High Quality Content by WIKIPEDIA articles! Phthalic anhydride is a versatile intermediate in organic chemistry, in part because it is bifunctional and cheaply available. Most characteristically, 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. 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. Like other anhydrides, the alcoholysis reaction is the basis of the manufacture of phthalate esters, which are widely used (and controversial see endocrine disruptor) plasticizers. In the 1980s, approximately 6.5x109 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 gives the mixed esters.

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