The riboflavin-photosensitized degradation of the uv-absorbing azo dye-metabolites Benzidine and o-Tolidine. Kinetic and mechanistic aspects

Autores
Morales, María Gisela; Pajares, Adriana Mabel; Natera, Jose Eduardo; Escalada, Juan Pablo; Massad, Walter Alfredo; Garcia, Norman Andino
Año de publicación
2017
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The visible-light-promoted photodegradation of two carcinogenic primary azo-dye metabolites (BZ-C), represented by the colourless water-contaminants Benzidine (BZ) and o-Tolidine (OT), was studied in water-methanol solution. It was done in the presence of air and the natural pigment riboflavin (Rf) as a photosensitizer. These conditions reasonably mimic a natural environment scenery. Both BZ-C interact with the reactive oxygen species (ROS) singlet molecular oxygen (O2(1Δg)), superoxide radical anion (O2[rad]–), hydrogen peroxide (H2O2) and hydroxyl radical (OH[rad]), all photogenerated in situ through energy-transfer and electron-transfer processes. The interaction of BZ-C with O2(1Δg) is essentially physical in nature and occurs with a relatively high rate constant value. The effective BZ-C degradation is mainly driven by the remaining photogenerated ROS. A comparison of the BZ and OT photooxidative-rate with those of the archetypal surface-water-contaminants aniline and phenol indicates that BZ-C degradation occurs in a moderately slower fashion than the reference contaminants, within a common overall time-scale. The primary photoprocesses initiating the Rf-sensitized degradation seems to be quite similar for the four compounds, with the simultaneous operation of Type I and Type II photoprocesses. In conclusion: the natural Rf- photosensitized degradation of BZ-C appears as a plausible process, as evaluated under simulated environmental conditions.
Fil: Morales, María Gisela. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de la Patagonia "San Juan Bosco"; Argentina
Fil: Pajares, Adriana Mabel. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de la Patagonia "San Juan Bosco"; Argentina. Universidad Nacional de la Patagonia Austral. Unidad Académica Caleta Olivia. Departamento de Ciencias Exactas y Naturales; Argentina
Fil: Natera, Jose Eduardo. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Escalada, Juan Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de la Patagonia Austral. Unidad Académica Caleta Olivia. Departamento de Ciencias Exactas y Naturales; Argentina
Fil: Massad, Walter Alfredo. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. 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; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Materia
BENZIDINE
O-TOLIDINE
PHOTOOXIDATION
RIBOFLAVIN
ROS
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:11336/84982
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/84982
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling The riboflavin-photosensitized degradation of the uv-absorbing azo dye-metabolites Benzidine and o-Tolidine. Kinetic and mechanistic aspectsMorales, María GiselaPajares, Adriana MabelNatera, Jose EduardoEscalada, Juan PabloMassad, Walter AlfredoGarcia, Norman AndinoBENZIDINEO-TOLIDINEPHOTOOXIDATIONRIBOFLAVINROShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The visible-light-promoted photodegradation of two carcinogenic primary azo-dye metabolites (BZ-C), represented by the colourless water-contaminants Benzidine (BZ) and o-Tolidine (OT), was studied in water-methanol solution. It was done in the presence of air and the natural pigment riboflavin (Rf) as a photosensitizer. These conditions reasonably mimic a natural environment scenery. Both BZ-C interact with the reactive oxygen species (ROS) singlet molecular oxygen (O2(1Δg)), superoxide radical anion (O2[rad]–), hydrogen peroxide (H2O2) and hydroxyl radical (OH[rad]), all photogenerated in situ through energy-transfer and electron-transfer processes. The interaction of BZ-C with O2(1Δg) is essentially physical in nature and occurs with a relatively high rate constant value. The effective BZ-C degradation is mainly driven by the remaining photogenerated ROS. A comparison of the BZ and OT photooxidative-rate with those of the archetypal surface-water-contaminants aniline and phenol indicates that BZ-C degradation occurs in a moderately slower fashion than the reference contaminants, within a common overall time-scale. The primary photoprocesses initiating the Rf-sensitized degradation seems to be quite similar for the four compounds, with the simultaneous operation of Type I and Type II photoprocesses. In conclusion: the natural Rf- photosensitized degradation of BZ-C appears as a plausible process, as evaluated under simulated environmental conditions.Fil: Morales, María Gisela. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de la Patagonia "San Juan Bosco"; ArgentinaFil: Pajares, Adriana Mabel. