Azobisisobutyronitrile → 2-Butyl norbornene methyl acrylate

HRID 736579

Reaction equation

HRID 736579 reaction equation
[CH2:1]([C:5]1[CH:6]2[CH2:11][CH:9]([CH:10]=1)[CH2:8][CH2:7]2)[CH2:2][CH2:3][CH3:4].[C:12]([O:16][CH3:17])(=[O:15])[CH:13]=[CH2:14].CC(N=NC(C#N)(C)C)(C#N)C.CC[Al](Cl)CC.CC[Al](Cl)Cl.Cl.CO>C1(C)C=CC=CC=1>[CH2:1]([C:5]1[CH:6]2[CH2:11][CH:9]([CH:10]=1)[CH2:8][CH2:7]2)[CH2:2][CH2:3][CH3:4].[C:12]([O:16][CH3:17])(=[O:15])[CH:13]=[CH2:14]

Participants

7

Procedure

2-butylnorbornene (16.8 g, 112 mmol), methyl acrylate (5 mL, 56 mmol), and AIBN (0.28 g, 1.68 mmol) were charged into a 250 mL Schlenk flask and dissolved in 30 mL of toluene. Ethylaluminum sesquichloride (15.2 g; 61.6 mmol) was charged into a 100 mL flask and dissolved in 20 mL of toluene. The toluene solution of ethylaluminum sesquichloride was slowly dropped to the 250 mL Schlenk flask at −70° C. The reaction temperature was raised to room temperature while stirring the mixture for 2 hours, and then the reaction was performed at 65° C. for 12 hours. The reaction solution turned to light green in color during the reaction. After the reaction was completed, the reaction solution was slowly dropped to 3000 cc of 5% v/v HCl—MeOH to precipitate a white polymer, which was filtered through a glass filter and dried in a vacuum oven at 70° C. for 12 hours to obtain a 2-butyl norbornene-methyl acrylate copolymer (5 g: 38.0% by weight based on the total weight of used monomers). The copolymer had a Tg of 100° C., a molecular weight (Mw) of 8,180, and Mw/Mn of 3.2.

Workup

  1. waitthe reaction was performed at 65° C. for 12 hours
  2. customduring the reaction
  3. customto precipitate a white polymer, which
  4. filtrationwas filtered through a glass
  5. filtrationfilter
  6. customdried in a vacuum oven at 70° C. for 12 hours

Sources & evidence

ORD record
ord-2f7f7c70656e42ffa2d7d9d2065d9352
Source dataset
uspto-grants-2009_09
Patent number
US07595369B2

Linked notes

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