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Method for preparing 2-methyl-3-sulfydryl furan

A technology of mercaptofuran and methylfuran, which is applied in the field of compound synthesis, can solve the problems of difficult control of reaction conditions, high cost of raw materials, and complicated steps, and achieves the effects of easy control of reaction conditions, reduction of production costs, and broad application prospects.

Inactive Publication Date: 2017-05-31
WUTONG AROMA CHEM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The mercaptofuran synthesized from dimethylfuran and thioacetic acid has two methyl groups, and one methyl group must be removed at the end of the synthesis of the target product, which is cumbersome and costly, and the 3-position of the furan ring is directly synthesized from dimethylfuran and thioacetic acid. The 4 reaction opportunities are equally shared, and the synthetic product contains a large amount of isomers 2-methyl-4-mercaptofuran and 2-methyl-3-mercaptofuran. The reaction conditions are not easy to control, and the cost of raw materials is high, and the yield is low. only about 40%
How to solve the above problems has become the main bottleneck restricting the wide application of 2-methyl-3-mercaptofuran, and there are few reports on this aspect at home and abroad

Method used

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  • Method for preparing 2-methyl-3-sulfydryl furan
  • Method for preparing 2-methyl-3-sulfydryl furan
  • Method for preparing 2-methyl-3-sulfydryl furan

Examples

Experimental program
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Effect test

Embodiment 1

[0038] The preparation method of 2-methyl-3-mercaptofuran, the steps are as follows:

[0039] (1) Add 240g of methanol, 220g of sodium carbonate, and 205g of 2-methylfuran into a 2L glass bottle, and inject 160g of chlorine gas at 0-5°C to generate 2-methyl-(4,5)-dimethoxy -3(2H)-furan; most of the generated hydrogen chloride reacts with sodium carbonate to generate sodium chloride, and the remaining hydrogen chloride 6g, chlorine gas 8g, and carbon dioxide 88g are emitted;

[0040] Solid-liquid separation: the solid phase contains 227g of sodium chloride; the liquid is fractionally distilled to recover 167g of methanol, leaving 320g of raffinate containing 2-methyl-(4,5)-dimethoxy-3(2H)-furan ;

[0041] (2) 2-Methyl-(4,5)-dimethoxy-3(2H)-furan was added to 800g of water, washed with water, then 210g of thioacetic acid was added dropwise, stirred after dropping, and washed with 510g of dichloromethane Extract the 2-methyl-3-thioacetylfuran that generates; Phase separation; W...

Embodiment 2

[0047] The preparation method of 2-methyl-3-mercaptofuran, the steps are as follows:

[0048] (1) Add 23kg of methanol, 21kg of sodium carbonate, and 20kg of 2-methylfuran into a 200L reactor, and feed 15kg of chlorine gas at 0-5°C. Generate 2-methyl-(4,5)-dimethoxy-3(2H)-furan; most of the generated hydrogen chloride reacts with sodium carbonate to generate sodium chloride, remaining hydrogen chloride 0.6kg, chlorine 0.8kg, carbon dioxide 8.8 kg released.

[0049] Solid-liquid separation: the solid phase contains 22.7kg of sodium chloride. The liquid was fractionally distilled to recover 16.7kg of methanol, leaving 32kg of raffinate containing 2-methyl-(4,5)-dimethoxy-3(2H)-furan;

[0050] (2) 2-Methyl-(4,5)-dimethoxy-3(2H)-furan was added to 80kg of water, washed with water, then 20kg of thioacetic acid was added dropwise, stirred after dropping, and washed with 50kg of dichloromethane The resulting 2-methyl-3-thioacetylfuran was extracted. Phase separation; waste water ...

Embodiment 3

[0054] The preparation method of 2-methyl-3-mercaptofuran, the steps are as follows:

[0055] (1) Add 230kg of methanol, 212kg of sodium carbonate, and 200kg of 2-methylfuran into a 2000L reactor, and feed 150kg of chlorine gas at a low temperature of 0-5°C. 2-methyl-(4,5)-dimethoxy-3(2H)-furan is generated, most of the hydrogen chloride produced reacts with sodium carbonate to form sodium chloride, and the remaining 6kg of hydrogen chloride, 8kg of chlorine gas and 88kg of carbon dioxide are released.

[0056] Solid-liquid separation: the solid phase contains 227kg of sodium chloride. The liquid was fractionally distilled to recover 167kg of methanol, leaving 320kg of raffinate containing 2-methyl-(4,5)-dimethoxy-3(2H)-furan;

[0057] (2) 2-Methyl-(4,5)-dimethoxy-3(2H)-furan was added to 800kg of water, washed with water, then 200kg of thioacetic acid was added dropwise, stirred after dropping, and washed with 500kg of dichloromethane The resulting 2-methyl-3-thioacetylfura...

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Abstract

The invention relates to a method for preparing 2-methyl-3-sulfydryl furan. The method comprises the following steps: mixing methanol, sodium carbonate and 2-methyl furan, introducing chlorine gas under a low temperature condition, performing solid-liquid separation and taking liquid for distillation, so as to obtain a product 1; washing the product 1 with water, dropwise adding thioacetic acid, and performing extraction and phase separation after adding, so as to obtain a product 2; adding the product 2 into a dehydrating agent for dehydration, standing for phase separation, dropwise adding an obtained product into sodium hydroxide solution for reaction, stirring the mixture, standing for phase separation, taking an organic phase for distillation and purifying by rectification, so as to obtain 2-methyl-3-sulfydryl furan. Compared with the existing preparation method, the method for preparing 2-methyl-3-sulfydryl furan, disclosed by the invention, has the advantages that reaction conditions are controlled easily, side reactions are less, intermediate products are controlled easily, the yield of a target product is as higher as about 85%, and the method has wide application prospect.

Description

technical field [0001] The invention relates to a method for preparing 2-methyl-3-mercaptofuran, which belongs to the technical field of compound synthesis. Background technique [0002] 2-Methyl-3-mercaptofuran, also known as 2-methylfuranthiol, is a light pink to light orange liquid, CAS number: 28588-74-1, molecular formula: C 5 h 6 OS, molecular weight: 114.1655, relative density (1.100-1.150), boiling point (57-59.5)°C (44mmHg), refractive index 1.5090-1.5300, product quality: content ≥ 97%. The structural formula is: [0003] [0004] 2-Methyl-3-mercaptofuran is obtained by chemical synthesis using dimethylfuran and thioacetic acid as the main raw materials. The product is light yellow transparent liquid; it has roasted meat and coffee-like aroma. 2-Methyl-3-mercaptofuran is an important edible spice, which is currently mainly used in the field of food spices. It exists in meat products and is the main aroma and taste substance. It is currently used in beef, po...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/64
CPCC07D307/64
Inventor 李新卫洁陈祥臧传近张雷亮李晟王新军
Owner WUTONG AROMA CHEM CO LTD