Ethylene Oxide → 2-Hydroxyethylneodecanoate

HRID 3754

Reaction equation

HRID 3754 reaction equation
[CH2:1]1[O:3][CH2:2]1.[C:4]([OH:15])(=[O:14])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([CH3:13])([CH3:12])[CH3:11]>>[C:4]([O:15][CH2:1][CH2:2][OH:3])(=[O:14])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([CH3:11])([CH3:12])[CH3:13]

Participants

3

Reactant 2

HCID 6354Ethylene OxideHCID 62838Versatic 10

Product 1

HCID 201530382-Hydroxyethylneodecanoate

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 neodecanoic 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 to maintain a reactor pressure of about 30 psig. 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 mononeodecanoate product mixture thereby obtained was analyzed by gas chromatography. The data obtained are set forth in Table II below.

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
  9. temperatureto maintain a reactor pressure of about 30 psig
  10. additionTotal reaction time, from the start of ethylene oxide addition
  11. waitis about 55 minutes
  12. customa gaseous nitrogen purge
  13. additionis introduced
  14. temperaturethe reaction product is cooled to room temperature

Sources & evidence

ORD record
ord-d50e6d173a8247479425da3781712173
Source dataset
uspto-grants-1988_02
Patent number
US04722811

Linked notes

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