Sulfuric Acid → 3-Amino-1,5-naphthalenedisulfonic acid

HRID 838914Notes

Reaction equation

HRID 838914 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:18]([OH:21])(=[O:20])=[O:19])[C:7]2[CH:8]=[CH:9][CH:10]=[C:11]([S:14]([OH:17])(=[O:16])=[O:15])[C:12]=2[CH:13]=1)([O-])=O.S(=O)(=O)(O)O.C([O-])=O.[Na+]>[Pd].O>[NH2:1][C:4]1[CH:5]=[C:6]([S:18]([OH:21])(=[O:20])=[O:19])[C:7]2[CH:8]=[CH:9][CH:10]=[C:11]([S:14]([OH:17])(=[O:16])=[O:15])[C:12]=2[CH:13]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 670321,5-Naphthalenedisulfonic acid, 3-nitro-HCID 2723810Sodium Formate2×

Product 1

HCID 85633-Amino-1,5-naphthalenedisulfonic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

A solution of 20.6 parts of the magnesium salt of 3-nitronaphthalene-1,5-disulphonic acid and 5.5 parts of sulphuric acid in 160 parts of water is reacted with 20.4 parts of sodium formate and 1.24 parts (dry weight) of 3% palladium-on-carbon catalyst according to the procedure of Example 1. After 22 hours a further 10 parts of sodium formate are added and stirring under reflux is continued for an additional period of 20 hours. The mixture is cooled and filtered and the filter cake is washed with dilute sulphuric acid until only the catalyst remains on the filter. Analysis of the combined filtrates by ultraviolet spectroscopy and by titration of an aliquot with sodium nitrite solution indicates that the theoretical yield (17.6 parts) of 3-aminonaphthalene-1,5-disulphonic acid has been formed.

Workup

  1. temperatureunder reflux
  2. temperatureThe mixture is cooled
  3. filtrationfiltered
  4. washthe filter cake is washed with dilute sulphuric acid until only the catalyst

Sources & evidence

ORD record
ord-9a10cfa3e18a48a693d4047f8b6caea8
Source dataset
uspto-grants-1978_06
Patent number
US04093646

Reaction notes

Loading…