title: Formation of sulfonyl aromatic alcohols by electrolysis of a bisazo reactive dye.
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.
authors: Centro de Química, Instituto de Ciencias, Universidad Autónoma de Puebla, CU, San Claudio s/n, Edif 103H, 72570 Puebla, Pue., Mexico.
authors: María P
authors: MP
authors: Elizalde-González
authors: Uriel
authors: U
authors: Arroyo-Abad
authors: Esmeralda
authors: E
authors: García-Díaz
authors: Enric
authors: E
authors: Brillas
authors: Ignasi
authors: I
authors: Sirés
authors: Martín M
authors: MM
authors: Dávila-Jiménez
mesh_terms: D000438:Alcohols / Q000032:analysis / Q000737:chemistry*; D000588:Amines / Q000737:chemistry; D000814:Aniline Compounds / Q000138:chemical synthesis; D001673:Biodegradation, Environmental; D004396:Coloring Agents / Q000737:chemistry*; D004566:Electrodes; D004572:Electrolysis / Q000379:methods*; D009282:Naphthalenesulfonates / Q000032:analysis / Q000737:chemistry; D010636:Phenols / Q000737:chemistry; D014874:Water Pollutants, Chemical / Q000032:analysis / Q000737:chemistry
chemical_list: C583808:4-(2-methoxyethylsulfonyl)benzenamine; D000438:Alcohols; D000588:Amines; D000814:Aniline Compounds; D004396:Coloring Agents; D009282:Naphthalenesulfonates; D010636:Phenols; D014874:Water Pollutants, Chemical; C063421:Remazol black B