[C:1]([O:5][C:6](=O)[CH2:7][CH3:8])(=[O:4])[CH2:2][CH3:3].[CH2:10](N(CC)CC)C.[C:17]([OH:21])(=[O:20])[CH2:18][CH3:19].O1CC1C=C>COCCOCCOC>[C:17]([O:21][CH:7]([CH2:6][O:5][C:1](=[O:4])[CH2:2][CH3:3])[CH:8]=[CH2:10])(=[O:20])[CH2:18][CH3:19]A 100-mL autoclave was charged with 57.2 g (0.44 mol) propionic anhydride, 1.62 g (0.016 mol) of triethylamine, 1.2 g (0.016 mol) of propionic acid and 3.44 g of diglyme. The autoclave was purged with helium twice, then the vessel was pressurized to 6.2 bars (75 psig) with helium followed by agitation. The reaction mixture was heated to 125° C., then 31.35 mL (0.40 mol) of 3,4-epoxy-1-butene was introduced to the reactor via syringe pump over 10 seconds. A first sample was taken at 1 min, then sequential samples were obtained every 15 min during the course of 2 hrs for analysis by GC. GC analysis of the crude mixture after 2 hrs revealed a 90% yield of 3,4-dipropionyloxy-1-butene with a 91% selectivity and 6% 3,4-epoxy-1-butene. The reaction was observed to be first order in 3,4-epoxy-1-butene with a first order rate constant of 0.017 min-1 (Table A). This example shows the use of another carboxylic anhydride with its conjugate carboxylic acid.
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