Methyl Acrylate → HCID 86735943, compound

HRID 2419836Notes

Reaction equation

HRID 2419836 reaction equation
[Cl-].[Cl-].C([Al+2])C.[CH3:6][CH:7]([CH3:11])[CH2:8][CH:9]=[CH2:10].[C:12]([O:16][CH3:17])(=[O:15])[CH:13]=[CH2:14]>C(O)(C)C.CCCCCC.C(OCC)(=O)C>[CH3:6][CH:7]([CH3:11])[CH2:8][CH:9]=[CH2:10].[C:12]([O:16][CH3:17])(=[O:15])[CH:13]=[CH2:14]

Participants

7

Reactant 3

HCID 7294Methyl AcrylateHCID 127244-Methyl-1-penteneHCID 16686341Ethyl aluminium dichloride2×

Product 1

HCID 86735943HCID 86735943, compound

Reagents, catalysts & solvents 3

HCID 3776IsopropanolSolventHCID 8058HexaneSolvent3×HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

A 2-liter six-necked separable polymerization flask equipped with a vane-type stirring rod connected to a motor controllable as to its rotating speed, a condenser, a thermometer, a stopper cock and two metering pumps was disposed in a constant-temperature tank including a temperature controlling device, and the inside of the flask was thoroughly purged with nitrogen. 1065 ml of n-hexane and 35 millimoles of ethyl acetate were fed to the flask in an atmosphere of nitrogen, mixed, and cooled to 0° C. To the resulting solution was slowly added dropwise 17.5 millimoles of ethylaluminum dichloride with stirring over the course of 5 minutes. After the addition, the mixed solution was allowed to stand for 1 hour with stirring in order to complete the formation of a complex between ethylaluminum dichloride and ethyl acetate. The mixture was then heated to 10° C, and at this temperature, 298.0 g of an equimolar mixture of 4-methyl-1-pentene and methyl acrylate, and 300 ml of a 0.03 mole/liter n-hexane solution of tert-butyl peroxy isobutyrate were fed for 5 hours at fixed rates using the two metering pumps so that the total amount of the two monomers in the reaction system became not more than 2 moles/liter of the solvent. Soon after this feeding began, fine polymer particles were formed and came afloat in the reaction system. These particles gradually increased in number and size with the lapse of time. After the end of addition, the polymerization system was maintained for an additional 15 hours at 10° C with stirring. After the end of polymerization, 200 ml of a 10% by volume n-hexane solution of isopropyl alcohol was added to the reaction mixture to decompose the catalyst. In the stirred state, a great amount of the polymer formed ws dispersed and suspended inthe form of granules in the polymerization system. Mere filtration of the reaction mixture could result in the recovery of the polymer particles. The polymer particles were thoroughly washed with n-hexane, and dried at 30° under reduced pressure to afford 158 g of a 4-methyl-1-pentene/methyl acrylate copolymer.

Workup

  1. customA 2-liter six-necked separable polymerization flask equipped with a vane-type
  2. customthe inside of the flask was thoroughly purged with nitrogen
  3. additionmixed
  4. stirringwith stirring over the course of 5 minutes
  5. additionAfter the addition
  6. stirringwith stirring in order
  7. temperatureThe mixture was then heated to 10° C
  8. customfine polymer particles were formed
  9. temperatureThese particles gradually increased in number and size with the lapse of time
  10. additionAfter the end of addition
  11. temperaturethe polymerization system was maintained for an additional 15 hours at 10° C
  12. stirringwith stirring
  13. additionwas added to the reaction mixture
  14. customIn the stirred state, a great amount of the polymer formed ws
  15. additiondispersed
  16. filtrationMere filtration of the reaction mixture
  17. customcould result in the recovery of the polymer particles
  18. washThe polymer particles were thoroughly washed with n-hexane
  19. customdried at 30° under reduced pressure

Sources & evidence

ORD record
ord-2e36e904e12f48e294aee5d8f8e07dc6
Source dataset
uspto-grants-1978_08
Patent number
US04107418

Reaction notes

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