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Revision as of 23:26, 23 January 2011 editWolfmanSF (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers156,372 editsm →Synthesis: wording← Previous edit Latest revision as of 11:33, 25 March 2024 edit undo213.78.162.233 (talk) →Properties and applications 
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{{chembox {{Chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 408957720
| Watchedfields = changed
⚫ | Name = Performic acid
⚫ | verifiedrevid = 409649915
⚫ | ImageFileL1 = Performic-acid-2D-skeletal.svg
⚫ | Name = Performic acid
| ImageSizeL1 = 120px
⚫ | ImageFileL1 = Performic Acid Structural Formula V.svg
| ImageNameL1 = Skeletal structure of performic acid | ImageNameL1 = Skeletal structure of performic acid
| ImageFileR1 = Performic-acid-3D-balls.png | ImageFileR1 = Performic-acid-3D-balls.png
| ImageSizeR1 = 120px
| ImageNameR1 = 3D model of performic acid | ImageNameR1 = 3D model of performic acid
| PIN = Methaneperoxoic acid<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 749 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}</ref>
| IUPACName =
| OtherNames = Hydroperoxyformaldehyde, formyl hydroperoxide, methaneperoxic acid, permethanoic acid, peroxyformic acid | OtherNames = Performic acid<br />Hydroperoxyformaldehyde<br />Formyl hydroperoxide<br />Permethanoic acid<br />Peroxyformic acid
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| SMILES = O=COO | SMILES = O=COO
⚫ | UNII_Ref = {{fdacite|correct|FDA}}=
| UNII =
| InChI =
| InChIKey =
⚫ | StdInChI_Ref = {{stdinchicite|correct|chemspider}}=
| StdInChI =
⚫ | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}=
| StdInChIKey =
| CASNo = 107-32-4 | CASNo = 107-32-4
| CASNo_Ref = {{cascite|correct|CAS}} | UNII_Ref = {{fdacite|changed|FDA}}
| ChEBI = | UNII = XEL6R975Q4
| PubChem = | PubChem = 66051
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = | ChemSpiderID = 59441
| RTECS = | EC_number = 600-819-9
⚫ | StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/CH2O3/c2-1-4-3/h1,3H
⚫ | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = SCKXCAADGDQQCS-UHFFFAOYSA-N
⚫ | CASNo_Ref = {{cascite|correct|??}}
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| C = 1|H = 2|O =3 | C=1 | H=2 | O=3
| Appearance = Colorless liquid | Appearance = Colorless liquid
| Density = | Density =
| Solubility = | Solubility =
| MeltingPtC = -18
| MeltingPt = -18 °C<ref name=u1>Elvers, B. ''et al.'' (ed.) (1991) Ullmann's Encyclopedia of Industrial Chemistry, 5th ed. Vol. A19, Wiley, p. 206</ref> | MeltingPt_ref = <ref name=u1>Elvers, B. ''et al.'' (ed.) (1991) Ullmann's Encyclopedia of Industrial Chemistry, 5th ed. Vol. A19, Wiley, p. 206</ref>
⚫ | BoilingPt = 50 °C(13.3 kPa; 90% pure acid)<ref name=u1/>
| BoilingPtC = 50
⚫ | pKa = 7.1<ref name=u1/><ref>F. A. Carroll , Wiley-Interscience, 2010, ISBN 047027610X p. 416</ref>
⚫ | BoilingPt_notes = (at 13.3 kPa; 90% pure acid)<ref name=u1/>
⚫ | pKa = 7.1<ref name=u1/><ref>F. A. Carroll , Wiley-Interscience, 2010, {{ISBN|0-470-27610-X}} p. 416</ref>
}} }}
| Section3 = {{Chembox Structure |Section3={{Chembox Structure
| MolShape = | MolShape =
| Dipole = | Dipole =
}} }}
| Section7 = {{Chembox Hazards |Section7={{Chembox Hazards
| ExternalMSDS = | ExternalSDS =
| MainHazards = | MainHazards =
| NFPA-H = | NFPA-H =
| NFPA-F = | NFPA-F =
| NFPA-R = | NFPA-R =
| FlashPt = | FlashPt =
| RPhrases = | HPhrases =
| SPhrases = | PPhrases =
| GHS_ref =
}}
⚫ |Section8={{Chembox Related
| OtherFunction_label =
| OtherFunction =
| OtherCompounds =
}} }}
⚫ | Section8 = {{Chembox Related
| Function =
| OtherFunctn =
| OtherCpds = }}
}} }}


