Methyl Methacrylate → Methyl Methacrylate

HRID 2232575Notes

Reaction equation

HRID 2232575 reaction equation
Cl.[C:2]([C:5]1[O:6]C(=O)[C:8](=[O:10])[N:9]=1)([CH3:4])=[CH2:3].[C:12]([O:17][CH3:18])(=[O:16])[C:13]([CH3:15])=[CH2:14].[C:19]([O:23][CH2:24][CH2:25][CH2:26][CH3:27])(=[O:22])[CH:20]=[CH2:21].N(C(C)(CC(C)C)C#N)=NC(C)(CC(C)C)C#N>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:5]([N:9]=[C:8]=[O:10])(=[O:6])[C:2]([CH3:4])=[CH2:3].[C:12]([O:17][CH3:18])(=[O:16])[C:13]([CH3:15])=[CH2:14].[C:19]([O:23][CH2:24][CH2:25][CH2:26][CH3:27])(=[O:22])[CH:20]=[CH2:21]

Participants

9

Reactant 4

HCID 6658Methyl MethacrylateHCID 8846Butyl AcrylateHCID 915372,2'-Azobis(2,4-dimethylvaleronitrile)HCID 221576152-Isopropenyloxazoline-4,5-dione hydrochloride

Product 3

HCID 6658Methyl MethacrylateHCID 8846Butyl AcrylateHCID 10942374METHACRYLOYL ISOCYANATE

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-isopropenyloxazoline-4,5-dione hydrochloride (15 g), methyl methacrylate (20 g), n-butyl acrylate (15 g), 2,2'-azobis(2,4-dimethylvaleronitrile) (1.25 g) and ethyl acetate (25 g) was dropwise added to toluene (50 g) heated at 100° C. in 90 minutes while stirring. Stirring was further continued for 5 hours, whereby a copolymer of methacryloyl isocyanate with methyl methacrylate and n-butyl acrylate was produced. Viscosity, C-D (determined by Gardner bubble viscometer). Non-volatile content, 40%. Mw, 7100 (determined by gel permeation chromatography).

Workup

  1. stirringStirring

Sources & evidence

ORD record
ord-3d8e3aafe4454a52a93900f66222f877
Source dataset
uspto-grants-1988_11
Patent number
US04788256

Reaction notes

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