Ammonia → Naphthalimide

Participants

Reaction Conditions

Reaction Steps

1,8-naphthalic anhydride (50.00 g, 0.252 mol, 1.0 eq), 32.8 ml of 29% aqueous ammonia (29.52% g, or 8.56 g dry, 0.504 mol, 2.0 eq) and water (115 g) were mixed to form a yellow slurry. The yellow slurry was heated with stirring to 70° C. then held at that temperature for 90 minutes for a total heating time of about 2 hours. After the heating period, the mixture was cooled to room temperature and filtered. The product was then washed with 500 to 600 ml of water until the pH of the wash water was neutral (pH 7). The product (i.e. 1,8-naphthalimide) was isolated as a wet filtercake (59.67 g, dry content=82.28%, representing 49.10 g of dry 1,8-naphthalimide, 99% yield), which was suitable for converting to 3, 4, 9, 10-perylenetetracarboxylic diimide. The purity of 1,8-naphthalimide was above 99% as determined by Gas Chromatography with a melting point of about 301-303° C.

Provenance & Evidence