Diglyme → 3,4-Dipropionyloxy-1-butene

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A 100-mL autoclave was charged with 57.2 g (0.44 mol) propionic anhydride, 1.62 g (0.016 mol) of triethylamine 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 an 84% yield of 3,4-dipropionyloxy-1-butene with a 94% selectivity and 11.2% 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 triethylamine and no carboxylic acid co-catalyst.

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