Acetic acid

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; Ethylic acid[1][2]
Identifiers
3D model (JSmol)
3DMet
Abbreviations AcOH
506007
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.528 Edit this at Wikidata
EC Number
  • 200-580-7
E number E260 (preservatives)
1380
KEGG
MeSH Acetic+acid
RTECS number
  • AF1225000
UNII
UN number 2789
  • InChI=1S/C2H4O2/c1-2(3)4/h1H3,(H,3,4) checkY
    Key: QTBSBXVTEAMEQO-UHFFFAOYSA-N checkY
  • CC(O)=O
Properties
CH3COOH
Molar mass 60.052 g·mol−1
Appearance Colourless liquid
Odor Heavily vinegar-like
Density 1.049 g/cm3 (liquid); 1.27 g/cm3 (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]
Vapor pressure 1.54653947 kPa (20 °C)
11.6 mmHg (20 °C)[5]
Acidity (pKa) 4.756
Conjugate base Acetate
-31.54·10−6 cm3/mol
1.371 (VD = 18.19)
Viscosity 1.22 mPa s
1.22 cP
1.74 D
Thermochemistry
123.1 J K−1 mol−1
158.0 J K−1 mol−1
-483.88–483.16 kJ/mol
-875.50–874.82 kJ/mol
Pharmacology
G01AD02 (WHO) S02AA10 (WHO)
Legal status
  • AU: S2 (Pharmacy medicine) and S6
Hazards
GHS labelling:
GHS02: Flammable GHS05: Corrosive
Danger
H226, H314
P280, P305+P351+P338, P310
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
2
0
Flash point 40 °C (104 °F; 313 K)
427 °C (801 °F; 700 K)
Explosive limits 4–16%
Lethal dose or concentration (LD, LC):
3.31 g kg−1, oral (rat)
5620 ppm (mouse, 1 hr)
16000 ppm (rat, 4 hr)[7]
NIOSH (US health exposure limits):
PEL (Permissible)
TWA 10 ppm (25 mg/m3)[6]
REL (Recommended)
TWA 10 ppm (25 mg/m3) ST 15 ppm (37 mg/m3)[6]
IDLH (Immediate danger)
50 ppm[6]
Related compounds
Formic acid
Propionic acid
Related compounds
Acetaldehyde
Acetamide
Acetic anhydride
Chloroacetic acid
Acetyl chloride
Glycolic acid
Ethyl acetate
Potassium acetate
Sodium acetate
Thioacetic acid
Supplementary data page
Acetic acid (data page)
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 ?)
Acetic acid
Clinical data
AHFS/Drugs.comMonograph
Identifiers
E numberE260 (preservatives) Edit this at Wikidata
CompTox Dashboard (EPA)
ECHA InfoCard100.000.528 Edit this at Wikidata
Data page
Acetic acid (data page)

Acetic acid /əˈstɪk/, systematically named ethanoic acid /ˌɛθəˈnɪk/, is an acidic, colourless liquid and organic compound with the chemical formula CH3COOH (also written as CH3CO2H, C2H4O2, or HC2H3O2). Vinegar is at least 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water. It has been used, as a component of vinegar, throughout history from at least the third century BC.

Acetic acid is the second simplest carboxylic acid (after formic acid). It is an important chemical reagent and industrial chemical across various fields, used primarily in the production of cellulose acetate for photographic film, polyvinyl acetate for wood glue, and synthetic fibres and fabrics. In households, diluted acetic acid is often used in descaling agents. In the food industry, acetic acid is controlled by the food additive code E260 as an acidity regulator and as a condiment. In biochemistry, the acetyl group, derived from acetic acid, is fundamental to all forms of life. When bound to coenzyme A, it is central to the metabolism of carbohydrates and fats.

The global demand for acetic acid is about 6.5 million metric tonnes per year (t/a), manufactured from methanol.[8] Its production and subsequent industrial use poses health hazards to workers, including incidental skin damage and chronic respiratory injuries from inhalation.[9]

  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:10.1039/9781849733069-00648. ISBN 978-0-85404-182-4.
  4. ^ "acetic acid_msds".
  5. ^ Lange's Handbook of Chemistry, 10th ed.
  6. ^ a b c NIOSH Pocket Guide to Chemical Hazards. "#0002". National Institute for Occupational Safety and Health (NIOSH).
  7. ^ "Acetic acid". Immediately Dangerous to Life or Health Concentrations (IDLH). National Institute for Occupational Safety and Health (NIOSH).
  8. ^ Cite error: The named reference Ullmann was invoked but never defined (see the help page).
  9. ^ Cite error: The named reference :0 was invoked but never defined (see the help page).