Isoprene → HCID 19842620, compound

HRID 2039308Notes

Reaction equation

HRID 2039308 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

To a pressure-resistant reactor, 23.3 kg of cyclohexane, 1.3 millimoles of TMEDA and 0.90 kg of styrene were added and stirred at 40° C. Added thereto was 90.0 millimoles of n-butyl lithium, and while the temperature was increased to 50° C., the mixture was polymerized for 1 hour. The degree of polymerization conversion of styrene was 100%. Subsequently, 8.10 kg of isoprene was added to the reactor continuously over 1 hour while the temperature was controlled to maintain 50 to 60° C. After the addition of isoprene was completed, the polymerization was performed for additional 1 hour. The degree of polymerization conversion of isoprene was 100%. Subsequently, 0.90 kg of styrene was added thereto continuously over 1 hour while the temperature was controlled to maintain 50 to 60° C. After the addition of styrene was completed, the polymerization was performed for additional 1 hour to produce a styrene-isoprene-styrene block copolymer. The degree of polymerization conversion of styrene was 100%. After that, 180.0 millimoles of methanol was added as a polymerization terminator and mixed well to terminate the reaction. Part of the reaction solution obtained was extracted and subjected to the same measurements as Preparation example 1. The values thereof are shown in Table 2. Subsequent treatments that were the same as those of Preparation example 1 were carried out to recover the block copolymer composition of Preparation example 6.

Workup

  1. additionAdded
  2. temperaturewhile the temperature was increased to 50° C.
  3. customthe mixture was polymerized for 1 hour
  4. temperatureto maintain 50 to 60° C
  5. waitcontinuously over 1 hour while the temperature was controlled
  6. temperatureto maintain 50 to 60° C
  7. waitthe polymerization was performed for additional 1 hour

Sources & evidence

ORD record
ord-7bbb121a4a62411cab2a293ae072b233
Source dataset
uspto-grants-2013_11
Patent number
US08578852B2

Reaction notes

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