Carbon Dioxide → HCID 178524617, compound

HRID 1637397Notes

Reaction equation

HRID 1637397 reaction equation
[CH:1]([O-:3])=[O:2].[K+:4].[C:5](=[O:7])=[O:6].C(=O)([O-])[O-].[K+].[K+].[C:14]1([CH:21]=[CH:20][C:18]([OH:19])=[CH:17][CH:16]=1)[OH:15]>O>[OH:15][C:14]1[CH:21]=[C:20]([C:5]([O-:7])=[O:6])[C:18]([OH:19])=[CH:17][C:16]=1[C:1]([O-:3])=[O:2].[K+:4].[K+:4]

Participants

6

Reactant 4

HCID 280Carbon Dioxide2×HCID 785HydroquinoneHCID 11430Potassium CarbonateHCID 2735122Potassium Formate

Product 1

HCID 178524617HCID 178524617, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a glass reactor having a bottom outlet and equipped with a spiral-shaped stirrer and a thermocouple potassium formate (329 g) was melted under vacuum. When the temperature of the melt reached 190° C., the reactor was aerated with CO2 and potassium carbonate (125.04 g, 0.906 mole) and hydroquinone (80.06 g, 0.728 mole) were added to the melt. The reaction mixture was stirred at 200° C. under 1.5 bar CO2 for four and one-half hours. Then 250 ml of water were added to the reaction mixture, and the slurry was removed from the reactor and crystallized from 3.5 l of boiling water. After cooling, the product was filtered off and washed with ice water. Drying under vacuum at 100° C. produced 87% of pale yellow dipotassium 2,5-dihydroxyterephthalate (K2 -2,5-DHTA, 173.77 g, 0.634 mole). The filtrate was boiled down and the residue was reused in a carboxylating reaction using potassium carbonate (95.90 g, 0.695 mole) and hydroquinone (75.06 g, 0.682 mole). According to the above specification, 98% pale yellow K2 -2,5-DHTA (184.31 g, 0.673 mole) was obtained. Repetition of this recycle process using potassium carbonate (94.14 g, 0.682 mole) and hydroquinone (75.16 g, 0.683 mole) according to the above specification produced 95% pale yellow K2 -2,5-DHTA (178.65 g, 0.652 mole).

Workup

  1. customIn a glass reactor having
  2. customa bottom outlet and equipped with a spiral-shaped stirrer
  3. customreached 190° C.
  4. additionwere added to the melt
  5. customthe slurry was removed from the reactor
  6. customcrystallized from 3.5 l of boiling water
  7. temperatureAfter cooling
  8. filtrationthe product was filtered off
  9. washwashed with ice water
  10. customDrying under vacuum at 100° C.

Sources & evidence

ORD record
ord-d91bfd956f3b4119a1b674df5c2d7111
Source dataset
uspto-grants-2000_03
Patent number
US06040478

Reaction notes

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