Methanol → 2-Methylbuta-1,3-diene;styrene

HRID 1888838Notes

Reaction equation

HRID 1888838 reaction equation
CN(CCN(C)C)C.[CH2:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C([Li])CCC.C=CC(=C)C.CO>C1CCCCC1>[CH2:9]=[CH:10][C:11](=[CH2:12])[CH3:16].[CH2:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 5

HCID 887MethanolHCID 6557Isoprene3×HCID 7501Styrene2×HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 178418339Butyllithium

Product 1

HCID 1599892-Methylbuta-1,3-diene;styrene

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Conditions

Temperature
40 °C

Procedure

In a pressure resistant reactor, 23.3 kg of cyclohexane, 1.39 millimoles of TMEDA, and 1.50 kg of styrene were added, and while the mixture was stirred at 40° C., 92.6 millimoles of n-butyllithium was added thereto. While the temperature was elevated to 50° C., polymerization was carried out for one hour. The polymerization conversion ratio for styrene was 100%. Subsequently, while the temperature was controlled to be maintained at 50° C. to 60° C., 8.50 kg of isoprene was continuously added to the reactor over one hour. After completion of the addition of isoprene, polymerization was carried out for another one hour. The polymerization conversion ratio for isoprene was 100%. Thereafter, 185.2 millimoles of methanol was added to the system as a polymerization terminator, the resulting mixture was thoroughly mixed, and the reaction was terminated. Thereby, a styrene-isoprene block copolymer was formed, which would serve as a block copolymer R. A portion of the reaction liquid thus obtained was taken out, and the same analyses as in Production Example 6 were carried out. These values are presented in Table 5. The subsequent operation was carried out in the same manner as in Production Example 6, and a block copolymer composition of Reference Production Example 2 was collected.

Workup

  1. customwas elevated to 50° C.
  2. custompolymerization
  3. temperatureto be maintained at 50° C. to 60° C.
  4. waitwas carried out for another one hour
  5. additionthe resulting mixture was thoroughly mixed
  6. customthe reaction was terminated

Sources & evidence

ORD record
ord-eb485651225e409b9b80dde6a2a04258
Source dataset
uspto-grants-2013_08
Patent number
US08501869B2

Reaction notes

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