Potassium Chloride → 2-Chloroanthraquinone

HRID 972041Notes

Reaction equation

HRID 972041 reaction equation
[Cl:1]([O-])(=O)=O.[Na+].[CH:6]1[C:19]2[C:18](=[O:20])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:21])[C:10]=2[CH:9]=[CH:8][C:7]=1S(O)(=O)=O.[Cl-:26].[K+]>O.S(=O)(=O)(O)O>[CH:13]1[C:12]2[C:11](=[O:21])[C:10]3[C:19](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:18](=[O:20])[C:17]=2[CH:16]=[CH:15][CH:14]=1.[Cl:26][C:7]1[CH:8]=[CH:9][C:10]2[C:11](=[O:21])[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:18](=[O:20])[C:19]=2[CH:6]=1.[Cl:1][C:6]1[C:19]2[C:18](=[O:20])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:21])[C:10]=2[CH:9]=[CH:8][CH:7]=1

Participants

8

Reactant 3

HCID 4873Potassium ChlorideHCID 85529,10-Dioxo-9,10-dihydroanthracene-2-sulfonic acidHCID 516902Sodium Chlorate

Product 3

HCID 67091-ChloroanthraquinoneYield 1%HCID 6780AnthraquinoneYield 3%HCID 85532-ChloroanthraquinoneYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Conditions

Temperature
100 °C

Procedure

1,200 l of 10% strength sodium chlorate solution are added in the course of 4 hours to 150 kg of anthraquinone-2-sulphonic acid (Na salt), (produced according to Ullmann, Encyclopadie der technischen Chemie (Encyclopaedia of Industrial Chemistry), 4th Edition, Volume 7, page 589; Bios Final Report 1484) with 90 kg of potassium chloride in 2,745 l of water and 255 l of sulphuric acid (96%) at 100° C. in an enamelled 6 m3 kettle, while stirring (30- 40 revolutions per minute) and the mixture is stirred for a further 5 hours at 100° C. The mixture is filtered at 80° C. through a filter press, the material on the filter is washed with hot water until the filtrate gives a neutral reaction and the filter cake is dried, 2-Chloroanthraquinone of the following composition: about 3% of anthraquinone, about 95% of 2-chloroanthraquinone, about 1% of 1-chloroanthraquinone and about 1% of insoluble matter is obtained.

Workup

  1. custom(produced
  2. filtrationThe mixture is filtered at 80° C. through a filter press
  3. washthe material on the filter is washed with hot water until the filtrate
  4. customgives
  5. customa neutral reaction
  6. customthe filter cake is dried

Sources & evidence

ORD record
ord-00c70d9e25724ac68a1878fbe336383a
Source dataset
uspto-grants-1979_07
Patent number
US04162946

Reaction notes

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