Editing Acetic anhydride (section)

{{short description|Organic compound with formula (CH₃CO)₂O}}
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| verifiedrevid = 477238827
| Name = Acetic anhydride
| ImageFile = Acetic_anhydride2DACS.svg
| ImageClass = skin-invert
| ImageSize = 150px
| ImageName = Acetic anhydride
| ImageFile1 = Acetic-anhydride-from-xtal-2003-3D-balls.png
| ImageClass1 = bg-transparent 
| ImageSize1 = 150px
| ImageName1 = Acetic anhydride
| PIN = Acetic anhydride <!-- Nomenclature of Organic Chemistry – IUPAC Recommendations and Preferred Names 2013 (Blue Book) -->
| SystematicName = Ethanoic anhydride
| OtherNames = Ethanoyl ethanoate<br />Acetic acid anhydride<br />Acetyl acetate<br />Acetyl oxide<br />Acetic oxide
|Section1={{Chembox Identifiers
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 36610
| SMILES = O=C(OC(=O)C)C
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 2E48G1QI9Q
| InChIKey = WFDIJRYMOXRFFG-UHFFFAOYAH
| SMILES1 = CC(=O)OC(=O)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C4H6O3/c1-3(5)7-4(2)6/h1-2H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = WFDIJRYMOXRFFG-UHFFFAOYSA-N
| CASNo = 108-24-7
| CASNo_Ref = {{cascite|correct|CAS}}
| PubChem = 7918
| EINECS = 203-564-8
| RTECS = AK1925000
| UNNumber = 1715
| ChEMBL = 1305819
| InChI = 1/C4H6O3/c1-3(5)7-4(2)6/h1-2H3
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 7630
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|Section2={{Chembox Properties
| C=4 | H=6 | O=3
| Appearance = colorless liquid
| Density = 1.082 g cm<sup>−3</sup>, liquid
| Solubility = 2.6 g/100 mL, reacts (''see text'')
| MeltingPtC = −73.1
| BoilingPtC = 139.8
| RefractIndex = 1.3901
| VaporPressure = 4 mmHg (20&nbsp;°C)<ref name=NIOSH/>
| MagSus = −52.8·10<sup>−6</sup> cm<sup>3</sup>/mol
 }}
| Section4 = {{Chembox Thermochemistry
| Thermochemistry_ref = <ref name="crc">{{cite book |author1=John Rumble |title=CRC Handbook of Chemistry and Physics |date=June 18, 2018 |publisher=CRC Press |isbn=978-1138561632 |pages=5–3 |edition=99th |language=en}}</ref>
| HeatCapacity = 
| Entropy =
| DeltaHform = −624.4&nbsp;kJ/mol
| DeltaGfree = 
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| LHV =
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| Section6 = {{Chembox Pharmacology
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| Legal_status = 
| Legal_AU = S6
| Legal_AU_comment = 
| Legal_CA = Schedule VI
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|Section7={{Chembox Hazards
| ExternalSDS = [http://www.inchem.org/documents/icsc/icsc/eics0209.htm ICSC 0209]
| GHSPictograms = {{GHS02}}{{GHS05}}{{GHS07}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|226|302|314|330}}
| PPhrases = {{P-phrases|210|233|240|241|242|243|260|261|264|270|271|280|301+312|301+330+331|303+361+353|304+312|304+340|305+351+338|310|312|321|330|363|370+378|403+235|405|501}}
| NFPA-H = 3
| NFPA-F = 2
| NFPA-R = 1
| NFPA-S = W
| FlashPtC = 49
| AutoignitionPtC = 316
| ExploLimits = 2.7–10.3%
| PEL = TWA 5 ppm (20&nbsp;mg/m<sup>3</sup>)<ref name=NIOSH>{{PGCH|0003}}</ref>
| REL = C 5 ppm (20&nbsp;mg/m<sup>3</sup>)<ref name=NIOSH/>
| IDLH = 200 ppm<ref name=NIOSH/> 
| LC50 = 1000 ppm (rat, 4&nbsp;[[hour|h]])<ref>{{IDLH|108247|Acetic anhydride}}</ref>
 }}
|Section8={{Chembox Related
| OtherFunction_label = [[acid anhydride]]s
| OtherFunction = [[Propionic anhydride]]
| OtherCompounds = [[Acetic acid]]<br />[[Acetyl chloride]]
 }}
}}

'''Acetic anhydride''', or '''ethanoic anhydride''', is the [[chemical compound]] with the [[chemical formula|formula]] {{chem2|(CH3CO)2O}}. Commonly abbreviated {{chem2|[[Acetyl|Ac]]2O}}, it is one the simplest [[organic acid anhydride|anhydride]]s of a [[carboxylic acid]] and is widely used in the production of [[cellulose acetate]] as well as a [[reagent]] in [[organic synthesis]]. It is a colorless liquid that smells strongly of [[acetic acid]], which is formed by its reaction with moisture in the air.