Isoprene → Isoprene butadiene

HRID 1791963Notes

Reaction equation

HRID 1791963 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH2:7])=[CH:4][CH:3]=1.[CH2:10]=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C([Li])(CC)C.C=CC(=C)C.C=CC=C>C1CCCCC1>[CH2:4]=[CH:3][C:2](=[CH2:1])[CH3:9].[CH2:10]=[CH:11][CH:12]=[CH2:13].[CH3:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH2:7])=[CH:4][CH:3]=1.[CH2:10]=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

8

Reactant 5

HCID 6557IsopreneHCID 7501Styrene2×HCID 78451,3-ButadieneHCID 121611-Ethenyl-4-methylbenzene2×HCID 178418400CID 53628100

Product 2

HCID 168288Isoprene butadieneHCID 19702659Styrene p-methylstyrene

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent2×

Procedure

In a pressure-tight case equipped with a stirrer, 2700 g of cyclohexane, 70 g of a 40:60 monomer mixture of p-methylstyrene and styrene, and 2.52 ml of 1.3 mol cyclohexane solution of sec-butyllithium were placed and polymerized at 50° C. for 120 minutes. The resulting mixture was further polymerized with 326.6 g of a 60:40 monomer mixture of isoprene and butadiene for 120 minutes, and was further polymerized with 70 g of a 40:60 monomer mixture of p-methylstyrene and styrene for 120 minutes. The polymerization was then terminated by the addition of methanol and thereby yielded a poly(p-methylstyrene/styrene)-poly(isoprene/butadiene)-poly(p-methylstyrene/styrene) triblock copolymer. The triblock copolymer was dissolved in cyclohexane, and the resulting solution was placed in a pressure-tight case, whose atmosphere had been sufficiently replaced with nitrogen gas. The solution was subjected to hydrogenation using a Ni/Al Ziegler hydrogenation catalysis at 80° C. in an atmosphere of hydrogen gas for 5 hours and thereby yielded a poly(p-methylstyrene/styrene)-hydrogenated poly(isoprene/butadiene)-poly(p-methylstyrene/styrene) triblock copolymer [Mn=200000; proportions of polymer blocks=15/70/15 (by weight); hydrogenation ratio of poly(isoprene/butadiene) block=99% by mole] [addition block copolymer (I0-5a)].

Workup

  1. customIn a pressure-tight case equipped with a stirrer
  2. custompolymerized at 50° C. for 120 minutes
  3. customThe polymerization was then terminated by the addition of methanol

Sources & evidence

ORD record
ord-61df165efc81456c875f291a49f95b22
Source dataset
uspto-grants-2006_07
Patent number
US07074855B2

Reaction notes

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