Methyl Methacrylate → 2-Propenoic acid, 2-methyl-, butyl ester, polymer with 2-(dimethylamino)ethyl 2-methyl-2-propenoate and methyl 2-methyl-2-propenoate

HRID 620131Notes

Reaction equation

HRID 620131 reaction equation
[C:1]([O:6][CH2:7][CH2:8][N:9]([CH3:11])[CH3:10])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:12]([O:17][CH3:18])(=[O:16])[C:13]([CH3:15])=[CH2:14].[C:19]([O:24][CH2:25][CH2:26][CH2:27][CH3:28])(=[O:23])[C:20]([CH3:22])=[CH2:21].N(C(C)(CC(C)C)C#N)=NC(C)(CC(C)C)C#N>C1(C)C=CC=CC=1.N(C(C)(CC(C)C)C#N)=NC(C)(CC(C)C)C#N.CCCCCC>[C:1]([O:6][CH2:7][CH2:8][N:9]([CH3:11])[CH3:10])(=[O:5])[C:2]([CH3:4])=[CH2:3].[C:12]([O:17][CH3:18])(=[O:16])[C:13]([CH3:15])=[CH2:14].[C:19]([O:24][CH2:25][CH2:26][CH2:27][CH3:28])(=[O:23])[C:20]([CH3:22])=[CH2:21]

Participants

8

Reactant 4

HCID 6658Methyl MethacrylateHCID 7354Butyl MethacrylateHCID 17869(Dimethylamino)ethyl methacrylateHCID 915372,2'-Azobis(2,4-dimethylvaleronitrile)

Product 1

HCID 1076762-Propenoic acid, 2-methyl-, butyl ester, polymer with 2-(dimethylamino)ethyl 2-methyl-2-propenoate and methyl 2-methyl-2-propenoateYield 136.5%

Reagents, catalysts & solvents 3

HCID 915372,2'-Azobis(2,4-dimethylvaleronitrile)CatalystHCID 1140TolueneSolvent2×HCID 8058HexaneSolvent

Procedure

In a 300 ml, three-necked flask, 12.6 g of N,N-di-methylaminoethyl methacrylate, 24.0 g of methyl methacrylate, 11.4 g of n-butyl methacrylate and 190 ml of toluene were heated to 80° C.-under stirring. A solution of 0.298 g of 2,2'-azobis-(2,4-dimethylvaleronitrile) in 10 ml of toluene was added to the reaction mixture, and the mixture is further heated for 2 hours. Then the same amount of 2,2'-azobis-(2,4-dimethylvaleronitrile) was again added to the reaction mixture, and the mixture was further heated under stirring for 2 hours. The mixture was allowed to stand at room temperature, and was poured into 1 l of n-hexane. The produced precipitate was collected on a filter, washed with two 200 ml portions of n-hexane and dried to obtain 43.7 g (yield: 91%) of the desired polymer as white solid.

Workup

  1. temperaturethe mixture is further heated for 2 hours
  2. temperaturethe mixture was further heated
  3. stirringunder stirring for 2 hours
  4. customto stand at room temperature
  5. customThe produced precipitate was collected on a filter
  6. washwashed with two 200 ml portions of n-hexane
  7. customdried

Sources & evidence

ORD record
ord-1ab75576d77549728527cbe415732c56
Source dataset
uspto-grants-1989_04
Patent number
US04820610

Reaction notes

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