N,N,N',N'-Tetramethylethylenediamine → Benzene, ethenyl-, polymer with 1,3-butadiene

HRID 1591852Notes

Reaction equation

HRID 1591852 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].CN(CCN(C)C)C.[CH2:14]([Li])[CH2:15][CH2:16][CH3:17].CN(CCN(C)C)C>>[CH2:1]=[CH:2][CH:3]=[CH2:4].[CH2:4]=[CH:3][C:2]1[CH:1]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 178418339ButyllithiumHCID 178483778HCID 178483778, compound

Product 1

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

Procedure

The procedure described in Example 1 was utilized in this example except that 3 mL of 1 M solution of n-butyl lithium (n-BuLi) in hexanes and 5 mL of 1 M solution of TMEDA in hexanes were added to the catalyst system (BaTHFA/MgR2) making the molar ratio (BaTHFA/MgR2/n-BuLi/TMEDA) 1:3:3:5. The styrene-butadiene produced was determined to have a glass transition temperature (Tg) at −76° C. and a melting temperature (Tm) at −11° C. The Mooney viscosity (ML-4) at 100° C. was 48. The GPC measurements indicated that the polymer has a number average molecular weight (Mn) of 175,000 g/mol and a weight average molecular weight (Mw) of 270,000 g/mol. The polydispersity (Mw/Mn) of the resulting polymer was 1.54. Carbon-13 NMR analysis showed a trans 1,4 polybutadiene content of 75%, cis 1,4 polybutadiene content of 19%, a 1,2 polybutadiene content of 6%, and a polystyrene content of 16.5%.

Workup

  1. additionwere added to the catalyst system (BaTHFA/MgR2)

Sources & evidence

ORD record
ord-d46450871f2a4fe9bb6b83dab27d4659
Source dataset
uspto-grants-2007_11
Patent number
US07291687B1

Reaction notes

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