Propylene Carbonate → 2-Oxazolidinone, 3-(2-hydroxyethyl)-

HRID 1441769Notes

Reaction equation

HRID 1441769 reaction equation
[C:1]1(=[O:7])[O:6][CH:4]([CH3:5])CO1.[NH:8](CCO)[CH2:9][CH2:10][OH:11]>>[OH:11][CH2:10][CH2:9][N:8]1[CH2:5][CH2:4][O:6][C:1]1=[O:7]

Participants

3

Conditions

Temperature
120 °C

Procedure

5.1 mol of propylene carbonate were provided as an initial charge at 23° C. under a nitrogen atmosphere. 5 mol of diethanolamine were added over 30 to 120 minutes with stirring, and the temperature of the reaction mixture rose. On completion of the addition the mixture was heated to 120° C. in the course of 10 to 120 minutes and left to stir at 120° C. for 2 hours. Then a 10 to 20 mbar vacuum was applied, the temperature was raised from 120° C. to 160° C. and propylene glycol was distilled off. The N-(2-hydroxyethyl)oxazolidin-2-one obtained almost quantitatively as undistilled bottom product comprised 96 to 98% by weight of product of value and had a Hazen color number in the range from 0 to 15.

Workup

  1. additionan initial charge at 23° C. under a nitrogen atmosphere
  2. additionOn completion of the addition the mixture
  3. waitleft
  4. stirringto stir at 120° C. for 2 hours
  5. temperaturethe temperature was raised from 120° C. to 160° C.
  6. distillationpropylene glycol was distilled off

Sources & evidence

ORD record
ord-9daae74d86f34393ab083b0b0969d68b
Source dataset
uspto-grants-2010_02
Patent number
US07655733B2

Reaction notes

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