Propylene Oxide → HCID 86738130, compound

HRID 1155559Notes

Reaction equation

HRID 1155559 reaction equation
C1OC1C.[C:5]1(=[O:12])[O:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1>C1CCCCC1>[CH2:5]=[CH:6][CH:7]=[CH2:8].[C:5]1(=[O:12])[O:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 6378Propylene OxideHCID 10401epsilon-CAPROLACTONE2×

Product 1

HCID 86738130HCID 86738130, 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 then purged with nitrogen. 1,3-Butadiene and tetrahydrofuran were added and then the n-butyllithium. The temperature was adjusted to 70° C. and the bottle and its contents tumbled in a constant temperature bath for one hour, after which time the 1,3-butadiene polymerization was essentially complete. Propylene oxide was then added to the polymerization reaction mixture and the mixture agitated for 10 minutes while reducing the temperature from 70° C. to 30° C. ε-Caprolactone was added and polymerization conducted at 30° C. for 10 minutes with continued agitation. Promptly 10 minutes after the ε-caprolactone had been charged, the polymerization reaction was terminated by adding 10 ml. of 0.1 M hydrochloric acid and thoroughly mixing the reaction mixture by hand-shaking the beverage bottle. One part by weight of 2,6-di-t-butyl-4-methylphenol per hundred parts by weight of total monomers was added as a 10 weight percent solution in 50:50 toluene:isopropanol and the contents of the bottle then emptied into a beaker of water and the butadiene-ε-caprolactone block copolymer isolated by steam stripping. The recovered polymer was dried at 60° C. for about 15 hrs. under reduced pressure. The calculated molecular weight of this polymer based on the relative amounts of initiator and monomers used was about 33,000.

Workup

  1. customequipped with a perforated crown
  2. customcap over a self-sealing rubber gasket
  3. customthe bottle and cyclohexane then purged with nitrogen
  4. addition1,3-Butadiene and tetrahydrofuran were added
  5. customwas adjusted to 70° C.
  6. customafter which time the 1,3-butadiene polymerization
  7. customfrom 70° C. to 30° C.
  8. additionwas added
  9. custompolymerization
  10. waitconducted at 30° C. for 10 minutes with continued agitation
  11. customthe polymerization reaction
  12. customwas terminated
  13. additionby adding 10 ml
  14. additionof 0.1 M hydrochloric acid and thoroughly mixing the reaction mixture
  15. stirringby hand-shaking the beverage bottle
  16. additionOne part by weight of 2,6-di-t-butyl-4-methylphenol per hundred parts by weight of total monomers was added as a 10 weight percent solution in 50:50 toluene

Sources & evidence

ORD record
ord-6d732810378c4a75b457f46e421331e4
Source dataset
uspto-grants-1981_11
Patent number
US04302576

Reaction notes

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