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de la Patagonia "San Juan Bosco"; Argentina. Universidad Nacional de la Patagonia Austral. Unidad Académica Caleta Olivia. Departamento de Ciencias Exactas y Naturales; ArgentinaFil: Natera, Jose Eduardo. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaFil: Escalada, Juan Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de la Patagonia Austral. Unidad Académica Caleta Olivia. Departamento de Ciencias Exactas y Naturales; ArgentinaFil: Massad, Walter Alfredo. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. 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; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; ArgentinaElsevier Science Sa2017-07info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/84982Morales, María Gisela; Pajares, Adriana Mabel; Natera, Jose Eduardo; Escalada, Juan Pablo; Massad, Walter Alfredo; et al.; The riboflavin-photosensitized degradation of the uv-absorbing azo dye-metabolites Benzidine and o-Tolidine. Kinetic and mechanistic aspects; Elsevier Science Sa; Journal of Photochemistry and Photobiology A: Chemistry; 344; 7-2017; 49-551010-6030CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S101060301631259Xinfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.jphotochem.2017.04.035info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:46:06Zoai:ri.conicet.gov.ar:11336/84982instacron: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:34982025-09-03 09:46:06.43CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv The riboflavin-photosensitized degradation of the uv-absorbing azo dye-metabolites Benzidine and o-Tolidine. Kinetic and mechanistic aspects
title The riboflavin-photosensitized degradation of the uv-absorbing azo dye-metabolites Benzidine and o-Tolidine. Kinetic and mechanistic aspects
spellingShingle The riboflavin-photosensitized degradation of the uv-absorbing azo dye-metabolites Benzidine and o-Tolidine. Kinetic and mechanistic aspects
Morales, María Gisela
BENZIDINE
O-TOLIDINE
PHOTOOXIDATION
RIBOFLAVIN
ROS
title_short The riboflavin-photosensitized degradation of the uv-absorbing azo dye-metabolites Benzidine and o-Tolidine. Kinetic and mechanistic aspects
title_full The riboflavin-photosensitized degradation of the uv-absorbing azo dye-metabolites Benzidine and o-Tolidine. Kinetic and mechanistic aspects
title_fullStr The riboflavin-photosensitized degradation of the uv-absorbing azo dye-metabolites Benzidine and o-Tolidine. Kinetic and mechanistic aspects
title_full_unstemmed The riboflavin-photosensitized degradation of the uv-absorbing azo dye-metabolites Benzidine and o-Tolidine. Kinetic and mechanistic aspects
title_sort The riboflavin-photosensitized degradation of the uv-absorbing azo dye-metabolites Benzidine and o-Tolidine. Kinetic and mechanistic aspects
dc.creator.none.fl_str_mv Morales, María Gisela
Pajares, Adriana Mabel
Natera, Jose Eduardo
Escalada, Juan Pablo
Massad, Walter Alfredo
Garcia, Norman Andino
author Morales, María Gisela
author_facet Morales, María Gisela
Pajares, Adriana Mabel
Natera, Jose Eduardo
Escalada, Juan Pablo
Massad, Walter Alfredo
Garcia, Norman Andino
author_role author
author2 Pajares, Adriana Mabel
Natera, Jose Eduardo
Escalada, Juan Pablo
Massad, Walter Alfredo
Garcia, Norman Andino
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv BENZIDINE
O-TOLIDINE
PHOTOOXIDATION
RIBOFLAVIN
ROS
topic BENZIDINE
O-TOLIDINE
PHOTOOXIDATION
RIBOFLAVIN
ROS
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 visible-light-promoted photodegradation of two carcinogenic primary azo-dye metabolites (BZ-C), represented by the colourless water-contaminants Benzidine (BZ) and o-Tolidine (OT), was studied in water-methanol solution. It was done in the presence of air and the natural pigment riboflavin (Rf) as a photosensitizer. These conditions reasonably mimic a natural environment scenery. Both BZ-C interact with the reactive oxygen species (ROS) singlet molecular oxygen (O2(1Δg)), superoxide radical anion (O2[rad]–), hydrogen peroxide (H2O2) and hydroxyl radical (OH[rad]), all photogenerated in situ through energy-transfer and electron-transfer processes. The interaction of BZ-C with O2(1Δg) is essentially physical in nature and occurs with a relatively high rate constant value. The effective BZ-C degradation is mainly driven by the remaining photogenerated ROS. A comparison of the BZ and OT photooxidative-rate with those of the archetypal surface-water-contaminants aniline and phenol indicates that BZ-C degradation occurs in a moderately slower fashion than the reference contaminants, within a common overall time-scale. The primary photoprocesses initiating the Rf-sensitized degradation seems to be quite similar for the four compounds, with the simultaneous operation of Type I and Type II photoprocesses. In conclusion: the natural Rf- photosensitized degradation of BZ-C appears as a plausible process, as evaluated under simulated environmental conditions.
