PRODUCT DESCRIPTION
1 of 3
Acetic Anhydride
l
CH3–C
ll
CH3–C
O
l
MW = 102.09
O
ll
(Ethanoic Anhydride,
Acetyl Oxide,
Acetyl Ether, Acetic Acid
Anhydride)
O
Acetic Acid, Anhydride, Chemical
Abstracts Registry Number 108-24-7
Wiswesser Line Formula Chemical
Notation 1V0V1
Acetic Anhydride is a clear, colorless liquid with a very pungent,
penetrating, vinegar-like odor. It
is soluble in ether, chloroform and
benzene. It reacts with alcohols.
Acetic anhydride is not very soluble in water, but reacts with it to
form acetic acid.
Acetic Anhydride is widely
employed industrially for its acetylating and dehydrating properties.
A major use for it is the acetylation of cellulose to produce acetate
fibers, plastics, coatings and films.
It is especially valuable for the
direct esterification of alcohols
where acetic acid cannot be used.
Another large use for Acetic
Anhydride is in the manufacture of
acetylsalicylic acid (aspirin), acetophenacetin, aceto-p-aminophenol, cortisone, acetanilide, theophylline, sulfa drugs, certain vitamins and hormones, and many
other pharmaceuticals and pharmaceutical intermediates.
Acetic Anhydride is also used to
produce acetyl ricinoleates, triacetin, acetyl tributyl citrate, and
other plasticizers.
Another chemical use is in the
manufacture of acetyl peroxide.
Acetic Anhydride is also used as
an intermediate in the manufacture
of explosives, weed killers, and in
the chemical treatment of paper
and textiles. Animal and vegetable
oils are acetylated with Acetic
Anhydride to change their solubility characteristics.
The reactions of Acetic Anhydride
are those of a typical acid anhydride.
PRODUCT DESCRIPTION
2 of 3
Acetic Anhydride
Chemical
Reactions
1.
Acetylation
CH3COONa
C6H4CH3NH2 + (CH3CO)2O →
C6H4CH3NHCOCH3 + CH+COOH
2.
Conversion into acids and acid derivatives
(a) Hydrolysis into acetic acid
(CH3CO)2O + H2O →2CH3COOH
(b) Ammonolysis into acetamide
(CH3CO)2O + 2NH3 →CH3CONH2 + CH3COONH4
(c) Alcoholysis into esters
(CH3CO)2O + CH3OH →CH3COOCH3 + CH3COOH
3.
Formation of ketones by Friedel-Crafts acylation
AICI3
→
(CH3CO)2O + ArH 
Lewis Acid CH2COAr + CH3COOH
4.
Condensation Reactions (Perkin)
CH3COONa
C6H5CHO + (CH3CO)2O 
C6H5CH=CHCOOCH3 + CH3COOH
→
∆
PRODUCT DESCRIPTION
3 of 3
Acetic Anhydride
Physical
Properties
Autoignition Temperature °C
Boiling Point at 760 mm Hg, °C
Boiling Point at 760 mm Hg, °F
Coefficient of Thermal Expansion
per °C at 20°C
Critical Pressure, atmospheres
Critical Temperature, °C
Dielectric Constant, at 20°C
Evaporation Rate (BuAc = 1)
Flammable Limits
(lower limit, vol %)
(upper limit, vol%)
Flash Point
Tag Open Cup, °F
Tag Closed Cup, °F
Freezing Point, °C
Heat of Combustion, kcal/mole
This information is based on our present
state of knowledge and is intended to provide general notes on our products and
their uses. It should therefore not be construed as guaranteeing specific properties
of the products described or their suitability
for a particular application. Any existing
industrial property rights must be observed.
The quality of our products is guaranteed
under our General Conditions of Sale.
PB-042-3
05/00 9072
392
139.6
283.3
1.12 x 10 –3
46
296
20.5
0.46
2.7
10.3
148
121
-73.1
431.9
Heat of Vaporization, cal/gm
at 15°C
Molecular Weight (formula)
Refractive Index n20
D
Solubility at 20°C, wt%, in water
Solubility in Alcohol
Solubility in Carbon Tetrachloride
Solubility in Chloroform
Solubility in Ether
Specific Gravity, 20/20°C
Specific Tension in Air at 20°C,
dynes/cm
Vapor Density (air = 1)
Vapor Pressure, 20°C, mm Hg
Viscosity at 20°C, centipoise
Weight, pounds per gallon at 20°C
(68°F)
121
102.09
1.3901
12 Decomposes
Infinite
Infinite
Soluble
Infinite
1.0828
32.7
4.0
4.0
0.901
9.01
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