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Acetic acid information


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
CAS Number
  • 64-19-7 checkY
3D model (JSmol)
  • Interactive image
3DMet
  • B00009
Abbreviations AcOH
Beilstein Reference
506007
ChEBI
  • CHEBI:15366 checkY
ChEMBL
  • ChEMBL539 checkY
ChemSpider
  • 171 checkY
DrugBank
  • DB03166 checkY
ECHA InfoCard 100.000.528 Edit this at Wikidata
EC Number
  • 200-580-7
E number E260 (preservatives)
Gmelin Reference
1380
IUPHAR/BPS
  • 1058
KEGG
  • C00033
  • D00010 checkY
MeSH Acetic+acid
PubChem CID
  • 176
RTECS number
  • AF1225000
UNII
  • Q40Q9N063P checkY
UN number 2789
CompTox Dashboard (EPA)
  • DTXSID5024394 Edit this at Wikidata
InChI
  • InChI=1S/C2H4O2/c1-2(3)4/h1H3,(H,3,4) checkY
    Key: QTBSBXVTEAMEQO-UHFFFAOYSA-N checkY
SMILES
  • CC(O)=O
Properties
Chemical formula
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
Solubility in water
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
Magnetic susceptibility (χ)
-31.54·10−6 cm3/mol
Refractive index (nD)
1.371 (VD = 18.19)
Viscosity 1.22 mPa s
1.22 cP
Dipole moment
1.74 D
Thermochemistry
Heat capacity (C)
123.1 J K−1 mol−1
Std molar
entropy (S298)
158.0 J K−1 mol−1
Std enthalpy of
formation fH298)
-483.88–483.16 kJ/mol
Std enthalpy of
combustion cH298)
-875.50–874.82 kJ/mol
Pharmacology
ATC code
G01AD02 (WHO) S02AA10 (WHO)
Legal status
  • AU: S2 (Pharmacy medicine) and S6
Hazards
GHS labelling:
Pictograms
GHS02: Flammable GHS05: Corrosive
Signal word
Danger
Hazard statements
H226, H314
Precautionary statements
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)
Autoignition
temperature
427 °C (801 °F; 700 K)
Explosive limits 4–16%
Lethal dose or concentration (LD, LC):
LD50 (median dose)
3.31 g kg−1, oral (rat)
LC50 (median concentration)
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
Related carboxylic acids
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 ?)
Infobox references
Acetic acid
Clinical data
AHFS/Drugs.comMonograph
Identifiers
E numberE260 (preservatives) Edit this at Wikidata
CompTox Dashboard (EPA)
  • DTXSID5024394 Edit this at Wikidata
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).

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Acetic acid

Last Update:

Acetic acid /əˈsiːtɪk/, systematically named ethanoic acid /ˌɛθəˈnoʊɪk/, is an acidic, colourless liquid and organic compound with the chemical formula...

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Acetic anhydride

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of a carboxylic acid and is widely used as a reagent in organic synthesis. It is a colorless liquid that smells strongly of acetic acid, which is formed...

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Acetic acid bacteria

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Acetic acid bacteria (AAB) are a group of Gram-negative bacteria which oxidize sugars or ethanol and produce acetic acid during fermentation. The acetic...

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Ethyl acetate

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process of tea and coffee. Ethyl acetate is the ester of ethanol and acetic acid; it is manufactured on a large scale for use as a solvent. Ethyl acetate...

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Peracetic acid

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reminiscent of acetic acid. It can be highly corrosive. Peracetic acid is a weaker acid than the parent acetic acid, with a pKa of 8.2. Peracetic acid is produced...

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Acetaldehyde

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acetaldehyde was mainly used as a precursor to acetic acid. This application has declined because acetic acid is produced more efficiently from methanol by...

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Vinegar

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of acetic acid and trace compounds that may include flavorings. Vinegar typically contains from 5% to 18% acetic acid by volume. Usually, the acetic acid...

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Formic acid

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temperature, comparable to the related acetic acid. Formic acid is about ten times stronger than acetic acid. It is miscible with water and most polar...

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Methyl acetate

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Methyl acetate, also known as MeOAc, acetic acid methyl ester or methyl ethanoate, is a carboxylate ester with the formula CH3COOCH3. It is a flammable...

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Propionic acid

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Propionic acid has physical properties intermediate between those of the smaller carboxylic acids, formic and acetic acids, and the larger fatty acids. It is...

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Acid

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digestive enzymes), acetic acid (vinegar is a dilute aqueous solution of this liquid), sulfuric acid (used in car batteries), and citric acid (found in citrus...

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Carboxylic acid

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-ic acid and -ate for a conjugate acid and its conjugate base, respectively. For example, the conjugate base of acetic acid is acetate. Carbonic acid, which...

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Monsanto process

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The Monsanto process is an industrial method for the manufacture of acetic acid by catalytic carbonylation of methanol. The Monsanto process has largely...

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Ester

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oxoacids (e.g. esters of acetic acid, carbonic acid, sulfuric acid, phosphoric acid, nitric acid, xanthic acid), but also from acids that do not contain oxygen...

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Glycine

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French chemist Auguste Cahours determined that glycine was an amine of acetic acid. Although glycine can be isolated from hydrolyzed protein, this route...

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Acid dissociation constant

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a simple example for a weak acid with Ka = 10−5, log Ka is the exponent which is -5, so that pKa = 5. And for acetic acid with Ka = 1.8 x 10−5, pKa is...

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Acetate

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An acetate is a salt formed by the combination of acetic acid with a base (e.g. alkaline, earthy, metallic, nonmetallic or radical base). "Acetate" also...

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Lactic acid

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3CH(OH)CO− 2. Compared to acetic acid, its pKa is 1 unit less, meaning lactic acid is ten times more acidic than acetic acid. This higher acidity is the...

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Trifluoroacetic acid

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colorless liquid with a vinegar-like odor. TFA is a stronger acid than acetic acid, having an acid ionisation constant, Ka, that is approximately 34,000 times...

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Vinyl acetate

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esters. The major industrial route involves the reaction of ethylene and acetic acid with oxygen in the presence of a palladium catalyst. 2 C 2 H 4 + 2 CH...

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Acetobacter aceti

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Louis Pasteur proved it to be the cause of conversion of ethanol to acetic acid in 1864. Its bacterial motility plays an important role in the formation...

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Kombucha

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to acetic acid (and other acids). Although the SCOBY is commonly called "tea fungus" or "mushroom", it is actually "a symbiotic growth of acetic acid bacteria...

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Acetamide

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is an organic compound with the formula CH3CONH2. It is derived from acetic acid. It finds some use as a plasticizer and as an industrial solvent. The...

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Acid strength

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A-}}} Acetic acid (CH3COOH{\displaystyle {\ce {CH3COOH}}}) is an example of a weak acid. The strength of a weak acid is quantified by its acid dissociation...

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Methanol

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as a precursor to other commodity chemicals, including formaldehyde, acetic acid, methyl tert-butyl ether, methyl benzoate, anisole, peroxyacids, as well...

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