Propylene Oxide → HCID 86737985, compound

HRID 1577284Notes

Reaction equation

HRID 1577284 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 were added and then the n-butyllithium was added. The temperature was adjusted to 70° C. and the bottle and its contents were tumbled in a constant temperature bath for 20 to 30 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 1,3-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 was allowed to proceed at 30° C. for 5 minutes with continued agitation. Five minutes after the epsilon-caprolactone had been charged, the polymerization reaction was terminated by the addition of 10 ml of 0.1 M hydrochloric acid. After termination was complete, one part of 2,6-di-t-butyl-4-methylphenol per 100 parts of total monomers 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. Properties of the recovered polymers are shown in 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 were added
  5. additionthe n-butyllithium was added
  6. customwas adjusted to 70° C.
  7. customafter which time the styrene polymerization
  8. waitthe polymerization was continued for one hour with continued agitation at 70° C
  9. customwas reduced from 70° C. to 30° C
  10. custompolymerization
  11. waitto proceed at 30° C. for 5 minutes with continued agitation
  12. customthe polymerization reaction
  13. customwas terminated by the addition of 10 ml of 0.1 M hydrochloric acid
  14. additionone part of 2,6-di-t-butyl-4-methylphenol per 100 parts of total monomers was added as a 10 weight percent solution in 50:50 toluene

Sources & evidence

ORD record
ord-ccdd504262444677ad8026b7b30cc33f
Source dataset
uspto-grants-1981_09
Patent number
US04287313

Reaction notes

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