Succinic anhydride → Succinic Acid

HRID 558009Notes

Reaction equation

HRID 558009 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH2:3][CH2:2]1.[CH3:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][OH:18].[OH-].[K+]>>[C:1]([OH:6])(=[O:7])[CH2:2][CH2:3][C:4]([OH:9])=[O:5].[CH3:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][OH:18]

Participants

5

Reactant 3

HCID 7922Succinic anhydrideHCID 8178Triethylene glycol monomethyl etherHCID 14797Potassium Hydroxide

Product 2

HCID 1110Succinic AcidHCID 8178Triethylene glycol monomethyl ether

Conditions

Temperature
80 °C

Procedure

In a 3-L flask equipped with a stirrer, a thermometer and a dehydration tube, 500 g of succinic anhydride, 2,463 g of triethylene glycol monomethyl ether and 9.5 g of paratoluenesulfonic acid monohydrate were charged and the mixture was reacted under reduced pressure of 4 to 10.7 kPa at 110° C. for 15 hours, while blowing nitrogen (500 mL/minute) into the space. The acid value of the reaction solution was 1.6 (KOH mg/g). To the reaction solution, 27 g of an adsorbent Kyoward 500SH (manufactured by Kyowa Chemical Industry Co., Ltd.) was added, stirred at 80° C. at 2.7 kPa for 45 minutes, and filtered. Thereafter, triethylene glycol monomethyl ether was distilled off at a liquid temperature of 115 to 200° C. at a pressure of 0.03 kPa. After cooling to 80° C., the residual liquid was filtered under reduced pressure, to give a diester of succinic acid and triethylene glycol monomethyl ether as a filtrate. The resultant diester had an acid value of 0.2 (KOH mg/g), a saponification value of 276 (KOH mg/g), a hydroxyl value of 1 or less (KOH mg/g) and a hue of APHA200.

Workup

  1. customIn a 3-L flask equipped with a stirrer
  2. customthe mixture was reacted under reduced pressure of 4 to 10.7 kPa at 110° C. for 15 hours
  3. additionTo the reaction solution, 27 g of an adsorbent Kyoward 500SH (manufactured by Kyowa Chemical Industry Co., Ltd.) was added
  4. filtrationfiltered
  5. distillationThereafter, triethylene glycol monomethyl ether was distilled off at a liquid temperature of 115 to 200° C. at a pressure of 0.03 kPa
  6. temperatureAfter cooling to 80° C.
  7. filtrationthe residual liquid was filtered under reduced pressure

Sources & evidence

ORD record
ord-0a3c9085804a4677b3efe5dbaf123d4d
Source dataset
uspto-grants-2011_11
Patent number
US08062574B2

Reaction notes

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