Stearyl Alcohol → Dioctadecyl benzene-1,4-dicarboxylate

HRID 400311Notes

Reaction equation

HRID 400311 reaction equation
[C:1]([O:13][CH3:14])(=[O:12])[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.C(O)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>>[C:6]([O:8][CH2:9][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH3:16])(=[O:7])[C:5]1[CH:10]=[CH:11][C:2]([C:1]([O:13][CH2:14][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH3:16])=[O:12])=[CH:3][CH:4]=1

Participants

3

Reactant 2

HCID 8221Stearyl AlcoholHCID 8441Dimethyl terephthalate

Product 1

HCID 13314147Dioctadecyl benzene-1,4-dicarboxylateYield 96.2%

Conditions

Temperature
130 °C

Procedure

To a 2 L Buchi reactor equipped with a double turbine agitator and distillation apparatus was charged Dimethyl terephthalate (315.8 grams), Stearyl Alcohol (879.7 grams) and heated to 130° C. under Nitrogen purge for 1 hour, after which stirring was commenced followed by the addition of Tyzor catalyst (3.0 grams, available from Dupont). The reaction mixture was then heated to 145° C., followed by slowly ramping the temperature to 190° C. over a 3-4 hour period such that the evolution of methanol is distilled in a controlled manner. The reaction temperature was maintained at 190° C. for an additional 16 hours until >96% conversion to the product was achieved as determined by 1H NMR spectroscopy. The product was discharged as a low viscosity liquid which solidified on cooling to give a 1050 gram of a white solid (96.2% yield). The product was shown to be pure by 1H NMR spectroscopy with trace amounts of the mono-ester. Physical properties of this compound are shown in Table 2.

Workup

  1. customTo a 2 L Buchi reactor equipped with a double turbine agitator and distillation apparatus
  2. custompurge for 1 hour
  3. additionwas commenced followed by the addition of Tyzor catalyst (3.0 grams, available from Dupont)
  4. temperatureThe reaction mixture was then heated to 145° C.
  5. customto 190° C.
  6. customover a 3-4 hour
  7. distillationis distilled in a controlled manner
  8. temperatureThe reaction temperature was maintained at 190° C. for an additional 16 hours until >96% conversion to the product
  9. temperatureon cooling

Sources & evidence

ORD record
ord-7c9cefd0e4c943f7a4d77c843d4d4589
Source dataset
uspto-grants-2014_06
Patent number
US08741043B2

Reaction notes

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