Template:Main other <templatestyles src="Infobox drug/styles.css"/> {{#invoke:Infobox|infobox}}Template:Template other{{#invoke:TemplatePar |check |template=Template:Infobox_drug |all= |opt= pronounce= pronounce_ref= pronounce_comment= ATC_prefix= ATC_suffix= ATC_supplemental= ATCvet= biosimilars= CAS_number_Ref= CAS_number= CAS_supplemental= ChEBI= ChEBI_Ref= ChEMBL_Ref= ChEMBL= ChemSpiderID= ChemSpiderID_Ref= chirality= class= container_only= DailyMedID= data_page= DrugBank_Ref= DrugBank= Drugs.com= duration_of_action= INN= INN_EMA= IUPAC_name= IUPHAR_ligand= KEGG_Ref= KEGG= MedlinePlus= NIAID_ChemDB= PDB_ligand= PubChemSubstance= PubChem= StdInChIKey_Ref= StdInChIKey= StdInChI_Ref= StdInChI_comment= StdInChI= UNII_Ref= UNII= DTXSID= Verifiedfields= Watchedfields= addiction_liability= alt2= altL= altR= alt= bioavailability= boiling_high= boiling_notes= boiling_point= captionLR= caption= caption2= charge= chemical_formula= chemical_formula_ref= chemical_formula_comment= class1= class2= class3= class4= class5= class6= component1= component2= component3= component4= component5= component6= density= density_notes= dependency_liability= drug_name= elimination_half-life= engvar= excretion= image2= imageL= imageR= image= image_class= image_class2= image_classL= image_classR= Jmol= legal_AU= legal_BR= legal_CA= legal_DE= legal_EU= legal_NZ= legal_UK= legal_UN= legal_US= legal_AU_comment= legal_BR_comment= legal_CA_comment= legal_DE_comment= legal_UK_comment= legal_NZ_comment= legal_US_comment= legal_UN_comment= legal_EU_comment= legal_status= licence_CA= licence_EU= licence_US= license_CA= license_EU= license_US= mab_type= melting_high= melting_notes= melting_point= metabolism= metabolites= molecular_weight= molecular_weight_round= molecular_weight_unit= molecular_weight_ref= molecular_weight_comment= onset= pregnancy_AU= pregnancy_AU_comment= pregnancy_category= protein_bound= routes_of_administration= SMILES= smiles= solubility= sol_units= source= specific_rotation= synonyms= target= tradename= type= vaccine_type= verifiedrevid= width2= widthL= widthR= width= AAN= BAN= JAN= USAN= source_tissues= target_tissues= receptors= agonists= antagonists= precursor= biosynthesis= gt_target_gene= gt_vector= gt_nucleic_acid_type= gt_editing_method= gt_delivery_method= sec_combustion= Ac=Ag=Al=Am=Ar=As=At=Au=B=Ba=Be=Bh=Bi=Bk=Br=C=Ca=Cd=Ce=Cf=Cl=Cm=Cn=Co=Cr=Cs=Cu= D=Db=Ds=Dy=Er=Es=Eu=F=Fe=Fl=Fm=Fr=Ga=Gd=Ge=H=He=Hf=Hg=Ho=Hs=I=In=Ir=K=Kr=La=Li=Lr=Lu=Lv= Mc=Md=Mg=Mn=Mo=Mt=N=Na=Nb=Nd=Ne=Nh=Ni=No=Np=O=Og=Os=P=Pa=Pb=Pd=Pm=Po=Pr=Pt=Pu=Ra=Rb=Re=Rf=Rg=Rh=Rn=Ru=S=Sb=Sc=Se=Sg=Si=Sm=Sn=Sr=Ta=Tb=Tc=Te=Th=Ti=Tl=Tm=Ts=U=V=W=Xe=Y=Yb=Zn=Zr= index_label= index2_label= index_comment= index2_comment= CAS_number2= CAS_supplemental2= ATC_prefix2= ATC_suffix2= ATC_supplemental2= PubChem2= PubChemSubstance2= IUPHAR_ligand2= DrugBank2= ChemSpiderID2= UNII2= KEGG2= ChEBI2= ChEMBL2= PDB_ligand2= NIAID_ChemDB2= SMILES2= smiles2= StdInChI2= StdInChIKey2= CAS_number2_Ref= ChEBI2_Ref= ChEMBL2_Ref= ChemSpiderID2_Ref= DrugBank2_Ref= KEGG2_Ref= StdInChI2_Ref= StdInChIKey2_Ref= UNII2_Ref= DTXSID2= QID= QID2=PLLR= pregnancy_US= pregnancy_US_comment= |cat=Pages using infobox drug with unknown parameters |format=0|errNS=0

