1-Hexene → 5-Octyl-2-Norbornene 1-Hexene

HRID 2163735Notes

Reaction equation

HRID 2163735 reaction equation
[CH2:1]([CH:9]1[CH2:14][CH:13]2[CH2:15][CH:10]1[CH:11]=[CH:12]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH2:16]=[CH:17][CH2:18][CH2:19][CH2:20][CH3:21].[I-].C([Al+]CC)C>C1(C)C=CC=CC=1>[CH2:1]([CH:9]1[CH2:14][CH:13]2[CH2:15][CH:10]1[CH:11]=[CH:12]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH2:16]=[CH:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 115971-HexeneHCID 15701270Bicyclo[2.2.1]hept-2-ene, 5-octyl-HCID 16686130AlEt2I

Product 1

HCID 867362615-Octyl-2-Norbornene 1-Hexene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

50 ml dry toluene cosolvent, 7 ml 5-octyl-2-norbornene (containing about 15 wt.% dicyclopentadiene trimer impurity), 8 ml 1-hexene solution, and 0.6 ml diethylaluminum iodide solution were charged to a dry nitrogen-purged 7 oz. bottle. 0.75 ml of the MoCl5 solution was charged last. After about 1 hour the reaction was shortstopped using a mixture of ethanolamine, Solution A and 2 ml of an antioxidant solution (0.1 g/ml of 2,2'-methylenebis[4-methyl-6-t-butylphenol] in toluene). The polymer cement was coagulated using excess Solution A in a Waring blender. The solid recovered after being filtered and vacuum dried at 60° C. was found to be a terpolymer of octylnorbornene, dicyclopentadiene trimer and 1-hexene. Tg was measured and the value adjusted to compensate for the trimer impurity.

Workup

  1. custompurged 7 oz. bottle
  2. addition0.75 ml of the MoCl5 solution was charged last
  3. additiona mixture of ethanolamine, Solution A and 2 ml of an antioxidant solution (0.1 g/ml of 2,2'-methylenebis[4-methyl-6-t-butylphenol] in toluene)
  4. customThe solid recovered
  5. filtrationafter being filtered
  6. customvacuum dried at 60° C.

Sources & evidence

ORD record
ord-2fc9189d04f148d58f07631b68fbe9ea
Source dataset
uspto-grants-1979_01
Patent number
US04136248

Reaction notes

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