Ethylene Glycol → 3,3'-(Ethylenedioxy)dipropiononitrile

To a 2000 ml. flask fitted with a stirrer, reflux condensor and an additional funnel and immersed in an ice water bath was added 248 g. of ethylene glycol and 20 g. of 40% aqueous NaOH. The stirrer was started and the 424 g. of acrylonitrile was added from the funnel over a period of about 15 minutes. The temperature remained in the range of 25°-35° C. during the addition of the acrylonitrile. The stirring was continued for one additional hour after which 170 g. of the reaction mixture was withdrawn from the flask and neutralized by contacting with 70 g. of a sulfonic acid resin. The withdrawn mixture contained more than 95 wt. % of 3,3'-ethylenedioxy-bis(propionitrile), and essentially no acrylonitrile. This run was performed with gradual addition of acrylonitrile to produce the 3,3'-ethylenedioxy-bis(propionitrile) for use in the subsequent run with rapid addition of acrylonitrile.

1. customflask fitted with a stirrer
2. temperaturereflux condensor and an additional funnel
3. customimmersed in an ice water bath
4. additionwas added 248 g
5. customof the reaction mixture was withdrawn from the flask
6. additionThis run was performed with gradual addition of acrylonitrile

ORD record

ord-18ba41596271446db65bbf7e3e7e822e

Source dataset

uspto-grants-1981_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04271089