Oxygen → HCID 86739198, compound

HRID 2296075Notes

Reaction equation

HRID 2296075 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH2:3].O=O.[CH:12]([Li])([CH2:14][CH3:15])[CH3:13].[CH2:17]=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C=CC=C.C=CC1C=CC=CC=1.[CH3:37][C:38]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[CH2:39]>C1CCCCC1.CC(O)C.O>[CH2:1]=[CH:2][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:17]=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[CH2:13]=[CH:12][CH:14]=[CH2:15].[CH3:39][C:38]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[CH2:37].[CH3:3][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH2:1]

Participants

10

Reactant 6

HCID 977OxygenHCID 7407Alpha-Methylstyrene2×HCID 7501Styrene3×HCID 78451,3-Butadiene4×HCID 165735Benzene, ethenyl-, polymer with (1-methylethenyl)benzeneHCID 178418400CID 536281002×

Product 1

HCID 86739198HCID 86739198, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3776IsopropanolSolventHCID 8078CyclohexaneSolvent

Procedure

A 1-liter flask was charged with 400 grams of α-methylstyrene. In order to remove residual moisture, oxygen and impurities, 0.42 millimole of secondary butyllithium in cyclohexane was added. The contents of the flask were heated to about 54° centigrade, 12.7 grams of styrene and 0.96 millimole of secondary butyllithium were added. The solution within the flask turned red in color and the temperature rose 5 degrees above that of the water bath in 11/2 minutes. One and one-half minutes after the addition of the styrene, 45 grams of 1,3-butadiene were added and the reaction mixture color changed from red to light orange and then yellow. The water bath temperature was maintained between about 40° and 60° centigrade. About 110 minutes after the addition of the butadiene monomer, the polymerization mixture color changed to red, indicating completion of the butadiene block and start of polymerization of another styrene-α-methylstyrene copolymer block. About 30 minutes after the second appearance of red color, 1 milliliter of propanol-2 was added to terminate polymerization. The product was isolated as in Example 7. 79 Grams of a thermoplastic elastomer was obtained which was about 100 percent triblock copolymer. The molecular weight as determined by gel permeation chromatography was 92,000 grams per mole. The weight composition was 57 percent butadiene, 16 percent styrene, and 27 percent α-methylstyrene. Product physical properties as determined from compression molded samples were: tensile rupture strength 3070 pounds per square inch, and elongation at break 740 percent.

Workup

  1. additionwas added
  2. additionwere added
  3. customrose 5 degrees
  4. custom2 minutes
  5. additionwere added
  6. customto terminate
  7. custompolymerization
  8. customThe product was isolated as in Example 7
  9. custom79 Grams of a thermoplastic elastomer was obtained which

Sources & evidence

ORD record
ord-a4eddf66196146f4aa40c2f87fc6640a
Source dataset
uspto-grants-1984_01
Patent number
US04427837

Reaction notes

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