Salicylic Acid → Aspirin sodium

HRID 1415287Notes

Reaction equation

HRID 1415287 reaction equation
[CH3:1][C:2]([O:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=1[C:11]([OH:13])=[O:12])=[O:3].O.C(=O)([O-])[O-].[Na+:19].[Na+].OS(O)(=O)=O.C(O)(=O)C1C(=CC=CC=1)O>O>[C:2]([O:4][C:5]1[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:11]([O-:13])=[O:12])(=[O:3])[CH3:1].[Na+:19]

Participants

6

Reactant 4

HCID 338Salicylic AcidHCID 1118Sulfuric AcidHCID 2244Aspirin2×HCID 2735133Sodium Carbonate Monohydrate

Product 1

HCID 23666729Aspirin sodium

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

An aqueous solution of sodium acetylsalicylate was prepared using 100.0 g. of aspirin, 34.6 g. of sodium carbonate hydrate and 1,425 ml. water at room temperature (25° C.). After solution of all solids had occurred, 30.0 g. of instant tea was added while stirring at room temperature. To the aqueous solution was added with rapid stirring in less than 30 seconds 280 ml. of 2N H2SO4 and stirring was continued for 15 minutes at room temperature. The pH of the reaction after acidification was 3.3. The aqueous slurry was immediately thereafter spray dired in a Nichols portable spray drier (Minor Type 53) using a Nitro atomizer having a rotational speed of 31,000 r.p.m. The operating temperatures were about 165° C. on the inlet side and less 80° C. on the exhaust side. Weight of the spray dried product was 158.5 g. Analysis of the spray dried product containing the coprecipitate showed it contained 55% aspirin, 0.64% salicylic acid and 2.7% water. Tea content of the spray dried product is approximately 18.8%.

Workup

  1. customat room temperature
  2. custom(25° C.)
  3. additionof instant tea was added
  4. additionTo the aqueous solution was added
  5. stirringwith rapid stirring in less than 30 seconds 280 ml
  6. customThe pH of the reaction after acidification
  7. customwere about 165° C. on the inlet side and less 80° C. on the exhaust side
  8. additionAnalysis of the spray dried product containing the coprecipitate

Sources & evidence

ORD record
ord-65d1f1348383429bb713396b98b56e3b
Source dataset
uspto-grants-1977_01
Patent number
US04003999

Reaction notes

Loading…