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Synthetic method of di(trimethyl silicon-based)acetylene

A technology of bistrimethylsilylacetylene and bistrimethylsilyl, which is applied in the field of synthesis of bistrimethylsilylacetylene, which can solve the problems of high cost, difficulty in recovering tetrahydrofuran, and high market price of bistrimethylsilylacetylene and other issues to achieve the effects of reducing production and emissions, reducing synthesis costs, and cheap prices

Inactive Publication Date: 2012-03-28
SHANGHAI RECORD PHARM CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this method has a high yield, the solvent tetrahydrofuran used is expensive, and it is very difficult to reclaim anhydrous tetrahydrofuran from water, so that tetrahydrofuran cannot be directly recovered and used mechanically, resulting in higher cost of the method, resulting in double three The market price of methylsilylacetylene is relatively expensive

Method used

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  • Synthetic method of di(trimethyl silicon-based)acetylene

Examples

Experimental program
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Effect test

Embodiment 1

[0018] In a 1000 ml three-necked flask, add 350 ml of toluene, add 70 g of disodium acetylene under the protection of nitrogen, cool to 0~10°C, and slowly add 310g of trimethylbromosilane dropwise under the control of 0~10°C, the dropwise addition is completed , raise the temperature to 50~60°C for 2 hours, after the reaction is completed, cool down to 20~30°C, slowly add 200 ml of water dropwise, after dropping, separate layers, extract the water layer twice with 50ml toluene, combine the toluene layers, and use anhydrous Drying over sodium sulfate, concentrating toluene at a vacuum of 40~60mmHg, and then rectifying with a 2*15cm rectification column at a vacuum of 10~20mmHg to obtain more than 99% of the target product bistrimethylsilylacetylene 158g, mol Yield 92.0%.

[0019] The molar mass ratio of acetylene dimetallic salt to trimethylhalosilane is 1:2.0~1:2.2,

Embodiment 2

[0021] In a 500 ml three-necked flask, add 175ml of toluene, add 35g of disodium acetylene under the protection of nitrogen, cool to 0-10°C, and slowly add 200g of iodotrimethylsilane dropwise under the control of 0-10°C. Raise the temperature to 50-60°C and react for 2 hours, after the reaction is complete, cool down to 20-30°C, slowly add 100 ml of water dropwise, after the drop is completed, separate layers, extract the water layer twice with 25ml toluene, combine the toluene layers, and wash with anhydrous sulfuric acid Sodium drying, concentrated toluene at a vacuum of 40~60mmHg, and then rectifying with a 2*15cm rectification column at a vacuum of 10~20mmHg to obtain more than 99% of the target product bistrimethylsilylacetylene 78g, molar yield The rate is 90.8%.

Embodiment 3

[0023] In a 5000 ml three-necked flask, add 1750 ml of toluene, add 350 g of disodium acetylene under the protection of nitrogen, cool to 0~10°C, and slowly add 1100g of trimethylchlorosilane dropwise under the control of 0~10°C, the dropwise addition is completed , heated up to 50~60°C and reacted for 2 hours. After the reaction was completed, lower the temperature to 20~30°C, slowly add 1000 ml of water dropwise. Sodium sulfate drying, under vacuum degree 40~60mmHg, concentrate toluene, then under vacuum degree 10~20mmHg, rectify with 2*15cm rectification column, obtain 99% target product of the present invention bistrimethylsilyl acetylene 802g, The molar yield is 93.4%.

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Abstract

The invention relates to a synthetic method of di(trimethyl silicon-based)acetylene. The method comprises the following steps: 1. taking diacetylenes metal salt and trimethyl halogenosilane as raw materials, wherein the mole mass ratio of diacetylenes metal salt to trimethyl halogenosilane is 1:2.0-1:2.2, suspending diacetylenes metal salt in toluene, adding trimethyl halogenosilane drop by drop, heating to the temperature of 50-60 DEG C after dripping is finished and reacting for 2 hours, wherein the diacetylenes metal salt is acetylene disodium and / or acetylene dibromo; 2, terminating the reaction by water, extracting, drying, reducing the pressure, concentrating, vacuum rectifying to obtain the di(trimethyl silicon-based)acetylene with the purity of more than 99%, wherein the yield is more than 90%. The synthetic method omits the preparation of a Grignard reagent, so that toluene which has advantages of cheap price and convenient recovery is capable of replacing tetrahydrofuran with expensive price, so that the synthesis cost is substantially reduced, because the toluene solvent used in the method of the invention has high recovery rate, so that the generation and discharge of toxic waste can be substantially minimized, and the toluene solvent is in favor of environmental protection.

Description

technical field [0001] The invention relates to a method for synthesizing bistrimethylsilylacetylene. Bistrimethylsilylacetylene is an important pharmaceutical intermediate and has wide market demand. Background technique [0002] The molecular weight of bis(trimethylsilyl)acetylene is 170.3995, and the molecular formula is C 8 h 18 Si 2 . The structural formula is: [0003] [0004] According to existing bibliographical reports, generally adopt the method of Grignard reagent, in tetrahydrofuran solvent, adopt bromoethane to make Grignard reagent, exchange with acetylene to make acetylene double format reagent, then drop trimethylchlorosilane, report The yield is 87%. Although this method has a high yield, the solvent tetrahydrofuran used is expensive, and it is very difficult to reclaim anhydrous tetrahydrofuran from water, so that tetrahydrofuran cannot be directly recovered and used mechanically, resulting in higher cost of the method, resulting in double three T...

Claims

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Application Information

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IPC IPC(8): C07F7/08
Inventor 张芳江胡伟杰
Owner SHANGHAI RECORD PHARM CO LTD
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