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| vaccine_type= | mab_type= | _number_of_combo_chemicals={{#invoke:ParameterCount |main |component1 |component2 |component3 |component4|component5|component6 }} | _vaccine_data= | _mab_data= | _mab_vaccine_data= | _mab_other_data= | _combo_data= | _physiological_data= | _clinical_data=Potassium_permanganate

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| _datapage = Potassium permanganate (data page) | _vaccine_target={{#ifeq: | vaccine | | _type_not_vaccine }} | _legal_all= | _ATC_prefix_supplemental= | _has_EMA_link = | CAS_number= | PubChem= | ChemSpiderID= | ChEBI= | ChEMBL= | DrugBank= | KEGG= | _hasInChI_or_Key={{#if: |yes}} | UNII= | _hasJmol02 = |_hasMultipleCASnumbers = |_hasMultiplePubChemCIDs = |_hasMultipleChEBIs =

| _countSecondIDs={{#invoke:ParameterCount |main |CAS_number2 |ATC_prefix2 |PubChem2 |PubChemStructure2 |IUPHAR_ligand2 |DrugBank2 |ChemSpiderID2 |UNII2 |KEGG2 |ChEBI2 |ChEMBL2 |PDB_ligand2 |NIAID_ChemDB2 |SMILES2 |smiles2 |StdInChI2 |StdInChIKey2 |DTXCID2}} | _countIndexlabels={{#invoke:ParameterCount |main |index_label |index2_label}} | _trackListSortletter= |QID = |QID2 = |Verifiedfields= |Watchedfields= |verifiedrevid=}} Template:Chembox Potassium permanganate is an inorganic compound with the chemical formula KMnO4. It is a purplish-black crystalline salt, which dissolves in water as K+ and [[permanganate|Template:Chem]] ions to give an intensely pink to purple solution.

Potassium permanganate is widely used in the chemical industry and laboratories as a strong oxidizing agent, and also as a medication for dermatitis, for cleaning wounds, and general disinfection. It is commonly used as a biocide for water treatment purposes. It is on the World Health Organization's List of Essential Medicines.<ref name="WHO21st">Template:Cite book</ref> In 2000, worldwide production was estimated at 30,000 tons.<ref name="WHO21st" />

PropertiesEdit

Potassium permanganate is the potassium salt of the tetrahedral transition metal oxo complex permanganate, in which four Template:Chem2 ligands are bound to a manganese(VII) center.Template:Citation needed

StructureEdit

Template:Chem2 forms orthorhombic crystals with constants: a = 910.5 pm, b = 572.0 pm, c = 742.5 pm. The overall motif is similar to that for barium sulfate, with which it forms solid solutions.<ref>Template:Cite book</ref> In the solid (as in solution), each Template:Chem2 centre is tetrahedral. The Mn–O distances are 1.62 Å.<ref>Template:Cite journal</ref>

ColorEdit

The purplish-black color of solid potassium permanganate, and the intensely pink to purple color of its solutions, is caused by its permanganate anion, which gets its color from a strong charge-transfer absorption band caused by excitation of electrons from oxo ligand orbitals to empty orbitals of the manganese(VII) center.<ref>Template:Cite book</ref>

Medical usesEdit

{{#invoke:Labelled list hatnote|labelledList|Main article|Main articles|Main page|Main pages}}

Mechanism of actionEdit

Potassium permanganate functions as a strong oxidising agent.<ref name="Derm2017">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> Through this mechanism it results in disinfection, astringent effects, and decreased smell.<ref name="Derm2017" />

Clinical useEdit

Potassium permanganate is used for a number of skin conditions.<ref name="WHO2008" /> This includes fungal infections of the foot, impetigo, pemphigus, superficial wounds, dermatitis, and topical ulcers.<ref name="BNF69">Template:Cite book</ref><ref name="WHO2008">Template:Cite book</ref> Radioactive contamination of the skin can be cleaned with potassium permanganate and vigorous scrubbing. For topical ulcers it is used together with procaine benzylpenicillin.<ref name="WHO2008" /> Typically it is used in skin conditions that produce a lot of liquid.<ref name="BNF69" /> It can be applied as a soaked dressing or a bath.<ref name="WHO20082">Template:Cite book</ref> It can be used in children and adults.<ref name="WHO2017222">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> Petroleum jelly may be used on the nails before soaking to prevent their discoloration.<ref name="Ox2011">Template:Cite book</ref> For treating eczema, it is recommended using for only a few days at a time due to the possibility of it irritating the skin.<ref name="Nurse20033">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

