Acrolein → 4,4,4-Trinitrobutyraldehyde
Reaction equation
[N+:1]([CH:4]([N+:8]([O-:10])=[O:9])[N+:5]([O-:7])=[O:6])([O-:3])=[O:2].[CH:11]([CH:13]=[CH2:14])=[O:12]>O>[N+:1]([C:4]([N+:8]([O-:10])=[O:9])([N+:5]([O-:7])=[O:6])[CH2:14][CH2:13][CH:11]=[O:12])([O-:3])=[O:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 9 °C
Procedure
A 12 L three-necked, round-bottom flask with a thermometer, mechanical stirrer, and 1000 ml addition funnel was charged with 6377 g of an 11% aqueous trinitromethane solution (701.5 g; 4.675 mol) and cooled in a dry-ice bath at 9° C. A solution of acrolein (274.1 g, 4.90 mol) in 2000 ml of water was added at a rate that maintained the temperature at 0° C. The dry-ice bath was removed and the stirred solution allowed to warm to room temperature overnight. The two phases were separated and the aqueous layer was extracted with CH2Cl2 (2×2000 ml). The combined organic layers were washed with water (2×2000 ml). The product was dried (MgSO4) and concentrated to give 878 g (91%) of the aldehyde as a yellow oil; nD =1.4731 (26C). The infrared spectrum showed bands at 1725 cm-1 (C=O), 1590, 1300, and 800 cm-1 (NO2).
Workup
- additionA 12 L three-necked, round-bottom flask with a thermometer, mechanical stirrer, and 1000 ml addition funnel
- temperaturemaintained the temperature at 0° C
- customThe dry-ice bath was removed
- temperatureto warm to room temperature overnight
- customThe two phases were separated
- extractionthe aqueous layer was extracted with CH2Cl2 (2×2000 ml)
- washThe combined organic layers were washed with water (2×2000 ml)
- dry with materialThe product was dried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-cac7b9beae004cbfb050c4b209cc78a1
- Source dataset
- uspto-grants-1990_02
- Patent number
- US04900851
Reaction notes
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