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108-24-7

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Basic Information
CAS No.: 108-24-7
Name: Acetic anhydride
Article Data: 585
Cas Database
Molecular Structure:
Molecular Structure of 108-24-7 (Acetic anhydride)
Formula: C4H6O3
Molecular Weight: 102.09
Synonyms: Acetanhydride;Acetic acid, anhydride;Acetic oxide;Acetyl acetate;Acetyl anhydride;Acetyl ether;Acetyl oxide;Anhydrid kyseliny octove;Anhydride acetique;Anidride acetica;Octowy bezwodnik;UNII-2E48G1QI9Q;
EINECS: 203-564-8
Density: 1.073 g/cm3
Melting Point: -73.1 °C
Boiling Point: 141.137 °C at 760 mmHg
Flash Point: 54.444 °C
Solubility: reacts with water
Appearance: Colorless liquid
Hazard Symbols: CorrosiveC
Risk Codes: 11-20/21/22-37/38-41-34-10-19
Safety: 26-39-45-36/37/39-33-16
Transport Information: UN 2924 3/PG 2
PSA: 43.37000
LogP: 0.09600
Synthetic route
563-63-3

silver(I) acetate

A

108-24-7

acetic anhydride

B

20667-12-3

silver(l) oxide

Conditions
ConditionsYield
In neat (no solvent) byproducts: Ag, CO2; 300-400°C, quartz-tube, Ar-atmosphere (1atm.), exclusion of H2O;;A 93%
B 96%
In neat (no solvent) calculation of change of free enthalpy during thermic decompn.;;
3808-00-2

α-acetoxy-α-phenylbenzeneacetic acid

A

464-72-2

tetraphenylethane-1,2-diol

B

108-24-7

acetic anhydride

Conditions
ConditionsYield
With triethylamine In acetonitrile Ambient temperature; electrolysis;A 93%
B n/a
With triethylamine In acetonitrile Product distribution; Ambient temperature; electrolysis;A 93%
B n/a
64-19-7

acetic acid

108-24-7

acetic anhydride

Conditions
ConditionsYield
With PEG-1000; sulfated zirconia at 40℃; for 2h; neat (no solvent);90%
With thionyl chloride In dichloromethane at 22 - 25℃; for 0.0833333h;88.8%
With diammonium phosphate at 725℃; under 195.02 Torr; Reagent/catalyst; Pyrolysis;48.8%
65988-98-9

(Acetoxy)diphenylphosphane

A

108-24-7

acetic anhydride

B

complex of tetraphenyldiphosphine with tin tetrabromide

C

complex of bis(diphenyldiphosphinic) anhydride with tin tetrabromide

Conditions
ConditionsYield
With stannic bromide In dichloromethane for 72h; Product distribution; Ambient temperature;A n/a
B n/a
C 90%

6-(4-aminophenyl)-1,3-dihydro-5-methyl-2H-imidazo[4,5-b]pyridin-2-one hydrochloride

A

6-[4-(Acetylamino)phenyl]-1,3-dihydro-5-methyl-2H-imidazo[4,5-b]pyridin-2-one

B

108-24-7

acetic anhydride

Conditions
ConditionsYield
A n/a
B 90%
A n/a
B 90%
39652-00-1

diphenyltellurium di(acetate)

A

1206-36-6

diphenyltellurium dichloride

B

108-24-7

acetic anhydride

Conditions
ConditionsYield
With acetyl chloride In chloroform for 5h; Heating;A 89%
B 81%
64-19-7

acetic acid

77339-54-9

N,N,N',N'-tetraethyl-P-(trichloromethyl)phosphonoimidic diamide

A

67-66-3

chloroform

B

38590-11-3

N,N,N',N'-tetraethylphosphoric triamide

C

108-24-7

acetic anhydride

Conditions
ConditionsYield
In diethyl ether for 3h; Ambient temperature;A 89%
B 51%
C n/a
84103-76-4

O-acetyl S,S-diethyl phosphorodithioite

A

1486-42-6

diethyl phosphorochloridodithioite

B

108-24-7

acetic anhydride

Conditions
ConditionsYield
With acetyl chloride for 0.5h; Ambient temperature;A 72%
B 89%
84103-76-4

O-acetyl S,S-diethyl phosphorodithioite

75-36-5

acetyl chloride

A

1486-42-6

diethyl phosphorochloridodithioite

B

108-24-7

acetic anhydride

Conditions
ConditionsYield
at 20℃; for 0.5h;A 72%
B 89%
65988-98-9

(Acetoxy)diphenylphosphane

A

108-24-7

acetic anhydride

B

complex of tetraphenyldiphosphine with tin tetrachloride

C

complex of bis(diphenyldiphosphinic) anhydride with tin tetrachloride

Conditions
ConditionsYield
With tin(IV) chloride In dichloromethane for 72h; Product distribution; Ambient temperature;A n/a
B n/a
C 88%
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Chemistry

Molecular Structure:

