Carbon Dioxide → 5-Aminosalicylic Acid

HRID 2176715Notes

Reaction equation

HRID 2176715 reaction equation
[NH:1]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)C(C)=O.[OH-].[Na+].[O-2].[Al+3].[O-2].[O-2].[Al+3].[C:19](=[O:21])=[O:20]>>[NH2:1][C:5]1[CH:6]=[C:7]([C:19]([OH:21])=[O:20])[C:8]([OH:11])=[CH:9][CH:10]=1

Participants

5

Reactant 4

HCID 280Carbon DioxideHCID 1983AcetaminophenHCID 14798Sodium HydroxideHCID 9989226Alumina

Product 1

HCID 40755-Aminosalicylic AcidYield 75%

Conditions

Temperature
170 °C

Procedure

p-Acetaminophenol 15 g, sodium hydroxide 22.5 g, and aluminum oxide 15 g were added into a 500 ml autoclave, and CO2 was introduced to perform a carboxylation reaction under a reaction pressure of 3.0 MPa and heated to 170° C., maintained for 3 hours, then the reaction was terminated, cooled to 80° C., and 1500 ml distilled water was added to dissolve sodium 5-aminosalicylate. After decolorization, the aqueous phase was acidified with 20˜30% nitric acid until pH=4, cooled and then filtered to obtain the product of 5-aminosalicylic acid, the content is 97% and the yield is 75%.

Workup

  1. additionwas introduced
  2. customa carboxylation reaction
  3. customunder a reaction pressure of 3.0 MPa
  4. temperaturemaintained for 3 hours
  5. customthe reaction was terminated
  6. temperaturecooled to 80° C.
  7. distillation1500 ml distilled water
  8. additionwas added
  9. dissolutionto dissolve sodium 5-aminosalicylate
  10. temperaturecooled
  11. filtrationfiltered

Sources & evidence

ORD record
ord-79ff60893f914763baf1ccb9c0916f9b
Source dataset
uspto-grants-2015_06
Patent number
US09067867B2

Reaction notes

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