinaFil: Díaz, Dante J.. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaFil: Sanz, Jesús. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaFil: Amat Guerri, Francisco. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaFil: Garcia, Norman Andino. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaPergamon-Elsevier Science Ltd2008-09info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/242231Barbieri, Yanina; Massad, Walter Alfredo; Díaz, Dante J.; Sanz, Jesús; Amat Guerri, Francisco; et al.; Photodegradation of bisphenol A and related compounds under natural-like conditions in the presence of riboflavin: Kinetics, mechanism and photoproducts; Pergamon-Elsevier Science Ltd; Chemosphere; 73; 4; 9-2008; 564-5710045-6535CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0045653508007789info:eu-repo/semantics/altIdentifier/doi/10.1016/j.chemosphere.2008.06.013info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:59:16Zoai:ri.conicet.gov.ar:11336/242231instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 09:59:16.684CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Photodegradation of bisphenol A and related compounds under natural-like conditions in the presence of riboflavin: Kinetics, mechanism and photoproducts
title Photodegradation of bisphenol A and related compounds under natural-like conditions in the presence of riboflavin: Kinetics, mechanism and photoproducts
spellingShingle Photodegradation of bisphenol A and related compounds under natural-like conditions in the presence of riboflavin: Kinetics, mechanism and photoproducts
Barbieri, Yanina
Bisphenol
Photodegradation
Photosensitization
Riboflavin
title_short Photodegradation of bisphenol A and related compounds under natural-like conditions in the presence of riboflavin: Kinetics, mechanism and photoproducts
title_full Photodegradation of bisphenol A and related compounds under natural-like conditions in the presence of riboflavin: Kinetics, mechanism and photoproducts
title_fullStr Photodegradation of bisphenol A and related compounds under natural-like conditions in the presence of riboflavin: Kinetics, mechanism and photoproducts
title_full_unstemmed Photodegradation of bisphenol A and related compounds under natural-like conditions in the presence of riboflavin: Kinetics, mechanism and photoproducts
title_sort Photodegradation of bisphenol A and related compounds under natural-like conditions in the presence of riboflavin: Kinetics, mechanism and photoproducts
dc.creator.none.fl_str_mv Barbieri, Yanina
Massad, Walter Alfredo
Díaz, Dante J.
Sanz, Jesús
Amat Guerri, Francisco
Garcia, Norman Andino
author Barbieri, Yanina
author_facet Barbieri, Yanina
Massad, Walter Alfredo
Díaz, Dante J.
Sanz, Jesús
Amat Guerri, Francisco
Garcia, Norman Andino
author_role author
author2 Massad, Walter Alfredo
Díaz, Dante J.
Sanz, Jesús
Amat Guerri, Francisco
Garcia, Norman Andino
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Bisphenol
Photodegradation
Photosensitization
Riboflavin
topic Bisphenol
Photodegradation
Photosensitization
Riboflavin
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The aerobic riboflavin (Rf)-sensitized photodegradation of the endocrine disruptor 4,40 -isopropylidenebisphenol (bisphenol A, BPA), and of the related compounds 4,40 -isopropylidenebis(2,6-dibromophenol) and 4,40 -isopropylidenebis(2,6-dimethylphenol) has been studied in water and water–methanol mixtures through visible-light continuous photolysis, polarographic detection of oxygen uptake, stationary and time-resolved fluorescence spectroscopy, time-resolved near-IR phosphorescence detection and laser flash photolysis techniques. Bisphenols (BPs) quench excited singlet and triplet states of Rf, with rate constants close to the diffusion limit. BPs and dissolved molecular oxygen, employed in similar concentrations, competitively quench triplet excited Rf. As a consequence, superoxide radical anion and singlet molecular oxygen (O2( 1 Dg)) are produced by electron- and energy-transfer processes, respectively, as demonstrated by auxiliary experiments employing selective quenchers of both oxidative species and the exclusive O2( 1 Dg) generator Rose Bengal. As a global result, the photodegradation of Rf is retarded, whereas BPs are degraded, mainly by an O2( 1 Dg)-mediated mechanism, which constitutes a relatively efficient process in the case of BPA. Oxidation, dimerization and fragmentation products have been identified in the photooxidation of BPA. Results indicate that BPs in natural waters can undergo spontaneous photodegradation under environmental conditions in the presence of adequate photosensitizers.
Fil: Barbieri, Yanina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Massad, Walter Alfredo. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina
Fil: Díaz, Dante J.. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Sanz, Jesús. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Amat Guerri, Francisco. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Garcia, Norman Andino. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
description The aerobic riboflavin (Rf)-sensitized photodegradation of the endocrine disruptor 4,40 -isopropylidenebisphenol (bisphenol A, BPA), and of the related compounds 4,40 -isopropylidenebis(2,6-dibromophenol) and 4,40 -isopropylidenebis(2,6-dimethylphenol) has been studied in water and water–methanol mixtures through visible-light continuous photolysis, polarographic detection of oxygen uptake, stationary and time-resolved fluorescence spectroscopy, time-resolved near-IR phosphorescence detection and laser flash photolysis techniques. Bisphenols (BPs) quench excited singlet and triplet states of Rf, with rate constants close to the diffusion limit. BPs and dissolved molecular oxygen, employed in similar concentrations, competitively quench triplet excited Rf. As a consequence, superoxide radical anion and singlet molecular oxygen (O2( 1 Dg)) are produced by electron- and energy-transfer processes, respectively, as demonstrated by auxiliary experiments employing selective quenchers of both oxidative species and the exclusive O2( 1 Dg) generator Rose Bengal. As a global result, the photodegradation of Rf is retarded, whereas BPs are degraded, mainly by an O2( 1 Dg)-mediated mechanism, which constitutes a relatively efficient process in the case of BPA. Oxidation, dimerization and fragmentation products have been identified in the photooxidation of BPA. Results indicate that BPs in natural waters can undergo spontaneous photodegradation under environmental conditions in the presence of adequate photosensitizers.
publishDate 2008
dc.date.none.fl_str_mv 2008-09
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/242231
Barbieri, Yanina; Massad, Walter Alfredo; Díaz, Dante J.; Sanz, Jesús; Amat Guerri, Francisco; et al.; Photodegradation of bisphenol A and related compounds under natural-like conditions in the presence of riboflavin: Kinetics, mechanism and photoproducts; Pergamon-Elsevier Science Ltd; Chemosphere; 73; 4; 9-2008; 564-571
0045-6535
CONICET Digital
CONICET
url http://hdl.handle.net/11336/242231
identifier_str_mv Barbieri, Yanina; Massad, Walter Alfredo; Díaz, Dante J.; Sanz, Jesús; Amat Guerri, Francisco; et al.; Photodegradation of bisphenol A and related compounds under natural-like conditions in the presence of riboflavin: Kinetics, mechanism and photoproducts; Pergamon-Elsevier Science Ltd; Chemosphere; 73; 4; 9-2008; 564-571
0045-6535
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0045653508007789
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.chemosphere.2008.06.013
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.069144

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