Ethylene → Ethylene glycol mononeononanoate

HRID 3753

Reaction equation

HRID 3753 reaction equation
[CH2:1]1[O:3][CH2:2]1.[C:4]([OH:14])(=[O:13])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]([CH3:12])([CH3:11])[CH3:10].C=C>>[C:4]([O:14][CH2:1][CH2:2][OH:3])(=[O:13])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]([CH3:10])([CH3:11])[CH3:12]

Participants

4

Reactant 3

HCID 6325EthyleneHCID 6354Ethylene Oxide8×HCID 6453798Neononanoic acid

Product 1

HCID 14150111Ethylene glycol mononeononanoate

Conditions

Temperature
100 °C

Procedure

To a one liter stainless steel autoclave, equipped with a mechanical stirrer, heater, cooling coils, automatic temperature controller, and a tared ethylene oxide cylinder, in a series of runs is added 500 grams neononanoic acid and 2.0 g of the selected catalyst. The reactor is heated to approximately 100° C. and a gaseous N2 purge of the reactor is introduced to remove both oxygen and water. With continued N2 purging its temperature of the neo acid/catalyst solution is gradually raised to 150° C. Upon reaching temperature, the N2 purge is stopped and the reactor vents are sealed. Ethylene oxide is then slowly added to the reactor until a pressure of 60 psig is obtained. The ethylene oxide flow is then stopped. As the reaction between the neo acid and the ethylene proceeds, the pressure of the reactor vessel will slowly decrease. When the pressure reaches 20 psig, ethylene oxide is again slowly charged to the reactor until a pressure of 60 psig is obtained. The ethylene oxide flow is then decreased to the point where a steady reactor pressure of 60 psig is obtained. The addition of ethylene oxide continues until the desired quantity of ethylene oxide has been added to the reaction. The flow of ethylene oxide is then stopped. The reaction mixture is stirred for an additional 20 minutes, until the reactor pressure decreases to 15 psig. Total reaction time, from the start of ethylene oxide addition is about 55 minutes. The reactor is then vented, a gaseous nitrogen purge is introduced, and the reaction product is cooled to room temperature. The crude ethylene glycol mononeononanoate product mixture thereby obtained was characterized by gas chromatography and found to have the following characteristics:

Workup

  1. temperatureheater, cooling coils, automatic temperature controller
  2. customa gaseous N2 purge of the reactor
  3. additionis introduced
  4. customto remove both oxygen and water
  5. temperatureWith continued N2 purging its temperature of the neo acid/catalyst solution is gradually raised to 150° C
  6. customthe N2 purge
  7. customthe reactor vents are sealed
  8. additionEthylene oxide is then slowly added to the reactor until a pressure of 60 psig
  9. customis obtained
  10. customAs the reaction between the neo acid
  11. additionis again slowly charged to the reactor until a pressure of 60 psig
  12. customis obtained
  13. customis obtained
  14. additionhas been added to the reaction
  15. waitis about 55 minutes
  16. customa gaseous nitrogen purge
  17. additionis introduced
  18. temperaturethe reaction product is cooled to room temperature

Sources & evidence

ORD record
ord-acc451c6d71348d3baa782dc1cdfbe6d
Source dataset
uspto-grants-1988_02
Patent number
US04722811

Linked notes

Loading…