Adipic Acid → Dibenzyl adipate

HRID 448256Notes

Reaction equation

HRID 448256 reaction equation
[C:1]([OH:10])(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([OH:8])=[O:7].[CH2:11](O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-].[K+]>>[C:1]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:7]

Participants

4

Reactant 3

HCID 196Adipic AcidHCID 244Benzyl AlcoholHCID 14797Potassium Hydroxide

Product 1

HCID 75561Dibenzyl adipate

Conditions

Temperature
80 °C

Procedure

A 3 L flask equipped with a stirrer, a thermometer, and a dehydration tube was charged with 438 g of adipic acid, 779 g of benzyl alcohol, and 5.7 g of paratoluenesulfonic acid monohydrate, and the components were reacted at 120° C. for 4 hours under a reduced pressure of from 6 to 10.7 kPa, while blowing nitrogen (500 mL/minute) into a space portion. The reaction mixture had an acid value of 1.2 (KOH mg/g). Eight grams of an adsorbent KYOWAAD 500SH (manufactured by Kyowa Kagaku Kogyo) was added to the reaction mixture, and the mixture was stirred at 80° C. and 2.7 kPa for 45 minutes. Thereafter, benzyl alcohol was distilled off at a liquid temperature of from 120° to 183° C. and a pressure of 0.27 kPa, and cooled to 80° C., and the residue was filtered under a reduced pressure, to provide dibenzyl adipate as a filtrate. The resulting dibenzyl adipate had an acid value of 0.16 (KOH mg/g), a saponification value of 512 (KOH mg/g), a hydroxyl value of 1 or less (KOH mg/g), and a hue APHA of 80.

Workup

  1. customA 3 L flask equipped with a stirrer
  2. customthe components were reacted at 120° C. for 4 hours under a reduced pressure of from 6 to 10.7 kPa
  3. additionEight grams of an adsorbent KYOWAAD 500SH (manufactured by Kyowa Kagaku Kogyo) was added to the reaction mixture
  4. distillationThereafter, benzyl alcohol was distilled off at a liquid temperature of from 120° to 183° C.
  5. temperaturea pressure of 0.27 kPa, and cooled to 80° C.
  6. filtrationthe residue was filtered under a reduced pressure

Sources & evidence

ORD record
ord-25585c5c68d94fe18b127b0f9952880c
Source dataset
uspto-grants-2013_07
Patent number
US08481620B2

Reaction notes

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