Hydrochloric Acid → Bicyclo[2.2.1]hept-2-ene, polymer with ethene

HRID 1837784Notes

Reaction equation

HRID 1837784 reaction equation
[CH:1]12CC(CC1)C=[CH:2]2.[C:8]1([CH3:14])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C=C.CO.Cl>C1(C)C=CC=CC=1.[Cr]>[CH2:1]=[CH2:2].[CH:8]12[CH2:14][CH:11]([CH2:12][CH2:13]1)[CH:10]=[CH:9]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 6325EthyleneHCID 86759525Norbornene toluene

Product 1

HCID 168460Bicyclo[2.2.1]hept-2-ene, polymer with ethene

Reagents, catalysts & solvents 2

HCID 23976ChromiumCatalystHCID 1140TolueneSolvent2×

Procedure

First of all, 0.200 mmole of the chromium compound from Example 5 was suspended in 50 mL of toluene. This solution was then put into a 250-mL glass autoclave. Subsequently, 40 mL of a norbornene-toluene solution (318.60 mmoles of norbornene) were added to this solution. The reaction mixture thus obtained was first brought to a temperature of 0° C. [32° F.] and subsequently saturated with ethene for 30 minutes at 3 bar. Then the reaction was started by adding 1.34 g of MAO (Cr:Al=1:50) dissolved in 20 mL of toluene. After a reaction time of 1.5 hours, the reaction was interrupted by dripping the polymerization mixture into a mixture of methanol and hydrochloric acid. The polymer precipitate obtained in this process was filtered off, washed with methanol and dried in a vacuum at 70° C. [158° F.]. The yield was 28 g of a polymer having a Tg of 128° C. [262.4° F.].

Workup

  1. customThe reaction mixture thus obtained
  2. additionby adding 1.34 g of MAO (Cr:Al=1:50)
  3. customAfter a reaction time of 1.5 hours
  4. customThe polymer precipitate obtained in this process
  5. filtrationwas filtered off
  6. washwashed with methanol
  7. customdried in a vacuum at 70° C. [158° F.]
  8. customa Tg of 128° C. [262.4° F.]

Sources & evidence

ORD record
ord-04f225c7664649fdbdff13255807b5ef
Source dataset
uspto-grants-2004_08
Patent number
US06784261B1

Reaction notes

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