Phenol → Phenolphthalein

Participants

Reaction Conditions

Reaction Steps

In a 250 mL round bottom flask equipped with mechanical stirrer, thermometer, nitrogen inlet and reflux condenser, 10.0 g of phthalic anhydride (0.067 moles) and 15 g of ionic liquid catalyst composition (zinc chloride and 1-butyl-3-methyl-imidazolium) (60 wt. % based on total weight of reactants) were charged to the round bottom flask followed by 14.3 g phenol (2.25 molar equivalents based on phthalic anhydride) and 1.9 g chlorosulphonic acid (0.2 molar equivalents based on phthalic anhydride), while maintaining the round bottom flask in a nitrogen atmosphere at 50 to 60° C. The reaction mixture was then heated with stirring at 120° C. (bath temperature). Over the course of the reaction (24 hours), the reaction mass progressively turned from orange to brownish orange to deep brown. After 24 hours, the reaction mixture comprising phenolphthalein was then quenched with 150 mL toluene. The viscous mass produced by the addition of toluene was stirred at 85° C. for about 30 min. The supernatant (containing the ionic liquid catalyst composition, toluene, and unreacted starting material) was decanted and the remaining viscous mass was then heated with 150 mL water and stirred at 85° C. for about 30 min. The solidified phenolphthalein was filtered while hot and washed until the supernatant was neutral with cold, distilled water to obtain crude phenolphthalein. The resulting brownish yellow solid was dried under vacuum at 100° C. overnight. The yield of crude phenolphthalein was 18.7 g (89 mol %) and the purity was 96.08 wt. %.

Provenance & Evidence