Epichlorohydrin → Diglycidyl ether

The reaction product of (a), 1 liter of epichlorohydrin and 20 gm of benzyltrimethylammonium chloride (BTMAC) dissolved in 12 ml of water are charged to a 2 liter 3-neck round bottom flask equipped with a mechanical stirrer, thermometer, thermoregulator, condenser, Dean-Stark Trap and dropping funnel. The mixture is then heated to about 50° to 55° C. at high vacuum of 70 torr with stirring resulting in a vigorous reflux of the epichlorohydrin. 109 gm of NaOH (50% solution) is slowly added to the mixture over a period of 2 hours. The water/epichlorohydrin mixture is removed by distillation as soon as the azeotrope is formed. Upon completion of the addition, the epichlorohydrin is returned to the reaction mixture and the reaction is allowed to continue for an additional 1.5 hours. The reaction mixture is then cooled to room temperture and washed with 300 ml of ice water and separated. The organic layer is then washed with another 300 ml of water and the pH adjusted to about 5-6 using 10% aqueous acetic acid. The organic layer is then washed a third time with 300 ml of water and separated. The epichlorohydrin is then removed by distillation at reduced pressure (from 70 to 2 torr). The final distillation condition about less than 5 torr/110° C. The distillation is continued until no volatile could be distilled to ensure the complete removal of the epichlorohydrin. The yield is 330 gm. The epoxy value is 0.306 eq/100 g and the viscosity is 1310 cps at 25° C.

1. additionare charged to a 2 liter 3-neck round bottom flask
2. customequipped with a mechanical stirrer
3. temperatureThe mixture is then heated to about 50° to 55° C. at high vacuum of 70 torr
4. customresulting in
5. customThe water/epichlorohydrin mixture is removed by distillation as soon as the azeotrope
6. customis formed
7. additionUpon completion of the addition
8. temperatureThe reaction mixture is then cooled to room temperture
9. washwashed with 300 ml of ice water
10. customseparated
11. washThe organic layer is then washed with another 300 ml of water
12. washThe organic layer is then washed a third time with 300 ml of water
13. customseparated
14. customThe epichlorohydrin is then removed by distillation at reduced pressure (from 70 to 2 torr)
15. distillationThe final distillation condition about less than 5 torr/110° C
16. distillationThe distillation
17. distillationcould be distilled
18. customthe complete removal of the epichlorohydrin
19. customat 25° C.

ORD record

ord-1d08240e418848ceb73337d748348b0d

Source dataset

uspto-grants-1992_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05117010