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Potassium permanganate is an oxidizing agent, is used in the synthesis of organic compounds like ascorbic acid, chloramphenicol, saccharin, isonicotinic acid and pyrazinoic acid and in pharmaceutical intermediate. It is used to remove ferrous impurities from inorganic chemicals. It is also used in analytical chemistry as a reagent for redox titrations and to determine the kappa number of wood pulp. It is mostly used in water treatment and as a disinfectant. It also shows useful application as a chemiluminescence reagent.
The oxidizing power of permanganate can be varied according to the pH of the reaction medium, the use of co-reagents, phase-transfer catalysis, etc. For a comprehensive review of permanganate oxidations in organic chemistry, with particular emphasis on novel applications, see: Synthesis, 85, (1987).
For phase-transfer oxidation, catalyzed by Tetra-n-butylammonium hydrogen sulfate, A14047, of unfunctionalized benzylic methylenes, or benzylic alcohols to carbonyls, see: Synthesis, 915 (1987). Similar transformations have been carried out in the presence of triethylamine: Synthesis, 293 (1989).
For the use of (1-Hexadecyl)trimethylammonium bromide, A15235, as a surfactant in permanganate oxidations in micelles, see: Can. J. Chem., 67, 1381 (1989).
Classical permanganate cleavage of olefins is difficult to control, and normally proceeds to the highest possible oxidation level. Adsorption of the reagent on moist alumina has been found to attenuate its activity and allow good yields of aldehydes to be obtained. This would appear to provide a possible alternative to ozonolysis for this conversion: J. Org. Chem., 58, 2918 (1993). For use in the cis-hydroxylation of olefins, see Dicyclohexano-18-crown-6, A15344.
For phase-transfer assisted oxidation of primary amines to azo compounds, see: Bull. Soc. Chim. Belg., 102, 59 (1993).
In combination with CuSO 4, has been used as a reagent for the heterogeneous oxidative cyclization of the primary position of a primary-secondary diol to the lactone: J. Chem. Soc., Chem. Commun., 634 (1988); Org, Synth. Coll., 9, 462 (1998):
In combination with TMS chloride and benzyl triethylammonium chloride, generates a reagent for mild anti dichlorination of alkenes, conversion of epoxides to chlorohydrins, and selective oxidation of sulfides to sulfoxides: Tetrahedron Lett., 38, 2339 (1997).
Adcock, J. L.; Barnett, N. W.; Barrow, C. J.; Francis, P. S. Advances in the use of acidic potassium permanganate as a chemiluminescence reagent: A review. Anal. Chim. Acta 2014, 807, 9-28.
Wu, C.; Zhang, G.; Zhang, P.; Chang, C. C. Disintegration of excess activated sludge with potassium permanganate: feasibility, mechanisms and parameter optimization. Chem. Eng. J. 2014, 240, 420-425.
Gefahrenhinweise (EU): H272-H302
May intensify fire; oxidizer. Harmful if swallowed.
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