PREPARATION METHOD OF FUNCTIONAL SILANES

Abstract

A preparation method of functional silanes comprises: substance A and substance B are added in a three-necked bottle and a certain amount of solvent is added; the resultant mixture is stirred for 0.5-24 h in the presence of catalyst under an atmosphere of argon, resulting in the crude product; after removing the remaining solvent and catalyst, the residual product is purified by chromatographic column to obtain functional silanes; the substance A is an alkene-containing silane and the substance B is an alcohol; functional silanes with various structures can be prepared, and their structures can be controlled by regulating the ratio of substance A and substance B, thereby providing ideas for the preparation of different silanes and the structural design of silane coupling agents.

Claims

1-10. (canceled)

11. A process of preparing a functional silane comprising reacting a substance A and a substance B at a temperature between 20° C. and 120° C. for 0.5 to 24 hours under water-free and oxygen-free condition; wherein the substance A having a structure shown as formula (I): ##STR00003## wherein R.sub.1, R.sub.2, and R.sub.3 are any of saturated alkyl groups from C.sub.1 to C.sub.18; R.sub.4 is a saturated alkyl group from C.sub.1 to C.sub.18 or a alkyl group containing heteroatoms; R.sub.5 is H, aromatic hydrocarbon, cycloalkane, or chain alkane. R.sub.1, R.sub.2, R.sub.3, R.sub.4, and R.sub.5 can either be identical to or different from each other; and the substance B is an alcohol or a polyhydroxy compound.

12. The process according to claim 11, characterized in that the reaction of the substance A and substance B is performed in an organic solvent that is one or more solvent(s) selected from a group consisting of tetrahydrofuran, dichloromethane, acetonitrile, dimethylformamide, toluene and chloroform.

13. (canceled)

14. The process according to claim 11, characterized in that the reaction of the substance A and substance B is performed at presence of a catalyst that is one or more compound(s) selected from a group consisting of inorganic bases, organic base and metal complex.

15. The process according to claim 14, characterized in that the inorganic base is sodium carbonate or cesium carbonate; the organic base is selected from a group consisting of 4-dimethylaminopyridine, phosphazene base, triphenylphosphine and potassium tert-butoxide; the metal complex is ytterbium triflate (Yb(OTf).sub.3) or metal N-heterocyclic carbenes (NHCs).

16. The process according to claim 14, characterized in that amount of the catalyst is 5 mol % to 20 mol % of total molar of the substance A and substance B.

17. The process according to claim 11, characterized in that the substance B is a monohydric alcohol R.sub.6OH or a polyhydroxy compound; wherein R.sub.6 is a linear or branched saturated alkyl group from C.sub.1 to C.sub.18.

18. The process according to claim 17, characterized in that the monohydric alcohol is selected from a group consisting of methanol, ethanol and propanol.

19. The process according to claim 11, characterized in that, in the reaction of the substance A and substance B, alkene to hydroxyl is 1:0.1-10.

Description

BRIEF DESCRIPTION OF THE FIGURES

[0032] FIG. 1 is the .sup.1H NMR spectrum of the target product in Embodiment 1.

[0033] FIG. 2 is the .sup.1H NMR spectrum of the target product in Embodiment 2.

[0034] FIG. 3 is the .sup.1H NMR spectrum of the target product in Embodiment 3.

[0035] FIG. 4 is the .sup.1H NMR spectrum of the target product in Embodiment 4.

DETAILED EMBODIMENTS

[0036] The invention is further described in combination with specific embodiments as follows, but the protection scope of the present invention is not limited to this.

[0037] Meanwhile, the experimental methods described in the following embodiments are all conventional methods unless otherwise specified; the said reagents and materials are commercially available unless otherwise specified.

