Benzoic anhydride

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
  • InChI=1S/C14H10O3/c15-13(11-7-3-1-4-8-11)17-14(16)12-9-5-2-6-10-12/h1-10H checkY
    Key: CHIHQLCVLOXUJW-UHFFFAOYSA-N checkY
  • c1ccccc1C(=O)OC(=O)c2ccccc2
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)
NFPA 704 four-colored diamondHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 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 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g. calciumSpecial hazards (white): no code
1
2
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

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

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; E. J. Rahrs (1923). "Benzoic Anhydride". Org. Synth. 3: 21. doi:10.15227/orgsyn.003.0021.
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