Propylenediamine → HCID 178442810, compound

HRID 1769400Notes

Reaction equation

HRID 1769400 reaction equation
[C:1](#[N:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].N[CH2:15][CH:16]([NH2:18])[CH3:17].NC(N)(C)C>CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4].O>[CH2:2]([C:1]1[NH:13][CH2:15][CH:16]([CH3:17])[N:18]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

6

Conditions

Temperature
120 °C

Procedure

In a 500 ml four-necked flask equipped with a reflux condenser and a thermometer were charged 181 g of lauronitrile and 2 g of titanium tetraisopropoxide. Further, 1 g of water was added with stirring and the mixture was heated up to about 120° C. with stirring for 10 minutes. Thereafter, while maintaining the temperature at about 120° C., the mixture was heated for 30 minutes under a reduced pressure to remove isopropanol formed in situ and unreacted water therefrom. After heating the mixture up to 200°-210° C., 74 g of 1,2-diaminopropane were added dropwise for 120 hours with stirring while maintaining the temperature at 200° C. or above. After the addition of the diaminopropane had been completed, the reaction mixture was heated at 210°-220° C. for 4 hours for the completion of the reaction. The resulting mixture was then subjected to vacuum distillation at 1.0 mmHg and at 160°-165° C. to obtain 219 g of 2-undecyl-4-methyl-2-imidazoline with a yield of 92%.

Workup

  1. customIn a 500 ml four-necked flask equipped with a reflux condenser
  2. stirringwith stirring for 10 minutes
  3. temperatureThereafter, while maintaining the temperature at about 120° C.
  4. temperaturethe mixture was heated for 30 minutes under a reduced pressure
  5. customto remove isopropanol
  6. customformed in situ and unreacted water
  7. additionwere added dropwise for 120 hours
  8. stirringwith stirring
  9. temperaturewhile maintaining the temperature at 200° C. or above
  10. temperaturethe reaction mixture was heated at 210°-220° C. for 4 hours for the completion of the reaction
  11. distillationThe resulting mixture was then subjected to vacuum distillation at 1.0 mmHg and at 160°-165° C.

Sources & evidence

ORD record
ord-7a868f2ff6884e23b6fd0c56e463d828
Source dataset
uspto-grants-1995_01
Patent number
US05380899

Reaction notes

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