Propylene Oxide → HCID 86737985, compound

HRID 2198957Notes

Reaction equation

HRID 2198957 reaction equation
[CH2:1]=[CH:2][CH:3]=[CH2:4].[CH2:5]1O[CH:6]1[CH3:7].[C:9]1(=[O:16])[O:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1>C1CCCCC1>[CH2:1]=[CH:2][CH:3]=[CH2:4].[CH2:7]=[CH:6][C:5]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:9]1(=[O:16])[O:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 6378Propylene OxideHCID 78451,3-Butadiene2×HCID 10401epsilon-CAPROLACTONE2×

Product 1

HCID 86737985HCID 86737985, compound

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

Cyclohexane was charged to a 26-oz. beverage bottle equipped with a perforated Crown cap over a self-sealing rubber gasket, and the bottle and cyclohexane were then purged with nitrogen. Styrene and tetrahydrofuran and then the n-butyllithium were added. The temperature was adjusted to 70° C. and the bottle and its contents were tumbled in a constant temperature bath for 20 minutes, after which time the styrene polymerization was essentially complete. 1,3-Butadiene was then charged to the bottle and the polymerization was continued for one hour with continued agitation at 70° C. At the end of this time, polymerization of the butadiene was essentially complete. Propylene oxide was then added to the polymerization reaction mixture and the mixture was agitated for 10 minutes while the temperature was reduced from 70° C. to 30° C. Epsilon-caprolactone was added and polymerization proceeded for 10 minutes with continued agitation. Promptly 10 minutes after the epsilon-caprolactone had been charged, the polymerization reaction was terminated by adding the chosen terminating agent. The reaction mixture and added terminating agent were thoroughly mixed by shaking the beverage bottle to insure quantitative termination of all polymer lithium. One part of 2,6-di-t-butyl-4-methylphenol per hundred parts of total monomer was added as a 10 weight percent solution in 50:50 toluene:isopropanol. The contents of the bottle were emptied into a beaker, and the styrene-butadiene-epsilon-caprolactone block terpolymer was isolated by steam stripping. The recovered polymer was dried at 60° C. for about 15 hours under reduced pressure. Block polycaprolactone was determined for each polymer by an oxidative degradation method as described in Footnote (b) of Table II.

Workup

  1. customequipped with a perforated Crown
  2. customcap over a self-sealing rubber gasket
  3. customthe bottle and cyclohexane were then purged with nitrogen
  4. additionStyrene and tetrahydrofuran and then the n-butyllithium were added
  5. customwas adjusted to 70° C.
  6. customafter which time the styrene polymerization
  7. waitthe polymerization was continued for one hour with continued agitation at 70° C
  8. customwas reduced from 70° C. to 30° C
  9. custompolymerization
  10. waitproceeded for 10 minutes with continued agitation
  11. customthe polymerization reaction
  12. customwas terminated
  13. additionby adding the
  14. customchosen terminating agent
  15. additionThe reaction mixture and added
  16. customterminating agent
  17. additionwere thoroughly mixed
  18. stirringby shaking the beverage bottle
  19. additionOne part of 2,6-di-t-butyl-4-methylphenol per hundred parts of total monomer was added as a 10 weight percent solution in 50:50 toluene

Sources & evidence

ORD record
ord-6c7a875fb8554771a5dd9fda9abed9be
Source dataset
uspto-grants-1982_11
Patent number
US04360643

Reaction notes

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