Water → 3-Hydroxy-2-naphthoic acid

HRID 1732983Notes

Reaction equation

HRID 1732983 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=C[C:14]=1[OH:23].[OH2:24]>>[OH:11][C:2]1[C:3]([C:14]([OH:23])=[O:24])=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1

Participants

4

Reactant 3

HCID 962WaterHCID 86632-NaphtholHCID 23664630Sodium 2-naphtholate

Product 1

HCID 71043-Hydroxy-2-naphthoic acid

Procedure

A mixer 1 was fed hourly with 83 kg of sodium β-naptholate, 181 kg of light oil (boiling at 200°-310° C.) and 57.2 kg of β-naphthol, and they were mixed and dispersed. About one-third of the light oil layer (upper layer) formed in the separating tank was removed, and fed into a recovery apparatus (not shown) to recover the dissolved β-naphthol and a tiny amount of sodium β-naphtholate as an aqueous solution of sodium β-naphtholate. The mixture remaining in the separating tank 2 consisted of 81 kg of sodium β-naphtholate, 42.4 kg of β-naphthol and 130 kg of light oil. The liquid mixture was fed into a reactor 3 at a rate of 253.4 kg per hour, and reacted with carbon dioxide at a pressure of 5 kg/cm2.G and a temperature of 250° C. The residence time was 5 hours. The reaction mixture which left the reaction tank 3 was cooled in a heat exchanger (not shown), and mixed with 400 liters/hour of water in a stirring tank 4, and sent to a separating tank 5 where the mixture was separated at 85° C. into a light oil layer and an aqueous layer. From the upper light oil layer, β-naphthol was recovered by using a recovery device (not shown). The lower aqueous layer was sent to a pH adjusting tank 6, and after adjusting its pH to 5.5 with dilute sulfuric acid, was introduced into a separating tank 7. From the lower tarry layer in the separating tank 7, β-naphthol was recovered by using a vacuum distillation device (not shown). The upper layer was sent to an extracting device 8 where it was extracted with 250 liters/hr of xylene at 80° C. The xylene layer was sent to a recovery device (not shown) to recover β-naphthol. The aqueous layer in the extracting tank 8 was sent to an acid precipitation tank 9 where it was subjected to acid precipitation at a pH of 2.0 using dilute sulfuric acid at 85° C. Thus, 41.3 kg/hr of 2-hydroxynaphthalene-3-carboxylic acid (melting range 220°-221° C.) was obtained.

Workup

  1. additionwere mixed
  2. additiondispersed
  3. customAbout one-third of the light oil layer (upper layer) formed in the separating tank
  4. customwas removed
  5. customto recover the dissolved β-naphthol
  6. customThe liquid mixture was fed into a reactor
  7. custom3 at a rate of 253.4 kg per hour, and reacted with carbon dioxide at a pressure of 5 kg/cm2
  8. customa temperature of 250° C
  9. waitThe reaction mixture which left the reaction tank 3
  10. temperaturewas cooled in a heat exchanger (not
  11. customwas separated at 85° C. into a light oil layer
  12. customFrom the upper light oil layer, β-naphthol was recovered
  13. additionwas introduced into a separating tank 7
  14. customFrom the lower tarry layer in the separating tank 7, β-naphthol was recovered
  15. distillationa vacuum distillation device (not
  16. extractionwas extracted with 250 liters/hr of xylene at 80° C
  17. customto recover β-naphthol
  18. customThe aqueous layer in the extracting tank 8 was sent to an acid precipitation tank 9 where it
  19. customwas subjected to acid precipitation at a pH of 2.0
  20. customat 85° C

Sources & evidence

ORD record
ord-74493a1530a446a9b9e4d2a4f8127900
Source dataset
uspto-grants-1980_12
Patent number
US04239913

Reaction notes

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