CN115491700A - Electrochemical synthesis method of spice 2-propionyl thiazole - Google Patents
Electrochemical synthesis method of spice 2-propionyl thiazole Download PDFInfo
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- CN115491700A CN115491700A CN202211324730.8A CN202211324730A CN115491700A CN 115491700 A CN115491700 A CN 115491700A CN 202211324730 A CN202211324730 A CN 202211324730A CN 115491700 A CN115491700 A CN 115491700A
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- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
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- C25B3/01—Products
- C25B3/09—Nitrogen containing compounds
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- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
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Abstract
The invention discloses an electrochemical synthesis method of spice 2-propionyl thiazole, which comprises the following steps: adding a saturated ammonium bisulfate solution, sodium tungstate, 2-propylthiazole, a catalyst and dichloromethane into an anode chamber of an electrolytic cell, wherein the molar ratio of the sodium tungstate to the 2-propylthiazole to the catalyst to an organic solvent is 0.1‑1:1‑20:0.1‑1:400‑600; the volume ratio of the saturated ammonium bisulfate solution to the dichloromethane is 1; adding a potassium dihydrogen phosphate saturated solution into the cathode chamber; the anode chamber and the cathode chamber of the electrolytic cell are separated by a cation exchange membrane; and electrifying for electrolysis under the stirring state, and preparing the 2-propionyl thiazole in the anode chamber.
Description
Technical Field
The invention belongs to the technical field of fine chemical engineering and organic electrochemical synthesis, and particularly relates to an electrochemical synthesis method of 2-propionyl thiazole serving as a spice.
Background
The statements herein merely provide background information related to the present disclosure and may not necessarily constitute prior art.
The 2-propionyl thiazole is a widely applied food additive and a medicine intermediate. The prior preparation methods mainly comprise two methods, one method is to prepare a Grignard reagent by taking 2-bromothiazole as a raw material and then react the Grignard reagent with propionyl chloride to synthesize the Grignard reagent. The Grignard reagent prepared by the method has poor stability and extremely low total reaction yield. The second method is also to use 2-bromothiazole as a raw material to react with butyl lithium and propionyl chloride, and although the method has considerable yield, the reaction needs to be carried out at-78 ℃, and the reaction conditions are harsh, so that the method is not beneficial to industrial production.
Disclosure of Invention
Aiming at the defects in the prior art, the invention aims to provide an electrochemical synthesis method of 2-propionyl thiazole serving as a spice.
In order to achieve the purpose, the invention is realized by the following technical scheme:
the electrochemical synthesis method of the 2-propionyl thiazole as the spice comprises the following steps:
adding a saturated ammonium bisulfate solution, sodium tungstate, 2-propylthiazole, a catalyst and dichloromethane into an anode chamber of an electrolytic cell, wherein the molar ratio of the sodium tungstate to the 2-propylthiazole to the catalyst to the organic solvent dichloromethane is 0.1-1:1-20; the volume ratio of the saturated ammonium bisulfate solution to the dichloromethane is 1;
adding a potassium dihydrogen phosphate saturated solution into the cathode chamber;
the anode chamber and the cathode chamber of the electrolytic cell are separated by a cation exchange membrane;
and electrifying for electrolysis under the stirring state, and preparing the 2-propionyl thiazole in the anode chamber.
Cation exchange membrane for removing H in anode chamber + And timely delivered to the cathode chamber.
The stirring is to uniformly mix the water-soluble raw material and the oil-soluble raw material, so as to facilitate the reaction.
In some embodiments, the ammonium bisulfate solution is a saturated ammonium bisulfate solution. Saturated ammonium bisulfate can increase conductivity and reduce energy consumption.
In some embodiments, the catalyst is selected from copper acetate, manganese acetate, silver nitrate, copper chloride, or manganese sulfate. These catalysts catalyze the step of synthesizing sodium peroxotungstate by oxidizing ammonium persulfate.
Preferably, the catalyst is copper acetate, manganese acetate or silver nitrate.
