Ethyl Acetate → Diethyl vinylphosphonate

Temperature

150 °C

25 g of vinylphosphonic acid and 70 g of diethyl 2-acetoxyethanephosphonate were heated with stirring to 180° C. 252 g of diethyl 2-acetoxyethanephosphonate were then slowly added dropwise over 14 hours while the temperature gradually increased to 200° C. and ethyl acetate distilled off. The mixture was then stirred for 9 hours at 190° C. 190 g of crude monoethyl vinylphosphonate were obtained. Distillation produced 128 g of ethyl acetate and additionally 8 g of light ends which were trapped in a cold trap downstream from the apparatus. 95 g of the crude monoethyl vinylphosphonate and 124 g of triethyl orthoformate were refluxed for 8 hours at about 75° C. The temperature was then gradually increased in the course of 5.5 hours to 150° C. while ethyl acetate and ethanol distilled off. A further 100 g of triethyl orthoformate were then added at room temperature and the mixture was gradually heated again to 150° C. while light ends distilled off. A cold trap downstream from the apparatus collected less that 1 g. The mixture was then distilled and 96.5 g of diethyl vinylphosphonate were obtained. This corresponded to a yield of about 70%, relative to the amount of vinylphosphonic acid and diethyl 2-acetoxyethanephosphonate started with. During the reaction with the orthoester, about 160 g distilled off which contained 28 percent of ethanol and about 10 percent of diethyl ether in addition to about 60 percent of ethyl formate.

1. distillationDistillation
2. customproduced 128 g of ethyl acetate and additionally 8 g of light ends which
3. customwere trapped in a cold trap
4. distillationdistilled off
5. additionA further 100 g of triethyl orthoformate were then added at room temperature
6. distillationdistilled off
7. customA cold trap downstream from the apparatus collected less that 1 g
8. distillationThe mixture was then distilled

ORD record

ord-fc5ce34a0e0b4b629b7f9004b0b07ad7

Source dataset

uspto-grants-1985_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04493803