Oxygen → 2-Butene-1,4-diol diacetate

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A run was carried out according to the process of this invention by charging a 250 ml Fisher-Porter aerosol compatibility bottle equipped with a magnetic stirred with 4.6 grams (21.5 mmoles) of 1,4-dibromo-2-butene, 3.9 grams (50 mmoles) of lithium nitrate, 4.7 grams (10 mmoles) of bismuth trioxide, 50 ml of acetic acid and 25 ml of acetic anhydride and 10.5 grams (194 mmoles) of butadiene charged in the vapor phase. The reaction vessel was pressured to 30 psig with oxygen, placed in an oil bath and heated to 140° C. About 1 hour was required for the reaction vessel to reach 140° C reaction temperature. Subsequently the reaction was carried out for 5.8 hours during which oxygen was added to the reactor intermittently by pressuring the reactor to 120 psig at about 20 minute intervals. At the end of the reaction period, the reactor was vented, and a black solid material filtered from the reaction mixture. The filtrate was distilled through an 18 inch Vigreaux column to remove acetic acid. The distillation residue was mixed with water and ether, and the aqueous layer extracted several times with ether. The combined ether extracts were washed with water, a sodium carbonate solution, dried over magnesium sulfate, filtered, and the ether removed on a rotary evaporator. The residue remaining weighed 10.0 grams. This residue was analyzed by gas-liquid phase chromatography which indicated that there was obtained 3.14 grams (18.3 mmoles) of 1,2-diacetoxy-3-butene and 3.97 grams (23.1 mmoles) of 1,4-diacetoxy-2-butene for a combined yield of the diacetoxy butenes of 21% based on the butadiene charged. This result demonstrates the operability of the catalyst system of this invention for producing diacyloxy olefins from conjugated diolefin reactants.

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