Sulfuric Acid → Bis(9,10-dioxo-9,10-dihydroanthracene-1-diazonium) sulfate
Reaction equation
[N:1]([O-])=O.[Na+].[NH2:5][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.[S:22](=[O:26])(=[O:25])([OH:24])[OH:23]>>[S:22]([O-:26])([O-:25])(=[O:24])=[O:23].[C:6]1([N+:5]#[N: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.[C:6]1([N+:5]#[N: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]=1Participants
Conditions
- Temperature
- 50 °C
Procedure
To 150 cc of concentrated sulphuric acid were added under stirring 17 g of sodium nitrite over a period of 15 minutes. After a homogeneous solution had been obtained, there were added to it over a period of 1 hour 50 g of 1-aminoanthraquinone, maintaining the temperature at 30°-35° C. Thereupon, this mass was heated up to 50° C. for about 20 minutes; the homogeneous solution was then cooled down to 30° C. and poured slowly over 350 g of ice. The precipitated diazonium salt was then filtered, well squeezed out, washed with 30 cc of water and then again squeezed out. Thereby were obtained 120 g of humid anthraquinone-1-diazonium sulphate, which were added under stirring to a solution of 79 g of methacrylonitrile in 300 cc of methanol.
Workup
- customAfter a homogeneous solution had been obtained
- temperaturemaintaining the temperature at 30°-35° C
- temperaturethe homogeneous solution was then cooled down to 30° C.
- filtrationThe precipitated diazonium salt was then filtered
- washwashed with 30 cc of water
Sources & evidence
- ORD record
- ord-3f4aa5d9a37f4e27ae2d0be5e4e18d00
- Source dataset
- uspto-grants-1977_07
- Patent number
- US04036859
Reaction notes
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