Adipic Acid → Diisodecyl Adipate

HRID 370383

Reaction equation

HRID 370383 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)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19]>>[C:1]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])(=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])=[O:7]

Participants

3

Reactant 2

HCID 196Adipic AcidHCID 32898Isodecanol

Product 1

HCID 33733Diisodecyl Adipate

Conditions

Temperature
220 °C

Procedure

A standard 2-liter esterification apparatus was charged with 292 g adipic acid and 727 g isodecyl alcohol. The mixture was heated to reflux, removing water as formed. After 30 minutes of reflux the temperature was 215° C. and 40 ml of water was collected, at which time 0.9 g of catalyst compound ATC-I was added to the flask. The pressure was reduced as needed to maintain the reflux temperature at 220° C. After an additional 45 minutes the water of reaction was collected and the acid number of the residue was measured to be 0.01 mg KOH/g. Heating was discontinued and excess alcohol removed as the pressure was reduced to 20 torr. The reaction mixture was cooled to 170° C., the catalyst was hydrolyzed and the remaining alcohol removed by steam distillation using 100 ml water during 2 hours at 100 torr. The residue was filtered with a No. 1 Whatman paper coated with diatomaceous earth to yield a clear residue product diisodecyl adipate (DIDA) (nD25 =1.4502) having an acid number of 0.05 mg KOH/g and color of 15 APHA. The product remained clear after storage for six months at ambient temperature.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. customremoving water
  4. customas formed
  5. temperatureAfter 30 minutes of reflux the temperature
  6. customwas 215° C.
  7. custom40 ml of water was collected, at which time 0.9 g of catalyst compound ATC-I
  8. additionwas added to the flask
  9. customAfter an additional 45 minutes the water of reaction
  10. customwas collected
  11. temperatureHeating
  12. customexcess alcohol removed as the pressure
  13. temperatureThe reaction mixture was cooled to 170° C.
  14. customthe remaining alcohol removed by steam distillation
  15. customduring 2 hours
  16. filtrationThe residue was filtered with a No

Sources & evidence

ORD record
ord-117776e38626424781c14a6963a943ba
Source dataset
uspto-grants-1985_07
Patent number
US04526725

Linked notes

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