In some embodiments, the cation exchange membrane is Nafion-324 or NaFion-424
In some embodiments, the anode of the electrolysis chamber is a DSA electrode, a graphite electrode, or a platinum electrode.
The DSA electrode is made by using a metal material such as stainless steel as a substrate of the electrode and coating a noble metal oxide such as ruthenium and palladium having catalytic activity on the metal substrate. The noble metal oxide coating on the surface layer of the electrode has an electrocatalytic effect and can influence the electrochemical reaction speed.
In some embodiments, the cathode is a graphite electrode or a lead alloy electrode.
In some embodiments, the molar ratio of sodium tungstate, 2-propylthiazole, catalyst, and organic solvent is 0.1-0.5; the volume ratio of the saturated ammonium bisulfate solution to the dichloromethane is 1.8-1.5.
Preferably, the organic solvent is dichloromethane, chloroform, carbon tetrachloride or chlorobenzene.
In some embodiments, the current density of the electrolysis is 80-250mA/m 2 。
Preferably, the current density of electrolysis is 80-150mA/m 2 。
The beneficial effects achieved by one or more of the embodiments of the invention described above are as follows:
the method for synthesizing the 2-propionyl thiazole by using the electrochemical method has the characteristics of mild conditions, easy control of reaction, environmental friendliness and the like.
Detailed Description
It is to be understood that the following detailed description is exemplary and is intended to provide further explanation of the invention as claimed. Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs.
The electrolytic cell can be an H-shaped electrolytic cell, and comprises an anode chamber and a cathode chamber, wherein the upper parts of the anode chamber and the cathode chamber are connected through a direct current power supply. The anode chamber and the cathode chamber are communicated through a cation exchange membrane.
The electrochemical equation of the method for synthesizing 2-propionyl thiazole of the invention is as follows:
and (3) anode reaction:
2NH 4 HSO 4 -e→(NH 4 ) 2 S 2 O 8 +2H +
(NH 4 ) 2 S 2 O 8 +Na 2 WO 4 +H 2 O→Na 2 WO 5 +2NH 4 HSO 4
and (3) cathode reaction:
2H + +e→H 2 。
the present invention will be further described with reference to the following examples.
Example 1
An H-shaped electrolytic cell is used as a reactor, an anode is a DSA mesh electrode, a cathode is a graphite electrode, and an anode chamber and a cathode chamber are separated by a NaFiona-324 cation exchange membrane.
To the anode chamber were added 40mL of a saturated ammonium bisulfate solution, 0.3mmol of sodium tungstate, 10mmol of 2-propylthiazole, 0.5mmol of copper acetate, and 40g of methylene chloride in this order. 80ml of saturated potassium dihydrogen phosphate solution was sequentially added to the cathode chamber.
Stirring at constant temperature of 25 deg.C, electrolyzing while maintaining current density of 100mA/m 2 When the amount of energization reaches 2F/mol, energization is stopped. Separating out organic phase, purifying to obtain 2-propionylIsothiazole, yield 86%.
Example 2
An H-shaped electrolytic cell is used as a reactor, the anode is a graphite electrode, the cathode is a lead electrode, and the anode chamber and the cathode chamber are separated by a NaFiona-424 cation exchange membrane.
To the anode chamber were added 40mL of a saturated ammonium bisulfate solution, 0.3mmol of ammonium tungstate, 10mmol of 2-propylthiazole, 0.1mmol of copper acetate, and 40g of methylene chloride in this order. 80ml of saturated potassium dihydrogen phosphate solution was sequentially added to the cathode chamber.
Stirring at constant temperature of 25 deg.C, electrolyzing while maintaining current density of 100mA/m 2 When the amount of energization reaches 2F/mol, energization is stopped. The organic phase was separated and purified to give 2-propionyl thiazole in 76% yield.
Example 3
An H-shaped electrolytic cell is used as a reactor, an anode is a DSA mesh electrode, a cathode is a graphite electrode, and an anode chamber and a cathode chamber are separated by a NaFiona-324 cation exchange membrane.
