Peroxymonosulfuric acid: Difference between revisions

Peroxymonosulfuric acid
Names
	IUPAC names Peroxysulfuric acid; Sulfuroperoxoic acid
	Systematic IUPAC name (Dioxidanido)hydroxidodioxidosulfur
	Other names Peroxosulfuric acid; Peroxomonosulfuric acid[citation needed]; Persulfuric acid[citation needed]; Caro's acid
Identifiers
CAS Number	7722-86-3 ;
3D model (JSmol)	Interactive image; Interactive image;
ChEBI	CHEBI:29286 ;
ChemSpider	2035480 ;
ECHA InfoCard	100.028.879
EC Number	231-766-6;
Gmelin Reference	101039
PubChem CID	2754594;
UNII	JC6U8R2UJ9 ;
UN number	1483
CompTox Dashboard (EPA)	DTXSID90884417 ;
	InChI InChI=1S/H2O5S/c1-5-6(2,3)4/h1H,(H,2,3,4) Key: FHHJDRFHHWUPDG-UHFFFAOYSA-N ;
	SMILES OOS(O)(=O)=O; [O].[O].OOSO;
Properties
Chemical formula	H; 2SO; 5
Molar mass	114.078 g mol−1
Appearance	White crystals
Density	2.239 g cm−3
Melting point	45 °C
Acidity (pKa)	1, 9.3
Conjugate base	Peroxomonosulfate
Structure
Coordination geometry	Tetrahedral at S
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	strong oxidizer
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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Peroxymonosulfuric acid, also known as persulfuric acid, peroxysulfuric acid is the inorganic compound with the formula H₂SO₅. It is a white solid. It is a component of Caro's acid, which is a solution of peroxymonosulfuric acid in sulfuric acid containing small amounts of water.^[4] Peroxymonosulfuric acid is a very strong oxidant (E⁰ = +2.51 V).

Structure

In peroxymonosulfuric acid, the S(VI) center adopts its characteristic tetrahedral geometry; the connectivity is indicated by the formula HO–O–S(O)₂–OH. The S-O-H proton is more acidic.^[4]

History

The German chemist Heinrich Caro first reported investigations of mixtures of hydrogen peroxide and sulfuric acid.^[5]

Synthesis and production

One laboratory scale preparation of Caro's acid involves the combination of chlorosulfuric acid and hydrogen peroxide:^[6]

H₂O₂ + ClSO₂OH ⇌ H₂SO₅ + HCl

Patents include more than one reaction for preparation of Caro's acid, usually as an intermediate for the production of potassium monopersulfate (PMPS), a bleaching and oxidizing agent. One route employs the following reaction:^[7]

H₂O₂ + H₂SO₄ ⇌ H₂SO₅ + H₂O

This reaction is related to "piranha solution".

Uses in industry

H
₂SO
₅ and Caro's acid have been used for a variety of disinfectant and cleaning applications, e.g., swimming pool treatment and denture cleaning. It is used in gold mining to destroy the cyanide in the waste stream ("Tailings").

Alkali metal salts of H
₂SO
₅, especially oxone, are widely investigated.

Hazards

These peroxy acids can be explosive. Explosions have been reported at Brown University^[8] and Sun Oil. As with all strong oxidizing agents, peroxysulfuric acid is incompatible with organic compounds.

References

^ ^a ^b ^c International Union of Pure and Applied Chemistry (2005). Nomenclature of Inorganic Chemistry (IUPAC Recommendations 2005). Cambridge (UK): RSC–IUPAC. ISBN 0-85404-438-8. p. 139. Electronic version.
^ "Peroxysulfuric acid (CHEBI:29286)". Chemical Entities of Biological Interest. UK: European Bioinformatics Institute. 20 November 2007. Retrieved 17 November 2011.
^ Perrin, D. D., ed. (1982) [1969]. Ionisation Constants of Inorganic Acids and Bases in Aqueous Solution. IUPAC Chemical Data (2nd ed.). Oxford: Pergamon (published 1984). Entry 176. ISBN 0-08-029214-3. LCCN 82-16524.
^ ^a ^b Jakob, Harald; Leininger, Stefan; Lehmann, Thomas; Jacobi, Sylvia; Gutewort, Sven (2007). "Peroxo Compounds, Inorganic". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a19_177.pub2. ISBN 978-3-527-30673-2.
^ Caro, H. (1898). "Zur Kenntniss der Oxydation aromatischer Amine" [[Contribution] to [our] knowledge of the oxidation of aromatic amines]. Zeitschrift für angewandte Chemie. 11 (36): 845–846. doi:10.1002/ange.18980113602.
^ "Synthesis of Caro's acid". PrepChem.com. 2017-02-13. Retrieved 2018-10-12.
^ A method and apparatus for producing a peroxyacid solution, retrieved 2018-10-12
^ Edwards, J.O. (1955). "Safety". Chem. Eng. News. 33 (32): 3336. doi:10.1021/cen-v033n032.p3336.

