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

HRID 982587

Reaction equation

HRID 982587 reaction equation
[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]

Participants

3

Reactant 2

HCID 7829Dimethyl sebacateHCID 8113Diethanolamine

Product 1

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

Conditions

Temperature
140 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f811ec377c934eb9b5c669d0d761692b
Source dataset
uspto-grants-2005_03
Patent number
US06861192B2

Linked notes

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