Sulfuric Acid → 1,3,5,7-Naphthalenetetrasulfonic acid

HRID 1164325Notes

Reaction equation

HRID 1164325 reaction equation
[S:1](=[O:5])(=[O:4])([OH:3])O.[Na+].[Na+].[C:8]1([S:22]([O-:25])(=[O:24])=[O:23])[C:17]2[CH:16]=[CH:15][CH:14]=[C:13]([S:18]([O-:21])(=[O:20])=[O:19])[C:12]=2[CH:11]=[CH:10][CH:9]=1>>[C:8]1([S:22]([OH:25])(=[O:24])=[O:23])[C:17]2[CH:16]=[C:15]([S:1]([OH:5])(=[O:4])=[O:3])[CH:14]=[C:13]([S:18]([OH:21])(=[O:20])=[O:19])[C:12]=2[CH:11]=[C:10]([S:1]([OH:3])(=[O:5])=[O:4])[CH:9]=1

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 74248Disodium 1,5-naphthalenedisulfonate

Product 1

HCID 30152491,3,5,7-Naphthalenetetrasulfonic acid

Procedure

To 100 ml of 30% fuming sulfuric acid at 200° C., is added 25 g of 1,5-naphthalenedisulfonic acid disodium salt. The mixture is refluxed at 180°-185° C. for 18 hours then cooled to 50°-60° C. and filtered, giving 25.6 g of 1,3,5,7-naphthalenetetrasulfonic acid as a tan solid. The entire 25.6 g is added to 200 ml of thionyl chloride and then 2.0 ml of dimethylformamide are added. The mixture is warmed gently until hydrogen chloride is evolved, then heated until bubbling, then allowed to stand at room temperature for 13/4 hours and finally refluxed for 3 hours. The mixture is filtered while warm and the filtrate is evaporated to 20 ml. The solid is collected by filtration and washed with dichloromethane and ether, giving 3.0 g of 1,3,5,7-naphthalenetetrasulfonyl chloride as a colorless powder.

Workup

  1. customat 200° C.
  2. temperatureThe mixture is refluxed at 180°-185° C. for 18 hours
  3. temperaturethen cooled to 50°-60° C.
  4. filtrationfiltered

Sources & evidence

ORD record
ord-69b6a7b6f7114fc399847c8b82af2c3f
Source dataset
uspto-grants-1983_01
Patent number
US04369191

Reaction notes

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