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{{Chembox
[[File:Acetic-acid-3D-balls.png|thumb|[[Schematic]] picture of acetic acid molecule.]]
| Verifiedfields = changed
'''Acetic acid''' or '''ethanoic acid''' (CH<sub>3</sub>COOH) is a kind of [[carboxylic acid]], which is often called [[vinegar]]. It [[taste]]s and [[Odor|smells]] [[sour]]. Its [[melting point]] is 16.5&nbsp;°C(61.6&nbsp;°F) and [[boiling point]] is 118.1&nbsp;°C(244.5&nbsp;°F).
| Watchedfields = changed
| verifiedrevid = 477238786
| Name =
| ImageFile =
| ImageFileL1 = Acetic-acid-2D-skeletal.svg
| ImageFileL1_Ref = {{chemboximage|correct|??}}
| ImageNameL1 = Skeletal formula of acetic acid
| ImageFileR1 = Acetic-acid-CRC-GED-3D-vdW-B.png
| ImageFileR1_Ref = {{chemboximage|correct|??}}
| ImageNameR1 = Spacefill model of acetic acid
| ImageFileL2 = Essigsäure - Acetic acid.svg
| ImageFileL2_Ref = {{chemboximage|correct|??}}
| ImageNameL2 = Skeletal formula of acetic acid with all explicit hydrogens added
| ImageFileR2 = Acetic-acid-CRC-GED-3D-balls-B.png
| ImageFileR2_Ref = {{chemboximage|correct|??}}
| ImageNameR2 = Ball and stick model of acetic acid
| ImageFile3 = Acetic acid.jpg
| ImageFile3_Ref = {{chemboximage|correct|??}}
| ImageSize3 = 244
| ImageName3 = Sample of acetic acid in a reagent bottle
| PIN = Acetic acid<ref name=iupac2013>{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = [[Royal Society of Chemistry|The Royal Society of Chemistry]] | date = 2014 | location = Cambridge | page = 745 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4}}</ref>
| SystematicName = Ethanoic acid
| OtherNames = Vinegar (when dilute); Hydrogen acetate; Methanecarboxylic acid<ref>{{cite book|title=Scientific literature reviews on generally recognised as safe (GRAS) food ingredients|publisher=National Technical Information Service|year=1974|page=1}}</ref><ref>"Chemistry", volume 5, Encyclopædia Britannica, 1961, page 374</ref>
| IUPACName =
| Section1 = {{Chembox Identifiers
| Abbreviations = AcOH
| CASNo = 64-19-7
| CASNo_Ref = {{cascite|correct|CAS}}
| PubChem = 176
| ChemSpiderID = 171
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| UNII = Q40Q9N063P
| UNII_Ref = {{fdacite|correct|FDA}}
| EINECS = 200-580-7
| UNNumber = 2789
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB03166
| KEGG = D00010
| KEGG_Ref = {{keggcite|changed|kegg}}
| MeSHName = Acetic+acid
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 15366
| ChEMBL = 539
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| IUPHAR_ligand = 1058
| Beilstein = 506007
| Gmelin = 1380
| 3DMet = B00009
| RTECS = AF1225000
| SMILES = CC(O)=O
| StdInChI = 1S/C2H4O2/c1-2(3)4/h1H3,(H,3,4)
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = QTBSBXVTEAMEQO-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
}}
| Section2 = {{Chembox Properties
| C=2 | H=4 | O=2
| Appearance = Colourless liquid
| Odor = Pungent/Vinegar-like


