Method for synthesizing alkyl tetrahydrofurfuryl ether and sodium tetrahydrofurfuryl alcoholate

A technology of alkyl tetrahydrofurfuryl ether and tetrahydrofurfuryl alcohol, which is applied in the synthesis of asymmetric ether compounds, the synthesis of alkyl tetrahydrofurfuryl ether and the by-product of sodium tetrahydrofurfuryl alcohol, and can solve the problem of intractable lye and ethyl bromide. alkane leakage, environmental pollution and other problems, to achieve the effect of reducing pollution emissions, reducing production costs and eliminating risk factors

Inactive Publication Date: 2011-06-01
周铁生
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] Compared with the Williamson method, the above-mentioned existing Darzens condensation method is changed from a two-step reaction to a one-step reaction, which is more simple and easy, and the yield is higher, which can be higher than 70%, and the raw material of the reactant is easy to get and the cost is low. In actual use, it is found that it is prone to leakage of ethyl bromide, which will cause environmental pollution, and the lye generated by it is difficult to handle, so the best use effect cannot be achieved, and further improvement is urgently needed

Method used

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  • Method for synthesizing alkyl tetrahydrofurfuryl ether and sodium tetrahydrofurfuryl alcoholate
  • Method for synthesizing alkyl tetrahydrofurfuryl ether and sodium tetrahydrofurfuryl alcoholate
  • Method for synthesizing alkyl tetrahydrofurfuryl ether and sodium tetrahydrofurfuryl alcoholate

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Embodiment 1

[0040] In a 1L four-port reactor, add 2mol tetrahydrofurfuryl alcohol, 1.82mol ethyl bromide to react for 0.5 hours under stirring conditions, then add 1.82mol potassium hydroxide, the reaction temperature is 96°C, after reacting for 10 hours, add 1mol Metal sodium, reacted for 10.5 hours, and the reaction temperature was 25°C. Carry out distillation, wash with water, secondary distillation, obtain product 221g, conversion rate is 85%.

[0041] see Figure 1-3 Shown, with nuclear magnetic, infrared and mass spectrometry, prove that the product of the present embodiment is ethyl tetrahydrofurfuryl ether, product is carried out 1H-NMR is measured, CDCl is solvent, ETE nuclear magnetic spectrum and each hydrogen atom corresponding absorption peak is as shown in the figure shown. It should be noted that there are two absorption peaks for the hydrogen on the tetrahydrofuran ring and the α-position outside the ring.

Embodiment 2

[0043] In a 1L four-port reactor, add 2mol tetrahydrofurfuryl alcohol, 1.9mol ethyl bromide to react for 1.5 hours under stirring conditions, then add 1.9mol potassium hydroxide, the reaction temperature is 120°C, after reacting for 11 hours, add 0.2mol metal sodium, reacted for 11 hours, and the reaction temperature was 30°C. Carried out distillation, washing with water, and secondary distillation to obtain 224 g of ethyl tetrahydrofurfuryl ether product, with a conversion rate of 86%.

Embodiment 3

[0045] In a 1L four-port reactor, add 2mol tetrahydrofurfuryl alcohol, 1.98mol ethyl bromide to react for 3 hours under stirring, then add 1.98mol potassium hydroxide, the reaction temperature is 160°C, after 12 hours, add 0.45mol metal sodium, reacted for 12 hours, and the reaction temperature was 40°C. Distillation, washing with water, and secondary distillation were carried out to obtain 226 g of ethyl tetrahydrofurfuryl ether product, with a conversion rate of 86.8%.

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Abstract

The invention relates to a method for synthesizing alkyl tetrahydrofurfuryl ether and sodium tetrahydrofurfuryl alcoholate, which comprises the following steps of: A, mixing and reacting halogenated hydrocarbon and excess tetrahydrofurfuryl alcohol; B, adding alkali for continuous reaction; C, adding sodium metal; and D, obtaining an alkyl tetrahydrofurfuryl ether product. By the method for synthesizing the alkyl tetrahydrofurfuryl ether and the sodium tetrahydrofurfuryl alcoholate, the yield is high, the process is simple, the production is safe, the cost is low, the byproduct is simple in treatment, and the probability of environmental pollution in the production process is low, so the defects of the conventional tetrahydrofurfuryl ether synthesis method are overcome.

Description

technical field [0001] The invention relates to a method for synthesizing asymmetric ether compounds in the field of organic chemical industry, in particular to a method for synthesizing alkyl tetrahydrofurfuryl ether and by-product sodium tetrahydrofurfuryl alcohol. Background technique [0002] There are many synthetic methods of ethers, but for asymmetric ethers, there are mainly two synthetic methods: Williamson method and Darzens condensation method. [0003] Traditionally, the Williamson synthesis has been favored, namely: [0004] [0005] Wherein, X=Cl, Br, I. [0006] The first step reaction is a displacement reaction, and the metal sodium replaces the hydrogen in the alcohol to generate sodium alkoxide (nucleophile); the second step belongs to S N 2 Nucleophilic substitution reactions, the nucleophile "R 1 o - "Attack the carbon atom from the back of the leaving group, and at the same time, the C-X bond is gradually heterocleaved but not broken, forming a "t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/12
Inventor 周铁生
Owner 周铁生
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