benzoic anhydride
{{Chembox
| ImageFile1 = Benzoic anhydride.svg
| ImageFile2 = Benzoic-anhydride-based-on-similar-xtals-3D-balls.png
| PIN = Benzoic anhydride
| OtherNames = Benzoic acid anhydride
Benzoyl anhydride
Benzoyl benzoate
|Section1={{Chembox Identifiers
| CASNo = 93-97-0
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 9K7X34FOV2
| PubChem = 7167
| ChemSpiderID = 6899
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| EINECS = 202-291-1
| Beilstein = 516726
| SMILES = c1ccccc1C(=O)OC(=O)c2ccccc2
| StdInChI = InChI=1S/C14H10O3/c15-13(11-7-3-1-4-8-11)17-14(16)12-9-5-2-6-10-12/h1-10H
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = CHIHQLCVLOXUJW-UHFFFAOYSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
}}
|Section2={{Chembox Properties
| Formula = {{Chem|C|14|H|10|O|3}}
| MolarMass = 226.23 g mol−1
| Appearance = White to off-white solid
| Density = 1.1989 g cm−3 at 15 °C
| MeltingPtC = 42
| BoilingPtC = 360
| MagSus = −124.9·10−6 cm3/mol
}}
|Section5={{Chembox Hazards
| NFPA-F = 2
| NFPA-H = 1
| NFPA-R = 1
| FlashPtC = 113{{cite web|title=aldrich product page|url=http://www.sigmaaldrich.com/catalog/product/aldrich/385980?lang=hu®ion=HU}}
}}
|Section6={{Chembox Related
| OtherCompounds = Benzoic acid
}}
}}
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:{{cite journal|title=Benzoic Anhydride|author1=H. T. Clarke |author2=E. J. Rahrs |journal=Org. Synth.|year=1923|volume=3|page=21|doi=10.15227/orgsyn.003.0021}}
: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. {{Citation needed|date=June 2022}}
Benzoic anhydride provides a convenient way to prepare benzoic esters:
:(C6H5CO)2O + ROH → C6H5CO2H + C6H5CO2R
References
{{Reflist}}