Phthalic Acid → Monoisobutylphthalic Acid

HRID 1710300Notes

Reaction equation

HRID 1710300 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].[OH-].[K+]>C(O)C(C)C>[CH2:1]([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])[CH:2]([CH3:3])[CH3:10]

Participants

4

Reactant 2

HCID 1017Phthalic AcidHCID 14797Potassium Hydroxide

Product 1

HCID 22394963Monoisobutylphthalic Acid

Reagents, catalysts & solvents 1

HCID 6560IsobutanolSolvent

Conditions

Temperature
80 °C

Procedure

148.2 g of anhydrous phthalic acid and the molar equivalent 74.2 g of isobutyl alcohol 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 80° C. wore off, raised to a temperature of 140° C., which was maintained for 2 hours. 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 257.5. Since the acid value for the case where the reaction is 100% complete is 252.4, the reaction rate was computed to be 98%.

Workup

  1. customequipped with stirring blades
  2. temperaturethermometer and Dimroth condenser, heated
  3. temperatureraised to a temperature of 140° C., which
  4. temperaturewas maintained for 2 hours
  5. temperatureThe mixture was subsequently cooled to 60° C

Sources & evidence

ORD record
ord-a0ed6675a429476a8f0b77bb67483151
Source dataset
uspto-grants-2010_09
Patent number
US07790290B2

Reaction notes

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