Adipic Acid → Hexanedioic acid, polymer with 2,2-bis(hydroxymethyl)-1,3-propanediol, octadecanoate

HRID 2253833Notes

Reaction equation

HRID 2253833 reaction equation
[OH:1][CH2:2][C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][OH:5].[C:10]([OH:29])(=[O:28])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].[Sn].[C:31]([OH:40])(=[O:39])[CH2:32][CH2:33][CH2:34][CH2:35][C:36]([OH:38])=[O:37]>>[C:10]([OH:29])(=[O:28])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].[C:31]([OH:40])(=[O:39])[CH2:32][CH2:33][CH2:34][CH2:35][C:36]([OH:38])=[O:37].[OH:1][CH2:2][C:3]([CH2:8][OH:9])([CH2:6][OH:7])[CH2:4][OH:5]

Participants

5

Reactant 4

HCID 196Adipic AcidHCID 5281Stearic AcidHCID 8285PentaerythritolHCID 5352426Tin atom2×

Product 1

HCID 163183Hexanedioic acid, polymer with 2,2-bis(hydroxymethyl)-1,3-propanediol, octadecanoate

Procedure

As in Example A, 76.2 g (0.56 mole) pentaerythritol and 321.3 g (1.19 mole) technical stearic acid were reacted for 2 hours at 200° to 210° C. in the presence of 0.25 g tin powder. After the addition of 71.5 g (0.49 mole) adipic acid and 0.25 g tin powder, the reaction mixture was heated for another 16 hours to 200°-210° C. under a pressure of from 15 to 16 mbar. After the addition of bleaching earth, filtration under pressure at 90° C. and cooling, the pentaerythritol adipate stearate (8:7:17) (material I; 367 g) was present as a yellow-tinged, brittle, wax-like mass (dropping point 55.0° C.; acid number 6.9; saponification number 281.1; hydroxyl number 15.9).

Workup

  1. temperaturethe reaction mixture was heated for another 16 hours to 200°-210° C. under a pressure of from 15 to 16 mbar
  2. additionAfter the addition
  3. filtrationearth, filtration under pressure at 90° C.
  4. temperaturecooling
  5. customwax-like mass (dropping point 55.0° C.; acid number 6.9; saponification number 281.1; hydroxyl number 15.9)

Sources & evidence

ORD record
ord-370dad1838764e00a38e8086e7b43c63
Source dataset
uspto-grants-1993_08
Patent number
US05232967

Reaction notes

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