Abstract
Owing to its electro-inactive character, anisole (phenylmethyl ether, PhOCH3) and its related derivatives have been used as electrolytes in electrochemistry. Herein, we report a simple one-step electro-organic conversion of PhOCH3 to hydroquinone (HQ) on a pristine-MWCNT–Nafion modified electrode glassy carbon electrode surface, GCE/Nf–MWCNT@HQ, in pH 2 KCl–HCl solution within 15 min of working time. The chemically modified electrode showed a highly redox-active and well-defined signal at an apparent standard electrode potential, Eo′ = 0.45 V vs. Ag/AgCl (A2/C2) with a surface excess value, ΓHQ = 2.1 × 10−9 mol cm−2. The formation of surface-confined HQ is confirmed by collective physicochemical and spectroscopic characterizations using TEM, UV-Vis, Raman, FTIR, NMR and GC-MS techniques and with several control experiments. Consent about the mechanism, the 2.1% of intrinsic iron present in the pristine-MWCNT is involved for specific complexation with oxygen donor organic molecule (PhOCH3) and hydroxylation in presence of H2O2 (nucleophilic attack) for HQ-product formation. The GCE/Nf–MWCNT@HQ showed an excellent heterogeneous-electrocatalytic reduction of Cr(vi) species in acidic solution with a linear calibration plot in a range, 5–500 ppm at an applied potential, 0.4 V vs. Ag/AgCl with a detection limit, 230 ppb (S/N = 3; amperometric i–t). As a proof of concept, selective detection of toxic Cr(vi) content in the tannery-waste water has been demonstrated with a recovery value ∼100%.
Highlights
Owing to its electro-inactive character, anisole and its related derivatives have been used as electrolytes in electrochemistry
First time in this work, we report, an in situ electrochemical reaction assisted demethoxylation and hydroxylation of an aromatic ether, anisole (PhOCH3) to hydroquinone (HQ) on intrinsic iron impurity containing multiwalled carbon nanotube/Na on (Nf–MWCNT) chemically modi ed electrode surface in mild acidic condition
An Nf–MWCNT modi ed glassy carbon electrode, designated as GCE/ Nf–MWCNT, has been used as a speci c electrode system for electrochemical molecular conversion of PhOCH3 to highly-redox active surface-con ned HQ, i.e., HQ immobilized on Nf– MWCNT, i.e., GCE/Nf–MWCNT@HQ, in presence of a dilute H2O2 solution
Summary
Zeolite (HBeta, HY),[13] MoO3/ZrO2,14 zeolite ZSM-5,15 zeolite HZ-25,16 P–Fe/SiO2,17 Hg(II),[18] etc. First time in this work, we report, an in situ electrochemical reaction assisted demethoxylation and hydroxylation of an aromatic ether, anisole (PhOCH3) to hydroquinone (HQ) on intrinsic iron impurity containing multiwalled carbon nanotube/Na on (Nf–MWCNT) chemically modi ed electrode surface in mild acidic condition. As a homogeneous catalyst, hexavalent chromium species has been reported for the alcohol derivatives oxidation reaction to respective carbonyl compounds.[55,56] In this work, the redoxactive polyphenol, HQ modi ed electrode has been used as a heterogeneous-electrocatalyst for the Cr(VI) reduction reaction in an acidic solution. To the best of our knowledge, this is the rst electrochemical study for the molecular transformation of anisole to HQ
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