CN112225720A - Production method of thiophene-2-acetyl chloride - Google Patents
Production method of thiophene-2-acetyl chloride Download PDFInfo
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- CN112225720A CN112225720A CN202011245408.7A CN202011245408A CN112225720A CN 112225720 A CN112225720 A CN 112225720A CN 202011245408 A CN202011245408 A CN 202011245408A CN 112225720 A CN112225720 A CN 112225720A
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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Abstract
The invention is suitable for the technical field of chemical production, and provides a production method of thiophene-2-acetyl chloride, which comprises the following steps: mixing thiophene-2-ethanol, acetonitrile and a catalyst, heating to 70-90 ℃, then dropwise adding an oxidant for reaction, and then purifying to obtain thiophene-2-acetic acid; mixing thiophene-2-acetic acid and dichloromethane at the temperature of 30-35 ℃, dropwise adding thionyl chloride for carrying out heat preservation reaction, and then purifying to obtain the thiophene-2-acetyl chloride. The method for producing the thiophene-2-acetyl chloride provided by the invention has a simple process, prepares the thiophene-2-acetic acid by using the thiophene-2-ethanol as a raw material through an oxidation method, and then chloridizes the thiophene-2-acetyl chloride by using thionyl chloride to obtain the thiophene-2-acetyl chloride, and has higher product conversion rate and production efficiency.
Description
Technical Field
The invention belongs to the technical field of chemical production, and particularly relates to a production method of thiophene-2-acetyl chloride.
Background
Thiophene-2-acetyl chloride, i.e., 2-thiopheneacetyl chloride, CAS registry number 39098-97-0, formula C6H5ClOS. Thiophene-2-acetyl chloride is commonly used as a medical intermediate, and can be specifically used as an intermediate of broad-spectrum antibacterial drugs of cephalothin, cephaloridine and cefoxitin.
However, the existing production method of thiophene-2-acetyl chloride has the problems of complex process, low product purity, conversion rate and production efficiency and the like, and therefore, improvement is urgently needed.
Disclosure of Invention
The embodiment of the invention aims to provide a method for producing thiophene-2-acetyl chloride, aiming at solving the problems in the background art.
The embodiment of the invention is realized in such a way that the method for producing the thiophene-2-acetyl chloride comprises the following steps:
mixing thiophene-2-ethanol, acetonitrile and a catalyst, heating to 70-90 ℃, then dropwise adding an oxidant for reaction, and then purifying to obtain thiophene-2-acetic acid;
mixing thiophene-2-acetic acid and dichloromethane at the temperature of 30-35 ℃, dropwise adding thionyl chloride for carrying out heat preservation reaction, and then purifying to obtain the thiophene-2-acetyl chloride.
The reaction principle of the production method is as follows:
as a preferred scheme of the embodiment of the invention, the step of mixing thiophene-2-ethanol, acetonitrile and a catalyst, heating to 70-90 ℃, then dropwise adding an oxidant for reaction, and then purifying to obtain thiophene-2-acetic acid specifically comprises the following steps:
mixing thiophene-2-ethanol, acetonitrile and a catalyst, heating to 70-90 ℃, and then dropwise adding an oxidant for reaction to obtain a reaction solution;
adding a sodium sulfite solution and dilute sulfuric acid into the reaction solution for neutralization treatment, adjusting the pH to 5-7, and extracting to obtain an organic phase;
drying and distilling the organic phase to obtain a crude product;
and dissolving the crude product, and then concentrating, cooling and crystallizing to obtain the thiophene-2-acetic acid.
As another preferable mode of the embodiment of the present invention, the oxidizing agent is a sodium hypochlorite solution.
As another preferred embodiment of the present invention, the catalyst is tetramethylpiperidine oxide.
As another preferable scheme of the embodiment of the invention, the mass concentration of the sodium sulfite solution is 5-15%.
As another preferable scheme of the embodiment of the invention, the mass concentration of the dilute sulfuric acid is 5-15%.
As another preferable scheme of the embodiment of the present invention, the step of dissolving the crude product, and then concentrating and cooling for crystallization to obtain thiophene-2-acetic acid specifically includes:
adding activated carbon, petroleum ether and mother liquor into the crude product for dissolving, and then concentrating, cooling and crystallizing to obtain thiophene-2-acetic acid.
The production method of thiophene-2-acetyl chloride provided by the embodiment of the invention has a simple process, and the thiophene-2-acetic acid is prepared by using thiophene-2-ethanol as a raw material through an oxidation method, and then the product thiophene-2-acetyl chloride is obtained through chlorination by using thionyl chloride.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
Example 1
This embodiment provides a method for producing thiophene-2-acetyl chloride, comprising the steps of:
s1, adding a certain amount of thiophene-2-ethanol (including thiophene-2-ethanol recovered in subsequent processes), acetonitrile and a catalyst into a catalytic oxidation kettle, starting the reaction kettle, stirring, heating to 70 ℃, slowly and dropwise adding (about 6 h) a certain amount of oxidant solution, reacting for 1h to obtain a reaction solution, cooling to normal temperature, and pumping the reaction solution into a neutralization water washing kettle. Wherein, the oxidant is sodium hypochlorite solution, and the catalyst is tetramethylpiperidine oxide.
S2, dropwise adding a quantitative 5% sodium sulfite solution into the neutralization water washing kettle for neutralizing an oxidant, then adding a quantitative 5% dilute sulfuric acid for neutralization, stirring for a period of time, and adjusting the pH value of the solution to 5 by using sodium hydroxide and sulfuric acid; then, a certain amount of ethyl acetate is added into the neutralization kettle for extraction for 3 times, a certain amount of water is added for extraction for 2 times, an organic phase is collected, and a water layer is discharged into a waste water tank.
S3, pumping the organic phase into a drying kettle, adding quantitative anhydrous magnesium sulfate, stirring and drying for 8 hours, putting into a filter to remove magnesium sulfate waste residues, and pumping the filtrate into a distillation kettle; and then, heating the filtrate in the distillation kettle to 95 ℃, distilling and recovering the mixed solvent of ethyl acetate, acetonitrile and thiophene-2-ethanol, separating by a rectification process, and recovering the ethyl acetate, the acetonitrile and the thiophene-2-ethanol for recycling to obtain a crude product.
S4, transferring the crude product into a dissolving crystallization kettle, adding a small amount of activated carbon, quantitative petroleum ether and mother liquor to dissolve at room temperature, transferring petroleum ether filtrate into a concentration kettle after heating and dissolving, and recovering petroleum ether under reduced pressure of-0.04 MPa of vacuum degree for cyclic application; pumping the residual solution into a crystallization kettle for cooling crystallization, placing the crystallized solution into a centrifuge for centrifugal separation, and returning the mother solution into the dissolution and decoloration kettle for reuse; the obtained white powdery solid is a thiophene-2-acetic acid product, and is packaged and stored for later use after being dried.
S5, adding the thiophene-2-acetic acid into an acylation kettle, pumping dichloromethane into the acylation kettle, heating and stirring the mixture, controlling the temperature to be 30 ℃, dropwise adding thionyl chloride within 2 hours, and continuing to perform heat preservation reaction for 1 hour; then, the 2-thiophene acetyl chloride product can be obtained by suction filtration, desolventization and reduced pressure distillation. And (4) carrying out suction filtration to remove unreacted raw materials (for reuse). In addition, the temperature of the kettle is raised to 40 ℃, and the solvent dichloromethane is firstly distilled out (recycled and reused); then carrying out reduced pressure distillation (the vacuum degree is-0.065 MPa), and distilling out a product, namely thiophene acetyl chloride; continuously raising the temperature to 115 ℃, distilling under reduced pressure (vacuum degree-0.09 MPa), and distilling out the residual thionyl chloride (recycling and reusing) until no liquid flows; collecting the distillation residual liquid in the kettle in a waste liquid tank, and entrusting treatment.
