Propylene Oxide → 2-Propanol, 1,1'-[[2-[(2-hydroxypropyl)amino]ethyl]imino]bis-

HRID 2231169

Reaktionsgleichung

Reaktionsgleichung von HRID 2231169
[CH2:1]1[O:4][CH:2]1[CH3:3].[OH:5][CH:6]([CH3:16])[CH2:7][NH:8][CH2:9][CH2:10][NH:11][CH2:12][CH:13]([OH:15])[CH3:14]>C(O)C.CO.CCOCC>[OH:4][CH:2]([CH3:3])[CH2:1][N:8]([CH2:7][CH:6]([OH:5])[CH3:16])[CH2:9][CH2:10][NH:11][CH2:12][CH:13]([OH:15])[CH3:14]

Komponenten

6

Edukt 2

HCID 6378Propylene OxideHCID 1029642-Propanol, 1,1'-(1,2-ethanediyldiimino)bis-

Produkt 1

HCID 1120572-Propanol, 1,1'-[[2-[(2-hydroxypropyl)amino]ethyl]imino]bis-Ausbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittel2×HCID 887MethanolLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

(V-a): Propylene oxide (181.6 g, 0.3 mol) in 25 mL of absolute ethanol was added dropwise for 4.5 hours to a solution of N,N'-bis(2-hydroxypropyl)ethylenediamine (IV-a) (55 g, 0.3 mol) in 50 mL each of absolute ethanol, methanol and distilled water at 80° C. The reaction mixture was cooled and concentrated to give a milky white viscous suspension. The suspension was dissolved in ether and dried over anhydrous sodium sulfate. Unreacted (IV-a) precipitated and was removed by filtration. Ether was removed from the clear filtrate to produce a viscous liquid. Fractional distillation of the oil produced N,N,N'-tris(2-hydroxypropyl)ethylenediamine [bp. 140° C. at 0.15 mm; yield 55 percent; IR(neet): 3350(broad OH); NMR(CDCl3): δ 3.8(broad m, 3H); 2.5(broad m, 10H); 1.1(d, 9H)].

Aufarbeitung

  1. distillationdistilled water at 80° C
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated
  4. customto give a milky white viscous suspension
  5. dry with materialdried over anhydrous sodium sulfate
  6. customUnreacted (IV-a) precipitated
  7. customwas removed by filtration
  8. customEther was removed from the clear filtrate
  9. customto produce a viscous liquid
  10. distillationFractional distillation of the oil

Quellen und Nachweise

ORD-Eintrag
ord-6a412bd7af194b3ab70d90fd716fe470
Quelldatensatz
uspto-grants-1988_11
Patentnummer
US04781921

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