Ethanolamine → 5-Methyl-2-Norbornene 1-Hexene

HRID 2163742Notes

Reaction equation

HRID 2163742 reaction equation
[CH2:1]1[CH:5]2[CH:6]3CC=[CH:8][CH:7]3[CH:3]([CH2:4]2)[CH2:2]1.CC1CC2CC1C=C2.C1C2C3CC=CC3C(C2)C1.CC1CC2CC1C=C2.C=CCCCC.C=CCCCC.[I-].C([Al+]CC)C.C(CN)O>C1(C)C=CC=CC=1>[CH3:8][CH:7]1[CH2:6][CH:5]2[CH2:4][CH:3]1[CH:2]=[CH:1]2.[CH2:5]=[CH:1][CH2:2][CH2:3][CH2:7][CH3:6]

Participants

8

Reactant 6

HCID 700EthanolamineHCID 115971-HexeneHCID 95605Dihydrodicyclopentadiene2×HCID 101870Bicyclo[2.2.1]hept-2-ene, 5-methyl-2×HCID 16686130AlEt2IHCID 131711405DHDCPD 5-methyl-2-norbornene 1-hexene

Product 1

HCID 867362545-Methyl-2-Norbornene 1-Hexene

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 1/1 molar ratio of dihydrodicyclopentadiene (DHDCPD) to 5-methyl-2-norbornene was used as follows to prepare the DHDCPD/5-methyl-2-norbornene/1-hexene copolymer of example 2. 2500 ml dry toluene cosolvent, 207.5 ml DHDCPD, 182.5 ml 5-methyl-2-norbornene, 45 ml of the 1-hexene solution, and 30 ml of the diethylaluminum iodide solution were charged to a gallon bottle. 37.5 ml of the MoCl5 solution was charged last with shaking. After 1.5 hours the reaction was shortstopped using a mixture of 5 ml ethanolamine, 15 ml Solution A, and 60 ml of an antioxidant solution (0.1 g/ml of 2,2'-methylenebis-[4-methyl-6-t-butylphenol] in toluene). The polymer was coagulated in several batches using excess Solution A in a Waring blender. About 350 grams of a solid, ring-opened DHDCPD/5-methyl-2-norbornene/1-hexene copolymer was recovered after filtration and vacuum drying. The copolymer was found to have a DSV of about 1.04.

Workup

  1. customAbout 350 grams of a solid, ring-opened DHDCPD/5-methyl-2-norbornene/1-hexene copolymer was recovered
  2. filtrationafter filtration and vacuum
  3. customdrying

Sources & evidence

ORD record
ord-ebabbe31574f41caad125086983a6ed6
Source dataset
uspto-grants-1979_01
Patent number
US04136249

Reaction notes

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