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Clean production process of 2-thiopheneacetic acid

A technology of thiopheneacetic acid and clean production, applied in the direction of organic chemistry, etc., can solve the problems of unstable intermediate chloromethylthiophene, no application of 2-thiopheneacetic acid, and explosion hazard in reaction treatment, etc., and achieve high product yield and conversion High efficiency and simple operation

Active Publication Date: 2015-06-24
SHANDONG EFIRM BIOCHEMISTRY & ENVIRONMENTAL PROTECTION CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this process has two fatal shortcomings: first, the intermediate chloromethylthiophene is very unstable, and it is not easy to separate and purify it by large-scale equipment, and improper reaction treatment may cause explosion hazards; second, the reaction process requires the use of highly toxic substances Sodium cyanide; In this regard, people such as Ren Xiaoliang propose to react in organic solution, improve the stability of chloromethyl thiophene, adopt trimethyl silyl cyanide to replace sodium cyanide and reduce raw material toxicity (CN201410266507); But trimethyl silyl cyanide also It is a highly toxic substance, which is very harmful to the environment and human body
At present, this oxidation method has been successfully used in the oxidation research of many alcohol compounds, such as the preparation of carboxymethyl starch by oxidizing starch, but it has not been applied to the preparation of 2-thiopheneacetic acid.

Method used

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  • Clean production process of 2-thiopheneacetic acid

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] 10g of 2-thiophene ethanol, 0.4g of TEMPO, 200mL of acetonitrile, 100mL of phosphate buffer (0.6mol.L -1 ), stirred evenly, and the reactor was heated up to 35°C;

[0037] Then slowly add NaClO aqueous solution (16wt%) 80g dropwise to the reactor, after 2h dropwise, after continuing to react for 4h, add 2mol.L -1 Sodium sulfite solution, until NaClO is neutralized completely (starch potassium iodide test paper detects) in the reactor;

[0038] Add 2mol.L -1Adjust the solution to weak alkaline with NaOH, use ethyl acetate to extract the catalyst and unreacted raw materials, and then use 4mol.L -1 HCl adjusts the pH of the solution to 1, and extracts with ethyl acetate to obtain the crude product of 2-thiopheneacetic acid;

[0039] The crude product was recrystallized with petroleum ether to obtain pure 2-thiopheneacetic acid. The purity of the product detected by liquid phase was 99%, the conversion rate of 2-thiophene ethanol was 100%, the reaction selectivity was 95...

Embodiment 2

[0041] 10g of 2-thiophenethanol, 0.2g of 4-hydroxy TEMPO, 100mL of acetonitrile, 100mL of phosphate buffer (0.6mol.L -1 ), stirred evenly, and the reactor was cooled to 0°C;

[0042] Then NaClO was slowly added dropwise to the reactor 2 Aqueous solution (20wt%) 70.6g, 1.5h was added dropwise, after continuing to react for 3h, add 2mol.L -1 Sodium sulfite solution until NaClO in the reactor 2 Completely neutralized (detected by starch potassium iodide test paper);

[0043] Add 2mol.L -1 Adjust the solution to weak alkaline with NaOH, use ethyl acetate to extract the catalyst and unreacted raw materials, and then use 4mol.L -1 HCl adjusted the pH of the solution to 1.5, and extracted with ethyl acetate to obtain crude 2-thiopheneacetic acid;

[0044] The crude product was recrystallized from petroleum ether to obtain pure 2-thiopheneacetic acid, the conversion rate of 2-thiophenethanol was 92%, the reaction selectivity was 90%, and the yield was 73%.

Embodiment 3

[0046] 10g of 2-thiophene ethanol, 0.6g of 4-amino TEMPO, 300mL of acetonitrile, 100mL of phosphate buffer (0.6mol.L -1 ), stirred evenly, and the reactor was heated up to 50°C;

[0047] Then in the reactor, 138g of potassium hydrogen persulfate aqueous solution (50wt%) was slowly added dropwise, and the dropwise addition was completed in 2.5h. After continuing the reaction for 5h, 2mol.L -1 Sodium sulfite solution until potassium persulfate in the reactor is completely neutralized (detected by starch potassium iodide test paper);

[0048] Add 2mol.L -1 Adjust the solution to weak alkaline with NaOH, use ethyl acetate to extract the catalyst and unreacted raw materials, and then use 4mol.L -1 HCl adjusted the pH of the solution to 1.7, and extracted with ethyl acetate to obtain the crude product of 2-thiopheneacetic acid;

[0049] The crude product was recrystallized from petroleum ether to obtain pure 2-thiopheneacetic acid, the conversion rate of 2-thiophenethanol was 90%...

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Abstract

The invention relates to the chemical organic synthesis field and particularly discloses a method for preparing environment-friendly 2-thiopheneacetic acid with mild reaction condition. The 2-thiopheneacetic acid is prepared by taking 2, 2, 6, 6-tetramethyl piperidine nitrogen oxide (TEMPO) or the derivative as a catalyst and oxidizing 2-thiophene-ethanol through an oxidant such as sodium hypochlorite and sodium chlorite. The process is mild in reaction condition, high in reaction selectivity (95%), high in conversion rate (100%), high in yield (85%) and easy to be industrially operated.

Description

technical field [0001] The invention relates to the field of chemical synthesis, in particular to a clean production process of 2-thiopheneacetic acid. Background technique [0002] 2-thiopheneacetic acid is currently the most widely used thiophene series derivative, and is widely used in medicine, pesticides, dyes, polymer additives, etc. In the field of medicine, thiopheneacetic acid is an important intermediate for the synthesis of cefalotin sodium, cefotaxime, cefoxitin and other antibiotics. In recent years, many new cephalosporin antibiotics have been developed by using 2-thiopheneacetic acid abroad, such as ceftriazole, cefnetrol and furonicazone. As the main drug for the treatment of bacterial infectious diseases, antibiotics are the most widely used, fastest growing and most diverse class of drugs in the world, and have a relatively rigid demand. Therefore, the market prospect of 2-thiopheneacetic acid is broad. [0003] At present, there are two mature technolog...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/24
CPCC07D333/24
Inventor 易先君张建林刘文瑞姚刚马韵升
Owner SHANDONG EFIRM BIOCHEMISTRY & ENVIRONMENTAL PROTECTION CO LTD
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