To the anode chamber were added 40mL of a saturated ammonium bisulfate solution, 0.3mmol of sodium tungstate, 10mmol of 2-propylthiazole, 0.5mmol of silver nitrate, and 40g of dichloromethane in this order. 80ml of saturated potassium dihydrogen phosphate solution was sequentially added to the cathode chamber.
Stirring at a constant temperature of 25 deg.C, electrolyzing while maintaining the current density at 100mA/m 2 When the amount of energization reaches 2F/mol, energization is stopped. The organic phase was separated and purified to give 2-propionyl thiazole in 89% yield.
Example 4
An H-type electrolytic cell is used as a reactor, an anode is a platinum electrode, a cathode is a lead electrode, and an anode chamber and a cathode chamber are separated by a NaFiona-324 cation exchange membrane.
To the anode chamber were added 40mL of a saturated ammonium bisulfate solution, 0.3mmol of sodium tungstate, 10mmol of 2-propylthiazole, 0.5mmol of copper acetate, and 40g of dichloromethane in this order. 80ml of saturated potassium dihydrogen phosphate solution was sequentially added to the cathode chamber.
Stirring at constant temperature of 25 deg.C, electrolyzing while maintaining current density of 100mA/m 2 When the amount of energization reaches 2F/mol, energization is stopped. Separating out an organic phase, purifying to obtain the 2-propionyl thiazole,the yield thereof was found to be 85%.
Example 5
An H-shaped electrolytic cell is used as a reactor, an anode is a DSA mesh electrode, a cathode is a graphite electrode, and an anode chamber and a cathode chamber are separated by a NaFiona-324 cation exchange membrane.
40mL of a saturated ammonium bisulfate solution, 0.3mmol of sodium tungstate, 10mmol of 2-propylthiazole, 0.5mmol of manganese acetate, and 40g of methylene chloride were sequentially added to the anode chamber. 80ml of a saturated solution of potassium dihydrogen phosphate was sequentially added to the cathode chamber.
Stirring at a constant temperature of 25 deg.C, electrolyzing while maintaining the current density at 100mA/m 2 When the amount of energization reaches 2F/mol, energization is stopped. The organic phase was separated and purified to give 2-propionyl thiazole in 82% yield.
Example 6
An H-shaped electrolytic tank is used as a reactor, the anode is a graphite electrode, the cathode is a graphite electrode, and the anode chamber and the cathode chamber are separated by a NaFiona-324 cation exchange membrane.
40mL of a saturated ammonium bisulfate solution, 0.3mmol of ammonium tungstate, 10mmol of 2-propylthiazole, 0.5mmol of copper acetate, and 40g of dichloromethane were sequentially added to the anode chamber. 80ml of saturated potassium dihydrogen phosphate solution was sequentially added to the cathode chamber.
Stirring at constant temperature of 25 deg.C, electrolyzing while maintaining current density of 100mA/m 2 When the amount of energization reaches 3F/mol, energization is stopped. The organic phase was separated and purified to give 2-propionyl thiazole in 78% yield.
Example 7
An H-shaped electrolytic cell is used as a reactor, an anode is a DSA mesh electrode, a cathode is a graphite electrode, and an anode chamber and a cathode chamber are separated by a NaFiona-424 cation exchange membrane.
40mL of a saturated ammonium bisulfate solution, 0.3mmol of ammonium tungstate, 10mmol of 2-propylthiazole, 0.5mmol of manganese sulfate and 40g of dichloromethane were sequentially added to the anode chamber. 80ml of saturated potassium dihydrogen phosphate solution was sequentially added to the cathode chamber.
Stirring at constant temperature of 25 deg.C, electrolyzing while maintaining current density of 150mA/m 2 When the amount of energization reaches 2F/mol, energization is stopped. Separating out an organic phase, purifying to obtain the 2-propionyl thiazole,the yield thereof was found to be 77%.
