Acetic Acid → Diacetoxy-butene

Participants

Reaction Conditions

Reaction Steps

Another run was conducted according to the instant invention using the same apparatus as employed in the runs of Example I. In this run, the reactor was charged with 2.5 grams (20 mmol) of molybdenum dioxide (MoO2), 6.5 grams (75 mmol) of lithium bromide, 4.6 grams (22.5 mmol) of 1,4-dibromo-2-butene, 50 ml of acetic acid, 25 ml of acetic anhydride and 10.9 grams (201.8 mmol) of butadiene from the vapor phase. The reactor was pressured to 30 psig with oxygen, placed in an oil bath and heated to 140° C. As in the runs of Example I, the reactor was pressured intermittently with oxygen to 120 psig. The reactor required about 30 minutes to reach the 140° C. reaction temperature after which the reaction was conducted for 4.75 hours. At the end of the reaction period, the reactor was vented and the solid materials separated by filtration. The filtrate was distilled to remove acetic acid. The distillation residue was then mixed with ether and water, and the layers were separated. The aqueous layer was extracted with ether, and the combined ether extracts were filtered, washed with water, neutralized with a sodium carbonate solution, and dried over magnesium sulfate. The ether solution was then filtered and the ether removed on a rotary evaporator. There remained 13.5 grams of a dark oil which was analyzed by gas-liquid phase chromatography. The analysis showed that there was obtained 9.3 mmol of 1,2-diacetoxy-3-butene and 31.8 mmol of 1,4-diacetoxy-2-butene for a diacetoxy-butene yield of 20 percent based on the butadiene charged.

Provenance & Evidence