Molecular Formula: C4H6O3
Molecular Weight: 102.09
IUPAC Name: Acetyl acetate
Synonyms of Acetic anhydride (CAS NO.108-24-7): Acetanhydride ; Acetic acid, anhydride ; Acetic oxide ; Acetyl acetate ; Anhydride acetique ; Anidride acetica ; Essigsaeureanhydrid ; Acetic acid, 1,1'-anhydride
CAS NO: 108-24-7
EINECS: 203-564-8
H bond acceptors: 3
H bond donors: 0
Freely Rotating Bonds: 2
Polar Surface Area: 43.37 Å2
Index of Refraction: 1.386
Molar Refractivity: 22.38 cm3
Molar Volume: 95.1 cm3
Surface Tension: 29.1 dyne/cm
Density: 1.072 g/cm3
Flash Point: 54.4 °C
Enthalpy of Vaporization: 37.83 kJ/mol
Boiling Point: 141.1 °C at 760 mmHg
Vapour Pressure: 5.94 mmHg at 25°C
Melting Point: -73.1 °C
Storage temp: Store at RT.
Water Solubility: REACTS
Sensitive: Moisture Sensitive
Stability: Stability Flammable. Incompatible with strong oxidizing agents, water, strong bases, alcohols.
Appearance: Colorless liquid
Product Categories of Acetic anhydride (CAS NO.108-24-7): Pharmaceutical Intermediates;Biochemistry;Reagents for Oligosaccharide Synthesis;Chemistry;Acylation ReagentsDerivatization Reagents GC;AminesDerivatization Reagents;GC Derivatization Reagents, by Application;Acylation ReagentsDerivatization Reagents;Analytical/Chromatography;Derivatization Reagents;Derivatization Reagents GC;Reagents for Acylation;ACS GradeOrganic Building Blocks;Carbonyl Compounds;Carboxylic Acid Anhydrides;Essential Chemicals;Routine Reagents;A-B, Puriss p.a. ACSDerivatization Reagents;Analytical Reagents for General Use;Derivatization Reagents HPLC;Puriss p.a. ACS;UV-VIS;A-B, Puriss p.a. ACSAnalytical/Chromatography;Reagent Plus;Alkaline β-eliminationFatty Acids;AnhydridesDeglycosylation Strategies;Reagent GradeProtein Modification;Reagents for lysine modification;Chemical Deglycosylation;Deglycosylation Strategies;HydrazinolysisEssential Chemicals;Saturated fatty acids and derivatives;Specific Amino Acid Modification

Uses

 Acetic anhydride (CAS NO.108-24-7) is mainly used for acetylations leading to commercially significant materials. It is mainly used for the conversion of cellulose to cellulose acetate, which is a component of photographic film and other coated materials. For the same reason  it is used in the production of aspirin, acetylsalicylic acid, which is prepared by the acetylation of salicylic acid. It is also used as a wood preservative via autoclave impregnation to make a longer lasting timber. In starch industry, Acetic anydride is a common acetylation compound, used for the production of modified starches.

Production

  Acetic anhydride (CAS NO.108-24-7) may be produced by three different methods.
The first procedure involves the in situ production from acetaldehyde of peracetic acid, which in turn reacts with more acetaldehyde to yield the anhydride.
          CH3CH=O + O2 → CH3C(=O)OH
  CH3C(=O)OH + CH3C=O → CH3C(=O)O(O=)CCH3 + H2O
In the preferred process, acetic acid (or acetone) is pyrolyzed to ketene, which reacts with acetic acid to form acetic anhydride.
          CH3C(=O)OH → CH2=C=O + H2O
    CH2=C=O + CH3C(=O)OH → CH3C(=O)O(O=)CCH3
Another process to make acetic anhydride involves carbon monoxide insertion into methyl acetate.
       CH3C(=O)OCH3 → CH3C(=O)O(O=)CCH3

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
rabbit LD50 skin 4mL/kg (4mL/kg)   Union Carbide Data Sheet. Vol. 8/7/1963,
rat LC50 inhalation 1000ppm/4H (1000ppm)   "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 607, 1969.
rat LD50 oral 1780mg/kg (1780mg/kg)   AMA Archives of Industrial Hygiene and Occupational Medicine. Vol. 4, Pg. 119, 1951.

Safety Profile

Hazard Codes: CorrosiveC,HarmfulXn,FlammableF,IrritantXi
Risk Statements: 10-11-19-34-41-37/38-20/21/22
R10: Flammable. 
R11: Highly flammable. 
R19: May form explosive peroxides. 
R34: Causes burns. 
R41: Risk of serious damage to the eyes. 
R37/38: Irritating to respiratory system and skin. 
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 26-16-33-45-36/37/39
S16: Keep away from sources of ignition. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S33: Take precautionary measures against static discharges.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
RIDADR: UN 2924 3/PG 2
WGK Germany: 3
RTECS: AK1925000
F: 21
HazardClass: 8
PackingGroup: II
HS Code: 29152400