Formation of sulfonyl aromatic alcohols by electrolysis of a bisazo reactive dye

Five sulfonyl aromatic alcohols, namely 4-((2-hydroxyethyl)sulfonyl)phenol, 4-((2-(2-((4-hydroxyphenyl)sulfonyl)ethoxy)vinyl)sulfonyl)phenol, 4-(ethylsulfonyl)phenol, 4-(vinylsulfonyl)phenol and 5-((4-aminophenyl)sulfonyl)-2-penten-1-ol were identified by LC-ESI-Qq-TOF-MS as products formed by elect...

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Authors: Elizalde González, María P., Arroyo Abad, Uriel, Garcia Díaz, Esmeralda, Brillas, Enric, Sirés Sadornil, Ignacio, Dávila-Jiménez, Martín M.
Format: article
Status:Published version
Publication Date:2012
Country:España
Institution:Universidad de Barcelona
Repository:Dipòsit Digital de la UB
OAI Identifier:oai:diposit.ub.edu:2445/152586
Online Access:https://hdl.handle.net/2445/152586
Access Level:Open access
Keyword:Alcohols
Compostos aromàtics
Sulfonació
Electròlisi
Aromatic compounds
Sulphonation
Electrolysis
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spelling Formation of sulfonyl aromatic alcohols by electrolysis of a bisazo reactive dyeElizalde González, María P.Arroyo Abad, UrielGarcia Díaz, EsmeraldaBrillas, EnricSirés Sadornil, IgnacioDávila-Jiménez, Martín M.AlcoholsCompostos aromàticsSulfonacióElectròlisiAlcoholsAromatic compoundsSulphonationElectrolysisFive sulfonyl aromatic alcohols, namely 4-((2-hydroxyethyl)sulfonyl)phenol, 4-((2-(2-((4-hydroxyphenyl)sulfonyl)ethoxy)vinyl)sulfonyl)phenol, 4-(ethylsulfonyl)phenol, 4-(vinylsulfonyl)phenol and 5-((4-aminophenyl)sulfonyl)-2-penten-1-ol were identified by LC-ESI-Qq-TOF-MS as products formed by electrolysis of the bisazo reactive dye Reactive Black 5 (RB5). Since electrolyses were performed in an undivided cell equipped with Ni electrodes in alkaline medium, amines like 4-(2-methoxyethylsulfonyl)benzene-amine (MEBA) with m/z 216 were also suspected to be formed due to the plausible chemical reaction in the bulk or the cathodic reduction of RB5 and its oxidation by-products. Aiming to check this hypothesis, a method was used for the preparation of MEBA with 98% purity, via chemical reduction also of the dye RB5. The logP of the synthesized sulfonyl aromatic compounds was calculated and their logkw values were determined chromatographically. These data were discussed in regard to the relationship between hydrophobicity/lipophilicity and toxicity.MDPI2012info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionapplication/pdfhttps://hdl.handle.net/2445/152586Articles publicats en revistes (Ciència dels Materials i Química Física)reponame:Dipòsit Digital de la UBinstname:Universidad de BarcelonaInglésReproducció del document publicat a: https://doi.org/10.3390/molecules171214377Molecules, 2012, vol. 17, num. 12, p. 14377-14392https://doi.org/10.3390/molecules171214377cc-by (c) Elizalde González, María P. et al., 2012http://creativecommons.org/licenses/by/3.0/esinfo:eu-repo/semantics/openAccessoai:diposit.ub.edu:2445/1525862026-05-27T06:46:51Z
dc.title.none.fl_str_mv Formation of sulfonyl aromatic alcohols by electrolysis of a bisazo reactive dye
title Formation of sulfonyl aromatic alcohols by electrolysis of a bisazo reactive dye
spellingShingle Formation of sulfonyl aromatic alcohols by electrolysis of a bisazo reactive dye
Elizalde González, María P.
Alcohols
Compostos aromàtics
Sulfonació
Electròlisi
Alcohols
Aromatic compounds
Sulphonation
Electrolysis