The U.S. Food and Drug Administration does not recommend its use in the crystal or tablet form. It should only be used in a diluted liquid form.<ref name="FDA20172">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

Historical useEdit

Potassium permanganate was first made in the 1600s and came into common medical use at least as early as the 1800s.<ref name="Stout_2013">Template:Cite book</ref> During World War I Canadian soldiers were given potassium permanganate (to be applied mixed with an ointment) in an effort to prevent sexually transmitted infections.<ref>Template:Cite book</ref> Some have attempted to bring about an abortion by putting it in the vagina, though this is not effective.<ref>Template:Cite book</ref><ref>Template:Cite book</ref><ref name="FDA20172"/> Other historical uses have included an effort to wash out the stomach in those with strychnine or picrotoxin poisoning.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

Side effectsEdit

Side effects from topical use may include irritation of the skin and discoloration of clothing.<ref name="WHO20083">Template:Cite book</ref> A harsh burn on a child from an undissolved tablet has been reported.<ref name="Nurse20033"/> Higher concentration solutions can result in chemical burns.<ref>Template:Cite book</ref> Therefore, the British National Formulary recommends 100 mg be dissolved in a liter of water before use to form a 1:10,000 (0.01%) solution.<ref name="Nurse20033"/><ref name="BNF692">Template:Cite book</ref><ref name="WHO2017222"/> Wrapping the dressings soaked with potassium permanganate is not recommended.Template:Citation needed

Potassium permanganate is toxic if taken by mouth.<ref>Template:Cite book</ref> Side effects may include nausea, vomiting, and shortness of breath may occur.<ref name="Patnaik_2007">Template:Cite book</ref> If a sufficiently large amount (about 10 grams) is eaten death may occur.<ref name="Patnaik_2007" />

Concentrated solutions when drunk have resulted in acute respiratory distress syndrome or swelling of the airway.<ref name="Schonwald_2004">Template:Cite book</ref> Recommended measures for those who have ingested potassium permanganate include gastroscopy.<ref name="Schonwald_2004" /> Activated charcoal or medications to cause vomiting are not recommended. While medications like ranitidine and acetylcysteine may be used in toxicity, evidence for this use is poor.<ref name="Schonwald_2004" />

PharmaceuticalsEdit

In the United States the FDA requires tablets of the medication to be sold by prescription.<ref name="FDA20172"/> Potassium permanganate, however, does not have FDA approved uses and therefore non medical grade potassium permanganate is sometimes used for medical purposes.Template:Citation needed

It is available under a number of brand names including Permasol, Koi Med Tricho-Ex, and Kalii permanganas RFF.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> It is occasionally called "Condy's crystals".<ref name="Derm20172">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

Veterinary medicineEdit

Potassium permanganate may be used to prevent the spread of glanders among horses.<ref>Template:Cite book</ref>

Industrial and other usesEdit

Almost all applications of potassium permanganate exploit its oxidizing properties.<ref name="Ullmann" /> As a strong oxidant that does not generate toxic byproducts, KMnO4 has many niche uses.Template:Citation needed

Water treatmentEdit

Potassium permanganate is used extensively in the water treatment industry. It is used as a regeneration chemical to remove iron and hydrogen sulfide (rotten egg smell) from well water via a "manganese greensand" filter. "Pot-Perm" is also obtainable at pool supply stores and is used additionally to treat wastewater. Historically it was used to disinfect drinking water<ref>Template:Cite book</ref><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> and can turn the water pink.<ref>Template:Cite news</ref> Modern hiking and survivalist guides advise against using potassium permanganate in the field because it is difficult to dose correctly.<ref>Template:Cite book</ref> It currently finds application in the control of nuisance organisms such as zebra mussels in fresh water collection and treatment systems.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

Synthesis of organic compoundsEdit

File:KMnO4 in H2O.jpg
A solution of KMnO4 in water, in a volumetric flask

A major application of KMnO4 is as a reagent for the synthesis of organic compounds.<ref>Template:Cite journal</ref> Significant amounts are required for the synthesis of ascorbic acid, chloramphenicol, saccharin, isonicotinic acid, and pyrazinoic acid.<ref name="Ullmann" />

KMnO4 is used in qualitative organic analysis to test for the presence of unsaturation. It is sometimes referred to as Baeyer's reagent after the German organic chemist Adolf von Baeyer. The reagent is an alkaline solution of potassium permanganate. Reaction with double or triple bonds (Template:Chem2 or Template:Chem2) causes the color to fade from purplish-pink to brown. Aldehydes and formic acid (and formates) also give a positive test.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> The test is antiquated.