Example 8
An H-shaped electrolytic cell is used as a reactor, an anode is a platinum electrode, a cathode is a lead electrode, and an anode chamber and a cathode chamber are separated by a NaFiona-424 cation exchange membrane.
To the anode chamber were added 40mL of a saturated ammonium bisulfate solution, 0.3mmol of ammonium tungstate, 10mmol of 2-propylthiazole, 0.5mmol of copper chloride, and 40g of methylene chloride in this order. 80ml of a saturated solution of potassium dihydrogen phosphate was sequentially added to the cathode chamber.
Stirring at constant temperature of 25 deg.C, electrolyzing while maintaining current density of 200mA/m 2 When the amount of energization reaches 2F/mol, energization is stopped. The organic phase was separated and purified to give 2-propionyl thiazole in 68% yield.
Example 9
An H-shaped electrolytic cell is used as a reactor, an anode is a DSA mesh electrode, a cathode is a graphite electrode, and an anode chamber and a cathode chamber are separated by a NaFiona-324 cation exchange membrane.
To the anode chamber were added 40mL of a saturated ammonium bisulfate solution, 0.3mmol of sodium tungstate, 10mmol of 2-propylthiazole, 0.1mmol of copper acetate, and 40g of methylene chloride in this order. 80ml of saturated potassium dihydrogen phosphate solution was sequentially added to the cathode chamber.
Stirring at constant temperature of 25 deg.C, electrolyzing while maintaining current density of 100mA/m 2 When the amount of energization reaches 2F/mol, energization is stopped. The organic phase was separated and purified to give 2-propionyl thiazole in 65% yield.
Example 10
An H-shaped electrolytic tank is used as a reactor, the anode is a DSA mesh electrode, the cathode is a graphite electrode, and the anode chamber and the cathode chamber are separated by a NaFiona-324 cation exchange membrane.
To the anode chamber were added 40mL of a saturated ammonium bisulfate solution, 0.1mmol of sodium tungstate, 10mmol of 2-propylthiazole, 0.1mmol of copper acetate, and 40g of methylene chloride in this order. 80ml of a saturated solution of potassium dihydrogen phosphate was sequentially added to the cathode chamber.
Stirring at constant temperature of 25 deg.C, electrolyzing while maintaining current density of 100mA/m 2 When the amount of energization reaches 2F/mol, energization is stopped. Separating out organic phase, purifying to obtain 2-propionyl thiazole with yield46％。
Example 11
An H-shaped electrolytic cell is used as a reactor, an anode is a DSA mesh electrode, a cathode is a graphite electrode, and an anode chamber and a cathode chamber are separated by a NaFiona-324 cation exchange membrane.
To the anode chamber were added 40mL of a saturated ammonium bisulfate solution, 0.1mmol of sodium tungstate, 10mmol of 2-propylthiazole, 0.1mmol of silver nitrate, and 40g of dichloromethane in this order. 80ml of saturated potassium dihydrogen phosphate solution was sequentially added to the cathode chamber.
Stirring at constant temperature of 25 deg.C, electrolyzing while maintaining current density of 100mA/m 2 When the amount of energization reaches 2F/mol, energization is stopped. The organic phase was separated and purified to give 2-propionyl thiazole in 59% yield.
Example 12
An H-type electrolytic cell is used as a reactor, an anode is a platinum electrode, a cathode is a lead electrode, and an anode chamber and a cathode chamber are separated by a NaFiona-324 cation exchange membrane.
To the anode chamber were added 40mL of a saturated ammonium bisulfate solution, 0.3mmol of sodium tungstate, 10mmol of 2-propylthiazole, 0.5mmol of copper acetate, and 40g of dichloromethane in this order. 80ml of saturated potassium dihydrogen phosphate solution was sequentially added to the cathode chamber.
Stirring at constant temperature of 25 deg.C, electrolyzing while maintaining current density of 50mA/m 2 When the amount of energization reaches 2F/mol, energization is stopped. The organic phase was separated and purified to give 2-propionyl thiazole in 84% yield.
