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Synthetic method of 1-(2-chloroethoxy)propane

A technology of propoxychloroethane and a synthesis method, which is applied in chemical instruments and methods, preparation of organic compounds, organic chemistry and other directions, can solve the problems of high price, low product yield, complicated process and the like, and achieves low production cost. , the effect of high product yield and simple process

Active Publication Date: 2016-04-27
SHANDONG KAISHENG NEW MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Tong Guotong discloses a preparation method of the herbicide pretilachlor intermediate 2-propoxychloroethane in the patent CN200810061878.0. The method uses bis(trichloromethyl)carbonate as the chlorinating agent instead of chlorinated ethylene chloride. Chlorinating agents such as sulfone, phosphorus oxychloride, and hydrogen chloride, under organic solvent conditions, use organic amines as catalysts to synthesize 2-propoxychloroethane. Due to the addition of organic solvents, the product must be distilled and purified, resulting in product yields The production rate is low, the energy consumption is high, the product quality is unstable, and there are many process steps. At the same time, the price of bis(trichloromethyl)carbonate (triphosgene for short) is relatively high, which is not conducive to industrialization.
[0004] The traditional synthesis method of 2-propoxychloroethane has problems such as low product yield, unstable quality, serious environmental pollution, cumbersome process and prominent safety hazards. Therefore, the development of efficient, safe and environmentally friendly 2-propoxychloroethane Ethane Production Process Gets Wide Attention

Method used

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  • Synthetic method of 1-(2-chloroethoxy)propane
  • Synthetic method of 1-(2-chloroethoxy)propane

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Take 100g of ethylene glycol mono-n-propyl ether and 0.1g of dodecyltrimethylammonium chloride respectively and add them to the reaction vessel with a reflux condenser, add 125.65g of thionyl chloride to the constant pressure dropping funnel, and heat up to 35 ℃, start stirring, slowly add thionyl chloride dropwise to the reaction vessel, the reaction process releases sulfur dioxide and hydrogen chloride gas, control the rate of thionyl chloride addition to keep the temperature of the reaction solution at 50°C.

[0029] After the addition of thionyl chloride is completed, gradually raise the temperature to 90°C according to the reaction gas release rate until no gas is released, and continue to keep warm for 2 hours to obtain the crude product; after the crude product is cooled to 50°C, water is added to it for hydrolysis, and the water layer is separated and removed by standing , the organic layer was neutralized by sodium hydroxide solution, and the product was separat...

Embodiment 2

[0031] Take 100g of ethylene glycol mono-n-propyl ether and 0.3g of benzyltriethylammonium chloride into the reaction vessel with a reflux condenser, add 131.4g of thionyl chloride into the constant pressure dropping funnel, and heat up to 40°C. Start stirring, and slowly add thionyl chloride dropwise to the reaction vessel. During the reaction, sulfur dioxide and hydrogen chloride gas are released, and the rate of addition of thionyl chloride is controlled to keep the temperature of the reaction solution at 60°C.

[0032] After the thionyl chloride is added dropwise, gradually raise the temperature to 95°C according to the reaction gas release rate until no gas is released, and continue to keep warm for 3 hours to obtain the crude product; after the crude product is cooled to 40°C, water is added to it for hydrolysis, and the water layer is separated and removed by standing , the organic layer was neutralized by sodium hydroxide solution, and the product was separated to obtai...

Embodiment 3

[0034] Get 100g ethylene glycol mono-n-propyl ether, 0.5g methoxymethyltriphenylphosphine chloride respectively and add in the reaction vessel with reflux condenser, add 137.1g thionyl chloride into the constant pressure dropping funnel, heat up to At 45°C, start stirring, and slowly add thionyl chloride dropwise to the reaction vessel. During the reaction, sulfur dioxide and hydrogen chloride gas are released, and the rate of addition of thionyl chloride is controlled to keep the temperature of the reaction solution at 55°C.

[0035] After the dropwise addition of thionyl chloride, gradually raise the temperature to 100°C according to the reaction gas release rate until no gas is released, and continue to keep warm for 4 hours to obtain the crude product; after the crude product is cooled to 30°C, water is added to it for hydrolysis, and the water layer is separated and removed by standing , the organic layer was neutralized by sodium hydroxide solution, and the product was se...

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Abstract

The invention belongs to the technical field of organic synthesis and specifically relates to a synthetic method of 1-(2-chloroethoxy)propane. Under the action of a phase-transfer catalyst, 2-propoxyethanol and thionyl chloride are used as main raw materials, and reaction rate is controlled by dropwise adding thionyl chloride; after heating and thermal insulation, a crude product is obtained; and after hydrolysis, neutralization and standing for liquid separation, 1-(2-chloroethoxy)propane is obtained. In comparison with prior art, catalytic efficiency of the catalyst is high, the technological process is simple, safe and reliable, product yield is high, quality is stable, product content reaches 99.0% and above, yield is greater than 98.5%, and production cost is lower. The synthetic method of the invention is especially suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of 2-propoxyl ethyl chloride. Background technique [0002] 2-Propoxyethyl chloride is one of the important raw materials for the preparation of the herbicide pretilachlor. As a low-toxicity, broad-spectrum and high-efficiency professional selective herbicide, it is widely used in the field of rice planting and has a broad market. The external demand is large. [0003] At present, the preparation of 2-propoxychloroethane mainly uses ethylene glycol mono-n-propyl ether as the starting material, and uses different chlorinating agents to chlorinate its hydroxyl group. Yang Jianping etc. (the synthetic method of 2-n-propoxyl ethyl chloride, Zhejiang chemical industry, 1999, the 30th volume, the 4th phase) are chlorination agent with ethylene glycol monopropyl ether and thionyl chloride, adopt composite catalyst, The content of the final prod...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/22C07C43/12
CPCC07C41/22C07C43/12
Inventor 张泰铭王荣海张善民毕义霞李文娟贾远超
Owner SHANDONG KAISHENG NEW MATERIALS