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

HRID 1441770Notes

Reaction equation

HRID 1441770 reaction equation
[C:1]1(=[O:7])[O:6][CH:4]([CH3:5])CO1.[NH:8](CCO)[CH2:9][CH2:10][OH:11].[OH-].[Na+]>>[OH:11][CH2:10][CH2:9][N:8]1[CH2:5][CH2:4][O:6][C:1]1=[O:7]

Participants

4

Conditions

Temperature
100 °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 100° C. in the course of 10 to 120 minutes. At 100° C., 2.5 mol % of NaOH in solid form were added, and the batch was left to stir at 100° C. for 2 hours. Then a 10 to 20 mbar vacuum was applied, the temperature was raised from 100° 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 96-98% by weight of product of value and had a Hazen color number in the range from 0 to 25.

Workup

  1. additionan initial charge at 23° C. under a nitrogen atmosphere
  2. additionOn completion of the addition the mixture
  3. waitthe batch was left
  4. stirringto stir at 100° C. for 2 hours
  5. temperaturethe temperature was raised from 100° C. to 160° C.
  6. distillationpropylene glycol was distilled off

Sources & evidence

ORD record
ord-ed0e5bd70f59487080554ee92793804e
Source dataset
uspto-grants-2010_02
Patent number
US07655733B2

Reaction notes

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