Water → 3-Hydroxy-2-naphthoic acid

HRID 848838Notes

Reaction equation

HRID 848838 reaction equation
C1C2C(=CC=CC=2)C=C[C:2]=1[OH:11].[CH:12]([C:15]1[C:16]([CH:22]([CH3:24])C)=[C:17](C)[CH:18]=[CH:19][CH:20]=1)([CH3:14])C.[OH-:25].[Na+].[OH2:27]>>[OH:25][C:24]1[C:14]([C:2]([OH:11])=[O:27])=[CH:12][C:15]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:22]=1

Participants

5

Reactant 4

HCID 962WaterHCID 86632-NaphtholHCID 14798Sodium HydroxideHCID 198843991-Methyl-2,3-di(propan-2-yl)benzene

Product 1

HCID 71043-Hydroxy-2-naphthoic acid

Procedure

A reactor was charged continuously with 50 kg/hr of β-naphthol, 20 kg/hr of diisopropyltoluene (isomer mixture) and 13.9 kg/hr of 50% aqueous sodium hydroxide solution while it was held at 100° C. in a nitrogen atmosphere. The mixture was fed to a fractionating column at a rate of 83.9 kg/hr while water was withdrawn as an overhead distillate at a rate of 10.1 kg/hr. During the fractionation, the reboiler was held at 230° C. The residue from the column was supplied continuously to an autoclave with a metering pump under pressure at a rate of 73.8 kg/hr for reaction with carbon dioxide. The reaction conditions were as follows: a temperature of 260° C., a total pressure of 7.0 kg/cm2G, and a residence time of 1.5 hr. The reaction mass was recovered from the autoclave at a rate of 77.1 kg/hr and supplied to a water addition tank where it was mixed with 165 kg/hr of water, and the mixture was treated with sulfuric acid to adjust its pH to 6.0 at a controlled temperature between 85° and 90° C. The mixture was supplied to a separation tank where it was separated into the organic layer and the aqueous layer. The aqueous layer was fed to an extraction tank where β-naphthol was extracted with 60 kg/hr of toluene. The extraction temperature was between 80° and 85° C. The mixture was then supplied to a separation tank where it was separated into the organic layer and the aqueous layer. The aqueous layer was sent to an acid precipitation tank where it was adjusted to a pH of 2.0 with sulfuric acid at 80° C. The precipitate was filtered to give 14.4 kg/hr of 2-hydroxynaphthalene-3-carboxylic acid (99% purity and β-naphthol content less than 0.1%). The yield of 2-hydroxynaphthalene-3-carboxylic acid was 44% on the basis of the sodium β-naphtholate and was 85% on the basis of β-naphthol consumed.

Workup

  1. customwas held at 100° C. in a nitrogen atmosphere
  2. customwas withdrawn as an overhead distillate at a rate of 10.1 kg/hr
  3. customwas held at 230° C
  4. customThe residue from the column was supplied continuously to an autoclave with a metering pump under pressure at a rate of 73.8 kg/hr for reaction with carbon dioxide
  5. customThe reaction conditions
  6. customa temperature of 260° C.
  7. customa residence time of 1.5 hr
  8. customThe reaction mass was recovered from the autoclave at a rate of 77.1 kg/hr
  9. additionsupplied to a water addition tank where it
  10. additionwas mixed with 165 kg/hr of water
  11. additionthe mixture was treated with sulfuric acid
  12. customat a controlled temperature between 85° and 90° C
  13. customwas separated into the organic layer
  14. extractionwas extracted with 60 kg/hr of toluene
  15. customwas between 80° and 85° C
  16. customwas separated into the organic layer
  17. customThe aqueous layer was sent to an acid precipitation tank where it
  18. customwas adjusted to a pH of 2.0 with sulfuric acid at 80° C
  19. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-84243e242cdc439482f2d6b49c1c3075
Source dataset
uspto-grants-1981_10
Patent number
US04297508

Reaction notes

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