Carbon Dioxide → 3-Hydroxy-2-naphthoic acid

HRID 1732981Notes

Reaction equation

HRID 1732981 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[O-:11].[Na+].C1C2C(=CC=CC=2)C=CC=1O.[C:24](=[O:26])=[O:25]>O>[OH:11][C:2]1[C:3]([C:24]([OH:26])=[O:25])=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 86632-NaphtholHCID 23664630Sodium 2-naphtholate

Product 1

HCID 71043-Hydroxy-2-naphthoic acidYield 0.03%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixer 1 was fed hourly with 83 kg of sodium β-naphtholate, 130 g of light oil (boiling at 200°-310° C.) and 72 kg of β-naphthol, and they were dispersed and mixed. The dispersion was fed into a reactor 2 maintained at a carbon dioxide pressure of 3 kg/cm2.G at a rate of 285 kg/hr, and reacted at 270° C. The residence time was 4.5 hours. The reaction mixture which left the reactor 2 was cooled in a heat exchanger (not shown), and mixed with 420 liters/hr of water in the stirring tank 3. The temperature of the mixture was adjusted to 85° C., and the mixture was then fed into a separating tank 4 where it was separated at 85° C. into a light oil layer and an aqueous layer. The upper light oil layer was passed through a recovery device (not shown) to recover β-naphthol. The pH of the lower aqueous layer was adjusted to 5.5 with dilute sulfuric acid in a pH adjusting tank 5, and it was separated at 85° C. in a separating tank 6. By using a vacuum distillation device (not shown), β-naphthol was recovered from the separated lower tarry layer. The upper layer in the separating tank 6 was sent to a centrifugal extracting device 7 where it was extracted at 85° C. with 250 liters/hr of xylene. The xylene layer was sent to a recovery device (not shown) to recover β-naphthol. The aqueous layer in the extracting tank 7 was sent to an acid precipitation tank 8, and its pH was adjusted to 2.0 with dilute sulfuric acid at 85° C., followed by acid precipitation. Thus, 42.3 kg/hr of 2-hydroxynaphthalene-3-carboxylic acid (melting range 220°-221° C.; purity 99.5% β-naphthol content 0.03%) was obtained.

Workup

  1. additionwere dispersed
  2. additionmixed
  3. customThe dispersion was fed into a reactor
  4. customG at a rate of 285 kg/hr, and reacted at 270° C
  5. waitThe reaction mixture which left the reactor 2
  6. temperaturewas cooled in a heat exchanger (not
  7. customwas adjusted to 85° C.
  8. customwas separated at 85° C. into a light oil layer
  9. customto recover β-naphthol
  10. customwas separated at 85° C. in a separating tank 6
  11. distillationa vacuum distillation device (not
  12. customwas recovered from the
  13. customseparated lower tarry layer
  14. extractionwas extracted at 85° C. with 250 liters/hr of xylene
  15. customto recover β-naphthol
  16. customThe aqueous layer in the extracting tank 7 was sent to an acid precipitation tank 8, and its pH
  17. customwas adjusted to 2.0 with dilute sulfuric acid at 85° C.
  18. customfollowed by acid precipitation

Sources & evidence

ORD record
ord-013fe7b01d4248f88bee8a18d407e326
Source dataset
uspto-grants-1980_12
Patent number
US04239913

Reaction notes

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