| Revision as of 11:46, 5 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 451274826 of page Peracetic_acid for the Chem/Drugbox validation project (updated: ''). |
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{{Chembox |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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|Watchedfields = changed |
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{{chembox |
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|verifiedrevid = 464198630 |
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| Watchedfields = changed |
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|Name = Peracetic acid |
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| verifiedrevid = 408792505 |
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|ImageFileL1_Ref = {{chemboximage|correct|??}} |
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| Name = Peracetic acid |
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|ImageFileL1 = Ethaneperoxoic acid 200.svg |
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| ImageFileL1_Ref = {{chemboximage|correct|??}} |
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| ImageFileL1 = Peracetic acid.png |
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|ImageNameL1 = Peroxyacetic acid |
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|ImageFileR1 = Peracetic-acid-3D-balls.png |
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| ImageSizeL1 = 100px |
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| ImageNameL1 = Peroxyacetic acid |
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|ImageNameR1 = Peroxyacetic acid |
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|PIN = Ethaneperoxoic 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> |
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| ImageFileR1 = Peracetic-acid-3D-balls.png |
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| ImageNameR1 = Peroxyacetic acid |
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|OtherNames = Peroxyacetic acid<br/>Acetic peroxide<br/>Acetyl hydroperoxide<br/>Proxitane |
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|Section1={{Chembox Identifiers |
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| ImageSizeR1 = 120px |
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|Abbreviations = PAA |
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| IUPACName = Ethaneperoxoic acid |
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|SMILES = CC(=O)OO |
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| OtherNames = Peroxyacetic acid<br>Acetic peroxide<br>Acetyl hydroperoxide<br>Proxitane |
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|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| Section1 = {{Chembox Identifiers |
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|ChemSpiderID = 6336 |
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| Abbreviations = PAA |
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|ChEBI = 42530 |
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| SMILES = CC(=O)OO |
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|PubChem = 6585 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|EINECS = 201-186-8 |
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| ChemSpiderID = 6336 |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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| PubChem = 6585 |
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|UNII = I6KPI2E1HD |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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|KEGG_Ref = {{keggcite|correct|kegg}} |
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| UNII = I6KPI2E1HD |
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|KEGG = D03467 |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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|InChI = 1/C2H4O3/c1-2(3)5-4/h4H,1H3 |
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| KEGG = D03467 |
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|InChIKey = KFSLWBXXFJQRDL-UHFFFAOYAD |
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| InChI = 1/C2H4O3/c1-2(3)5-4/h4H,1H3 |
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|ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| InChIKey = KFSLWBXXFJQRDL-UHFFFAOYAD |
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|ChEMBL = 444965 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| ChEMBL = 444965 |
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|StdInChI = 1S/C2H4O3/c1-2(3)5-4/h4H,1H3 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C2H4O3/c1-2(3)5-4/h4H,1H3 |
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|StdInChIKey = KFSLWBXXFJQRDL-UHFFFAOYSA-N |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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|CASNo = 79-21-0 |
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| StdInChIKey = KFSLWBXXFJQRDL-UHFFFAOYSA-N |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 79-21-0 |
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|RTECS = SD8750000 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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|UNNumber = 3107 3105 |
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| RTECS = SD8750000 |
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}} |
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| Section2 = {{Chembox Properties |
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| Formula = C<sub>2</sub>H<sub>4</sub>O<sub>3</sub> |
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| MolarMass = 76.05 |
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| Appearance = Colorless liquid |
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| Density = 1.0375 g/mL<ref name=u1/> |
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| SolubilityOther = |
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| Solvent = solvent |
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| MeltingPt = 0 °C<ref name=u1/> |
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| BoilingPt = 25 °C (1.6 kPa)<ref name=u1/> |
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| pKa = 8.2<ref name=u1>Elvers, B. ''et al.'' (ed.) Ullmann's Encyclopedia of Industrial Chemistry, 5th ed. Vol. A19, Wiley, p. 206</ref> |
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| Viscosity = 3.280 ]|25 |
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| RefractIndex = 1.3974 (589 nm, 20 °C)<ref name=u1/> |
