Benzoic anhydride

Benzoic anhydride is the organic compound with the formula (C6H5CO)2O. It is acid anhydride of benzoic acid and the simplest symmetrical aromatic acid anhydride. It is a white solid.

Benzoic anhydride[1]
Names
Preferred IUPAC name
Benzoic anhydride
Other names
Benzoic acid anhydride
Benzoyl anhydride
Benzoyl benzoate
Identifiers
3D model (JSmol)
516726
ChemSpider
ECHA InfoCard 100.002.084
EC Number
  • 202-291-1
UNII
Properties
C
14H
10O
3
Molar mass 226.23 g mol−1
Appearance White to off-white solid
Density 1.1989 g cm−3 at 15 °C
Melting point 42 °C (108 °F; 315 K)
Boiling point 360 °C (680 °F; 633 K)
-124.9·10−6 cm3/mol
Hazards
NFPA 704 (fire diamond)
Flammability code 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 fuelHealth code 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineReactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
2
1
1
Flash point 113[2] °C (235 °F; 386 K)
Related compounds
Related compounds
 Benzoic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Preparation and reactions

It is usually prepared by the dehydration reaction of benzoic acid, e.g. using acetic anhydride:[3]

2 C6H5CO2H + (CH3CO)2O → (C6H5CO)2O + 2 CH3CO2H

Alternatively, sodium benzoate can be treated with benzoyl chloride. It can be produced by dehydrating benzoic acid by heating.

Benzoic anhydride provides a convenient way to prepare benzoic esters:

(C6H5CO)2O + ROH → C6H5CO2H + C6H5CO2R

References
  1. "Sciencelab msds". Archived from the original on 2016-03-04. Retrieved 2015-12-26.
  2. "aldrich product page".
  3. H. T. Clarke and E. J. Rahrs (1923). "Benzoic Anhydride". Org. Synth. 3: 21. doi:10.15227/orgsyn.003.0021.CS1 maint: uses authors parameter (link)
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