For other uses, see Acetate (disambiguation).

acetate anion

acetate ester

Acetate (pronounced /ˈæsɪteɪt/) is a derivative of acetic acid. Two types of derivatives are known,
salts and ester. Most of the approximately 5 billion kilograms of acetic acid produced annually in
industry are used in the production of acetates, which usually take the form of polymers. In
nature, acetate is the most common building block for biosynthesis. For example, the fatty acids
are produced by connecting C2 units derived from acetate.[1]

Contents
[hide]

 1 Nomenclature and presentation of formula

 2 Salts
o 2.1 Applications
 3 Esters
o 3.1 Applications
 4 Acetate in biology
 5 References
 6 Structures
 7 See also

[edit] Nomenclature and presentation of formula

When part of a salt, the formula of the acetate anion is written as CH3CO2−, C2H3O2−, and
CH3COO−. Chemists abbreviate acetate as OAc− and AcO−. Thus, HOAc is the abbreviation for
acetic acid, NaOAc for sodium acetate, and EtOAc for ethyl acetate.[2][3]

The name for acetate, sanctioned by IUPAC, the international committee charged with naming
chemical compounds, is ethanoate. This term is rarely encountered.[citation needed]
[edit] Salts
The acetate anion, [CH3COO]−, is one of the carboxylate family. It is the conjugate base of acetic
acid. Above pH of 5.5, acetic acid converts to acetate:[2]

CH3COOH ⇌ CH3COO− + H+

Many acetate salts are ionic, indicated by their tendency to dissolve well in water. A commonly
encountered acetate in the home is sodium acetate, a white solid that can be prepared by
combining vinegar and sodium bicarbonate ("bicarb"):

CH3COOH + NaHCO3 → CH3COO−Na+ + H2O + CO2

More specialized metal acetates can have complicated structures. Acetate is a relatively strong
ligand in coordination chemistry. Examples of acetate complexes include chromium(II) acetate
and basic zinc acetate.

[edit] Applications

Commercially important acetate salts are aluminium acetate, used in dyeing, ammonium acetate,
a precursor to acetamide, and potassium acetate, used as a diuretic. All three salts are colourless
and highly soluble in water.[4]

[edit] Esters
Acetate esters have the general formula CH3CO2R, where R is an organyl group. The esters are
the dominant forms of acetate in the marketplace. Unlike the acetate salts, acetate esters are often
liquids, lipophilic, and sometimes volatile. They are popular because they have inoffensive, often
sweet odors, they are inexpensive, and they are usually of low toxicity.

[edit] Applications

Almost half of acetic acid production is consumed in the production of vinyl acetate, precursor to
polyvinyl alcohol, which is a component of many paints. The second largest use of acetic acid is
consumed in the production of cellulose acetate. In fact, "acetate" is jargon for cellulose acetate,
which is used in the production of fibres or diverse products, e.g. the acetate discs used in audio
record production. Cellulose acetate can be found in many household products. Many industrial
solvents are acetates, including methyl acetate, ethyl acetate, isopropyl acetate, ethylhexyl
acetate. Butyl acetate is a fragrance used in food products.[4]

[edit] Acetate in biology

Acetate is a common anion in biology. It is mainly utilized by organisms in the form of acetyl
coenzyme A.[5]
Intraperitoneal injection of sodium acetate (20 or 60 mg per kg body mass) was found to induce
headache in sensitized rats, and it has been proposed that acetate resulting from oxidation of
ethanol is a major factor in causing hangovers. Increased serum acetate levels lead to
accumulation of adenosine in many tissues including the brain, and administration of the
adenosine receptor antagonist caffeine to rats after ethanol was found to decrease nociceptive
behavior.[6][7]

[edit] References
1. ^ March, J. “Advanced Organic Chemistry” 4th Ed. J. Wiley and Sons, 1992: New York.
ISBN 0-471-60180-2.
2. ^ a b Zumdahl, S. S. “Chemistry” Heath, 1986: Lexington, MA. ISBN 0-669-04529-2.
3. ^ Prior to the discovery and naming of actinium, the abbreviation "Ac" (or "AC") was
sometimes used in chemical formulas to indicate the acetate ion. For example, the
formula for sodium acetate might be given as "NaAc", rather than the more modern
"NaCH3COO" or "NaC2H3O2".
4. ^ a b Hosea Cheung, Robin S. Tanke, G. Paul Torrence "Acetic acid" in Ullmann's
Encyclopedia of Industrial Chemistry Weinheim, Germany: Wiley-VCH, 2005.
doi:10.1002/14356007.a01 045
5. ^ Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth
Publishing: New York, 2000. ISBN 1-57259-153-6.
6. ^ 'Acetate Causes Alcohol Hangover Headache in Rats' by Christina Maxwell et al.,
PLoS ONE 5(12): e15963.
7. ^ 'Is coffee the real cure for a hangover?' by Bob Holmes, New Scientist, Jan. 15 2011, p.
17.

[edit] Structures

space-filling model of the acetate anion

ball-and-stick model of the acetate anion



resonance hybrid of the acetate anion

canonical forms of the acetate anion