'''Performic acid''' (PFA) is an ] with the ] CH<sub>2</sub>O<sub>3</sub>. It is an unstable colorless liquid which can be produced by mixing ] with ]. Owing to its oxidizing and disinfecting action, it is used in the chemical, medical and food industries. '''Performic acid''' (PFA) is an ] with the ] CH<sub>2</sub>O<sub>3</sub>. It is an unstable colorless liquid which can be produced by mixing ] with ]. Owing to its oxidizing and disinfecting action, it is used in the chemical, medical and food industries.


==Properties and applications== ==Properties and applications==
Performic acid is a colorless liquid soluble in water, alcohols, ], ], ] and other organic solvents.<ref name=j2/><ref name=b1/> Its strong oxidizing properties are used for cleaving ]s in protein mapping,<ref>{{cite journal|doi=10.1101/pdb.prot4698|last1=Simpson|year=2007|first1=R. J.|pages=pdb.prot4698|volume=2007|journal=Cold Spring Harbor Protocols|title=Performic Acid Oxidation of Proteins}}</ref> as well as for epoxidation, hydroxylation and oxidation reactions in organic synthesis.<ref name=b1>Pradyot Patnaik , Wiley-Interscience, 2007, ISBN 0471714585, p. 128</ref> In the medical and food industries, performic acid is commonly used to disinfect equipment. It is effective against viruses, bacterial spores, ], microscopic fungi and ], as well as other ]s as ]. The popularity of performic acid as a sterilizer originates from the safe nature of its degradation products, mostly ], oxygen and water.<ref name=j2/><ref>{{cite journal|last1=Gehr|first1=R|last2=Chen|first2=D|last3=Moreau|first3=M|title=Performic acid (PFA): tests on an advanced primary effluent show promising disinfection performance|url=http://www.iwaponline.com/wst/05901/0089/059010089.pdf|journal=Water science and technology : a journal of the International Association on Water Pollution Research|volume=59|issue=1|pages=89–96|year=2009|pmid=19151490|doi=10.2166/wst.2009.761}}</ref> The disinfecting action of performic acid is also faster than that of the related compounds ] and hydrogen peroxide.<ref name=pat2/> The major drawbacks of performic acid are handling dangers related to its high reactivity, as well as instability, especially upon heating, which means that the acid must be used within about 12 hours of it being synthesised.<ref name=pat2/><ref>{{cite journal|author=Bydzovska, O. and Merka, V. |year=1981 |title=Disinfecting Properties of Performic Acid Against Bacteriophage (X 174 as a Model of Small Envelope-free Viruses|pmid=6459365|journal=J. Hygiene, Epidemiology Microbiology and Immunology |volume=25|issue=4|pages=414–423}}</ref><ref>{{cite journal|title=Execution of a Performic Acid Oxidation on Multikilogram Scale|doi=10.1021/op700039r|author= Ripin, D.H.B. ''et al.''