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Molecules 2012, 17(12), 14377-14392; doi:10.3390/molecules171214377
Article

Formation of Sulfonyl Aromatic Alcohols by Electrolysis of a Bisazo Reactive Dye

1, 1, 2, 3, 3 and 2,*
1 Centro de Química, Instituto de Ciencias, Universidad Autónoma de Puebla, CU, San Claudio s/n, Edif 103H, 72570 Puebla, Pue., Mexico 2 Facultad de Ciencias Químicas, Universidad Autónoma de Puebla, CU, San Claudio s/n, Edif 105H, 72570 Puebla, Pue., Mexico 3 Laboratori d'Electroquímica dels Materials i del Medi Ambient, Departament de Química Física, Facultat de Química, Universitat de Barcelona, Martí i Franquès 1-11, 08028 Barcelona, Spain
* Author to whom correspondence should be addressed.
Received: 16 November 2012 / Revised: 29 November 2012 / Accepted: 29 November 2012 / Published: 5 December 2012
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Abstract

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.
Keywords: sulfonyl aromatic alcohols; 4-(2-methoxyethylsulfonyl)benzenamine; reactive black 5; electrolysis products; logP sulfonyl aromatic alcohols; 4-(2-methoxyethylsulfonyl)benzenamine; reactive black 5; electrolysis products; logP
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Elizalde-González, M.P.; Arroyo-Abad, U.; García-Díaz, E.; Brillas, E.; Sirés, I.; Dávila-Jiménez, M.M. Formation of Sulfonyl Aromatic Alcohols by Electrolysis of a Bisazo Reactive Dye. Molecules 2012, 17, 14377-14392.

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