Synthesis of styrene oxide:
Into a 500ml flask with a thermometer was added 30g of styrene, 240ml acetone and 60ml water. The flask was immersed in a cold water bath and magnetic
stirring was applied. A solution of 24.4g TCCA in 100ml acetone was added through an addition funnel at such a rate that the temperature never went
above 30°C. This took about half an hour and a precipitate of cyanuric acid start to form after the first third of TCCA was added. The mixture was
left stirring 45 more minutes and the unreacted TCCA quenched with the addition of 0.5g Na2SO3. Five minutes later, 50ml of 10M aqueous NaOH, was
slowly added drop-wise. The temperature rose from 25 to 32°C and two phases formed. The lower, minor one was a white slurry while the upper acetone
solution was clear. After stirring for an additional 1:30h the upper phase was separated by decantation. It was then washed with 50ml brine. The
acetone was distilled off and the remaining mixture distilled under the vacuum of an aspirator. At about 50°C water with a few drops of the product
that steam distilled came over, followed by the product at 100-140°C. Some yellow gelatinous side product remained in the flask. The distillate was
dried over Na2SO4. It was slightly denser than water, clear, with a slightly sweet smell without any residual styrene smell and amounted to 25.15g
(73%). The IR spectrum is identical to the published for styrene oxide. |
