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.
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机译：五种磺酰基芳族醇，即4-（（2-羟乙基）磺酰基）苯酚，4-（（2-（2-（2-（（4-羟苯基）磺酰基）乙氧基）乙烯基）磺酰基）苯酚，4-（乙基磺酰基）苯酚，通过LC-ESI-Qq-TOF-MS将4-（乙烯基磺酰基）苯酚和5-（（4-氨基苯基）磺酰基）-2-戊烯-1-醇鉴定为通过双偶氮活性染料活性黑5电解形成的产物（RB5）。由于电解是在装有Ni电极的碱性电解池中在碱性介质中进行的，因此也怀疑由于m / z 216形成了4-（2-甲氧基乙基磺酰基）苯胺（MEBA）之类的胺。 RB5及其氧化副产物的大量还原或阴极还原。为了检验该假设，使用了一种方法，通过化学还原染料RB5，制备了纯度为98％的MEBA。计算合成的磺酰基芳族化合物的logP，并通过色谱法测定其logkw值。关于疏水性/亲脂性与毒性之间的关系讨论了这些数据。
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