|year=2007|pages=762|volume=11|journal=Org. Process Res. Dev.}}</ref> Performic acid is a colorless liquid soluble in water, alcohols, ], ], ] and other organic solvents.<ref name=j2/><ref name=b1/> Its strong oxidizing properties are used for cleaving ]s in protein mapping,<ref>{{cite journal|doi=10.1101/pdb.prot4698|last1=Simpson|year=2007|first1=R. J.|pages=pdb.prot4698|volume=2007|journal=Cold Spring Harbor Protocols|title=Performic Acid Oxidation of Proteins|issue=3 }}</ref> as well as for epoxidation, hydroxylation<ref>{{cite journal |title=trans-1,2-CYCLOHEXANEDIOL |journal=Organic Syntheses |date=1948 |volume=28 |pages=35 |doi=10.15227/orgsyn.028.0035}}</ref> and oxidation reactions in organic synthesis.<ref name=b1>Pradyot Patnaik , Wiley-Interscience, 2007, {{ISBN|0-471-71458-5}}, p. 128</ref> In the medical and food industries, performic acid is commonly used to disinfect equipment. It is effective against viruses, bacterial spores, ], microscopic fungi and ], as well as other ]s such as ].
The popularity of performic acid as a sterilizer originates from the safe nature of its degradation products, mostly ], oxygen and water.<ref name=j2/><ref>{{cite journal|last1=Gehr|first1=R|last2=Chen|first2=D|last3=Moreau|first3=M|title=Performic acid (PFA): tests on an advanced primary effluent show promising disinfection performance|url=http://www.iwaponline.com/wst/05901/0089/059010089.pdf|journal=Water Science and Technology|volume=59|issue=1|pages=89–96|year=2009|pmid=19151490|doi=10.2166/wst.2009.761|url-status=dead|archiveurl=https://web.archive.org/web/20101116222519/http://www.iwaponline.com/wst/05901/0089/059010089.pdf|archivedate=2010-11-16}}</ref> The disinfecting action of performic acid is also faster than that of the related compounds ] and hydrogen peroxide.<ref name=pat2/> The major drawbacks of performic acid are handling dangers related to its high reactivity, as well as instability, especially upon heating, which means that the acid must be used within about 12 hours of it being synthesised.<ref name=pat2/><ref>{{cite journal|author1=Bydzovska, O. |author2=Merka, V. |name-list-style=amp |year=1981 |title=Disinfecting Properties of Performic Acid Against Bacteriophage (X 174 as a Model of Small Envelope-free Viruses|pmid=6459365|journal=J. Hygiene, Epidemiology Microbiology and Immunology |volume=25|issue=4|pages=414–423}}</ref><ref>{{cite journal|title=Execution of a Performic Acid Oxidation on Multikilogram Scale|doi=10.1021/op700039r|author= Ripin, D.H.B.|year=2007|pages=762–765|volume=11|journal=Org. Process Res. Dev.|issue=4 |display-authors=etal}}</ref>


