Azobisisobutyronitrile → Methyl Methyacrylate 2-Acetoacetoxyethyl Methacrylate

HRID 1716169Notes

Reaction equation

HRID 1716169 reaction equation
[C:1]([O:6][CH3:7])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:8]([O:13][CH2:14][CH2:15][O:16][C:17](=[O:22])[CH2:18][C:19]([CH3:21])=[O:20])(=[O:12])[C:9]([CH3:11])=[CH2:10].N(C(C)(C)C#N)=NC(C)(C)C#N>C1COCC1>[CH3:4][C:2](=[CH2:3])[C:1]([O:6][CH3:7])=[O:5].[C:8]([O:13][CH2:14][CH2:15][O:16][C:17](=[O:22])[CH2:18][C:19]([CH3:21])=[O:20])(=[O:12])[C:9]([CH3:11])=[CH2:10]

Participants

5

Reactant 3

HCID 6547AzobisisobutyronitrileHCID 6658Methyl MethacrylateHCID 888552-(Acetoacetoxy)ethyl methacrylate

Product 1

HCID 131728346Methyl Methyacrylate 2-Acetoacetoxyethyl Methacrylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In this procedure, 20 g (0.198 mol) methyl methacrylate, 22.30 g (0.0989 mol) 2-acetoacetoxyethyl methacrylate, and 170 g tetrahyrdrofuran (THF) were placed in a 250-ml, 3-necked flask with a nitrogen inlet, condenser, glass stopper, and stir bar. The mixture was stirred until well mixed. Next, 0.4 g 2,2′-azobis(2-methylpropionitrile) (AIBN) were added, and the resulting mixture was stirred until homogeneous. The resulting solution was heated to reflux for 24 hours under a flow of nitrogen. A colorless, viscous liquid was obtained after the reaction period. Thermogravimetric analysis (TGA) showed this to contain 40% copolymer solids.

Workup

  1. stirringThe mixture was stirred
  2. additionuntil well mixed
  3. stirringthe resulting mixture was stirred until homogeneous
  4. temperatureThe resulting solution was heated
  5. temperatureto reflux for 24 hours under a flow of nitrogen
  6. customA colorless, viscous liquid was obtained
  7. customafter the reaction period

Sources & evidence

ORD record
ord-891f4001c3db4dd89c0485262d648c09
Source dataset
uspto-grants-2010_09
Patent number
US07803458B2

Reaction notes

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