Nitric Acid → 1-Nitroanthraquinone
Reaction equation
[CH:1]1[C:14]2[C:13](=[O:15])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6](=[O:16])[C:5]=2[CH:4]=[CH:3][CH:2]=1.[N+:17]([O-])([OH:19])=[O:18]>>[N+:17]([C:8]1[C:7]2[C:6](=[O:16])[C:5]3[C:14](=[CH:1][CH:2]=[CH:3][CH:4]=3)[C:13](=[O:15])[C:12]=2[CH:11]=[CH:10][CH:9]=1)([O-:19])=[O:18]Participants
Procedure
208 g of anthraquinone are introduced into 955 g of 99% nitric acid (mole ratio 15:1) with stirring at room temperature without cooling. When a temperature of 55° is reached, the reaction is continued isothermally until the total reaction time is about 9 minutes. The reaction is then stopped by rapid removal of 376 g of 99% nitric acid by distillation (95.5% nitric acid, γHNO3 = 0.779). Crystallisation is then started by slowly adding 1147 g of 70% nitric acid (crystallisation acid 78.1%, γHNO3 = 0.492). The precipitated product is filtered off, briefly washed with dilute nitric acid, freed from nitric acid adhering to it by evaporation under vacuum and then fractionally distilled at 7 Torr with a head temperature of 275° C. 169.5 g of 98.5% pure 1-nitroanthraquinone (66% of the theoretical amount) are obtained.
Workup
- temperaturewithout cooling
- customa temperature of 55°
- customThe reaction is then stopped by rapid removal of 376 g of 99% nitric acid by distillation (95.5% nitric acid, γHNO3 = 0.779)
- customCrystallisation
- additionby slowly adding 1147 g of 70% nitric acid (crystallisation acid 78.1%, γHNO3 = 0.492)
- filtrationThe precipitated product is filtered off
- washbriefly washed with dilute nitric acid
- customfreed from nitric acid adhering to it by evaporation under vacuum
- distillationfractionally distilled at 7 Torr with a head temperature of 275° C
Sources & evidence
- ORD record
- ord-f4546b9018c8420ba08bc5cb2e43aa68
- Source dataset
- uspto-grants-1977_06
- Patent number
- US04031116
Reaction notes
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