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125733

Sigma-Aldrich

Phthalic anhydride

ReagentPlus®, 99%

Synonym(s):

1,2-Benzenedicarboxylic anhydride, 1,3-Isobenzofurandione, Phthalic acid anhydride

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About This Item

Empirical Formula (Hill Notation):
C8H4O3
CAS Number:
85-44-9
Molecular Weight:
148.12
Beilstein:
118515
EC Number:
201-607-5
MDL number:
MFCD00005918
UNSPSC Code:
12352100
PubChem Substance ID:
57646985
NACRES:
NA.21

vapor density

5.1 (vs air)

Quality Level

200

vapor pressure

<0.01 mmHg ( 20 °C)

product line

ReagentPlus®

Assay

99%

form

flakes

autoignition temp.

1058 °F

expl. lim.

10.4 %

bp

284 °C (lit.)

mp

131-134 °C (lit.)

SMILES string

O=C1OC(=O)c2ccccc12

InChI

1S/C8H4O3/c9-7-5-3-1-2-4-6(5)8(10)11-7/h1-4H

InChI key

LGRFSURHDFAFJT-UHFFFAOYSA-N

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General description

Phthalic anhydride is an industrially important chemical. It can be prepared from o-xylene or naphthalene. It is widely used for the industrial preparation of plasticizers for PVC (polyvinyl chloride).
Phthalic anhydride can be synthesized via oxidation of o-xylene, in the presence of V2O5/TiO2 monolithic catalyst supported by aluminium honeycomb.

Application

Phthalic anhydride may be used in the synthesis of the following compounds:
  • pthalimide
  • phenolphthalein
  • anthracene

Legal Information

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Resp. Sens. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 1

Flash Point(F)

305.6 °F

Flash Point(C)

152 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

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"Conductive monolithic catalysts: development and industrial pilot tests for the oxidation of o-xylene to phthalic anhydride"
Groppi G, et al.
Industrial & Engineering Chemistry Research, 51(22), 7590-7596 (2011)
Phthalic anhydride from o-xylene catalysis: science and engineering.
Nikolov V, et al.
Catalysis Reviews: Science and Engineering, 33(3-4), 319-374 (1991)
Catalysts, kinetics and reactor design in phthalic anhydride synthesis.
Wainwright MS and Foster NR.
Catalysis Reviews: Science and Engineering, 19(2), 211-292 (1979)
A Micó-Tormos et al.
Journal of chromatography. A, 1203(1), 47-53 (2008-07-25)
The esterification of fatty alcohol ethoxylates (FAEs) with phthalic anhydride in 1,4-dioxane was studied. At 110 degrees C and in the presence of urea, which increased the reaction rate, esterification was completed in 60 min. The reaction yield did not
Yuichi Kajita et al.
Journal of the American Chemical Society, 130(51), 17226-17227 (2008-12-04)
An intermolecular nickel-catalyzed addition reaction has been developed where phthalic anhydrides react with alkynes to afford substituted isocoumarins. A mechanistic rationale is proposed, implying reductive elimination of Ni(0) promoted by ZnCl(2) cocatalyst as the key step of the catalytic cycle.
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