Adipic Acid → HCID 131718041, compound

HRID 2253834Notes

Reaction equation

HRID 2253834 reaction equation
[OH:1][CH2:2][CH:3]([CH2:5][OH:6])[OH:4].[C:7]([OH:26])(=[O:25])[CH2:8][CH2:9][CH2:10][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][CH3:24].[Sn].[C:28]([OH:37])(=[O:36])[CH2:29][CH2:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34].[OH:38][CH:39]([CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH3:58])[C:40]([OH:42])=[O:41]>>[OH:38][CH:39]([CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH3:58])[C:40]([OH:42])=[O:41].[C:7]([OH:26])(=[O:25])[CH2:8][CH2:9][CH2:10][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][CH3:24].[C:28]([OH:37])(=[O:36])[CH2:29][CH2:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34].[OH:1][CH2:2][CH:3]([CH2:5][OH:6])[OH:4]

Participants

6

Reactant 5

HCID 196Adipic AcidHCID 753GlycerolHCID 5281Stearic AcidHCID 694172-Hydroxystearic acidHCID 5352426Tin atom3×

Product 1

HCID 131718041HCID 131718041, compound

Procedure

74.5 g (0.8 mole) glycerol and 243.0 g (0.9 mole) technical stearic acid were reacted for 2 hours at 195° to 200° C. in the presence of 0.3 g tin powder. In the course of the first hour, the pressure was slowly and continuously reduced to around 70 mbar and thereafter was left at that level. After the addition of 102.2 g (0.7 mole) adipic acid and 0.3 g tin powder, the reaction mixture was kept at 195°-200° C. for 3 hours under decreasing pressure (final value 17 mbar). 31.2 (0.1 mole) technical hydroxystearic acid and another 0.3 g tin powder were then added before the reaction mixture was heated for another 3 hours to 195°-200° C. The pressure was reduced to 13-16 mbar during the first 30 minutes and thereafter was kept at that level. After the addition of bleaching earth, filtration under pressure at 90° to 100° C. and cooling, the glycerol adipate stearate hydroxystearate (8:7:9:1) (material J; 384 g) was present as a yellow brown-tinged wax-like mass (dropping point 48.0° C.; acid number 7.9; saponification number 327.3; hydroxyl number 20.1).

Workup

  1. waitwas left at that level
  2. temperaturewas heated for another 3 hours to 195°-200° C
  3. customwas reduced to 13-16 mbar during the first 30 minutes
  4. additionAfter the addition
  5. filtrationearth, filtration under pressure at 90° to 100° C.
  6. temperaturecooling
  7. customwas present as a yellow brown-tinged wax-like mass (dropping point 48.0° C.; acid number 7.9; saponification number 327.3; hydroxyl number 20.1)

Sources & evidence

ORD record
ord-ebb250faf789424ebfe7aae42523e93b
Source dataset
uspto-grants-1993_08
Patent number
US05232967

Reaction notes

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