Water → HCID 131730116, compound

HRID 2195010Notes

Reaction equation

HRID 2195010 reaction equation
C(O)C(O)C[O:4][CH2:5][CH:6]([OH:9])[CH2:7][OH:8].[C:12]([OH:22])(=[O:21])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19].O>C1(C)C=CC=CC=1>[C:12]([OH:22])(=[O:21])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]([CH3:19])[CH3:20].[OH:4][CH2:5][CH:6]([CH2:7][OH:8])[OH:9].[OH:4][CH2:5][CH:6]([CH2:7][OH:8])[OH:9]

Participants

5

Reactant 3

HCID 962WaterHCID 33635Isononanoic acidHCID 42953Diglycerin

Product 1

HCID 131730116HCID 131730116, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
200 °C

Procedure

In a four-neck 1000 mL flask equipped with a stirrer, a thermometer, a gas inlet tube, and a Dean-Stark condenser with a water measuring trap were placed 166.2 g (1.0 mol) of diglycerin, 237.3 g (1.5 mol) of isononanoic acid, and 150 mL of toluene as a solvent. Then, the reaction mixture was heated to 200 degrees C. under a flow of nitrogen gas in a rate of 20 mL/min. At the temperature, the reaction took place while distilling off the produced water with the solvent azeotropically. When the distillation-off water subsided, the temperature was raised to 220 degrees C. to further continue the reaction. When the distillation-off water stopped, the reaction was terminated. It took about 6 hours from the start of the reaction to this point. Diglycerin isononanoate was obtained as a pale yellow viscous oil in an amount of 411.5 g (hydroxyl value: 132, acid value: 0.3).

Workup

  1. customIn a four-neck 1000 mL flask equipped with a stirrer
  2. customa thermometer, a gas inlet tube, and a Dean-Stark condenser with a water measuring trap were placed
  3. distillationwhile distilling off the produced water with the solvent azeotropically
  4. temperaturethe temperature was raised to 220 degrees C
  5. customthe reaction
  6. customthe reaction was terminated
  7. customIt took about 6 hours from the start of the reaction to this point

Sources & evidence

ORD record
ord-8782b8dacbe146498554fd52b0569eb0
Source dataset
uspto-grants-2012_12
Patent number
US08334400B2

Reaction notes

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