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 at 0° with stirring (mole ratio 15:1). The temperature of the reaction mixture rises to 55° in about 6 minutes. This temperature is maintained by cooling until the total reaction time is 10 minutes. 316 g of 99% nitric acid (γHNO3 = 0.791) are then distilled off very rapidly at this temperature under vacuum. 100 ml of water are then slowly added to the sump product (crystallisation acid 82%, γHNO3 = 0.532). The precipitated product is suction-filtered, washed with a little 75% nitric acid and then with water, dried and subjected to fractional vacuum distillation at 10 Torr and a head temperature of 281°. 172.1 g of 98.7% pure 1-nitroanthraquinone (67.1% of the theoretical amount) are obtained as distillate.
Workup
- temperatureThis temperature is maintained
- temperatureby cooling until the total reaction time
- waitis 10 minutes
- distillation316 g of 99% nitric acid (γHNO3 = 0.791) are then distilled off very rapidly at this temperature under vacuum
- addition100 ml of water are then slowly added to the sump product (crystallisation acid 82%, γHNO3 = 0.532)
- filtrationThe precipitated product is suction-filtered
- washwashed with a little 75% nitric acid
- dry with materialwith water, dried
- distillationsubjected to fractional vacuum distillation at 10 Torr
- customa head temperature of 281°
Sources & evidence
- ORD record
- ord-4e9275a3ff674b70a94475219447a45e
- Source dataset
- uspto-grants-1977_06
- Patent number
- US04031116
Reaction notes
Loading…