Heptane → Tetradecanoic acid, 2-[4-[(butylsulfonyl)amino]phenoxy]-, methyl ester

Participants

Reaction Steps

A heel was created batchwise by charging 142.2 g (0.41 moles) of methyl 2-[4-aminophenoxy]tetradecanoate (the amine), 267.7 g of heptane, 45.7 g (0.46 moles) of potassium bicarbonate, and 119.7 g of deionized water. The two-phase mixture was stirred with high agitation (800-900 rpm) and heated to 55° C-60° C. at which point 71.4 g of butanesulfonyl chloride was added over approximately 1 hour. After stirring for one hour, the composition of the assay of the product in the upper organic phase was 98.9%. At this point, continuous feeds into the reactor system, which consists of two reactors and a processing tank, were started to provide six hours of residence time in the two reactors. The feed rates were: 1.46 g/min (2.63 mmoles/min) of the amine solution (63 wt % in heptane), 0.45 g/min (2.87 mmoles/min) of the butanesulfonyl chloride, and 1.42 g/min (2.87 mmoles/min) of a 20 wt % potassium bicarbonate solution.

Provenance & Evidence