Adipic Acid → HCID 20466974, compound

HRID 992655Notes

Reaction equation

HRID 992655 reaction equation
[OH:1][CH2:2][CH:3]([CH2:5][OH:6])[OH:4].[C:7]([OH:16])(=[O:15])[CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13]>O>[C:7]([OH:16])(=[O:15])[CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13].[OH:1][CH2:2][CH:3]([CH2:5][OH:6])[OH:4]

Participants

4

Reactant 2

HCID 196Adipic Acid2×HCID 753Glycerol2×

Product 1

HCID 20466974HCID 20466974, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
100 °C

Procedure

To a 1-liter heated resin kettle equipped with agitator, thermometer, and condenser with distillation head, 294 g (9.64 equivalents) of glycerol was added. The glycerol was agitated and heated to about 100° C., and 704 g (9.64 equivalents) of adipic acid was added. After all the adipic acid was added, the batch was heated to 150-200° C. and water was taken off at atmospheric pressure. Water began to distill when the temperature of the reaction mixture reached 150 to 160° C. The batch was heated further to 160 to 210° C. and water taken off until the batch gelled. Gelation began to occur after about 134 g of the water was collected. The 134 g of water collected was 77% of the theoretical amount. Depending upon the level of post-gelation heating, the product had a consistency ranging from a sticky gum containing about 15% by weight of a water-soluble fraction to that of a somewhat hard glass with a water-soluble fraction of 1% or less.

Workup

  1. temperatureTo a 1-liter heated resin kettle
  2. customequipped with agitator
  3. additionwas added
  4. temperaturethe batch was heated to 150-200° C.
  5. distillationto distill when the temperature of the reaction mixture
  6. customreached 150 to 160° C
  7. temperatureThe batch was heated further to 160 to 210° C.
  8. customwas collected
  9. customThe 134 g of water collected
  10. temperatureheating
  11. additioncontaining about 15% by weight of a water-soluble fraction to that of a somewhat hard glass with a water-soluble fraction of 1% or less

Sources & evidence

ORD record
ord-1723b77274a640e6bd275d666d622a2a
Source dataset
uspto-grants-2002_10
Patent number
US06469129B1

Reaction notes

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