1-Butanol → Butyl Methacrylate

An example utilizing an in-situ hafnium catalyst was performed by adding 20.0 g (274 mmol) n-butanol, 135 g (1.35 mole) MMA, 20 mg phenothiazine to a 300 ml round bottom flask equipped with an agitator, thermometer, and Vigreux fractional distillation column. The solution was dehydrated by refluxing the mixture at atmospheric pressure and removing water via a MMA/water azetrope. The mixture was then cooled to 0° C. (ice bath) where 1.63 g (16.1 mmol) triethylamine, 1.0 g (10.0 mmol) 2,4-pentanedione, and 870 mg (2.72 mmol) hafnium tetrachloride were added to the solution. The catalyzed mixture was heated to reflux at 1 atm. pressure while azetropic mixture of MMA and MeOH was removed from the upper part of the fractionating column. The reaction was continued in this manner for approximately 2 hours while the temperature at the top of the column was 65°-67° C. and the temperature in the pot was 97°-112° C. Analysis of the reaction mixture by gas-liquid chromatographic analysis showed greater than 99% conversion of the n-butanol to n-butyl methacrylate.

1. customequipped with an agitator
2. distillationthermometer, and Vigreux fractional distillation column
3. temperatureby refluxing the mixture at atmospheric pressure
4. customremoving water via a MMA/water azetrope
5. additionwere added to the solution
6. temperatureThe catalyzed mixture was heated
7. customwas removed from the upper part of the fractionating column
8. customwas 65°-67° C.
9. custompot was 97°-112° C

ORD record

ord-36392fea3164472292214cdbab28e555

Source dataset

uspto-grants-1991_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05037978