Reaction #3850

Reaction equation

ethylene oxide

neodecanoic acid

→

ethylene glycol mononeodecanoate

Solvents

Conditions

Workup

1. 1
   Temperatureheater, cooling coils, automatic temperature controller
2. 2
   Othera gaseous N2 purge of the reactor
3. 3
   workup.ADDITIONis introduced
4. 4
   Otherto remove both oxygen and water
5. 5
   TemperatureWith continued N2 purging its temperature of the neo acid/catalyst solution is gradually raised to 150° C
6. 6
   Otherthe N2 purge
7. 7
   Otherthe reactor vents are sealed
8. 8
   workup.ADDITIONEthylene oxide is then slowly added to the reactor
9. 9
   Temperatureto maintain a reactor pressure of about 30 psig
10. 10
    workup.ADDITIONTotal reaction time, from the start of ethylene oxide addition
11. 11
    workup.WAITis about 55 minutes
12. 12
    Othera gaseous nitrogen purge
13. 13
    workup.ADDITIONis introduced
14. 14
    Temperaturethe reaction product is cooled to room temperature

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.

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