STEARYLDIETHANOLAMINE synthesis
- Product Name:STEARYLDIETHANOLAMINE
- CAS Number:10213-78-2
- Molecular formula:C22H47NO2
- Molecular Weight:357.61
111-42-2
112-89-0
10213-78-2
The general procedure for the synthesis of 2,2'-(octadecylimino)diethanol from diethanolamine and stearyl bromide was as follows: in a 500 mL three-necked flask, 10 g (95 mmol) of diethanolamine, 37.96 g (0.114 mol) of octadecyl bromide, 39.33 g (0.285 mol) of potassium bicarbonate, and 0.5 g of potassium iodide were sequentially added, followed by 200 mL of acetonitrile as solvent. The reaction mixture was heated to reflux with stirring and kept for 3 hours. After completion of the reaction, the solvent was removed by rotary evaporator and the residue was dissolved in dichloromethane. The organic phase was washed twice separately with deionized water, dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure. The residue was recrystallized with acetone to give 33 g of white crystal product in quantitative yield. The melting point of the product was 49 °C. Thin layer chromatography (TLC) showed an Rf value of 0.20 (unfolding agent was dichloromethane/methanol, 90:10 v/v). Infrared spectroscopy (KBr press) showed a hydroxyl absorption peak at 3310 cm-1 . The NMR hydrogen spectra (200 MHz, CDCl3, with hexamethyldisiloxane as internal standard) chemical shifts δ ppm were 3.53 (triple peak, 4H, J = 5.43 Hz, CH2-O), 3.27 (single peak, 2H, OH), 2.57 (triple peak, 4H, J = 5.43 Hz, N-CH2-CO), 2.44 (triple peak, 2H. J = 7.06 Hz, CH2-N), 1.34 (multiple peaks, 2H, CH2-CN), 1.18 (single peak, 30H, CH2), 0.80 (triple peak, 3H, J = 5.85 Hz, CH3).
111-42-2
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112-89-0
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10213-78-2
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Yield:10213-78-2 100%
Reaction Conditions:
with potassium hydrogencarbonate;potassium iodide in acetonitrile for 3 h;Heating / reflux;
Steps:
4.4-1
In a 500 ml Erlenmeyer flask, 10 g (95 mmol) of diethanolamine, 37.96 g (0.114 mol) of octadecane bromide, 39.33 g (0.285 mol) of potassium bicarbonate and 0.5 g of potassium iodide in 200 ml of acetonitrile were mixed. The reaction mixture was stirred and heated under reflux for 3 hours. At the end of the reaction, the solvent was evaporated and the residue was taken up in dichloromethane. The organic phase was washed two times with water, dried over MgSO4, filtered, and concentrated under vacuum. The residue was crystallized from acetone, to obtain 33 g of white crystal. Yield: quantitative. Melting point: 49° C. Rf: 0.20 (CH2Cl2/MeOH, 90:10 v/v). IR (KBr): 3310 (O-H) cm-1 1H NMR (200 MHz, CDCl3, HMDS) δ ppm: 3.53 (t, 4H, J=5.43 Hz, CH2-O), 3.27 (s1, 2H, OH), 2.57 (t, 4H, J=5.43 Hz, N-CH2-C-O), 2.44 (t, 2H, J=7.06 Hz, CH2-N), 1.34 (m, 2H, CH2-C-N), 1.18 (s1, 30H, CH2), 0.80 (t, 3H, J=5.85 Hz, CH3)
References:
Yang Ji Chemical Company Ltd. US2005/75345, 2005, A1 Location in patent:Page/Page column 7
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