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
  • InChI=1S/C14H10O3/c15-13(11-7-3-1-4-8-11)17-14(16)12-9-5-2-6-10-12/h1-10H Y
    Key: CHIHQLCVLOXUJW-UHFFFAOYSA-N Y
  • 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)
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

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.{{cite journal}}: CS1 maint: uses authors parameter (link)
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.