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

HRID 1863357Notes

Reaction equation

HRID 1863357 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].[OH-].[K+].[C:7](#[N:10])[CH:8]=[CH2:9]>O>[CH2:8]([C:7]#[N:10])[CH2:9][O:3][CH2:2][CH2:1][O:4][CH2:9][CH2:8][C:7]#[N:10]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 7855AcrylonitrileHCID 14797Potassium Hydroxide

Product 1

HCID 769213,3'-(Ethylenedioxy)dipropiononitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 5 liter double walled (for water cooling) glass reactor with a bottom drain and stopcock were charged 930 grams (15 moles) of ethylene glycol and 45.6 grams of 40% aqueous KOH solution. Some 1620 grams (30.0 moles) of acrylonitrile (NC--CH=CH2) were then added dropwise, with stirring, at such a rate that the temperature was kept below 35° C. After the addition was completed the mixture was stirred an additional hour and then allowed to stand overnight. The mixture was then neutralized to a pH of 7 by the addition of 6 molar HCL. After washing was saturated NaCl solution three times, the product was separated from the aqueous layer, dried over CaCl2 and passed through an Al2O3 column to insure that all basic materials had been removed. The yield obtained was 90% of theoretical.

Workup

  1. customwas kept below 35° C
  2. additionAfter the addition
  3. stirringwas stirred an additional hour
  4. additionThe mixture was then neutralized to a pH of 7 by the addition of 6 molar HCL
  5. washAfter washing
  6. customthe product was separated from the aqueous layer
  7. dry with materialdried over CaCl2
  8. customhad been removed
  9. customThe yield obtained

Sources & evidence

ORD record
ord-a5c727da489c47d7a81ff6bb5ff2cb32
Source dataset
uspto-grants-1979_09
Patent number
US04168602

Reaction notes

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