Adipic Acid → HCID 131718042, compound

HRID 2253837Notes

Reaction equation

HRID 2253837 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].[OH:41][CH:42]([CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH3:61])[C:43]([OH:45])=[O:44]>>[OH:41][CH:42]([CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH2:60][CH3:61])[C:43]([OH:45])=[O:44].[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

6

Reactant 5

HCID 196Adipic AcidHCID 5281Stearic AcidHCID 8285PentaerythritolHCID 694172-Hydroxystearic acidHCID 5352426Tin atom3×

Product 1

HCID 131718042HCID 131718042, compound

Procedure

95.2 g (0.7 mole) pentaerythritol and 324.0 g (1.2 moles) technical stearic acid were reacted for 2 hours at 205°-210° C. in the presence of 0.3 g tin powder. The pressure was continuously reduced to 10-20 mbar and, finally, was kept at that level. After the addition of 87.6 g (0.6 mole) adipic acid and 0.15 g tin powder, the reaction mixture was heated for another 2 hours to 205°-210° C. under decreasing pressure (final vacuum 10-20 mbar). 93.6 g (0.3 mole) technical hydroxystearic acid and another 0.15 g tin powder were then added before the reaction mixture was heated for another 2 hours to 205°-210° C. The pressure was continuously reduced to a final vacuum of 10 to 15 mbar. After the addition of bleaching earth, filtration under pressure at 90° C. and cooling, the pentaerythritol adipate stearate hydroxystearate (7:6:12:3) (material M; 482 g) was present as a yellowish, slightly brittle, wax-like, slightly caking mass (dropping point 51.5° C.; acid number 1.06; saponification number 277.5; hydroxyl number 43.2).

Workup

  1. temperaturethe reaction mixture was heated for another 2 hours to 205°-210° C. under decreasing pressure (final vacuum 10-20 mbar)
  2. temperaturewas heated for another 2 hours to 205°-210° C
  3. additionAfter the addition
  4. filtrationearth, filtration under pressure at 90° C.
  5. temperaturecooling
  6. customwax-like, slightly caking mass (dropping point 51.5° C.; acid number 1.06; saponification number 277.5; hydroxyl number 43.2)

Sources & evidence

ORD record
ord-fb8cf6ca31ef44048e5fff7d98d21bb7
Source dataset
uspto-grants-1993_08
Patent number
US05232967

Reaction notes

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