Terephthalic Acid → Choline

HRID 436720

Reaction equation

HRID 436720 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

5

Reactant 2

HCID 7489Terephthalic Acid3×HCID 31255Choline, hydroxide

Product 2

HCID 305CholineHCID 7489Terephthalic Acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

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:

Workup

  1. customis removed by filtration
  2. concentrationThe filtrate is concentrated under reduced pressure
  3. temperaturecooled

Sources & evidence

ORD record
ord-36ef37dbef9f45058c8d0cddab49b5af
Source dataset
uspto-grants-1977_06
Patent number
US04028307

Linked notes

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