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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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2012-12, Vol.17 (12), p.14377-14392
Main Authors: Elizalde-González, María P, Arroyo-Abad, Uriel, García-Díaz, Esmeralda, Brillas, Enric, Sirés, Ignasi, Dávila-Jiménez, Martín M
Format: Article
Language:English
Subjects:
4-(2-methoxyethylsulfonyl)benzenamine
Alcohol
Alcohols - analysis
Alcohols - chemistry
Amines - chemistry
Aniline Compounds - chemical synthesis
Biodegradation
Biodegradation, Environmental
By products
Coloring Agents - chemistry
Electrodes
Electrolysis - methods
electrolysis products
Identification
logP
Naphthalenesulfonates - analysis
Naphthalenesulfonates - chemistry
Oxidation
Phenols
Phenols - chemistry
Pollutants
reactive black 5
Reagents
sulfonyl aromatic alcohols
Toxicity
Water Pollutants, Chemical - analysis
Water Pollutants, Chemical - chemistry
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Summary: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.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules171214377