Synthetic method of cyano-organosilicon compound

A technology of organosilicon compound and synthesis method, which is applied in the direction of organic chemistry, chemical instruments and methods, compounds of group 4/14 elements of the periodic table, etc., can solve the problems of increased reaction cost, cumbersome reaction process, and high synthesis temperature, and achieve The effect of reducing production energy consumption, easy Grignard reaction, and simple synthesis method

Active Publication Date: 2021-07-09
SHANDONG DONGYUE ORGANIC SILICON MATERIAL
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  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantages of the process are as follows: first, two steps are required to complete the synthesis of the target product when preparing the product, that is, hydrosilylation first, and then Grignard reagent reaction, the reaction process is relatively cumbersome; second, the use of dimethylhydrochlorosilane As a raw material for addition, the substance has a boiling point of 36°C, is volatile and highly flammable, has poor material safety, and requires high requirements for reaction equipment; thirdly, methylmagnesium bromide is used, and this substance can only be prepared and used by Grignard reagent. , and the preparation process requires highly active gaseous substances such as methyl bromide (boiling point 3.6°C), which requires high safety controllability and high requirements for reaction equipment
Fourth, the temperature of the hydrosilylation reaction is high, and the catalyst is expensive, which will increase the reaction cost
The amount of catalyst is relatively large, the reaction temperature is 70-120°C, the reaction time is 10-36h, the synthesis temperature is high, the synthesis cycle is long, and it needs to drop hydrochlorosilane at low temperature, and then react at high temperature. High requirements, high energy consumption and high cost for industrial production

Method used

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  • Synthetic method of cyano-organosilicon compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Under nitrogen protection, 1L tetrahydrofuran, 89.5g (1mol) 3-chloropropionitrile, 1.26g (0.01mol) anhydrous manganese chloride, 217g (2mol) trimethylchlorosilane, 0.179g dibromoethane were added to the reaction In the container, stir, heat to 50°C, add 0.252g magnesium chips for the first time, after the reaction is initiated, add 24.95g magnesium chips again, and react for 1.5h; Fractions were collected at an appropriate temperature to obtain a cyano-containing organosilicon compound monomer (ie, 2-cyanoethyltrimethylsilane).

[0033] The yield of the obtained cyano group-containing organosilicon compound monomer was 95.6%, and the purity was 99.8%.

Embodiment 2

[0035] Under nitrogen protection, 0.5L tetrahydrofuran, 103.5g (1mol) 4-chlorobutyronitrile, 2.52g (0.02mol) anhydrous manganese chloride, 387g (3mol) dimethyl dichlorosilane, 0.31g dibromoethane Add into the reactor, stir, heat to 65°C, add 0.514g magnesium chips for the first time, after the reaction is initiated, add 25.17g magnesium chips again, and react for 2 hours; , Collect fractions at a suitable temperature to obtain a cyano-containing organosilicon compound monomer (ie, 3-cyanopropyldimethylchlorosilane).

[0036] The yield of the obtained cyano group-containing organosilicon compound monomer was 96.1%, and the purity was 99.6%.

Embodiment 3

[0038] Under nitrogen protection, 0.25L toluene, 117.5g (1mol) 5-chlorovaleronitrile, 3.78g (0.03mol) anhydrous manganese chloride, 448.5g (3mol) methyltrichlorosilane, 0.47g dibromoethane Add into the reactor, stir, heat to 70°C, add 1.037g of magnesium chips for the first time, after the reaction is triggered, add 24.88g of magnesium chips again, and react for 4 hours; , Collect fractions at a suitable temperature to obtain a cyano-containing organosilicon compound monomer (ie, 4-hydrobutylmethyldichlorosilane).

[0039] The yield of the obtained cyano group-containing organosilicon compound monomer was 96.7%, and the purity was 99.5%.

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Abstract

The invention relates to the technical field of organosilicon compound synthesis, in particular to a synthesis method of a cyano-containing organosilicon compound. In the synthetic method of the present invention, chloronitrile and methyl-containing chlorosilane are used as raw materials, and dibromoethane is used as an initiator to generate a cyano-containing organosilicon compound through a one-step Grignard reagent method; The simplified structure is ClCH 2 (CH 2 ) n CN, wherein n is an integer of 0-6; the structural formula containing methyl chlorosilane is (CH 3 ) m SiCl 4‑m , where m is an integer of 1‑3. The synthesis method of the invention is simple and easy to implement, has fast reaction rate of raw materials, short synthesis period, easy separation of products, and high yield and purity of the target product.

Description

technical field [0001] The invention relates to the technical field of organosilicon compound synthesis, in particular to a synthesis method of a cyano-containing organosilicon compound. Background technique [0002] As a new type of green battery, lithium batteries have been widely used in consumer electronics products. Organosilicon compounds have the advantages of excellent thermal stability and low-temperature ion conductivity, high conductivity, non-toxicity, low flammability and high decomposition voltage, etc., and are gradually It has become a research hotspot of new electrolyte materials. Cyano-containing organosilicon compound monomers are important raw materials and intermediates for electrolytes and electrochemical devices. [0003] Patent US9680185 adopts hydrosilylation and Grignard method to synthesize cyano silicon compound, the raw material that this patent adopts has methyl bromide (or methylmagnesium bromide) and dimethyl hydrochlorosilane. The disadvant...

Claims

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Application Information

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Patent Type & AuthorityPatents(China)
IPC IPC(8): C07F7/12
Inventor伊港胡庆超王春晓刘海龙国建强李云杰孙江肖月玲
OwnerSHANDONG DONGYUE ORGANIC SILICON MATERIAL