Oxygen → 2-Butene-1,4-diol diacetate

Participants

Reaction Conditions

Reaction Steps

Another run was conducted according to the instant invention employing the same apparatus as that used in Example I. In this run, the reactor was charged with 7.6 grams (75 mmols) of lithium acetate dihydrate, 6.7 grams (40 mmols) of silver acetate, 50 ml of acetic acid, 25 ml of acetic anhydride, and 11.5 grams (213 mmols) of butadiene charged from the vapor phase. The reactor was placed in an oil bath, pressured to 30 psig with oxygen and heated to 140° C. About one hour was required to bring the temperature of the oil bath up to the desired reaction temperature. During the reaction period of 6.8 hours, the reactor was intermittently pressured with oxygen to 120 psig. At the end of the reaction period, the reactor was vented and there was collected 0.5 grams of unreacted butadiene in a cold trap. The reaction mixture was filtered to recover 4.3 grams of white solid. The filtrate was transferred to a distilling flask and the acetic acid removed by distillation at 75 mm mercury pressure. The distillation residue was taken up in ether, filtered through diatomaceous earth, washed with water, washed with a sodium carbonate solution and then dried over magnesium sulfate and filtered. The ether was removed on a rotary evaporator. The residue remaining weighed 18.2 grams and was analyzed by gas-liquid phase chromatography (GLC). The analysis showed that there was obtained 11.15 grams (64.8 mmols) of 1,2-diacetoxy-3-butene and 3.42 grams (19.9 mmols) of 1,4-diacetoxy-2-butene for a yield of diacetoxybutenes of 40 percent based on the butadiene charged.

Provenance & Evidence