KMnO4 solution is a common thin layer chromatography (TLC) stain for the detection of oxidizable functional groups, such as alcohols, aldehydes, alkenes, and ketones. Such compounds result in a white to orange spot on TLC plates.<ref>Thin Layer Chromatography stains http://www.reachdevices.com/TLC_stains.html</ref><ref>Jork, H., Funk, W., Fischer, W., Wimmer, H. (1990): Thin-Layer Chromatography: Reagents and Detection Methods, Volume 1a, VCH, Weinheim, Template:ISBN</ref><ref>Jork, H., Funk, W., Fischer, W., Wimmer, H. (1994): Thin-Layer Chromatography: Reagents and Detection Methods, Volume 1b, VCH, Weinheim</ref>

Analytical useEdit

Potassium permanganate can be used to quantitatively determine the total oxidizable organic material in an aqueous sample. The value determined is known as the permanganate value. In analytical chemistry, a standardized aqueous solution of KMnO4 is sometimes used as an oxidizing titrant for redox titrations (permanganometry). As potassium permanganate is titrated, the solution becomes a light shade of purple, which darkens as excess of the titrant is added to the solution. In a related way, it is used as a reagent to determine the Kappa number of wood pulp. For the standardization of KMnO4 solutions, reduction by oxalic acid is often used.<ref>Template:Cite journal</ref> In agricultural chemistry, it is used for estimation of active carbon in soil.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

Aqueous, acidic solutions of KMnO4 are used to collect gaseous mercury in flue gas during stationary source emissions testing.<ref>Code of Federal Regulations(7-1-07) Edition, Title 40, Part 60, Appendix A-8, Method 29, Section 7.3.1</ref>

In histology, potassium permanganate was used as a bleaching agent.<ref name="Picken_2010">Template:Cite journal</ref><ref name="Murphy_2001">Template:Cite journal</ref>

Fruit preservationEdit

Ethylene absorbents extend storage time of bananas even at high temperatures. This effect can be exploited by packing bananas in polyethylene together with potassium permanganate. By removing ethylene by oxidation, the permanganate delays the ripening, increasing the fruit's shelf life up to 4 weeks without the need for refrigeration.<ref>Template:Cite journal</ref><ref>Template:Cite journal</ref><ref>Template:Cite journal</ref>

The chemical reaction, in which ethylene (C2H4) is oxidised by potassium permanganate (KMnO4) to carbon dioxide (CO2), manganese oxide (MnO2) and potassium hydroxide (KOH), in the presence of water, is presented as follows:<ref>Template:Cite journal</ref>

3 C2H4 + 12 KMnO4 + 2 H2O → 6 CO2 + 2 H2O + 12 MnO2 + 12 KOH

Survival kitsEdit

Potassium permanganate is sometimes included in survival kits: as a hypergolic fire starter (when mixed with glycerol antifreeze from a car radiator);<ref name="Bob Gillis and Dino Labiste">{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> as a water sterilizer; and for creating distress signals on snow.<ref>Template:Cite journal</ref>

Fire serviceEdit

Potassium permanganate is added to "plastic sphere dispensers" to create backfires, burnouts, and controlled burns. Polymer spheres resembling ping-pong balls containing small amounts of permanganate are injected with ethylene glycol and projected towards the area where ignition is desired, where they spontaneously ignite seconds later.<ref name=usfs>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref><ref name=dj>Template:Cite episode</ref> Both handheldTemplate:R helicopter-Template:R unmanned aircraft systems (UAS) or boat-mountedTemplate:R plastic sphere dispensers are used.

