3,3'-(Ethane-1,2-diylbis(oxy))dipropanenitrile

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Small scale: Ethylene glycol (1 g, 16.1 mmol) was mixed with Triton B (40% in MeOH, 0.22 g, 0.53 mmol) and cooled in an ice-bath while acrylonitrile (1.71 g, 32.2 mmol) was added. The mixture was stirred at room temperature for 60 hours after which it was neutralized with 0.1 M HCl (0.6 cm3) and extracted with CH2Cl2 (80 cm3) The extracts were concentrated under reduced pressure and the residue was Kugelrohr-distilled to give 3,3′-(ethane-1,2-diylbis(oxy))dipropanenitrile (1.08 g, 39.9%) as a light colored oil, bp 150-170° C./20 Torr. was added extracted with CH2Cl2 (80 cm3) The extracts were concentrated under reduced pressure the residue was Kugelrohr-distilled

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Small scale: Ethylene glycol (1 g, 16.1 mmol) was mixed with Triton B (40% in MeOH, 0.22 g, 0.53 mmol) and cooled in an ice-bath while acrylonitrile (1.71 g, 32.2 mmol) was added. The mixture was stirred at room temperature for 60 hours after which it was neutralized with 0.1 M HCl (0.6 cm3) and extracted with CH2Cl2 (80 cm3) The extracts were concentrated under reduced pressure and the residue was Kugelrohr-distilled to give 3,3′-(ethane-1,2-diylbis(oxy))dipropanenitrile (1.08 g, 39.9%) as a light colored oil, bp 150-170° C./20 Torr. was added extracted with CH2Cl2 (80 cm3) The extracts were concentrated under reduced pressure the residue was Kugelrohr-distilled

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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 (30.6 moles) of acrylonitrile (N≡C-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 with saturated NaCl solution three times, the product was separated from the aqueous layer, dried over CaCl2 and passed through an Al2O2 column to insure that all basic materials had been removed. The yield obtained was 90% of theoretical. was kept below 35° C After the addition was stirred an additional hour After washing with saturated NaCl solution three times the product was separated from the aqueous layer dried over CaCl2 had been removed The yield obtained

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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 (30.6 moles) of acrylonitrile (N≡C-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 with saturated NaCl solution three times, the product was separated from the aqueous layer, dried over CaCl2 and passed through an Al2O2 column to insure that all basic materials had been removed. The yield obtained was 90% of theoretical. was kept below 35° C After the addition was stirred an additional hour After washing with saturated NaCl solution three times the product was separated from the aqueous layer dried over CaCl2 had been removed The yield obtained

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 5 liter double walled (for water cooling) glass reactor with a bottom drain and stopcock was charged 930 grams (15 moles) of ethylene glycol and 45.6 grams of 40% aqueous KOH solution. Some 1620 grams (30.6 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 with 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. was kept below 35° C After the addition was stirred an additional hour After washing with saturated NaCl solution three times the product was separated from the aqueous layer dried over CaCl2 had been removed The yield obtained

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 5 liter double walled (for water cooling) glass reactor with a bottom drain and stopcock was charged 930 grams (15 moles) of ethylene glycol and 45.6 grams of 40% aqueous KOH solution. Some 1620 grams (30.6 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 with 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. was kept below 35° C After the addition was stirred an additional hour After washing with saturated NaCl solution three times the product was separated from the aqueous layer dried over CaCl2 had been removed The yield obtained

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Small scale: Ethylene glycol (1 g, 16.1 mmol) was mixed with Triton B (40% in MeOH, 0.22 g, 0.53 mmol) and cooled in an ice-bath while acrylonitrile (1.71 g, 32.2 mmol) was added. The mixture was stirred at room temperature for 60 hours after which it was neutralized with 0.1M HCl (0.6 cm3) and extracted with CH2Cl2 (80 cm3). The extracts were concentrated under reduced pressure and the residue was Kugelrohr-distilled to give 3,3′-(ethane-1,2-diylbis(oxy))dipropanenitrile (1.08 g, 39.9%) as a light coloured oil, by 150-170° C./20 Torr. was added extracted with CH2Cl2 (80 cm3) The extracts were concentrated under reduced pressure the residue was Kugelrohr-distilled

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Small scale: Ethylene glycol (1 g, 16.1 mmol) was mixed with Triton B (40% in MeOH, 0.22 g, 0.53 mmol) and cooled in an ice-bath while acrylonitrile (1.71 g, 32.2 mmol) was added. The mixture was stirred at room temperature for 60 hours after which it was neutralized with 0.1M HCl (0.6 cm3) and extracted with CH2Cl2 (80 cm3). The extracts were concentrated under reduced pressure and the residue was Kugelrohr-distilled to give 3,3′-(ethane-1,2-diylbis(oxy))dipropanenitrile (1.08 g, 39.9%) as a light coloured oil, by 150-170° C./20 Torr. was added extracted with CH2Cl2 (80 cm3) The extracts were concentrated under reduced pressure the residue was Kugelrohr-distilled

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Small scale: Ethylene glycol (1 g, 16.1 mmol) was mixed with Triton B (40% in MeOH, 0.22 g, 0.53 mmol) and cooled in an ice-bath while acrylonitrile (1.71 g, 32.2 mmol) was added. The mixture was stirred at room temperature for 60 hours after which it was neutralized with 0.1M HCl (0.6 cm3) and extracted with CH2Cl2 (80 cm3). The extracts were concentrated under reduced pressure and the residue was Kugelrohr-distilled to give 3,3′-(ethane-1,2-diylbis(oxy))dipropanenitrile (1.08 g, 39.9%) as a light coloured oil, by 150-170° C./20 Torr. was added extracted with CH2Cl2 (80 cm3) The extracts were concentrated under reduced pressure the residue was Kugelrohr-distilled

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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. was kept below 35° C After the addition was stirred an additional hour The mixture was then neutralized to a pH of 7 by the addition of 6 molar HCL After washing the product was separated from the aqueous layer dried over CaCl2 had been removed The yield obtained

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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. flask fitted with a stirrer reflux condensor and an additional funnel immersed in an ice water bath was added 248 g of the reaction mixture was withdrawn from the flask This run was performed with gradual addition of acrylonitrile

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Small scale: Ethylene glycol (1 g, 16.1 mmol) was mixed with Triton B (40% in MeOH, 0.22 g, 0.53 mmol) and cooled in an ice-bath, while acrylonitrile (1.71 g 32.2 mmol) was added. The mixture was stirred at room temperature for 60 hours after which it was neutralized with 0.1 M HCl (0.6 cm3) and extracted with CH2Cl2 (80 cm3). The extracts were concentrated under reduced pressure, and the residue was Kugelrohr-distilled to give 3,3′-(ethane-1,2-diylbis(oxy))dipropanenitrile (1.08 g, 39.9%) as a light coloured oil, bp 150-170° C./20 Torr. was added extracted with CH2Cl2 (80 cm3) The extracts were concentrated under reduced pressure the residue was Kugelrohr-distilled