==Synthesis== ==Synthesis==
Performic acid is synthesized by the reaction of ] and ] by the following ]:
Synthesis of pure performic acid has not been reported.<ref name=j2/> Aqueous solutions (up to 90%) can be prepared by mixing 70–98 wt.% of formic acid (in water) with 35–50 wt% of hydrogen peroxide.
:<math>\rm HCOOH + H_2O_2 \leftrightharpoons HCO_2OH + H_2O</math>


]
⚫ This reaction is reversible and can be used for large scale industrial production if accelerated with a ]; however, its temperature must be kept below 80–85 °C to avoid an explosion.<ref>Elvers, B. ''et al.'' (ed.) (1991) Ullmann's Encyclopedia of Industrial Chemistry, 5th ed. Vol. A12, Wiley, p. 16</ref> The catalyst can be ], ], ] or ] or their salts;<ref name=j2>{{cite journal|last1=Swern|first1=Daniel|title=Organic Peracids.|journal=Chemical Reviews|volume=45|pages=1|year=1949|doi=10.1021/cr60140a001|quote=In the absence of catalysts, performic acid explodes when heated rapidly to 80–85°C.}}</ref><ref>{{cite journal|doi=10.1021/ja01201a016|last1=English|first1=James|year=1947|pages=2120|volume=69|journal=Journal of the American Chemical Society|last2=Gregory|first2=J. Delafield|title=Performic Acid Hydroxylation of a,p-Unsaturated Acids and Esters}}</ref> it can also be an organic compound containing at least one ] group, such as ] ]<ref>Matilla, T. and Aksela, R. 2000 Method for the Preparation of Aqueous Solutions Containing Performic Acid as Well as Their Use. {{US Patent|6049002}}, Issue date: April 11, 2000</ref> or peracetic acid.<ref name=pat2>Preuss, A., Fuchs, R., Huss, M. & Schneider, R. 2001 Aqueous Disinfecting Agent Containing Performic Acid and Peracetic Acid Process for Production and Process for Use Thereof {{US Patent|6211237}}, Issue date: April 3, 2001</ref>

Synthesis of pure performic acid has not been reported, but aqueous solutions up to about 48% can be formed by simply mixing equimolar amounts of concentrated aqueous reactant solutions.<ref name=j2/> Using an excess of either reactant shifts the equilibrium towards the product side. The aqueous product solution can be distilled to increase the concentration of performic acid to about 90%.<ref name=j2/>

⚫ This reaction is reversible and can be used for large scale industrial production if accelerated with a ]; however, its temperature must be kept below 80–85&nbsp;°C to avoid an explosion.<ref>Elvers, B. ''et al.'' (ed.) (1991) Ullmann's Encyclopedia of Industrial Chemistry, 5th ed. Vol. A12, Wiley, p. 16</ref> The catalyst can be ], ], ] or ] or their salts;<ref name=j2>{{cite journal|last1=Swern|first1=Daniel|title=Organic Peracids.|journal=Chemical Reviews|volume=45|pages=1–68|year=1949|doi=10.1021/cr60140a001|quote=In the absence of catalysts, performic acid explodes when heated rapidly to 80–85°C.}}</ref><ref>{{cite journal|doi=10.1021/ja01201a016|last1=English|first1=James|year=1947|pages=2120|volume=69|journal=Journal of the American Chemical Society|last2=Gregory|first2=J. Delafield|title=Performic Acid Hydroxylation of a,p-Unsaturated Acids and Esters}}</ref> it can also be an organic compound containing at least one ] group, such as ] ]<ref>Matilla, T. and Aksela, R. 2000 Method for the Preparation of Aqueous Solutions Containing Performic Acid as Well as Their Use. {{US Patent|6049002}}, Issue date: April 11, 2000</ref> or peracetic acid.<ref name=pat2>Preuss, A., Fuchs, R., Huss, M. & Schneider, R. 2001 Aqueous Disinfecting Agent Containing Performic Acid and Peracetic Acid Process for Production and Process for Use Thereof {{US Patent|6211237}}, Issue date: April 3, 2001</ref>


==Safety== ==Safety==
Performic acid is non-toxic; it does irritate the skin, but less so than peracetic acid. Concentrated acid (above 50%) is highly reactive; it readily decomposes upon heating, and explodes upon rapid heating to 80–85 °C. It may ignite or explode at room temperature when combined with flammable substances, such as ], ], or ], and explodes violently upon addition of metal powders.<ref name=j2/> For this reason, spilled performic acid is diluted with cold water and collected with neutral, non-flammable inorganic absorbents, such as ].<ref name=b1/> Performic acid is non-toxic; it does irritate the skin, but less so than peracetic acid. Concentrated acid (above 50%) is highly reactive; it readily decomposes upon heating, and explodes upon rapid heating to 80–85&nbsp;°C. It may ignite or explode at room temperature when combined with flammable substances, such as ], ], or ], and explodes violently upon addition of metal powders.<ref name=j2/> For this reason, spilled performic acid is diluted with cold water and collected with neutral, non-flammable inorganic absorbents, such as ].<ref name=b1/>


==References== ==References==
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