A green approach to Fenton chemistry: mono-hydroxylation of salicylic acid in aqueous medium by the electrogeneration of Fenton's reagent
First, the electrochemical characteristics of Fenton's reagent (Fe(iii), Fe(ii) and hydrogen peroxide), including its catalytic (EC′) behaviour were investigated. Second, the electrogeneration of hydrogen peroxide by a two-electron reduction of dissolved oxygen was conducted at a carbon electro...
| Main Authors: | , , , , , |
|---|---|
| Format: | Journal article |
| Language: | English |
| Published: |
2012
|
| _version_ | 1797056907143282688 |
|---|---|
| author | Panchompoo, J Aldous, L Kabeshov, M Pilgrim, B Donohoe, T Compton, R |
| author_facet | Panchompoo, J Aldous, L Kabeshov, M Pilgrim, B Donohoe, T Compton, R |
| author_sort | Panchompoo, J |
| collection | OXFORD |
| description | First, the electrochemical characteristics of Fenton's reagent (Fe(iii), Fe(ii) and hydrogen peroxide), including its catalytic (EC′) behaviour were investigated. Second, the electrogeneration of hydrogen peroxide by a two-electron reduction of dissolved oxygen was conducted at a carbon electrode in a divided electrolysis cell and the concentration of hydrogen peroxide obtained was determined by the titration. The two approaches were then combined to give a one-pot, relatively green approach to aromatic hydroxylation reactions, with the electro-Fenton method allowing the iron to be used catalytically and the oxygen/water employed as the hydroxylation reagent by the in situ production of hydrogen peroxide. In particular, the preparative-scale hydroxylation of salicylic acid has been studied in an oxygen-saturated 0.1 M Na 2SO 4 pH 3.0 solution containing 5 mM Fe(ii) and 5 mM salicylic acid at the controlled potential of -1.0 V vs. SCE. The study showed that after the attack of the hydroxyl radical produced in situ by the electro-Fenton process on salicylic acid, 2,3- and 2,5-dihydroxybenzoic acids were detected as primary monohydroxylated products with the highest yield of ca. 21.6 ± 2.5%. © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2012. |
| first_indexed | 2024-03-06T19:29:06Z |
| format | Journal article |
| id | oxford-uuid:1cd31238-a7e9-4376-b463-73c895855e64 |
| institution | University of Oxford |
| language | English |
| last_indexed | 2024-03-06T19:29:06Z |
| publishDate | 2012 |
| record_format | dspace |
| spelling | oxford-uuid:1cd31238-a7e9-4376-b463-73c895855e642022-03-26T11:07:44ZA green approach to Fenton chemistry: mono-hydroxylation of salicylic acid in aqueous medium by the electrogeneration of Fenton's reagentJournal articlehttp://purl.org/coar/resource_type/c_dcae04bcuuid:1cd31238-a7e9-4376-b463-73c895855e64EnglishSymplectic Elements at Oxford2012Panchompoo, JAldous, LKabeshov, MPilgrim, BDonohoe, TCompton, RFirst, the electrochemical characteristics of Fenton's reagent (Fe(iii), Fe(ii) and hydrogen peroxide), including its catalytic (EC′) behaviour were investigated. Second, the electrogeneration of hydrogen peroxide by a two-electron reduction of dissolved oxygen was conducted at a carbon electrode in a divided electrolysis cell and the concentration of hydrogen peroxide obtained was determined by the titration. The two approaches were then combined to give a one-pot, relatively green approach to aromatic hydroxylation reactions, with the electro-Fenton method allowing the iron to be used catalytically and the oxygen/water employed as the hydroxylation reagent by the in situ production of hydrogen peroxide. In particular, the preparative-scale hydroxylation of salicylic acid has been studied in an oxygen-saturated 0.1 M Na 2SO 4 pH 3.0 solution containing 5 mM Fe(ii) and 5 mM salicylic acid at the controlled potential of -1.0 V vs. SCE. The study showed that after the attack of the hydroxyl radical produced in situ by the electro-Fenton process on salicylic acid, 2,3- and 2,5-dihydroxybenzoic acids were detected as primary monohydroxylated products with the highest yield of ca. 21.6 ± 2.5%. © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2012. |
| spellingShingle | Panchompoo, J Aldous, L Kabeshov, M Pilgrim, B Donohoe, T Compton, R A green approach to Fenton chemistry: mono-hydroxylation of salicylic acid in aqueous medium by the electrogeneration of Fenton's reagent |
| title | A green approach to Fenton chemistry: mono-hydroxylation of salicylic acid in aqueous medium by the electrogeneration of Fenton's reagent |
| title_full | A green approach to Fenton chemistry: mono-hydroxylation of salicylic acid in aqueous medium by the electrogeneration of Fenton's reagent |
| title_fullStr | A green approach to Fenton chemistry: mono-hydroxylation of salicylic acid in aqueous medium by the electrogeneration of Fenton's reagent |
| title_full_unstemmed | A green approach to Fenton chemistry: mono-hydroxylation of salicylic acid in aqueous medium by the electrogeneration of Fenton's reagent |
| title_short | A green approach to Fenton chemistry: mono-hydroxylation of salicylic acid in aqueous medium by the electrogeneration of Fenton's reagent |
| title_sort | green approach to fenton chemistry mono hydroxylation of salicylic acid in aqueous medium by the electrogeneration of fenton s reagent |
| work_keys_str_mv | AT panchompooj agreenapproachtofentonchemistrymonohydroxylationofsalicylicacidinaqueousmediumbytheelectrogenerationoffentonsreagent AT aldousl agreenapproachtofentonchemistrymonohydroxylationofsalicylicacidinaqueousmediumbytheelectrogenerationoffentonsreagent AT kabeshovm agreenapproachtofentonchemistrymonohydroxylationofsalicylicacidinaqueousmediumbytheelectrogenerationoffentonsreagent AT pilgrimb agreenapproachtofentonchemistrymonohydroxylationofsalicylicacidinaqueousmediumbytheelectrogenerationoffentonsreagent AT donohoet agreenapproachtofentonchemistrymonohydroxylationofsalicylicacidinaqueousmediumbytheelectrogenerationoffentonsreagent AT comptonr agreenapproachtofentonchemistrymonohydroxylationofsalicylicacidinaqueousmediumbytheelectrogenerationoffentonsreagent AT panchompooj greenapproachtofentonchemistrymonohydroxylationofsalicylicacidinaqueousmediumbytheelectrogenerationoffentonsreagent AT aldousl greenapproachtofentonchemistrymonohydroxylationofsalicylicacidinaqueousmediumbytheelectrogenerationoffentonsreagent AT kabeshovm greenapproachtofentonchemistrymonohydroxylationofsalicylicacidinaqueousmediumbytheelectrogenerationoffentonsreagent AT pilgrimb greenapproachtofentonchemistrymonohydroxylationofsalicylicacidinaqueousmediumbytheelectrogenerationoffentonsreagent AT donohoet greenapproachtofentonchemistrymonohydroxylationofsalicylicacidinaqueousmediumbytheelectrogenerationoffentonsreagent AT comptonr greenapproachtofentonchemistrymonohydroxylationofsalicylicacidinaqueousmediumbytheelectrogenerationoffentonsreagent |