Terephthalic Acid → Choline

Reaction equation

[C:1]([OH:12])(=[O:11])[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[OH-].[OH:14][CH2:15][CH2:16][N+:17]([CH3:20])([CH3:19])[CH3:18]>CO>[OH:14][CH2:15][CH2:16][N+:17]([CH3:20])([CH3:19])[CH3:18].[C:1]([OH:12])(=[O:11])[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1

Participants

Procedure

Terephthalic acid (16 parts) is slurried in methanol (80 parts) at 0° C. A 45% solution of 2-hydroxyethyltrimethylammonium hydroxide (choline base) in methanol (10 parts) is added to the slurried terephthalic acid. After stirring for 30 minutes the excess terephthalic acid is removed by filtration. The filtrate is concentrated under reduced pressure and cooled, giving the mono-2-hydroxyethyltrimethylammonium salt of terephthalic acid as a precipitate which is isolated by filtration. That the product is the mono-salt is shown by the following elemental analysis: