N,N'-Diphenyl-P-Phenylenediamine → 3-(Trimethoxysilyl)propyl methacrylate

Participants

Reaction Conditions

Reaction Steps

1.74 g (0.015 mol) of 4-dimethylaminopyridine were dissolved in 201.5 (1.015 mol) of 3-chloropropyltrimethoxysilane, and the solution was heated to 135° C. while stirring, and was maintained at this temperature for 15 minutes. After the solution had been cooled to 60° C., 124.2 g (1 mol) of potassium methacrylate and 0.6 g of N,N'-diphenyl-p-phenylenediamine were added. The mixture was then heated to 135° C. again and maintained at that temperature for 1 hour. Thereafter, it was cooled, and the potassium chloride which had precipitated was filtered off and washed with 80 g of methanol. The methanol was evaporated from the combined filtrates, and the residue was distilled under reduced pressure. 228.1 g of 3- methacryloxypropyltrimethoxysilane having a boiling point of 83° C. (0.4 mbar) were obtained. The yield was 92% of theory, based on the amount of potassium methacrylate used. The purity of the end product was 99.0%. In the gas chromatogram only traces of 4-dimethylaminopyridine were detectable.

Provenance & Evidence