Sulfuric Acid → 6-Hydroxynaphthalene-2-sulfonic acid
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[OH:11].[S:12](=O)(=[O:15])([OH:14])[OH:13]>>[CH:3]1[C:2]([OH:11])=[CH:1][C:10]2[CH:9]=[CH:8][C:7]([S:12]([OH:15])(=[O:14])=[O:13])=[CH:6][C:5]=2[CH:4]=1Participants
Procedure
In the conventional method for preparing Schaeffer's Salt, 2-naphthol is heated with concentrated sulfuric acid until sulfonation is complete. The temperature and reaction time are controlled to provide a high yield of 2-naphthol-6-sulfonic acid. The sulfonation mass is then drowned in water, the resulting solution is neutralized with sodium hydroxide or sodium carbonate, and the crude Schaeffer's Salt is isolated by filtration. The Schaeffer's Salt thus obtained is not pure enough for commercial use and, therefore, must be purified. The conventional method for doing this is to recrystallize the Schaeffer's Salt by dissolving the crude salt in water, treating the solution with activated carbon and, optionally, filter aids, clarifying the solution by filtration, salting out the Schaeffer's Salt by addition of common salt to the clarified solution, and filtering off the precipitated Schaeffer's Salt. Thus, the conventional recovery and purification of the salt requires many operations, including three filtration steps. The many operations thus involved have a serious adverse effect on the cost of manufacture of Schaeffer's Salt. Not only are there high equipment and labor costs, but product losses due to the several handling operations are also encountered. This processing leaves about 2-3% of the disodium salt of DONS in the product recovered.
Workup
- customThe temperature and reaction time
Sources & evidence
- ORD record
- ord-e5d5f0da73cd4610ac288912e97e63b1
- Source dataset
- uspto-grants-1976_11
- Patent number
- US03994963
Reaction notes
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