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[[File:Peracid Acid General Formulae V.1.png|right|thumb|160px|General formulae of an organic peroxy acid (top) compared with a carboxylic acid (bottom).]] | |||
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. | |||
==Inorganic peroxy acids== | |||
{{main|Peroxymonosulfuric acid}} | |||
[[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. | |||
==Organic peracids== | |||
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: | |||
: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 | |||
A related reaction involves treatment of the carboxylic anhydride: | |||
:(RCO)<sub>2</sub>O + H<sub>2</sub>O<sub>2</sub> → RCO<sub>3</sub>H + RCO<sub>2</sub>H | |||
This method is popular for converting cyclic anhydrides to the corresponding monoperoxyacids, for example monoperoxyphthalic acid.<br> | |||
The third method involves treatment of [[acid chloride]]s: | |||
: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. | |||
===Properties and uses=== | |||
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. | |||
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: | |||
:RC(O)Cl + RC<sub>2</sub>O<sub>2</sub>H → (RCO)<sub>2</sub>O<sub>2</sub> + HCl | |||
==See also== | |||
* [[Organic peroxide]] | |||
* [[Meta-Chloroperoxybenzoic acid]] | |||
* [[Peracetic acid]] | |||
* [[Peroxyacyl nitrates]] | |||
==References== | |||
<references/> | |||
{{DEFAULTSORT:Peroxy Acid}} | |||
[[Category:Oxidizing agents]] | |||
[[Category:Peroxy acids]] | |||
[[Category:Functional groups]] | |||
Revision as of 18:37, 14 January 2014
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 oxidizers.
Inorganic peroxy acids
Mining Engineer (Excluding Oil ) Truman from Alma, loves to spend time knotting, largest property developers in singapore developers in singapore and stamp collecting. Recently had a family visit to Urnes Stave Church. Peroxymonosulfuric acid (Caro's acid) is probably the most important inorganic peracid, at least in terms of the scale.[1] It is used for the bleaching of pulp and for the detoxification of cyanide in the mining industry. It is produced by treating sulfuric acid with hydrogen peroxide. Peroxyphosphoric acid (H3PO5) is prepared similarly.
Organic peracids
Several organic peroxyacids are commercially useful.[2] They can be prepared in several ways. Most commonly, peracids are generated by treating the corresponding carboxylic acid with hydrogen peroxide:
A related reaction involves treatment of the carboxylic anhydride:
- (RCO)2O + H2O2 → RCO3H + RCO2H
This method is popular for converting cyclic anhydrides to the corresponding monoperoxyacids, for example monoperoxyphthalic acid.
The third method involves treatment of acid chlorides:
- RC(O)Cl + H2O2 → RCO3H + HCl
meta-chloroperoxybenzoic acid (mCPBA) is prepared in this way.
Properties and uses
Peroxycarboxylic acids are about 1000x weaker than the parent carboxylic acid, owing the absence of resonance stabilization of the anion. For similar reasons, their pKas tend also to be relatively insensitive to the substituent R.
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 amines and thioethers to amine oxides and sulfoxides. 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 bonds in alkenes to generate epoxides (oxiranes). Reaction of peroxycarboxylic acids with acid chlorides affords diacyl peroxides:
- RC(O)Cl + RC2O2H → (RCO)2O2 + HCl