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ChemicalBook CAS DataBase List 2-Aminonaphthalene-1-sulfonic acid

2-Aminonaphthalene-1-sulfonic acid synthesis

3synthesis methods
2-Hydroxynaphthalene-1-sulfonic acid is heated with a mixture of ammonia and ammonium sulfite in an autoclave at 150 ℃ and 1 MPa for 30 h. The reaction mixture is added to a slurry of lime, and excess ammonia is driven off. Inorganic calcium salts are filtered off at 80℃, and the filtrate is acidified with hydrochloric acid at 40℃ to precipitate Tobias acid in 95 % yield. Care must be taken throughout the process to avoid desulfonation and formation of 2- naphthylamine.
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Yield:-

Reaction Conditions:

with sodium carbonate in water

Steps:

1 EXAMPLE 1
EXAMPLE 1 31.9 g of 1-hydroxy-8-aminonaphthalene-3,6-disulphonic acid are dissolved in 400 ml of water under neutral conditions. At 0° to 5° C., 8.8 ml of trifluorotriazine are added, and the pH is maintained at 4.0 to 4.5 by adding 20% strength sodium carbonate solution. After 5 minutes, 9 g of morpholine are added, and the pH is maintained at 7 using 20% strength sodium carbonate solution. After 15 minutes at 10° C., the reaction is complete. The solution thus obtained of the compound of the formula STR9 is further reacted as follows: A diazonium salt suspension obtained by diazotisation of 22.3 g of 2-aminonaphthalene-1-sulphonic acid prepared in the usual manner is added to the reaction product obtained at 0° to 5° C.

References:

Bayer Aktiengesellschaft US5239063, 1993, A

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