Hydroquinone → Decyl methacrylate

Participants

Reaction Steps

To a 1 liter flask equipped with an agitator, thermometer and a Vigreux fractionating column were added 188 g (1.88 mol) of methyl methacrylate (MMA), 59.4 g (0.376 mol) of n-decyl alcohol, 1.25 mol % of zinc acetylacetonate, 1.25 mol % of LiCl and 0.75 g of phenothiazine, and 0.62 g of hydroquinone free radical polymerization inhibitor. The mixture was heated to reflux at atmospheric pressure while an azeotropic mixture of MMA and methanol was removed from the upper part of the fractionation column. The reaction was continued in this manner for approximately five hours. After vacuum filtration of the catalyst and inhibitors, the excess of MMA was removed under vacuum and the resulting n-decyl methacrylate (DMA) was isolated (84.3 grams, 99.1% yield) and analyzed. Gas-liquid chromatographic (GLC) analysis showed 99% conversion of 1-decanol to DMA of 98% purity.

Provenance & Evidence