Trialkoxysilanes connected with thioether bond on alpha-carbon and containing different functional groups based on sulfydryl-ene click reaction, and preparation

A technology of chloromethyltrialkoxysilane and mercaptomethyltrialkoxysilane, which is applied in the field of organosilicon synthesis, can solve the problems of unsatisfactory appearance, stability and purity, and reduce the use and reaction of toxic catalysts. The effect of mild conditions and high product purity

Active Publication Date: 2018-12-21
山东时代新材料科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, the appearance, stability and purity of the product are not ideal

Method used

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  • Trialkoxysilanes connected with thioether bond on alpha-carbon and containing different functional groups based on sulfydryl-ene click reaction, and preparation
  • Trialkoxysilanes connected with thioether bond on alpha-carbon and containing different functional groups based on sulfydryl-ene click reaction, and preparation
  • Trialkoxysilanes connected with thioether bond on alpha-carbon and containing different functional groups based on sulfydryl-ene click reaction, and preparation

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0077] A preparation method of α-mercaptomethyltriethoxysilane, comprising steps as follows:

[0078] (1) Add 19 mL of chloromethyltrichlorosilane to a 250 mL dry three-necked flask, dissolve 31 g of sodium ethoxide in 110 mL of ethanol solvent, and slowly drop it into the three-necked flask through a constant pressure dropping funnel under nitrogen protection , the rate of addition was 1 drop / second, and the addition was stopped when the pH of the system changed from acidic to neutral. After reacting at room temperature for 1 h, the organic solvent was removed by distillation under normal pressure and the insoluble matter was filtered off, and then distilled under reduced pressure to obtain chloromethyltriethoxysilane, which was reserved for later use.

[0079] (2) Add 63.105g of chloromethyltriethoxysilane, 25.120g of thiourea and 0.957g of potassium iodide into a 250mL dry three-necked round-bottomed flask, heat to 110°C, keep the reaction for 1.5h in a nitrogen atmosphere,...

Embodiment 2

[0082] Preparation of α-(Phenylethyl)mercaptomethyltriethoxysilane

[0083] The structural formula of α-(phenethyl)mercaptomethyltriethoxysilane is as formula (III):

[0084]

[0085] Including the following steps:

[0086] Add 2.630 g of α-mercaptomethyltriethoxysilane prepared in Example 1 and 1.302 g of styrene into a round-bottomed flask wrapped in aluminum foil, then add 8 mL of tetrahydrofuran, mix well, then add 0.079 g of benzoin dimethyl ether, Stir evenly, remove the aluminum foil, and irradiate for 30 minutes at room temperature under a UV lamp with a power of 20W and a wavelength of 365nm. After the reaction, the solvent was distilled off under reduced pressure, the vacuum degree was 5-6mmHg, precipitated in n-hexane three times, and dried in vacuum at 40°C to constant weight to obtain α-(phenylethyl)mercaptomethyltriethoxysilane , with a purity of 97% and a yield of 96%.

[0087] The infrared spectrum of the product α-(phenylethyl)mercaptomethyltriethoxysila...

Embodiment 3

[0089] Preparation of α-(methyl propionate)mercaptomethyltriethoxysilane

[0090] The structural formula of α-(methyl propionate) mercaptomethyltriethoxysilane is as formula (IV):

[0091]

[0092] Including the following steps:

[0093]Add 2.640g of α-mercaptomethyltriethoxysilane prepared in Example 1 and 1.290g of methyl acrylate into a round-bottomed flask wrapped in aluminum foil, then add 8mL of tetrahydrofuran, mix well and then add 0.079g of benzoin dimethyl ether , stir evenly, remove the aluminum foil, and irradiate for 30 minutes at room temperature under a UV lamp with a power of 20W and a wavelength of 365nm. After the reaction, the solvent was distilled off under reduced pressure, the vacuum degree was 5-6mmHg, precipitated in n-hexane three times, and dried in vacuum at 40°C to constant weight to obtain α-(methylpropionate)mercaptomethyltriethoxy silane with a purity of 97% and a yield of 96%.

[0094] The infrared spectrogram of the product α-(methyl prop...

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Abstract

The invention relates to a preparation method of trialkoxysilanes connected with a thioether bond on alpha-carbon and containing different functional groups. The method comprises the steps of reactingchloromethyltrichlorosilane and sodium alkoxide so as to prepare chloromethyltriethoxysilane, then reacting chloromethyltriethoxysilane and thiourea under the action of a catalyst so as to prepare alpha-sulfydrylmethyltriethoxysilane; through performing photo-initiation sulfydryl-ene click reaction, connecting alpha-sulfydrylmethyltriethoxysilane and a double-bond compound, and thus obtaining trialkoxysilanes connected with the thioether bond on the alpha-carbon and containing the different functional groups. According to the method, one of the raw materials is the industrial byproduct chloromethyltrichlorosilane, and the efficient utilization way is opened for chloromethyltrichlorosilane, so that environment protection and energy conversation are realized, the dosage of a toxic catalystis reduced, and the idea of green environment protection is met. According to the preparation method provided by the invention, the raw materials and reaction reagents are easy to get, the product iseasy to separate and purify, and the atom economy is met; the preparation process is simple, the reaction condition is mild, the cost is low, and the preparation method is suitable for large-scale industrial production and application.

Description

technical field [0001] The invention relates to a trialkoxysilane with a thioether bond connected to the α-carbon and containing different functional groups and a preparation method thereof, belonging to the technical field of organosilicon synthesis. Background technique [0002] At present, there are more than 100 kinds of silane coupling agents reported at home and abroad, one-third of which have been practically used, and their uses have penetrated into various fields. Silane coupling agent is the fourth major product after the three major products in the organic silicon industry: silicone oil, silicone rubber and silicone resin. Its position in the organic silicon industry is becoming more and more important. It is an indispensable supporting chemical additive in industry, composite material industry and related high-tech fields, and it is an important high-tech content and high value-added silicone product, which is vividly called "industrial monosodium glutamate". ...

Claims

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Application Information

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IPC IPC(8): C07F7/18C07F7/20
CPCC07F7/188C07F7/20
Inventor 贝逸翎高艳红朱庆增冯圣玉
Owner 山东时代新材料科技有限公司
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