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Method for synthesizing 2-ethoxy n-octyl thioether through three phase transfer catalysis without solvent

A technology of n-octyl sulfide and phase transfer catalysis, which is applied to the synthesis of asymmetric thioether, 2-hydroxyethyl n-octyl sulfide, and the synthesis of organic thioether, can solve the problem of low yield, Solve the problems of high risk of sodium metal and many by-products, and achieve the effect of simple reaction system, simple separation process and low production cost

Inactive Publication Date: 2010-04-28
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0031] The advantage of this method is that the source of raw materials is wide and easy to obtain, but this method has many by-products, the yield is not high, and the risk of using metal sodium is relatively high

Method used

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  • Method for synthesizing 2-ethoxy n-octyl thioether through three phase transfer catalysis without solvent
  • Method for synthesizing 2-ethoxy n-octyl thioether through three phase transfer catalysis without solvent
  • Method for synthesizing 2-ethoxy n-octyl thioether through three phase transfer catalysis without solvent

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Experimental program
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Effect test

Embodiment 1

[0054] Add sodium carbonate 4.2g (0.04mol) and deionized water in reaction system, stir and dissolve, pass into nitrogen protection, add n-octyl mercaptan 0.1mol and polystyrene (PS) graft PEG-200 catalyst 1.6g, then Add 0.1 mol of 2-chloroethanol dropwise, without organic solvents, under normal pressure, 40°C, react for 6 hours, filter out the catalyst after the reaction is over, let the filtrate stand for stratification, separate the oil phase and water phase, and perform gas chromatography on the oil phase Analysis showed that the yield of detoxol was 88.1%.

[0055] Under the above reaction conditions, the catalyst polystyrene (PS) grafted with PEG-200 was reused 6 times according to the above scheme, and the average yield of repellent alcohol was 87.7%.

Embodiment 2

[0057] Add salt of wormwood 8.3g (0.06mol) and deionized water in reaction system, stir and dissolve, pass into nitrogen protection, add n-octyl mercaptan 0.1mol and polyvinyl chloride (PVC) graft PEG-200 catalyst 1.8g, then Add 0.15 mol of 2-chloroethanol dropwise, without organic solvent, under normal pressure, 45°C, react for 7 hours, filter out the catalyst after the reaction, leave the filtrate to separate layers, separate the oil phase and water phase, and perform gas chromatography on the oil phase Analysis showed that the yield of detoxol was 84.8%.

[0058] Under the above reaction conditions, the catalyst polyvinyl chloride (PVC) grafted with PEG-200 was reused 5 times according to the above scheme, and the average yield of repellent alcohol was 83.9%.

Embodiment 3

[0060] The experimental procedure is the same as above, and the reaction conditions are as follows: n-octyl mercaptan 0.1mol, 2-chloroethanol 0.12mol, polystyrene (PS) grafted PEG-400 2.0g, sodium hydroxide 4.8g (0.12mol), no organic solvent, usually Press down, react at 70°C for 10 hours, filter out polystyrene (PS) grafted PEG-400, separate the oil phase, and perform gas chromatography analysis. The yield of detoxol is 96.8%.

[0061] Under the above reaction conditions, the catalyst polystyrene (PS) grafted with PEG-400 was reused 6 times according to the above scheme, and the average yield of repellent alcohol was 96.3%.

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Abstract

The invention discloses a new method for synthesizing 2-ethoxy n-octyl thioether through three phase transfer and catalysis without solvent, belonging to the technical field of fine chemicals synthetization. The method takes octyl mercaptan and 2-chlorohydrin as main raw materials, and uses organic macromolecule materials as the carrier, surface chemical modification is carried out, grafted polyethyleneglycol and quaternary ammonium salt with proper link and group structures are taken as the three phase transfer catalyst, the reaction is carried out for 6-12 hours at normal pressure and temperature of 40-90 DEG C without solvent to synthesize 2-ethoxy n-octyl thioether. Compared with the existing methods, the invention is characterized by available raw materials, low cost of production, mild reaction conditions, easy separation of the product after reaction, energy saving and consumption reducing. The three phase transfer catalyst has high activity, excellent selectivity, and good mechanical strength, and is easy to recycle from the reaction system. The invention has better industrialization application prospect.

Description

technical field [0001] The invention belongs to the technical field of synthesis of fine chemicals, and relates to a synthesis method of an organic sulfide, in particular to a synthesis method of an asymmetric sulfide. In more detail, the present invention relates to a synthesis method of 2-hydroxyethyl n-octyl sulfide (detoxol). Background technique [0002] Detoxol is a new type of slightly toxic (nearly non-toxic) and highly effective insect repellent, which has high repelling effects on mosquitoes, flies, reptiles, ants, bedbugs, etc. It can be used in offices, restaurants, and homes where people are concentrated , Garden use. In addition, it is also a commonly used non-ionic surfactant, which can be added to lubricating oil as an anti-wear additive, and is also an antagonist used in agriculture to alleviate severe deformities and stunting of crops caused by herbicides. [0003] At present, there is no literature report on the synthesis of detoxol in my country. The m...

Claims

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Application Information

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IPC IPC(8): C07C323/12C07C319/14
Inventor 章亚东唐海燕王振兴苏媛
Owner ZHENGZHOU UNIV
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