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Solvent-free method for preparing 2-hydroxyethyl n-octyl sulfide through phase transfer catalysis

A technology of n-octyl sulfide and phase transfer catalysis, which is applied in the synthesis of 2-hydroxyethyl n-octyl sulfide, to the synthesis of asymmetric thioether, and the synthesis of organic thioether, can solve the problem of low yield, Sodium metal is highly dangerous and has many by-products, and achieves the effects of reducing production costs, good product selectivity, and mild reaction

Active Publication Date: 2012-10-03
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0030] 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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  • Solvent-free method for preparing 2-hydroxyethyl n-octyl sulfide through phase transfer catalysis
  • Solvent-free method for preparing 2-hydroxyethyl n-octyl sulfide through phase transfer catalysis
  • Solvent-free method for preparing 2-hydroxyethyl n-octyl sulfide through phase transfer catalysis

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Experimental program
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Effect test

Embodiment 1

[0043] Add 0.07 mol of sodium hydroxide and deionized water into the reaction system, stir to dissolve, and protect with nitrogen; then add 0.1 mol of mercaptoethanol and 0.0005 mol of quaternary ammonium catalyst cetyltrimethylammonium bromide, and dropwise add bromine Substitute n-octane 0.06mol, under normal pressure, stir at 30°C for 5 hours, cool the reaction mixture, let it stand and separate layers, the water phase is concentrated and crystallized, and sodium bromide crystals are refined, and the oil phase is 2-hydroxyethyl n-octane The crude octyl sulfide and 2-hydroxyethyl n-octyl sulfide are distilled under reduced pressure to obtain the final product. According to gas chromatography analysis, the yield of detoxol was 89.7%.

Embodiment 2

[0045] Add 0.08mol of sodium hydroxide and deionized water to the reaction system, stir to dissolve, and protect with nitrogen; then add 0.1mol of mercaptoethanol and 0.0015mol of quaternary ammonium catalyst cetyltrimethylammonium chloride, and add chlorine Substitute n-octane 0.06mol, under normal pressure, stir at 65°C for 9 hours, cool the reaction mixture, let it stand and separate layers, the water phase is concentrated and crystallized, and sodium bromide crystals are refined, and the oil phase is 2-hydroxyethyl n-octane The crude octyl sulfide and 2-hydroxyethyl n-octyl sulfide are distilled under reduced pressure to obtain the final product. According to gas chromatography analysis, the yield of detoxol was 87.4%.

Embodiment 3

[0047] Add 0.06 mol of sodium carbonate and deionized water to the reaction system, stir to dissolve, and protect with nitrogen; then add 0.1 mol of mercaptoethanol and 0.003 mol of tetrabutylammonium bromide, a quaternary ammonium salt catalyst, and add 0.12 mol of n-octane bromide dropwise. mol, under normal pressure, 60 ℃ constant temperature stirring for 4h, cooling the reaction mixture, static layering, the water phase is concentrated and crystallized, refined to sodium bromide crystals, the oil phase is the crude product of 2-hydroxyethyl n-octyl sulfide , 2-Hydroxyethyl n-octyl sulfide crude product was distilled under reduced pressure to obtain the final product. According to gas chromatography analysis, detoxol was obtained by distillation under reduced pressure, and the yield of detoxol was 91.2%.

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Abstract

The invention discloses a solvent-free method for preparing 2-hydroxyethyl n-octyl sulfide through phase transfer catalysis, and belongs to the technical field of synthesis of fine chemicals. In the method, halogen substituted octane and mercaptoethanol are taken as main raw materials; aqueous solution of alkali or basic salt is taken as a water phase; and under the condition of no organic solvent, the phase transfer catalysis technology is adopted, quaternary ammonium salt is taken as a phase transfer catalyst, and the main raw materials are reacted at a temperature between 30 and 70 DEG C under normal pressure for 4 to 10 hours to prepare the 2-hydroxyethyl n-octyl sulfide (2-(octylthio)ethanol). Compared with the conventional methods, the method has mild reaction conditions, simple andconvenient operation, and light environmental pollution; and after the reaction, products are simple and convenient to separate so as to save energy and reduce consumption. After the reaction of the water phase, sodium bromide is concentrated, crystallized and recovered to reach the industrial level so as to reduce production cost.

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 ma...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C323/12C07C319/14B01J31/02
Inventor 章亚东唐海燕王振兴苏媛
Owner ZHENGZHOU UNIV