| Density = 1.049 g cm<sup>−3</sup> (liquid); 1.27 g cm cm<sup>−3</sup> (solid)
{{chem-stub}}
| Solubility = [[Miscible]]
| MeltingPtK = 289 to 290
| BoilingPtK = 391 to 392
| pKa = {{ubl
| 4.756 (H<sub>2</sub>O)<ref name="CRC97">{{cite book | editor= Haynes, William M. | year = 2016 | title = CRC Handbook of Chemistry and Physics | edition = 97th | publisher = [[CRC Press]] | isbn = 9781498754293 | pages=5–88 | title-link = CRC Handbook of Chemistry and Physics }}</ref>
| 12.6 (DMSO)<ref>{{cite journal |last1=Bordwell |first1=F. G. |last2=Algrim |first2=Donald |title=Nitrogen acids. 1. Carboxamides and sulfonamides |journal=The Journal of Organic Chemistry |date=1976 |volume=41 |issue=14 |pages=2507–2508 |doi=10.1021/jo00876a042}}</ref>
}}
| pKb = 9.24 (basicity of acetate ion)
| ConjugateBase = [[Acetate]]
| Viscosity = 1.22 mPa s
| RefractIndex = 1.371
| Dipole = 1.74 D
| MagSus = -31.54·10<sup>−6</sup> cm<sup>3</sup>/mol
| LogP = -0.28<ref name="chemsrc">{{Cite web|url=https://www.chemsrc.com/en/cas/64-19-7_162032.html|title=acetic acid_msds}}</ref>
}}
| Section3 =
| Section4 =
| Section5 = {{Chembox Thermochemistry
| DeltaHf = -483.88—483.16 kJ mol<sup>−1</sup>
| DeltaHc = -875.50—874.82 kJ mol<sup>−1</sup>
| Entropy = 158.0 J K<sup>−1</sup> mol<sup>−1</sup>
| HeatCapacity = 123.1 J K<sup>−1</sup> mol<sup>−1</sup>
}}
| Section6 = {{Chembox Pharmacology
| ATCCode_prefix = G01
| ATCCode_suffix = AD02
| ATC_Supplemental = {{ATC|S02|AA10}}
}}
| Section7 = {{Chembox Hazards
| GHSPictograms = {{GHS02}} {{GHS05}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|226|314}}
| PPhrases = {{P-phrases|280|305+351+338|310}}
| NFPA-F = 2
| NFPA-H = 3
| NFPA-R = 0
| FlashPtC = 40
| AutoignitionPtC = 427
| LD50 = 3.31 g kg<sup>−1</sup>, oral (rat)
| LC50 = 5620 ppm (mouse, 1 hr)<br />16000 ppm (rat, 4 hr)<ref>{{IDLH|64197|Acetic acid}}</ref>
| ExploLimits = 4–16%
| PEL = TWA 10 ppm (25 mg/m<sup>3</sup>)<ref name=PGCH>{{PGCH|0002}}</ref>
| REL = TWA 10 ppm (25 mg/m<sup>3</sup>) ST 15 ppm (37 mg/m<sup>3</sup>)<ref name=PGCH />
| IDLH = 50 ppm<ref name=PGCH />
}}
| Section8 = {{Chembox Related
| OtherFunction_label = [[carboxylic acid]]s
| OtherFunction = [[Formic acid]]<br />[[Propionic acid]]
| OtherCompounds = [[Acetaldehyde]]<br />
[[Acetamide]]<br />
[[Acetic anhydride]]<br />
[[Acetonitrile]]<br />
[[Acetyl chloride]]<br />
[[Ethanol]]<br />
[[Ethyl acetate]]<br />
[[Potassium acetate]]<br />
[[Sodium acetate]]<br />
[[Thioacetic acid]]
}}
}}
[[File:Essig-1.jpg|thumb|[[Vinegar]] contains acetic acid. [[Aceto balsamico]], vinegar from red and from white wine. ]]
'''Acetic acid''', or '''ethanoic acid''', (CH<sub>3</sub>COOH) is a [[carboxylic acid]]. It is the main compound of [[vinegar]], other than [[water]].


It [[taste]]s and [[Odor|smells]] [[sour]]; it has no [[color]]. Its [[melting point]] is 16.5&nbsp;°C(61.6&nbsp;°F) and its [[boiling point]] is 118.1&nbsp;°C(244.5&nbsp;°F). It has a [[pH]] of 2.4.
[[Category:acids]]


Acetic acid is commonly used as a [[food additive]]. It has the [[E number|E numbers]] E 260 (acetic acid).
{{Link FA|bg}}
{{Link FA|en}}
{{Link FA|ro}}
{{Link FA|zh}}


[[Potassium acetate]] (E 261), [[sodium acetate]] (E 262), and [[calcium acetate]] (E 2639) are [[Salt|salts]] of acetic acid; they are commonly used to [[Food preservation|preserve food]], usually [[Vegetable|vegetables]]. In [[sourdough]], [[ethanol fermentation]] is used.
{{Link FA|id}}

==References==
{{reflist}}

{{-}}
{{chem-stub}}


[[Category:Carboxylic acids|2]]
[[af:Asynsuur]]
[[Category:Acids]]
[[ar:حمض الخليك]]
[[az:Sirkə turşusu]]
[[bn:অ্যাসিটিক এসিড]]
[[be:Воцатная кіслата]]
[[bg:Оцетна киселина]]
[[bs:Acetatna kiselina]]
[[ca:Àcid acètic]]
[[cs:Kyselina octová]]
[[cy:Asid asetig]]
[[da:Eddikesyre]]
[[de:Essigsäure]]
[[et:Etaanhape]]
[[el:Αιθανικό οξύ]]
[[en:Acetic acid]]
[[es:Ácido acético]]
[[eo:Aceta acido]]
[[eu:Azido azetiko]]
[[fa:استیک اسید]]
[[fr:Acide acétique]]
[[ga:Aigéad aicéiteach]]
[[gl:Ácido acético]]
[[ko:아세트산]]
[[hi:एसिटिक अम्ल]]
[[hr:Octena kiselina]]
[[io:Acetat-acido]]
[[id:Asam asetat]]
[[ia:Acido acetic]]
[[it:Acido acetico]]
[[he:חומצה אצטית]]
[[jv:Asam asetat]]
[[kn:ಅಸಿಟಿಕ್ ಆಮ್ಲ]]
[[kk:Сірке қышқылы]]
[[la:Acidum aceticum]]
[[lv:Etiķskābe]]
[[lt:Acto rūgštis]]
[[hu:Ecetsav]]
[[mk:Оцетна киселина]]
[[ml:അസറ്റിക് അമ്ലം]]
[[ms:Asid asetik]]
[[nl:Azijnzuur]]
[[ja:酢酸]]
[[no:Eddiksyre]]
[[nn:Eddiksyre]]
[[pl:Kwas octowy]]
[[pt:Ácido etanoico]]
[[qu:Mama aqha p'uchqu]]
[[ru:Уксусная кислота]]
[[si:ඇසිටික් අම්ලය]]
[[sk:Kyselina octová]]
[[sl:Ocetna kislina]]
[[sr:Сирћетна киселина]]
[[sh:Sirćetna kiselina]]
[[su:Asam asétat]]
[[fi:Etikkahappo]]
[[sv:Ättiksyra]]
[[ta:அசிட்டிக் காடி]]
[[te:ఎసిటిక్ ఆమ్లం]]
[[th:กรดน้ำส้ม]]
[[tr:Asetik asit]]
[[uk:Оцтова кислота]]
[[vi:Axit axetic]]
[[zh-yue:醋酸]]
[[zh:乙酸]]

