Styrene → Isobutylene styrene

HRID 526312Notes

Reaction equation

HRID 526312 reaction equation
[CH3:1][CH:2]1[CH2:7]CCC[CH2:3]1.[C:8](Cl)([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(C)[CH3:9].N1C=CC=CC=1C.CC(=C)C.C=CC1C=CC=CC=1>[Ti](Cl)(Cl)(Cl)Cl.CO.C(Cl)CCC>[CH2:9]=[CH:8][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH3:3][C:2](=[CH2:1])[CH3:7]

Participants

9

Reactant 5

HCID 7501StyreneHCID 7962MethylcyclohexaneHCID 79752-MethylpyridineHCID 8255IsobutyleneHCID 70281(1-Chloro-1-methylethyl)benzene

Product 1

HCID 44154101Isobutylene styrene

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 887MethanolSolventHCID 8005Butyl ChlorideSolvent

Conditions

Temperature
-70 °C

Procedure

Into a 2 L reaction container having an agitator, 589 mL of methylcyclohexane (dried with molecular sieves), 613 ml of n-butyl chloride (dried with molecular sieves), and 0.550 g of cumyl chloride were added. The reaction container was cooled to −70° C., and then 0.35 mL of α-picoline (2-methylpyridine) and 179 mL of isobutylene were added. Further, 9.4 mL of titanium tetrachloride was added to start polymerization. They were reacted with each other for 2.0 hours while stirring the solution at −70° C. Next, 59 mL of styrene was added to the reaction container, and reaction was continued for another 60 minutes. Thereafter, a large amount of methanol was added to stop the reaction. After removing a solvent and the like from the reaction solution, the polymer was dissolved with toluene and rinsed twice. This toluene solution was added to a methanol mixture to precipitate a polymer. The polymer thus obtained was dried at 60° C. for 24 hours, thereby obtaining a styrene-isobutylene diblock copolymer.

Workup

  1. customInto a 2 L reaction container
  2. additionwere added
  3. custompolymerization
  4. customThey were reacted with each other for 2.0 hours
  5. customthe reaction
  6. customAfter removing a solvent
  7. dissolutionthe like from the reaction solution, the polymer was dissolved with toluene
  8. washrinsed twice
  9. additionThis toluene solution was added to a methanol mixture
  10. customto precipitate a polymer
  11. customThe polymer thus obtained
  12. customwas dried at 60° C. for 24 hours

Sources & evidence

ORD record
ord-33458a051763415d9db0f0a2940d31aa
Source dataset
uspto-grants-2016_05
Patent number
US09346227B2

Reaction notes

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