Glycol monoethyl ether → Tris(2-(2-ethoxyethoxy)ethyl)amine

HRID 1577492Notes

Reaction equation

HRID 1577492 reaction equation
Cl.Cl[CH2:3][CH2:4][N:5]([CH2:9][CH2:10]Cl)[CH2:6][CH2:7]Cl.[CH2:12]([O:14][CH2:15][CH2:16][OH:17])[CH3:13]>>[CH2:4]([N:5]([CH2:9][CH2:10][O:17][CH2:16][CH2:15][O:14][CH2:12][CH3:13])[CH2:6][CH2:7][O:17][CH2:16][CH2:15][O:14][CH2:12][CH3:13])[CH2:3][O:17][CH2:16][CH2:15][O:14][CH2:12][CH3:13]

Participants

3

Reactant 2

HCID 8076Glycol monoethyl etherHCID 61220Tris(2-chloroethyl)amine hydrochloride

Product 1

HCID 3018623Tris(2-(2-ethoxyethoxy)ethyl)amineYield 68%

Procedure

51.6 g (i.e., 0.215 mol) of tris-(2-chloroethyl)-amine hydrochloride were added to the above mixture (a). The mixture was subsequently heated at the reflux temperature of the 2-ethoxyethanol for 12 hours and the solvent was then distilled under reduced pressure. The excess sodium 2-ethoxyethanolate was neutralized by adding 12 cm3 of aqueous HCl (10 N) thereto. The sodium chloride was filtered off and the solution was distilled. The tris-(3,6-dioxaoctyl)-amine distilled between 200° C. and 210° C. under a pressure of 1 mm Hg. The yield was 68%.

Workup

  1. distillationthe solvent was then distilled under reduced pressure
  2. additionby adding 12 cm3 of aqueous HCl (10 N)
  3. filtrationThe sodium chloride was filtered off
  4. distillationthe solution was distilled
  5. distillationThe tris-(3,6-dioxaoctyl)-amine distilled between 200° C. and 210° C. under a pressure of 1 mm Hg

Sources & evidence

ORD record
ord-5ca93669df874129a341432824b7b7da
Source dataset
uspto-grants-1981_09
Patent number
US04288386

Reaction notes

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