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}} |
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| Section7 = {{Chembox Hazards |
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| EUClass = Oxidant ('''O''')<br />Corrosive ('''C''')<br />Dangerous for the environment ('''N''') |
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| NFPA-H = 3 |
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| NFPA-F = 2 |
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| NFPA-R = 2 |
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| NFPA-O = OX |
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| RPhrases = {{R8}} {{R5}} {{R11}} {{R25}} {{R34}} |
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| SPhrases = {{S1/2}} {{S3/7}} {{S14}} {{S36/37/39}} {{S45}} {{S61}} |
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| FlashPt = 40.5 °C |
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}} |
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}} |
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}} |
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|Section2={{Chembox Properties |
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|Formula = CH<sub>3</sub>CO<sub>3</sub>H |
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|MolarMass = 76.05 g/mol |
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|Appearance = Colorless liquid |
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|Density = 1.0375 g/mL |
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|Solvent = solvent |
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|MeltingPtC = 0 |
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|MeltingPt_ref = <ref name=Ullmann/> |
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|BoilingPtC = 105 |
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|BoilingPt_notes = 25 C @ (1.6 kPa)<ref name=Ullmann/> |
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|pKa = 8.2 |
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|Viscosity = 3.280 ] |
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|RefractIndex = 1.3974 (589 nm, 20 °C)<ref name=Ullmann/> |
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}} |
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|Section3={{Chembox Pharmacology |
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|ATCvet = yes |
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|ATCCode_prefix = G51 |
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|ATCCode_suffix = AD03 |
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}} |
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|Section4={{Chembox Hazards |
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|GHSPictograms = {{GHS02}}{{GHS05}}{{GHS07}}{{GHS09}} |
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|GHSSignalWord = Danger |
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|HPhrases = {{H-phrases|226|242|302|312|314|332|400}} |
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|PPhrases = {{P-phrases|210|220|233|234|240|241|242|243|260|261|264|270|271|273|280|301+312|301+330+331|302+352|303+361+353|304+312|304+340|305+351+338|310|312|321|322|330|363|370+378|391|403+235|405|411|420|501}} |
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|NFPA-H = 3 |
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|NFPA-F = 2 |
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|NFPA-R = 2 |
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|NFPA-S = OX |
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|FlashPtC = 40.5 |
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}} |
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}} |
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'''Peracetic acid''' (also known as '''peroxyacetic acid''', or '''PAA''') is an ] with the ] CH<sub>3</sub>CO<sub>3</sub>H. This ] is a colorless liquid with a characteristic acrid odor reminiscent of ]. It can be highly ]. |
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Peracetic acid is a weaker acid than the parent acetic acid, with a ] of 8.2.<ref name=Ullmann/> |
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==Production== |
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Peracetic acid is produced industrially by the ] of ]:<ref name=Ullmann>{{Ullmann |first1= Herbert|last1= Klenk|first2= Peter H.|last2= Götz|first3= Rainer|last3= Siegmeier|first4= Wilfried|last4= Mayr |title= Peroxy Compounds, Organic |doi= 10.1002/14356007.a19_199}}</ref> |
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:O<sub>2</sub> + CH<sub>3</sub>CHO → CH<sub>3</sub>CO<sub>3</sub>H |
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In the presence of a strong acid catalyst, such as sulfuric acid, ] and ] produce peracetic acid:<ref>{{cite journal|last1=Rangarajan |first1=B. |last2=Havey|first2= A.|last3= Grulke|first3= E. |last4=Culnan|first4= P. D. |year=1995|title=Kinetic parameters of a two-phase model for ''in situ'' epoxidation of soybean oil |journal=]|volume=72|issue=10 |pages=1161–1169 |doi=10.1007/bf02540983|s2cid=98196947}}</ref> |
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:H<sub>2</sub>O<sub>2</sub> + CH<sub>3</sub>CO<sub>2</sub>H {{eqm}} CH<sub>3</sub>CO<sub>3</sub>H + H<sub>2</sub>O |
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However, in concentrations (3-6%) of vinegar and hydrogen peroxide marketed for household use, mixing without a strong acid catalyst will not form peracetic acid. |
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As an alternative, ] and ] can be used to generate a solution of the acid with lower water content. |
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Peracetic acid is generated '']'' by some ]s. This is achieved by the action of ]s, such as ] and ], upon hydrogen peroxide formed from ] in water. The peracetic acid is a more effective ] than hydrogen peroxide itself.<ref name="Smuldersvon Rybinski2007">{{Ullmann|last1=Smulders|first1=Eduard|last2=Von Rybinski|first2=Wolfgang|last3=Sung|first3=Eric|last4=Rähse|first4=Wilfried|last5=Steber|first5=Josef|last6=Wiebel|first6=Frederike|last7=Nordskog|first7=Anette|title=Laundry Detergents|year=2007|doi=10.1002/14356007.a08_315.pub2}}</ref><ref name=AMS>{{cite web|publisher=United States Department of Agriculture|website= Agriculture Marketing Service |url=http://www.ams.usda.gov/nop/NationalList/TAPReviews/PeraceticAcid2.pdf |title=Peracetic acid |access-date=2006-11-11}}</ref> PAA is also formed naturally in the environment through a series of ]s involving ] and photo-oxidant ]s.<ref name=USLib>{{cite web|publisher=U.S. National Library of Medicine|website=ToxNet|url=http://toxnet.nlm.nih.gov/cgi-bin/sis/htmlgen?hsdbb.htm |title=Hazardous Substances Data Bank|access-date=2006-11-11}}</ref> |
