Methacrylic Acid → 3-(Trimethoxysilyl)propyl methacrylate

HRID 1197196Notes

Reaction equation

HRID 1197196 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([CH3:4])=[CH2:3].C[O-].[K+].Cl[CH2:11][CH2:12][CH2:13][Si:14]([O:19][CH3:20])([O:17][CH3:18])[O:15][CH3:16]>CO.C1C=CC(NC2C=CC(NC3C=CC=CC=3)=CC=2)=CC=1.[Cl-].C(C(CCCC)C[N+]1C=CC(N(C)C)=CC=1)C>[C:1]([O:6][CH2:11][CH2:12][CH2:13][Si:14]([O:19][CH3:20])([O:17][CH3:18])[O:15][CH3:16])(=[O:5])[C:2]([CH3:4])=[CH2:3]

Participants

7

Reactant 3

HCID 4093Methacrylic AcidHCID 624493-(Trimethoxysilyl)propyl chlorideHCID 23664618Potassium methoxide

Product 1

HCID 173183-(Trimethoxysilyl)propyl methacrylateYield 92.7%

Reagents, catalysts & solvents 3

HCID 6319N,N'-Diphenyl-P-PhenylenediamineCatalystHCID 11391599Pyridinium, 4-(dimethylamino)-1-(2-ethylhexyl)-, chlorideCatalystHCID 887MethanolSolvent

Conditions

Temperature
125 °C

Procedure

86 g (1 mol) of methacrylic acid was neutralized, while stirring, with 280 g of a 25% solution of potassium methylate in methanol. Thereafter, 0.6 g of N,N'-diphenyl-p-phenylenediamine, 2.8 g (0.009 mol) of 1-(2'-ethylhexyl)-4-dimethylaminopyridinium chloride and 198.5 g (1 mol) of 3-chloropropyltrimethoxysilane were added while continuously stirring, and the methanol was distilled off. The reaction mixture was maintained at 125° C. for 1.5 hours and, after cooling, it was separated from the precipitated potassium chloride by filtration. The potassium chloride was washed with methanol. The methanol was evaporated from the combined filtrates, and the residue was distilled under reduced pressure. 230 g of 3-methacryloxypropyltrimethoxysilane having a boiling of 82° C. (0.4 mbar) were obtained, which corresponds to a yield of 92.7% of theory, based on the amount of methacrylic acid used. The purity of the product was 98.5%. In the gas chromatogram only traces of 4-dimethylaminopyridine and 0.01% of 2-ethylhexyl methacrylate were detectable.

Workup

  1. distillationthe methanol was distilled off
  2. temperatureafter cooling
  3. customit was separated from the precipitated potassium chloride by filtration
  4. washThe potassium chloride was washed with methanol
  5. customThe methanol was evaporated from the combined filtrates
  6. distillationthe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-bb430cf79cf24858815ee395ea31bbd7
Source dataset
uspto-grants-1992_05
Patent number
US05117027

Reaction notes

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