Previously we have studied on the preparation of terephtalic acid by the oxidation of p-cymene and p-sec-butyltoiuene and obtained acetophenone derivates as the by-products. The compounds obtained were p-methyl-acetophenone, p-isopropylacetophenone and p-diacetylbenzene. These compounds may be converted to the corresponding vinyl compounds by the hydrogenation, being followed by dehydration.
p-Alkylacetophenone, such as p-methyl-, p-ethyl-, p-isopropyl-and p-sec-butyl-acetophenones were synthesized by the method described in Organic Synthesis. These compounds were then hydrogenated with copper-chromite catalyst at 130-465°C and under an initial hydrogen pressure of 100 atm, the hydrogenation being completed after two hours.
The dehydration of fhe carbinol compounds obtained was carried out by the two methods, the one by the use of alumina, the other by potassium bisulfate. In the case of alumina, the temperature used was 300°C and the pressure 30-100mmHg, whereas in the case of potassium bisulfate, the temperature 180-210°C and pressure 100mmHg.
The yields of p-alkylstyrene were 67-91%.
The chemical structure of the p-alkystyrene was confirmed by the use of infra-red spectrum.
View full abstract