Carbon Dioxide → Benzene, ethenyl-, polymer with 1,3-butadiene

HRID 1902356Notes

Reaction equation

HRID 1902356 reaction equation
C(=O)=O.[CH2:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C=CC=C.C([Li])CCC>CCCCCC>[CH2:4]=[CH:5][CH:6]=[CH2:7].[CH2:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 7501StyreneHCID 78451,3-Butadiene2×HCID 178418339Butyllithium

Product 1

HCID 62697Benzene, ethenyl-, polymer with 1,3-butadieneYield 18.8%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A one-liter round bottom flask is equipped with a dry ice cooled reflux condenser and an agitator. The vessel is provided with a nitrogen atmosphere and charged with 318 grams of purified styrene and 170 grams of purified butadiene. The contents of the flask were at ambient temperature (about 22° C.). The polymerization was initiated by the addition of 2 milliliters of a 0.523 normal solution of n-butyllithium in hexane. The polymerization temperature in the flask varied from about 14° C. to 24° C. and was governed by the refluxing rate of the butadiene from the reaction mixture. The polymerization was terminated 5 hours after the addition of the n-butyllithium by the addition of about 0.2 milliliters of n-propanol. The polymer was recovered by precipitation with methanol to yield 45.5 grams of a rubbery styrene-butadiene polymer. The yield was 9.3 weight percent based on the weight of the initial monomers. Gel permeation chromatography was employed to determine the molecular weight using both an ultraviolet and refractive index detectors. The molecular weight was 187,000 grams per mole and the polymer contained 14.9 percent styrene and 85.1 percent butadiene, percentages being weight percentages. Employing the reactivity ratios reported by Hsieh and Glaze (Rubber Chem. Tech., 43, 22, 1970), wherein the reactivity ratio for styrene was taken at 0.1 and that for butadiene as 12.5, the calculated composition was 14.5 percent styrene and 85.5 percent butadiene.

Workup

  1. temperaturecooled
  2. temperaturereflux condenser
  3. customThe vessel is provided with a nitrogen atmosphere
  4. customwere at ambient temperature
  5. custom(about 22° C.)
  6. customvaried from about 14° C. to 24° C.
  7. customThe polymerization was terminated 5 hours
  8. additionafter the addition of the n-butyllithium
  9. additionby the addition of about 0.2 milliliters of n-propanol
  10. customThe polymer was recovered by precipitation with methanol

Sources & evidence

ORD record
ord-81c820f04e2442f18af2ccb807d86850
Source dataset
uspto-grants-1982_12
Patent number
US04362849

Reaction notes

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