Fil: Morales, María Gisela. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de la Patagonia "San Juan Bosco"; Argentina
Fil: Pajares, Adriana Mabel. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de la Patagonia "San Juan Bosco"; Argentina. Universidad Nacional de la Patagonia Austral. Unidad Académica Caleta Olivia. Departamento de Ciencias Exactas y Naturales; Argentina
Fil: Natera, Jose Eduardo. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
Fil: Escalada, Juan Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de la Patagonia Austral. Unidad Académica Caleta Olivia. Departamento de Ciencias Exactas y Naturales; Argentina
Fil: Massad, Walter Alfredo. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. 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; Argentina. Universidad Nacional de Río Cuarto. Facultad de Ciencias Exactas Fisicoquímicas y Naturales. Departamento de Química; Argentina
description The visible-light-promoted photodegradation of two carcinogenic primary azo-dye metabolites (BZ-C), represented by the colourless water-contaminants Benzidine (BZ) and o-Tolidine (OT), was studied in water-methanol solution. It was done in the presence of air and the natural pigment riboflavin (Rf) as a photosensitizer. These conditions reasonably mimic a natural environment scenery. Both BZ-C interact with the reactive oxygen species (ROS) singlet molecular oxygen (O2(1Δg)), superoxide radical anion (O2[rad]–), hydrogen peroxide (H2O2) and hydroxyl radical (OH[rad]), all photogenerated in situ through energy-transfer and electron-transfer processes. The interaction of BZ-C with O2(1Δg) is essentially physical in nature and occurs with a relatively high rate constant value. The effective BZ-C degradation is mainly driven by the remaining photogenerated ROS. A comparison of the BZ and OT photooxidative-rate with those of the archetypal surface-water-contaminants aniline and phenol indicates that BZ-C degradation occurs in a moderately slower fashion than the reference contaminants, within a common overall time-scale. The primary photoprocesses initiating the Rf-sensitized degradation seems to be quite similar for the four compounds, with the simultaneous operation of Type I and Type II photoprocesses. In conclusion: the natural Rf- photosensitized degradation of BZ-C appears as a plausible process, as evaluated under simulated environmental conditions.
publishDate 2017
dc.date.none.fl_str_mv 2017-07
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/11336/84982
Morales, María Gisela; Pajares, Adriana Mabel; Natera, Jose Eduardo; Escalada, Juan Pablo; Massad, Walter Alfredo; et al.; The riboflavin-photosensitized degradation of the uv-absorbing azo dye-metabolites Benzidine and o-Tolidine. Kinetic and mechanistic aspects; Elsevier Science Sa; Journal of Photochemistry and Photobiology A: Chemistry; 344; 7-2017; 49-55
1010-6030
CONICET Digital
CONICET
url http://hdl.handle.net/11336/84982
identifier_str_mv Morales, María Gisela; Pajares, Adriana Mabel; Natera, Jose Eduardo; Escalada, Juan Pablo; Massad, Walter Alfredo; et al.; The riboflavin-photosensitized degradation of the uv-absorbing azo dye-metabolites Benzidine and o-Tolidine. Kinetic and mechanistic aspects; Elsevier Science Sa; Journal of Photochemistry and Photobiology A: Chemistry; 344; 7-2017; 49-55
1010-6030
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/S101060301631259X
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.jphotochem.2017.04.035
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
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier Science Sa
publisher.none.fl_str_mv Elsevier Science Sa
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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