Other usesEdit

Potassium permanganate is one of the principal chemicals used in the film and television industries to "age" props and set dressings. Its ready conversion to brown MnO2 creates "hundred-year-old" or "ancient" looks on hessian cloth (burlap), ropes, timber and glass.<ref>Template:Cite journal</ref>

Potassium permanganate can be used to oxidize cocaine paste to purify it and increase its stability. This led to the Drug Enforcement Administration launching Operation Purple in 2000, with the goal of monitoring the world supply of potassium permanganate; however, potassium permanganate derivatives and substitutes were soon used thereafter to avoid the operation.<ref>Template:Cite news</ref>

Potassium permanganate is used as an oxidizing agent in the synthesis of cocaine and methcathinone.<ref>Template:Cite journal</ref>

Potassium permanganate is one of a number of possible treatments for Ichthyophthirius multifiliis (commonly known as "ich"), a parasite that infects and usually kills freshwater aquarium fish.

HistoryEdit

In 1659, Johann Rudolf Glauber fused a mixture of the mineral pyrolusite (manganese dioxide, MnO2) and potassium carbonate to obtain a material that, when dissolved in water, gave a green solution (potassium manganate) which slowly shifted to violet and then finally red.<ref>Glauber, Johann Rudolph, Prosperitas Germaniae (The prosperity of Germany), part 3 (Amsterdam, (Netherlands): Johann Jansson, 1659), pp. 93–94. From pp. 93–94: " … donec tandem Magnesiam istam nitro fixo permixtam, in crucibulo forti coctione a nitro reseratam vidi, unde elegans color purpureus provenit, massam hanc effusam in pulvere redegi, aqua calida extraxi, per filtrum liquorem transmisi. Tandem vero elegantissimum purpureum, igneumque liquorem accepi, qui fere singulis horis in frigore tantummodo consistens colorem permutavit, sic ut jam viridis, jam caerulei, jam sanguinei coloris sponte sua factus sit, mox iterum alios elegantissimos colores receperit." ( … until finally I saw [that] by mixing that magnesia [i.e., magnesia nigra, pyrolusite, the ore containing manganese dioxide ] with fixed niter [i.e., inert niter, potassium carbonate], by cooking [it] in a strong crucible, [the colored compound was] released by the niter, whence a fine purple color arises; this mass [was] poured out, reduced to powder, extracted with hot water, [and] the solution passed through a filter. Then I got a truly most elegant, purple, and fiery solution, which nearly every hour ([while] standing just in the cold) changed color, so that it was spontaneously made now green, now blue, now red in color; soon again it received other most elegant colors.) {{#invoke:citation/CS1|citation |CitationClass=web }} Translated in: Template:Cite book</ref> The reaction that produced the color changes that Glauber observed in his solution of potassium permanganate and potassium manganate (K2MnO4) is now known as the "chemical chameleon".<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref> This report represents the first description of the production of potassium permanganate.<ref>Template:Cite book</ref> Just under 200 years later, London chemist Henry Bollmann Condy had an interest in disinfectants; he found that fusing pyrolusite with sodium hydroxide (NaOH) and dissolving it in water produced a solution with disinfectant properties. He patented this solution, and marketed it as 'Condy's Fluid'. Although effective, the solution was not very stable. This was overcome by using potassium hydroxide (KOH) rather than NaOH. This was more stable, and had the advantage of easy conversion to the equally effective potassium permanganate crystals. This crystalline material was known as 'Condy's crystals' or 'Condy's powder'. Potassium permanganate was comparatively easy to manufacture, so Condy was subsequently forced to spend considerable time in litigation to stop competitors from marketing similar products.<ref>Template:Cite journal</ref> According to Varlam Shalamov, potassium permanganate solution was used as a catch-all treatment for dysentery, frostbite and ulcers in the Gulag camps of Kolyma.

Early photographers used it as a component of flash powder. It is now replaced with other oxidizers, due to the instability of permanganate mixtures.Template:Citation needed

PreparationEdit

Potassium permanganate is produced industrially from manganese dioxide, which also occurs as the mineral pyrolusite. In 2000, worldwide production was estimated at 30,000 tonnes.<ref name="Ullmann">Template:Ullmann</ref> The MnO2 is fused with potassium hydroxide and heated in air or with another source of oxygen, like potassium nitrate or potassium chlorate.<ref name="Ullmann"/> This process gives potassium manganate:

Template:Chem2

With sodium hydroxide, the end product is not sodium manganate but a Mn(V) compound, which is one reason why the potassium permanganate is more commonly used than sodium permanganate. Furthermore, the potassium salt crystallizes better.<ref name="Ullmann"/>