title_short Formation of sulfonyl aromatic alcohols by electrolysis of a bisazo reactive dye
title_full Formation of sulfonyl aromatic alcohols by electrolysis of a bisazo reactive dye
title_fullStr Formation of sulfonyl aromatic alcohols by electrolysis of a bisazo reactive dye
title_full_unstemmed Formation of sulfonyl aromatic alcohols by electrolysis of a bisazo reactive dye
title_sort Formation of sulfonyl aromatic alcohols by electrolysis of a bisazo reactive dye
dc.creator.none.fl_str_mv Elizalde González, María P.
Arroyo Abad, Uriel
Garcia Díaz, Esmeralda
Brillas, Enric
Sirés Sadornil, Ignacio
Dávila-Jiménez, Martín M.
author Elizalde González, María P.
author_facet Elizalde González, María P.
Arroyo Abad, Uriel
Garcia Díaz, Esmeralda
Brillas, Enric
Sirés Sadornil, Ignacio
Dávila-Jiménez, Martín M.
author_role author
author2 Arroyo Abad, Uriel
Garcia Díaz, Esmeralda
Brillas, Enric
Sirés Sadornil, Ignacio
Dávila-Jiménez, Martín M.
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Alcohols
Compostos aromàtics
Sulfonació
Electròlisi
Alcohols
Aromatic compounds
Sulphonation
Electrolysis
topic Alcohols
Compostos aromàtics
Sulfonació
Electròlisi
Alcohols
Aromatic compounds
Sulphonation
Electrolysis
description Five sulfonyl aromatic alcohols, namely 4-((2-hydroxyethyl)sulfonyl)phenol, 4-((2-(2-((4-hydroxyphenyl)sulfonyl)ethoxy)vinyl)sulfonyl)phenol, 4-(ethylsulfonyl)phenol, 4-(vinylsulfonyl)phenol and 5-((4-aminophenyl)sulfonyl)-2-penten-1-ol were identified by LC-ESI-Qq-TOF-MS as products formed by electrolysis of the bisazo reactive dye Reactive Black 5 (RB5). Since electrolyses were performed in an undivided cell equipped with Ni electrodes in alkaline medium, amines like 4-(2-methoxyethylsulfonyl)benzene-amine (MEBA) with m/z 216 were also suspected to be formed due to the plausible chemical reaction in the bulk or the cathodic reduction of RB5 and its oxidation by-products. Aiming to check this hypothesis, a method was used for the preparation of MEBA with 98% purity, via chemical reduction also of the dye RB5. The logP of the synthesized sulfonyl aromatic compounds was calculated and their logkw values were determined chromatographically. These data were discussed in regard to the relationship between hydrophobicity/lipophilicity and toxicity.
publishDate 2012
dc.date.none.fl_str_mv 2012
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/2445/152586
url https://hdl.handle.net/2445/152586
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Reproducció del document publicat a: https://doi.org/10.3390/molecules171214377
Molecules, 2012, vol. 17, num. 12, p. 14377-14392
https://doi.org/10.3390/molecules171214377
dc.rights.none.fl_str_mv cc-by (c) Elizalde González, María P. et al., 2012
http://creativecommons.org/licenses/by/3.0/es
info:eu-repo/semantics/openAccess
rights_invalid_str_mv cc-by (c) Elizalde González, María P. et al., 2012
http://creativecommons.org/licenses/by/3.0/es
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv MDPI
publisher.none.fl_str_mv MDPI
dc.source.none.fl_str_mv Articles publicats en revistes (Ciència dels Materials i Química Física)
reponame:Dipòsit Digital de la UB
instname:Universidad de Barcelona
instname_str Universidad de Barcelona
reponame_str Dipòsit Digital de la UB
collection Dipòsit Digital de la UB
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15.301629

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