Styrene → Benzene, ethenyl-, polymer with 1,3-butadiene

HRID 485738

Reaction equation

HRID 485738 reaction equation
[CH2:1]=[CH:2][CH:3]=[CH2:4].[CH2:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C1C=CC(P(C2C=CC=CC=2)(C2C=CC=CC=2)=O)=CC=1.C([Li])CCC.[C:38]([C:42]1[C:47](C)=[CH:46][CH:45]=[C:44](O)[C:43]=1C(C)(C)C)(C)(C)[CH3:39]>CCCCCC.C(O)(C)C>[CH2:1]=[CH:2][CH:3]=[CH2:4].[CH2:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH2:39]=[CH:38][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

Participants

9

Reactant 5

HCID 7501StyreneHCID 78451,3-ButadieneHCID 13097Triphenylphosphine OxideHCID 3034427Phenol, bis(1,1-dimethylethyl)-4-methyl-HCID 178418339Butyllithium

Product 2

HCID 7501StyreneYield 19.4%HCID 62697Benzene, ethenyl-, polymer with 1,3-butadieneYield 40.9%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8058HexaneSolvent

Procedure

A one gallon stainless steel reactor equipped with a stirrer blade is charged with 95 grams of 1,3-butadiene and 19 grams of styrene in 2,000 grams of n-hexane. One-half millimoles of TPPO are added and the temperature is adjusted to 100° C. One millimole of n-butyllithium is added to the mixture in the reaction vessel. Polymerization is completed within 30 minutes with the final maximum reaction temperature reaching 130° C. After termination of the reaction, 0.5 percent by weight of an antioxidant, di-tert-butyl-p-cresol ("IONOL"), based on the reaction mixture, is added to the mixture which is coagulated in isopropanol and drum dried to remove the solids. The initial monomer charge underwent a 93 percent conversion to form the product butadiene-styrene copolymer containing 40.9 percent of 1,2-microstructure and 19.4 percent of styrene as determined by IR spectroscopy.

Workup

  1. customA one gallon stainless steel reactor equipped with a stirrer blade
  2. customis adjusted to 100° C
  3. customPolymerization
  4. customreaching 130° C
  5. additionis added to the mixture which
  6. customdrum dried
  7. customto remove the solids
  8. additionThe initial monomer charge underwent a 93 percent conversion

Sources & evidence

ORD record
ord-9553bc95d6e64b4bb0b86d903f6659f1
Source dataset
uspto-grants-1985_08
Patent number
US04537939

Linked notes

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