Phthalic Anhydride → Diisodecyl Phthalate

HRID 370382

Reaction equation

HRID 370382 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[CH2:12]([OH:22])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20]>O>[C:4]([O:6][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])(=[O:5])[C:3]1[C:2](=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:1]([O:22][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH:19]([CH3:20])[CH3:21])=[O:11]

Participants

4

Reactant 2

HCID 6811Phthalic AnhydrideHCID 32898Isodecanol

Product 1

HCID 33599Diisodecyl Phthalate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
210 °C

Procedure

A standard 1-liter esterification system was charged with 111 g of phthalic anhydride, 284 g of isodecyl alcohol and 0.5 g of catalyst ATC-II. The system was heated to reflux and the temperature was maintained at 210° C. at reduced pressure. At the end of 1.25 hours the water of reaction was collected and the acid number of the residue was measured to be 0.03 mg KOH/g. Heating was discontinued and excess alcohol removed as the pressure was reduced to 100 torr. Adjusting the temperature to 150° C., hydrolysis of the catalyst and removal of remaining alcohol was accomplished by steam distillation using 40 ml water during 35 minutes at 150° C. and 100 torr. After drying for 15 minutes at these conditions the cloudy crude product was cooled to 90° C. and filtered through a No. 1 Whatman paper to yield a clear residue product diisodecyl phthalate (DIDP) (nD25 =1.4850) having an acid number of 0.04 mg KOH/g and a color of 15 APHA.

Workup

  1. temperatureThe system was heated
  2. temperatureto reflux
  3. customwas collected
  4. temperatureHeating
  5. customexcess alcohol removed as the pressure
  6. customto 150° C.
  7. customhydrolysis of the catalyst and removal of remaining alcohol
  8. distillationwas accomplished by steam distillation
  9. customduring 35 minutes
  10. customat 150° C.
  11. dry with materialAfter drying for 15 minutes at these conditions the cloudy crude product
  12. temperaturewas cooled to 90° C.
  13. filtrationfiltered through a No

Sources & evidence

ORD record
ord-f5a07199bc83435780eff40651145158
Source dataset
uspto-grants-1985_07
Patent number
US04526725

Linked notes

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