Styrene → Isobutylene styrene

HRID 1915978

Reaction equation

HRID 1915978 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].CC(=C)C.C=CC1C=CC=CC=1>[Ti](Cl)(Cl)(Cl)Cl.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

7

Reactant 4

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

Product 1

HCID 44154101Isobutylene styrene

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 8005Butyl ChlorideSolvent

Conditions

Temperature
-70 °C

Procedure

In a 2 L reaction vessel equipped with a stirrer, 589 mL of methylcyclohexane (dried over molecular sieves), 613 mL of n-butyl chloride (dried over molecular sieves) and 0.550 g of cumyl chloride were added. After cooling the reaction vessel to −70° C., 0.35 mL of α-picoline(2-methylpyridine) and 179 mL of isobutylene were added. Furthermore, 9.4 mL of titanium tetrachloride was added and polymerization was initiated, and then the solution was reacted for 2.0 hours while stirring at −70° C. Next, 59 mL of styrene was added to the reaction vessel and the reaction was continued for 60 minutes, and then the reaction was terminated by adding a large amount of methanol. After removing the solvent from the reaction solution, a polymer was dissolved in toluene and washed twice with water. This toluene solution was added to the methanol mixture, thereby precipitating a polymer, and the resultant polymer was dried at 60° C. for 24 hours to obtain a styrene-isobutylene diblock copolymer.

Workup

  1. customIn a 2 L reaction vessel
  2. customequipped with a stirrer
  3. custompolymerization
  4. customthe solution was reacted for 2.0 hours
  5. customthe reaction was terminated
  6. additionby adding a large amount of methanol
  7. customAfter removing the solvent from the reaction solution
  8. dissolutiona polymer was dissolved in toluene
  9. washwashed twice with water
  10. additionThis toluene solution was added to the methanol mixture
  11. customprecipitating a polymer
  12. dry with materialthe resultant polymer was dried at 60° C. for 24 hours

Sources & evidence

ORD record
ord-cebef1408a4e4f03882674518c23eea7
Source dataset
uspto-grants-2013_12
Patent number
US08616255B2

Linked notes

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