The potassium manganate is then converted into permanganate by electrolytic oxidation in alkaline media:

Template:Chem2

Other methodsEdit

Although of no commercial importance, potassium manganate can be oxidized by chlorine or by disproportionation under acidic conditions.<ref>Template:Cite book</ref> The chlorine oxidation reaction is

Template:Chem2

and the acid-induced disproportionation reaction may be written as

Template:Chem2

A weak acid such as carbonic acid is sufficient for this reaction:

Template:Chem2

Permanganate salts may also be generated by treating a solution of Mn2+ ions with strong oxidants such as lead dioxide (PbO2), sodium bismuthate (NaBiO3), or peroxydisulfate. Tests for the presence of manganese exploit the vivid violet color of permanganate produced by these reagents.

ReactionsEdit

Organic chemistryEdit

Dilute solutions of KMnO4 convert alkenes into diols. This behaviour is also used as a qualitative test for the presence of double or triple bonds in a molecule, since the reaction decolorizes the initially purple permanganate solution and generates a brown precipitate (MnO2). In this context, it is sometimes called Baeyer's reagent. However, bromine serves better in measuring unsaturation (double or triple bonds) quantitatively, since KMnO4, being a very strong oxidizing agent, can react with a variety of groups.

Under acidic conditions, the alkene double bond is cleaved to give the appropriate carboxylic acid:<ref>Template:OrgSynth</ref>

Template:Chem2

Potassium permanganate oxidizes aldehydes to carboxylic acids, illustrated by the conversion of n-heptanal to heptanoic acid:<ref>Template:OrgSynth</ref>

Template:Chem2

Even an alkyl group (with a benzylic hydrogen) on an aromatic ring is oxidized, e.g. toluene to benzoic acid.<ref>Template:Cite journal</ref>

Template:Chem2

Glycols and polyols are highly reactive toward KMnO4. For example, addition of potassium permanganate to an aqueous solution of sugar and sodium hydroxide produces the chemical chameleon reaction, which involves dramatic color changes associated with the various oxidation states of manganese. A related vigorous reaction is exploited as a fire starter in survival kits. For example, a mixture of potassium permanganate and glycerol or pulverized glucose ignites readily.<ref name="Bob Gillis and Dino Labiste"/> Its sterilizing properties are another reason for inclusion of KMnO4 in a survival kit.Template:Citation needed

Ion exchangeEdit

Treating a mixture of aqueous potassium permanganate with a quaternary ammonium salt results in ion exchange, precipitating the quat salt of permanganate. Solutions of these salts are sometimes soluble in organic solvents:<ref>Template:Cite journal</ref>

Template:Chem2

Similarly, addition of a crown ether also gives a lipophilic salt.<ref>Template:Cite journal</ref>

Reaction with acids and basesEdit

Permanganate reacts with concentrated hydrochloric acid to give chlorine and manganese(II):

Template:Chem2

In neutral solution, permanganate slowly reduces to manganese dioxide (MnO2). This is the material that stains one's skin when handling KMnO4.

KMnO4 reduces in alkaline solution to give green K2MnO4:<ref>Template:Cite book</ref>

Template:Chem2

This reaction illustrates the relatively rare role of hydroxide as a reducing agent.

Addition of concentrated sulfuric acid to potassium permanganate gives Mn2O7.<ref>Template:Cite book</ref> Although no reaction may be apparent, the vapor over the mixture will ignite paper impregnated with alcohol. Potassium permanganate and sulfuric acid react to produce some ozone, which has a high oxidizing power and rapidly oxidizes the alcohol, causing it to combust. As the reaction also produces explosive Mn2O7, this should only be attempted with great caution.<ref>Template:Cite journal</ref><ref>Template:Cite journal</ref>

Thermal decompositionEdit

Solid potassium permanganate decomposes when heated:

Template:Chem2

It is a redox reaction.

Safety and handlingEdit

Potassium permanganate poses risks as an oxidizer.<ref name="Bretherick_2007">Template:Cite book</ref> Contact with skin can cause skin irritation and in some cases severe allergic reaction. It can also result in discoloration and clothing stains.<ref>{{#invoke:citation/CS1|citation |CitationClass=web }}</ref>

ReferencesEdit

Template:Reflist

Further readingEdit

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External linksEdit

Template:Permanganates Template:Potassium compounds Template:Antiseptics and disinfectants Template:Antidotes Template:Organic reactions Template:Portal bar