benzoic anhydride

{{Chembox

| Reference = {{cite web|title=Sciencelab msds|url=http://www.sciencelab.com/msds.php?msdsId=9923052|access-date=2015-12-26|archive-url=https://web.archive.org/web/20160304053119/http://www.sciencelab.com/msds.php?msdsId=9923052|archive-date=2016-03-04|url-status=dead}}

| 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