1-Chloronaphthalene → HCID 22731614, compound

Participants

Reaction Steps

In a 20 liter stainless steel reaction vessel were mixed 817 g (2.08 mols) of perylene-3,4,9,10-tetracarboxylic acid dianhydride, 1169 g (10.4 mols) of o-phenylenediamine, and 9.36 liters of 1-chloronaphthalene. The mixture obtained was heated to a temperature of from 240° C. to 250° C. for 3 hours with stirring and then cooled to room temperature. Then, a solid product formed was obtained by filtering the reaction mixture with a filter cloth and then washed thrice with N,N-dimethylformamide. Thereafter, the solid product was mixed with an alcohol solution of sodium hydroxide to provide a slurry. After filtering the slurry, the solid product collected was washed with N,N-dimethylformamide and then methanol, and then dried overnight in an oven at 95° C. to provide 1100 g of a bisbenzimidazole perylene pigment (a mixture of the cis form and the trans form). Furthermore, the pigment was purified by sublimation. The powder X-ray diffraction pattern of the pigment after the purification by sublimation is shown in FIG. 1 (showing strong peaks at 0.8°, 10.2°, and 12.5°).

Provenance & Evidence