Dimethyl sebacate → N,N,N',N'-tetrakis(2-hydroxyethyl)sebacamide

HRID 982587

Reaktionsgleichung

Reaktionsgleichung von HRID 982587
[C:1]([O:15]C)(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12]C)=O.[NH:17]([CH2:21][CH2:22][OH:23])[CH2:18][CH2:19][OH:20]>>[OH:20][CH2:19][CH2:18][N:17]([CH2:21][CH2:22][OH:23])[C:10](=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:1]([N:17]([CH2:21][CH2:22][OH:23])[CH2:18][CH2:19][OH:20])=[O:15]

Komponenten

3

Edukt 2

HCID 7829Dimethyl sebacateHCID 8113Diethanolamine

Produkt 1

HCID 231267N,N,N',N'-tetrakis(2-hydroxyethyl)sebacamide

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A mixture of 57.58 g (0.25 mol) dimethyl sebacate and 157.71 g (1.50 mol) of diethanolamine was heated in a 140° C. bath under nitrogen for 2.5 hrs while collecting the methanol condensate. The reaction mixture was subsequently heated in a 200° C. at reduced pressure (1.5 mm) to distill off excess diethanolamine. The highly viscous oily residue was dissolved in an equal volume of acetone and stirred overnight. The resulting crystalline solid was collected, washed with acetone, and dried. The yield of product was 35.0 g (9.3% of theory); mp=87-98° C.

Aufarbeitung

  1. customwhile collecting the methanol condensate
  2. temperatureThe reaction mixture was subsequently heated in a 200° C. at reduced pressure (1.5 mm)
  3. distillationto distill off excess diethanolamine
  4. dissolutionThe highly viscous oily residue was dissolved in an equal volume of acetone
  5. customThe resulting crystalline solid was collected
  6. washwashed with acetone
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-f811ec377c934eb9b5c669d0d761692b
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06861192B2

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