Acrolein → 4,4,4-Trinitrobutyraldehyde

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence