Sulfuric Acid → Sulfuric Acid

HRID 255845

Reaction equation

HRID 255845 reaction equation
[CH:1]1[CH:6]=[C:5]2[C:7]([OH:18])=[C:8]3[C:13](=[C:14]([OH:15])[C:4]2=[CH:3][CH:2]=1)[C:12]([NH2:16])=[CH:11][CH:10]=[C:9]3[NH2:17].[S:19](=O)(=[O:22])([OH:21])[OH:20].[OH:24][S:25]([OH:28])(=[O:27])=[O:26].O=S(=O)=O>>[NH2:17][C:9]1[C:8]2[C:7](=[O:18])[C:5]3[C:4](=[CH:3][CH:2]=[CH:1][CH:6]=3)[C:14](=[O:15])[C:13]=2[C:12]([NH2:16])=[CH:11][C:10]=1[S:19]([OH:22])(=[O:21])=[O:20].[S:25](=[O:26])(=[O:24])([OH:28])[OH:27]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 214029,10-Anthracenediol, 1,4-diamino-HCID 24681Fuming sulfuric acid2×

Product 2

HCID 1118Sulfuric AcidHCID 777251,4-Diamino-9,10-dihydro-9,10-dioxoanthracene-2-sulphonic acid

Conditions

Temperature
110 °C

Procedure

80 parts of leuco-1,4-diaminoanthraquinone are added to 270 parts of 100% sulfuric acid over 30 minutes, the temperature rising to 65°-70° C. The solution is heated to 110° C. and then 90 parts of 66% oleum are added initially over 1 hour, followed by the dropwise addition of a further 80 parts of 66% oleum over the next 3 hours. The reaction mixture is then stirred for a further 4 hours at 110° C., cooled to room temperature and poured onto 255 parts of ice. The resultant brown suspension is filtered at room temperature, affording crude 1,4-diaminoanthraquinone-2-sulfonic acid which still contains sulfuric acid and is of sufficient purity that it can be used in this form direct for the dye synthesis, especially if the subsequent synthesis is carried out in sulfuric acid in any case.

Workup

  1. customrising to 65°-70° C
  2. temperaturecooled to room temperature
  3. additionpoured onto 255 parts of ice
  4. filtrationThe resultant brown suspension is filtered at room temperature

Sources & evidence

ORD record
ord-b2755a0814a6495095fc04b3db0d7882
Source dataset
uspto-grants-1987_10
Patent number
US04699735

Linked notes

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