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

HRID 1033259Notes

Reaction equation

HRID 1033259 reaction equation
[CH:1]([CH:3]=[CH:4]C=C)=[CH2:2].[CH2:7]=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C=CC1C=CC=CC=1.C=CC=C.CN(C)CCN(C)C.C([Li])CCC>CCCCCC>[CH2:2]=[CH:1][CH:3]=[CH2:4].[CH2:7]=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 5

HCID 7501StyreneHCID 78451,3-ButadieneHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 86747834HCID 86747834, compoundHCID 178418339Butyllithium

Product 1

HCID 62697Benzene, ethenyl-, polymer with 1,3-butadiene

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A "living" medium vinyl butadiene/styrene copolymer was prepared in accordance with the following procedure: To a stainless steel 5 gallon reactor equipped with a stirrer and thermometer and maintained under a nitrogen atmosphere was charged 309 grams (2.97 moles) of styrene, 1235 grams (22.87 moles) of 1,3-butadiene, 25.4 lbs of hexane, 8.2 millimoles (hereinafter abbreviated as mM) of N,N,N',N'-tetramethylethylene diamine (TMEDA) and 11.86 mM of n-butyllithium initiator. After addition of the ingredients was completed, the temperature of the reaction mixture was controlled at 30°-50° C. for 4.5hours with stirring under positive nitrogen pressure. A sample of the resultant living polymer was quenched with isopropanol and drum dried to serve as a control (designated C1 for convenience). For comparative purposes, a sample of living copolymer was terminated with benzonitrile to serve as an additional control (designated C2 for convenience).

Workup

  1. customwas prepared in accordance with the following procedure
  2. customTo a stainless steel 5 gallon reactor equipped with a stirrer
  3. temperaturethermometer and maintained under a nitrogen atmosphere
  4. additionAfter addition of the ingredients
  5. customwas quenched with isopropanol and drum
  6. customdried
  7. customFor comparative purposes, a sample of living copolymer was terminated with benzonitrile

Sources & evidence

ORD record
ord-ff33f7fcc2414c838eeda5311f61577b
Source dataset
uspto-grants-1994_05
Patent number
US05310798

Reaction notes

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