Embodiment 1

[0038] Under an atmosphere of argon, 0.234 g of 3-(acryloyloxy)propyltrimethoxysilane and 0.046 g of ethanol, 5 ml of dichloromethane, and 0.03675 g of phosphonitrile base t-BuP.sub.2 were successively added into a three-necked flask, which were cycled through three freeze-thaw pumps. The mixture was stirred for 3 h at room temperature under the water-free and oxygen-free condition. The catalyst was removed through an acidic alumina column and the solvent was removed by rotary evaporation. The crude product was purified to obtain the target new functional silane. The reaction conversion rate was 92%.

Embodiment 2

[0039] Under an atmosphere of argon, 0.234 g of 3-(acryloyloxy)propyltrimethoxysilane, 0.092 g of ethanol, 5 ml of dichloromethane, and 0.03675 g of phosphonitrile base t-BuP.sub.2 were successively added into a three-necked flask, which were cycled through three freeze-thaw pumps. The mixture was stirred for 3 h at room temperature under the water-free and oxygen-free condition. The catalyst was removed through an acidic alumina column and the solvent was removed by rotary evaporation. The crude product was purified to obtain the target new functional silane. The reaction conversion rate was 96%.

Embodiment 3

[0040] Under an atmosphere of argon, 0.234 g of 3-(acryloyloxy)propyltrimethoxysilane, 0.138 g of ethanol, 5 ml of dichloromethane, and 0.03675 g of phosphonitrile base t-BuP.sub.2 were successively added into a three-necked flask, which were cycled through three freeze-thaw pumps. The mixture was stirred for 3 h at room temperature under the water-free and oxygen-free condition. The catalyst was removed through an acidic alumina column and the solvent was removed by rotary evaporation. The crude product was purified to obtain the target new functional silane. The reaction conversion rate was 95%.

Embodiment 4

[0041] Under an atmosphere of argon, 0.234 g of 3-(acryloyloxy)propyltrimethoxysilane, 0.184 g of ethanol, 5 ml of dichloromethane, and 0.03675 g of phosphonitrile base t-BuP.sub.2 were successively added into a three-necked flask, which were cycled through three freeze-thaw pumps. The mixture was stirred for 3 h at room temperature under the water-free and oxygen-free condition. The catalyst was removed through an acidic alumina column and the solvent was removed by rotary evaporation. The crude product was purified to obtain the target new functional silane. The reaction conversion rate was 97%.

Embodiment 5

[0042] Under an atmosphere of argon, 0.234 g of 3-(acryloyloxy)propyltrimethoxysilane and 0.032 g of ethanol, 5 ml of dichloromethane, and 0.0122 g of 4-dimethylaminopyridine were successively added into a three-necked flask, which were cycled through three freeze-thaw pumps. The mixture was stirred for 3 h at room temperature under the water-free and oxygen-free condition. The catalyst was removed through an acidic alumina column and the solvent was removed by rotary evaporation. The crude product was purified to obtain the target new functional silane.

Embodiment 6

[0043] Under an atmosphere of argon, 0.248 g of 3-(methacryloyloxy)propyltrimethoxysilane, 0.032 g of ethanol, 5 ml of dichloromethane, 0.0122 g of potassium tert-butoxide were successively added into a three-necked flask, which were cycled through three freeze-thaw pumps. The mixture was stirred for 3 h at room temperature under the water-free and oxygen-free condition. The catalyst was removed through an acidic alumina column and the solvent was removed by rotary evaporation. The crude product was purified to obtain the target new functional silane.

Comparative Example 1

[0044] 0.234 g of 3-(acryloyloxy)propyltrimethoxysilane, 0.046 g of ethanol, 5 ml of dichloromethane, 0.03675 g or 0.0122 g of 4-dimethylaminopyridine were successively added to a three-necked flask and stirred at room temperature in an air environment for 3 h. Since the reaction was carried out in air, the product is the hydrolysis and crosslinking product from 3-(acryloyloxy)propyltrimethoxysilane due to the moisture in the air. Therefore, the target functional silane can not be achieved.