Adipic Acid → HCID 86747074, compound

HRID 2253838Notes

Reaction equation

HRID 2253838 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:41]([OH:50])(=[O:49])[CH:42]([CH:44]([C:46]([OH:48])=[O:47])[OH:45])[OH:43]>>[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:46]([CH:44]([CH:42]([C:41]([OH:50])=[O:49])[OH:43])[OH:45])([OH:48])=[O:47].[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

6

Reactant 5

HCID 196Adipic AcidHCID 8752,3-Dihydroxybutanedioic AcidHCID 5281Stearic AcidHCID 8285PentaerythritolHCID 5352426Tin atom2×

Product 1

HCID 86747074HCID 86747074, compound

Conditions

Temperature
150 °C

Procedure

66.6 g (0.49 mole) pentaerythritol and 302.4 g (1.12 moles) technical stearic acid were reacted for 1.5 hours at 195° to 205° C. in the presence of 0.2 g tin powder. The pressure was continuously reduced to 12 mbar and was kept at that level for the rest of the reaction time. 51.5 g (0.35 mole) adipic acid and another 0.2 g tin powder were then added before the mixture was heated for another 2.5 hours to 195°-205° C. under a pressure of 16 mbar. The reaction mixture was cooled to 150° C. After the addition of 10.5 g (0.07 mole) tartaric acid, the mixture was continuously heated from 150° C. to 185° C. over a period of 2.5 hours, during which the pressure was gradually reduced to a final vacuum of 13 mbar. After filtration under pressure at 90° C. to 100° C. in the presence of bleaching earth, followed by cooling, the pentaerythritol adipate tartrate stearate (7:5:1:16) (material N; 328 g) was present as a yellowish, brittle wax-like mass (dropping point 56.4° C.; acid number 3.0; saponification number 271.3; hydroxyl number 18.7).

Workup

  1. temperaturewas heated for another 2.5 hours to 195°-205° C. under a pressure of 16 mbar
  2. temperaturethe mixture was continuously heated from 150° C. to 185° C. over a period of 2.5 hours, during which the pressure
  3. filtrationAfter filtration under pressure at 90° C. to 100° C. in the presence
  4. temperatureby cooling
  5. custombrittle wax-like mass (dropping point 56.4° C.; acid number 3.0; saponification number 271.3; hydroxyl number 18.7)

Sources & evidence

ORD record
ord-9397c8ad317541e4a2edcf30f878e29b
Source dataset
uspto-grants-1993_08
Patent number
US05232967

Reaction notes

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