[redbookname-1] International Union of Pure and Applied Chemistry (2005). Nomenclature of Inorganic Chemistry (IUPAC Recommendations 2005). Cambridge (UK): RSC–IUPAC. ISBN 0-85404-438-8. p. 139. Electronic version.

[2] "Peroxysulfuric acid (CHEBI:29286)". Chemical Entities of Biological Interest. UK: European Bioinformatics Institute. 20 November 2007. Retrieved 17 November 2011.

[P82db-3] Perrin, D. D., ed. (1982) [1969]. Ionisation Constants of Inorganic Acids and Bases in Aqueous Solution. IUPAC Chemical Data (2nd ed.). Oxford: Pergamon (published 1984). Entry 176. ISBN 0-08-029214-3. LCCN 82-16524.

[Ullmann-4] Jakob, Harald; Leininger, Stefan; Lehmann, Thomas; Jacobi, Sylvia; Gutewort, Sven (2007). "Peroxo Compounds, Inorganic". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a19_177.pub2. ISBN 978-3-527-30673-2.

[5] Caro, H. (1898). "Zur Kenntniss der Oxydation aromatischer Amine" [[Contribution] to [our] knowledge of the oxidation of aromatic amines]. Zeitschrift für angewandte Chemie. 11 (36): 845–846. doi:10.1002/ange.18980113602.

[PrepChem-6] "Synthesis of Caro's acid". PrepChem.com. 2017-02-13. Retrieved 2018-10-12.

[Martin_patent-7] A method and apparatus for producing a peroxyacid solution, retrieved 2018-10-12

[8] Edwards, J.O. (1955). "Safety". Chem. Eng. News. 33 (32): 3336. doi:10.1021/cen-v033n032.p3336.

