Phthalic Acid → Mono(2-butoxyethyl)phthalic acid

HRID 1710309Notes

Reaction equation

HRID 1710309 reaction equation
[C:1]([OH:12])(=[O:11])[C:2]1[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=1)[C:4]([OH:6])=[O:5].[CH2:13]([O:17][CH2:18][CH2:19]O)[CH2:14][CH2:15][CH3:16].[OH-].[K+]>>[CH2:13]([O:17][CH2:18][CH2:19][C:10]1[CH:9]=[CH:8][CH:7]=[C:3]([C:4]([OH:6])=[O:5])[C:2]=1[C:1]([OH:12])=[O:11])[CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 3

HCID 1017Phthalic AcidHCID 81332-ButoxyethanolHCID 14797Potassium Hydroxide

Product 1

HCID 23187505Mono(2-butoxyethyl)phthalic acid

Conditions

Temperature
90 °C

Procedure

148.1 of anhydrous phthalic acid and the molar equivalent 118.2 n of 2-butoxyethanol were added to a 500 ml glass round-bottomed flask equipped with stirring blades, thermometer and Dimroth condenser, heated while slowly stirring, and after the generated heat at about 90° C. wore off, raised to a temperature of 130° C., which was maintained for 1 hour. The mixture was subsequently cooled to 60° C. The acid value (number of mg of KOH necessary to neutralize 1 g of a sample) of the reaction solution was 226.0. Since the acid value for the case where the reaction is 100% complete is 210.7, the reaction rate was computed to be 93%.

Workup

  1. customequipped with stirring blades
  2. temperaturethermometer and Dimroth condenser, heated
  3. temperatureraised to a temperature of 130° C., which
  4. temperaturewas maintained for 1 hour
  5. temperatureThe mixture was subsequently cooled to 60° C

Sources & evidence

ORD record
ord-f58f2c1e8a3947ee8f360167f5c3d6da
Source dataset
uspto-grants-2010_09
Patent number
US07790290B2

Reaction notes

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