Propylenediamine → HCID 178442810, compound
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
Reactant 3
Product 1
Reagents, catalysts & solvents 2
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
- customIn a 500 ml four-necked flask equipped with a reflux condenser
- stirringwith stirring for 10 minutes
- temperatureThereafter, while maintaining the temperature at about 120° C.
- temperaturethe mixture was heated for 30 minutes under a reduced pressure
- customto remove isopropanol
- customformed in situ and unreacted water
- additionwere added dropwise for 120 hours
- stirringwith stirring
- temperaturewhile maintaining the temperature at 200° C. or above
- temperaturethe reaction mixture was heated at 210°-220° C. for 4 hours for the completion of the reaction
- 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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