Solid-solid EC’ TEMPO-electrocatalytic conversion of diphenylcarbinol to benzophenone

Dawid Kaluza, Martin Jönsson-Niedziólka, Sunyhik D. Ahn, Rhodri E. Owen, Matthew D. Jones, Frank Marken

Research output: Contribution to journalArticle

Abstract

Voltammetry and chronoamperometry-based reactivity screening of water-insoluble microparticles is demonstrated for a mediated reaction. The solid-solid 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO)-mediated electrolytic conversion of diphenylcarbinol to benzophenone is investigated by employing TEMPO and its derivatives (4-carboxy-TEMPO, 4-methoxy-TEMPO, 4-amino-TEMPO, 4-acetamido-TEMPO) in alkaline carbonate buffer at pH 11. Chronoamperometry experiments reveal (at least) two reaction stages with (i) a high onset current (ca. 30 s) with nucleation and growth of product and (ii) a first-order transport-controlled reaction (ca. 5 min) leading to bulk conversion. It is shown that the type of TEMPO derivative and the pH (but not the TEMPO concentration) affect the reaction rate. The 4-acetamido-TEMPO derivative is the most effective mediator.

[Figure not available: see fulltext.]

LanguageEnglish
Pages1277-1283
Number of pages7
JournalJournal of Solid State Electrochemistry
Volume19
Issue number5
Early online date20 Jan 2015
DOIs
StatusPublished - May 2015

Fingerprint

Chronoamperometry
Derivatives
Carbonates
microparticles
Voltammetry
Reaction rates
high current
carbonates
Buffers
Screening
reaction kinetics
Nucleation
screening
reactivity
buffers
nucleation
Water
products
water
benzophenone

Keywords

  • Chronoamperometry
  • Electrocatalysis
  • Nucleation
  • Organic electrosynthesis
  • Solid-state electrolytic conversion

Cite this

Solid-solid EC’ TEMPO-electrocatalytic conversion of diphenylcarbinol to benzophenone. / Kaluza, Dawid; Jönsson-Niedziólka, Martin; Ahn, Sunyhik D.; Owen, Rhodri E.; Jones, Matthew D.; Marken, Frank.

In: Journal of Solid State Electrochemistry, Vol. 19, No. 5, 05.2015, p. 1277-1283.

Research output: Contribution to journalArticle

Kaluza, Dawid ; Jönsson-Niedziólka, Martin ; Ahn, Sunyhik D. ; Owen, Rhodri E. ; Jones, Matthew D. ; Marken, Frank. / Solid-solid EC’ TEMPO-electrocatalytic conversion of diphenylcarbinol to benzophenone. In: Journal of Solid State Electrochemistry. 2015 ; Vol. 19, No. 5. pp. 1277-1283.
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