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Method for co-producing and preparing methylthio acetate and diethyl thioglycolate

A technology of thiodiacetate diester and methylthioacetate is applied in directions such as thioether preparation, organic chemistry, etc., can solve problems such as expensive raw materials, high production cost, complicated process, etc., and achieves simple and feasible technological process, The effect of less production of three wastes and high product yield

Active Publication Date: 2018-11-09
SHANDONG ACADEMY OF PESTICIDE SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0021] As mentioned above, in the above several methods for synthesizing thiodiacetate diesters, a large amount of sulfur-containing and salt-containing wastewater will be produced, resulting in higher production costs, which is not conducive to industrial production
[0022] It can be seen that the synthetic routes of methylthioacetate and thiodiacetate diester in the prior art all have problems such as expensive raw materials, complex process, serious waste water pollution, and higher production costs, which are unfavorable for methylthioacetate and the synthesis of thiodiacetate diester

Method used

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  • Method for co-producing and preparing methylthio acetate and diethyl thioglycolate
  • Method for co-producing and preparing methylthio acetate and diethyl thioglycolate
  • Method for co-producing and preparing methylthio acetate and diethyl thioglycolate

Examples

Experimental program
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Embodiment 1

[0056] The coproduction method described in this embodiment prepares methyl thioacetate and thiodiacetate diester, comprises the steps:

[0057] (1) Preparation of compounds IV, V, and VI: Add 540 g (3.6 mol) of DL-methionine, 408 g (4.32 mol) of chloroacetic acid, and 3 L of water into a 5 L four-neck flask, stir evenly, slowly heat to 80 ° C, and carry out Reaction for 8 hours; after the reaction, the solvent water was recovered under reduced temperature and reduced pressure to obtain a total of 936 g of DL-homoserine lactone hydrochloride, methylthioacetic acid, and thiodiacetic acid mixture, and directly proceed to the next step without separation;

[0058] (2) Preparation of compound I, II, IV: get the mixture 312g (1.2mol DL-methionine) containing DL-homoserine lactone hydrochloride, methylthioacetic acid, thiodiacetic acid prepared in step (1). , 1.44mol of chloroacetic acid), 300ml of methanol, mix and stir evenly, control the temperature at 30-40°C, add 180.8g (1.52mo...

Embodiment 2

[0061] The coproduction method described in this embodiment prepares methyl thioacetate and thiodiacetate diester, comprises the steps:

[0062] (1) Preparation of compounds IV, V, VI: same as step (1) in Example 1;

[0063] (2) Preparation of compound I, II, IV: 156g (0.6mol DL-methionine, 0.72mol DL-methionine, 0.72mol Chloroacetic acid), 100ml of methanol, stirred evenly at room temperature and filtered, the filter cake was washed with 50ml of methanol; the filtrate was collected and 90.4g (0.76mol) of thionyl chloride was added dropwise to the above filtrate, and the temperature was controlled at 30-40°C. Continue to stir for 2 hours after the addition, cool down to -10°C, filter again, wash the filter cake with methanol (15mL×2 times); combine the two filter cakes and dry to obtain 76.2g of DL-homoserine lactone hydrochloride; the final filtrate Methanol was recovered under reduced pressure, and the remaining liquid was subjected to fractional distillation under reduced ...

Embodiment 3

[0066] The coproduction method described in this embodiment prepares methyl thioacetate and thiodiacetate diester, comprises the steps:

[0067] (1) Preparation of compounds IV, V, VI: same as step (1) in Example 1;

[0068] (2) Preparation of compound I, II, IV: 156g (0.6mol DL-methionine, 0.72mol DL-methionine, 0.72mol Chloroacetic acid), 150ml of ethanol, mix and stir evenly, control the temperature at 30-40°C, add 90.4g (0.76mol) of thionyl chloride dropwise, continue stirring for 2h after adding, cool down to -10°C, filter, and use ethanol (30mL×2 times) wash the filter cake, and dry to obtain 75.0g of DL-homoserine lactone hydrochloride; the filtrate reclaims ethanol under reduced pressure, and the remaining liquid is fractionated under reduced pressure to obtain 58.9g of ethyl methylthioacetate (content 98.5%), diethyl thiodiacetate 18.6g (content 98.3%).

[0069] Detect according to the method in the prior art, the gas chromatogram and the mass spectrogram of gained ...

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Abstract

The invention relates to the technical field of chemical synthesis and in particular relates to a method for co-producing and preparing methylthio acetate and diethyl thioglycolate by taking methionine as a raw material. The method for co-producing and preparing the methylthio acetate and the diethyl thioglycolate, provided by the invention, takes the methionine and haloacetic acid as raw materials to prepare three chemical products including homoserine lactone hydrohalide (IV), the methylthio acetate (I) and the diethyl thioglycolate (III) at the same time; all the products are easy to separate and purify.

Description

technical field [0001] The technical field of chemical synthesis of the present invention specifically relates to a method for co-producing methylthioacetate and thiodiacetate diester with methionine as a raw material. Background technique [0002] In the field of chemical synthesis, chemical intermediates have always played an important role, and methyl thioacetate and thiodiacetate diester are two important chemical intermediate products. [0003] Methylthioacetate can be used as a precursor for the synthesis of the new ophthalmic non-steroidal antipyretic analgesic anti-inflammatory drug nepafenac, and common methyl thioacetate and ethyl methylthioacetate can also As a food flavor for blending tomatoes, potatoes, horseradish, cabbage, meat, seafood, fruits, etc. Thiodiacetic acid diester is the key intermediate for the synthesis of 3,4-ethylenedioxythiophene (EDOT), which can be obtained by chemical polymerization or electrochemical polymerization The poly 3,4-ethylened...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/52C07C319/20
CPCC07C319/14C07C319/20C07D307/33C07C323/52
Inventor 解银萍柴洪伟董文凯韩金涛丛云波王秀丽张作山李旭坤
Owner SHANDONG ACADEMY OF PESTICIDE SCI
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