Ethylenediamine → 2-Heptadecyl-2-imidazoline

HRID 1769401Notes

Reaction equation

HRID 1769401 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].[C:5](#N)[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]>CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4].O>[CH2:21]([C:22]1[NH:3][CH2:2][CH2:1][N:4]=1)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH3:5]

Participants

5

Reactant 2

HCID 3301EthylenediamineHCID 12532Octadecanenitrile

Product 1

HCID 77442-Heptadecyl-2-imidazolineYield 86.7%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 11026Titanium isopropoxideCatalyst

Conditions

Temperature
210 °C

Procedure

In a 500 ml SUS 316L stainless steel autoclave were charged 60 g of ethylene diamine, 267 g of stearonitrile and 2.5 g of titanium tetraisopropoxide. After addition of 1 g of water, the mixture was heated up to 210° C. with stirring and maintained at that temperature for 4 hours while removing ammonia produced in situ to maintain the pressure within the autoclave at 8-9 kg/cm2G. The resulting mixture was then subjected to vacuum distillation at 0.6 mmHg and at 230°-235° C. to obtain 267 g of 2-heptadecyl-2-imidazoline with a yield of 86%.

Workup

  1. temperaturemaintained at that temperature for 4 hours
  2. customwhile removing ammonia
  3. customproduced in situ
  4. temperatureto maintain the pressure within the autoclave at 8-9 kg/cm2G
  5. distillationThe resulting mixture was then subjected to vacuum distillation at 0.6 mmHg and at 230°-235° C.

Sources & evidence

ORD record
ord-82e45275f0e94ceba23c7cdc6779cf9f
Source dataset
uspto-grants-1995_01
Patent number
US05380899

Reaction notes

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