Ethylene → 2-Bromobutanoic acid

Participants

Reaction Steps

136 g of methylbromacetate and 3.5 g of azo-bis-isobutyronitrile are charged at 20° C. into a rotary stainless steel autoclave of capacity 0.27 lit provided with a heating jacket and a thermocouple, after which ethylene is added with stirring until the pressure in the autoclave reaches 40 gage atm. Then, within 20 minutes, the temperature in the autoclave is brought to 100° C., and the stirring is carried on at the latter temperature until the pressure ceases to drop, which takes approximately 2 to 3 hours. The remaining ethylene is allowed to escape. The telomerizate (129 g) is subjected to fractional distillation under vacuum, the unreacted methylbromacetate (101 g) being distilled off at a temperature of 80 to 83° C. and a residual pressure of 80 mm Hg. The remaining telomer mixture (27 g) is subjected to fractional distillation in a fractionating column at a residual pressure of 10 mm Hg to yield 14g of methyl ester of γ -bromobutyric acid (35 percent in terms of the reacted methylbromacetate) having a boiling point of 75° to 78° C./10 mm Hg or 124° C./100 mm Hg. The distillation residue (9 g, or 18 percent in terms of the reacted methylbromacetate) is methyl ester of ε-bromocaproic acid having a boiling point of 116° C./12 mm Hg.

Provenance & Evidence