Carbon Dioxide → HCID 19842620, compound

HRID 2211195Notes

Reaction equation

HRID 2211195 reaction equation
[CH2:1]=[CH:2][C:3](=[CH2:5])[CH3:4].[CH2:6]=[CH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(=O)=O.[C:17]([C:21]1[CH:26]=[C:25](C)[CH:24]=[C:23](C(C)(C)C)[C:22]=1O)(C)(C)[CH3:18]>CC(O)C.C1CCCCC1>[CH2:6]=[CH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:1]=[CH:2][C:3](=[CH2:4])[CH3:5].[CH2:18]=[CH:17][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 6557IsopreneHCID 7501Styrene2×HCID 314042,6-Di-tert-butyl-4-methylphenol

Product 1

HCID 19842620HCID 19842620, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8078CyclohexaneSolvent

Procedure

The same 1.3-liter reactor described in Example 1 was used. To the reactor, 675 mL of cyclohexane was added and deaired. Then 125 mL of distilled isoprene was added by syringe. After mixing well, a 50 mL aliquot of the feed was withdrawn by a syringe and transferred into a nitrogen-filled flask for the purpose of determining the amount of residual impurities in the mixture. The DFI solution was added dropwise to the aliquot until a light orange color was apparent. From this external titration result, the amount of DFI required to react with the impurities in the feed in the reactor (blanking) was calculated to be 0.02 mmole. Since the impurity level was so low, no blanking was made. The temperature controller of the heating jacket was set at 55° C. When the solution temperature reached about 52° C., 10.8 mL of the above-prepared DFI solution (containing 0,794 mmole DFI) was added. A nitrogen pressure of 8-14 psi (55.1 to 96.5 kPa) was maintained in the head space of the reactor during the entire polymerization. About 56 minutes after the addition of the DFI solution, 15 mL of styrene was added by syringe. About 34 minutes after the addition of styrene, 2 mL of 2-propanol was added to terminate the polymerization. The polymer solids in the syrup was about 15.7 percent w/w as calculated from material balance. The cooled polymer solution was discharged from the reactor, treated with CO2 and 0.9 grams of 2,6-ditertiarybutyl-4-methylphenol antioxidant was added. The polymer was recovered by vacuum devolatilization at an oven temperature of 190° C. for about 50 minutes. The polymer was analyzed and its properties tested. The results are compiled in Table I.

Workup

  1. additionAfter mixing well
  2. customa 50 mL aliquot of the feed was withdrawn by a syringe
  3. additionfilled flask for the purpose
  4. additionThe DFI solution was added dropwise to the aliquot until a light orange color
  5. customFrom this external titration result
  6. customto react with the impurities in the feed in the reactor (blanking)
  7. customwas set at 55° C
  8. customreached about 52° C.
  9. temperatureA nitrogen pressure of 8-14 psi (55.1 to 96.5 kPa) was maintained in the head space of the reactor during the entire polymerization
  10. additionwas added by syringe
  11. additionwas added
  12. customto terminate
  13. customthe polymerization
  14. additionwas added
  15. customThe polymer was recovered by vacuum devolatilization at an oven temperature of 190° C. for about 50 minutes

Sources & evidence

ORD record
ord-2c46040ae25848788dfcfacc37777fd0
Source dataset
uspto-grants-1995_10
Patent number
US05462994

Reaction notes

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