Diethyl Ether → Butyl Methacrylate

A 74.1 g (1.0 mole) amount of n-butyl alcohol, 250.2 g (2.5 mols) of methyl methacrylate, 187 g (2.18 mols) of n-hexane and 0.17 g of hydroquinonemonomethyl ether were added to the apparatus described in Example 1 and were heated and agitated under full reflux to remove water from the reaction system. The amount of water obtained in the reaction solution was 0.001 mol. To the reaction solution was added 0.0035 mol of sodium methylate as a catalyst and the solution was heated and agitated. An azeotropic mixture of n-hexane and methanol from the upper part (top) of the fractionating tower was obtained and was kept stationary in a decanter. The n-hexane layer which separated was returned to the tower and the methanol layer was removed continuously to advance the reaction. Meanwhile, the temperature at the top of the tower was 56° to 59.8° C. and the flask temperature was 83° to 90° C. The results of the experiment were a 99.4% conversion of n-butyl alcohol and a 87.3% yield of n-butyl methacrylate. However, it was found by gas chromatography that an additive of methyl methacrylate was produced as a by-product as well as a polymer. As soon as this reaction solution was distilled, it polymerized.

1. temperaturewere heated
2. temperatureunder full reflux
3. customto remove water from the reaction system
4. customThe amount of water obtained in the reaction solution
5. temperaturethe solution was heated
6. stirringagitated
7. customwas obtained
8. customThe n-hexane layer which separated
9. customthe methanol layer was removed continuously
10. customthe reaction
11. customwas 56° to 59.8° C.
12. customwas 83° to 90° C
13. customThe results of the experiment

ORD record

ord-21ac69a351ae469a98b1a921de922e6e

Source dataset

uspto-grants-1980_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04202990