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| A '''peroxy acid''' (often spelled as one word, '''peroxyacid''', and sometimes called '''peracid''') is an [[acid]] which contains an acidic -OOH group. The two main classes are those derived from conventional mineral acids, especially sulfuric acid, and the organic derivatives of carboxylic acids. They are generally strong [[oxidizer]]s.
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| ==Inorganic peroxy acids==
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| {{main|Peroxymonosulfuric acid}}
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| [[Peroxymonosulfuric acid]] (Caro's acid) is probably the most important inorganic peracid, at least in terms of the scale.<ref>{{Ullmann | author = Harald Jakob et al. | title = Peroxy Compounds, Inorganic | doi = 10.1002/14356007.a19_177.pub2}}</ref> It is used for the bleaching of [[pulp (paper)|pulp]] and for the detoxification of cyanide in the mining industry. It is produced by treating sulfuric acid with [[hydrogen peroxide]]. Peroxyphosphoric acid (H<sub>3</sub>PO<sub>5</sub>) is prepared similarly.
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| ==Organic peracids==
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| Several organic peroxyacids are commercially useful.<ref>{{Ullmann | author = Herbert Klenk, Peter H. Götz, Rainer Siegmeier, Wilfried Mayr | title = Peroxy Compounds, Organic | doi = 10.1002/14356007.a19_199}}</ref> They can be prepared in several ways. Most commonly, peracids are generated by treating the corresponding [[carboxylic acid]] with hydrogen peroxide:
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| :RCO<sub>2</sub>H + H<sub>2</sub>O<sub>2</sub> <math>\overrightarrow{\leftarrow}</math> RCO<sub>3</sub>H + H<sub>2</sub>O
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| A related reaction involves treatment of the carboxylic anhydride:
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| :(RCO)<sub>2</sub>O + H<sub>2</sub>O<sub>2</sub> → RCO<sub>3</sub>H + RCO<sub>2</sub>H
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| This method is popular for converting cyclic anhydrides to the corresponding monoperoxyacids, for example monoperoxyphthalic acid.<br>
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| The third method involves treatment of [[acid chloride]]s:
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| :RC(O)Cl + H<sub>2</sub>O<sub>2</sub> → RCO<sub>3</sub>H + HCl | |
| [[Meta-Chloroperoxybenzoic acid|''meta''-chloroperoxybenzoic acid]] (mCPBA) is prepared in this way.
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| ===Properties and uses===
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| Peroxycarboxylic acids are about 1000x weaker than the parent carboxylic acid, owing the absence of resonance stabilization of the anion. For similar reasons, their pK<sub>a</sub>s tend also to be relatively insensitive to the substituent R.
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| The largest use of organic peroxy acids is for the conversion of alkenes to epoxides. Certain cyclic ketones are converted to the ring-expanded esters using peracids in a [[Baeyer-Villiger oxidation]]. They are also used for the oxidation of [[amine]]s and [[thioether]]s to [[amine oxide]]s and [[sulfoxide]]s. The laboratory applications of the valued reagent [[mCPBA]] illustrate these reactions. It is used as a [[reagent]] in the Baeyer-Villiger oxidation and in oxidation of [[carbon]]-carbon [[double bond]]s in [[alkene]]s to generate [[epoxide]]s (oxiranes). Reaction of peroxycarboxylic acids with acid chlorides affords diacyl peroxides:
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| :RC(O)Cl + RC<sub>2</sub>O<sub>2</sub>H → (RCO)<sub>2</sub>O<sub>2</sub> + HCl
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| ==See also==
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| * [[Organic peroxide]]
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| * [[Meta-Chloroperoxybenzoic acid]]
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| * [[Peracetic acid]]
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| * [[Peroxyacyl nitrates]]
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| ==References==
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| <references/>
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| {{DEFAULTSORT:Peroxy Acid}}
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| [[Category:Oxidizing agents]]
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| [[Category:Peroxy acids]]
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| [[Category:Functional groups]]
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