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@@ Line 51: / Line 51: @@
 }}
 }}
-'''Peroxymonosulfuric acid''', {{chem2|H2SO5}}, is also known as '''persulfuric acid''', '''peroxysulfuric acid'''.  It is a white solid.  It is closely related to '''Caro's acid''', which is a solution of peroxymonosulfuric acid in sulfuric acid containing small amounts of water.<ref>{{cite journal |doi=10.1002/14356007.a19_177.pub2}}</ref>  It is one of the strongest oxidants known ([[Electrode potential|''E''<sup>0</sup>]]&nbsp;= +2.51&nbsp;V).
+'''Peroxymonosulfuric acid''', also known as '''persulfuric acid''', '''peroxysulfuric acid''' is the [[inorganic compound]] with the formula {{chem2|H2SO5}}.  It is a white solid.  It is a component of '''Caro's acid''', which is a solution of peroxymonosulfuric acid in [[sulfuric acid]] containing small amounts of water.<ref name=Ullmann/>  Peroxymonosulfuric acid is a very strong oxidant ([[Electrode potential|''E''<sup>0</sup>]]&nbsp;= +2.51&nbsp;V).
 ==Structure==
-In peroxymonosulfuric acid, the S(VI) center adopts its characteristic tetrahedral geometry; the connectivity is indicated by the formula HO–O–S(O)<sub>2</sub>–OH. The S-O-''H'' proton is more acidic.<ref>{{cite book |doi=10.1002/14356007.a19_177.pub2 |chapter=Peroxo Compounds, Inorganic |title=Ullmann's Encyclopedia of Industrial Chemistry |date=2007 |last1=Jakob |first1=Harald |last2=Leininger |first2=Stefan |last3=Lehmann |first3=Thomas |last4=Jacobi |first4=Sylvia |last5=Gutewort |first5=Sven |isbn=978-3-527-30673-2 }}</ref>
+In peroxymonosulfuric acid, the S(VI) center adopts its characteristic tetrahedral geometry; the connectivity is indicated by the formula HO–O–S(O)<sub>2</sub>–OH. The S-O-''H'' proton is more acidic.<ref name=Ullmann>{{cite book |doi=10.1002/14356007.a19_177.pub2 |chapter=Peroxo Compounds, Inorganic |title=Ullmann's Encyclopedia of Industrial Chemistry |date=2007 |last1=Jakob |first1=Harald |last2=Leininger |first2=Stefan |last3=Lehmann |first3=Thomas |last4=Jacobi |first4=Sylvia |last5=Gutewort |first5=Sven |isbn=978-3-527-30673-2 }}</ref>
 ==History==
@@ Line 60: / Line 60: @@
 ==Synthesis and production==
-The laboratory scale preparation of Caro's acid involves the combination of [[chlorosulfuric acid]] and [[hydrogen peroxide]]:<ref name="PrepChem">{{Cite web |url=http://www.prepchem.com/synthesis-caros-acid/ |title=Synthesis of Caro's acid |date=2017-02-13 |website=PrepChem.com |language=en-US |access-date=2018-10-12}}</ref>
+One laboratory scale preparation of Caro's acid involves the combination of [[chlorosulfuric acid]] and [[hydrogen peroxide]]:<ref name="PrepChem">{{Cite web |url=http://www.prepchem.com/synthesis-caros-acid/ |title=Synthesis of Caro's acid |date=2017-02-13 |website=PrepChem.com |language=en-US |access-date=2018-10-12}}</ref>
 :{{chem2 | H2O2 + ClSO2OH <-> H2SO5 + HCl }}
@@ Line 70: / Line 70: @@
 ==Uses in industry==
+{{Chem|H|2|S|O|5}} and Caro's acid have been used for a variety of disinfectant and cleaning applications, e.g., swimming pool treatment and denture cleaning.  It is used in [[gold mining]]  to destroy the [[cyanide]] in the waste stream ("[[Tailings]]").
-{{Chem|H|2|S|O|5}} has been used for a variety of disinfectant and cleaning applications, e.g., swimming pool treatment and denture cleaning.  It is sometimes used in [[gold]] [[mining]] process plants to destroy the [[cyanide]] in the waste stream ("[[Tailings]]"), thus rendering this material safe to store without risking contamination of the environment. Alkali metal salts of {{Chem|H|2|S|O|5}} show promise for the [[lignin|delignification]] of wood.<ref>{{cite journal |title=Treatment of softwood kraft pulps with peroxymonosulfate before oxygen delignification |last=Springer |first=E. L. |last2=McSweeny |first2=J. D. |journal=TAPPI Journal |year=1993 |volume=76 |issue=8 |pages=194–199 |url=http://www.tappi.org/Bookstore/Technical-Papers/Journal-Articles/TAPPI-JOURNAL/Archives/1993/August/Treatment-of-softwood-kraft-pulps-with-peroxymonosulfate-before-oxygen-delignification-TAPPI-JOURNA.aspx |issn=0734-1415 |access-date=2011-05-14 |archive-url=https://web.archive.org/web/20110929012348/http://www.tappi.org/Bookstore/Technical-Papers/Journal-Articles/TAPPI-JOURNAL/Archives/1993/August/Treatment-of-softwood-kraft-pulps-with-peroxymonosulfate-before-oxygen-delignification-TAPPI-JOURNA.aspx |archive-date=2011-09-29 |url-status=dead }}</ref> It is also used in laboratories as a last resort in removing organic materials since {{Chem|H|2|S|O|5}} can fully [[oxidize]] any organic materials.{{citation needed|date=June 2020}}
+Alkali metal salts of {{Chem|H|2|S|O|5}}, especially [[oxone]], are widely investigated.
-[[Ammonium]], [[sodium]], and [[potassium]] salts of {{Chem|H|2|S|O|5}} are used in the [[plastics industry]] as [[radical initiator]]s for [[polymerization]]. They are also used as [[etching|etchants]], [[Desizing#Oxidative desizing|oxidative desizing]] agents for textile fabrics, and for decolorizing and deodorizing oils.
-[[Potassium peroxymonosulfate]], {{Chem|K|H|S|O|5}}, is the [[potassium]] [[acid salt]] of peroxymonosulfuric acid. It is widely used as an [[oxidizing agent]].
 ==Hazards==
-Pure Caro's acid is highly explosive. Explosions have been reported at [[Brown University]]<ref>{{cite journal | last1 = Edwards | first1 = J.O. | journal = [[Chem. Eng. News]] | volume = 33 | pages = 3336 | year = 1955 | doi = 10.1021/cen-v033n032.p3336 | title = Safety | issue = 32}}</ref> and [[Sun Oil]]. As with all strong oxidizing agents, peroxysulfuric acid should be kept away from organic compounds such as ethers and ketones because of its ability to peroxidize these compounds, creating highly unstable molecules such as [[acetone peroxide]].
+These peroxy acids can be explosive. Explosions have been reported at [[Brown University]]<ref>{{cite journal | last1 = Edwards | first1 = J.O. | journal = [[Chem. Eng. News]] | volume = 33 | pages = 3336 | year = 1955 | doi = 10.1021/cen-v033n032.p3336 | title = Safety | issue = 32}}</ref> and [[Sun Oil]]. As with all strong oxidizing agents, peroxysulfuric acid is incompatible with [[organic compound]]s.
 ==See also==