Sodium Carbonate → 2-Naphthalenesulfonic acid, 5-amino-6-ethoxy-

HRID 1759512Notes

Reaction equation

HRID 1759512 reaction equation
[NH:1]([C:5]1[C:14]2[C:9](=[CH:10][C:11]([S:15]([OH:18])(=[O:17])=[O:16])=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:6]=1O)C(C)=O.[C:20](=[O:23])([O-])[O-].[K+].[K+].[C:26](=O)([O-])[O-].[Na+].[Na+]>>[NH2:1][C:5]1[C:14]2[C:9](=[CH:10][C:11]([S:15]([OH:18])(=[O:16])=[O:17])=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:6]=1[O:23][CH2:20][CH3:26]

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 133359N-Acetyl-(1-amino-2-naphthol-6-sulfonic acid)

Product 1

HCID 2221662-Naphthalenesulfonic acid, 5-amino-6-ethoxy-Yield 190.3%

Conditions

Temperature
120 °C

Procedure

6.42 kg (62% pure=4 kg of 100% pure) of 1-acetamino-2-hydroxy-naphthalene-6-sulphonic acid, prepared according to Example 4, 0.98 kg of potassium carbonate and 0.75 kg of sodium carbonate are introduced into a 150 l autoclave. After flushing the autoclave with nitrogen, 22 kg (28 l) of ethanol are added to the mixture. The autoclave is closed and heated to 120° C., whilst stirring thoroughly. 7 kg (6.5 l) of 2 N potassium hydroxide solution and 2.75 kg (about 3 l) of ethyl chloride are now pumped into the autoclave in the course of 1 to 2 hours. The entire reaction mixture is stirred for a further 5 hours at 120° C. After cooling the reaction mixture to room temperature, the autoclave is let down and flushed twice with nitrogen. The contents of the autoclave are then introduced into a 250 ml V4A steel kettle. The autoclave is rinsed out with 5 kg of 80% pure ethanol and the rinsing solution is likewise introduced into the steel kettle. The mixture in the steel kettle is heated to the boiling point, about 20 kg of alcohol being distilled off. 13 kg of water are then allowed to run slowly into the boiling solution and the mixture is distilled until no further alcohol passes over. After adding 4.3 kg of 50% strength sodium hydroxide solution, the mixture is stirred at 100° C. for 4 hours. The mixture is then cooled to 20° C. and the product which has precipitated is filtered off and washed with 25 kg of sodium chloride solution. After drying, 3.6 kg of 1-amino-2-ethoxy-naphthalene-6-sulphonic acid (content: 84.2% pure, corresponding to 3.03 kg of 100% pure=80% of theory, relative to 1-acetamino-2-hydroxy-naphthalene-6-sulphonic acid, or 61.6% of theory, relative to 2-hydroxy-naphthalene-6-sulphonic acid) are obtained.

Workup

  1. additionare introduced into a 150 l autoclave
  2. customAfter flushing the autoclave with nitrogen, 22 kg (28 l) of ethanol
  3. additionare added to the mixture
  4. customThe autoclave is closed
  5. customare now pumped into the autoclave in the course of 1 to 2 hours
  6. customThe entire reaction mixture
  7. stirringis stirred for a further 5 hours at 120° C
  8. temperatureAfter cooling the reaction mixture to room temperature
  9. customflushed twice with nitrogen
  10. additionThe contents of the autoclave are then introduced into a 250 ml V4A steel kettle
  11. washThe autoclave is rinsed out with 5 kg of 80% pure ethanol
  12. additionthe rinsing solution is likewise introduced into the steel kettle
  13. temperatureThe mixture in the steel kettle is heated to the boiling point, about 20 kg of alcohol being
  14. distillationdistilled off
  15. distillationthe mixture is distilled until no further alcohol
  16. additionAfter adding 4.3 kg of 50% strength sodium hydroxide solution
  17. stirringthe mixture is stirred at 100° C. for 4 hours
  18. temperatureThe mixture is then cooled to 20° C.
  19. customthe product which has precipitated
  20. filtrationis filtered off
  21. washwashed with 25 kg of sodium chloride solution
  22. customAfter drying

Sources & evidence

ORD record
ord-eb52754ee2054f9da5eec02404b99ea2
Source dataset
uspto-grants-1982_07
Patent number
US04341719

Reaction notes

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