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Peracetic acid is always sold in solution as a mixture with acetic acid and hydrogen peroxide to maintain its stability. The concentration of the acid as the active ingredient can vary. |
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==Uses== |
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The ] first registered peracetic acid as an ] in 1986 for indoor use on hard surfaces. Use sites include agricultural premises, food establishments, medical facilities, and home bathrooms. Peracetic acid is also registered for use in dairy and cheese processing plants, on food processing equipment, and in pasteurizers in breweries, wineries, and beverage plants.<ref name=USEPA>{{cite web|publisher=U.S. Environmental Protection Agency|url=http://www.epa.gov/pesticides/factsheets/chemicals/hydrogenperoxide_peroxyaceticacid_factsheet.htm|title=Hydrogen Peroxide and Peroxyacetic Acid|access-date=2006-11-11}}</ref> It is also applied for the disinfection of medical supplies, to prevent biofilm formation in pulp industries, and as a water purifier and disinfectant. Peracetic acid can be used as a ] water disinfectant, where it prevents biofilm formation and effectively controls '']'' bacteria. Nu-Cidex is the ] for a brand of antimicrobial peracetic acid.<ref>{{Cite journal |
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| last1= Lynam |first1= P. A. |
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| last2= Babb |first2= J. R. |
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| last3= Fraise |first3= A. P. |
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| title= Comparison of the mycobactericidal activity of 2% alkaline glutaraldehyde and 'Nu-Cidex' (0.35% peracetic acid) |
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| journal= ] |
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| volume= 30 |
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| issue= 3 |
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| pages= 237–240 |
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| year= 1995 |
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| pmid= 8522783 |
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| doi=10.1016/s0195-6701(95)90322-4 |
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}}</ref> |
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In the European Union, peroxyacetic acid was reported by the EFSA after submission in 2013 by the US Department of Agriculture.<ref>{{Cite web|url=https://www.betelgeux.es/en/news/efsa-peroxyacetic-acid-poultry/|title = EFSA publishes a favourable opinion on the use of peroxyacetic acid on poultry}}</ref> |
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Decontamination kits for cleaning ] analogues from surfaces (as used by many police forces, amongst others) often contain solid ], which mixes with water to produce peracetic acid.<ref>{{cite web |title=First Line Technologies' Dahlgren Decon' |url=https://www.cbrnetechindex.com/Print/4605/first-line-technology-llc/dahlgren-decon |website=CBRNE Tech |access-date=19 August 2020}}</ref> |
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===Epoxidation=== |
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Although less active than more acidic peracids (e.g., ]), peracetic acid in various forms is used for the ] of various ]s (]). Useful applications are for unsaturated fats, synthetic and natural rubbers, and some natural products such as ]. A variety of factors affect the amount of free acid or sulfuric acid (used to prepare the peracid).<ref name="SienelRieth2000">{{Ullmann|last1=Sienel|first1=Guenter|last2=Rieth|first2=Robert|last3=Rowbottom|first3=Kenneth T.|title=Epoxides|year=2000|doi=10.1002/14356007.a09_531}}</ref> |
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==Safety== |
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Peracetic acid is a strong ] and severe irritant to the skin, eyes, and respiratory system. The U.S. ] published the following ] (AEGL):<ref>{{cite web| url=https://www.epa.gov/aegl/peracetic-acid-results-aegl-program| title=Peracetic Acid Results - AEGL Program| date=29 September 2014| publisher=US EPA}}</ref> |
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{| class="wikitable sortable" |
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!eight-hour TWA AEGL |
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!Definition |
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!mg/m<sup>3</sup> |
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!ppm |
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|- |
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| 1 |
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| The concentration at which the general population will experience transient and reversible problems, such as notable discomfort, irritation, or certain asymptomatic non-sensory effects. |
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| 0.52 |
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| 0.17 |
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|- |
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| 2 |
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| The concentration that results in irreversible or other serious, long-lasting adverse health effects or an impaired ability to escape. |
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| 1.6 |
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| 0.52 |
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|- |
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| 3 |
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| The concentration that results in life-threatening health effects or death. |
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| 4.1 |
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| 1.3 |
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==See also== |
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==References== |
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{{Reflist|30em}} |
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{{Authority control}} |
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