Water → 2(5H)-Furanone

Participants

Reaction Conditions

Reaction Steps

The initial charge was 672 mg (2.6 mmol) of Rh(CO)2acac, 2.25 g (22.3 mmol) of triethylamine and 32.8 g (1.8 mol) of water in 400 ml of dioxane. 8.2 l (0.31 mol) of acetylene were injected at room temperature with stirring to a pressure of 3.6 bar. The pressure was then raised to 200 bar with carbon monoxide. The reaction batch was heated to 120° C., raising the pressure to 248 bar, and subsequently stirred for 2 h. After cooling and reactor decompression, the effluent was worked up by distillation. Based on the amount of acetylene used, 52% of 2(5H)-furanone and 22% of butyrolactone had formed. The bottom product of the distillation, which contained the catalyst, was introduced as an initial charge in 400 ml of dioxane and admixed with 2.25 g (22.3 mmol) of triethylamine and 32.8 g (1.8 mol) of water. 8.2 l (0.31 mol) of acetylene were injected at room temperature to a pressure of 3.6 bar. The pressure was then raised to 200 bar with carbon monoxide. The reaction batch was heated to 120° C., raising the pressure to 248 bar, and subsequently stirred for 2 h. After cooling and reactor decompression, the reactor's effluent was worked up by distillation and the bottom product of the distillation, which contained the catalyst, reused. Altogether this procedure was repeated three times without addition of fresh catalyst. The respective yields of product of value (reported as the sum total of 2(5H)-furanone and butyrolactone) are shown in Table 1.

Provenance & Evidence