Phthalic anhydride is the organic compound

Organic compound

An organic compound is any member of a large class of gaseous, liquid, or solid chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of carbon-containing compounds such as carbides, carbonates, simple oxides of carbon, and cyanides, as well as the...

 with the formula

Chemical formula

A chemical formula or molecular formula is a way of expressing information about the atoms that constitute a particular chemical compound....

 C₆H₄(CO)₂O. It is the anhydride of phthalic acid

Phthalic acid

Phthalic acid is an aromatic dicarboxylic acid, with formula C6H42. It is an isomer of isophthalic acid and terephthalic acid. Although phthalic acid is of modest commercial importance, the closely related derivative phthalic anhydride is a commodity chemical produced on a large...

. This colourless solid is an important industrial chemical, especially for the large-scale production of plasticizer

Plasticizer

Plasticizers or dispersants are additives that increase the plasticity or fluidity of the material to which they are added; these include plastics, cement, concrete, wallboard, and clay. Although the same compounds are often used for both plastics and concretes the desired effects and results are...

s for plastics. In 2002, approximately 4.6 billion kilograms were produced.
Phthalic anhydride was first reported in 1836 by Laurent. It is presently obtained by catalytic oxidation of ortho-xylene

Xylene

Xylene encompasses three isomers of dimethylbenzene. The isomers are distinguished by the designations ortho- , meta- , and para- , which specify to which carbon atoms the two methyl groups are attached...

 and naphthalene

Naphthalene

Naphthalene is an organic compound with formula . It is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass. As an aromatic hydrocarbon, naphthalene's structure consists of a fused pair of benzene rings...

 (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

When separating the phthalic anhydride from byproducts such as o-xylene in water, or maleic anhydride

Maleic anhydride

Maleic anhydride is an organic compound with the formula C2H22O. It is the acid anhydride of maleic acid and in its pure state it is a colourless or white solid with an acrid odour....

, a series of “switch condensers” is required.