Example 2
This embodiment provides a method for producing thiophene-2-acetyl chloride, comprising the steps of:
s1, adding a certain amount of thiophene-2-ethanol (including thiophene-2-ethanol recovered in subsequent processes), acetonitrile and a catalyst into a catalytic oxidation kettle, starting the reaction kettle, stirring, heating to 90 ℃, slowly and dropwise adding (about 6 h) a certain amount of oxidant solution, reacting for 1h to obtain a reaction solution, cooling to normal temperature, and pumping the reaction solution into a neutralization water washing kettle. Wherein, the oxidant is sodium hypochlorite solution, and the catalyst is tetramethylpiperidine oxide.
S2, dropwise adding a quantitative 15% sodium sulfite solution into the neutralization water washing kettle for neutralizing an oxidant, then adding a quantitative 15% dilute sulfuric acid for neutralization, stirring for a period of time, and adjusting the pH value of the solution to 7 by using sodium hydroxide and sulfuric acid; then, a certain amount of ethyl acetate is added into the neutralization kettle for extraction for 3 times, a certain amount of water is added for extraction for 2 times, an organic phase is collected, and a water layer is discharged into a waste water tank.
S3, pumping the organic phase into a drying kettle, adding quantitative anhydrous magnesium sulfate, stirring and drying for 8 hours, putting into a filter to remove magnesium sulfate waste residues, and pumping the filtrate into a distillation kettle; and then, heating the filtrate in the distillation kettle to 95 ℃, distilling and recovering the mixed solvent of ethyl acetate, acetonitrile and thiophene-2-ethanol, separating by a rectification process, and recovering the ethyl acetate, the acetonitrile and the thiophene-2-ethanol for recycling to obtain a crude product.
S4, transferring the crude product into a dissolving crystallization kettle, adding a small amount of activated carbon, quantitative petroleum ether and mother liquor to dissolve at room temperature, transferring petroleum ether filtrate into a concentration kettle after heating and dissolving, and recovering petroleum ether under reduced pressure of-0.04 MPa of vacuum degree for cyclic application; pumping the residual solution into a crystallization kettle for cooling crystallization, placing the crystallized solution into a centrifuge for centrifugal separation, and returning the mother solution into the dissolution and decoloration kettle for reuse; the obtained white powdery solid is a thiophene-2-acetic acid product, and is packaged and stored for later use after being dried.
S5, adding the thiophene-2-acetic acid into an acylation kettle, pumping dichloromethane into the acylation kettle, heating and stirring the mixture, controlling the temperature to be 35 ℃, dropwise adding thionyl chloride within 2 hours, and continuing to perform heat preservation reaction for 1 hour; then, the 2-thiophene acetyl chloride product can be obtained by suction filtration, desolventization and reduced pressure distillation. And (4) carrying out suction filtration to remove unreacted raw materials (for reuse). In addition, the temperature of the kettle is raised to 40 ℃, and the solvent dichloromethane is firstly distilled out (recycled and reused); then carrying out reduced pressure distillation (the vacuum degree is-0.065 MPa), and distilling out a product, namely thiophene acetyl chloride; continuously raising the temperature to 115 ℃, distilling under reduced pressure (vacuum degree-0.09 MPa), and distilling out the residual thionyl chloride (recycling and reusing) until no liquid flows; collecting the distillation residual liquid in the kettle in a waste liquid tank, and entrusting treatment.
Example 3
This embodiment provides a method for producing thiophene-2-acetyl chloride, comprising the steps of:
s1, adding a certain amount of thiophene-2-ethanol (including thiophene-2-ethanol recovered in subsequent processes), acetonitrile and a catalyst into a catalytic oxidation kettle, starting the reaction kettle, stirring, heating to 75 ℃, slowly and dropwise adding (about 6 h) a certain amount of oxidant solution, reacting for 1h to obtain a reaction solution, cooling to normal temperature, and pumping the reaction solution into a neutralization water washing kettle. Wherein, the oxidant is sodium hypochlorite solution, and the catalyst is tetramethylpiperidine oxide.
