Isoprene → HCID 19842620, compound

HRID 1631416Notes

Reaction equation

HRID 1631416 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.[CH2:22]=[CH:23][C:24](=[CH2:26])[CH3:25]>C1CCCCC1>[CH2:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH2:22]=[CH:23][C:24](=[CH2:25])[CH3:26].[CH2:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 6557Isoprene3×HCID 7501Styrene4×HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 178418339Butyllithium

Product 1

HCID 19842620HCID 19842620, compound

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Conditions

Temperature
40 °C

Procedure

In a pressure resistant reactor, 23.3 kg of cyclohexane, 4.42 millimoles of TMEDA, and 2.20 kg of styrene were added, and while the mixture was stirred at 40° C., 147.2 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., 5.60 kg of isoprene was continuously added to the reactor for 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, while the temperature was controlled to be maintained at 50° C. to 60° C., 2.20 kg of styrene was continuously added over one hour. After completion of the addition of styrene, polymerization was further carried out for one hour, and thus a styrene-isoprene-styrene block copolymer was formed. The polymerization conversion ratio for styrene was 100%. Subsequently, 314.0 millimoles of methanol was added to the reaction liquid as a polymerization terminator. The resulting mixture was thoroughly mixed, and thereby the reaction was terminated. A portion of the reaction liquid thus obtained was taken out and was subjected to the same analyses as in Reference Example 1. These values are presented in Table 2. The subsequent operation was carried out in the same manner as in Reference Example 1, and a composition of Reference Example (styrene-isoprene-styrene block copolymer) 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. temperatureto be maintained at 50° C. to 60° C.
  6. waitwas further carried out for one hour

Sources & evidence

ORD record
ord-57b39693801b42309531f7f958b110bb
Source dataset
uspto-grants-2014_07
Patent number
US08791196B2

Reaction notes

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