Latest revision as of 07:35, 19 March 2023

Acetic acid
Skeletal formula of acetic acid
Skeletal formula of acetic acid
Spacefill model of acetic acid
Spacefill model of acetic acid
Skeletal formula of acetic acid with all explicit hydrogens added
Skeletal formula of acetic acid with all explicit hydrogens added
Ball and stick model of acetic acid
Ball and stick model of acetic acid
Sample of acetic acid in a reagent bottle
Names
Preferred IUPAC name
Acetic acid[3]
Systematic IUPAC name
Ethanoic acid
Other names
Vinegar (when dilute); Hydrogen acetate; Methanecarboxylic acid[1][2]
Identifiers
3D model (JSmol)
3DMet
Abbreviations AcOH
Beilstein Reference 506007
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.528
EC Number
  • 200-580-7
E number E260 (preservatives)
Gmelin Reference 1380
KEGG
MeSH Acetic+acid
RTECS number
  • AF1225000
UNII
UN number 2789
  • CC(O)=O
Properties
C2H4O2
Molar mass 60.05 g·mol−1
Appearance Colourless liquid
Odor Pungent/Vinegar-like
Density 1.049 g cm−3 (liquid); 1.27 g cm cm−3 (solid)
Melting point 16 to 17 °C; 61 to 62 °F; 289 to 290 K
Boiling point 118 to 119 °C; 244 to 246 °F; 391 to 392 K
Miscible
log P -0.28[4]
Acidity (pKa)
Basicity (pKb) 9.24 (basicity of acetate ion)
Conjugate base Acetate
-31.54·10−6 cm3/mol
1.371
Viscosity 1.22 mPa s
1.74 D
Thermochemistry
Std enthalpy of
formation ΔfHo298 		-483.88—483.16 kJ mol−1
Std enthalpy of
combustion ΔcHo298 		-875.50—874.82 kJ mol−1
Standard molar
entropy So298 		158.0 J K−1 mol−1
Specific heat capacity, C 123.1 J K−1 mol−1
Pharmacology
G01AD02 (WHO) S02AA10 (WHO)
Hazards
NFPA 704

2
3
0
 
Explosive limits 4–16%
U.S. Permissible
exposure limit (PEL) 		TWA 10 ppm (25 mg/m3)[7]
Related compounds
Related {{{label}}} {{{value}}}
Related compounds {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references
Vinegar contains acetic acid. Aceto balsamico, vinegar from red and from white wine.

Acetic acid, or ethanoic acid, (CH3COOH) is a carboxylic acid. It is the main compound of vinegar, other than water.

It tastes and smells sour; it has no color. Its melting point is 16.5 °C(61.6 °F) and its boiling point is 118.1 °C(244.5 °F). It has a pH of 2.4.

Acetic acid is commonly used as a food additive. It has the E numbers E 260 (acetic acid).

Potassium acetate (E 261), sodium acetate (E 262), and calcium acetate (E 2639) are salts of acetic acid; they are commonly used to preserve food, usually vegetables. In sourdough, ethanol fermentation is used.

References

[change | change source]
  1. ↑ Scientific literature reviews on generally recognised as safe (GRAS) food ingredients. National Technical Information Service. 1974. p. 1.
  2. ↑ "Chemistry", volume 5, Encyclopædia Britannica, 1961, page 374
  3. ↑ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 745. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
  4. ↑ "acetic acid_msds".
  5. ↑ Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. pp. 5–88. ISBN 9781498754293.
  6. ↑ Bordwell, F. G.; Algrim, Donald (1976). "Nitrogen acids. 1. Carboxamides and sulfonamides". The Journal of Organic Chemistry. 41 (14): 2507–2508. doi:10.1021/jo00876a042.
  7. ↑ NIOSH Pocket Guide to Chemical Hazards. "#0002". National Institute for Occupational Safety and Health (NIOSH).
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