Ethylene Glycol → HCID 15930829, compound

HRID 1722437Notes

Reaction equation

HRID 1722437 reaction equation
[CH2:1]([OH:4])[CH2:2]O.[NH:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.O>>[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

5

Reactant 3

HCID 174Ethylene GlycolHCID 962WaterHCID 8083Morpholine2×

Product 2

HCID 611632-MorpholinoethanolHCID 15930829HCID 15930829, compoundYield 17%

Conditions

Temperature
150 °C

Procedure

A 22 ml stainless steel Parr bomb reactor was charged with 5.5 g ethylene glycol (88.6 mmol), 1.0 g morpholine (11.5 mmol), 42 mg RuCl3 ×H2O(1.7×10-4 mol) 0.52 g N-methylpyrrolidone (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 150° C. the reactor pressure was 20 psig. At this point, the bomb was cooled to room temperature at which point the pressure stood at 6 psig. The reactor was vented, opened, and the contents analyzed by GLC. The conversion of morpholine was 100% with yields of hydroxyethylmorpholine and bismorpholinoethane being 17% and 79%, respectively (r=0.82).

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

Sources & evidence

ORD record
ord-53e36628f4604848b567c3e995384897
Source dataset
uspto-grants-1989_08
Patent number
US04855425

Reaction notes

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