Acetone → N,N'-1,3-Phenylenedimaleimide

Participants

Reaction Conditions

Reaction Steps

A flask was equipped as in Example 1. To a solution of maleic anhydride (1.92 parts) in 4.8 parts acetone was added a solution of 1 part m-phenylenediamine, 0.32 part triethylamine and 1.6 parts acetone over a 15-minute period. A precipitate formed during that time. The heterogeneous reaction mixture was maintained at 40° C. for 30 minutes. Magnesium chloride hexahydrate (0.08 part) and 2.44 parts acetic anhydride were added all at once. The temperature was raised to 50° C. and maintained for 3 hours. After 30 minutes, the reaction mixture became homogeneous and amber in color. Five minutes later, the product began to precipitate. At the end of the reaction time, the mixture was cooled and 12 parts water added. The precipitated product was collected by vacuum filtration, washed with water, and dried for 24 hours at 60° C. in a vacuum oven. A 92% yield of N,N'-m-phenylenedimaleimide, m.p. 204°-205° C., was obtained.

Provenance & Evidence