Ethylene Glycol → 2-Morpholinoethanol

HRID 2118774Notes

Reaction equation

HRID 2118774 reaction equation
[CH2:1]([OH:4])[CH2:2]O.[NH:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1>>[OH:8][CH2:7][CH2:6][N:5]1[CH2:2][CH2:1][O:4][CH2:9][CH2:10]1.[O:8]1[CH2:9][CH2:10][N:5]([CH:6]([N:5]2[CH2:2][CH2:1][O:4][CH2:9][CH2:10]2)[CH3:7])[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 174Ethylene GlycolHCID 8083Morpholine2×

Product 2

HCID 611632-MorpholinoethanolYield 93%HCID 15930829HCID 15930829, compoundYield 3%

Conditions

Temperature
180 °C

Procedure

A 22 ml stainless steel Parr bomb reactor was charged with 5.5 g ethylene glycol (88.6 mol), 1.01 g morpholine (11.5 mol), 130 mg RuCl3 (PPh3)3 (1.3×10-4 mol) 250 mg PPh3 (9.5×10-4 mol) 0.52 g N-methylpyrrolidinone (as internal standard) and a magnetic stirring bar in a nitrogen-filled glove box. The bomb was sealed and placed in a previously-heated oil bath with stirring. After heating for 2.5 h at 180° C., the reactor pressure was 44 psig. At this point, the bomb was cooled to room temperature at which point the pressure stood at 17 psig. The reactor was vented, opened and the contents analyzed by GLC. The analysis showed that all of the morpholine had reacted to give 1.42 g hydroxyethylmorpholine (93% yield) and 0.04 g bismorpholinoethane (3% yield).

Workup

  1. additionfilled glove box
  2. customThe bomb was sealed
  3. customplaced in a previously-heated oil bath
  4. temperatureAt this point, the bomb was cooled to room temperature at which point the pressure
  5. customhad reacted

Sources & evidence

ORD record
ord-de74e23a6c74442eafe6ee9e1bd8e757
Source dataset
uspto-grants-1987_07
Patent number
US04680393

Reaction notes

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