Oxone (Potassium peroxymonosulfate, 2KHSO₅·KHSO₄·K₂SO₄)

Mechanism + Description

Depends on catalysts and additives present

General comments

Oxone is often used as a co-oxidant or terminal oxidant with various metal and non-metal catalysts. This material can oxidize alcohols to aldehydes and ketones alone, but over oxidation is often an issue. Whilst this reagent has a high mol wt hence poor atom economy, it is cheap, and the by-products are innocuous.

Key references

Synthetic commun. 2006, 36, 1147-1156 Oxone/Sodium Chloride: A Simple and Efficient Catalytic system for the Oxidation of Alcohols to Symmetric Esters and Ketones

Chem. Rev., 2013, 113  3329–3371  Journey Describing Applications of Oxone in Synthetic Chemistry

Advanced Synthesis & Catalysis 2006, 348, 877-880 An effective, cheap, environmentally benign and catalyst-free oxidation of alcohols was carried out at room temperature using tetra-n-butylammonium Oxone^®(TBA-OX) as oxidant with moderate to high selectivity for most of the alcohols using water as the solvent.

Relevant scale up example

No scale up examples identified