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Trimethylsilylacetylene synthesis process

A technology of trimethylsilylacetylene and trimethylsilylethylene, which is applied in the field of trimethylsilylacetylene synthesis process route, can solve the problems of high risk of operation, explosion, and difficulty in purification, and achieve the effect of safe reaction system

Pending Publication Date: 2021-01-01
DALIAN RES & DESIGN INST OF CHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The existing synthetic process route is to first make 1-chloro-n-butane into Grignard reagent, pass through gas acetylene to replace, form acetylene Grignard reagent, then react with trimethylchlorosilane, and then obtain trimethylsilylacetylene by distillation ; This route uses gas acetylene, there is a danger of explosion in the reaction process, and the operation is very dangerous
As described in the 2014 Chinese patent "A Production Process of Trimethylsilylacetylene" (CN103896976A), the intermediate product 1,2-dibromoethyltrimethylsilane reacts under alkaline conditions; this reaction produces a large amount of As a by-product, it is difficult to purify, and the pure product trimethylsilylacetylene cannot be obtained

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] [embodiment 1] the preparation of trimethylsilaneethylene

[0024] Put 1.1mol of magnesium and 800mlTHF into a 2L four-necked reaction flask, slowly add 1mol of vinyl bromide and 200mLTHF mixture at room temperature, gradually raise the temperature to trigger the reaction, until reflux; after dripping, reflux for 1h; keep reflux and add trimethyl chloride dropwise The mixture of 1 mol of silane and 100 mL of tetrahydrofuran was monitored by GC until the reaction was complete; the reaction liquid was rectified to collect fractions at 60-65°C to obtain 95 g (yield 95%) of trimethylsilaneethylene.

Embodiment 2

[0025] [Example 2] Preparation of 1-bromotrimethylsilylethylene

[0026] Put 0.9 mol of trimethylsilylethylene, 2.25 mol of triethylamine and 400 ml of dichloromethane into a 1L four-necked reaction flask, control the temperature at -10~-5°C, add 1.06 mol of liquid bromine dropwise, and complete the dropwise addition in 1 hour. Reaction 2 -4h, reflux for 1-3h, and GC detects that the reaction of trimethylsilylethylene is complete. After cooling and filtering, the filtrate was rectified under reduced pressure to collect fractions at 72-75°C to obtain 165 g (92.2%) of 1-bromotrimethylsilylethylene.

Embodiment 3

[0027] [Example 3] Preparation of 1-bromotrimethylsilylethylene

[0028] Put 0.9mol of trimethylsilylethylene, 2.25mol of triethylamine and 400ml of dichloromethane into a 1L four-necked reaction flask, control the temperature at 5-10°C, add 1.06mol of liquid bromine dropwise, the dropwise addition is completed in 1 hour, and react for 2-4 hours , Refluxed for 1-3h, GC detected that the reaction of trimethylsilylethylene was complete, but GC showed that the product was impure, with 73% by-products.

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PUM

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Abstract

The invention discloses a process route for synthesizing trimethylsilylacetylene, which comprises the following steps of: generating trimethylchlorosilylethylene by taking ethylene bromide and trimethylchlorosilane as initial raw materials through a Grignard method, and forming 1-bromo trimethylchlorosilylethylene under the action of alkali through a bromination reagent; and removing monomolecularhydrogen bromide under the action of strong alkali to generate trimethylsilylacetylene. Compared with the traditional process, the process route has the advantages that the use of gas acetylene is avoided, the risk is reduced, the safety is improved, the used raw materials are easily available, the operation is easy, the safety and the environmental protection are realized, and the industrial production can be realized.

Description

technical field [0001] The invention relates to a synthesis process route of trimethylsilylacetylene, which belongs to the category of chemical pharmacy. Background technique [0002] Trimethylsilylacetylene is an important spice and pharmaceutical intermediate, one of the important silicon-based chemical raw materials, and an important alkynylation reagent, which is essential in the preparation of various mono-alkyne and polyalkyne In addition, there are many applications in heterocyclic chemistry, carbon-carbon coupling, drug synthesis, catalytic chemistry and materials industry. [0003] It is also used as a silicon-based protecting group for the synthesis of pyrazoles via 1,3-bipolar cycloaddition of acetylene diazoxide, and as a substrate for nickel-catalyzed and benzonitrile coupling reactions. [0004] The existing synthetic process route is to first make 1-chloro-n-butane into Grignard reagent, pass through gas acetylene to replace, form acetylene Grignard reagent, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/08
CPCC07F7/0805C07F7/0827C07F7/083
Inventor 王可为刘威
Owner DALIAN RES & DESIGN INST OF CHEM IND