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

HRID 2253828Notes

Reaction equation

HRID 2253828 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, 71.4 g (0.525 mole) pentaerythritol and 283.5 g (1.05 mole) stearic acid were reacted for 3 hours at 200°-210° C. in the presence of 0.2 g tin powder. 65.7 g (0.45 mole) adipic acid and 0.2 g tin powder were then added to the reaction mixture before it was heated for 5.5 hours to 200°-210° C. The pressure was slowly reduced to 24 mbar during the first 90 minutes and thereafter was kept at that value. After filtration under pressure and cooling, the pentaerythritol adipate stearate (7:6:14) (material B; 372 g) was present as a yellowish, brittle, wax-like mass (dropping point 53.2° C.; acid number 2.1; saponification number 286.4; hydroxyl number 22).

Workup

  1. temperaturewas heated for 5.5 hours to 200°-210° C
  2. customwas slowly reduced to 24 mbar during the first 90 minutes
  3. filtrationAfter filtration under pressure
  4. temperaturecooling
  5. customwax-like mass (dropping point 53.2° C.; acid number 2.1; saponification number 286.4; hydroxyl number 22)

Sources & evidence

ORD record
ord-f813f3b24a1f4991adaccba564b2f653
Source dataset
uspto-grants-1993_08
Patent number
US05232967

Reaction notes

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