o-Xylene

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o-Xylene

CAS number
ChemSpider
UNII
DrugBank
KEGG
ChEBI
ChEMBL
RTECS number
Jmol-3D images

Identifiers
95-47-6
6967
Z2474E14QP
DB03029
C07212
CHEBI:28063
CHEMBL45005
ZE2450000
Image 1
SMILES

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InChI
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Molecular formula
Molar mass
Appearance

Properties
C8H10
106.17 g mol1
Colorless liquid

Melting point

-24 C, 249 K, -11 F

Boiling point

144.4 C, 418 K, 292 F

Solubility in water
Solubility in ethanol
Solubility in diethyl ether
Refractive index (nD)
Viscosity
Dipole moment

insoluble
very soluble
very soluble
1.50545
1.1049 cP at 0 C
0.8102 cP at 20 C
Structure
0.64 D [1]
Hazards

MSDS
EU classification
R-phrases
S-phrases

External MSDS
Harmful (Xn) Flammable (F)
R11 R20 R21 R38
S25

NFPA 704

3
2
0

Flash point

32 C
Related compounds
m-xylene
Related aromatic
p-xylene
hydrocarbons
toluene
Supplementary data page
Structure and
n, r, etc.
properties
Thermodynamic
Phase behaviour
data
Solid, liquid, gas
Spectral data
UV, IR, NMR, MS
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Except where noted otherwise, data are given for materials in
their standard state (at 25 C, 100 kPa)
Infobox references

Phthalic anhydride
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Phthalic anhydride

IUPAC name[hide][hide]
2-benzofuran-1,3-dione [1]
Other names[hide][hide]
Isobenzofuran-1,3-dione
Identifiers
CAS number

85-44-9

ChemSpider

6552

ChEBI

CHEBI:36605

RTECS number

TI3150000

Jmol-3D images

Image 1

SMILES
[show][show]
InChI
[show][show]
Properties
Molecular formula

C8H4O3

Molar mass

148.1 g/mol

Appearance

white flakes

Density

1.53 g/cm3, solid

Melting point

131 C

Boiling point

295 C subl.

Solubility in water

0.62 g/100g (2025 C);

19.0 g/100g (100 C);
reacts slowly
Hazards

R-phrases

R22, R37/38, R41, R42/43

S-phrases

(S2), S23, S24/25, S26,

S37/39, S46

NFPA 704

3
0
Flash point

152 C
Related compounds

Phthalic acid
Related compounds Phthalimide
Phthalide
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Except where noted otherwise, data are given for
materials in their standard state (at 25 C,
100 kPa)
Infobox references

Phthalic anhydride is the organic compound with the formula C6H4(CO)2O. It is the anhydride
of phthalic acid. This colourless solid is an important industrial chemical, especially for the
large-scale production of plasticizers for plastics. In 2000, the world wide production volume of
phthalic anhydride is estimated to be about 3 232 000 tonnes per year.[1]

Synthesis and production

Phthalic anhydride was first reported in 1836 by Auguste Laurent. It is presently obtained by
catalytic oxidation of ortho-xylene and naphthalene ("Gibbs phthalic anhydride process"):
C6H4(CH3)2 + 3 O2 C6H4(CO)2O + 3 H2O
C10H8 + 4.5 O2 C6H4(CO)2O + 2 H2O + 2 CO2

The catalyst that is used for the oxidation of xylene is a modified vanadium pentoxide (V2O5).
When separating the phthalic anhydride from byproducts such as o-xylene in water, or maleic
anhydride, a series of switch condensers is required. Phthalic anhydride can also be prepared
from phthalic acid:[2]

Applications in industry and organic synthesis

Phthalic anhydride is a versatile intermediate in organic chemistry, in part because it is
bifunctional and cheaply available. It undergoes hydrolysis and alcoholysis. Hydrolysis by hot
water forms ortho-phthalic acid. This process is reversible: Phthalic anhydride re-forms upon
heating the acid above 180 C.[3] Hydrolysis of anhydrides is not typically a reversible process.
However, phthalic acid is easily dehydrated to form phthalic anhydride due to the creation of a
thermodynamically favorable 5-membered ring.

Preparation of phthalate esters

As with other anhydrides, the alcoholysis reaction is the basis of the manufacture of phthalate
esters, which are widely used (and controversial - see endocrine disruptor) plasticizers.[2] In the
1980s, approximately 6.5109 kg of these esters were produced annually, and the scale of
production was increasing each year, all from phthalic anhydride. The process begins with the
reaction of phthalic anhydride with alcohols, giving the monoesters:
C6H4(CO)2O + ROH C6H4(CO2H)CO2R

The second esterification is more difficult and requires removal of water:

C6H4(CO2H)CO2R + ROH

C6H4(CO2R)2 + H2O