S2, dropwise adding a quantitative 8% sodium sulfite solution into the neutralization water washing kettle for neutralizing an oxidant, then adding a quantitative 8% dilute sulfuric acid for neutralization, stirring for a period of time, and adjusting the pH value of the solution to 5.5 by using sodium hydroxide and sulfuric acid; then, a certain amount of ethyl acetate is added into the neutralization kettle for extraction for 3 times, a certain amount of water is added for extraction for 2 times, an organic phase is collected, and a water layer is discharged into a waste water tank.
S3, pumping the organic phase into a drying kettle, adding quantitative anhydrous magnesium sulfate, stirring and drying for 8 hours, putting into a filter to remove magnesium sulfate waste residues, and pumping the filtrate into a distillation kettle; and then, heating the filtrate in the distillation kettle to 95 ℃, distilling and recovering the mixed solvent of ethyl acetate, acetonitrile and thiophene-2-ethanol, separating by a rectification process, and recovering the ethyl acetate, the acetonitrile and the thiophene-2-ethanol for recycling to obtain a crude product.
S4, transferring the crude product into a dissolving crystallization kettle, adding a small amount of activated carbon, quantitative petroleum ether and mother liquor to dissolve at room temperature, transferring petroleum ether filtrate into a concentration kettle after heating and dissolving, and recovering petroleum ether under reduced pressure of-0.04 MPa of vacuum degree for cyclic application; pumping the residual solution into a crystallization kettle for cooling crystallization, placing the crystallized solution into a centrifuge for centrifugal separation, and returning the mother solution into the dissolution and decoloration kettle for reuse; the obtained white powdery solid is a thiophene-2-acetic acid product, and is packaged and stored for later use after being dried.
S5, adding the thiophene-2-acetic acid into an acylation kettle, pumping dichloromethane into the acylation kettle, heating and stirring the mixture, controlling the temperature to be 31 ℃, dropwise adding thionyl chloride within 2 hours, and continuing to perform heat preservation reaction for 1 hour; then, the 2-thiophene acetyl chloride product can be obtained by suction filtration, desolventization and reduced pressure distillation. And (4) carrying out suction filtration to remove unreacted raw materials (for reuse). In addition, the temperature of the kettle is raised to 40 ℃, and the solvent dichloromethane is firstly distilled out (recycled and reused); then carrying out reduced pressure distillation (the vacuum degree is-0.065 MPa), and distilling out a product, namely thiophene acetyl chloride; continuously raising the temperature to 115 ℃, distilling under reduced pressure (vacuum degree-0.09 MPa), and distilling out the residual thionyl chloride (recycling and reusing) until no liquid flows; collecting the distillation residual liquid in the kettle in a waste liquid tank, and entrusting treatment.
Example 4
This embodiment provides a method for producing thiophene-2-acetyl chloride, comprising the steps of:
s1, adding a certain amount of thiophene-2-ethanol (including thiophene-2-ethanol recovered in subsequent processes), acetonitrile and a catalyst into a catalytic oxidation kettle, starting the reaction kettle, stirring, heating to 85 ℃, slowly and dropwise adding (about 6 h) a certain amount of oxidant solution, reacting for 1h to obtain a reaction solution, cooling to normal temperature, and pumping the reaction solution into a neutralization water washing kettle. Wherein, the oxidant is sodium hypochlorite solution, and the catalyst is tetramethylpiperidine oxide.
S2, dropwise adding a quantitative 12% sodium sulfite solution into the neutralization water washing kettle for neutralizing an oxidant, then adding a quantitative 12% dilute sulfuric acid for neutralization, stirring for a period of time, and adjusting the pH value of the solution to 6.5 by using sodium hydroxide and sulfuric acid; then, a certain amount of ethyl acetate is added into the neutralization kettle for extraction for 3 times, a certain amount of water is added for extraction for 2 times, an organic phase is collected, and a water layer is discharged into a waste water tank.
S3, pumping the organic phase into a drying kettle, adding quantitative anhydrous magnesium sulfate, stirring and drying for 8 hours, putting into a filter to remove magnesium sulfate waste residues, and pumping the filtrate into a distillation kettle; and then, heating the filtrate in the distillation kettle to 95 ℃, distilling and recovering the mixed solvent of ethyl acetate, acetonitrile and thiophene-2-ethanol, separating by a rectification process, and recovering the ethyl acetate, the acetonitrile and the thiophene-2-ethanol for recycling to obtain a crude product.
