Tris(trimethylsiloxy)silylpropyl methacrylate

Colorless transparent liquid

To a 500 mL three-necked flask equipped with a constant pressure funnel, magnetic stirrer, Dean-Stark tube and condenser, under nitrogen 124.18 g (0.5 mol) Methacryloxypropyltrimethoxysilane was added, 0.15 g of trifluoromethanesulfonic acid, 0.15 g of BHT was heated to 80 °C and 198.35 g (1.5 mol) of acetoxytrimethylene was added dropwise to the reaction flask through a constant pressure funnel. As the dropwise addition progressed, most of the low boiling by-products were continuously distilled off and collected from the Dean-Stark tube side tube. After completion of the addition, stirring was continued for 1 hour. The reaction product was transferred to a separatory funnel and washed with water (100 mL) six times to obtain a neutral colorless transparent liquid. A small amount of low boiling substance was removed by rotary evaporation under reduced pressure to obtain 198.08 g of methacryloxypropyltris(trimethylsiloxy)silane in a yield of 93.7percent. A 1000-ml four necked glass flask equipped with a reflux condenser, thermometer and stirrer was purged with nitrogen. The flask was charged with 406.0 g (2.5 mol) of hexamethyldisiloxane and 64.0 g (2.0 mol) of methanol, and cooled in an ice water bath to an internal temperature below 10°C. To the flask kept at an internal temperature of 5-10°C, 9.8 g (0.1 mol) of conc. sulfuric acid was added dropwise over 30 minutes, and stirring was continued at the temperature for 30 minutes. Subsequently, to the flask kept at an internal temperature of 5-10°C, 248.4 g (1.0 mol) of 3-methacryloxypropyltrimethoxysilane was added dropwise over 30 minutes, and stirring was continued at the temperature for one hour. At an internal temperature of 5-25°C, 72.0 g (4.0 mol) of water was added dropwise over one hour. After the completion of dropwise addition, stirring was continued at 15-25°C for 6.5 hours. The reaction solution was subjected to separatory operation to remove the aqueous layer. The organic layer was washed with water and separated again. The resulting organic layer of the reaction solution was analyzed by GC, finding that the area percent ratio of the main product to monomethoxy and monohydroxy compounds, 3-MAPSi(OSiMe3)3/[3-MAPSi(OMe)(OSiMe3)2 + 3-MAPSi(OH) (OSiMe3)2] was 22.5. The total content of monomethoxy and monohydroxy compounds was 0.044 mol, as determined from the area percents by GC. While the organic layer was kept at a temperature of 20-25°C, 24.5 g (0.25 mol) of conc. sulfuric acid was added dropwise over 15 minutes, and stirring was continued at the temperature for one hour. The organic layer after reaction with sulfuric acid was analyzed by GC, finding that the area percent ratio of the main product to monomethoxy and monohydroxy compounds, 3-MAPSi(OSiMe3)3/[3-MAPSi(OMe)(OSiMe3)2 + 3-MAPSi(OH)(OSiMe3)2] was 358.3. The sulfuric acid layer was removed from the reaction solution, after which the organic layer was washed with water, neutralized with aqueous sodium bicarbonate, and washed with water again. On distillation of the resulting organic layer, 393.5 g (0.93 mol) of 3-methacryloxypropyltris(trimethylsiloxy)silane with a purity of 99.6percent was collected as a fraction having a boiling point of 118.5-120.5°C/0.2 kPa. The yield was 93.1percent.EXAMPLE 13-methacryloxypropyltris(trimethylsiloxy)silaneIn a three-neck flask, 80.8 g (0.499 mol) of hexamethyldisiloxane, 39.9 g (0.67 mol) of acetic acid and 0.5 g of a 10percent solution of trifluoromethanesulfonic acid in acetic acid (0.0003 mol) are initially introduced and heated to 45° C. with stirring. Then, over the course of one hour (at 45° C.), 55.0 g (0.22 mol) of 3-methacryloxypropyl-trimethoxysilane (WACKER GENIOSIL.(R). GF 31) are added and after-stirred for 1 h at 45° C. The crude product is analyzed by means of gas chromatography (GC). Besides the readily volatile constituents of the reaction mixture, the following GC contents are found: product (44.3 area percent); monoorganoxy impurity CH

Molecular Weight:422.8
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:12
Exact Mass:422.17963045
Monoisotopic Mass:422.17963045
Topological Polar Surface Area:54
Heavy Atom Count:25
Complexity:420
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes