2-Ethylhexyl acrylate → Octinoxate

HRID 1073681Notes

Reaction equation

HRID 1073681 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[CH2:10]([CH:12]([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:13][O:14][C:15](=[O:18])[CH:16]=[CH2:17])[CH3:11]>[Pd].C(N(CC)CC)C>[CH3:22][CH2:21][CH2:20][CH2:19][CH:12]([CH2:13][O:14][C:15](/[CH:16]=[CH:17]/[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1)=[O:18])[CH2:10][CH3:11]

Participants

5

Reactant 2

HCID 76362-Ethylhexyl acrylateHCID 696764-Iodoanisole

Product 1

HCID 5355130Octinoxate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
142.5 °C

Procedure

Charge 6.8 gallons of molten 4-iodoanisole from step 1, 11.4 gallons 2-ethylhexylacrylate (83.8 pounds), 7.3 gallons triethylamine (44 pounds), and 0.6 pounds of 5% palladium on carbon catalyst (dry) to a 50 gallon tank. With good agitation, begin heating. Heat to 100° -105° C. to reflux. The reflux temperature will gradually increase to about 140-145° C. The total time of reaction above 100° C. will be about 2-4 hours. After the reaction is complete, as determined by gas chromatography, cool the reaction mixture to 25° -30° C. Filter to collect the palladium catalyst and the resulting triethylamine hydroiodide salt. Wash the filtered product with 20 gallons of water to remove any soluble salt. Allow the phases to separate. The top organic product phase is ready for distillation. Its volume is about 15 gallons containing about 119 pounds of product.

Workup

  1. temperatureWith good agitation, begin heating
  2. temperatureHeat to 100° -105° C.
  3. temperatureto reflux
  4. customThe total time of reaction above 100° C.
  5. temperaturecool the reaction mixture to 25° -30° C
  6. filtrationFilter
  7. customto collect the palladium catalyst
  8. washWash the filtered product with 20 gallons of water
  9. customto remove any soluble salt
  10. customto separate
  11. distillationThe top organic product phase is ready for distillation
  12. additioncontaining about 119 pounds of product

Sources & evidence

ORD record
ord-fec42445316846c7a1b967665ffb73da
Source dataset
uspto-grants-1990_11
Patent number
US04970332

Reaction notes

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