S4, transferring the crude product into a dissolving crystallization kettle, adding a small amount of activated carbon, quantitative petroleum ether and mother liquor to dissolve at room temperature, transferring petroleum ether filtrate into a concentration kettle after heating and dissolving, and recovering petroleum ether under reduced pressure of-0.04 MPa of vacuum degree for cyclic application; pumping the residual solution into a crystallization kettle for cooling crystallization, placing the crystallized solution into a centrifuge for centrifugal separation, and returning the mother solution into the dissolution and decoloration kettle for reuse; the obtained white powdery solid is a thiophene-2-acetic acid product, and is packaged and stored for later use after being dried.
S5, adding the thiophene-2-acetic acid into an acylation kettle, pumping dichloromethane into the acylation kettle, heating and stirring the mixture, controlling the temperature to be 34 ℃, dropwise adding thionyl chloride within 2 hours, and continuing to perform heat preservation reaction for 1 hour; then, the 2-thiophene acetyl chloride product can be obtained by suction filtration, desolventization and reduced pressure distillation. And (4) carrying out suction filtration to remove unreacted raw materials (for reuse). In addition, the temperature of the kettle is raised to 40 ℃, and the solvent dichloromethane is firstly distilled out (recycled and reused); then carrying out reduced pressure distillation (the vacuum degree is-0.065 MPa), and distilling out a product, namely thiophene acetyl chloride; continuously raising the temperature to 115 ℃, distilling under reduced pressure (vacuum degree-0.09 MPa), and distilling out the residual thionyl chloride (recycling and reusing) until no liquid flows; collecting the distillation residual liquid in the kettle in a waste liquid tank, and entrusting treatment.
Example 5
This embodiment provides a method for producing thiophene-2-acetyl chloride, comprising the steps of:
s1, adding a certain amount of thiophene-2-ethanol (including thiophene-2-ethanol recovered in subsequent processes), acetonitrile and a catalyst into a catalytic oxidation kettle, starting the reaction kettle, stirring, heating to 80 ℃, slowly and dropwise adding (about 6 h) a certain amount of oxidant solution, reacting for 1h to obtain a reaction solution, cooling to normal temperature, and pumping the reaction solution into a neutralization water washing kettle. Wherein, the oxidant is sodium hypochlorite solution, and the catalyst is tetramethylpiperidine oxide.
S2, dropwise adding a quantitative 10% sodium sulfite solution into the neutralization water washing kettle for neutralizing an oxidant, then adding a quantitative 10% dilute sulfuric acid for neutralization, stirring for a period of time, and adjusting the pH value of the solution to 6 by using sodium hydroxide and sulfuric acid; then, a certain amount of ethyl acetate is added into the neutralization kettle for extraction for 3 times, a certain amount of water is added for extraction for 2 times, an organic phase is collected, and a water layer is discharged into a waste water tank.
S3, pumping the organic phase into a drying kettle, adding quantitative anhydrous magnesium sulfate, stirring and drying for 8 hours, putting into a filter to remove magnesium sulfate waste residues, and pumping the filtrate into a distillation kettle; and then, heating the filtrate in the distillation kettle to 95 ℃, distilling and recovering the mixed solvent of ethyl acetate, acetonitrile and thiophene-2-ethanol, separating by a rectification process, and recovering the ethyl acetate, the acetonitrile and the thiophene-2-ethanol for recycling to obtain a crude product.
S4, transferring the crude product into a dissolving crystallization kettle, adding a small amount of activated carbon, quantitative petroleum ether and mother liquor to dissolve at room temperature, transferring petroleum ether filtrate into a concentration kettle after heating and dissolving, and recovering petroleum ether under reduced pressure of-0.04 MPa of vacuum degree for cyclic application; pumping the residual solution into a crystallization kettle for cooling crystallization, placing the crystallized solution into a centrifuge for centrifugal separation, and returning the mother solution into the dissolution and decoloration kettle for reuse; the obtained white powdery solid is a thiophene-2-acetic acid product, and is packaged and stored for later use after being dried.
