Adipic Acid → HCID 86587302, compound

HRID 1357446Notes

Reaction equation

HRID 1357446 reaction equation
[OH:1][CH2:2][CH:3]([CH2:5][OH:6])[OH:4].[C:7]([OH:24])(=[O:23])[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][CH3:22].[C:25]([OH:34])(=[O:33])[CH2:26][CH2:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31]>O>[C:25]([OH:34])(=[O:33])[CH2:26][CH2:27][CH2:28][CH2:29][C:30]([OH:32])=[O:31].[OH:1][CH2:2][CH:3]([CH2:5][OH:6])[OH:4].[C:7]([OH:24])(=[O:23])[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][CH3:22]

Participants

5

Reactant 3

HCID 196Adipic AcidHCID 753Glycerol2×HCID 985Palmitic Acid

Product 1

HCID 86587302HCID 86587302, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a 5-liter heated resin kettle equipped with agitator, thermometer, and condenser with distillation head, 1246 g (40.6 equivalents) of glycerol was added. The glycerol was agitated and heated to about 100° C., and 1068 g (4.2 equivalents) of palmitic acid was added. While maintaining the batch temperature at 100-120° C., 2506 g (34.3 equivalents) of adipic acid was added. The batch was heated to 150-210° C. and water of reaction was collected at atmospheric pressure. Water began to distill when the temperature of the reaction mixture reached 150-160° C. The batch was heated further and water collected until a total of 437 g was obtained. The 437 g of water collected was 63% of the theoretical amount (693 g).

Workup

  1. temperatureTo a 5-liter heated resin kettle
  2. customequipped with agitator
  3. additionwas added
  4. temperatureWhile maintaining the batch temperature at 100-120° C.
  5. temperatureThe batch was heated to 150-210° C.
  6. customwas collected at atmospheric pressure
  7. distillationto distill when the temperature of the reaction mixture
  8. customreached 150-160° C
  9. temperatureThe batch was heated further
  10. customwater collected until a total of 437 g
  11. customwas obtained
  12. customThe 437 g of water collected

Sources & evidence

ORD record
ord-f848ee89f97e4093b4f31e9091a904d6
Source dataset
uspto-grants-2003_07
Patent number
US06592913B2

Reaction notes

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