Ethanolamine → N-Stearoylethanolamine

HRID 1659898Notes

Reaction equation

HRID 1659898 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].[C:5](O)(=[O:23])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>C(O)C>[OH:2][CH2:1][CH2:3][NH:4][C:5](=[O:23])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 5281Stearic Acid

Product 1

HCID 27902N-Stearoylethanolamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
135 °C

Procedure

To a solution of 24.4 g (0.4 mole) ethanolamine in 500 ml ethanol at 60° C. was added 85.2 g (0.3 mole) stearic acid. The ethanol was distilled off until the pot temperature reached 100° C., at which time 300 ml toluene was added, and the water was distilled off as an azeotrope. After 5 hours at 110° C., 6 ml water was recovered in the Stark & Dean trap. Some toluene was removed to raise the pot temperature to 135° C. After an additional 4 hours, another 7 ml water was trapped. The title product (38.5 g) that crystallized on cooling had a melting point of 96°-99° C.

Workup

  1. distillationThe ethanol was distilled off until the pot temperature
  2. customreached 100° C., at which time 300 ml toluene
  3. additionwas added
  4. distillationthe water was distilled off as an azeotrope
  5. custom6 ml water was recovered in the Stark & Dean trap
  6. customSome toluene was removed
  7. waitAfter an additional 4 hours
  8. customThe title product (38.5 g) that crystallized
  9. temperatureon cooling

Sources & evidence

ORD record
ord-4bcfd9111620489ba9b02f221da07ddc
Source dataset
uspto-grants-1981_12
Patent number
US04305868

Reaction notes

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