The above description is only a preferred embodiment of the present invention and is not intended to limit the present invention, and various modifications and changes may be made by those skilled in the art. Any modification, equivalent replacement, or improvement made within the spirit and principle of the present invention should be included in the protection scope of the present invention.
Claims (10)
1. An electrochemical synthesis method of 2-propionyl thiazole as a spice is characterized in that: the method comprises the following steps:
adding an ammonium bisulfate solution, sodium tungstate, 2-propylthiazole, a catalyst and dichloromethane into an anode chamber of an electrolytic cell, wherein the molar ratio of the sodium tungstate to the 2-propylthiazole to the catalyst to an organic solvent is 0.1-1:1-20; the volume ratio of the saturated ammonium bisulfate solution to the dichloromethane is 1;
adding saturated potassium dihydrogen phosphate solution into the cathode chamber;
the anode chamber and the cathode chamber of the electrolytic cell are separated by a cation exchange membrane;
and electrifying for electrolysis under the stirring state, and preparing the 2-propionyl thiazole in the anode chamber.
2. The process for the electrochemical synthesis of 2-propionyl thiazole, according to claim 1, characterized in that: the catalyst is selected from copper acetate, manganese acetate, silver nitrate, copper chloride or manganese sulfate.
3. The process for the electrochemical synthesis of 2-propionyl thiazole, according to claim 2, characterized in that: the catalyst is copper acetate, manganese acetate or silver nitrate.
4. The process for the electrochemical synthesis of 2-propionyl thiazole, according to claim 1, characterized in that: the cation exchange membrane is Nafion-324 or NaFion-424.
5. The process for the electrochemical synthesis of perfumery 2-propionyl thiazole, according to claim 1, characterized in that: the anode of the electrolytic chamber is a DSA electrode, a graphite electrode or a platinum electrode.
6. The process for the electrochemical synthesis of 2-propionyl thiazole, according to claim 1, characterized in that: the cathode is a graphite electrode or a lead alloy electrode.
7. The process for the electrochemical synthesis of 2-propionyl thiazole, according to claim 1, characterized in that: the molar ratio of the sodium tungstate to the 2-propylthiazole to the catalyst to the dichloromethane is 0.1-0.5; the volume ratio of the saturated ammonium bisulfate solution to the dichloromethane is 1.8-1.5.
8. The process for the electrochemical synthesis of perfumery 2-propionyl thiazole, according to claim 1, characterized in that: the current density of electrolysis is 80-250mA/m 2 。
9. The process for the electrochemical synthesis of 2-propionyl thiazole, according to claim 8, characterized in that: the current density of electrolysis is 80-150mA/m 2 。
10. The process for the electrochemical synthesis of 2-propionyl thiazole, according to claim 1, characterized in that: the ammonium bisulfate solution is a saturated ammonium bisulfate solution.
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| CN108977839A (en) * | 2018-08-17 | 2018-12-11 | 聊城大学 | A kind of synthetic method of 4-thiazolecarboxylic acid |
| CN114957159A (en) * | 2022-06-07 | 2022-08-30 | 济南悟通生物科技有限公司 | Preparation method of 2-acetyl thiazole |
| CN114990587A (en) * | 2022-06-30 | 2022-09-02 | 华南理工大学 | Electrochemical synthesis method of thiazole compound |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108977839A (en) * | 2018-08-17 | 2018-12-11 | 聊城大学 | A kind of synthetic method of 4-thiazolecarboxylic acid |
| CN114957159A (en) * | 2022-06-07 | 2022-08-30 | 济南悟通生物科技有限公司 | Preparation method of 2-acetyl thiazole |
| CN114990587A (en) * | 2022-06-30 | 2022-09-02 | 华南理工大学 | Electrochemical synthesis method of thiazole compound |
Non-Patent Citations (2)
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| 赵建宏 等: "电解法生产过硫酸铵的研究" * |
| 陈文坚 等: "钨酸盐／过钨酸盐体系阴极间接电氧化合成 红曲黄色素" * |
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