S5, adding the thiophene-2-acetic acid into an acylation kettle, pumping dichloromethane into the acylation kettle, heating and stirring the mixture, controlling the temperature to be 33 ℃, dropwise adding thionyl chloride within 2 hours, and continuing to perform heat preservation reaction for 1 hour; then, the 2-thiophene acetyl chloride product can be obtained by suction filtration, desolventization and reduced pressure distillation. And (4) carrying out suction filtration to remove unreacted raw materials (for reuse). In addition, the temperature of the kettle is raised to 40 ℃, and the solvent dichloromethane is firstly distilled out (recycled and reused); then carrying out reduced pressure distillation (the vacuum degree is-0.065 MPa), and distilling out a product, namely thiophene acetyl chloride; continuously raising the temperature to 115 ℃, distilling under reduced pressure (vacuum degree-0.09 MPa), and distilling out the residual thionyl chloride (recycling and reusing) until no liquid flows; collecting the distillation residual liquid in the kettle in a waste liquid tank, and entrusting treatment.
In addition, thiophene-2-acetyl chloride was produced by the production method provided in the above example 5, and the material balance analysis thereof is shown in tables 1 and 2. Wherein, the purity of the obtained thiophene-2-acetic acid product is 98.5 percent.
TABLE 1
TABLE 2
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the present invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent shall be subject to the appended claims.
Claims (7)
1. The production method of thiophene-2-acetyl chloride is characterized by comprising the following steps:
mixing thiophene-2-ethanol, acetonitrile and a catalyst, heating to 70-90 ℃, then dropwise adding an oxidant for reaction, and then purifying to obtain thiophene-2-acetic acid;
mixing thiophene-2-acetic acid and dichloromethane at the temperature of 30-35 ℃, dropwise adding thionyl chloride for carrying out heat preservation reaction, and then purifying to obtain the thiophene-2-acetyl chloride.
2. The method for producing thiophene-2-acetyl chloride according to claim 1, wherein the step of mixing thiophene-2-ethanol, acetonitrile and a catalyst, heating to 70-90 ℃, then dropwise adding an oxidant for reaction, and then purifying to obtain thiophene-2-acetic acid specifically comprises:
mixing thiophene-2-ethanol, acetonitrile and a catalyst, heating to 70-90 ℃, and then dropwise adding an oxidant for reaction to obtain a reaction solution;
adding a sodium sulfite solution and dilute sulfuric acid into the reaction solution for neutralization treatment, adjusting the pH to 5-7, and extracting to obtain an organic phase;
drying and distilling the organic phase to obtain a crude product;
and dissolving the crude product, and then concentrating, cooling and crystallizing to obtain the thiophene-2-acetic acid.
3. The method for producing thiophene-2-acetyl chloride according to claim 1 or 2, wherein the oxidizing agent is a sodium hypochlorite solution.
4. The method for producing thiophene-2-acetyl chloride according to claim 1 or 2, wherein the catalyst is tetramethylpiperidine oxide.
5. The method for producing thiophene-2-acetyl chloride according to claim 2, wherein the mass concentration of the sodium sulfite solution is 5-15%.
6. The method for producing thiophene-2-acetyl chloride according to claim 2, wherein the mass concentration of the dilute sulfuric acid is 5-15%.
7. The method for producing thiophene-2-acetyl chloride according to claim 2, wherein the step of dissolving the crude product, concentrating, cooling and crystallizing to obtain thiophene-2-acetic acid specifically comprises:
adding activated carbon, petroleum ether and mother liquor into the crude product for dissolving, and then concentrating, cooling and crystallizing to obtain thiophene-2-acetic acid.
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| CN112851632A (en) * | 2020-12-29 | 2021-05-28 | 徐州砥研医药科技有限公司 | Method for efficiently preparing thiophene medical intermediate |
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Application publication date: 20210115 |